Document:

EXHIBIT 4.2

 

INVESTMENT AGREEMENT

 

This INVESTMENT
AGREEMENT, dated as of July 31, 2012 (this “Agreement”), is entered into by and between Triangle Petroleum
Corporation, a Nevada corporation (“Triangle”), NGP Natural Resources X, L.P., a Delaware limited partnership
(the “Parent”) and NGP Triangle Holdings, LLC, a Delaware limited liability company (the “Purchaser”).

 

RECITALS

 

WHEREAS, pursuant to
the Note Purchase Agreement, dated as of the date hereof, between Triangle and the Purchaser (the “Purchase Agreement”),
Triangle is agreeing to issue and sell to the Purchaser a convertible promissory note (the “Convertible Note”),
which is convertible into shares of common stock, par value $0.00001 per share, of Triangle (the “Common Stock”);

 

WHEREAS, the Purchaser
is the “Purchaser” under the Purchase Agreement;

 

WHEREAS, to induce
the Purchaser to enter into the Purchase Agreement and the transactions contemplated thereby, Triangle is required to deliver this
Agreement, duly executed by Triangle, to the Purchaser contemporaneously with the Closing of the transaction contemplated by the
Purchase Agreement;

 

WHEREAS, the Purchaser’s
investment in Triangle pursuant to the Purchase Agreement is reasonably expected to benefit Triangle; and

 

WHEREAS, Triangle believes
it to be in the best interests of Triangle, and the Purchaser believes it to be in the best interests of the Purchaser, to have
certain agreements in respect of the certain rights and obligations of the Purchaser and the Parent pursuant to the terms of this
Agreement.

 

NOW, THEREFORE, in
consideration of the mutual covenants and agreements set forth herein and for good and valuable consideration, the receipt and
sufficiency of which is hereby acknowledged by each party hereto, the parties hereby agree as follows:

 

ARTICLE
I

DEFINITIONS

 

Section
1.01        Definitions. Capitalized terms used in this Agreement
and not defined herein shall have the meanings ascribed to such terms in the Purchase Agreement. As used in this Agreement, the
following terms have the meanings indicated:

 

“Affiliate”
means, with respect to a specified Person, any other Person, whether now in existence or hereafter created, directly or indirectly
controlling, controlled by or under direct or indirect common control with such specified Person. For purposes of this definition,
“control” (including, with correlative meanings, “controlling,” “controlled by” and “under
common control with”) means the power to direct or cause the direction of the management and policies of such Person, directly
or indirectly, whether through the ownership of voting securities, by contract or otherwise; provided, however, that
“Affiliate” shall not be deemed to include any Portfolio Company.

 

    	 

    	 

    

 

“Agreement”
shall have the meaning specified in the introductory paragraph of this Agreement.

 

“Board”
means the Board of Directors of Triangle or any duly authorized committee thereof.

 

“Capital Leases”
means, for any Person, any lease of any property by such Person as lessee which would, in accordance with GAAP, be required to
be classified and accounted for as a capital lease on the balance sheet of such Person.

 

“Common Stock”
shall have the meaning specified in the Recitals to this Agreement.

 

“Consolidated
Leverage Ratio” means as of any date of determination, the ratio of (x) the aggregate amount of EBITDAX of Triangle for
the most recently completed fiscal quarter ending prior to the date of determination for which financial statements are in existence
multiplied by four to (y) Pro Forma Indebtedness.

 

“Convertible
Note” shall have the meaning specified in the Recitals to this Agreement.

 

“Conversion
Shares” means the Common Stock issuable upon conversion of the Convertible Note in accordance with the terms of the Convertible
Note.

 

“Designated
Director” shall have the meaning specified in Section 2.01(a) of this Agreement.

 

“Dispose”
(including the correlative terms “Disposed” and “Disposition”) means any sale, assignment,
transfer, conveyance, gift, pledge, distribution, hypothecation or other encumbrance or any other disposition, whether voluntary,
involuntary or by operation of Law, whether effected directly or indirectly.

 

“EBITDAX”
means for Triangle, on a consolidated basis for any period, the sum of (a) Net Income for such period (which if such amount constitutes
net loss, shall be reflected as a negative number), plus (b) without duplication and to the extent deducted in determining such
Net Income (i) Interest Expense for such period, plus (ii) Income Tax Expense for such period, plus (iii) depreciation, amortization,
depletion and exploration expenses for such period, plus (iv) non-cash charges resulting from extraordinary, non-recurring events
or circumstances for such period (including any provision for the reduction in the carrying value of assets recorded in accordance
with GAAP (including any “ceiling test” impairments as a result of the use of the full cost method of accounting) and
including non-cash charges resulting from the requirements of ASC 410, 718 and 815), minus (c) to the extent included in determining
Net Income, non-cash income resulting from extraordinary, non-recurring events or circumstances for such period and all other non-cash
items of income which were included in determining such Net Income (including non-cash income resulting from the requirements of
ASC 410, 718 and 815); provided that such EBITDAX shall be subject to pro forma adjustments for permitted acquisitions and
non-ordinary course asset sales assuming that such transactions had occurred on the first day of the determination period, which
adjustments shall be made in a manner, and subject to supporting documentation, reasonably acceptable to the Purchaser. Notwithstanding
the foregoing, EBITDAX shall be appropriately adjusted to exclude all amounts of revenues and expenses attributable to any minority
investments in Subsidiaries.

 

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“Equity Securities”
means, with respect to a Person, any shares, interests, participation or other equivalents (however designated) of corporate stock
(including any options, warrants or other rights to acquire corporate stock).

 

“Event of
Default” shall have the meaning given such term in the Convertible Note.

 

“Excluded
Securities” shall have the meaning specified in Section 4.01(d).

 

“GAAP”
means generally accepted accounting principles in the United States of America as of the date of the applicable calculation being
made pursuant to the terms of the Convertible Note.

 

“Hedging Arrangements”
means a hedge, call, swap, collar, floor, cap, option, forward sale or purchase or other contract or similar arrangement (including
any obligations to purchase or sell any commodity or security at a future date for a specific price).

 

“Hedging Transactions”
means any options, puts, warrants, swaps or other similar arrangements that are designed to transfer to another Person any of the
economic consequences of ownership of the Convertible Note or the Conversion Shares without a corresponding transfer of the ownership
of such security to such Person.

 

“Income Tax
Expense” means for Triangle and its Subsidiaries, on a consolidated basis for any period, all state and federal income
taxes paid or due to be paid during such period.

 

“Incur”
means issue, create, assume, guarantee, incur or otherwise become directly or indirectly liable for, contingently or otherwise.

 

“Indebtedness”
means, with respect to any Person, any indebtedness of that Person, whether or not contingent, in respect of borrowed money or
evidenced by bonds, debentures or similar instruments or letters of credit (or reimbursement agreements in respect thereof) or
bankers acceptances if and to the extent any of the foregoing indebtedness (other than letters of credit) would appear as a liability
upon a balance sheet of such Person prepared in accordance with GAAP, as well as all indebtedness of others secured by a lien on
any assets of such Person (whether or not such indebtedness is assumed by such Person) and, to the extent not otherwise included,
the guarantee by such Person of any Indebtedness of any other Person; provided, however, that Indebtedness shall
not include (i) any intercompany Indebtedness or (ii) any trade payables.

 

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“Independent
Director” means a person meeting the independence requirements under any rule or regulation of the Commission or NYSE
MKT (or any other principal stock exchange or market upon which the Common Stock may trade) or under applicable Law, exclusive
of any independence requirements applicable solely to members of any committee of the Board.

 

“Interest
Expense” means, for any period and with respect to any Person, total cash interest expense, letter of credit fees and
other fees and expenses incurred by such Person in connection with any indebtedness (including any Indebtedness outstanding under
the Convertible Note) for such period, whether paid or accrued (including that attributable to obligations which have been or should
be, in accordance with GAAP, recorded as Capital Leases), including, without limitation, all commissions, discounts and other fees
and charges owed with respect to letters of credit and bankers’ acceptance financing, fees owed with respect to secured obligations,
and net costs under Hedging Arrangements entered into addressing interest rates, all as determined in conformity with GAAP.

 

“Law”
means any applicable federal, state or local order, writ, injunction, judgment, settlement, award, decree, statute, law (including
common law), rule or regulation.

 

“Net Income”
means, for any period and with respect to any Person, the net income (or net loss) for such period for such Person after taxes
as determined in accordance with GAAP, including any cash net gain but excluding, however, (a) extraordinary items, including (i)
any net non-cash gain or loss during such period arising from the sale, exchange, retirement or other disposition of capital assets
(such term to include all fixed assets and all securities) other than in the ordinary course of business, and (ii) any write-up
or write-down of assets and (b) the cumulative effect of any change in GAAP.

 

“Notes”
shall have the meaning given such term in the Convertible Note.

 

“Offered Securities”
shall have the meaning specified in Section 4.01(a).

 

“Original
Issuance Date” shall have the meaning given such term in the Convertible Note.

 

“Parent”
shall have the meaning specified in the introductory paragraph of this Agreement.

 

“Person”
means any individual, corporation, partnership, joint venture, association, joint-stock company, trust, unincorporated organization,
limited liability company or government or any agency or political subdivision thereof or other entity.

 

“Portfolio
Company” means any portfolio company in which the Purchaser or any of its investment fund Affiliates have made a debt
or equity investment.

 

“Preemptive
Offer Notice” shall have the meaning specified in Section 4.01(a).

 

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“Preemptive
Offer Acceptance Notice” shall have the meaning specified in Section 4.01(b).

 

“Preemptive
Offer Notice” shall have the meaning specified in Section 4.01(a).

 

“Preemptive
Offer Period” shall have the meaning specified in Section 4.01(b).

 

“Pro Forma
Indebtedness” means as of any date of determination, the amount of Indebtedness of Triangle and its Subsidiaries as of
the date of determination (excluding the Indebtedness associated with the Convertible Note) after giving pro forma effect to the
Incurrence of any proposed new Indebtedness.

 

“Purchase
Agreement” shall have the meaning specified in the Recitals to this Agreement.

 

“Purchaser”
shall have the meaning specified in the introductory paragraph of this Agreement.

 

“Refused Securities”
shall have the meaning specified in Section 4.01(c).

 

“Resignation
Event” means that the Designated Director, as determined by the Board in good faith following compliance with the procedures
set forth below in this definition, (A) is prohibited or disqualified from serving as an Independent Director of Triangle;
(B) has engaged in acts or omissions constituting a breach of the Designated Director’s duty of loyalty to Triangle
or its stockholders; (C) has engaged or more likely than not, as determined by a majority of the independent directors of
the Board (other than the Designated Director), engaged in acts or omissions which involve moral turpitude, fraud, intentional
misconduct or an intentional violation of Law, (D) has engaged in any transaction involving Triangle from which the Designated
Director derived an improper personal benefit, or (E) has violated the attendance or other material Triangle policies applicable
to all Board members. Prior to making a determination that any Resignation Event described in clauses (A) through (E) above has
occurred, the Board shall provide the Designated Director with proper notice of a meeting of the Board in accordance with the Triangle
Bylaws at which the removal of such Designated Director will be considered. At such duly called and held Board meeting, the Board
shall provide the Designated Director with a reasonable opportunity to be heard and to present information relevant to the Board’s
proposed determination. The Board may make a determination that a Resignation Event has occurred only following its consideration
in good faith of such information presented by the Designated Director.

 

“Sales Transaction”
shall have the meaning specified in Section 3.01(b).

 

“Securities”
shall have the meaning specified in Section 3.01(a)(i).

 

“Significant
Event” means the entry by Triangle into an agreement providing for a sale of all or substantially all of Triangle’s
assets, a merger, tender offer, other business combination transaction or any combination of the foregoing that will result in
the Stockholders immediately prior to such transaction owning less than 30% of the outstanding Equity Securities of the combined
Person following such transaction.

