CA2194652C - Melanges de polyacrylates et de caoutchouc nitrile partiellement hydrogene durcis au peroxyde - Google Patents

Melanges de polyacrylates et de caoutchouc nitrile partiellement hydrogene durcis au peroxyde Download PDF

Info

Publication number: CA2194652C
Authority: CA; Canada
Prior art keywords: mole; peroxide; structural unit; weight; parts
Prior art date: 1996-01-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA 2194652

Other languages

English (en)

Other versions

CA2194652A1 (fr

Inventor

Paul E. Manley

Richard J. Flecksteiner

Michael E. Wood

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Zeon Chemical LP

Original Assignee

Zeon Chemical LP

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-01-18

Filing date

1997-01-08

Publication date

2005-08-02

1997-01-08 Application filed by Zeon Chemical LP filed Critical Zeon Chemical LP

1997-07-19 Publication of CA2194652A1 publication Critical patent/CA2194652A1/fr

2005-08-02 Application granted granted Critical

2005-08-02 Publication of CA2194652C publication Critical patent/CA2194652C/fr

2017-01-08 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 51
229920000058 polyacrylate Polymers 0.000 title claims abstract description 32
229920000459 Nitrile rubber Polymers 0.000 title claims description 22
229920001971 elastomer Polymers 0.000 claims abstract description 27
239000000806 elastomer Substances 0.000 claims abstract description 21
239000005060 rubber Substances 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 12
150000002978 peroxides Chemical class 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 7
-1 methoxyethyl Chemical group 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 3
KQDDPKLNKUOCEX-UHFFFAOYSA-N benzene-1,3-diamine;pyrrole-2,5-dione Chemical compound O=C1NC(=O)C=C1.O=C1NC(=O)C=C1.NC1=CC=CC(N)=C1 KQDDPKLNKUOCEX-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
150000002826 nitrites Chemical class 0.000 claims description 2
150000001451 organic peroxides Chemical class 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
ZFFKAJUXIJDLMC-UHFFFAOYSA-N 5-tert-butylperoxy-1,1,2-trimethylcyclohexane Chemical compound CC1CCC(OOC(C)(C)C)CC1(C)C ZFFKAJUXIJDLMC-UHFFFAOYSA-N 0.000 claims 1
230000015556 catabolic process Effects 0.000 abstract description 2
238000006731 degradation reaction Methods 0.000 abstract description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
238000012360 testing method Methods 0.000 description 7
230000032683 aging Effects 0.000 description 5
239000003921 oil Substances 0.000 description 5
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
230000006835 compression Effects 0.000 description 4
238000000034 method Methods 0.000 description 4
238000012545 processing Methods 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
125000005250 alkyl acrylate group Chemical group 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
230000003078 antioxidant effect Effects 0.000 description 3
238000007906 compression Methods 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
241001441571 Hiodontidae Species 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
239000006229 carbon black Substances 0.000 description 2
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000007720 emulsion polymerization reaction Methods 0.000 description 2
239000000178 monomer Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
230000035882 stress Effects 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
238000010557 suspension polymerization reaction Methods 0.000 description 2
238000010998 test method Methods 0.000 description 2
NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000004594 Masterbatch (MB) Substances 0.000 description 1
101100314372 Onchocerca volvulus tmy-1 gene Proteins 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
125000005396 acrylic acid ester group Chemical group 0.000 description 1
229920000800 acrylic rubber Polymers 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000012662 bulk polymerization Methods 0.000 description 1
125000006226 butoxyethyl group Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000000748 compression moulding Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
230000000593 degrading effect Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
125000003700 epoxy group Chemical group 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
101150041966 lev-11 gene Proteins 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
ONCZDRURRATYFI-QTCHDTBASA-N methyl (2z)-2-methoxyimino-2-[2-[[(e)-1-[3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]acetate Chemical compound CO\N=C(/C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-QTCHDTBASA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
238000011417 postcuring Methods 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
238000001721 transfer moulding Methods 0.000 description 1
238000004073 vulcanization Methods 0.000 description 1

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Compositions Of Macromolecular Compounds (AREA)
Sealing Material Composition (AREA)

CA 2194652 1996-01-18 1997-01-08 Melanges de polyacrylates et de caoutchouc nitrile partiellement hydrogene durcis au peroxyde Expired - Fee Related CA2194652C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US50751696A	1996-01-18	1996-01-18
US08/588,516		1996-01-18

Publications (2)

Publication Number	Publication Date
CA2194652A1 CA2194652A1 (fr)	1997-07-19
CA2194652C true CA2194652C (fr)	2005-08-02

Family

ID=24018940

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2194652 Expired - Fee Related CA2194652C (fr)	1996-01-18	1997-01-08	Melanges de polyacrylates et de caoutchouc nitrile partiellement hydrogene durcis au peroxyde

Country Status (1)

Country	Link
CA (1)	CA2194652C (fr)

1997
- 1997-01-08 CA CA 2194652 patent/CA2194652C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2194652A1 (fr)	1997-07-19

Legal Events

Date	Code	Title	Description
2001-08-08	EEER	Examination request
2011-01-10	MKLA	Lapsed

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