/ 

,ffTS 16039;,1' O.M.B. No. 2070-0012: 3 

t1 &EPA United States 

Environmental Protection 

Agency 

PREMANUFACTURE NOTICE 

FOR NEW CHEMICAL SUBSTANCES 

AGENCY USE ONLY 

Oltte of receipt 

DTS 

When 

completed 

send this 

form to 

DOCUMENT CONTROL OFFICER 

OFFICE OF TOXIC SUBSTANCES. T$-793 

U.S. E.P.A. 

401 M STREET, SW 

WASHINGTON, D.C. 20460 

I. Enter the total numbw of pages !~ in the Pra...-nutacture Notice 17 

GENERAL IIISTRUCTIONS 

Vou must provide all information requested in tlllis fo•m n~ 1111e extent Uhat ill: is known t(l) CDr~ 

ascertainable by you. Make reasonable estimates if you do lOOt haw aett&llill cdata. 

Befo•e you complete this form, you should reed the "tlllSti!UCtions ~ tCDr P1'811'Aal'llli>facture Notification" 

llnetluctlona Menuell. 

P_.l - GENERAL INFORMATION 

You must provide the chemicat identity of the new chemical 

substance. even if you claim the identity as confidential. You may 

authorize another person- to submft the identity for you, but your 

submission will not be complete and review will not begin until 

EPA receives this information. 

P_.ll- HUMAN EXPOSURE AND ENVIRONMENTAL 

RELEASE 

You may need addi1ional copies of pert II, sections A and B if there 

are save•al manufacture, processing, or usa operations that you 

will describe in the notice. You should reproduce these sections 

as needed. 

"P_.lll- LIST OF ATTACHMENTS 

You should attach addi1ional sheets if you do not have enough 

space on the form to answer a question fully. In pert Ill, list these 

attachments, any test data or other data, and any optional 

information that you include in the notice. 

OP'YIONAL INFORMATION 

You may include in the notice any information that you want EPA 

to 

M8nUIII 

consider 

identifies 

in evaluating 

categories 

the new 

of optional 

substance. 

information 

The ~ 

that you may 

want EPA to review. 

CONFIDENTIALITY CLAIMS 

You may claim any information in this notice as confidential'. 1\'o 

assart a claim on the form, mark IX) the confidential box nelrt to 

the information that you claim as confidentiat. To assert a claim· inan attachment, circle or bracket the infonmnion you claim as confidential. If you claim information ifl the notice as confidential<, 

you must provide a sanitized version of the- notice, including; 

attachments, to EPA with your submission. For additional 

instructions on claiming information- a& confidential~ readlthelnstructlona M ........ 

Indicate betow the categofies of information you have• claimed Ia& 

confidential ifl the notice and th& type· of notice. 

1 0 SUBMmER IDENJiiFY 

2 0 CHEMICAL IDENJ~'FY 

3 ~ PRODUCTION VOI!.UME 

4 0 USE INFORMATION< 

50 PROCESS INFORMATION 

6 0 PORTIONS OF A MtX'li'URE 

7 0 OTHER INFORMATION 

EPA Form 7710.2& (•12-18-Mt 

fXl PMN' 

0TMEA 

OsNt:JR 

0 ExemptiEm -

Speci#y ~ 

TEST DATA A.a OTMER DATA 

You •e required tG II1Ubmit all test data iA your possession Of c0!'11irol 

and to provide a clescriptiol'l of all oti'ler data known to or reasonably 

ascertainable by you i<f these data are related to the health and 

environmental effects of the manutactu~e. processing, distribution 

in corn~rce, use. or disposal of the new chemical substance. 

Standard literature citations mB¥ l!le submitted for data in the open 

scientific literature. Comptete test cdata, !'lOt summaries of data, 

must be submit~oed if they do not appear iA the open literature. 

Following •• exa~nptes of test data and other data. You should 

submit tMS8 data according to the r~~nts of §720.50 of the 

Premanuf!IC't\M'e NotificMion Rule (40 CFR Part 720). 

T_. ... 

• Elw.,••aitaltaeectMa 

~~ ~U'V, visib6e, and infrared) 

Del'lsity of liQutcts and solids 

WlJier so~w~Ditity 

MehilllfJ JIIC!)illlltlmelting range 

Boilil'lg JIICI)int/boiing range 

v.,.,.. (11118SSW1'8 

PartlhiGMn cC!IefflicieAt, 1'1-octanoMwatl!el' 

.,_,aGatiolll 

Hy0.flll¥sis (.as a fwnctiol'l of pHl) 

Pl!!rottDCirlemical degracialtion 

A~iol!l/desorption to soil types 

DissociMiCI)III CCim&t!JIIllt 

Other (lli!l¥sical1 cf!lemical IIJII'opel"ties 

................. Mwl!agenicity 

CBI!ciiiiC!lfJenicity 

T 8f!llt(l)genicity 

Ac~~rte toxicity 

llletDeated dose to~ticit.y 

Metaeolism studies 

Sensitization 

ht~itation 

. .............. ,....,.. ..... Microbial and algal to~tici<tly 

Telll'88trial vascular plant to~Gicity (e.fB-, seeal ~"' 

se~:~dles, growth inhibft!iGnl Ac~:~te and•chronic to~icitty to...,... (e.g., fisn, twda, 

mammals, invarteb~81!8S) 

• Nell auu1ment. 

e thructiiJI/ectivity •IIIIi I ftlhipta 

• T_. ... not· in, the 11111 a a liiMl or control of the tulanittel 
:-' . 