 

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“Standstill
Termination Date” shall have the meaning specified in Section 3.01(a).

 

“Subsidiary”
means, as to any Person, any corporation or other entity of which: (i) such Person or a Subsidiary of such Person is a general
partner or manager; (ii) at least a majority of the outstanding equity interest having by the terms thereof ordinary voting
power to elect a majority of the board of directors or similar governing body of such corporation or other entity (irrespective
of whether or not at the time any equity interest of any other class or classes of such corporation or other entity shall have
or might have voting power by reason of the happening of any contingency) is at the time directly or indirectly owned or controlled
by such Person or one or more of its Subsidiaries; or (iii) any corporation or other entity as to which such Person consolidates
for accounting purposes.

 

“Termination
Event” means (A) the Purchaser and its Affiliates to which it has transferred the Convertible Note in accordance with
the terms thereof ceasing to own (such ownership being determined after giving pro forma effect to an assumed full conversion of
any outstanding portion of the Convertible Note) at least equal to the lesser of: (i) fifty percent (50%) of the shares of Common
Stock that would be issuable to the Purchaser upon full conversion of the Convertible Note on the date hereof and (ii) ten percent
(10%) of the shares of Common Stock outstanding as of the date of determination or (B) the Purchaser or its Affiliates shall have
breached any covenant or other obligation under Article III of this Agreement in any material respect and such breach shall
not have been cured within five Business Days following written notice of such breach or is of such nature that it cannot be cured.
Any shares of Common Stock acquired by the Purchaser (and its Affiliates to which it has transferred the Convertible Note in accordance
with the terms thereof) other than through the conversion of the Convertible Note shall not count towards the ownership requirements
set forth in clause (A)(i) above and any shares of Common Stock acquired by the Purchaser (and its Affiliates to which it has transferred
the Convertible Note in accordance with the terms thereof) other than through the conversion of the Convertible Note or pursuant
to Article IV shall not count towards the ownership requirements set forth in clause (A)(ii) above. Any limit imposed by the rules
of NYSE MKT (or any other principal stock exchange or market upon which the Common Stock may trade) on the number of shares of
Common Stock issuable to the Purchaser upon conversion of the Convertible Note will not be taken into account for purposes of this
definition.

 

“Triangle”
shall have the meaning specified in the introductory paragraph of this Agreement.

 

“Triangle
Bylaws” means the Bylaws of Triangle, as amended.

 

“Triangle
Credit Agreement” means the Credit Agreement dated as of April 12, 2012 among Triangle USA Petroleum Corporation, as
the borrower, Wells Fargo Bank, National Association, as administrative agent, issuing lender, arranger and sole bookrunner, and
the other lenders party thereto.

 

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ARTICLE
II

DIRECTOR DESIGNATION RIGHTS

 

Section
2.01        Board Representation.

 

(a)        On
or prior to the date hereof, the Board shall adopt resolutions that (i) increase the number of natural persons that constitute
the whole Board by one (1) person and (ii) fill the vacancy created by virtue of such increase in the size of the Board with
an individual designated by the Purchaser, in each case pursuant to the Triangle Organizational Documents, who must in the reasonable
judgment of Triangle, (A) qualify as an Independent Director, (B) have the requisite skill and experience to serve as a director
of a publicly traded company, (C) not be prohibited or disqualified from serving as a director of Triangle pursuant to the
Triangle Bylaws (as in effect as of the date hereof or as amended in accordance with Section 4.02) or any rule or regulation of
the Commission, NYSE MKT (or any other principal stock exchange or market upon which the Common Stock may trade) or by applicable
Law and (D) otherwise be reasonably acceptable to Triangle (the “Designated Director,” which such Designated
Director shall initially be Roy A. Aneed). The Purchaser shall, and shall cause the Designated Director to, timely provide Triangle
with accurate and complete information relating to the Purchaser and the Designated Director that may be required to be disclosed
by Triangle under the Exchange Act. In addition, at Triangle’s request, the Purchaser shall cause the Designated Director
to complete and execute Triangle’s Standard Director and Officer Questionnaire and provide such other information as Triangle
may reasonably request prior to being admitted to the Board or standing for reelection at an annual meeting of Stockholders or
at such other time as may be requested by Triangle.

 

(b)        The
Designated Director will hold office until his or her term expires and such Designated Director’s successor has been duly
elected and qualified or until such Designated Director’s earlier death, resignation or removal.

 

(c)        In
order to designate an individual for appointment to the Board, the Purchaser must submit to Triangle a written notice in accordance
with the notice provisions set forth in Section 7.07 of the Purchase Agreement, which notice shall include (i) the name, age, business
address and residence address of such designee, (ii) a current resume and curriculum vitae of such designee and (iii) a statement
describing such designee’s qualifications.

 

(d)        Prior
to a Termination Event:

 

(i)        in
connection with each annual meeting of Stockholders, and subject to the conditions of Section 2.01(a) of this Agreement,
Triangle shall nominate the Designated Director for reelection to the Board and shall take all reasonable and lawful actions necessary
or advisable to cause the Board to recommend that the Stockholders vote “FOR” the election of the Designated Director;

 

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(ii)        promptly
following any annual meeting of Stockholders at which the Designated Director is not elected to the Board, and subject to the provisions
of Section 2.01(a) of this Agreement, the Board shall adopt resolutions that (A) increase the number of natural persons
that constitute the whole Board by one (1) person and (B) fill the vacancy created by virtue of such increase in the size
of the Board with the Designated Director; and if the Board is prevented by Section 3.1 of the Triangle Bylaws from complying with
clause (A) of this Section 2.01(d)(ii), the Board shall amend the Triangle Bylaws as necessary to permit the Board to comply
with clause (A) of this Section 2.01(d)(ii);

 

(iii)        any
Designated Director may be removed pursuant to Section 3.6 of the Triangle Bylaws, and any vacancy created by such removal shall
be filled by the Board with an individual designated by the Purchaser who, subject to the conditions of Section 2.01(a)
of this Agreement, shall become the Designated Director;

 

(iv)        upon
written notice from Triangle to the Purchaser that a Resignation Event has occurred, which notice shall set forth in reasonable
detail the facts and circumstances constituting the Resignation Event, the Purchaser will cause the Designated Director then serving
as a member of the Board to resign as a member of the Board within two (2) Business Days of such written notice; and

 

(v)        any
vacancy caused by the death, disability or resignation of the Designated Director shall be filled by the Board with an individual
designated by the Purchaser who, subject to the conditions of Section 2.01(a) of this Agreement, shall become the Designated
Director.

 

(e)        Any
action by the Purchaser to designate or replace the Designated Director shall be evidenced in writing furnished to Triangle and
shall be signed by or on behalf of the Purchaser.

 

(f)        Prior
to designating a Designated Director, the Purchaser shall enter into a written agreement in a form reasonably satisfactory to Triangle
with the Designated Director whereby such Designated Director agrees to resign as a member of the Board upon a Resignation Event,
a Termination Event or at the Purchaser’s request, as applicable. The Purchaser acknowledges and agrees that such an agreement
is in the best interest of Triangle and the Purchaser, and that Triangle shall be a third party beneficiary of the terms and conditions
of such an agreement, and Triangle shall have the right to enforce such an agreement to the same extent as the parties thereto.

 

(g)        Triangle
shall not take any action that would lessen, restrict, prevent or otherwise have an adverse effect upon the foregoing rights of
the Purchaser to Board representation, including by nominating more directors for election to the Board than the number of directors
constituting the full Board; provided, however, that Triangle shall not be prohibited from taking such action that
the Board determines (i) may be necessary to (A) comply with any rule or regulation of the Commission or NYSE MKT (or
any other principal stock exchange or market upon which the Common Stock may trade) or (B) comply with applicable Law or (ii) is
required to comply with the provisions of the Triangle Organizational Documents.

 

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Section
2.02        Termination of Director Designation Rights. Upon the occurrence
of a Termination Event, the Purchaser’s right to designate, and Triangle’s obligation to nominate, the Designated
Director shall automatically terminate, and the Purchaser shall cause the Designated Director then serving as a member of the
Board, promptly upon (and in any event within two (2) Business Days following) receipt of a written request from Triangle, to
resign as a member of the Board. In the event Triangle does not request that the Designated Director be caused to resign upon
occurrence of a Termination Event, such Designated Director will no longer be considered a designee of the Purchaser and will
be subject to election and reelection in accordance with the Triangle Bylaws. The Purchaser shall have the right at any time to
cause the Designated Director to resign as a member of the Board and to waive its rights to designate a nominee for election to
the Board.

 

Section
2.03        Director Indemnification. At all times while the Designated
Director is serving as a member of the Board, and following any such Designated Director’s death, resignation, removal or
other cessation as a director in such former Designated Director’s capacity as a former director, each Designated Director
shall be entitled to all rights to indemnification and exculpation as are then made available to any other member of the Board.
As between Triangle, on the one hand, and the Purchaser and its Affiliates, on the other hand, Triangle shall, in all events,
be the full indemnitor of first resort and shall not be entitled to any contribution, indemnification or other payment by or from
any of the Purchaser or its Affiliates.

 

Section
2.04        Corporate Opportunities.
Triangle hereby renounces any interest or expectancy in any business opportunity in which Parent or Purchaser or any of their respective
Affiliates or Portfolio Companies (including any officers or directors thereof) (the “NGP Group”)
participates or seeks to participate (each, a “Business Opportunity”)
other than a Business Opportunity that is presented to a Designated Director in such Person’s capacity as a director of Triangle
and with respect to which no other member of the NGP Group (other than the Designated Director) independently receives notice or
otherwise identifies such Business Opportunity (each Business Opportunity that is so renounced, being referred to as a “Renounced
Business Opportunity”). No member of the NGP Group, including any Designated
Director, shall have any obligation to communicate or offer any Renounced Business Opportunity to Triangle, and any member of the
NGP Group may pursue a Renounced Business Opportunity. Notwithstanding anything to the contrary in this Section 2.04,
Triangle shall not be prohibited from pursuing any Business Opportunity with respect to which it has renounced any interest or
expectancy as a result of this Section 2.04.

 

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ARTICLE
III

COVENANTS

 

Section
3.01       Standstill Obligation.

