8 Federal Register / Vol. 53, No. 98 / Friday, May 20, 1988 / Notices'

ENVIRONMENTAL PROTECTION

AGENCY

[OPTS-41029; FRL-3381-7]

Twenty-second Report of the

Interagency Testing Committee to the

Administrator; Receipt of Report and

Request for Comments Regarding

Priority List of Chemicals

AGENCY: Environmental Protection

Agency (EPA).

ACTION: Notice.

SUMMARY: The Interagency Testing

Committee (ITC), established under

section 4(e) of the Toxic Substances

Control Act (TSCA), transmitted its

Twenty-Second Report to the

Administrator of EPA on May 2, 1988.

This report, which revises and updates

the Committee's priority list of

chemicals, adds 10 chemicals to the list.

for priority consideration by EPA in

promulgation of test rules under section

4(a) of the Act. The Twenty-Second

Report is included with this notice. One

chemical, 1,6-hexamethylene

diisocyanate (CAS No. 822-06-0) is

designated for response within 12

months. In response to ITC's

designation, EPA will either initiate

rulemaking under section 4(a) of TSCA,

or publish a Federal Register notice

explaining the reasons for not initiating

such rulemaking within 12 months.

Crotonaldehyde (CAS No. 4170-30-3);

imidazolium quaternary ammonium

compounds (CAS No. 68122-86-1); and

seven ethoxylated quaternary

ammonium compounds (CAS Nos.

68153-35-5, 68389-88-8, 68389-89-9,

68410-69-5, 68413-04-7, 68554-06-3, and

70914-090-9) are not designated for

response within 12 months. EPA invites

interested persons to submit written

comments on the report, and to attend

Focus Meetings to help narrow and

focus the issues raised by the ITC's

recommendations.

-Additionally, EPA is soliciting interest

in public participation in the consent

agreement process for crotonaldehyde,

imidazolium quarternary ammonium

compounds, and seven ethoxylated

quaternary ammonium compounds.

* The ITC also has removed 9 chemicals

from the priority list. Six

aminoanthraquinone dyes (CAS Nos.

128-86-9, 2861-02-1, 6247-34-3, 6424-85-

7, 12217-79-7 and 17418-58--5) have been

removed from the list on the basis of

relatively low aggregate production. and,

sufficient genotoxicity testing to reduce

concerns about these chemicals.'

Tributyl phosphate (CAS No. 126-73-8),

isopropanol (CAS No. 67-63-0), and

methyl tert butyl ether (CAS No. 1634-

04-41 have been removed because EPA

has responded to the ITC's previous

recommendations for testing of the

chemicals.

DATES: Written comments should be

submitted by June 20, 1988. Submit

written notice of interest in being

designated an "interested party" to

development of consent agreements for

crotonaldehyde, imidazolium quaternary

ammonium compounds and seven

ethoxylated quaternary ammonium

compounds by June 20, 1988. Focus

Meetings will be held on June 14 and

June 17, 1988.

ADDRESS: Send written submissions to:

TSCA Public Docket Office (TS-793),

Office of Toxic Substances,

Environmental Protection Agency, Rm.

NE G-004, 401 M Street SW.,

Washington, DC 20460.

Submissions should bear the -

document control number (OPTS-41029).

The public record supporting this

action, including comments,..is available

for public inspection in Rm. NE G-004 at

the address noted above from 8 a.m. to 4

p.m., Monday through Friday, except

legal holidays. The Focus Meetings will

be held at EPA Headquarters, Rm. 103

NE Mall, 401 M Street SW., Washington,

DC. Persons planning to attend the

Focus Meetings, and/or seeking to be

informed of subsequent public meetings

on these chemicals, should notify the

TSCA Assistance Office at the address

listed below. To ensure seating

accommodations at the Focus Meetings,

persons interested in attending are

asked to notify EPA at least one week

ahead of the scheduled date.

FOR FURTHER INFORMATION CONTACT:

Michael M. Stahl, Acting Director, TSCA

Assistance Office (TS-799), Office of

Toxic Substances, Environmental

Protection Agency, 401 M Street SW.,

Washington, DC 20460, (202) 554-1404.

:SUPPLEMENTARY INFORMATION: EPA has

received the Report of the TSCA

Interagency Testing Committee to the

Administrator.

I. Background

TSCA (Pub. L. 94-469, 90 Stat. 2003 et

seq; 15 U.S.C. 2601 et seq.) authorizes

the Administrator of EPA to promulgate

regulations under section 4(a) requiring

testing of chemical substances and

mixtures in order to develop data

relevant to determining the risks that

such chemical substances and mixtures

may present to health and the

environment. Section 4(e) of TSCA

established an Interagency Testing

Committee to make recommendations to

the Administrator of EPA on chemical

substances and mixtures to be given

priority consideration in proposing test

rules under section 4(a). Section 4(e)

directs the ITC to revise its list of

recommendations at least every 6

months as necessary. The ITC may

"designate" up to,50 substances and

mixtures at any one time for priority.

consideration by the Agency. The

chemical 1,6-hexamethylene

diisocyanate'is a designated chemical.

For such designations, the Agency must

within 12 months either initiate

rulemaking or issue in the Federal

Register its reasons for not doing so. The

ITC's Twenty-Second Report was

received by the Administrator on May 2

and follows this Notice. The Report

adds 10 substances to the TSCA section

4(e) priority list.

II. Written and Oral Comments and

Public Meetings

EPA invites interested persons to

submit detailed comments on the ITC's

new recommendations. The Agency is

interested in receiving information .

concerning additional or ongoing health

and safety studies on the subject

chemicals as well as information,

Srelating to the human and environmental

exposure to these chemicals.

A notice is published elsewhere in

today's IPederal Register adding 8 of the

10 substances recommended in the ITC's

Twenty-Second Report to the TSCA

section 8(d) Health and Safety Data

Reporting Rule (40 CFR Part 716]. Two of

the 10 substances, 1,6-hexamethylene

diisocyanate (52 FR 16022, May 1, 1987)

and crotonaldehyde (51 FR 2890, January

22, 1986), already are subject to this rule,

which requires the reporting of

unpublished health and safety studies

on the listed chemicals. All 10 chemicals

will be added to the TSCA section 8(a)

Preliminary Assessment Information

Rule (40 CFR Part 712) published

elsewhere in this issue. The section 8(a)

rule requires the reporting of production

volume, use, exposure, and release

information on ,the listed chemicals.

Focus Meetings will be held to. discuss

relevant issues pertaining to these

chemicals and to narrow the range of

issues/effects which will be the focus of

the Agency's subsequent activities in

responding to the ITC recommendations.

The Focus Meetings will be held as

follows::

June 14,.1988

9:30 a.m.-Imidazolium quaternary

ammonium compounds

1:00 p.m.-Ethoxylated quaternary

ammonium compounds

June 17, 198.8

9:30 a.m.-Crotonaldehyde

1:00 p.m.-1,6-Hexamethylene

diisocyanate

mmft I

1 18196.
Federal Register / Vol. 53, No. 98 / Friday, May 20. 1988 / Notices -

They will be held at EPA or the environment. It also provides for Headquarters, Rm. 103 NE Mall, 401 M the establishment of a Committee (ITC), Street SW., Washington, DC. These composed of representatives from eight meetings are intended to supplement designated Federal agencies, to

and expand upon written comments recommend chemical substances and

submitted in response to this notice. mixtures (chemicals) to which the

Persons wishing to attend these Administrator of the U.S. Environmental

meetings, or subsequent meetings on Protection Agency (EPA) should give these chemicals, should call the TSCA priority consideration for the

Assistance Office at the telephone promulgation of testing rules.

number listed above at least one week

in advance. Section 4(e)(1)(A) of TSCA difects the This notice also serves to invite Committee to recommend to the EPA

persons interested in participating in or Administrator chemicals to which the

monitoring negotiations for consent Administrator should give priority

agreements for crotonaldehyde, consideration for the promulgation of

imidazolium quaternary ammonium testing rules pursuant to section 4(a).

compounds, and ethoxylated quaternary The Committee is required to designate ammonium compounds to notify EPA no those chemicals, from among its

later than June 20, 1988. The procedures recommendations, to which the

for negotiations are described in 40 CFR Administrator should respond within 12

790.22. All written submissions should months by either initiating a rulemaking bear the identifying docket number proceeding under section 4(a) or; (OPTS-41029). publishing the Administrator's reason

III. Status of List for not initiating such a proceeding. At

least every 6 months, the Committee In addition to adding the 10 makes those revisions in the TSCA

recommendations to the priority list, the section 4(e) Priority'List that it

ITC's Twenty-Second Report notes the determines to be necessary and

removal of 9 chemicals from the list transmits them to the EPA

since the last ITC report. Six Administrator. aminoanthraquinone dyes have been Amnsrtr

removed from aminantraqinoe the list dys by the hve ITC on 

een As a result of its deliberations, the the C i reis eb a setio

basis of relatively low aggregate Committee is revising the TSCA section

production and sufficient genotoxicity 4(e) Priority List by the addition of 10

testing to reduce concerns. Subsequent chemicals.

to ITC's preparation of its Twenty-First The Priority List is divided into three

Report, EPA responded to the ITC's parts: Part A'contains those

recommendations for three additional recommended chemicals and groups chemicals. The three chemicals removed designated for priority consideration

and the dates of publication in the and response by the EPA Administrator

Federal Register of EPA's responses to within 12 months. Part B contains

the ITC for these chemicals are: tributyl chemicals and groups of chemicals phosphate (52 FR 43346, November 12, recommended with intent-to-designate. 1987); isopropanol, (53 FR 8638, March This category was established by the 16, 1988); and methyl tert butyl ether (53 Committee in its seventeenth report (50 FR 10391, March 31, 1988). FR 47603; November 19, 1985) to take

The current list contains 1 designated advantage of rules promulgating substance, 2 chemicals recommended automatic reporting requirements for with intent-to-designate, and 14 non-designated ITC recommendations

recommended substances. under the section 8(a) Preliminary

Authority: 15 U.S.C. 2603. Assessment rule and the TSCA.section

Dated: May 11, 1988. 8(d) Health and Safety Data Reporting J. Merenda, rule. Information received following

Director, Existing ChemicdlAssessment recommendation with intent-to- Division. - designate -may influence the 'Committee

to either designate of not designate the Twenty-Second Report of the.TSCA chemicals or groups of chemicals in a Interagency Testing Committee to the subsequent report to the Adminisfiator.

Administrator, Environmental Protection Part C contains chemicals'and'groups of Agency • chemicals that have been recommended

Summary .. for priority consideration by EPA

.Section 4 of the Toxic Substances without being designated for response

Control Act of 1976 (TSCA, Pub. L. 94- within. 12 months. The changes to, the.

469) provides for the testing of! Priority List are presented, together with

chemicals in commerce that-may present the types of testing recommended, in the an unreasonable risk of injury to health following Table 1:,

TABLE 1-ADDITIONS TO THE SECTION

4(e) PRIORITY LIST, MAY 1988

Chemical/Group

A. Designated for

response within 12

months:

1,6-

Hexamethylene

diisocyanate I

CAS No. 822-

06-0.

B. Recommended

with Intent-toDesignate:

Crotonaldehyde 2

CAS No. 4170-

30-3.

C. Recommended

Without Being

Designated for

Response Within

12 Months:

Imidazolium

Quaternary

Ammonium

Compounds 3

(CAS No.

68122-86-1).

Ethoxylated

Quaternary

Ammonium

Compounds 4

(CAS Nos.

68153-35-5,

68389-88-8,

6889-89-9,

68410-69-5,

68413-04-7;

68554-06-3,

and 70914-09-

9).

Recommended studies

Health Effects: Chronic toxicity, including oncogencity;

reproductive and developmental effects.

Chemical Fate: None

Ecological Effects: None

Health Effects: None

Chemical Fate: Volatilization

rate from water;, aerobic

aquatic biodegradation

rate. . I

Ecological Effects: Acute

toxicity to algae, fish and

aquatic invertebrates.

Health Effects: Chronic toxic-

.iy studies to evaluate potential ' effects through long-term dermal exposures.

Chemical Fate: Aerobic and

anaerobic biodegradation

of the chemical sorbed to'

freshwater and estuarine

sediments.

Ecological Effects: Acute

and chronic effects on

representative freshwater

and estuarine benthic organisms.

Health Effects: Chronic toxicity studies to evaluate potential effects through

long-term dermal exposures.

Chemical Fate: Aerobic and

anaerobic biodegradation

of the chemicals sorbed'to

freshwater and estuarine

sediments.

Ecological Effects: Acute

and chronic effects 6n

representative freshwater

and benthic organisms.