' CERTIFICATION 

! 

1 certify that to the best of my knowledge and belief: 

1 • The company named in part I, section A, subsection 1a of tlllis notice form intends to m81'11itfacture « import for a 

commercial purpose, other than in small quantities sotely for 'ese8Jich and deYelopmef'llt, the substance iden>tifiecll 

in part I. section B. 

2. AU information provided in this notice is complete and ti'Uihtul as of 1lrle ctete of submission. 

3. I am submitting with this notice aft test data in my PQSSeSSien er c~ and a description of all other data knowm 

to « reasonably ascertainable by me as required by i 720. 50 of 1M fl'remMufac:ture Notification Rule. 

(S}(i) The company named in Part I, Section A has remitted the fee specified 

in 40 CFR 700.45 (b). ~ 

c~ 

• 

Signature of authorized official 0.. 

11~t'1U /J tt~/eu $-j~ ·f9 

Signature of agenf l-Ift v I Date 

Part I - GENERAL INFORMATION 

~ Section A - SUBMITTER IDENTIFICATION C4 

Merle tXJ the "Confldentilll'' box next to any subMction you clam as confldemial. • 

1e. Person Name of authorized official Titte 

submitting Peggy J. Vince Dir Reg & Environ Affairs notice 

Company 

••••••• 

She rex Chemical Company 

Mailing address (number and street) 

5777 Frantz Road 

City, State, ZIP code 

Dublin. Ohio 43017 

b. Agentlif Name of authorized official Titte 

appficable) 

Company tr 

\ 

Mailing address lnumber and street) ••••• • 

/ 

City, State, ZIP code .< 

c. "you are submitting this notice as Plll't of a joint submissifm, mMt (X) this box. 0 

2. Technical Name Ttitle 

contact Howard M. Hickman President 

Company ; Hickman Assoicates. Inc. 

Mailing address lnumber and street) • 

596 Whitney Ave. • 

City, State, 21P cod& I Area code I Number 

Worthinaton. Ohio 43085 lielephone : 6 14 I 888-6765 

3. If you have had: a prenotice communication ~PC) cGnCerning: this notic:e and EPA Msrlt. I )(IJ .IX] assigned' a· PC Number to the notice, enter the IWmber if none--+ 

4. If you have submitted· a- test-marketing exemption (TME) 8J!Piicati4m for 1he chemical Mark()(,) substance covered by this notice, enter the TME number assigflled by EPA if none ----+ IX] 

s. If you have submitted & bona fide request few the chemic.t substance C0¥8I'8d by M8l'lt (X) !Xl this notice, enter the bona fide request number assigned by EPA if I'IIOne ----+ 

•• Type of Notice - Matt (XI 0 Manufacture [[I Import 

FORM EPA-7710.251·12·18-IMI Page 2 
~ ' Part I- GENERAL INFORMATION- Continued 

·~ Section 8- CHEMICAL IDENTITY INFORMATION 

Marlc (XJ the "Confident;.#" box neJrt to any item you claim n comi<:JenNI. 

co......-. Dither ltom1 or 2 u epproprlete. Ce!lllll .... dother ltelno. r--

H 8fl0ther person will submit chemical identity information for you, mal'k (XI tllle box at the right. D Co 

Identify the name, company. and address of that person in a continualio~~t sheet. ... 1 • C.._ 1 er 2 c:Mmlc.a ~ {for definitions of class 1 and class 2 swD&ta~~~ces, see 11rte I ..... IIICtlefta ......_., 

o. Class of substance - Marlf. (XJ ri] Claas1 no.s2 

b. Chemical name lpreferably CAS or IUPAC nomenclature) 

Oxirane, 2,2'-[1,6-hexanediylbis(oxymethylene)bis] 

CAS# 16096-31-4 

~ " c. Moleculalr formula and CAS Registry Number Cif known) 

Cl2H2204 

....... 

~ d. For a claea 1 suD&tance, provide a structural diagram. For a class 2 substarlC8 - I 1 I List 1Jole immediate precursor substances with their 

respective CAS Registry Numbers. 121 Describe the nature of the reaction or process. (311Adicate the range of composition and the 

typicat composition I where appropriate). (4) Provide a representative structural diagram (.if possible). ~ 

ll . ll 

H C---cH-CH -0-(CH ) -0-CH -CH--cH 2 2 2 6 2 2 

MMk IXJ this box it you attach a continuation sheet. 

FOAMEPA-7710.25112·l8-M) Page3 

..... 
Part I- GENERAL INFORMATION- Continued 

~ Section B- CHEMICAL IDENTITY INFORMATION- Centinue4 

1 2. Polymers !For a definition of polymer, see the Instructions M ........ ) 

a. Indicate the lowe.t number-average molecular weight composition of the li)Oiymer you il'ftel!lclt t& l!lllal'lliJfactl.ll'e. Indica-te the ..-ximum weight percent of low molecular weight species below 500 and below t,OOO absolute molecllllar weight <X tlhat COITipOSi1!ion. Describe the methods of measurement or the bases for your estimates. 