 

(a)        For
a period beginning on the date hereof and ending on the later of (A) the third anniversary of the date hereof and (B) the date
that the Purchaser and its Affiliates cease to own in the aggregate at least 10% of the then-outstanding Common Stock (calculated
on a fully-diluted basis using the treasury stock method and assuming full conversion of any outstanding portion of the Convertible
Note held by the Purchaser and its Affiliates) (the “Standstill Termination Date”), without the prior written
consent of Triangle, the Parent agrees that it shall not and shall use its reasonable best efforts to cause any other Person that
would otherwise be an Affiliate but for the fact that such Person is a Portfolio Company not to, nor shall it permit any of its
Affiliates to, nor shall the Parent agree, advise, assist, provide information or provide financing to others (including any Portfolio
Company) in order to, or permit its Affiliates to, and shall use its reasonable best efforts to cause any other Person that would
otherwise be an Affiliate but for the fact that such Person is a Portfolio Company not to, agree, advise, assist, provide information
or provide financing to others (including any Portfolio Company) in order to, individually or collectively, directly or indirectly:

 

(i)        acquire
or offer to acquire or agree to acquire from any Person, directly or indirectly, by purchase or merger, through the acquisition
of control of another Person, by joining a partnership, limited partnership or other “group” (within the meaning of
Section 13(d)(3) of the Exchange Act) or otherwise, beneficial ownership of any Equity Securities of Triangle, or direct or
indirect rights (including convertible securities) or options to acquire such beneficial ownership (collectively, the “Securities”)
(or otherwise act in concert with respect to any such Securities with any Person that so acquires, offers to acquire or agrees
to acquire); provided, however, that no such acquisition, offer to acquire or agreement to acquire shall be deemed
to occur solely due to: (a) the issuance of the Convertible Note (including the issuance of any Conversion Shares underlying
the Convertible Note), (b) a stock split, reverse stock split, reclassification, reorganization or other transaction by Triangle
affecting any class of the outstanding Equity Securities of Triangle generally, (c) a dividend of stock or other pro rata
distribution by Triangle to holders of its outstanding Equity Securities, (d) a purchase by Purchaser of Securities of Triangle
pursuant to its preemptive rights granted in Section 4.01 of this Agreement or (e) the issuance by Triangle of Securities
to the Purchaser or any of its Affiliates as compensation for service on the Board;

 

(ii)        except
as contemplated by Section 5.01 of the Purchase Agreement, make, or in any way participate in, directly or indirectly, any “solicitation”
of “proxies” to vote (as such terms are used in the Regulation 14A promulgated under the Exchange Act), become a “participant”
in, or encourage, support or aid any other Person to become a “participant,” in any “election contest”
(as such terms are defined in Rule 14a-11 promulgated under the Exchange Act) or initiate, propose or otherwise solicit Stockholders
for the approval of any Stockholder proposals (other than the Proposal and the election of the director nominee designated by the
Purchaser pursuant to this Agreement), in each case with respect to Triangle;

 

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(iii)        form,
join, in any way participate in, or encourage the formation of, a “group” (within the meaning of Section 13(d)(3)
of the Exchange Act) with respect to any voting securities of Triangle other than a “group” that consists solely of
Affiliates of the Purchaser;

 

(iv)        deposit
any securities of Triangle into a voting trust, or subject any securities of Triangle to any agreement or arrangement with respect
to the voting of such securities, or other agreement or arrangement having similar effect;

 

(v)        alone
or in concert with others, seek, or encourage, support or aid any effort, to influence or control the management, Board, business,
policies, affairs or actions of Triangle (other than through a Representative of the Purchaser who is appointed or elected to the
Board pursuant to this Agreement or otherwise nominated by the Board and elected by the Stockholders);

 

(vi)        request
Triangle (or any directors, officers, employees or agents of Triangle), directly or indirectly to amend, waive or modify any provision
of this Section 3.01; provided, however, that a request to amend, waive or modify any provision of this Section 3.01
shall not be prohibited so long as such request does not include an offer or statement of intent to do any of the foregoing;

 

(vii)       make
any public disclosure, or take any action which could reasonably be expected to require the Triangle to make any public disclosure,
with respect to any potential transaction or any of the matters set forth in this Section 3.01; or

 

(viii)      disclose
any intention, plan or arrangement inconsistent any provision of this Section 3.01.

 

The foregoing provisions of this Section 3.01(a)
shall terminate and be of no further force and effect upon the announcement by Triangle of a Significant Event.

 

(b)        If
prior to the Standstill Termination Date, Triangle or its Affiliates conduct a process with two or more potential bidders that
has been duly approved by the Board and relates to a sale of all or substantially all of Triangle’s assets, a merger, tender
offer, other business combination transaction, or any combination of the foregoing involving Triangle that would reasonably be
expected to result in the Stockholders immediately prior to such transaction owning less than 30% of the outstanding Equity Securities
of the combined Person following such transaction (a “Sales Transaction”), then Triangle agrees that it shall
provide the Purchaser with an invitation to bid, using substantially the same invitation to bid sent to other potential bidders
in such process, and shall provide to the Purchaser substantially the same information relating to the Triangle Entities that Triangle
provided in such process to such other potential bidders, subject to a confidentiality agreement acceptable to Triangle containing
confidentiality restrictions no more restrictive in the aggregate than those in the confidentiality agreement entered into by any
other potential bidder in connection with such process, and the restrictions set forth in Section 3.01(a) of this Agreement
shall not apply to any process or transaction described in this Section 3.01(b) for the limited purpose of allowing
the Purchaser to bid, negotiate and, with the approval and recommendation of the Board, complete a Sales Transaction as contemplated
by this paragraph. If Triangle elects not to pursue a Sales Transaction with the Purchaser following the process described in this
Section 3.01(b), then the restrictions in Section 3.01(a) shall continue to apply to the Purchaser.

 

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(c)        Notwithstanding
anything to the contrary in this Section 3.01, prior to the Standstill Termination Date, at Triangle’s request,
the Purchaser shall be permitted to provide strategic advice to Triangle from time to time.

 

Section
3.02      Hedging Transactions.
For so long as the Purchaser or any of its Affiliates own the Convertible Note or any Conversion Shares, the Purchaser shall not,
and shall cause any of its Affiliates not to enter into any Hedging Transactions.

 

ARTICLE
IV

RIGHTS OF THE PURCHASER

 

Section
4.01       Preemptive Rights.

 

(a)        Except
in the case of Excluded Securities, Triangle shall not issue, exchange or otherwise Dispose, agree to issue, exchange or otherwise
Dispose, or reserve or set aside for the same, any Equity Securities of Triangle or any securities convertible into or exchangeable
for Equity Securities of Triangle (the “Offered Securities”), unless in each case Triangle shall have first
given written notice to Purchaser (the “Preemptive Offer Notice”) at least 10 Business Days prior to entering
into a definitive agreement for such sale stating that Triangle proposes to sell such Offered Securities, the number or amount
of the Offered Securities proposed to be sold, the proposed purchase price or price range therefor and any other terms and conditions
of such offer.

 

(b)        On
or before the seventh Business Day following the date of the Preemptive Offer Notice (the “Preemptive Offer Period”),
the Purchaser shall have the option to subscribe for up to its pro rata share of such Offered Securities (based on its percentage
ownership of Common Stock calculated on a fully-diluted basis using the treasury stock method and assuming full conversion of
the Convertible Note without taking into account any limit imposed by NYSE MKT rules and regulations on the number of Conversion
Shares issuable upon conversion of the Convertible Note) by delivering written notice to Triangle (a “Preemptive Offer
Acceptance Notice”). Notwithstanding the preceding sentence, the number of Offered Securities that the Purchaser is
entitled to purchase shall not exceed an amount that would require Stockholder Approval under, or would result in a violation
of, the rules and regulations of NYSE MKT or any other principal stock exchange or market upon which the Offered Securities trade;
provided, however, that if the Purchaser cannot purchase at least 75% of the number of Offered Securities as to
which a Preemptive Offer Acceptance Notice has been given by the Purchaser as a result of the limitations set forth in this sentence,
then Triangle shall not issue, exchange or otherwise Dispose, agree to issue, exchange or otherwise Dispose, or reserve or set
aside for the same all or any part of the Offered Securities without the prior written consent of the Purchaser. Each Preemptive
Offer Acceptance Notice shall specify: (i) the amount of Offered Securities the Purchaser desires to subscribe for and (ii) the
prices at which the Purchaser is willing to purchase such amounts of the Offered Securities at each such price.

 

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(c)        Triangle
shall have 30 days from the expiration of the Preemptive Offer Period to enter into a definitive agreement to issue and sell all
or any part of such Offered Securities as to which a Preemptive Offer Acceptance Notice has not been given by the Purchaser (the
“Refused Securities”) to any other Persons, but only upon terms and conditions in all material respects, including
price, which are no more favorable, individually or in the aggregate, to such other Persons or less favorable, individually or
in the aggregate, to Triangle than those set forth in the Preemptive Offer Notice. Upon the closing, which shall occur at a reasonable
time and place within 60 days from the expiration of the Preemptive Offer Period (which such period shall be extended for up to
180 days with respect to any Person seeking to purchase Offered Securities, including the Purchaser, for such time as is necessary
to allow such Person to request any approvals required under the HSR Act) and shall include full payment to Triangle of the proceeds
from the sale to such other Persons of all the Refused Securities, the Purchaser shall purchase from Triangle, and Triangle shall
sell to the Purchaser, the Offered Securities with respect to which a Preemptive Offer Acceptance Notice was delivered by the Purchaser,
at the terms specified in the Preemptive Offer Notice. In each case, any Offered Securities not purchased by the Purchaser or any
other Persons in accordance with this Section 4.01 within 60 days (or such longer period if the time period within which
to close is extended as provided in the immediately preceding sentence) after the expiration of the Preemptive Offer Period may
not be sold or otherwise Disposed of until they are again offered to the Purchaser under the procedures specified in this Section
4.01.

 

(d)        The
rights of the Purchaser under this Section 4.01 shall terminate upon the occurrence of a Termination Event and shall not
apply to the following securities (the “Excluded Securities”):

 

(i)        the
issuance of any Equity Securities, or securities convertible into or exchangeable for Equity Securities, of Triangle pursuant to
any employee benefits or other compensation plan approved by the Board and the Stockholders;

 

(ii)        Equity
Securities, or securities convertible into or exchangeable for Equity Securities, of Triangle issued otherwise than for cash pursuant
to, a merger, consolidation, acquisition, disposition or similar business combination approved by the Board;

 

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(iii)        Equity
Securities, or securities convertible into or exchangeable for Equity Securities, of Triangle issued upon any stock dividend, stock
split or other pro-rata distribution, subdivision or combination of securities or other recapitalization of Triangle;

 

(iv)        Equity
Securities issued upon conversion of the Convertible Note and other convertible notes issued concurrently herewith; and

 

(v)        Equity
Securities, or securities convertible into or exchangeable for Equity Securities, of Triangle issued pursuant to the terms of a
“poison pill” or other stockholder rights plan.

 

Section
4.02        Approval Rights. So
long as 50% or more of the aggregate principal amount of the Convertible Note as of the Original Issuance Date is issued and outstanding
and held by the Purchaser or its permitted Affiliate transferres thereunder, Triangle shall not, and shall cause its Subsidiaries
not to, take any of the following actions without obtaining the prior written consent of the Purchaser:

 

(a)        Triangle
will not, and will not permit any of its Subsidiaries to, directly or indirectly, enter into, make, amend or conduct any transaction
(including making a payment to, the purchase, sale, lease or exchange of any property or the rendering of any service), contract,
agreement or understanding with or for the benefit of any Affiliate of Triangle. The restriction in this Section 4.02(a)
will not apply to:

 

(i)        any
such transaction, contract, agreement or understanding by and among (A) Triangle or any Subsidiary of Triangle and (B) any Subsidiary
of Triangle;

 

(ii)       any
issuance of Common Stock, or other payments, awards or grants in cash, Common Stock or otherwise pursuant to, or the funding of,
employment or severance agreements and other compensation arrangements, options to purchase Common Stock, restricted stock plans,
long-term incentive plans, stock appreciation rights plans, participation
plans or similar employee benefit plans and/or insurance and indemnification agreements provided to or for the benefit of directors,
officers and employees approved by the Board; provided that none of such transactions or payments involve the issuance of Equity
Securities in any Subsidiary of Triangle to officers and directors of Triangle; and

 

(iii)      advances
to employees, officers or directors in the ordinary course of business of Triangle or any of its Subsidiaries.

 

(b)        Triangle
will not amend, supplement, modify or restate its articles or certificate of incorporation or bylaws or other equivalent organizational
documents, in any manner that could reasonably be expected to be materially adverse to the Purchaser.

 

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(c)        Triangle
will not make any direct or indirect dividend or distribution (whether in cash, securities or other property) in respect of Equity
Securities of Triangle or any direct or indirect payment of any kind or character (whether in cash, securities or other property)
in consideration for any retirement, purchase, redemption or other acquisition of any Equity Securities of Triangle.