CA Index Names (9 CI) 'Hexane1 t,6 diisocyanato-. 2-Butenal. 3 Imidazolium compounds, 4,5-dihydro-1;methyl-2-

nortallow alkyl--(2-tallow amidoethyl), Me sulfates. 4 Ethanaminium, 2-amino-N-(2-aminoethyl)-N.(2-hydroxyethyl)-N-methyl-, NN'-ditallow acyl derivs., Me sulfates (salts); CAS No. 68153-35-5, . Poly(oxy-1,2-ethanediyl), a-t2-[bis(2-aminoethy)- methylammonio]-ethylJ--hydroxy. N.N'-dicoco acyl derivs., Me sulfates (salts); CAS No: 68389-88-8, Poly(oxy-1,2.ethanediyl), a-[2-[bis(2-aminoehy)- methylammonio]-ethyl].-o-hydroxy. I N,N'-

IR1017

lfilOq

Recommended studies
Federal Register / Vol. 53, No. 98 / Friday, May 20, 1988 / Notices

bis(hydrogenated tallow atyl) defies., Me sulfate

(salts); CAS No. 68389-89-9,

Poly(oxy-1,2-ethanediy), a-[2-[bis(2-aminoethyl) . methylammonio]-ethyl]-w-hydroxy-... N,N'-ditalloi

acyl devs., Me.sulfates (salts); CAS No. 68410-69

5,Polytoxy(methyl-1,2-ethanediyl)], a-t2-[bis(2

aminoethyi)-methytammonio]-methylethyl]-i,)-

hydroxy-, N,N'-, ditallow acyl derivs., Me sulfate

(salts); CAS No 68413-04-7,

Poly(oxy-1,2-ethanediyl). a-[3-Ebis(2-aminoethyl) methylammonio ]-2-hydroxypropyl] -&-hydroxyo, I

coco acyl derivs.. Me sulfates (salts); CAS Nc

68554-06-3. and

Poly(oxy-1,2-ethanediyl). a-[2-[bis(2-aminoethyl]

methylammonio]-ethyl]-w-hydroxy-, N.N'-di-C,,-,

acyl defivs., Me sulfates (salts);CAS No. 70914-09

9

TSCA Interagency Testing Committee

Statutory Member Agencies and Their

Representatives

Council on Environmental Quality

Joseph Jehl, Member 1

Department of Commerce

Partick D. Cosslett, Member

Raimundo Prat,.Alternate

Environmental Protection Agency

John D. Walker, Member

Laurence S. Rosenstein, Alternate

National Cancer Institute

Richard Adamson, Member

Elizabeth K. Weisburger, Alternate

National Institute of Environmental

Health Sciences

James K. Selkirk. Member and

Chairperson

National Institute for Occupational

..Safety and Health

Bryan D. Hardin, Member and Vice

Chairperson

Rodger L. Tatken, Alternate

National Science Foundation

Rodger W. Baier, Member

Jarvis L. Moyers, Alternate

Occupational Safety and Health

Administration

Robert Turnage, Member 2

Stephen Mallinger, Alternate

Liaison Agencies and Their

Representatives

Consumer Product Safety Commission

Lakshmi C. Mishra

Department of Agriculture

Richard M. Parry, Jr.

Elise A. B. Brown

Department of Defense

Vacant

Department of the Interior

Sarah Gerould

Food and Drug Administration

Arnold Borsetti

National Library of Medicine

Vera Hudson

National Toxicology Program,

Dorothy Canter

Committee Staff

Robert H. Brink, Executive Secretary

I Appointed on October 30,1987.

2 Appointed on October 26, 1987.

s Norma Williams, ITC Program Specialist

Support Staff

Alan Carpien--Office of the General

Counsel, EPA

The Committee acknowledges and is

grateful for the assistance and support given the ITC by the staff of Dynamac

Corporation (technical support

contractor) and personnel of the EPA Office of Toxic Substances.

Chapter 1-Introduction

1.1 Background. The TSCA

Interagency Testing Committee

(Committee) was established under

section 4(e) of the Toxic Substances

Control Act of 1986 (TSCA, Pub. L. 94-

469). The specific mandate of the

Committee is to recommend to the

Administrator of the U.S. Environmental

Protection Agency (EPA) chemical

substances and mixtures in commerce

that should be given priority

consideration for the promulgation of

testing rules to determine their potential

hazard to human health and/or the

environment. TSCA specifies that the

Committee's recommendations shall be

in the form of a Priority List, which is to

be published in the Federal Register.

The Committee is directed by section

4(e)(1){A) of TSCA to designate those

chemicals on the Priority List to which

the EPA Administrator should respond

within 12 months by either initiating a

rulemaking proceeding under section

4(a) or publishing the Administrator's

reason for not initiating such a

proceeding. There is no statutory time

limit for EPA response regarding

chemicals that ITC has recommended

but not designated for response within

12 months.

At least every 6 months, the

Committee makes those revisions in the

section 4(e) Priority List that it

determines to be necessary and

transmits them to the EPA

Administrator.

The Committee is composed of

representatives from eight statutory

member agencies and seven liaison

agencies. The specific representatives

and their affiliations are named in the

front of this report. The Committee's

chemical review procedures and priority

recommendations are described in

previous reports (Refs, 1 through 6).

.1.2 Committee's previous reports.

Twenty-one previous reports to the EPA

Administrator have been issued by the

Committee and published in the Federal

Register (Refs. 1 through 6). Ninety-six

entries (chemicals and groups of

chemicals) were recommended for

priority consideration by the EPA

* Administrator and designated for

response within 12 months: In addition,

fourteen chemicals and one group of

chemicals were recommended without

being so designated..

1.3 Committee's activities during

this reporting period. Between October

16,1987 and April 21, 1988, the

Committee continued to .review

chemicals from its fifth and sixth scoring

exercisesxand from nominations by

Member Agencies, Liaison Agencies and

State Agencies.

The Committee contacted chemical

manufacturers-and trade associations to

request information that would be of

value in its deliberations. Most of those

contacted provided unpublished

information on current production,

exposure, uses, and effects of chemicals

under study by the Committee,

During this reporting period, the

Committee reviewed available

information on eighty-four chemicals.

Ten were selected for addition to the

section 4(e) Priority List, and twentyfour were deferred indefinitely. The

remaining chemicals are still under

study.

In its twentieth report to the EPA

Administrator (Ref. 5, ITC, 1987), the

Committee placed ethylbenzene (CAS

No. 100-41-4) on the Priority List on the

"Recommended with Intent-toDesignate" category. The Committee

recommended that ethylbenzene be

tested for acute toxicity to freshwater

algae and invertebrates and. to saltwater

algae, invertebrates and fish.

Subsequently, the Committee learned

that acute toxicity testing of

ethylbenzene with freshwater

invertebrates had recently been

completed at the University of

Wisconsin As noted in the twenty-first

report, the Committee also was informed

that a consortium of ethylbenzene

-producers, the Styrene and

Ethylbenzene Association, voluntarily

sponsored studies on the other acute

toxicity tests recommended by the

Committee. The Committee deferred a

decision on whether or not to designate

ethylbenzene pending a review of the

data developed during the-above

studies. The Committee has reviewed

the data developed in those studies and

has concluded that all of the data gaps

identified in the, twentieth report have

been satisfactorily resolved with the'

exception of saltwater invertebrate

testing. Industry has volunteered to

sponsor additional studies with

saltwater inver'tebrates. The Committee

has decided to continue to defer a

decision on whether or not to designate

ethylbenzene pending a review of data

from the additional invertebrate tests.

In its twenty-first report to the EPA

-Administrator, the Committee

18198
Feder#1 Register / Vol. 53, No. 98 / Friday, May 20, 1988 / Notices

recommended genotoxicity testing on

six aminoanthraquinone dyes (CAS Nos.

128-86-9, 2861-02-1, 6247-34-3, 6424-85-

7, 12217-79-7 and 17418-58-5).

Subsequent to the recommendation the

Committee had an opportunity to

examine the TSCA section 8(a)

Preliminary Assessment rule and TSCA

section 8(d) Health and Safety Data

Reporting rule information submitted to

the EPA. That information included

current production and use information

on those dyes and additional data on

genotoxicity tests. As a result of its

review of that information, the

Committee has concluded that the six

aminoanthraquinone dyes with the

above CAS numbers should be removed

from the Priority List on the basis of

relatively low aggregate production and

sufficient genotoxicity testing to reduce

concerns.

1.4 The TSCA section 4(e) Priority

List. Section 4(e](1](B) of TSCA direct

the Committee to: " * * make such

revisions in the [priority] list as it

determines to be necessary and * * *

transmit them to the Administrator

together with the Committee's reasons

for the revisions." Under this authority,

the Committee is revising the Priority

List by adding ten chemicals: 1,6-

hexamethylene diisocyanate (GAS No.

822-06-0), crotonaldehyde (CAS No.

4170-30-3), imidazolium quaternary

ammonium compounds (CAS No. 68122-

86-1) and ethoxylated quaternary

ammonium compounds (CAS Nos.

68153-35-5, 68389-88-8, 68389-89-9,

68410-69-5, 68413-04-7, 68554-06-3 and

70914-09-9). Nine chemicals are being

removed from the Priority List at this

time. Tributyl phosphate (GAS No. 126-

73-8) was the subject of a Notice of

Proposed Rulemaking (52 FR 43346;

November 12, 1987). Isopropanol (GAS

No. 67-63-0) also was the subject of a

Notice of Proposed Rulemaking (53 FR

8638; March 16, 1988) and methyl tert

butyl ether (CAS No. 1634-04-4) was the

subject of a Testing Consent Oider (53

FR 10391; March 31, 1988). In addition,

six aminoanthraquinone dyes (GAS Nos.

128-86-9, 2861-02-1, 6247-34-3, 6424-85-

7, 12217-79-7 and 17418-58-5) are being

removed for the reasons given in section

1.3.

With the ten new recommendations

and nine removals noted in this report,

seventeen entries now appear on the

section 4(e) Priority List. The Priority

List is divided in the following Table 2

into three parts; namely, A. Chemicals

and Groups of Chemicals Designated for

Response Within'12 Months, B.

Chemicals and Groups of Chemicals

Recommended with Intent-to-Designate,

and C. Chemicals and Groups of

Chemicals Recommended Without Being

Designated for Response Within 12

Months. Table 2 follows:

TABLE 2-THE TSCA SECTION 4(e)

PRIORITY LIST, MAY 1988

Date of Entry designation

A. Chemicals and Groups of Chemicals Recommended and Designated for Response Within 12

Months:

1. 1,6-Hexamethylene diisocyanate.

B. Chemicals and Groups of Chemicals Recommended with Intent-toDesignate:

1. Ethylbenzene ...............................

2. Crotonaldehyde ............................

C. Chemicals and Groups of Chemicals Recommended Without Being

Designated for Response Within

12 Months:

1. Diisodecyl phenyl phosphite.

2. C.I. Disperse Blue 79 ..................

3. Methyl ethyl ketoxime .................

4. N-[5-[bis[2-

(acetyloxy)ethyl]amino]-2-[(2-

bromo-4,6-dinitrophenyl)azo]-4-

methoxy phenylJ-acetamide.

5. N-5-4bis[2-

(acetyloxy)ethyllamino]-2-[2-

chloro-4,6-dinitrophenyl)azo]-4-

methoxy phenylJ-acetamide.

6. N-[5-[bis[2-

(acetyloxy)ethyl]amino]-2-[(2-

chloro-4,6-dinitrophenyl)azo]-4-

ethoxy phenyl]-acetamide.

7. Imidazolium compounds, 4,5-

dihydro-l-methyl-2onortallow

alkyl-l-(2-tallow amidoethy), Me

sulfates.

8. Ethanaminium,2-amino-N-(2-

aminoethyl)-N-(2-hydroxyethyl)-

N-methyl-, N,N'-ditallow acyl

derivs., Me sulfates (salts).

9.. Poly(oxy-1,2-ethanediyt),a-I2-

[bis(2-aminoethyl)-.

methylammonio ]-ethyl-jhydroxy-, N,N'-dicoco acyl

derivs.,'Me sulfates (salts).

10. Poly(oxy-1,2-ethanediyl),a-[2-

[bis(2-aminoethyl)-

methylammonioJ -ethyl]-o- -

hydroxy-, N,N'-bis(hydrogenated

tallow acyl) derivs., Me sulfates

(salts).

11. Poly(oxy-1,2-ethanediyl),a-[2-

[bis(2-aminoethyl)-

methylammonio-ethyl]-whydroxy-, NN'-ditallow acyl

derivs., Me sulfates (salts).