NA 

0 Mark lXI this box if you attach a contimunion sheet. 

b. You must make separate confidentiality claims for monomer or other react.-t idelllltlirty, c~ion information, and residue~! information. Mark lXI the "Confidential" box next to any item you claim as confidelilltla 

I 1 l - Provide the chemical name and CAS Registry Number of each monomer or other reec:.tam used in the manufacture of 1t1e ~. 121 - Mark CXI this column if entry in column 11 I is confidential. 

131 - Indicate the trPf4* weight percent of e.:h monomer or other reactant in tt. pofymer. 

141 - Mark CXI the identity column if you want a monomer or other reactant used at two weighot percent or less to be listeat as part of the polymer description on the TSCA Chemical Substance Inventory. 

(51 - Mark lXI this column if entries in columns (3) and 14) are confidential. 

(6) - Indicate the maximum weight percent of each monomer or other reactant that may be present as a residual in tt. polymer as manufactured for commercial purposes. 

(7) - Mark lXI this column if entry in column 161 is confidential. 

Monomer or other reactant and CAS Registry Number 

111 

c..ft. Typical Identity CeMII· Maximum 

ompositiorl Mart {X) ........ residual 

(2) 131 (4) (5·1 (6) 

NA % % 

% "' 

% % 

% % 

% % 

% % 

% % 

0 Mark (XJ this box i1 you attach a continuation sheet. 

c. Provide a representative structural diagram of the polymer, if possible. 

I]_ Mark lXI this box i1 you att.:h a continuation sheet. 

FORM EPA-7710-25112-18-841 Page4 

Cc 

-

-

Co 

del 

( 

'•····· 

'---
' . I· Part I- GENERAL INFORMATION -Continued 

I 

~ Section B - CHEMICAL IDENTITY INFORMATION - CoMinued 

3. IIIIPUrtta.. 

(a, - Identity each impurity that may be reasonably anticipated to be Pf'esenl m tllle cl:lemical substance as mal\'lufactured fOI' 

commercial purposes. Provide the CAS Registry Number if aveilab'e. tf 1tlef!e a,e UAkitentitied impurities, enter "unidenti4iied." 

(b, - Estimate the .............. weight percent of each impurity. H there .. unictentitiect imp.JI!;oies, estimate their total weigl!lt perceAt. 

i 

' Malclimum 

I Impurity and CAS Registry Number eo.. 

' 1J1!811Cel'rt .. 

tat (iiJI) 

% X 

" 

" 

% 

" 

" 

% 

Ll Merle (X} this box if you attach • continuation sheet. 

4. SynonJIM - Enter any synonyms for the new chemic* sut1stance identified in subsection 1 or 2. c. 

.. 

-

X 

D Merle (X} this box if you attach • continuation sheet. ~ 1. Trecleldentlflcatlon - Ust trade names for the new chemical substance identified m SlllbsectiiCI)fll 1 Cllt 2. 

DILUENT H 

D Merle (XI this box if you attach • continuation sheet. ' 

\1) 

I. Generic chemlcel ....... -If you claim chemic* identity • cGnlidential, enter the generic chemical neme that you developed wim EPA 

during prenotice communication. tf yw have not developecla generic n.ne with EPA. Pf'OVide a generic name 

that reveals the specifiC chemical identity of the new chernic81 substance to the maximum extent possible. 

Read the TSCA Chemical ~8f1Celnventory, lritiallnventory, VoU'ne I for guidance on~ generic 

names. 

0 Marlc (X} this box if you attach • continuation.,__ 

7. ayproducta -Describe any bypt'oducts ~from 1he INIIUiac:1Ure, proc:eMilrls, lil&e, or disposal·of the AeW cl!llmical substance at 

sites you control. Provide the Registry NumMr if availabte. . 

8yprocluct CAS~Number Cef 

m (2') ..... 

None. The Pmn substanQ~ ia imgct:ted 

0 Marlc f)(' thie box i# you attach • continuation sheet. 

FORM EPA-7710.25 t12·18r-84) PageS 
Part 1- GENERAL INFORMATION- Continued 

~ SectionC- PRODUCTION, IMPORT, AND USE INFORMATION 

Mark (X) the "Confidential" box next to any item you claim liS confidential. 

1 • Production volume - Estimate the maximum production volume during the first 1 2 months of production. Also estimate the 

maximum production volume for any consecutive 12-month period during the first three years of production. c...- ~--------~------------~--------------~--~--~------~----~------------------------~~ ,... first 1" nrntf••~inn (kg/yr) u .. ,; ... ,, ... 1" .-~. ·•~ (kg/yr) 

X 

2 U• You must make separate claims for the .....,-: 'f~ • of the category of use, the percent of production volume delo'cMec to eac1 

categoty, the formulation of the new substance, and other use information. Mart'"'' the "Confidential" box next to any item you claim as con~al. 

a. 11 I - Describe each intended category of use of the new chemical substance by function and application. 

121 - Mark lXI this column if entry in column I 1 I is confidential. 