 

(d)        Except
in accordance with the Convertible Note, Triangle will not issue any Indebtedness that is convertible into any Equity Securities
of Triangle (or Indebtedness in connection with the issuance thereof the holder thereof receives or is entitled to receive Equity
Securities of Triangle) or issue any Equity Securities of Triangle if, in each case, such Equity Securities of Triangle are senior
to the Common Stock with respect to priority of dividends or distributions or upon liquidation or have voting rights that are senior
to, or superior to, the Common Stock.

 

(e)        Triangle
will not, and will not permit any of its Subsidiaries to, directly or indirectly, Incur any Indebtedness (other than pursuant to
the Triangle Credit Agreement or the terms of the Notes); provided, however, that Triangle may Incur Indebtedness
and any of its Subsidiaries may Incur Indebtedness if (i) on the date thereof the Consolidated Leverage Ratio does not exceed 5.0
to 1.0 (provided that the Notes are excluded from such calculation) and (ii) no Event of Default is occurring or would occur as
a consequence of the Incurrence of such Indebtedness.

 

ARTICLE
V

MISCELLANEOUS

 

Section
5.01        Share Measurements. Notwithstanding anything herein to the contrary,
all measurements and references in this Agreement related to Common Stock and shares of Common Stock issuable upon conversion
of the Convertible Note shall be, in each instance, adjusted as set forth in the Convertible Note.

 

Section
5.02        Entire Agreement. This Agreement, together with the Convertible
Note and the Purchase Agreement and the other agreements contemplated thereby, is intended by the parties as a final expression
of their agreement and intended to be a complete and exclusive statement of the agreement and understanding of the parties hereto
in respect of the subject matter contained herein. There are no restrictions, promises, warranties or undertakings other than
those set forth or referred to herein with respect to the rights granted by Triangle or any of its Affiliates or the Purchaser
or any of its Affiliates set forth herein. This Agreement supersedes all prior agreements and understandings between the parties
with respect to the subject matter hereof.

 

Section
5.03        Notices. All notices and demands provided for in this Agreement
shall be in writing and shall be given as provided in Section 7.07 of the Purchase Agreement.

 

    	15

    	 

    

 

Section
5.04        Interpretation. Section references in this Agreement are references
to the corresponding Section to this Agreement, unless otherwise specified. All references to instruments, documents, Contracts
and agreements are references to such instruments, documents, Contracts and agreements as the same may be amended, supplemented
and otherwise modified from time to time, unless otherwise specified. The word “including” shall mean “including
but not limited to” and shall not be construed to limit any general statement that it follows to the specific or similar
items or matters immediately following it. Any reference in this Agreement to $ shall mean U.S. dollars. Whenever any determination,
consent or approval is to be made or given by a party, such action shall be in such party’s sole discretion, unless otherwise
specified in this Agreement. If any provision in this Agreement is held to be illegal, invalid, not binding or unenforceable,
(i) such provision shall be fully severable and this Agreement shall be construed and enforced as if such illegal, invalid,
not binding or unenforceable provision had never comprised a part of this Agreement, and the remaining provisions shall remain
in full force and effect and (ii) the parties hereto shall negotiate in good faith to modify this Agreement so as to effect
the original intent of the parties as closely as possible in an acceptable manner in order that the transactions contemplated
hereby are consummated as originally contemplated to the greatest extent possible. When calculating the period of time before
which, within which or following which any act is to be done or step taken pursuant to this Agreement, the date that is the reference
date in calculating such period shall be excluded. If the last day of such period is a non-Business Day, the period in question
shall end on the next succeeding Business Day. Any words imparting the singular number only shall include the plural and vice
versa. The words such as “herein,” “hereinafter,” “hereof” and “hereunder” refer
to this Agreement as a whole and not merely to a subdivision in which such words appear unless the context otherwise requires.
The division of this Agreement into Sections and other subdivisions and the insertion of headings are for convenience of reference
only and shall not affect or be utilized in construing or interpreting this Agreement.

 

Section
5.05        Governing Law; Submission to Jurisdiction. This Agreement, and
all claims or causes of action (whether in contract or tort) that may be based upon, arise out of or relate to this Agreement
or the negotiation, execution or performance of this Agreement (including any claim or cause of action based upon, arising out
of or related to any representation or warranty made in or in connection with this Agreement), will be construed in accordance
with and governed by the Laws of the State of New York without regard to principles of conflicts of Laws (except that matters
to which the Law of the jurisdiction of formation of Triangle is applicable shall be subject to the internal laws of such state).
Any action against any party relating to the foregoing shall be brought in any federal or state court of competent jurisdiction
located within the State of New York in the Borough of Manhattan in the City of New York, and the parties hereto hereby irrevocably
submit to the non-exclusive jurisdiction of any federal or state court located within the State of New York in the Borough of
Manhattan in the City of New York over any such action. Each of the parties hereby irrevocably waives, to the fullest extent permitted
by applicable Law, any objection that it may now or hereafter have to the laying of venue of any such dispute brought in such
court or any defense of inconvenient forum for the maintenance of such dispute. Each of the parties hereto agrees that a judgment
in any such dispute may be enforced in other jurisdictions by suit on the judgment or in any other manner provided by Law.

 

    	16

    	 

    

 

Section
5.06         Waiver of Jury Trial. EACH OF THE PARTIES TO THIS AGREEMENT
HEREBY WAIVES, AND AGREES TO CAUSE ITS AFFILIATES TO WAIVE, TO THE FULLEST EXTENT PERMITTED BY LAW, ANY RIGHT TO TRIAL BY JURY
OF ANY CLAIM, DEMAND, ACTION OR CAUSE OF ACTION (i) ARISING UNDER THIS AGREEMENT OR (ii) IN ANY WAY CONNECTED WITH OR
RELATED OR INCIDENTAL TO THE DEALINGS OF THE PARTIES HERETO IN RESPECT OF THIS AGREEMENT OR ANY OF THE TRANSACTIONS RELATED HERETO,
IN EACH CASE WHETHER NOW EXISTING OR HEREAFTER ARISING, AND WHETHER IN CONTRACT, TORT, EQUITY OR OTHERWISE. EACH OF THE PARTIES
TO THIS AGREEMENT HEREBY AGREES AND CONSENTS THAT ANY SUCH CLAIM, DEMAND, ACTION OR CAUSE OF ACTION SHALL BE DECIDED BY COURT
TRIAL WITHOUT A JURY AND THAT THE PARTIES TO THIS AGREEMENT MAY FILE AN ORIGINAL COUNTERPART OF A COPY OF THIS AGREEMENT WITH
ANY COURT AS WRITTEN EVIDENCE OF THE CONSENT OF THE PARTIES HERETO TO THE WAIVER OF THEIR RIGHT TO TRIAL BY JURY.

 

Section
5.07         No Waiver; Modifications in Writing.

 

(a)        Delay.
No failure or delay on the part of any party in exercising any right, power or remedy hereunder shall operate as a waiver thereof,
nor shall any single or partial exercise of any such right, power or remedy preclude any other or further exercise thereof or the
exercise of any other right, power or remedy. The remedies provided for herein are cumulative and are not exclusive of any remedies
that may be available to a party at law or in equity or otherwise.

 

(b)        Specific
Waiver. Except as otherwise provided herein, no amendment, waiver, consent, modification or termination of any provision of
this Agreement shall be effective unless signed by each of the parties hereto affected by such amendment, waiver, consent, modification
or termination. Any amendment, supplement or modification of or to any provision of this Agreement, any waiver of any provision
of this Agreement and any consent to any departure by a party from the terms of any provision of this Agreement shall be effective
only in the specific instance and for the specific purpose for which made or given. Except where notice is specifically required
by this Agreement, no notice to or demand on a party in any case shall entitle such party to any other or further notice or demand
in similar or other circumstances. Any investigation by or on behalf of any party shall not be deemed to constitute a waiver by
the party taking such action of compliance with any representation, warranty, covenant or agreement contained herein.

 

Section
5.08        Execution in Counterparts. This Agreement may be executed in
any number of counterparts and by different parties hereto in separate counterparts, each of which counterparts, when so executed
and delivered, shall be deemed to be an original and all of which counterparts, taken together, shall constitute but one and the
same agreement.

 

    	17

    	 

    

 

Section
5.09        Binding Effect; Assignment. This Agreement will be binding upon
and inure to the benefit of the parties hereto and their respective successors and permitted assigns, but will not be assignable
or delegable by any party hereto without the prior written consent of each of the other parties; provided, however,
that any of the rights and obligations of the Purchaser hereunder may be transferred or assigned in whole or in part by the Purchaser
to any Affiliate of the Purchaser. Any such transferee shall agree to be bound by this Agreement. Notwithstanding the foregoing,
nothing in this Section 5.09 shall impose any limitation or restriction on the ability of the Parent or Purchaser to issue, sell
or transfer any interests in the Purchaser or any permitted Affiliate transferee hereunder to any other Person, so long as Parent
continues to control the Purchaser or such Affiliate.

 

Section
5.10        Independent Counsel. Each of the parties acknowledges that it
has been represented by independent counsel of its choice throughout all negotiations that have preceded the execution of this
Agreement and that it has executed the same with consent and upon the advice of said independent counsel. Each party and its counsel
cooperated in the drafting and preparation of this Agreement and the documents referred to herein, and any and all drafts relating
thereto will be deemed the work product of the parties and may not be construed against any party by reason of its preparation.
Accordingly, any rule of Law or any legal decision that would require interpretation of any ambiguities in this Agreement against
the party that drafted it is of no application and is hereby expressly waived.

 

Section
5.11        Specific Enforcement. Each of the parties acknowledges and agrees
that monetary damages would not adequately compensate an injured party for the breach of this Agreement by any party, that this
Agreement shall be specifically enforceable and that any breach or threatened breach of this Agreement shall be the proper subject
of a temporary or permanent injunction or restraining order without a requirement of posting bond. Further, each party hereto
waives any claim or defense that there is an adequate remedy at law for such breach or threatened breach.

 

Section
5.12        Further Assurances. Each of the parties hereto shall, from time
to time and without further consideration, execute such further instruments and take such other actions as any other party hereto
shall reasonably request in order to fulfill its obligations under this Agreement to effectuate the purposes of this Agreement.

 

[Signature Page Follows]

 

    	18

    	 

    

 

IN WITNESS WHEREOF,
the parties hereto execute this Agreement, effective as of the date first above written.

 

	 	TRIANGLE PETROLEUM CORPORATION
	 	 	 
	 	By:	/s/ Jonathan Samuels
	 	Name:	 Jonathan Samuels
	 	Title:	President and Chief Executive Officer
	 	 	 
	 	NGP NATURAL RESOURCES X, L.P.
	 	 	 
	 	By:	G.F.W. Energy X, L.P., its general partner
	 	 	 
	 	By:	GFW X, L.L.C., its general partner
	 	 	 
	 	By: 	/s/ Kenneth A. Hersh
	 	Name:  	Kenneth A. Hersh
	 	Title:	Authorized Member
	 	 	 
	 	NGP TRIANGLE HOLDINGS, LLC
	 	 	 
	 	By:	NGP Natural Resources X, L.P., its

managing member
	 	 	 
	 	By:	G.F.W. Energy X, L.P., its general partner
	 	 	 
	 	By:	GFW X, L.L.C., its general partner
	 	 	 
	 	By: 	/s/ Kenneth A. Hersh
	 	Name:	Kenneth A. Hersh
	 	Title:	Authorized Member

 

Signature Page to Investment AgreementEXHIBIT 4.3

 

REGISTRATION RIGHTS AGREEMENT

 

This Registration Rights
Agreement (this “Agreement”) is made and entered into as of July 31, 2012, by and between Triangle Petroleum
Corporation, a Nevada corporation (“Triangle”) and NGP Triangle Holdings, LLC, a Delaware limited liability
company (the “Purchaser”). Triangle and NGP are referred to collectively herein as the “Parties.”