12. Polytoxy(methyl-1,2-

ethanediyl)],a-2-[bis(2-

aminoethyl)-methylammoniolmethylethyl]-w-hydroxy-, N,N'-,

ditallow acyl derivs., Me sulfates

(salts).

13.. Poly(oxy-1 ,2-ethanediyl),a-(3-

[bis(2-aminoethyl)-

methylammonio]-2-

hydroxypropyl]-o)-hydroxy-, Ncoco acyl derivs., Me sulfates

(salts).

14. Poly(oxy-1,2-ethanediyl),a-[2-

[bis(2-aminoethyl)-

methylammonio]-ethyl]-oihydroxy-, N,N'-di-C,4-s acyl

derivs., Me sulfates (salts).

May 1988

May 1987

May 1988

Nov. 1985

Nov. 1986

Nov. 1986

May 1987

May 1987

May 1987

May 1988

May 1988

May 1988

May 1988

May 1988

May 1988

May 1988

May 1988

References

(1] Sixteenth Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee, May 21, 1985, 50 FR 20930-20939.

Includes references to Reports I through 15

and an annotated list of removals.

(2) Seventienth Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee, November 19, 1985, 50 FR 47603-

47612.

(3] Eighteenth Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee, May 19, 1986, 51 FR 18368-18375.

(4] Nineteenth Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee, November 14, 1986, 51 FR 41417-

41432.

(5) Twentieth Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee, May 20, 1987, 52 FR 19020-19026.

(6) Twenty-first Report of the TSCA

Interagency Testing Committee to the

Administrator, Environmental Protection

Agency. TSCA Interagency Testing

Committee, November 20, 1987, 52 FR 44830-

44837.

Chapter 2-Recommendations of the

Committee

2.1 Chemicals recommended for

priority consideration by the EPA

Administrator. As provided by section

4(e)(1)(B) of TSCA, the Committee is

adding the following chemical

substances to the section 4(e) Priority

List: 1,6-hexamethylene diisocyanate

(CAS No. 822-06-0), crotonaldehyde

(CAS No. 4170-30-3), imidazolium

quaternary ammonium compounds (CAS

No. 68122-86-1) and ethoxylated

quaternary ammonium compounds (CAS

Nos. 68153-35-5, 68389-88-8, 68389-89-9,

68410-69-5, 68413-04-7, 68554-06-3 and

70914-09-9). The recommendation of

these chemicals is made after

considering the factors identified in

section 4(e)(1)(A) and other relevant

information, as well as the professional

judgment "of Committee members.

2.2 Chemicals .designated for response

within 12 months-2.2.a 1,6-

Hexamethylene diisocyanateSummary of recommended studies. It is

recommended that 1,6-hexamethylene

diisocyanate be tested for the following:

1. Chemical fate: None.

2. Health effects: Chronic toxicity

(including oncogenicity) and

reproductive and developmental effects

studies.

3. Ecological effects: None.

18199
Federal Register / Vol. 53, No. 98 /.Friday, May 20, 1988 / totices

Physical and Chemical Information

CAS Number: 822-06-0

Synonyms: Hexane, 1,6-diisocyanato-;

Hexamethylene diisocyanate; 1,6-

Diisocyanatohexane

Acronym: HDI

Trade Names: Desmodur H; Mondur HX

Structural Formula: OCNCH 2CH 2CH2C

H2C2CH2NCO

OCNC H 2CH 2CH 2C H 2C H2CH 2NCOEmpirical Formula: CsH 12N202

Molecular Weight 168.0

Appearance: Liquid

Boiling Point-212.8 'C at 760 mmHg

(Ref. 22, NIOSH, 1978)

Vapor Pressure: 0.05 mmHg at 24 °C

(Ref. 22, NIOSH, 1978]

Specific Gravity: 1.04 (Ref. 22, NIOSH,

1978)

Flashpoint 140 'C (Ref. 22, NIOSH, 1978]

Solubility: Poorly soluble in water;

readily soluble in organic solvents

(Ref. 22,-NIOSH, 1978)

Log Octanol/Water Partition

Coefficient (log P): -1.9 (Est'd., Ref.

14, Leo et al., 1971).

Rationale for Recommendations

I. Exposure Information

A. ProductiornUse/Disposal/

Environmental Release

Hexamethylene diisocyanate (HDI) is

produced in commercial quantities at

Baytown, TX; current annual production

is about 11 million pounds (Ref. 19,

Mobay, 1988b). Laboratory quantities of

HDI are also produced by M6rton

Thiokol, Inc. at its Danvers, MA plant

(Ref. 10, ICF, 1986). The public portion of

the TSCA Inventory lists U.S. "

production at1 to 10 million pounds in

1977 (Ref. 27, USEPA, 1988). No import

data are reported for HDI. In 1981,

approximately 2 to 3 million pounds

were exported '(Ref. 16, Mobay, 1982).

The manufacturing process for HDI,

similar to that of other diisocyanates,

employs phosgenation of hexamethylene

diamine. In response to a request for

information, Mobay estimated that the

quantity of HDI that enters the

-environment during production and use

does not exceed 20,000 pounds per year

(Ref. 16, Mobay, 1982).

HDI is used in the manufacture of

higher molecular weight biuret

polyisocyanate products. These.are

commercially used as curing agents in

the formulation of polyurethane paint

systems for.automobile refinishing,

industrial maintenance, marine coatings,.

and other higher performance coating

systems (Ref. 16, Mobay, 1982).

B. Evidence for Human and

Environmental Exposure

There is no OSHA permissible

exposure level (PEL) for HDI. In 1978,

NIOSH recommended that OSHA adopt

the same standard also recommended

for toluene diisocyanate (TDI) and

methylene diphenyldiisocyanate (MDI),

i.e., an 8-hour time-weighted average of

5 ppb (35 ug/m3 } (Ref. 22, NIOSH, 1978).

The recommended 10-minute short-term

exposure limit is 0.02 ppm (140 ug/m3)

(Ref. 22, NIOSH, 1978). ACGIH earlier

recommended the same levels (Ref. 1,

ACCII-, 1976). The level immediately

dangerous to life and health (IDLH),

beyond which irreversible health effects

are known to occur, is 10 ppm (Ref. 28,

Woolrich, 1982).

The National Occupational Hazard

Survey (NOHS), conducted by the

National Institute for Occupational

Safety and Health (NIOSH) from 1972 to

1974, estimated that about 4,490 workers

in 238 plants were exposed to HDI

through manufacture, processing, or use

in 1970. Of these, about 4,000 were

involved with coating applications (Ref.

21, NIOSH, 1976). NIOSH also

conducted a second workplace survey,

the National Occupational Exposure

Survey (NOES). from 1980 to 1983 (Ref.

23, NIOSH, 1984). Preliminary data from

the NOES indicated that 39 workers,

including 11 women, were potentially

exposed in 1980.

The number of workers exposed to

HDI is probably underestimated since it

is impossible to estimate the workers in

trade professions or other operations

using products containing HDI.

However, data indicate that coatings

applications provide the greatest source

of occupational exposure to HDI.

Information obtained from the iJnited

Auto Workers suggests that 1,000 to

10,000 workers are potentially exposed

to HDI-containing coatings and

adhesives in new car, manufacture (Ref.

26, UAW, 1988). The Automotive

Services Association estimated that

there are 60,000 to 100,000 private

autobody and repaint shops that usually

employ 1.5 to 12 persons each,

potentially exposing between 90,000 and

1.2 million persons (Ref. 4, ASA, 1988):

In a 1982 submission to the TSCA

Interagency Testing Committee, Mobay

estimated that 153,000 autobody repair

workers were potentially exposed to

HDI (Ref. 16, Mobay, 1982).

Information received from the

International Brotherhood of Painters

and Allied Trades (IBPAT) indicated

that about 60,000 union members use an

HDI-containing coating at least once a

year. HDI-containing coatings are used

several times a year by about 30,000

workers; 3,000 use HDI-containing paint

exclusively (Ref. 9, IBPAT, 1988). The

Communication Workers of America

indicated that about 51,000 of their

members are exposed to multiple

diisocyanates, including HDI. Of these,

about 45,000 telecommunications cable

splicers and outside plant technicians

work with plugging compounds

containing HDI. The remaining 6,000

workers are exposed to diisocyanatecontaining inks and RIM plastics {Ref. 5,

CWA, 1988).

The civilian and military aircraft'

industry uses aliphatic diisocyanatecontaining paint almost exclusively

because of its stability in ultraviolet

light (Ref. 8, Hulse, 1984). The number of

persons potentially exposed to HDI

through these occupations is not known

at this time.

In summary, excluding individuals

exposed through the aerospace

industries and the military, it appears

that between 265,000 and 1,315,000

workers are potentially exposed to HDIcontaining products.

Between 1978 and 1982, Mobay

conducted field industrial hygiene

surveys during spray applications of

HDI-containing paint systems. Data

gathered during six -different surveys

demonstrated HDI concentrations

between <0.005 ppm and 0.04 ppm (Ref.

16, Mobay,-1982). As shown in a section

8(d) submission from Mobay, oven

exhaust from a heat-cured urethane

resulted in monomeric HDI

concentrations of 230 ppb (Ref. 17,

Mobay, 1978). This level exceeded the

ACGIH threshold limit value (TLV) and

NIOSH recommended short-term

exposure limit (STEL) of 20 ppb by

about 11 times.

A study was conducted to determine

the airborne concentrations of total

reactive isocyanate groups (-NCOs)

from the application of consumeravailable polyurethane products. A twopart HDI-containing polyurethane'

enamel was used in a controlled area

simulating a workshop/garage. The

-product was sprayed on a metal

bookcase. Analyses of personal and

area air samples .collected during the

spray application of the enamel found -

NCO groups in excess of the upper limit

of detection, >5.0 mg NCO/m 3 or >2.9

ppm (Ref. 20, MRI, 1987). This level was

almost 300 times the NIOSHrecommended 10-minute STEL of 0.02

ppm.

II. Chemical Fate Information

Although HDI is likely to be released

to the environment, primarily in fugitive

air emissions, it is not expected to

persist and should be rapidly -

18200
Federal Register / VtL 53, No. 98 / Friday. May 20, 1988 J Notices

transformed, especially in the:presence JI. Biological Effectsof:Concern to B. Acute (short-term) Effects

of liquid water. Therefore, chemical fate Human Health The acute and subacute toxicity of

testing is not recommended at this time. A. Metabolism and Toxicdkinetics HDI are summarized in the .followig

Tables 3 :and 4.

No informationwas found.

,TABLE ,3.-CRITICAL END POINTS FOR THE ACUTE/SJBACIT-E Toxic .EFFECTS !OF IHDI

Critical toxic effect end points 1from multipledose/concentration

'Test Test subject .studies Reference

ILOELb iNOEL'

Skin irritation ............................. . . .... ..... "Guinea pig ................ I ............... 0A mg/anim l :0:2.mg/animal Kondrat'yev and Mustayev (1969, Ref. 13).

'(approx) (approx.)

Ocular irritation ............. ...... .. ......... Rabbit . ...... iNEd NE Mobay (1961, Ref. 1:5).

Sensory irritation ...... . . .... 'Male mouse ..... . . 0.062 ppm NE Sanglia etal. (1981.,:Ref. 24).

(0.43.mgZmr 3 I

Pulmonary irritation .................... Albino rat................. NE' NE Lomonova and Frolova (1968, -as cited in

NIOSH, 1,978, Rdf. 2?2).

Pulmonary irritation .................... Rabbit ...................... NE NE ;Frolovaya (1966, 1-968, ,asoited in Kondrat'yev

and Mustayev 1969, ,fef. 13).

Contact :sensitivity, ,induction ...................... Male mouse .............. 8 ug/aimal 2.1 ug/animal Thorne et al. (1987, Ref. 25).

!(0.281mg/kg) i(0:075 mg/

I kg)

Contact sensitivity induction .............................. G inea pig ................................. INE INE Kondrat'yev end Mustayev '(1969, Retf. 13).

Contact sensitivity elicitation .......................... Guinea pig..... ............................. Bug/animal , NE Kondrat'yev and .Mustayev k(,1969, Ref. 13).

(approx)

Contact sensitivity elicitation ................................. Male mouse ........................... NE IE Thorne et al. (1987, Ref. 25).

,*With the exception of the mice used in .the Sangha et al. .(1981) study, 1test animal parameters such as sex, age, weight, and strain were not reported. b Lowestobservable-effects level.

cNo-ooservable-etfects level.

NE, not -established inthis study.