13) - Estima1e the percent of total production for the first three years devoted to eech category of use. 

141 - Mark tXI this column if entry in column 131 is confidential. 

151 - Estima1e the percent of the new substance as formulated in mixtures, suspensions, emulsions, solutions, or gels as manuf~ 

for commercial purposes at sites under your control associated whtl eech category of use. 

(61 - Mark lXI this column if entry in column (51 is confidential. 

171 - Mark lXI whether the use is site-limited, industrial, commercial, or C~:C~nS~Jmer. Mark more thwl one coU-nn if appropriate. 

181 - Mark lXI this column if entry(ies) in column (7) is (are) confidemial. 

Read the IMtruc:tiontl Manual for examples. 

Category of use 

Reactive diluent for high 

performance epoxy resin 

systems for aerospace. 

[ J Mark IXJ this_ box if you attach a,... ... ; .... --..·-

c.... 

....... 

121 

!i: i' 

.l •••••••• 

b. Generic 

use 

description 

H you cfaim any categOfy of use OescJiptitm ~ subeection 2a as c~icdemiel, e1111er a .....,nc: description of that 

categoJY. Reacli1tle ,._••*••......., for examtJ6es of genellic 1o1M cdesc~ijDitl-.. 

0 Mark IX} this box if you attach a continuation sheet. 

3 "-ant Include in the notice a copy or reasonabte facsimile of any hazard warning statement, labef, material safety data sM«, Gr 

other informa1ion which wiH be provided to any person regarding protective equipment or practices for the safe hanc:ling. 

transport, use, or dispoMI of the new chemical substance. List in part Ill any hazard information you include. 

!i} Marie IXJ this box if you llttach hazard information. 
i I Part II- HUMAN EXPOSURE AND ENVIRONMENTAL RELEASE 

~ Section A- INDUSTRIAL SITES CONTROLLED BY THE SUBMITTER 

Complete MCtiGn A tar NCh type of rMnufltCttM'e, ~ • .... opentlon lnvolvllntlthe new cheMical Mlbatanc• at lnduatrlelaltM you control. 

Marie (XJ the "Confidential" box ~~~e~t to any item you claim as conf'ldential. 

1 • Opwatlon ciMcripdon 

co, 

•· Identity- Enter the identity of the site at which the operation wiH ox:cllllt. d•nl 

NIHIMl 

KMI Sales£ Inc 

Site address tnumber and street) 

21a Kock Street 

City, County, State, ZIP code 

Pekin Tazewell, Illinois 61554 

If the same operation wil occur at more than one site, enter the r:~umber of shes. I 

Identify the additional sites on a continuation sheet. I 

I 

0 Mart IXJ this box if you attach a continuation sheet. I 

b. Type- liJ Manufacturing 0 Pl!ocessms 0 Us.e Marie (X} 

o. Amount and Duration - Complete 1 01 2 a appropriate 

Muimum kg/batch I 1-tGuPsfibetch I Ballcl!les/year 

1. S.tch NA I I 

I I 

Maximum kg/day I 1-tGuPs/dey I Da.ys/y-ear 

2. Continuous NA I I 

I I 

d. Proceaa description 

(1t Diagram the major unit operation steps and chemical conversions. 

121 Provide the identity, the approximate weight lby kg/day or kg/batch), and entry poiflllt of all feedstocks (illlcluding reactants, - solvents, and catalysts). 

(3) Identify by number the points of release to the environment of the new chemical suiDstance. 

The process is not know to the importer, but the product can be made by 

reacting the polyol with the oxirane group of the epichlorohydrin and 

reestablishing the oxirane group with strong caustic. 

MMII fXJ this box if you attach a continuation sheet. 

Page 7 
Part II- HUMAN EXPOSURE AND ENVIRONMENTAL RELEASE- Continued 

~ Section A - INDUSTRIAL SITES CONTROLLED BY TrNE SUBMITTER - Continued 

2. Occupetfonat Expot~Ut"e - You must make separate confidentiality claims for the description of worker activity, physical fonn of the new chemic substance, number of workers exposed, and duration of activity. Mark (X) the "Confidential" box l'l&xt to any item you claim as confidential. t 1) - Describe the activities in which workers may be exposed to the new chemical subatance. Include activities i111 which workers wear protective equipme 

12~ - Mark (X) this column if entry in column ( 1) is confidential. 

13) - Indicate the physical formls) of the new chemical substance at the time· of exposur-e. 14~ - Mark (X) this column if entry in column (3) is confidential. 

15) - Estimate the maximum number of workers involved in each activity. 

16) - Mark IX) this column if entry in column (5) is confidentiaa. 

171 and (8~- Estimate the maximum duration of the activity for an.y worker in hours. per day and days per year. 19) - Mark (•X) this column if entries in columns (7) and (8) 81'8 confidential. 

WorkM activity 

11) 

None. The imported subtance 

will be shipped in the original 

containers. 

0 Mark (X} this box H you lfttach a continuation sheet. 

c-tl- Physical Conti· ......._. form(e) ....._, 

~~ (~ (. 

c..ft... Maxilllllwm dlllration Co 

...... HrsJdat( 0~/'l'r del 

(6) 17) (81) (1 

3. Environnlentlll ......_ lind DlapotNtl - You must make separate confidentiality claims for the retease number and the amount of the new chemt substance released and other release and disposal information. Mark (X) the "Confidentiat" box next to each i:tem you claim as confidential. 