 

WHEREAS, pursuant to
the Note Purchase Agreement, dated as of the date hereof, between Triangle and the Purchaser (the “Purchase Agreement”),
Triangle is agreeing to issue and sell to the Purchaser a convertible promissory note dated as of the date hereof (the “Convertible
Note”) in the aggregate principal amount of $120,000,000, which is convertible into shares of common stock, par value
$0.00001 per share, of Triangle (the “Common Stock”) as described therein; and

 

WHEREAS, Triangle has
agreed to provide the registration and other rights set forth in this Agreement for the benefit of the Purchaser pursuant to the
Purchase Agreement.

 

NOW THEREFORE, in consideration
of the mutual covenants and agreements set forth herein and for good and valuable consideration, the receipt and sufficiency of
which is hereby acknowledged by each party hereto, the parties hereby agree as follows:

 

1.            Definitions.
Capitalized terms used in this Agreement and not defined herein shall
have the meanings ascribed to such terms in the Purchase Agreement. As used in this Agreement, the following terms have the meanings
indicated:

 

“Affiliate”
of any specified Person means any other person which, directly or indirectly, is in control of, is controlled by, or is under common
control with, such specified Person. For purposes of this definition, control of a Person means the power, direct or indirect,
to direct or cause the direction of the management and policies of such Person, whether through ownership of voting securities,
by contract or otherwise; and the terms “controlling” and “controlled” have meanings correlative to the
foregoing.

 

“Agreement”
has the meaning set forth in the preamble.

 

“Automatic Shelf
Registration Statement” means an “automatic shelf registration statement” as defined under Rule 405.

 

“Blackout Period”
has the meaning set forth in Section 2(a).

 

“Board”
means the board of directors of Triangle.

 

“Business Day”
means any day other than a Saturday, Sunday, any federal holiday or any day on which banking institutions in the State of Texas
are authorized or required by law or governmental action to close.

 

“Commission”
means the Securities and Exchange Commission or any other federal agency then administering the Securities Act or Exchange Act.

 

    	1

    	 

    

  

“Common Stock”
has the meaning set forth in the recitals to this Agreement.

 

“Conversion
Shares” means the Common Stock issuable upon conversion of the Convertible Note in accordance with the terms of the Convertible
Note (including any Reference Property into which such Convertible Note shall become convertible pursuant to the terms of the Convertible
Note).

 

“Convertible
Note” has the meaning set forth in the recitals to this Agreement.

 

“Demand Notice”
has the meaning set forth in Section 2(a).

 

“Demand Registration”
has the meaning set forth in Section 2(a).

 

“Effective Date”
means the time and date that a Registration Statement is first declared effective by the Commission or otherwise becomes effective.

 

“Effectiveness
Period” has the meaning set forth in Section 2(a).

 

“Exchange Act”
means the Securities Exchange Act of 1934, as amended from time to time, and the rules and regulations of the Commission promulgated
thereunder.

 

“Holder”
means (i) the Purchaser unless and until the Purchaser ceases to hold the Convertible Note or any Registrable Securities and (ii)
any holder of Registrable Securities to whom registration rights conferred by this Agreement have been transferred in compliance
with Section 7(e) hereof; provided that any Person referenced in clause (ii) shall be a Holder only if such Person
agrees in writing to be bound by and subject to the terms set forth in this Agreement.

 

“Holder Indemnified
Persons” has the meaning set forth in Section 5(a).

 

“Initiating
Holder” has the meaning set forth in Section 2(a).

 

“Losses”
has the meaning set forth in Section 5(a).

 

“Parties”
has the meaning set forth in the preamble.

 

“Person”
means an individual or group, corporation, partnership, trust, incorporated or unincorporated association, joint venture, limited
liability company, joint stock company, government (or an agency or subdivision thereof) or other entity of any kind.

 

“Piggyback Notice”
has the meaning set forth in Section 2(b).

 

“Piggyback Registration”
has the meaning set forth in Section 2(b).

 

“Piggyback Request”
has the meaning set forth in Section 2(b).

 

“Proceeding”
means any action, claim, suit, proceeding or investigation (including a preliminary investigation or partial proceeding, such as
a deposition) pending or, to the knowledge of Triangle, to be threatened.

 

    	2

    	 

    

  

“Prospectus”
means the prospectus included in a Registration Statement (including a prospectus that includes any information previously omitted
from a prospectus filed as part of an effective Registration Statement in reliance upon Rule 430A, Rule 430B or Rule 430C promulgated
under the Securities Act), as amended or supplemented by any prospectus supplement, with respect to the terms of the offering of
any portion of the Registrable Securities covered by a Registration Statement and all other amendments and supplements to the Prospectus,
including post-effective amendments, and all material incorporated by reference or deemed to be incorporated by reference in such
Prospectus.

 

“Purchase Agreement”
has the meaning set forth in the recitals to this Agreement.

 

“Purchaser”
has the meaning set forth in the preamble.

 

“Reference Property”
has the meaning set forth in the Convertible Note.

 

“Registrable
Securities” means the Conversion Shares underlying the Convertible Note; provided, however, that Registrable
Securities shall not include: (i) any Conversion Shares that have been registered under the Securities Act and disposed of pursuant
to an effective registration statement or otherwise transferred to a Person who is not entitled to the registration and other rights
hereunder; (ii) any Conversion Shares that may be sold or transferred by the Holder thereof under Rule 144 under the Securities
Act without any limitation on the volume, timing, recipients or intended method or methods of distribution, including through the
use of an underwriter; and (iii) any Conversion Shares that cease to be outstanding (whether as a result of repurchase and cancellation,
conversion or otherwise).

 

“Registration
Expenses” has the meaning set forth in Section 4.

 

“Registration
Statement” means a registration statement in the form required to register the resale of the Registrable Securities under
the Securities Act and other applicable law, and including any Prospectus, amendments and supplements to each such registration
statement or Prospectus, including pre- and post-effective amendments, all exhibits thereto, and all material incorporated by reference
or deemed to be incorporated by reference in such registration statement.

 

“Rule 144”
means Rule 144 promulgated by the Commission pursuant to the Securities Act.

 

“Rule 405”
means Rule 405 promulgated by the Commission pursuant to the Securities Act.

 

“Rule 415”
means Rule 415 promulgated by the Commission pursuant to the Securities Act.

 

“Rule 424”
means Rule 424 promulgated by the Commission pursuant to the Securities Act.

 

    	3

    	 

    

  

“Securities
Act” means the Securities Act of 1933, as amended. 

 

“Selling Expenses”
means all underwriting discounts, selling commissions and stock transfer taxes applicable to the sale of Registrable Securities
and fees and disbursements of counsel for any Holder.

 

“Suspension
Notice” has the meaning set forth in Section 7(b).

 

“Suspension
Period” has the meaning set forth in Section 7(b).

 

“Trading Market”
means the principal national securities exchange on which Registrable Securities are listed.

 

“Triangle”
has the meaning set forth in the preamble.

 

“Triangle Indemnified
Persons” has the meaning set forth in Section 5(b).

 

“Triangle Securities”
means any equity interest of any class or series in Triangle.

 

“Underwritten
Offering” has the meaning set forth in Section 3(k).

 

“Underwritten
Offering Notice” has the meaning set forth in Section 3(k).

 

“VWAP”
means, as of a specified date and in respect of Registrable Securities, the volume weighted average price for such security on
the Trading Market with respect to the Registrable Securities for the five (5) trading days immediately preceding, but excluding,
such date.

 

“WKSI”
means a “well known seasoned issuer” as defined under Rule 405.

 

Unless the context requires
otherwise: (a) any pronoun used in this Agreement shall include the corresponding masculine, feminine or neuter forms; (b) references
to Sections and Annexes refer to Sections of and Annexes to this Agreement; (c) the terms “include”, “includes”,
“including” or words of like import shall be deemed to be followed by the words “without limitation”; (d)
the terms “hereof”, “herein” or “hereunder” refer to this Agreement as a whole and not to any
particular provision of this Agreement; (e) unless the context otherwise requires, the term “or” is not exclusive and
shall have the inclusive meaning of “and/or”; (f) defined terms herein will apply equally to both the singular
and plural forms and derivative forms of defined terms will have correlative meanings; (g) references to any law or statute shall
include all rules and regulations promulgated thereunder, and references to any law or statute shall be construed as including
any legal and statutory provisions consolidating, amending, succeeding or replacing the applicable law or statute; (h) references
to any Person include such Person’s successors and permitted assigns; and (i) references to “days” are to calendar
days unless otherwise indicated.

 

    	4

    	 

    

 

For the avoidance of
doubt, where this Agreement refers to allocation of rights on a pro rata basis to holders of Registrable Securities, such allocation
shall be determined considering the Convertible Note on an as-converted basis and as adjusted as provided in the Convertible Note.
For purposes of this Agreement, holders of the Convertible Note will be deemed to be holders of the number of Conversion Shares
issuable upon conversion of the Convertible Note held by such holder based on the Outstanding Balance (as defined in the Convertible
Note) at such time. Any limit imposed by the rules of NYSE MKT LLC on the number of Conversion Shares issuable to the Purchaser
upon conversion of the Convertible Note will not be taken into account for purposes of this definition. 

 

2.            Registration.

 

(a)            Demand
Registration.

 

(i)            Any
Holder that holds any Registrable Securities shall have the option and right, exercisable by delivering a written notice to Triangle
(a “Demand Notice,” and the Holder that delivers such a Demand Notice, the “Initiating Holder”),
to require Triangle to, pursuant to the terms of and subject to the limitations contained in this Agreement, prepare and file with
the Commission a Registration Statement registering the offering and sale of the number and type of Registrable Securities on the
terms and conditions specified in the Demand Notice in accordance with the intended timing and method or methods of distribution
thereof specified in the Demand Notice, which may include sales on a delayed or continuous basis pursuant to Rule 415 (a “Demand
Registration”). The Demand Notice must set forth the number of Registrable Securities that the Initiating Holder intends
to include in such Demand Registration. Notwithstanding anything to the contrary herein, in no event shall Triangle be required
to effectuate a Demand Registration for Registrable Securities having an aggregate value of less than $30 million based on the
VWAP of such Registrable Securities as of the date of the Demand Notice.

 

(ii)            Within
five Business Days of the receipt of the Demand Notice, Triangle shall give written notice of such Demand Notice to all Holders
and, as soon as reasonably practicable thereafter, shall, subject to the limitations of this Section 2(a), file a Registration
Statement covering all of the Registrable Securities that the Holders shall in writing request (such request to be given to Triangle
within three days of receipt of such notice of the Demand Notice given by Triangle pursuant to this Section 2(a)(ii)) to
be included in such Demand Registration as promptly as practicable as directed by the Initiating Holder in accordance with the
terms and conditions of the Demand Notice and use all commercially reasonable efforts to cause such Registration Statement to become
effective under the Securities Act and remain effective under the Securities Act until all Registrable Securities covered by such
Registration Statement have been sold (the “Effectiveness Period”).

 

(iii)            Subject
to the other limitations contained in this Agreement, Triangle is not obligated hereunder to effect (A) more than one Demand Registration
in any 12 month period, (B) more than a total of three Demand Registrations pursuant to this Agreement and (C) a subsequent Demand
Registration pursuant to a Demand Notice if a Registration Statement covering all of the Registrable Securities held by the Holders
providing such Demand Notice shall have become effective under the Securities Act and remains effective under the Securities Act
and is sufficient to permit offers and sales of the number and type of Registrable Securities on the terms and conditions specified
in the Demand Notice in accordance with the intended timing and method or methods of distribution thereof specified in the Demand
Notice.

