JP4982030B2 - ポリアミドおよび水素添加カルボキシル化ニトリルゴムの耐熱性および耐油性ポリマーブレンド - Google Patents
ポリアミドおよび水素添加カルボキシル化ニトリルゴムの耐熱性および耐油性ポリマーブレンド Download PDFInfo
- Publication number
- JP4982030B2 JP4982030B2 JP2003525084A JP2003525084A JP4982030B2 JP 4982030 B2 JP4982030 B2 JP 4982030B2 JP 2003525084 A JP2003525084 A JP 2003525084A JP 2003525084 A JP2003525084 A JP 2003525084A JP 4982030 B2 JP4982030 B2 JP 4982030B2
- Authority
- JP
- Japan
- Prior art keywords
- polyamide
- nitrile rubber
- phr
- carboxylated nitrile
- hydrogenated carboxylated
- Prior art date
- 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 - Lifetime
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- 239000004952 Polyamide Substances 0.000 title claims description 44
- 229920002647 polyamide Polymers 0.000 title claims description 44
- 229920000459 Nitrile rubber Polymers 0.000 title claims description 32
- 229920002959 polymer blend Polymers 0.000 title description 3
- 238000002156 mixing Methods 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 18
- 150000002978 peroxides Chemical class 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 16
- 150000002825 nitriles Chemical class 0.000 claims description 11
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- 150000001993 dienes Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 25
- 229920006170 Therban® Polymers 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 21
- 229920001971 elastomer Polymers 0.000 description 18
- 229920002292 Nylon 6 Polymers 0.000 description 15
- 229920006055 Durethan® Polymers 0.000 description 12
- 239000003963 antioxidant agent Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
- 239000000806 elastomer Substances 0.000 description 10
- -1 shields Substances 0.000 description 10
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 9
- HDIHOAXFFROQHR-UHFFFAOYSA-N 6-aminohexylcarbamic acid Chemical compound NCCCCCCNC(O)=O HDIHOAXFFROQHR-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 8
- 230000003078 antioxidant effect Effects 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000004014 plasticizer Substances 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 239000004971 Cross linker Substances 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 238000011049 filling Methods 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229940105296 zinc peroxide Drugs 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- 229920000571 Nylon 11 Polymers 0.000 description 3
- 229920000299 Nylon 12 Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000010734 process oil Substances 0.000 description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 description 3
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- 229920003346 Levapren® Polymers 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- NFGXHKASABOEEW-GYMWBFJFSA-N (S)-methoprene Chemical compound COC(C)(C)CCC[C@H](C)C\C=C\C(\C)=C\C(=O)OC(C)C NFGXHKASABOEEW-GYMWBFJFSA-N 0.000 description 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
- FCHGUOSEXNGSMK-UHFFFAOYSA-N 1-tert-butylperoxy-2,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(OOC(C)(C)C)=C1C(C)C FCHGUOSEXNGSMK-UHFFFAOYSA-N 0.000 description 1
- XSQHUYDRSDBCHN-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanenitrile Chemical group CC(C)C(C)(C#N)C(C)C XSQHUYDRSDBCHN-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
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- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