111 - Entet' the number of each release point identified in the process description, pan tl, sectian A, subsecliiooft 1 0(3). 121 - Estimate the amount of the new chemical substance reteased directly to the erwil'onment or into COI'IItrcllll technology lin kg/day or kg/batch). 13) - Mark IX) this column if entries in columns 11) and !2) are confidential. • 

141 - Identify the media lair, land, or watM) to which the new substance will be l'8leasecl frOfllll that retease poin!t. 151 - Describe control technology, if any, that will be used to limit the release of the new substance to the erwironment. For releases disposed of on land, charactMize the disposal method. 

161 - Mark lXI this column if entries in columns 14) a'ld !5) are confidential. 

171 - Identify the destinationlsl of releases to watM. 

Release Amount of new substance Confl. Media of 

Number released ........, release 

(1) 121 13) (4) 

NA. Imported 

17) Mark (X) the destination(&) 0 POTW (publicly owned 

of releases to watet'. treatment works) 

0 Mark ()() this boK H you attach a continuation sheet. 

FORM EPA· 77fQ-25 0 2· T 8-841 

0 Navigable 

waterway 

PageS 

D Other - Speci(y 
., ~ ' . Pan II- HUMAN EXPOSURE AND ENVIRONMENTAL RELEASE - Continued 

i ~ Section 8 - INDUSTRIAL SITES CONTROLLED BY OTHERS 

Complete MCtlen 8 for MCil type of proceatllntl or ... operetlon lnvohfnsl the new chetnlul subet8nce 8t eltee you do not control. 

To cltlim infomtlltion In this aection as confidential, circle rx bracket the ••dflc information that you cktim as confidential. 

Operation description 

Describe the typical pt'ocessii'IG or use operation. Identify the unit operation steps which may occur dwin; 1he operation. Estimate the number of si1es at which the operation is likely to occur. Identify sit\.Nrtions in which worker exposure te and/or environmentat release of the new chemical substance may occur. Estimate the percent of new chemic.al substance as~ in products manufactured! for commercial purposes in the operation or as used in the operation. Estimate the nwnber of workers exposed IM'ICit the duration ol exposure. Identify controls which limit worker exposure and emrironmental release ;t typic:aly used. Identify bypt'oducts which may resutt from the operation. 

The PMN substance is a rective diluent for high performance 

epoxy compounds. It will be formulated with epoxy resins 

and other ingredients to make high performance resin systems intended for use in aerospace applications. 

n Mart IX) this box if you ettech a continuation sheet. 

FOAIIt'IPA-71'r0"25 ( t 2·18-84) Page9 
\ Part Ill- LIST OF ATTACHMENTS 

Attach continuation sheets for sections of the form and test data and other data (including physical/chemical properties and 

structure/activity informationl, and optional information after this page. Clearly idert11ify the attachment and the section of the fonn to 

which it relates, if appropriate. Number consecutively the pages of the attachments. 1111 the column below, enter the inclusive page 

numbers of each attachment. 

Mark (X) the "Confidential" box next to any attachment name you claim as confidential. Read the ln.wctions M•nual for 

guidance on how to claim any information in an attachment as confidential. You must include with the sanitized copy of the notice 

form a sanitized version of any attachment in which you claim infonnation as confidential. 

Attachment name Attachment c. 

page number(sl .. C! ......... ,...,: fl'nvi l"n1 nt1i ca.l Data 11-14 ... 'I'P.t!hnical Data Sheet 15-17 

_0 Mark IX) this box if you attach a continuation sheft. Enter the attachment name and number. 

FORM EPA-7710.25 (12-18-841 Page10 
SHEREX CHEHICAL COMPANY, Inc. 

Mr. John D. Durig 

P.O. Box 646 

Dublin 

Ohio 43017/USA 

Schering Akliengesellschafl 

c~ lnduslrie-Chemikalten 

ictr.ton tC :~ 07di&·1 

IC-CP/P.-G. .:::;o>•r·~·2246 27. 05.88 

Re: Reactive Diluents 

Dear 11r. Durig, 

attached you'll find a survey of toxicological data with literature 

sources of 12 reactive diluents (phenylglycidylether is not on our 

sales list). 

The data were collected by a working group of the "Association of 

.Plastic Hanufacturers in Europe" (AP11E). 

Best regards ' .. 

Page 11 

~ostanschrift: Schering Aktil'ngesellschaft. Postfach 15 40, 0-4709 Bergkamen ~;.:· =·:·· _:-,:·. ;:.,,.;_:. ,,.-.. · · .• 1 :: .:·. ~.· ·.: · ~'-'"···- .• ::2~ :-:- ' .. . :. -.•. · : . . . . . . . .. ..... ,. . ~- . . . .. ... 
.. 

. -· . - . 

\ . :·-

.-.. 

... 