 

    	5

    	 

    

  

(iv)            Notwithstanding
any other provision of this Section 2(a), Triangle shall not be required to effect a registration or file a Registration
Statement (or any amendment thereto) for a period of up to 60 days, if (A) the Board determines that a postponement is in the best
interest of Triangle and its stockholders generally due to a pending transaction involving Triangle, (B) the Board determines such
registration would render Triangle unable to comply with applicable securities laws or (C) the Board determines such registration
would require disclosure of material information that Triangle has a bona fide business purpose for preserving as confidential
(any such period, a “Blackout Period”); provided, however, that (i) in no event shall any
Blackout Period together with any Suspension Period collectively exceed an aggregate of 120 days in any 12 month period, (ii) during
any Blackout Period contemplated by Section 2(a)(iv)(B) or any Suspension Period, Triangle shall not engage in any transaction
involving the offer, issuance, sale, or purchase of Triangle Securities (whether for the benefit of Triangle or a third Person),
except transactions involving the issuance or purchase of Triangle Securities as contemplated by Triangle employee benefit plans
or employee or director arrangements or in connection with the conversion or exercise of outstanding securities, including the
Convertible Note, and (iii) during any Blackout Period contemplated by Section 2(a)(iv)(B) or (C) or any Suspension
Period, Triangle shall not file a registration statement (or any amendment or supplement thereto) for any other holder of registration
rights.

 

(v)            Triangle
may include in any such Demand Registration other Triangle Securities for sale for its own account or for the account of any other
Person; provided that if the managing underwriter, if any, for the Underwritten Offering determines that the type or number
of Triangle Securities proposed to be offered in such offering would likely have an adverse effect in any material respect on the
price, timing or distribution of the Registrable Securities proposed to be included in such offering, the Registrable Securities
to be sold by the Holders shall be included in such registration before any Triangle Securities proposed to be sold for the account
of Triangle or any other Person.

 

(vi)            Subject
to the limitations contained in this Agreement, Triangle shall effect any Demand Registration on Form S-3 (except if Triangle is
not then eligible to register for resale the Registrable Securities on Form S-3, in which case such Demand Registration shall be
effected on another appropriate form for such purpose pursuant to the Securities Act) and if Triangle becomes, and is at the time
of its receipt of a Demand Notice, a WKSI, the Demand Registration for any offering and selling of Registrable Securities shall
be effected pursuant to an Automatic Shelf Registration Statement, which shall be on Form S-3 or any equivalent or successor form
under the Securities Act (if available to Triangle); provided, however, that if at any time a Registration Statement
on Form S-3 is effective and a Holder provides written notice to Triangle that it intends to effect an offering of all or part
of the Registrable Securities included on such Registration Statement, Triangle will amend or supplement such Registration Statement
as may be necessary in order to enable such offering to take place.

 

    	6

    	 

    

  

(vii)            Without
limiting Section 3, in connection with any Demand Registration pursuant to and in accordance with this Section
2(a), Triangle shall, (A) promptly prepare and file or cause to be prepared and filed (1) such additional forms, amendments,
supplements, prospectuses, certificates, letters, opinions and other documents, as may be necessary or advisable to register or
qualify the securities subject to such Demand Registration, including under the securities laws of such states as the Holders shall
reasonably request; provided, however, that no such qualification shall be required in any jurisdiction where, as
a result thereof, Triangle would become subject to general service of process or to taxation or qualification to do business in
such jurisdiction solely as a result of registration and (2) such forms, amendments, supplements, prospectuses, certificates,
letters, opinions and other documents as may be necessary to apply for listing or to list the Registrable Securities subject to
such Demand Registration on the Trading Market and (B) do any and all other acts and things that may be reasonably necessary or
appropriate or reasonably requested by the Holders to enable the Holders to consummate a public sale of such Registrable Securities
in accordance with the intended timing and method or methods of distribution thereof.

 

(ix)            In
the event a Holder transfers Registrable Securities included on a Registration Statement and such Registrable Securities remain
Registrable Securities following such transfer, at the request of such Holder, Triangle shall amend or supplement such Registration
Statement as may be necessary in order to enable such transferee to offer and sell such Registrable Securities pursuant to such
Registration Statement; provided that in no event shall Triangle be required to file a post-effective amendment to the Registration
Statement unless (A) such Registration Statement includes only Registrable Securities held by the Holder, Affiliates of the Holder
or transferees of the Holder or (B) Triangle has received written consent therefor from whom Registrable Securities have been registered
on (but not yet sold under) such Registration Statement, other than the Holder, Affiliates of the Holder or transferees of the
Holder.

 

(x)            The
rights of the Holders under this Section 2(a) shall terminate at such time that both (A) the number of Registrable Securities
is less than 3% of the number of outstanding shares of Common Stock (determined considering the Convertible Note on an as-converted
basis and as adjusted as provided in the Convertible Note) and (B) such Registrable Securities may be sold or transferred by the
Holder thereof under Rule 144 under the Securities Act without any limitation on the volume or timing.

 

    	7

    	 

    

 

(b)          Piggyback
Registration. 

 

(i)            If
Triangle shall at any time propose to conduct, other than pursuant to any Demand Registration, a public offering of Common Stock
for cash (whether in connection with a public offering of Common Stock by Triangle, a public offering of Common Stock by stockholders,
or both, but excluding an offering relating solely to an employee benefit plan, an offering relating to a transaction on Form S-4
or S-8 or an offering on any registration statement form that does not permit secondary sales), Triangle shall promptly notify
all Holders of such proposal reasonably in advance of (and in any event at least five Business Days before) the commencement of
the offering (the “Piggyback Notice”). The Piggyback Notice shall offer the Holders the opportunity to include
for registration in such Registration Statement the number of Registrable Securities as they may request (a “Piggyback
Registration”). Triangle shall use commercially reasonable efforts to include in each such Piggyback Registration such
Registrable Securities for which Triangle has received written requests within three Business Days after sending the Piggyback
Notice (“Piggyback Request”) for inclusion therein. If a Holder decides not to include all of its Registrable
Securities in any Registration Statement thereafter filed by Triangle, such Holder shall nevertheless continue to have the right
to include any Registrable Securities in any subsequent registration statement or registration statements as may be filed by Triangle
with respect to offerings of Common Stock, all upon the terms and conditions set forth herein.

 

(ii)            If
the Registration Statement under which Triangle gives notice under this Section 2(b) is for an underwritten offering, Triangle
shall so advise the Holders of Registrable Securities. In such event, the right of any such Holder to be included in a registration
pursuant to this Section 2(b) shall be conditioned upon such Holder’s participation in such underwriting and the inclusion
of such Holder’s Registrable Securities in the underwriting to the extent provided herein. All Holders proposing to distribute
their Registrable Securities through such underwriting shall enter into an underwriting agreement in customary form with the underwriter
or underwriters selected for such underwriting by Triangle. If the managing underwriter or managing underwriters of such
offering advise Triangle and the Holders in writing that in their reasonable opinion that the inclusion of all of the Holders’
Registrable Securities in the subject Registration Statement (or any other Common Stock proposed to be included in such offering)
would likely have an adverse effect in any material respect on the price, timing or distribution of Common Stock proposed to be
included in such offering, Triangle shall include in such offering only that number of shares of Common Stock proposed to be included
in such offering that, in the reasonable opinion of the managing underwriter or managing underwriters, will not have such effect,
with such number to be allocated as follows: (i) first, to Triangle, (ii) if there remains availability for additional shares of
Common Stock to be included in such registration, second pro-rata among all Holders desiring to register Registrable Securities
based on the number of Registrable Securities such Holder is entitled to include in such registration and, if applicable, to any
other holders on whose behalf Triangle filed such Registration Statement and (iii) if there remains availability for additional
shares of Common Stock to be included in such registration, third pro-rata among all other holders of Common Stock who may be seeking
to register such Common Stock based on the number of Common Stock such holder is entitled to include in such registration. If any
Holder disapproves of the terms of any such underwriting, such Holder may elect to withdraw therefrom by written notice to Triangle
and the managing underwriter(s) delivered on or prior to the time of the commencement of such offering. Any Registrable Securities
withdrawn from such underwriting shall be excluded and withdrawn from the registration.

 

    	8

    	 

    

 

(iii)            Triangle
shall have the right to terminate or withdraw any registration initiated by it under this Section 2(b) at any time in its
sole discretion whether or not any Holder has elected to include Registrable Securities in such Registration Statement. The registration
expenses of such withdrawn registration shall be borne by Triangle in accordance with Section 4 hereof. 

 

(iv)            The rights of the Holders under
this Section 2(b) shall terminate if the number of Registrable Securities is less than 5% of the number of outstanding shares
of Common Stock (determined considering the Convertible Note on an as-converted basis and as adjusted as provided in the Convertible
Note).

  

3.           Registration
Procedures.

 

The procedures to be
followed by Triangle and each Holder electing to sell Registrable Securities in a Registration Statement pursuant to this Agreement,
and the respective rights and obligations of Triangle and such Holders, with respect to the preparation, filing and effectiveness
of such Registration Statement, are as follows:

 

(a)            in connection
with a Demand Registration, Triangle will at least two Business Days prior to the anticipated filing of the Registration Statement
and any related Prospectus or any amendment or supplement thereto (other than, after effectiveness of the Registration Statement,
any filing made under the Exchange Act that is incorporated by reference into the Registration Statement), (i) furnish to such
Holders copies of all such documents prior to filing and (ii) use commercially reasonable efforts to address in each such document
when so filed with the Commission such comments as such Holders reasonably shall propose prior to the filing thereof.

 

(b)            in connection
with a Piggyback Registration, Triangle will at least two days prior to the anticipated filing of the initial Registration Statement
that identifies the Holders and any related Prospectus or any amendment or supplement thereto (other than amendments and supplements
that do not materially alter the previous disclosure or do nothing more than name Holders and provide information with respect
thereto), (i) furnish to such Holders copies of all Registration Statements that identify the Holders and any related Prospectus
or any amendment or supplement thereto (other than amendments and supplements that do not materially alter the previous disclosure
or do nothing more than name Holders and provide information with respect thereto) prior to filing and (ii) use commercially reasonable
efforts to address in each such document when so filed with the Commission such comments as such Holders reasonably shall propose
prior to the filing thereof.

 

    	9

    	 

    

 

(c)            Triangle
will use commercially reasonable efforts to as promptly as reasonably practicable (i) prepare and file with the Commission such
amendments, including post-effective amendments, and supplements to each Registration Statement and the Prospectus used in connection
therewith as may be necessary under applicable law to keep such Registration Statement continuously effective with respect to
the disposition of all Registrable Securities covered thereby for its Effectiveness Period and, subject to the limitations contained
in this Agreement, prepare and file with the Commission such additional Registration Statements in order to register for resale
under the Securities Act all of the Registrable Securities held by the Holders; (ii) cause the related Prospectus to be amended
or supplemented by any required prospectus supplement, and as so supplemented or amended to be filed pursuant to Rule 424; and
(iii) respond to any comments received from the Commission with respect to each Registration Statement or any amendment thereto
and, as promptly as reasonably practicable provide such Holders true and complete copies of all correspondence from and to the
Commission relating to such Registration Statement that pertains to such Holders as selling Holders but not any comments that
would result in the disclosure to such Holders of material and non-public information concerning Triangle.  

 

(d)            Triangle
will comply in all material respects with the provisions of the Securities Act and the Exchange Act with respect to the Registration
Statements and the disposition of all Registrable Securities covered by each Registration Statement.