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- UDQCDDZBBZNIFA-UHFFFAOYSA-N 4-methyl-1,3-dihydrobenzimidazole-2-thione Chemical compound CC1=CC=CC2=C1NC(=S)N2 UDQCDDZBBZNIFA-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- 229920003189 Nylon 4,6 Polymers 0.000 description 1
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- 239000005062 Polybutadiene Substances 0.000 description 1
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- KRADHMIOFJQKEZ-UHFFFAOYSA-N Tri-2-ethylhexyl trimellitate Chemical compound CCCCC(CC)COC(=O)C1=CC=C(C(=O)OCC(CC)CCCC)C(C(=O)OCC(CC)CCCC)=C1 KRADHMIOFJQKEZ-UHFFFAOYSA-N 0.000 description 1
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- 125000000217 alkyl group Chemical group 0.000 description 1
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- XAUGYNZHGJOSSQ-UHFFFAOYSA-N bis(2-butoxy-2-ethoxyethyl) hexanedioate Chemical compound CCCCOC(OCC)COC(=O)CCCCC(=O)OCC(OCC)OCCCC XAUGYNZHGJOSSQ-UHFFFAOYSA-N 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920006123 polyhexamethylene isophthalamide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000010059 sulfur vulcanization Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012936 vulcanization activator Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L13/00—Compositions of rubbers containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
- C08L15/005—Hydrogenated nitrile rubber
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002356580A CA2356580A1 (en) | 2001-09-05 | 2001-09-05 | Heat and oil resistant polymer blends |
| CA2,356,580 | 2001-09-05 | ||
| PCT/CA2002/001355 WO2003020820A1 (en) | 2001-09-05 | 2002-09-04 | Heat and oil resistant polymer blends of polyamides and hydrogenated carboxylated nitrile rubber |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005501172A JP2005501172A (ja) | 2005-01-13 |
| JP2005501172A5 JP2005501172A5 (enExample) | 2006-01-05 |
| JP4982030B2 true JP4982030B2 (ja) | 2012-07-25 |
Family
ID=4169885
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003525084A Expired - Lifetime JP4982030B2 (ja) | 2001-09-05 | 2002-09-04 | ポリアミドおよび水素添加カルボキシル化ニトリルゴムの耐熱性および耐油性ポリマーブレンド |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20030134979A1 (enExample) |
| EP (1) | EP1427779B1 (enExample) |
| JP (1) | JP4982030B2 (enExample) |
| CN (1) | CN100402594C (enExample) |
| CA (1) | CA2356580A1 (enExample) |
| MX (1) | MXPA04001838A (enExample) |
| TW (1) | TWI240737B (enExample) |
| WO (1) | WO2003020820A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4151456B2 (ja) * | 2003-03-28 | 2008-09-17 | 東海ゴム工業株式会社 | 自動車燃料配管用コネクタ |
| CA2428222A1 (en) * | 2003-05-08 | 2004-11-08 | Bayer Inc. | Rubber compound comprising nitrile rubbers |
| CA2438111A1 (en) * | 2003-08-25 | 2005-02-25 | Bayer Inc. | Nitrile polymer compounds for magntic seal applications |
| JP4156565B2 (ja) * | 2004-06-15 | 2008-09-24 | 横浜ゴム株式会社 | 自動車部品用熱可塑性樹脂組成物 |
| CA2490046A1 (en) * | 2004-12-10 | 2006-06-10 | Lanxess Inc. | Multistage process for the manufacture of peroxide-cured hxnbr-polyamide thermoplastic vulcanizates |
| DE102005002867A1 (de) * | 2005-01-21 | 2006-07-27 | Bayer Materialscience Ag | Uretdionbildung in Lösung |
| ATE395377T1 (de) | 2005-07-14 | 2008-05-15 | Lanxess Deutschland Gmbh | Besser verarbeitbarethermoplastische elastomere auf basis nitrilkautschuk niedriger mooney viskosität |