-, 

··-J 

Survey of Toxic-ological Oatas withLiterature of 12 Reacti.ve Oil uents · ·: 

RV-World ng group of 

APME~ERC-HSE~Subcommitee 

February 1987 Members: Dr. E. Albrecht, Hoechit 

Mr. K. Bhagwati, Dow 

Dr. F. Kugler, Ciba-Geigy 

Dr. B. Meier, Bakelite 

Hr. W. Press, Schering 

Dr. B. Reeve, Shell 

Dr. S. Schaaf, EMS 

Abbreviations of Reactive Oiluents CAS-No. 

NPGOE 

CGE 

::GE 

EHGE 

BDDGE 

c12-c14-Alkyl-GE 

BPGE 

c13-c15-A 1 kyl-GE 

PPODGE 

PGE 

= Neopentylglykoldiglycidylether 

= C~esylglycidylether 

= n-Butylglycidylether 

= 2-Ethylhexylglycidylether 

= Butandiol-1,4-diglycidylether 

=Alkyl (c12-c14 )glycidylether 

= p-tert. Butylphenylglycidylether 

. ·. 

_ = Alkyl {c13-c15) g lycidyl_ether 

= Po lypropyl eneglyco 1 di glyci dyl ether 

= Phenylglycidylether 

17 557-23-2 

o-: 2 210-79-9 ?f:lt'l1..:}1 

p-: 2 186-24-5 

2 426-08-6 

2 461-15-6 

2 425-79-8 

, 68 609-97-2 

3 101-60-8 

I 68 081-84-5 

30 401-87-7 

122-60-1 -

L_ = Glycidylether_ of propoxylated glycerol 

Datas collected by Or. S. Schaaf Pa e 12 

Corrections and additional informationsg 

----~--------------in~ritten manner to Dr .. S. Schaaf 
.. ... . . - A '.,., ..• 

SUBSTANCE 

CAS-No··· 

Viscosity .· 

mPa-s (25°C) 

Vapour P.ressure(63 

mbar (20°C) . 

Solubility in (63) 

water g/l t 

LD 50 oral 

mg/kg 

LD 50 derm. ··-.. mg/kg 

• • ~''·.:. --~--· > • '·· "'--.' ~- : 

Skin irrit~tion 

:.Skin sensitizati 

' ·.· . ........ ... _..... -:--------~::::.:;.:;:. 

·Ames-test 

-... . . 

. •·: .-. 

( i f! _ v i t ro) . 

: .... Cytogenetic test 

(in vivo) 

Carcinogenicity 

( s k i n pa i n t i n g) 

·Reproductive .·· 

(dominant_letha1) 

Teratogenity .· 

Classification. 

R-Phases 

S-Phases 

Paint directives 

30401-87-7 

PGE 

122-60-1 

6 - 9 

3,3 

2 11 

7 5000 (rats) 3850 ( 25 )( 32 )(55)( 64) 

{101) 4260 (57) 

7 5000 (rats) 

(101) 

x. 

.. 

' 

!agg ~)1~~~~}~~ h> 

2160 (rats) (25)(58) 

2990 (rabbits)(55j 

1500 (rabbits)(57) 

mild to moderate 

(32)(55){57)(61) 

severe (32) 

( 57) {58) ( 60) { 64 ) 

negative 65) 

positive 62 69 

( 12 ppm, inhalation) 

negative (62)(69) 

1 inha1ation 

negative (26) 

(55) ~4 )( 65) . 

(93) 

, 

36/38, 43 

28(W+S), 37/39 

x. )1 

Harmful, Xn 

21 , ~-2-3 ~( v!.-a -P .-=-) -, -:-2-:-4/:-::-2-::-5 .....,\ 

28 (W+S), 37/39 

, :::. X "1 1 

n::. 

Page 13 
- 35 - < 

92. Statement on the comparative irritating ans sensitizing potentialities 

of reactive diluents of teh monoepoxide typ~. 

Shell Chemical Company, November 1966 

93. Terill, J.B. and Lee, K.P. 

The inhalation toxicity of phenylglycidyl ether: mutagenic teratogenic 

cytogenic and 90-days studies. Tox~ Appl. Pharm. 37 (1) : 191, 1976 

94. Stankevich, K.I. et al 

Hygenic characertistics of epoxy glue K-4S 

Vrach.Delo, (4) : 137-140, 1972 

95. Shell - Internal data sheet of Dec 1986 

96. Data from Proctor Gamble (Shell Internal data sheet of Dec. 1986) 

... · .......... 97. Schering, Dez. 1978 

,.-· ; 

~-· 

98. Schering, Nov. 1978 

99. Schering, Oct. 1979 

100. Sche~ing, Jan. 1981 : I~dic~tions from Proctor And Gamble Corp. 

101~ Ciba Geigy Report, August 8, 1972 

.. 102~' EMS INBI FO, .B' Test report A 0405/103 e 26. April 1972 

103. EMS INBlFO, Testreport A 0405/013 b 20. April 1972 

104. EMS INBJFO, Testreport A 0405/013 f 26. April 1972 

105.· EMS INBIFO, Testrepori A 0405/013 d 24.April 1972 

106. EMS INBlFO, Testreport A 0405/1052, 26. Feb. 1974 

107. EMS INBIFO, Testreport A 0405/013 c, 24.April 1972 

108. Bakelite GmbH (written statement of Or. Meier of 17. February 1987) 

109. Canter, D. A. et al. Mut. Res. 172 (1986)~.105-138 (see also 70.) 

110. EMS-CCR Report 101 801, February 1987 

llL EMS-CCR Report 101 608, February 1987 .. 