 

(e)            Triangle
will notify such Holders who are included in a Registration Statement as promptly as reasonably practicable: (i)(A) when a Prospectus
or any prospectus supplement or post-effective amendment to a Registration Statement in which such Holder is included has been
filed; (B) when the Commission notifies Triangle whether there will be a “review” of such Registration Statement and
whenever the Commission comments in writing on such Registration Statement (in which case Triangle shall provide true and complete
copies thereof and all written responses thereto to each of such Holders that pertain to such Holders as selling Holders); and
(C) with respect to each such Registration Statement or any post-effective amendment thereto, when the same has been declared effective;
(ii) of any request by the Commission or any other federal or state governmental authority for amendments or supplements to such
Registration Statement or Prospectus or for additional information that pertains to such Holders as sellers of Registrable Securities;
(iii) of the issuance by the Commission of any stop order suspending the effectiveness of such Registration Statement covering
any or all of the Registrable Securities or the initiation of any Proceedings for that purpose; (iv) of the receipt by Triangle
of any notification with respect to the suspension of the qualification or exemption from qualification of any of the Registrable
Securities for sale in any jurisdiction, or the initiation or threatening of any Proceeding for such purpose; and (v) of the occurrence
of any event or passage of time that makes any statement made in such Registration Statement or Prospectus or any document incorporated
or deemed to be incorporated therein by reference untrue in any material respect or that requires any revisions to such Registration
Statement, Prospectus or other documents so that, in the case of such Registration Statement or the Prospectus, as the case may
be, it will not contain any untrue statement of a material fact or omit to state any material fact required to be stated therein
or necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading (provided,
however, that no notice by Triangle shall be required pursuant to this clause (v) in the event that Triangle either
promptly files a prospectus supplement to update the Prospectus or a Form 8-K or other appropriate Exchange Act report that is
incorporated by reference into the Registration Statement, which in either case, contains the requisite information that results
in such Registration Statement no longer containing any untrue statement of material fact or omitting to state a material fact
necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading).

 

    	10

    	 

    

 

(f)            Triangle
will use commercially reasonable efforts to avoid the issuance of, or, if issued, obtain the withdrawal of (i) any order suspending
the effectiveness of a Registration Statement, or (ii) any suspension of the qualification (or exemption from qualification) of
any of the Registrable Securities for sale in any jurisdiction, as promptly as reasonably practicable, or if any such order or
suspension is made effective during any Blackout Period or Suspension Period, as promptly as reasonably practicable after such
Blackout Period or Suspension Period is over. 

 

(g)            During
the Effectiveness Period, Triangle will furnish to each such Holder, without charge, at least one conformed copy of each Registration
Statement and each amendment thereto and all exhibits to the extent requested by such Holder (including those incorporated by reference)
promptly after the filing of such documents with the Commission; provided, that Triangle will not have any obligation to
provide any document pursuant to this clause that is available on the Commission’s EDGAR system.

 

(h)            Triangle
will promptly deliver to each Holder, without charge, as many copies of each Prospectus or Prospectuses (including each form of
prospectus) authorized by Triangle for use and each amendment or supplement thereto as such Holder may reasonably request during
the Effectiveness Period. Subject to the terms of this Agreement, including Section 7(b), Triangle consents to the use of
such Prospectus and each amendment or supplement thereto by each of the selling Holders in connection with the offering and sale
of the Registrable Securities covered by such Prospectus and any amendment or supplement thereto.

 

(i)            Triangle
will cooperate with such Holders to facilitate the timely preparation and delivery of certificates representing Registrable Securities
to be delivered to a transferee pursuant to a Registration Statement, which certificates shall be free of all restrictive legends
indicating that the Registrable Securities are unregistered or unqualified for resale under the Securities Act, Exchange Act or
other applicable securities laws, and to enable such Registrable Securities to be in such denominations and registered in such
names as any such Holder may request in writing. In connection therewith, if required by Triangle’s transfer agent, Triangle
will promptly, after the Effective Date of the Registration Statement, cause an opinion of counsel as to the effectiveness of the
Registration Statement to be delivered to and maintained with its transfer agent, together with any other authorizations, certificates
and directions required by the transfer agent which authorize and direct the transfer agent to issue such Registrable Securities
without any such legend upon sale by the Holder of such Registrable Securities under the Registration Statement.

 

(j)            Upon the
occurrence of any event contemplated by Section 3(e)(v), subject to Section 2(a)(iv) and this Section 3(j),
as promptly as reasonably practicable, Triangle will prepare a supplement or amendment, including a post-effective amendment, if
required by applicable law, to the affected Registration Statement or a supplement to the related Prospectus or any document incorporated
or deemed to be incorporated therein by reference, and file any other required document so that, as thereafter delivered, no Registration
Statement nor any Prospectus will contain an untrue statement of a material fact or omit to state a material fact required to be
stated therein or necessary to make the statements therein, in the light of the circumstances under which they were made, not misleading.

 

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(k)            Such
Holders may distribute the Registrable Securities by means of an underwritten offering; provided that (i) in the case
of a Demand Registration, (A) the Initiating Holder provides written notice to Triangle of its intention to distribute Registrable
Securities by means of an underwritten offering, which for the avoidance of doubt may be made at a date later than the original
Demand Notice (the “Underwritten Offering Notice” and such underwritten offering being referred to herein as
an “Underwritten Offering”) and (B) Holders (including the Initiating Holder) having an aggregate value of at
least $30 million based on the VWAP of such Registrable Securities as of the date of such Underwritten Offering Notice desire to
participate in such Underwritten Offering and, in the case of a Piggyback Registration, the electing Holders must include their
Registrable Securities in an underwritten offering if the Piggyback Notice so requires, (ii) the right of any Holder to include
such Holder’s Registrable Securities in such registration shall be conditioned upon such Holder’s participation in
such underwriting and the inclusion of such Holder’s Registrable Securities in the underwriting to the extent provided herein,
(iii) the managing underwriter or managing underwriters thereof shall be designated by the Initiating Holder in the case of a Demand
Registration (provided, however, that such designated managing underwriter or managing underwriters shall be reasonably
acceptable to Triangle) or by Triangle in the case of a registration initiated by Triangle, (iv) each Holder participating in such
underwritten offering agrees to enter into an underwriting agreement in customary form and sell such Holder’s Registrable
Securities on the basis provided in any underwriting arrangements approved by the Persons entitled to select the managing underwriter
or managing underwriters hereunder and (v) each Holder participating in such underwritten offering completes and executes all questionnaires,
powers of attorney, indemnities, underwriting agreements and other documents reasonably required under the terms of such underwriting
arrangements. Triangle hereby agrees with each Holder that, in connection with any Underwritten Offering in accordance with the
terms hereof, it will negotiate in good faith and execute all indemnities, underwriting agreements and other documents reasonably
required under the terms of such underwriting arrangements, including using all commercially reasonable efforts to procure customary
legal opinions and auditor “comfort” letters. Notwithstanding the foregoing, Triangle is not obligated to effect
more than (A) one Underwritten Offering in any 12 month period and (B) a total of three Underwritten Offering pursuant to this
Agreement. If, in the case of an Underwritten Offering, the managing underwriter advises Triangle that the inclusion of all of
the Holders’ Registrable Securities in the subject Underwritten Offering would likely have an adverse effect in any material
respect on the price, timing or distribution of Registrable Securities proposed to be included in such Underwritten Offering, then
Triangle shall so advise all Holders of Registrable Securities that would otherwise be underwritten pursuant hereto, and the number
of Registrable Securities that may be included in the Underwritten Offering shall be allocated to the Holders of such Registrable
Securities on a pro rata basis based on the number of Registrable Securities held by all such Holders (including the Initiating
Holders). Any Registrable Securities excluded or withdrawn from such Underwritten Offering shall be withdrawn from the Underwritten
Offering. In the event that the managing underwriter limits the number of Registrable Securities to be included in the Underwritten
Offering pursuant to this Section 3(k) such that at least two-thirds of the aggregate Registrable Securities set forth in
such Holders’ written requests pursuant to this Section 3(k) are included in the Underwritten Offering, such Underwritten
Offering shall not be considered to be an Underwritten Offering for purposes of the limitations set forth in this Section 3(k).

 

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(l)            In the
event such Holders seek to complete an Underwritten Offering, for a reasonable period prior to the filing of any Registration Statement
and throughout the Effectiveness Period, Triangle will make available upon reasonable notice at Triangle’s principal place
of business or such other reasonable place for inspection during normal business hours by the managing underwriter or managing
underwriters selected in accordance with Section 3(k) such financial and other information and books and records of Triangle,
and cause the officers, employees, counsel and independent certified public accountants of Triangle to respond to such inquiries,
as shall be reasonably necessary (and in the case of counsel, not violate an attorney-client privilege in such counsel’s
reasonable belief) to conduct a reasonable investigation within the meaning of Section 11 of the Securities Act.

 

(m)            In connection
with any Demand Registration, Triangle will use commercially reasonable efforts to cause appropriate officers and employees to
be available, on a customary basis and upon reasonable notice, to meet with prospective investors in presentations, meetings and
road shows.

 

(n)            Triangle
may require the Holder to furnish to Triangle any other information regarding the Holder and the distribution of such securities
as Triangle reasonably determines is required to be included in any Registration Statement.

 

4.            Registration
Expenses. All Registration Expenses incident to the Parties’
performance of or compliance with their respective obligations under this Agreement or otherwise in connection with any Demand
Registration or Piggyback Registration (in each case, excluding any Selling Expenses) shall be borne by Triangle, whether or not
any Registrable Securities are sold pursuant to a Registration Statement. “Registration Expenses” shall include,
without limitation, (i) all registration and filing fees (including fees and expenses (A) with respect to filings required to
be made with the Trading Market and (B) in compliance with applicable state securities or “Blue Sky” laws), (ii) printing
expenses (including expenses of printing certificates for Triangle Securities and of printing prospectuses if the printing of
prospectuses is reasonably requested by a Holder of Registrable Securities included in the Registration Statement), (iii) messenger,
telephone and delivery expenses, (iv) fees and disbursements of counsel, auditors and accountants for Triangle, (v) Securities
Act liability insurance, if Triangle so desires such insurance, (vi) fees and expenses of all other Persons retained by Triangle
in connection with the consummation of the transactions contemplated by this Agreement and (vii) all expenses relating to marketing
the sale of the Registrable Securities, including expenses related to conducting a “road show.” In addition, Triangle
shall be responsible for all of its expenses incurred in connection with the consummation of the transactions contemplated by
this Agreement (including expenses payable to third parties and including all salaries and expenses of their officers and employees
performing legal or accounting duties), the expense of any annual audit and the fees and expenses incurred in connection with
the listing of the Registrable Securities on the Trading Market. 

 

    	13

    	 

    

 

5.            Indemnification.

 

(a)            Triangle
shall indemnify and hold harmless each Holder, its Affiliates and each of their respective officers and directors and any Person
who controls any such Holder (within the meaning of the Securities Act) and any agent thereof (collectively, “Holder Indemnified
Persons”), to the fullest extent permitted by applicable law, from and against any and all losses, claims, damages, liabilities,
joint or several, costs (including reasonable costs of preparation and reasonable attorneys’ fees) and expenses, judgments,
fines, penalties, interest, settlements or other amounts arising from any and all claims, demands, actions, suits or proceedings,
whether civil, criminal, administrative or investigative, in which any Indemnified Person may be involved, or is threatened to
be involved, as a party or otherwise, under the Securities Act or otherwise (collectively, “Losses”), as incurred,
arising out of or relating to any untrue or alleged untrue statement of a material fact contained in any Registration Statement
under which any Registrable Securities were registered, in any preliminary prospectus (if Triangle authorized the use of such preliminary
prospectus prior to the Effective Date), or in any summary or final prospectus or free writing prospectus (if such free writing
prospectus was authorized for use by Triangle) or in any amendment or supplement thereto (if used during the period Triangle is
required to keep the Registration Statement current), or arising out of, based upon or resulting from the omission or alleged omission
to state therein a material fact required to be stated therein or necessary to make the statements made therein, in the light of
the circumstances in which they were made, not misleading; provided, however, that Triangle shall not be liable
to any Holder Indemnified Person to the extent that any such claim arises out of, is based upon or results from an untrue or alleged
untrue statement or omission or alleged omission made in such Registration Statement, such preliminary, summary or final prospectus
or free writing prospectus or such amendment or supplement, in reliance upon and in conformity with written information furnished
to Triangle by or on behalf of such Holder Indemnified Person or any underwriter specifically for use in the preparation thereof.
Triangle shall notify the Holders promptly of the institution, threat or assertion of any Proceeding of which Triangle is aware
in connection with the transactions contemplated by this Agreement. Notwithstanding anything to the contrary herein, this
Section 5 shall survive any termination or expiration of this Agreement indefinitely.