TABLE 4.-ACUTE TOXICI.TY'OF HDI IN :LABORATORY ANIMALS

LC50

Species -Concentration Duration (hours) Reference

'Oral '(mg/kg) 'Dermal (mg/kg) (mg/m 3 ) (ppm)

Rat ......... ...... 385 56 6 710 ................. 'Woolrich'(1982, 'Ref. 28).

Rat (M .. 310 45 4 .............................. 'Bunge;et al. ,(1977, as citedinNIOSH, 1 978, Ref..22).

Rat (F) ....................... 350 51 4 ............................ 'Bungeet.al. (1977, asicited in NIOSH, 1978,,Ref.,22).

Rat ....................... ................. i;5 ............... Mobay '(l1961, Ref. 15).

Mouse ...................... 30 4 ;2 .............................................. .... :Lomonova and Frolova '(1968, ascited

in INIOSH, ;1978,iRef.'22). Rabbit ........ ............ ... ................ ... ..... ... . ................ J.... .. ....... ....................... ................................ ..... 570 W oolrich (4 182, ,Ref. 28).

Rabbit [--- - . . . . I ............ . . . . . . . . . . .15).

Single dermal doses of -1,000 lo 1:250 mg/kg caused lethality, damage to subcutaneous 'layers iof skin, and systemic injury including -extensive pulmonary

congestion.

HDI is known to produce irritation

and inflammation of the upper

respiratory tract, so-called sensory

irritation. Sangha et al. '(Ref. 24, 1981j

conducted an acute inhalation study

with mice. Depression ofthe respiratory

rate was observed at the lowestdose of

EDI tested,,62 ppb (0.43 .mg/m 3). No

LOEL was established.

Experiments dealing with the

eiicitation of dermal HDI

hypersensitivity were performed early in

the study ofdiisocyanates. A 'key study

with guinea pigs pnbulished in 1969 by

Kondra't'yev and'Mustayev 'Ref. 13,

1969) provided a LOEL of'8 ug per

animal. Since this is the lowest dose that

has been tested in this manner, it 'is

clear that a NOEL has iot yetbeen

established.

Thorne et al. (Ref. '25, 1-987.) induced

dermal sensitization to ,HDI in mice by

application 'of a single 'dose to shaved

abdominal ,skin. 'Sensitizabion was

demonstrated bya sgingle challenge ,does

to the ear. The'SD5 0 (does predicted to

sensitize 50 percent of the animals) upon

homologous challenge for HDI ,was 0.088

mg/kg. TheLOEL for HDI was 8,ug per

animal; the)NOEL was 2.1 ug,per animal.

C. Genotoxicity.

In the Salmonella assay,' HDI wasnot

mutagenic in ,Strains TAIOO, TA98, or

TA1537 with or without metabolic

activation. A'wide dose'range, up to the

highest noninhiblitory dose, was'used

(Ref. 3, Andetsen et al., 1980). HDIis

also reported to 'inhibit mulagenesis

induced 'by ultraviolet light in an

Esc herichia col wild-type strain but not

in DNA-repair-enzyme deficient strain

(Ref. 12, Kawazoeet al., 1981

1 18201
Federal Register /. Vol. 53, No. 98 / Friday, May 20, 1988 / Notices

D. Oncogenicity

The Mobay Corporation is conducting

a 2-year inhalation toxicity/

oncogenicity study for HDI. Male and

female Fischer 344 rats were exposed to

0, 0.005, 0.025, and 0.125 ppm for 0 to 4

months and to 0.175 ppm thereafter. The

exposure regimen was 6 hours per day, 5

days per week for approximately 24

months.

Sixty rats of each sex were exposed at

each level, and 10 rats of each sex at

each level for a satellite group.

Preliminary review of the data indicated

no toxicologically significant effects on

body weight, ophthalmology or

mortality; no other parameters were.

evaluated. The final report is scheduled

to be completed during mid-1989 (Ref.

18, Mobay, 1988a).

E. Chronic (Longterm) Effects

No information was found.

F. Reproductive and Developmental,

Effects

No information was found.

G. Observations in Humans

Allegations of adverse health effects

following exposure to HDI (and other

diisocyanates) were the subject of a

TSCA section 8(c) reporting rule (53. FR

1408; January 19, 1988). The rule required

only submission of unknown or

unreported adverse health effects.

Several of these involved a two-part

polyurethane enamel. The activator for

this enamel contains over 70 percent

HDI-polyisocyanate. According to the

Material Safety Data Sheet, HDI

monomer is controlled to <0.7 percent

by weight. With aging, the monomer

content may increase to 1.6 percent by

weight (Ref. 6, Dupont, 1981.) One case study describes an

individual who inadvertently stepped

into a puddle of two-part polyurethane

enamel. This person began to

experience immediate "trouble", which

gradually worsened to a burning

sensation up to mid thigh with aching

discomfort and mild weakness in foot

muscles. Another case associated "

exposure to the two-part polyurethane

enamel with subsequent testicular

cancer and terminal chest cancer. A,

third case involved 12 men employed in

an unspecified job; all experienced

urologicail problems allegedly due to

exposure to this enamel (Ref. 7, Dupont,

1988).

Another reported incident involved

firefighters exposed to the two-part

polyurethane enamel. This paint was

used in firehouses inBalitmore, MD

between January 1982 and March 1984.

Of 10 infants fathered during this 15-

month interval, 8 died during

spontaneous abortion or soon after

birth. A similar report involved a man

employed in an autobody shop and

exposed to this enamel. He claimed that

his exposure prior to and subsequent to

the conception of his son was

responsible for severe birth defects (Ref.

7, Dupont, 1988).

Many case-specific reports suggest

adverse health effects following

exposure to polymeric HDI. Of

particular note is a case described by

Malo et al. (1983, as cited in Karol, 1987,

Ref. 11), in which an individual exposed

to a spray paint containing polymeric

HDI experienced shortness of breath,

wheezing, malaise, and chills late in the

afternoon on working days. Symptoms

lasted for several hours and were

accompanied by wheezing at night.

Inhalation challenge under simulated

occupational exposure conditions

reproduced the symptoms and thereby

identified the source of the active

material.

A recently published study of Swedish

car painters exposed both to HDI and

biuret-modified HDI at average

concentrations of 0.001 ppm and 0.013

ppm, respectively, demonstrated that

pulmonary closing volume was

increased in car painters relative to vital

capacity; controls did not exhibit this

decrement. The authors found this

suggestive of "small airways disease"

(Ref. 2, Alexandersson et al., 1987).

H. Rationale for Health Effects

Recommendations.

Annual domestic production of HDI is

about 11 million pounds. It is estimated

that well over 1 million individuals are

exposed to this chemical in the

workplace, as a result of its use in

coatings. Although one carcinogenicity

study is currently being conducted in

one rodent species, data are not

available to assess fully the long-term

effects of HDI. Therefore, the Committee

recommends that chronic toxicity

studies with carcinogenicity as an

endpoint be conducted in another

species in accordance with accepted

guidelines for carcinogenicity testing;

The Committee also is concerned about

available human data suggesting

potential reproductive impairment.

Considering the lack 'of definitive

reproductive and developmental effects

data, the Commitee recommends that

testing addressing these specific

endpoints also be conducted.

IV. Ecological Effects of Concern

Since HDI is not expected to persist

following release to the environment

and should be rapidly transformed in

the presence of water, ecological effects

testing is not being recommended at this

'time.

References

(1) ACGIH. "Threshold Limit Values for

Chemical and Physical Agents, 1976,"

Cincinnati, OH: American Conference of.

Governmental Industrial Hygienists.

(2) Alexandersson, R., Plato, N.,

Hedenstierna, G., Kolmodin-Hedman, B.

"Exposure, lung function, and symptoms in car painters exposed to hexamethylenediisocyanate and biuret modified

hexamethylene-diisocyanate," Archives of

Environmental Health. 42:367-373 (1987).

(3) Andersen, M., Binderup, M.L., Kiel, P.,

Larsen, H. and Maxild, J. "Mutagenic action

of isocyanates used in the production of

polyurethanes," Scandinavian Journal Work

Environmental Health. 6:221-226 (1980).

(4) ASA. Personal communication from J.

Caldwell, former Executive Secretary,

Automotive Services Association (ASA),

Laguna, CA, to S' Strassman-Sundy, Risk

Analysis Branch, Office of Toxic Substances,

U.S. Environmental Protection Agency

(March 14, 1988).

(5) CWA. Letter from D. LeGrande,

Occupational Safety and Health Coordinator,

Communication Workers of America (CWA),

Washington, DC, to S. Strassman-Sundy, Risk

Analysis Branch. Office of Toxic Substances,

U.S. Environmental Protection Agency

(March 31, 1988).

(6) DuPont. Material Safety Data Sheet on 192S Activator. El.du Pont de Nemours &

Co., Inc.,(1981). . (7) DuPont: Section 8(c) submission number

8CL-0388-0002; E.I. du Pont de Nemours &

Co, Inc. (March 4, 1988).

.(8) Hulse, P.M. "An evaluation of HDI in

polyurethane. spray paint aerosols," Masters:

Thesis. The John Hopkins University,

Division of Environmental Health

Engineering, School of Hygiene & Public

Health. Baltimore, MD (1984).

(9) IBPAT. Personal communication from R.

Wolford Health and Safety Officer,

International Brotherhood of Painters and

Allied Trades (IBPAT), Washington, DC, to S.

Strassman-Sundy, Risk Analysis Branch,

Office of Toxic Substances, U.S.

Environmental Protection Agency (March 22,

1988).

(10) ICF. "Producers and Users of

Diisocyanates," Washington, DC: ICF

Incorporated, U.S. EPA Contract No. 68-02-

3976; Work Assignment No. 1-25 (June 30, 1986].

(11) Karol,'M.H. "Respiratory effects of

inhaled isocyanates," CRC Critical Reviews

in Toxicology. 16(4):349-379 (1987).

(12) Kawazoe, Y., Kato, M., and Takahashi,'

K. "Studies on chemical carcinogens. XX.

Inhibitory effect of alkyl isocyanates and

isothiocyanates on mutagenesis in E. coll by.

ultraviolet radiation," Chemicadl and

Pharmaceutical Bulletin. 29:2631-2638 (1981).

(13) Kondrat'yev, G.G., Mustayev; R.K.

"Study of the allergic properties of

hexamethylene-diisocyanate in an experiment," (Rus.) Gigiyena Primeneniya

Polimernykh Materialov i lzdeliy Iz Nikh.,

Nr. 1, pp. 290-293. Translated by: Translation

18202
Federal Register I Vol. 53,, No. 98 / Friday, May 20, 1988 / Notices

Division. Foreign Technology Division.

Wright Patterson AFB, Ohio (1969).

(14) Leo, A.R., Hansch. C., and Elkins, D.

"Partition coefficientsand their uses,"

Chemical Reviews. 71(6):525-615 f1971).

(15) Mobay. "ToxictyanaSafe~Handing.f

1socyanates. AReview nf the :Lterature,(TDl,}

and Resultsof Toxicity.Screening.Studies on

Additional Compounds," Pittsburgh, 'PA

Mobay Chemical Company (1961).

(16) Mobay. Letter from C.LH.Howard,

Vice President-Scientific, Mobay'Chemrical

Corporation to M. Greif, TSCA Interagency

Testing Committee (July 20,1982).

(17) Mobay. TSCA Section 8(d) submission

number 8-870001276; Mobay Corporation

(July 29,1987).

(18) Mobay. Letter from Franois J. Rattay,

Manager, Regulatory Compliance, Mobay

Corporation, Pittsburgh, PA, to Robert Brink,

TSCA Interagency Testing Committee

(January 21,1988a).

(19) Mobay.,Personal communication from

F.J. Rattay, Manager, Regulatory Compliance,

Mobay Corporation, Pittsburgh, PA, to R.

Wedge, Dynamac Corporation (March 14,

1988b).

(20) MRI. TotalJsocyanates'-ACE

Laboratory Experiment. Xansas City, MI:

Midwest Research Institute. U.S. EPA

Contract 68-02-4252; Work Assignment No.

51 (October 29, 1987)." " •

(21) NIOSH. National Occupational Hazard

Survey (1972-1974) [data base), Cincinnati,

OH: National Institute forOccupational

Safety and Health, Department ofHealth and

Human Services (1976).

(22) NIOSH. "Criteria fora recommended

standard occupational exposure to

diisocyanates," 'Rockville MD: National

Institute for Occupational'Safety -andHealth.

NIOSH-78-215. PB81-..26615 (1978].

(23) NIOSH. National Occupational

Exposure Survey (1980-1983) (data basej,.

Cincinnati, OH: National:Institute for.