112. EMS-CCR Report 101 _700, February 1987 

' 

·- , __ -- · 113. EMS-CCR Report 102 104, February 1987 .--c _. · 

Page 14 
Table 1: Reactive diluents for Epoxy resins 

..-

Diluent K c cresyl-glycidyl ether ., 

aromatic 

p·tertiary bulylphenyl .. Diluent P .. . , glycidyl ether 

Diluent A ethylhexyl·glycidyl ether 

mono 

functional 

Diluent B bulyl·glycidyl ether 

DiluentE long chain aliphatic 

glycidyl ether 

Diluenl G long chain aliphatic 

glycidyl ~ther 

Diluent 0 butnncdtol-diglycid)•l ether aliphatic 

-~- m:~¥~:..;;,~;~:=~:::'7.::;;,..~~- oilue"h 

~---=~S.~!,?'ll'!'. 

. . . ~ .. ~xa~~p)igJ<trf~4'i:~2~ ... , ..,..:...,!!·· . ·~~-~~·.:•···''-'""'~~··h-·•·.:·.'· ',•' ·~' ", difunctional -· ---'1·' ,;;:..,_:.,...:,.;..; ,,l;...,v-~;. ... ~~ ........ ~9-.i:'i:'"~· 

Diluent N neopentyl·diglycidyl ether 

polyoxypropylene - Diluent F ·" 

diglycidyl ether 

Diluenll polyoxypropylen~ trifunctior;::~i triglycidyt ether 

- -- Table 2 summarises the mosl important analytical data for the formulator and user. 