 

(b)            In connection with any Registration
Statement in which a Holder participates, such Holder shall indemnify and hold harmless Triangle, its Affiliates and each of their
respective officers, directors and any Person who controls Triangle (within the meaning of the Securities Act) and any agent thereof
(collectively, the “Triangle Indemnified Persons”), to the fullest extent permitted by applicable law, from
and against any and all Losses as incurred, arising out of or relating to any untrue or alleged untrue statement of a material
fact contained in any such Registration Statement, in any preliminary prospectus (if used prior to the Effective Date of such Registration
Statement), or in any summary or final prospectus or free writing prospectus or in any amendment or supplement thereto (if used
during the period Triangle is required to keep the Registration Statement current), or arising out of, based upon or resulting
from the omission or alleged omission to state therein a material fact required to be stated therein or necessary to make the statements
made therein, in the light of the circumstances in which they were made, not misleading, but only to the extent that the same are
made in reliance and in conformity with information relating to the Holder furnished in writing to Triangle by such Holder for
use therein.

 

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(c)            Any Person entitled to indemnification
hereunder shall (i) give prompt written notice to the indemnifying party of any claim with respect to which it seeks indemnification
and (ii) unless in such indemnified party's reasonable judgment a conflict of interest between such indemnified and indemnifying
parties may exist with respect to such claim or there may be reasonable defenses available to the indemnified party that are different
from or additional to those available to the indemnifying party, permit such indemnifying party to assume the defense of such claim
with counsel reasonably satisfactory to the indemnified party. If such defense is assumed, the indemnifying party shall not be
subject to any liability for any settlement made by the indemnified party without its consent (but such consent will not be unreasonably
withheld). An indemnifying party who is not entitled to, or elects not to, assume the defense of a claim shall not be obligated
to pay the fees and expenses of more than one counsel (in addition to any local counsel) for all parties indemnified by such indemnifying
party with respect to such claim, unless in the reasonable judgment of any indemnified party there may be one or more legal or
equitable defenses available to such indemnified party that are in addition to or may conflict with those available to another
indemnified party with respect to such claim. Failure to give prompt written notice shall not release the indemnifying party from
its obligations hereunder. 

  

6.            Facilitation
of Sales Pursuant to Rule 144. To the extent it shall be required
to do so under the Exchange Act, Triangle shall timely file the reports required to be filed by it under the Exchange Act or the
Securities Act (including the reports under Sections 13 and 15(d) of the Exchange Act referred to in subparagraph (c)(1) of Rule
144), and shall take such further action as any Holder may reasonably request, all to the extent required from time to time to
enable the Holders to sell Registrable Securities without registration under the Securities Act within the limitations of the
exemption provided by Rule 144. Upon the request of any Holder in connection with that Holder’s sale pursuant to Rule
144, Triangle shall deliver to such Holder a written statement as to whether it has complied with such requirements.

 

7.            Miscellaneous.

 

(a)            Remedies.
In the event of a breach by Triangle of any of its obligations under this Agreement, each Holder, in addition to being entitled
to exercise all rights granted by law and under this Agreement, including recovery of damages, will be entitled to specific performance
of its rights under this Agreement. Triangle agrees that monetary damages would not provide adequate compensation for any losses
incurred by reason of a breach by it of any of the provisions of this Agreement and further agrees that, in the event of any action
for specific performance in respect of such breach, it shall waive the defense that a remedy at law would be adequate.

 

(b)            Discontinued
Disposition. Each Holder agrees that, upon receipt of a notice from Triangle of the occurrence of any event of the kind described
in clauses (ii) through (v) of Section 3(e) (a "Suspension Notice"), such Holder will forthwith discontinue
disposition of such Registrable Securities under the Registration Statement until such Holder’s receipt of the copies of
the supplemental Prospectus or amended Registration Statement as contemplated by Section 3(j) or until it is advised in
writing by Triangle that the use of the applicable Prospectus may be resumed, and, in either case, has received copies of any additional
or supplemental filings that are incorporated or deemed to be incorporated by reference in such Prospectus or Registration Statement
(a “Suspension Period”).  Triangle may provide appropriate stop orders to enforce the provisions of this
Section 7(b).

 

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(c)            Amendments
and Waivers. No provision of this Agreement may be waived or amended except in a written instrument signed by Triangle and
Holders that hold a majority of the Registrable Securities as of the date of such waiver or amendment. Triangle shall provide prior
notice to all Holders of any proposed waiver or amendment. No waiver of any default with respect to any provision, condition or
requirement of this Agreement shall be deemed to be a continuing waiver in the future or a waiver of any subsequent default or
a waiver of any other provision, condition or requirement hereof, nor shall any delay or omission of any Party to exercise any
right hereunder in any manner impair the exercise of any such right.

 

(d)            Notices.
Any and all notices or other communications or deliveries required or permitted to be provided hereunder shall be in writing and
shall be deemed given and effective on the earliest of (i) the date of transmission, if such notice or communication is delivered
via facsimile or electronic mail as specified in this Section 7(d) prior to 5:00 p.m. (Denver Time) on a Business Day, (ii)
the Business Day after the date of transmission, if such notice or communication is delivered via facsimile or electronic mail
as specified in this Agreement later than 5:00 p.m. (Denver Time) on any date and earlier than 11:59 p.m. (Denver Time) on such
date, (iii) the Business Day following the date of mailing, if sent by nationally recognized overnight courier service or (iv)
upon actual receipt by the Party to whom such notice is required to be given. The address for such notices and communications shall
be as follows:

 

	 	If to Triangle:	 	Triangle Petroleum Corporation
	 	 	 	Attention: Justin Bliffen
	 	 	 	1200 17th Street, Suite 2600
	 	 	 	Denver, Colorado 80202
	 	 	 	Fax: (303) 260-5080
	 	 	 	Electronic mail: jbliffen@trianglepetroleum.com
	 	 	 	 
	 	If to the Purchaser or any of its Affiliates:	 	c/o Natural Gas Partners
	 	 	 	Attention: Craig Glick
	 	 	 	125 E. John Carpenter Fwy., Suite 600
	 	 	 	Irving, Texas 75062
	 	 	 	Fax: (972) 432-1441
	 	 	 	Electronic mail: cglick@ngptrs.com
	 	 	 	 
	 	If to any other Person who is then the registered Holder:	 	To the address of such Holder as it appears in the applicable register for the Registrable Securities or such other address as may be designated in writing hereafter, in the same manner, by such Person.

 

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(e)            Successors
and Assigns. This Agreement shall be binding upon and inure to the benefit of the Parties hereto and their heirs, executors,
administrators, successors, legal representatives and permitted assigns. Except as provided in this Section 7(e), this Agreement,
and any rights or obligations hereunder, may not be assigned without the prior written consent of Triangle and the Purchaser. Notwithstanding
anything in the foregoing to the contrary, the registration rights of a Holder pursuant to this Agreement with respect to all or
any portion of its Registrable Securities may be assigned without such consent (but only with all related obligations) with respect
to such Registrable Securities (and any Registrable Securities issued as a dividend or other distribution with respect to, in exchange
for or in replacement of such Registrable Securities) by such Holder to a transferee of such Registrable Securities; provided
(i) Triangle is, within a reasonable time after such transfer, furnished with written notice of the name and address of such transferee
or assignee and the Registrable Securities with respect to which such registration rights are being assigned and (ii) such
transferee or assignee agrees in writing to be bound by and subject to the terms set forth in this Agreement. Triangle may not
assign its respective rights or obligations hereunder without the prior written consent of the Purchaser.

 

(f)            Third
Party Beneficiaries. Other than the Holders (other than the Purchaser), there are no third party beneficiaries having rights
under or with respect to this Agreement.

 

(g)            Execution
and Counterparts. This Agreement may be executed in any number of counterparts, each of which when so executed shall be deemed
to be an original and all of which taken together shall constitute one and the same Agreement. In the event that any signature
is delivered by facsimile or electronic mail transmission, such signature shall create a valid binding obligation of the Party
executing (or on whose behalf such signature is executed) the same with the same force and effect as if such signature delivered
by facsimile or electronic mail transmission were the original thereof.

 

(h)            Governing
Law; Consent to Jurisdiction; Waiver of Jury Trial. This Agreement shall be governed by, and construed in accordance with,
the internal laws of the State of New York, without reference to the choice of law provisions thereof. Each of the Parties irrevocably
submits to the exclusive jurisdiction of the courts of the State of New York located in in the Borough of Manhattan in the City
of New York and the United States District Court for the Southern District of New York for the purpose of any suit, action, proceeding
or judgment relating to or arising out of this Agreement and the transactions contemplated hereby. Service of process in connection
with any such suit, action or proceeding may be served on each Party anywhere in the world by the same methods as are specified
for the giving of notices under this Agreement. Each of the Parties irrevocably waives any objection to the laying of venue of
any such suit, action or proceeding brought in such courts and irrevocably waives any claim that any such suit, action or proceeding
brought in any such court has been brought in an inconvenient forum. EACH OF THE PARTIES HEREBY WAIVES ANY RIGHT TO REQUEST
A TRIAL BY JURY IN ANY LITIGATION WITH RESPECT TO THIS AGREEMENT AND REPRESENTS THAT COUNSEL HAS BEEN CONSULTED SPECIFICALLY AS
TO THIS WAIVER.

 

(i)            Cumulative
Remedies. The remedies provided herein are cumulative and not exclusive of any remedies provided by law.

 

    	17

    	 

    

 

(j)            Severability.
If any term, provision, covenant or restriction of this Agreement is held by a court of competent jurisdiction to be invalid, illegal,
void or unenforceable, the remainder of the terms, provisions, covenants and restrictions set forth herein shall remain in full
force and effect and shall in no way be affected, impaired or invalidated, and the Parties shall use their reasonable efforts to
find and employ an alternative means to achieve the same or substantially the same result as that contemplated by such term, provision,
covenant or restriction.  It is hereby stipulated and declared to be the intention of the Parties that they would have executed
the remaining terms, provisions, covenants and restrictions without including any of such that may be hereafter declared invalid,
illegal, void or unenforceable.

 

(k)            Entire
Agreement. This Agreement constitutes the entire agreement among the Parties with respect to the subject matter hereof and
supersedes all prior contracts or agreements with respect to the subject matter hereof and the matters addressed or governed hereby,
whether oral or written.

 

[THIS SPACE LEFT BLANK INTENTIONALLY]

 

    	18

    	 

    

 

IN WITNESS WHEREOF, the Parties have executed
this Agreement as of the date first written above.

 

	 	TRIANGLE PETROLEUM CORPORATION
	 	 	 
	 	By:	/s/ Jonathan Samuels
	 	Name: 	Jonathan Samuels
	 	Title:	President and Chief Executive Officer
	 	 	 
	 	NGP TRIANGLE HOLDINGS, LLC
	 	 
	 	By:	NGP Natural Resources X, L.P., its managing member
	 	 	 
	 	By:	G.F.W. Energy X, L.P., its general partner
	 	 	 
	 	By:	GFW X, L.L.C., its general partner
	 	 	 
	 	By:	/s/ Kenneth A. Hersh
	 	Name:	Kenneth A. Hersh
	 	Title:	Authorized Member

  

Signature Page to Registration Rights
Agreement

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