Occupational Safety-and Health,,Department

of Health and Human Services :1984).

(24) Sangha, G.K., Matijak, M., Alarie, -Y.

"Comparison of some mono- and

diisocyanates as sensory irritants,"

Toxicology and Applied Pharmocolqgy.

57:241-246 11981).

(25) Thorne, cPS,, Hfllebrand, J.A., 'Lewis,

G.R., Karol, M.H. "Contact sensitivity by

diisocyanates:-Potencies and -crossreactivities," Toxicaqgy and Aplied

Pharmacology. 87:155-165 (1987).

(26) UAW. Personal communicationirom.F.

Mirer, Health and Safety Director, United

Auto Workers, Detroit,.Ml, to L Borghi,

Dynamac Corporation (March 16, 1988).

:(27) USEPA. TSCA Chemical Substance

Inventory (non-confidential) [data base].

Washington, DC: U.S. Environmental

ProtectionAgency !(19881.

'(28) Woolrich, P.F. "Toxicology, industrial

hygiene and medical control of TDI, MDI, and

PMPPI," American Industriot Hygiqne

journal. 43:89-97 (1982).

2.3 Chemicals recommended.with

intent-to-designate--.2.3a

Crotonaldehyde-Summary.of

recommended studies. It is

recommended that.crotonaldehyde be

tested for the.following:

1. Chemical fate: Volatilization rate

from water. Aerobic aquatic

biodegradation rate.

2. Health effects: None.

3. Ecological effects: Acute toxicity 'to

algae, fish, and aquatic invertebrates.

Physical and Chernical informa'ionCAS.Ntmber 170-30-3

Synonyims:2-iButenal ;9 CI);'B- MethyI

acrolein; Crotonal; Crotonic aldehyde;

Propylene aldehyde.

Structural Formula.'

CH3

CH=CHCHo

EmpiricalFormul'a: caL0

Molecular Weight:70.1

Melting,Point:.--76.5C I(Ref. 6,-Merck,

1983); -69*C (,Ref. 9, Sax -and Lewis.,

1987)

Boiling Point: 104.0°C (Ref. 6, Merck,

.1983); 102*C (Ref. 8, Sax and Lewis,

1987)

Vapor-Pressure: 30 nmHg -at 20*dC t(Ref.

8, Sax and Lewis, 1987);. 19 mmHg;at

20C (Ref. 11, Verschueren, 1983)

Solubility in .Water:T55 :g/L !at 209C

(Ref. 11, Verschueren, 4983); 18.1 -g1100

g at 20°C (Ref. 6, Merck,'1983). :

Specfic Gravity:'.853 at 20/20°C (.Ref.

Z,"Merck, 1983)

Log -Octano7/Water Partition

-Coefficient .(Iog P': 0.55 (Est'd; Ref. 7,

NRC, 19813

Henry's Law Constant: 1.7 .X 10 - 5atm

:m3/mole, ,calculated

Descrotionof.Chemica" Water white,

mobile 'liguid .wth a pungent,

suffocating odor (Ref. 8, Sax and -

: Lewis, 198)1

Rationale for Recommendation

L Exposure-Information

A. Production/Use/Release to

Environment

Most crotonaldehyde is manufactured

, from acetaldehyde usingcontinuous,

enclosed -reactor-systems via the aldol

condensation route, -although a variety

of less ,common'methods snay 'be used

(Ref. 4, Kirk-Othmer, 1979). Annual

currettand projected U:S. production -is

from 5,to'15 million pounds (Ref. 2,

Eastman Kodak, 1987). Crotonaldehyde

also maybe formed naturally in :the

atmosphere .by the interaction of

reactive molecules:such as ,ozone and

hydroxyl radicals -with hydrocarbons

and theirtoxidation products (Ref. 7,

NRC, 1981). Crotonaldehyde is rused

primarily as za,chemical intermediate for

the synthesis of other organic

compounds -such as a-butanol,,sorbic

acid, 3-methoxybutanal, and crotonic

acid;,(Ret 4, Kirk-Othmer, 1979].

Releases,ofrotonaldehyde ,to ,the

environment are expected to occurin

wastewater.

B. Evidence fariosure

Crotonaldehyde has :been.detected in

the effluent of sewage treatment plants

(Ref. 9,;Shackelford and.Keith, 1976].

Exhaustfrom cars Without emission

controls was found to contain

crotonaldebyde -(Ref. :., NRC, 1981').

Crotonaldehyde .als6,.has been identified

as a constituent df tobacco smoke '(Ref.

3, Florin et al., 1980) and wood smoke

(Ref. 5, :Lipari etal., 1984).

17. Chem'cal Fate Information

A. Transport

Environmental.-releases iare expected

to be from wastewater. The physical -

and chemical prqpertiesof

crotonaldehyde indicate -that-it will

partition tobotbairand water following

release to -the environment. The Henry's

Law'Constantof-1:7 X 10-5 atm!m /

mole ,allows an estimation of the halflife in receiving-stream -water of-60 to 70

hours. Sorption tosolids will not be

significant.

B. Persistence

Crotonaldehyde released directly to

the atmosphere or evaporated from _

surface water will -be rapidlyidegraded

by reactions with lhydroxyl.radicals -and

ozone and by direct sunlight -photolysis.

Biodegradation isexpected to be the

most significant -transformation process

in water, :but no ,aquatic biodegradation

rate data were found.The 5-day '

biochemicaloxygen -demand (-BOD] :for

crolonaldehyde was reported as 37

percentof theory4(Ref. 11, Verschueren,

1983) and 51,percentof theory f-Ref. 10,

Union Carbide, 1986). The Union "

Carbide reference talso 'lists BOD data

after 10, 15, and 20 days incubation as 60

percent, 64 percent and 70 percent of

theory., respectivdly.'These data suggest

ready andcomplete biodegradation

when sewage or sludge, which-may be

acclimated-to crotonaldehyde, are-used

as the inoculum, but they do not permit

a determination -ofthebiodegradation

half-life in receiving systems.

C. Rationale forChemical Fate

Recommendation

Since crotonaldehyde maybe. ,

released to,sufiface waters at - -

manufacturing and, use sites, it is

necessary .to obtain.experimental data

on volatilization rates from water.and

on the aerobic,aquatic biodegrad-ition

rate to better assess ]potential

environmental concentrations.

-18203
18204 Federal Register / Vol. 53, No. 98 I Friday, May 20, 1988 I Notices.

III. Biological Effects of Concern to

Human Health

The Committee determined that

crotonaldehyde has been studied

extensively for health effects and

concluded that additional studies are

not required. Therefore, health effects

testing is not being recommended at this

time.

IV. Ecological Effects of Concern

A. Acute and Subchronic (Short-term)

Effects

An 85 percent aqueous solution of

crotonaldehyde produced a 96-hour LCo

of 3.5 mg/L to bluegills (Lepomis

.macrochirus) in a static bioassay at 20*

C (Ref. 1, Dawson et al., 1977). A 96-hour

LCo value of 2.8 mg/L with fathead

minnows (Pimephales promelas] was

reported by Union Carbide (Ref. 10,

1986). The 96-hour LC5o for tidewater

silversides (Menidia beryllina) was

reported to be 1.3 mg/L in a static

bioassay at 200 C (Ref. 1, Dawson et al.

1977). Percent survival of silversides

decreased with exposure time.

B. Chronic (long-term) Effects

No information was found.

C. Other Ecological Effects

Sewage treatment microorganisms

were reported to be adversely affected

by 25 to 50 mgfL crotonaldehyde (Ref.

10, Union Carbide, 1986). At

concentrations from 0.05 to 1.0 percent,

crotonaldehyde produced an immediate

loss of the metachronic wave in the

lateral cilia of freshwater mussels

(Lamellibranchiata unio) (Ref. 12,

Wynder et al., 1965). At the 0.5 aid 1.0

percent concentrations, total stasis in

mussel cilia was observed, with no

recovery.

D. Bioconcentration and Food-Chain

Transport

No information was found, but the

high water solubility and low log P of

crotonaldehyde make it unlikely that

any sigificant bioconcentration will

occur.

E. Rationale for Ecological Effects

Recommendation

The available data, from tests using

nominal concentrations in static tests,

show that crotonaldehyde has

significant acute toxicity to both

freshwater and marine fish. It is

necessary to develop more reliable

acute toxicity data using measured

concentrations of crotonaldehyde in

flow-through or static-renewal tests,

using algae, fish, and aquatic,

inverte'rates.

* References

(1) Dawson, G.W., Jennings, A.L.

Drozdowski, D., Rider, E. "The acute toxicity

of 47 industrial chemicals to fresh and

saltwater fishes," Journal of Hazardous

Materials. 1:303-318 (1977).

(2) Eastman Kodak. Letter from R.D.

Gerwe, Senior Product Safety Representative;

Eastman Kodak Co., Kingsport, TN to R.H.

Brink, TSCA Interagency Testing Committee

(June 19,1987].

(3] Florin, ., Rutberg, L., Curvall, M., and

Enzell, C.R. "Screening of tobacco smoke

constituents for mutagenicity using the Ames'

test," Toxicology. 18:219-232 (1980).

(4] Kirk-Othmer. Kirk-Othmer

Encyclopedia of Chemical Technology. New

York, NY: John Wiley & Sons, Inc. Vol. 7, pp.

207-218 (1979).

(5] Lipari, F., Dasch, J.M., Scruggs, W.F.

"Aldehyde emissions-from wood-burning

fireplaces," Environmental Science and

Technology. 18(5):326-330 (1984).

(6] Merck. The Merck Index. 10th Ed.

Windholz, M., ed. Rahway, NJ: Merck &

Company. p. 372 (1983).

( (7) NRC. National Research Council.

Formaldehyde and Other Aldehydes.

Washington, DC: National Academy Press

(1981].

(8] Sax, N.I. and Lewis, R.J., Sr. Howley's

Condensed Chemical Dictionary. 11th Rev.

Ed. New York, NY: Van Nostrand Reinhold

Co. p. 323 (1987).

(9] Shackelford, W.M., Keith, L.H.

"Frequency of organic compounds identified

in water," Athens, GA: U.S. Environmental

Protection Agency, Environmental Research

Laboratory. EPA Report No. EPA-600/4-76-

062. p. 102 (1976].

(10] Union Carbide. Letter from D.L.

Heywood, Assistant Director, Product Safety,

Union Carbide Corp., Danbury, CT to U.S.

Environmental ProtectiomAgency (May 2,

1986].

(11) Verschueren, K. Handbook of

Environmental Data on Organic Chemicals.

2nd Ed. New York, NY: Van Nostrand

Reinhold Co. pp. 410-411 (1983).

(12] Wynder, E.L., Goodman, D.A.,

Hoffmann. D. "Ciliatoxic components in

cigarette smoke. 11. Carboxylic acids and

aldehydes," Cancer. 18(4):505-509 (1965).

2.4. Chemicals recommended without

being designated for -response within 12

months-2.4.a Imidazolium quaternary

ammonium compounds-Summary of

recommended studies. It is

recommended that the imidazolium

quaternary ammonium compounds, 4,5-

dihydro-1-methyl-2-nortallow alkyl-l-(2-

tallow amidoethyl], methyl sulfates

(IQAC) be tested for the following:

1. Chemical fate: Aerobic and

anaerobic biodegradation of IQAC

sorbed to freshwater and estuarine

sediments.

2. Health effects: Chronic toxicity

studies to evaluate potential effects

through long-term dermal exposure.

3. Ecological effects: Acute' and

chronic studies to evaluate effects on

representative freshwater and estuarine

benthic organisms.

Physical and Chemical Information

CAS Number: 68122-86-1

9 C!Nane: Imidazolium compounds, 4,5-

dihydro-l-methyl-2-nortallow alkyl-1-

(2-tallow amidoethyl), Me sulfates

Synonym: Imidazolium quaternary

ammonium compounds

Acronym: "IQAC

Structural Formula:

R-C

0

CH3 C 2CH 2NHC-R

/ N CH 2

I

CH 2

where R=tallow

Empirical Formula (typically):

C37H74N30 to C41 H82N30

Molecular Weight: 577.0 for R = C 15H3,:

633.1 for R=C17 -3 5

Boiling Point: <260C (Ref. 3, Capital

Citq, Products, 1986)

Solubility in Water: 19.2 mg/L in

deionized water after 16 days of

continuous mixing; 0.5 mg/L in filtered

river water after 16 days of

continuous mixing. (Ref. 4, Procter and

Gamble, 1984a)

Specific Gravity: No information was

found.