| DE102005042265A1 (de) * | 2005-09-06 | 2007-03-08 | Lanxess Deutschland Gmbh | Vernetzbare Zusammensetzungen, daraus erhältliche thermoplastische Elastomere und deren Verwendung |
| DE102005062075A1 (de) | 2005-12-22 | 2007-06-28 | Lanxess Deutschland Gmbh | Neue Kautschuk-Thermoplast-Mehrkomponenten-Systeme, daraus herstellte Kautschuk-Thermoplast-Verbund-Formteile, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US20100093943A1 (en) * | 2008-10-14 | 2010-04-15 | Hallstar Innovations Corp. | Reactive esters as plasticizers for elastomers |
| WO2012002356A1 (ja) * | 2010-06-29 | 2012-01-05 | 日本ゼオン株式会社 | ニトリル共重合体ゴム組成物 |
| ES2561718T3 (es) | 2011-03-31 | 2016-02-29 | Zeon Corporation | Composición de caucho de nitrilo muy saturado y caucho reticulado |
| EP2757127A1 (de) * | 2013-01-21 | 2014-07-23 | LANXESS Deutschland GmbH | Vernetzung von carboxylierten Nitrilkautschuken mit resolhaltigen Vernetzungssystemen |
| US20160090464A1 (en) * | 2013-04-26 | 2016-03-31 | Zeon Corporation | Nitrile rubber composition, cross-linkable rubber composition, and cross-linked rubber |
| JP6898097B2 (ja) * | 2013-11-08 | 2021-07-07 | アーケマ・インコーポレイテッド | ポリアミドの変性 |
| EP2987828A1 (en) * | 2014-08-22 | 2016-02-24 | Lanxess Inc. | Butyl ionomer blends |
| JP6614153B2 (ja) | 2014-09-05 | 2019-12-04 | 日本ゼオン株式会社 | 高飽和ニトリルゴム組成物およびゴム架橋物 |
| EP3239231B1 (en) * | 2014-12-25 | 2020-09-09 | Zeon Corporation | Method for manufacturing a cross-linkable nitrile rubber composition and cross-linked rubber product |
| CN104610736B (zh) * | 2015-02-03 | 2017-03-15 | 上海日之升新技术发展有限公司 | 高透明度、抗低温开裂尼龙复合材料及其制备方法 |
| CN111492002A (zh) * | 2017-12-21 | 2020-08-04 | 阿朗新科德国有限责任公司 | 具有改进的热空气耐受性的固化hnbr产品 |
| CN110684252B (zh) * | 2018-07-06 | 2022-01-04 | 中国石油天然气股份有限公司 | 一种羧基丁腈橡胶及其制备方法 |
| CN113773565A (zh) * | 2021-09-15 | 2021-12-10 | 中国热带农业科学院农产品加工研究所 | 一种无硫硫化羧基丁腈胶乳及其硫化方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4508867A (en) | 1983-11-07 | 1985-04-02 | Polysar Limited | Polymer compositions comprising polyamides, carboxylated (meth)acrylonitrile-butadiene rubber, and nonpolymeric additives |
| US4937290A (en) * | 1988-09-26 | 1990-06-26 | The Goodyear Tire & Rubber Company | Nylon modified rubber composition wherein either nylon or rubber or both are reacted with a thio acid |
| CA1339789C (en) * | 1988-10-13 | 1998-03-31 | Heinz Peter Paul Plaumann | Vulcanizable rubbery compositions |
| TW284778B (enExample) * | 1992-03-02 | 1996-09-01 | Dsm Nv |
-
2001
- 2001-09-05 CA CA002356580A patent/CA2356580A1/en not_active Abandoned
-
2002
- 2002-08-14 TW TW091118232A patent/TWI240737B/zh not_active IP Right Cessation
- 2002-09-04 US US10/234,684 patent/US20030134979A1/en not_active Abandoned
- 2002-09-04 EP EP02759973A patent/EP1427779B1/en not_active Expired - Lifetime
- 2002-09-04 MX MXPA04001838A patent/MXPA04001838A/es active IP Right Grant
- 2002-09-04 JP JP2003525084A patent/JP4982030B2/ja not_active Expired - Lifetime
- 2002-09-04 WO PCT/CA2002/001355 patent/WO2003020820A1/en not_active Ceased
- 2002-09-04 CN CNB028174399A patent/CN100402594C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1427779A1 (en) | 2004-06-16 |
| TWI240737B (en) | 2005-10-01 |
| CA2356580A1 (en) | 2003-03-05 |
| JP2005501172A (ja) | 2005-01-13 |
| EP1427779B1 (en) | 2012-02-22 |
| CN100402594C (zh) | 2008-07-16 |
| US20030134979A1 (en) | 2003-07-17 |
| MXPA04001838A (es) | 2004-07-08 |
| WO2003020820A1 (en) | 2003-03-13 |
| CN1551901A (zh) | 2004-12-01 |
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