Table 2: Analytic 

Ac~ctivc dilucnls 

~- p A B E G D 

.. ' ~:;~-:;.;;,, 

~~~- N F L 

0.53-~ 57 0 43-0.47 0 49-0 53 0.7(1-0.7() 0.31-0.3G ~ 0.32 OG;-C.76 o:.~:ss 0.62-067 c~. 0.21 Cll. 0.1-l 

I _;- .... : 

11:-· s~· 21:"1-:?33 18~-205 l ::!:Z-143 278-3:?3 ~ 313 132-,.0:5 152-'167 1·19··1G1 ca 47~ ca 715 

.•- ·: 1!-.-.?!j : ~~-.1 ~- i ~· ~-1.5 ~-15 ca 1!i ca :?5 ca.25 ca 20 Cll (\() ca :70 I 

J v:s:~st1y :-nr .. ,, s '2s~ C 

-. 23 41.0 l !:.7 <: 0 1 ·, <0.1 ~ -~ ~$·.~~~· 1.5 <0.1 <01 va:>ctJr oressur"! "''bar 2(f' C 

:; ; ~4 <It 1 <£ 1 ~2 ca.:? 1103 ,:f}!~~':'?·.' 1!.2 ca. 2 ca 4 ·...rr~-·)·:l· .. ':olou· va:ue (Ga~dncr) 

1 ~ :. 1.02 0.!10 0 95 0 89 0.85 1 10 '}:it'olr 

.~.t<"i~··. t.OG 1.03 105 

"•ash ooinl DIN 51758 ca 1i~· c ca. tJs•c ca. 93"C ca. 154" C ca. ISO• C ca. 160" C ·~i.J:"""·' 

ttt~t.C. ca. 140• C ca 130" C ca. t.:o• c 

t& 40"C ~~·~7 ' Frasn oor:'ll DIN 53213 -~fi~ . " " 

:o:t'~~ 

Page 15 
·1..· 

... · f 

1h 

Health and safety aspects 

Reactive di!uents show. in comparison to the high molecular epoxy resins. a 

significantly higher safety risk. The primary skin irritation and sensitization caused by 

reactive dituents are more signilicant than with the higher molecular weight epoxy resins. 

Increased caution is necessary especially because reactive dituents. due to their 

evaporation rate and the fact that they are able to penetrate the skin also increases the 

risk with respect to systematic toxictty. 

Reactive diluents have been shown to have mutagenic effects when tested 

against bacteria (AMES-test). When using reactive diluents any irritations which may 

occur will be noticed primnrily on the skin or mucous membranes. With short chain 

reactive diluents (see table 9). due to the relatively high vapour pressure, an irritating 

clfect can be noticed in the facial area and mucous memlmmes. in addition to the skin 

irritating r>roporties. Prolonged exposure in rooms with inndequntP. venlilatton will lead to 

tedness or irritation of the fac:at and eye area. 

The latest results of a tongterm study of neopentytgtycot-diglycidyl·ether (Oak 

Ridge National Laboratory. Report ORNL 5762, June 1981 ). indicates that this product 

can be classifted as slightly carcinogenic on animal's skin under the test conditions stated 

in the report. The result of this was an agreement between the Europenn manufacturers 

on a voluntary labelling of this product as having a harmful effect on he<::;lt with the indi· 

calion 'irreversible damage possible'. 

With this the manufacturers want to avoid possible harmful effects which could 

n'!sull from unqtmlified handling of the product. 

When utilizing reactivo t1iluents or reactive diluen't modified epoxy resins. it is 

nece!:.::~ry to consult the pampt.!et 111\023 (Polyester and Epoxy resins) olthe Berufs· 

genosscnschalt der Chemischen tndustrie. Further we would like to point out that our 

brochure 'H:nts on Toxicology and Safe Handling - Epoxy Resins/Curing Agents' and 

the tnforrna:ion contatned in the satety data sheets contain information on the correct 

handling and use of tnese products. This information shows that sale handling ol these 

products is possible i! skin contact and inhalation of the product is avotded by the use of 

aprropriate skm protection, safety clothing and adequate ventilation of the work area. 

Page 16 
"' " ~Table 9: Health and Safety Evaluation 

~ 

Product Ct.em. L050ora• Skm Compatibility St!nSrhzahon Vapour Markmg accordm!;: 

Name Identity rnglkg reel Compatibility to mucous pressure to "Dangerous 

memhranes 20•c mbar Goods Act. (Oc:. 861"' 

EC Guidehnes 

Diluent K Cresyl· >2000 On smgle contact No •rritation Sensitizer 2.0 '"Xi'" -- glycrdyl· moderate. repeated R:36;43 

ether contact moderate 5.26;28 

to stronger 

irrilation 

DiluentP P.tert. > 10000 Can lead to very Can cause Can act as 2.3 

Butyl· modcmlc trruation irntation sensitizer 

phenyl. on longer exposure 

gtvcidyl· 

ether 

Diluent A Ethyl· > 7500 Can lead to Eve rrntauon Sensilizer 4,0 

hexyl· ir utalrnn on longer possible 

glyCtdyt· exposure 

ether 

DiluentB Butyl· >2000 On singll• contar.t No rmlahon Sensitizer 5.7 "Xn" 

glycrdyl· moderatu. rope.11cd A- 10; 20; 43 

e111~r contact moderate S: 24125 

to :>tronger 

trrllahon 

Diluent E Longc:::Jin > 10000 Can lead to very No irritattori Sensitizer < 0.1 -- ·~-·-·· aliphahc shght itritatron 

GI)•Cidyl· alter extended 

ether exposure 

Diluent G Longcllain > 1000(1 Can lead to very Cnnact as .::0.1 

aliphatic slight irritahon c;,1nsitizet 

Gtycidyl~. alter extended 

ether exposure 

•· Diluent D 1.4-Butan· 3000 On singi-:J contact Onsrnute Can act as 1.3 "Xn" 

diol· moderate rrntation contact sensitizer R: 20/21; 3GI38: .: 3 

dig!ycidyl· modmale S: 26; 28; 37/3£-

etller tmtatron 

·--·-: ·.:·;"':---._,· --~ .. '~- . .,..,. ·-··. ~ ,. ..... ,. ... --~. ·. . .. 

?~tr~i ·.· .··~IIPd' ~§jj!)gli,~QP~~lJ..~. .. ~.~ii_,·alt-~·· "c.~n~~~~ ~~-:1 .• 0_~-~-. . , . . iiJ:i~?Ca.f!-diok · . · . . ..... :::-=::;..,:'1.~'t..,.~~.;~,:.~;1?~----

~-: .! ;:'digi)•Ctd . ' -;:moderate·~· repeated~ ~poss•bl . · sens•t1zer::wr!'.• -~~1~~~~:i~~- ~:-~-~-;~-,~~:: . .:;;·.:~~-- '<ether'::;;"· . .. ."il~JI~ o;r.""": ,_.coritacl'moderari~" :1:d.$.~"f).;t:""Q .;f . ..:; ·-~· .. :.~.;:.,;:-:;;.\~~·i~~· .. ~-. -.. ;!'(.-.:·_~ 

. .... _>. ~. :~ .. ·: •' ,~_:··: . --~0-~~~·-· '·to'sfroriger irri:ali0n° ~r:r;:::~~r~~~~l:- .::-:"!~~'-~:-=~~~~--.. ·-1:-~h~ ... ~~.u..'\~·u:":";::'f'· .. -:.:7'~-:w.~~~---..... . ·-··.c.;·:. .~...-·::·~~~-~·-:: ~~";-~'<' .. ~-

Diluent N Nccnentvi- > 2000 Cii" i!CI ill' I G::- '~=~ a~ Can ilC! a~:> 1.5 ">;n·· 

ol·l•.OI· n·net!'l! , ... ;:! .,~ Sf!r151tl:!f.:• R· :~0:2 1; 3(\ '3~ 

'"P'>'c•dy:- I ·<0: 43 

ether ''., S: 23: 28: 37/3~ 

DiluentF PolyO:r.)'· >4000 Can lead to Ca·• cause pam. Can ac1 as -:: 0.1 

pro::>~·lene·,. rn!:!dcratc •rrr:atoor. •rrota:•on and sensitizer 

d•pi)'Ctdyl· er~·oamagc 

ether 

DiluentL Potyo:r.y· 7400 Moderate ~rritat•on V<:ry moderate No irritatron <0.1 

propylene· 1rr;1a:•on 

trigtycidyl· 

e;ner 

Page 17 

1'7