Log Octanol/Water Partition

Coefficient (log P): 215, measured

(Ref. 4, Proter and GCmble, 1984a)

Rationale for Recommendations

I. Exposure Information

A. Production/Use/Release to

Environment

IQAC production in 1984 was

estimated at about 15 million pounds in

the U.S. (Ref., 4, Procter and Gamble,

1984a). The TSCA Inventory update

contains confidential 1986 production

information for IQAC. The major use of

IQAC appears to be in fabric softeners

used during the clothes-washing

process. Analogs of IQAC that might

also be used in fabric softener

formulations include chemical mixtures

with the following CAS Nos.: 68132-27-

4, 69011-82-1, 70775-90-5, 71060-67-8,

71060-68-9, 72275-90-2, 72623-81-5 and

72623-82-6. If these compounds or

18204 J ' Federal Register / Vol. 53, No. 98 / Friday, May 20, 1988 / Notices,
Federal' Register / Vol. 53, No.' 98 / Friday, May 20, 1988 / Notices

similar imidazolium quaternary

ammonium compounds are used now, or

in the future, in substantial quantities as

ingredients in fabric softeners for

consumer use, the Committee would

have the same environmental fate,

health effects and ecological effects

concerns for them as for IQAC. IQAC

and any of its analogs used in fabric

softeners are likely to be released to the

environment in wastewater following

their use.

B. Evidence for Exposure

General population exposure to IQAC

may be high given its use in fabric

softeners used in laundry washing

machines. Consumers who use this type

of fabric softener are likely to be

exposed almost continuously through

skin contact with clothing, towels and

linens: An assessment by the Office of

Toxic Substances (Ref. 1, Battin, 1988a)

estimated annual consumer dermal

exposure to IQAC, from exposure to

softened clothing, linens, etc., at 4.06 to

10.14 g per year. Procter and Gamble

(Ref. 4, 1984a) estimated daily consumer

exposure to IQAC, from clothing to skin,

to be 0.07 mg active compound per kg

per day for adults and 0.14 mg active

compound per kg per day for children

assuming IQAC is deposited on fabrics

at 0.17 mg/in2. No environmental

monitoring studies were found. An

assessment by the Office of Toxic

Substances (Ref. 1, Battin, 1988a)

estimated receiving stream

concentrations of 1 to 1,300 ug/L at

manufacturing sites and 0.05 to 50 ug/L

near use sites, depending upon location

and stream flows. Procter and Gamble

(Ref. 4, 1984a) estimated that consumer

use of IQAC would yield raw

wastewater concentrations of about 170

ug/L.

II. Chemical Fate Information

A. Transport

The physical and chemical-properties

of IQAC indicate that it will partition

significantly to sludge solids and

sediments with some remaining

dissolved in water. The estimated very

low vapor pressure and moderate

solubility rule out volatilization as an

important factor. The cationic nature of

these compounds will contribute to their

sorption to sludge and sediment solids

which generally are negatively charged

and it is expected that IQAC will sorb to

solids within a short time after release

to the environment.

B. Persistence

No published information was found

on the persistence of IQAC. A summary

report of an unpublished study (Ref. 4,

Procter and Gamble, 1984a) showed

about 50 percent biodegradation in 34

days in diluted activated sludge, as

determined by following the evolution of

radiolabelled carbon dixoide. The

concentration of IQAC Was not I

reported. BOD studies reported by

Sherex (Ref. 6, 1984) showed 2 percent

of theoretical oxygen uptake after 5

days and 19 percent after 30 days. While

this indicates that IQAC is

biodegradable under aerobic conditions,

it also indicates that biodegradation in

surface waters is likely to be slow.

IQAC is expected to partition

significantly to sediments following

release to the environment and its

persistence in sediments, under both

aerobic and anaerobic conditions, is

unknown. Also unknown is the

persistence of IQAC under conditions

found in estuaries and the ocean.

Persistence in saline waters may be

different than in fresh water.

Nitrilotriacetic acid, for example, was

found to be resistant to biodegradation

in estuarine waters (Ref. 2, Bourquin and

Przybyszewski, 1977) although it is

readily biodegraded by acclimated'

microorganisms in fresh water.

C. Rationale for Chemical Fate

Recommendations

'IQAC is likely to sorb strongly to

waste treatment sludges and receiving

stream organic sediments and may

persist for relatively long time periods

following sorption. Since it is being

released continuously to both fresh

water and estuarine receiving waters

and may persist for relatively long

periods of time, there may be a tendency

for it to accumulate in estuarine, river

and lake sediments near discharge

points, with gradually increasing

concentrations. There is a need to better

determine the persistence of IQAC,

dissolved in water and sorbed to

sediments. It is recommended that those

studies be conducted under conditions

typical of both-fresh surface waters and

estuarine waters and that studies with

IQAC sorbed to sediment be conducted

under both aerobic and anaerobic

conditions.Information from these

studies is needed to better assess.the

potential concentration of IQAC in

receiving waters'and sediment and the

potential hazard to aquatic and benthic

organisms.

III. Biological Effects of Concern to:

Human Health

A. Metabolism and Toxicokinetics

A summary of metabolism studies

(Ref. 4, Procter and Gamble, 1984a)

using radiolabelled IQAC (

1 C on the Nmethyl group) suggests that the

compound is poorly absorbed in rats via

both oral and dermal routes. Upon oral

administration, less than 1 percent of the

oral dose was absorbed and

metabolized. Eighty-seven percent of the

oral dose was eliminated in feces within

24 hours. A "small but significant

amount of radioactivity was found in the

bone marrow" (Ref. 4, Procter and

Gamble, 1948a. Less than 0.5 percent of

the dermal dose was absorbed, with a

small amount of radioactivity found in

the bone mairow.

B. Acute and Subchronic (Short-term)

Effects.

Summary reports on unpublished data

from acute oral, dermal skin irritation,

eye irritation, skin sensitization, and

subchronic toxicity studies with IQAC

were submitted by Procter and Gamble

(Ref. 4, 1984a and Ref. 5, 1988). Data

from acute oral, skin and eye irritation,

and skin sensitization studies were

submitted by Sherex (Ref. 6, 1984).

Acute oral tests with IQAC in rats

yielded an LDso of 20.8 gfkg in one test

(Ref. 6, Sherex, 1984) and 2 deaths out of

10 in another test at a dose level of

about 18 g active compound per kg (Ref.

4, Procter and Gamble, 1984a). In

another study, no deaths were reported

with oral doses up to 16 cc of IQAC

dispersion (13.5 wt percent solid) per kg

(Ref. 6, Sherex, 1984).

Procter and Gamble reported

moderate to sev6re irritation for IQAC

instilled into the conjunctival sac of

rabbit eyes unrinsed after treatment

(Ref. 4, 1984a). However, it produced

minimal irritation to rinsed rabbit eyes

(Ref. 4, Procter and Gamble, 1984a; Ref.

6, Sherex, 1984).

Percutaneous studies with IQAC in

rabbits yielded a minimum lethal dose

of greater than 1.8 g active compound

per kg (Ref. 4, Procter and Gamble,

1984a).

Primary skin irritation studies

conducted with IQAC on intact and

abraded rabbit skin indicated moderate

to severe irritation in one study (Ref. 4,

Procter and Gamble, 1984a) and only

mild irritation in another (Ref. 6, Sherex,

1984).

Skin sensitization studies with IQAC

by Procter and Gamble (Ref. 4, 1984a)

showed delayed contact

hypersensitivity in 17 out of 20 guinea

pigs tested. Sherex (Ref. 6, 1984), on the

other hand, reported that IQAC was not

a strong sensitizer in guinea pigs tested

with three different lots. *

In a subchronic toxicity study (Ref. 4,

Procter and.Gamble, 1984a) four groups

of 20 male and -20 female rats each were

fed a diet containing IQAC at

concentrations of 0, 10, 100, or 1,000 mg

18205
Federal Register / Vol. 53,. No. 98, / Friday, May 20; 1988, / Notices

active compound per kg per' day for 13'

weeks. There were no' treatment-related

changes in mean body' weights or food

consumption. Lower total, protein and

higher serum glutamic-pyruvictransamihase values were observed in

blood samples of males in the 1,000mg

per kg:group. These males also showed

lower absolute and relative liver

weights. No treatment-related changes

were observed in bone marrow. The noobservable-effects level (NOEL) was 100

mg per kg per day. According to Procter

and Gamble, this level is at least 10

million times the expected daily human,

exposure to IQAC in drinking water.

In a percutaneous subchronic toxicity

test, two groups of 5 male and 5 female

rabbits each were treated topically with

2 mL per kg per day IQAC at dose levels

of 3, or 27 mg. active compound per kg

per day for 13 weeks (Ref. 4, Procter: and

Gamble, 1984a). A control group of 5

males and 5 females received the

vehicle, distilled water. Slight to

moderate erythema, edema, and

desquamation were. observed in treated

animals at both doses. No treatmentrelated changes were: observed in

clinical pathology, bone marrow smears,

body weights, organ weights,

microscopic. changes in skin, or

histopathologic changes to.internal

organs.. The NOEL for systemic toxicity,

was. 27 mg active compound kg per day.

C. Genotoxicity

IQAC was tested for mutagenicity'in

the Salmonella assay (with and without

metabolic: activation), mouse lymphoma

assay, rat in vitro cytogenetics assay,

and for'unscheduled DNA synthesis in

human diploid cells (Ref. 4, Procter and

Gamble, 1984a). IQAC did. not show

mutagenic effects in any of the assays.

D. Oncogenicity

No information was found.

E. Reproductive and Developmental

Effects

Rats, were administered IQAC' (78

percent' active compound) by-gavage at

dose levels of 200 of 600"mg active.

compound per kg daily from days 6 to 12

or 15.of gestation (Ref. 4, Procter and.

Gamble. 1984a). Acontrol groupreceived the vehicle, 15 percent w/v

aqueous isopropanol. Doses: were given.

to each group of'30 females at a constant.

volume of '2mL per kg per day.. The

animals were observed' for mortality,

clinical signs, body weight changes, and

food consumption. No maternal deaths

were observed. A decrease in food

consumption, was found in the 600'mg

per kg per day'group during the first 3

days. Overall' reproduction parameters

and pregnancy'rates-were unaffectedt

The incidences of skeletal and softtissue defects were not significantly-

'different between the'treated and the,

control groups. At the highest dose

tested.(600'mg active compound per kg

per day) no maternal' or. developmental

toxicity was observed.

F. Chronic. (Long-term) Effects

No information was found.

G. Observations in Humans

Little or no irritation was observed

with human volunteers in a skin

irritation test' with a dilute, aqueous

dispersion of 0.3 mL IQAC per occluded

patch (Ref. 4, Procterand Gamble,

1984a). IQAC was tested in, three 24-

hour exposures over a 6-day period at

concentrations of 0.5, 1.0, and 5.0

percent w/v. In another Procter and

Gamble study (Ref. 4, 1984a), 217

volunteers received 9 exposures to 0.25

percent w'/y aqueous IQAC (0.3 mL per

occluded patch) applied for a 24-hour

period, 3 times a week during a 3-week

induction period. No skin sensitization

was observed when subjects were

challenged 2 weeks later with 0.25

percent w/v IQAC in a, single 24-hour

occluded .patch test,

H. Rationale for Health Effects

Recommendations'

It has been estimated that fabric

softeners that are applied to the, fabrics:

during the washing process: are widely

used in' the U.S. Annual U.S.

consumption of imidazolium quaternary

ammonium type fabric softeners has

been estimated at about 15 million

pounds. It is quite apparent that asignificant portion of the population is

exposed, on a nearly' continuous basis,

to these chemicals in clothing, towels

and bed linens. Dermal exposure tests

reported to date have'involved only

acute or short-term exposures. IQAC

produced moderate to severe skin

irritation in rabbits and was a skin

sensitizer in guinea pigs.

Although exposure. concentrations.

used in short-term studies were'reported

to be severalfold higher than estimated

human exposures from softened fabrics,

information from these short-term,

intermittent-exposure tests is not useful

in predicting what effects might occur

with long-term (years)' continuous

exposure' It is therefore recommended

that IQAC and commercially important.

analogs be testedfor chronic. toxicity to

evaluate: potential effects, resulting from

long-term dermal exposure.

IV. Ecological Effects of Concern

A. Acute and Subchronic, (Short-term)

Effects,.

Data submitted by'Procter and

Gamble (Ref* 4 1984a) show moderate

toxicity to bluegills, mysid shrimp and

Daphnia magna. The presence of

anionic surfactants- or the. use of natural

surface water with sediments mitigated

the effects on bluegills and daphnia. No'

data were found for benthic organisms

and this is a data gap of concern since

IQAC will. sorb to and may concentrate

in sediments, near wastewater discharge

sites.

