DE60223680T2 - Verfahren zur pfropfung von ethylenisch ungesättigten carbonsäurederivaten auf thermoplastischen polymeren mit hydroxylaminestern - Google Patents

Info

Publication number

DE60223680T2

DE60223680T2 DE60223680T DE60223680T DE60223680T2 DE 60223680 T2 DE60223680 T2 DE 60223680T2 DE 60223680 T DE60223680 T DE 60223680T DE 60223680 T DE60223680 T DE 60223680T DE 60223680 T2 DE60223680 T2 DE 60223680T2

Authority

DE

Germany

Prior art keywords

acid

alkyl

bis

carboxylic acid

tert

Prior art date

2001-05-15

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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• 238000000034 method Methods 0.000 title claims description 35
• 229920001169 thermoplastic Polymers 0.000 title claims description 28
• 150000002443 hydroxylamines Chemical class 0.000 title description 11
• -1 hydroxylamine ester Chemical class 0.000 claims description 153
• 229920000642 polymer Polymers 0.000 claims description 51
• 125000000217 alkyl group Chemical group 0.000 claims description 49
• 125000003118 aryl group Chemical group 0.000 claims description 46
• 125000004432 carbon atom Chemical group C* 0.000 claims description 46
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 239000000203 mixture Substances 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 33
• 125000001931 aliphatic group Chemical group 0.000 claims description 31
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 30
• 239000002253 acid Substances 0.000 claims description 30
• 150000002431 hydrogen Chemical group 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 150000001875 compounds Chemical class 0.000 claims description 21
• FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000002947 alkylene group Chemical group 0.000 claims description 15
• 150000002148 esters Chemical class 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 150000001991 dicarboxylic acids Chemical class 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 229920002857 polybutadiene Polymers 0.000 claims description 11
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 10
• 239000005062 Polybutadiene Substances 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 10
• 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 229920002943 EPDM rubber Polymers 0.000 claims description 9
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 229910052698 phosphorus Inorganic materials 0.000 claims description 9
• 239000011574 phosphorus Substances 0.000 claims description 9
• 238000012545 processing Methods 0.000 claims description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
• 125000001589 carboacyl group Chemical group 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 7
• 150000007513 acids Chemical class 0.000 claims description 7
• 150000001408 amides Chemical class 0.000 claims description 7
• ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims description 7
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 7
• 229920000098 polyolefin Polymers 0.000 claims description 7
• OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 claims description 7
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 6
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 6
• 125000005442 diisocyanate group Chemical group 0.000 claims description 6
• 238000002844 melting Methods 0.000 claims description 6
• 230000008018 melting Effects 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
• 150000003672 ureas Chemical group 0.000 claims description 6
• 125000006839 xylylene group Chemical group 0.000 claims description 6
• 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 5
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
• 229920000578 graft copolymer Polymers 0.000 claims description 5
• 239000003381 stabilizer Substances 0.000 claims description 5
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 5
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
• JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
• 229920000181 Ethylene propylene rubber Polymers 0.000 claims description 4
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
• 239000005642 Oleic acid Substances 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
• LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
• LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 4
• 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 4
• OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 claims description 3
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 3
• 229940091181 aconitic acid Drugs 0.000 claims description 3
• DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 3
• 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 3
• 150000008064 anhydrides Chemical class 0.000 claims description 3
• PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 claims description 3
• 150000001735 carboxylic acids Chemical class 0.000 claims description 3
• GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 claims description 3
• 150000005690 diesters Chemical class 0.000 claims description 3
• 239000001530 fumaric acid Substances 0.000 claims description 3
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 3
• 239000003999 initiator Substances 0.000 claims description 3
• KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 3
• 229960004488 linolenic acid Drugs 0.000 claims description 3
• 239000011976 maleic acid Substances 0.000 claims description 3
• 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 3
• 229920001195 polyisoprene Polymers 0.000 claims description 3
• GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
• LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 claims description 2
• 239000002530 phenolic antioxidant Substances 0.000 claims description 2
• OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
• 125000003386 piperidinyl group Chemical group 0.000 claims description 2
• 229920002959 polymer blend Polymers 0.000 claims description 2
• 238000010094 polymer processing Methods 0.000 claims description 2
• 229920006132 styrene block copolymer Polymers 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 3
• 150000002763 monocarboxylic acids Chemical class 0.000 claims 2
• 229920001577 copolymer Polymers 0.000 description 41
• 150000003254 radicals Chemical class 0.000 description 34
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 31
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 27
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 22
• 239000004743 Polypropylene Substances 0.000 description 19
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
• 239000000178 monomer Substances 0.000 description 15
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• 150000002513 isocyanates Chemical class 0.000 description 13
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• 150000002009 diols Chemical class 0.000 description 6
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