B. Chronic (Long-term) Effects

No! published information was found

but Procter and Gamble (Ref. 5, 1988)

indicated that data have: been. developed

with a hydrogenated analog of IQAC in

chronic, studies. with- midge.

C. Other Ecologica*l Effects (Biological,

Behavioral, or'Ecosystem Processes).

IQAC was' reported (Ref. 4, Procter

and' Gamble, 1984a) to, inhibit algal

growth at relatively low concentrations

The algistatic' concentrations were 0.037

mg/L.for a Selenastrumsp. and 0.23 mg/

L for a Microcystis sp.

D. Bioconcentration.and'Food-chain

Transport,

The measured log P of 2.15 indicates a

potential, for some bioconcentration.

Procter and.. Gamble (Ref. 4, 1984a)

reported a measured bioconcentration

factor (BCF) of 10.7 for bluegills exposed

to 8.8,g/LIQACiin a flow-through

system. This report is. suspect because

the reported concentration of IQAC is

well above its water solubility.

Nevertheless,, the evidence is that there

may be some bioconcentration.

E. Rationale for Ecological Effects

Recommendations.

Environmental fate considerations

indicated that IQAC will sorb strongly

to sludge solids and sediments., It may

persist for relatively long, time. periods

under these conditions and may

accumulate in sediments near

wastewater discharges. This

information plus- the known toxicity of

IQAC to fish, aquatic invertebrates, and

algae;, raise: concerns for benthic

organisms, Acute-toxicity, data should.

be obtained for representative

freshwater and estuarine benthic

organisms and, if these compounds are

found, to be relatively persistent, chronic

studies, on, the, same organisms may be

warranted.

18206 -
Federal Register / Vol. 53, No. 98 / Friday, May 20, 1988 / Notices

References

(1) Battin, A. Memorandum on exposure

and release of imidazolium quaternary

ammonium compounds in liquid fabric

softeners from Andrew Battin, Exposure

Assessment Branch, Office of Toxic

Substances, U.S. Environmental Protection

Agency, to John D. Walker, Test Rules

Development Branch. (February 2, 1988a.)

(2) Bourquin, A.W. and Przybyszewski,

V.A. "Distribution of bacteria and

nitrilotriacetate-degrading potential in an estuarine environment." Applied and

Environmental Microbiology. 34:411-418

(1977).

(3] Capital City Products. Material Safety

Data Sheet on Accosoft 808 75 and product

literature submitted by Capital CityProducts,

Janesville, WI (November 12, 1986).,

(4) Procter and Gamble. Letter from T.W.

Mooney, Manager, Technical Government

Relations, The Procter and Gamble Co.,

Cincinnati, OH, to Arthur Stern, TSCA

Interagency Testing Committee. (September

12, 1984a.)

(5) Procter and Gamble. Letter from R.N.

Sturm, Associate Director, Bar Soap &

Household Cleaning Product Development,

Procter and Gamble Co., Cincinnati, OH, to

Robert Brink, TSCA Interagency Testing

Committee (April 19, 1988).

(6) Sherex. Letter from Howard H.

Hickman, Manager of Regulatory Affairs,

Sherex Chemical Co., Dublin, OH, to Martin

Greif, TSCA Interagency Testing Committee.

(January 17,1984.)

2.4.b - Ethoxylated quaternary

ammonium compounds-Summary of

recommended studies. It is

recommended that ethoxylated

quaternary ammonium compounds, EEQ

(CAS No. 68153-35-5) and PEQ (CAS

No. 68410-69-5) and any commercially

important analogs of PEQ (e.g., CAS

Nos. 68389-88-8, 68389-89-9, 68413-44-7,

68554-06-3 and 70914-06-3) be tested for

the following:

1. Chemical fate: Aerobic and

anaerobic biodegradation of the

ethoxylated quaternary ammonium

compounds sorbed to freshwater and

estuarine sediments.

2. Health effects: Chronic toxicity

studies to evaluate potential effects

through long-term dermal exposure.

3. Ecological effects: Acute and

chronic effects on representative

freshwater and estuarine benthic

organisms. •

Physical and Chemical Information

CAS No.: 68153-35-5

9 CI Name: Ethanaminium, 2-amino-N-

(2-aminoethyl)-N-(2-hydroxyethyl)-

N-methyl-, N,N'-ditallow acyl

derivs., Me sulfates (salts)

Synonyms:

Ethoxylated ethanaminium quaternary

ammonium compounds;

N,N-Bis(2-tallow amidoethyl)N-(2-

hydroxyethyl)-N-methylammonium

methyl sulfate;

N,N-Di(2-tallow amidoethyl)-N-(2-

hydroxyethyl)-N-methylamm~nium

methyl sulfate;

Quaternary ammonium compounds,

(hydroxyethyl)-methylbis(2-tallow

amidoethyl), Me sulfates

Acronym: EEQ

Structural Formula:

O II CH, III O

R-C NHCHCH, - N- CH2CH2 NH C-R

CH2CH2OH

where R = tallow

Empirical Formula (typically):

C39 -1oN 30 3 to Q 3H 8 N30 3

Molecular Weight:

639.1 where R = C15113

695.5 where R = C17 -3 5

Melting Point: 170°C, estimated (Ref. 2,

Battin, 1988c)

Boiling Point: 567°C, estimated (Ref. 2,

Battin, 1988c)

Vapor Pressure: 2.86 X 10 - 7 mmHg at

25'C, estimated (Ref. 2, Battin,

1988c)

Solubility in Water: 35 mg/L in

deionized water after 14 days of

continuous mixing (Ref. 5, Procter

and Gamble, 1984b)

Specific Gravity: No information was

found.

Log OctanollWater Partition

Coefficient (log P): 2.48, measured

(Ref. 5, Proctor and Gamble, 1984b)

Henry's Law Constant: 7.71 x 10-19 atm

m3/mole, estimated (Ref. 2, Battin,

1988c)

Log Adsorption Coefficient (log Ko)s

2.27, estimated (Ref. 2, Battin, 1988c)

Physical and Chemical Information

CAS No.: 68410-69-5

9 CI Name: Poly(oxy-1,2-ethanediyl), a-

[2-[bis(2-

aminoethyl)methylammoniolethyl]-co-hydroxy-, N,N-ditallow

acyl derivs., Me sulfates (salts)

Synonyms:

Methyl tallow diethylenetriamine

condensate, polyethoxylated,

methyl sulfate;

Quaternary ammonium compounds,

(2-hydroxyethyl) methylbis(2-tallow

amidoethyl), Me sulfates,

ethoxylated

Acronym: PEQ

Structural Formula:

O UI CH, I o OII

R-CNHCHCH,- N- CHCH2 NHC-R

I

C H2C H20 (CH2CHO )H

where R== tallow and n=1-7

Empirical Formula (typically):

C41H84 N3 0 4 to C 57 Hi 16N 30 10

Molecular Weight:

683.2 where R=C5H31 and n=1

1,003.9 where R=C171-b and n=7

Melting Point: No information was

found.

Boiling Point: No information was

found.

Vapor Pressure: No information was

found.

Solubility in Water: No information Was

found. -

Solubility in Organic Solvents: No

information was found.

Specific Gravity: No information was

found.

Log Octanol/Water Partition

Coefficient (log P): No information

was found.

Henry's Law Constant: No information was found.

Log Adsorption Coefficient (log Koc): No . information was found.

Rationale for Recommendations

I. Exposure Information

A. Production/Use/Environmental

Release

It was estimated that the market for

EEQ in 1984 was about 25 million

pounds per year in the U.S. (Ref. 5,

Procter and Gamble, 1984b). Information

obtained during the ITC review of these

chemicals indicated that in recent years

PEQ has taken a large share of the

market away from EEQ. TSCA

Inventory update information contains a

total for 1986 production and import of

EEQ that is classified as confidential

business information (CBI). Production

and import of PEQ was not reported for

the TSCA Inventory update. The lack of

PEQ data in the updated Inventory

contrasts with reports (to Dynamac

Corp.) from industry of substantial

current PEQ production. The Committee

is unable to obtain current production

and import data for PEQ and its analogs

because they are classified as polymers

and are exempt from Inventory update

reporting. However, because of the

potential for widespread chronic

expbsures they are all recommended for

testing. - The major use for both EEQ and PEQ

is in fabric softeners for industrial and

consumer applications. Consumer

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Federal Register / Vol. 53, No. 98 / Friday, May 20, 1988 / Notices

product formulations typically contain

from 3.5 to 8 percent dispersions of the

active ingredient. EEQ also is reported

to be used as an anti-static agent,

corrosioncontrol agent, foam stabilizer

and emulsifier (Ref. 5, Procter and

Gamble 1984b). During and after use,

these compounds will be released to the

environment, mostly in wastewater from

clothes-washing operations.

Analogs of PEQ, which also) may be

used as fabric softeners, and that are

included in the recommended testing,

are shown in the following Table 5:

TABLE 5-ADDITIONAL ETHOXYLATED

QUATERNARY AMMONIUM COMPOUNDS

RECOMMENDED FOR TESTING IF USED

IN SUBSTANTIAL QUANTITIES IN FABRIC

SOFTENING APPLICATIONS

CAS No.

68389-88-8

68389-89-9

68413-04-7

68554-06-3

70914-09-9

Chemical name

Poly(oxy- 1,2-ethanediyl), a-[2-[bis(2-

aminoethyl)methylammonio] ethyl] -

w-hydroxy-, NN-dicoco acyl

derivs., Me sulfates (salts)

Poly(oxy-1,2.ethanediyl), a-[2-[bis(2-

aminoethyl)methylammonio]ethyl]-

o-hydroxy-, N,N'-bis(hydrogenated

tallow acyl) derivs., Me sulfates

(salts)

Poly[oxy(methyl-1,2-ethanediyl)], a-

(2-(bis(2-

aminoethyl)methylammoniolmethylethyl-w-hydroxy-, NN-ditallow acyl

denvs..

Poly(oxy-1,2-ethanediyl), a-[3-[bis(2-

aminoethyl)methylammonioj-2-

hydroxypropyll-w-hydroxy-, N-coco

acyl denvs., Me sulfates (salts)

Poly(oxy-1,2-ethanediyl), a-[2[bis(2-

aminoethyl)methylammonio] ethyl) -

w-hydroxy-, N,N'-di-C ,-,. acyl

derivs., Me sulfates (salts)

. Evidence for Exposure

i. Evidence for human exposure.

General population exposure to PEQ

may be high given itsuse in fabric

softeners. Ethoxylated quaternary

ammonium fabric softeners are used in

detergent formulations and in products

designed for addition to washing

machines prior to the last deep rinse of

the wash cycle. The major route of

exposure is skin contact with fabrics

that have been treated with the fabric

softener. Consumers who use these

types- of fabric softeners are likely to be

exposed almost continuously- through

skin contact with clothing, towels and

bed linens. Procter and Gamble (Ref. 5,

1984b) estimated daily consumer

exposure to a "similar compound," fromclothing to skin to be 0.07 mg active

compound per kg per day for-adults and

0.14 mg active compound per kg per dayfor children, assuming EEQ is deposited.

on fabrics at 0.17mg/in2. Sherex (Ref. 8,

1987) indicated that PEQ and EEQ are

similar chemically and with respect to

use. Tiferefore, the exposure estimates

made by Procter and Gamble for EEQ

appear to be applicable to PEQ.

An assessment by the Office of Toxic

Substances (Ref. 1, Battin, 1988b)

estimated annual consumer dermal

exposure to this kind of compound, from

exposure to softened clothing, linens,

etc, at 1.08 to 2.69 g per year. Human

exposure via drinking water is not

expected to be significant. The

ethoxylated quaternary ammonium

compounds are expected to sorb

strongly to sediments and other solids in

surface waters and soils. Surface and

ground waters used for drinking water

will receive treatment (e.g., flocculation

and sedimentation) that will further

reduce the concentration of dissolved

ethoxylated quaternary ammonium

compounds. It has been estimated that

surface waters used for drinking water

supplies would contain no more than

0.35 tkg/L of these compounds (Ref. 5,

Procter and Gamble, 1984b).

2. Evidence for environmental

exposure. No monitoring studies were

found. An assessment by the Office of

Toxic Substances (Ref. 1, Battin, 1988b)

estimated receiving stream

concentrations of 0.03 to 0.25 ug/L at

manufacturing sites and 0.02 to 18.5 ug/L

near use sites, depending upon location

and stream flows. Procter and Gamble

(Ref. 5, 1984b) estimated that consumer

uses of EEQ would yield raw

wastewater concentrations of about 280

ug/L. Most (95 percent or more) will be

sorbed by sludge solids during

wastewater treatment and the

concentration of EEQ in treatment plant

effluents was estimated at 35 ug/L.

II. Chemical Fate Information

A. Transport

The physical and chemical properties

of the ethoxylated quaternary

ammonium compounds indicate that

they will partition strongly to sludge

solids and organic sediments. The

estimated low vapor pressure and

moderate solubility in water rule out

volatilization as an important factor.

The cationic nature of these compounds

will contribute to their sorption to

sludge and sediment solids which

generally are negatively charged.

B. Persistence

. No published information was found

on the persistence of the ethoxylated -

quaternary ammonium fabric softeners.

A summary report of unpublished

information (Ref. 5, Procter and Gamble,

1984b) showed 24 to 34 percent

biodegradation after 138 days,, using

EEQ at 10 and 100 ug/L in river water

and following carbon dioxide evolution.

BOD studies using PEQ reported by

Sherex (Ref. 7, 1984) showed 18 percent

of theoretical oxygen uptake after 5

days and 31 percent after 30 days. While

this indicates that EEQ and PEQ are

biodegradable under aerobic conditions

in river water, it also indicates that

aerobic biodegradation will be relatively

slow. The Procter and Gamble report

(Ref. 5, 1984b) noted that the river water

biodegradation studies were conducted

with and without sediment but did not

provide details. These quaternary

ammonium compounds are expected to

partition to sediments following release

to the environment and their persistence

in sediments, under both aerobic and

anaerobic conditions, is unknown. Also

unknown is the persistence of these

compounds under conditions found in

estuaries and the ocean. Persistence in

saline water may be different than in

fresh water. Nitrilotriacetic acid, for

example, was found to be resistant to

biodegradation in estuarine waters (Ref.

.3, Bourquin and Przybyszewski, 1977)

"although it is readily biodegraded by

acclimated. microorganisms in fresh

water.

C. Rationale for Chemical Fate

Recommendations

EEQ, PEQ and PEQ analogs are likely

to sorb strongly to waste treatment

sludges and, receiving stream organic

sediments and may persist for relatively

long time periods following sorption.

Since they are being continuously

released, to both fresh water and

estuarine receiving waters and may

persist for relatively long periods of time

there may be a tendency for these

compounds to accumulate in estuarine,

river and lake sediments near discharge

points, with gradually increasing

concentrations. There-is a need to better

define the persistence of these

compounds, under both aerobic and

anaerobic. conditions, when sorbed to

organic sediments typical of both

freshwater and estuarine conditions.

This information is needed in order to

better assess the potential

concentrations of these compounds in

the sediments and the-potential hazard

to benthic organisms.

II. Biological Effects of Concern to

HIuinan Health

A. Met abolism; and Toxicokinetics

No information, was found.

& Acute and Subchronic (Short-term)

Effects

Summary reports on unpublished data

from acute, oral, percutaneous, ocular,

skin irritation and subchronic toxicity

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Federal Register / Vol. 53, No. 98 / Friday, May 20, 1988 / Notices

studies with EEQ were submitted by

Procter and Gamble (Ref. 5, 1984b; Ref.

6, 1988). Data on acute oral, eye

irritation, skin irritation and skin

sensitization studies with PEQ were

submitted by Sherex (Ref. 7, 1984). Data

from acute oral, eye irritation and

primary skin irritation studies with PEQ

were provided by Capital City Products

(Ref. 4, 1987).

The acute oral tests with EEQ and

PEQ were all conducted using rats.

Studies with EEQ yielded a minimum

lethal dose greater than 15 g/kg. Studies

with a 4 percent dispersion of PEQ

showed an LD5o greater than 15.38 g/kg.

Minimal eye irritation was observed

for EEQ jnstifled in the conjunctival sac

of rabbit eyes unrinsed after treatment.

PEQ was rated minimally irritating after

instillation to unrinsed rabbit eyes.

Percutaneous studies with undiluted

EEQ applied occluded to clipped intact

and abraded backs of rabbits at dose

levels of 2 g per kg for 24 hours yielded a

minimum lethal does greater than 1.5 g

per kg (the only dose tested, with a 14-

day post-application period for

mortality.

EEQ was applied occluded or on an

open patch to clipped intact and

abraded rabbit backs for 24 hours. Mild

to moderate skin irritation was observed

for up to 48 hours after patch removal.

PEQ was applied to gauze patches and

* exposed to clipped intact and abraded

rabbit backs for 24 hours. The substance

was rated mildly to severely irritating

following observations at 24 and 72

hours.

A skin sensitization study reported by

Procter and Gamble (Ref. 5, 1984b)

employed 25 percent (w/v) EEQ in 80:20

ethanol: Water solution applied in

occluded patches to the clipped backs of

guinea pigs for six hours, once a week,

during a three-week induction period.

The EEQ treated animals were

challenged with 20 percent (w/v) EEQ in

acetone for a single 6-hour occluded

exposure approximately two weeks

after completion of induction. Five out of

20 induced guinea pigs showed signs of

delayed conta ct hypersensitivity. These

studies led to the conclusion with EEQ

is a mild skin sensitizer in guinea pigs.

Similar studies reported by Sherex (Ref.

7. 1984) concluded that PEQ is not a skin

sensitizer.

In a subchronic toxicity study (Ref. 5,

Procter and Gamble, 1984b) rabbits were

treated topically with 2 mL per kg per

day of EEQ at a dose level of 300 mg of

active compound per kg per day, five

days per week for 4 weeks. Each group

contained five males and five females.

There were no treatment-related

changes in body weights, body weight

gain, organ weights or organ to body

weight ratios. It was also reported that

there were no treatment-related clinical

changes. However, animals receiving

EEQ had significantly greater mean

corpuscular volumes in week 4 than the

controls and there was an increased

incidence of dermal inflammation, of

diffuse distribution and associated with

acanthosis, that was considered

treatment-related. An increased

incidence of dermatitis was attributed to "random variation."

C. Genotoxicity

In summary reports it was stated that

EEQ was tested for mutagenicity in the

Salmonella assay, with and without

metabolic activation, and the mouse

lymphoma assay (Ref. 5, Procter and.

Gamble 1984b) and that those tests

produced negative results. No

information was found for PEQ or the

other ethoxylated quaternary

ammonium compounds recommended in

this Report.

D. Oncogenicity

No information was found.

E. Reproductive and Developmental

Effects

No information was found.

F. Chronic (Long-term) Effects

No information was found.

G. Observations in Humans

Little or no irritation-was observed

with human volunteers in a skin

irritation test with aqueous dispersions

of EEQ using 0.3 mL of EEQ per

occludedpatch (Ref. 5, Procter and

Gamble, 1984b). EEQ was tested in a

single 24-hour and three 24-hour

exposures over a 6-day period at

concentrations up to 20 percent w/v). In

another Procter and Gamble study (Ref.

5, 1984b), 87 volunteers received 9

exposures to 10 percent (w/v] aqueous

EEQ and 205 volunteers received 9

exposures to 25 percent (w/v) aqueous

EEQ (0.3 mL per occluded patch) applied

for a 24-hour period, 3 times a week

during a 3-week induction period. No

skin sensitization was observed when

subjects were challenged two weeks

later with a single 24-hour occluded

patch with the same concentration used

during induction.

H. Rationale for Health Effects

Recommendations

It has been estimated that fabric

softeners that are applied to fabrics

during the washing process are widely

used in the U.S. Annual U.S.

consumption of the ethoxylated

quaternary ammonium type fabric

softeners has been estimated at about 25

million pounds. It is quite apparent that

a significant portion of the population is

exposed, on a nearly continuous basis,

to these chemicals in clothing, toweling

and bed linens. Exposure will be

primarily dermal although there may be

very low concentrations in some

drinking water supplies. Dermal

exposure tests reported to date have

involved only acute or short-term

exposures. EEQ was described as a mild

to severe irritant and PEQ was mildly

irritating when applied to rabbit skin.

EEQ was a mild skin sensitizer in some

guinea pig studies.

Although exposure concentrations

used in short-term studies were reported

to be several-fold higher than estimated

human exposures from softened fabrics,

information from these short-term,

intermittent-exposure tests is not useful

in predicting what effects might occur

with long-term (years) continuous

exposure. It is therefore recommended

that EEQ, PEQ and commercially

important analogs of PEQ be tested for

chronic toxicity to evaluate potential

effects resulting from long-term dermal

exposure.

IV. Ecological Effects of Concern

A. Acute and Subchronic (Short-term)

Effects

Summary data submitted by Procter

and Gamble (Ref. 5, 1984b) show EEQ

toxicity to bluegills, sheepshead

minnows, mysid shrimp and Daphnia

magna water fleas, with LC5, values

ranging from 0.3 to 45 mg/L. The

presence of an anionic surfactant or the

use of natural surface waters with

sediments mitigated the effects on

bluegills and daphnia. No data were

found for benthic organisms and this is a

data gap of concern since these

compounds are likely to partition to

sediments following release to the

environment. No data were found for

PEQ or its analogs.

B. Chronic (Long-term) Effects

No information was found.

C. Other Ecological Effects (Biological,

Behavioral or Ecosystem Processes)

EEQ was reported to inhibit algal

growth at moderately low

concentrations (Ref. 5, Procter and

Gamble, 1984b). The algistatic

concentrations were 1.33 mg/L for a

Selenastrum sp., 0.52 mg/L for a

Mycrocystis sp., and 9.4 mg/L for a

Dunaliela sp. No data were found for

PEQ or its'analogs.

18209
Federal Register / Vol. 53, No. 98 / Friday, May 20, 1988 /. Notices.

D. Bioconcentration and Food-chain

Transport

The measured log P of 2.48 for EEQ

indicates a potential for some

bioconcentration. Procter and Gamble

(Ref. 5, 1984b) reported an estimated

bioconcentration factor (BCF) of A5 for

EEQ, based on the log P. No information

was found for PEQ or its analogs.

E. Rationale for Ecological Effects

Recommendations

Environmental fate considerations

indicate that the ethoxylated quaternary

ammonium compounds will sorb

strongly to sludge solids and sediments.

They may persist for relatively long

periods of time under those conditions

and.accumulate in sediments in the

vicinity of wastewater discharges. This

information plus the demonstrated

toxicity of EEQ to fish, aquatic

invertebrates and algae, raise concerns

for benthic organisms. Acute toxicity

should be determined for representative

freshwater and estuarine benthic

organisms andif the ethoxylated

quaternary ammonium compounds are

found to be relatively persistent in the

environment, chronic studies on the

same organisms may be warranted.

References

(1) Battin, A. Memorandum on exposure

and release of ethoxylated quaternary

ammonium compounds in liquid fabric

softeners from Andrew Battin, Exposure

Assessment Branch, Office of Toxic

Substances, U.S. Environmental Protection

Agency, to John D. Walker, Test Rules '

Development Branch. (February 2, 1988b).

(2) Battin, A. Memorandum on physical/

chemical property estimations from Andrew

Battin, Exposure Assessment Branch, Office

of Toxic Substances, U.S. Environmental

Protection Agency, to Robert Brink, TSCA

Interagency Testing Committee (April 8,

1988c).

(3) Bourquin, A.W. and Przybyszewski,

V.A. "Distribution of bacteria and

nitrilotriacetate-degrading potential in an

estuarine environment," Applied and

Environmental Microbiology. 34:411-418

(1977).

(4) Capital City Products. Letter and

unpublished information from John B.

Braunwarth, Operations Manager, Capital

City Products Co. Janesville, WI, to Robert

Brink, TSCA Interagency Testing Committee

(February 18, 1987).

(5) Procter and Gamble. Letter and

unpublished information from T.W. Mooney,

Manager, Technical Government Relations,

The Procter and Gamble Co., Cincinnati, OH,

to Arthur Stern, TSCA Interagency Testing

Committee (September 12, 1984b).

(6) Procter and Gamble. Letter from R.N.

Sturm, Associate Director, Bar Soap and

Household Cleaning Product Development,

Procter and Gamble Co., Cincinnati, OH, to

Robert Brink, TSCA Interagency Testing

'Committee (April 19, 1988).

(7) Sherex. Unpublished information

submitted from Howard M. Hickman, Sherex

Chemical Co., Inc., Dublin, OH, to Martin

Greif, TSCA Interagency Testing Committee

(January 17, 1984).

(8) Sherex. Personal communication from

Howard Hickman of Sherex Chemical Co.,

Inc. Dublin, OH, to L. Borghi, Dynamac

Corporation (January 13, 1987).

[FR Doc. 88-11254 Filed 5-19-88; 8:45 am]

BILLING CODE 6560-50-M

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