NL9300336A

NL9300336A - Carbonzuuresters van hydroxyfenylalkanolen als stabiliseermiddelen.

Carbonzuuresters van hydroxyfenylalkanolen als stabiliseermiddelen. Download PDF

Info

Publication number: NL9300336A
Authority: NL; Netherlands
Prior art keywords: formula; alkyl; butyl; tert; substituted
Prior art date: 1992-02-24

Application number

NL9300336A

Other languages

English (en)

Dutch (nl)

Original Assignee

Ciba Geigy

Priority date

1992-02-24

Filing date

1993-02-23

Publication date

1993-09-16

1993-02-23 Application filed by Ciba Geigy filed Critical Ciba Geigy

1993-09-16 Publication of NL9300336A publication Critical patent/NL9300336A/nl

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-1 HYDROXYPHENYL Chemical class 0.000 title claims description 161
239000003381 stabilizer Substances 0.000 title description 23
150000004651 carbonic acid esters Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 140
125000000217 alkyl group Chemical group 0.000 claims description 68
239000000203 mixture Substances 0.000 claims description 65
125000000753 cycloalkyl group Chemical group 0.000 claims description 40
229920001577 copolymer Polymers 0.000 claims description 34
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 30
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 30
229920000642 polymer Polymers 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 27
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 22
229910052757 nitrogen Inorganic materials 0.000 claims description 20
125000002947 alkylene group Chemical group 0.000 claims description 19
239000011368 organic material Substances 0.000 claims description 17
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
230000015556 catabolic process Effects 0.000 claims description 12
238000006731 degradation reaction Methods 0.000 claims description 12
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
230000001590 oxidative effect Effects 0.000 claims description 12
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 10
125000002993 cycloalkylene group Chemical group 0.000 claims description 10
239000000463 material Substances 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 8
230000000087 stabilizing effect Effects 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 7
229920000098 polyolefin Polymers 0.000 claims description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
150000001336 alkenes Chemical class 0.000 claims description 6
235000010290 biphenyl Nutrition 0.000 claims description 6
239000004305 biphenyl Substances 0.000 claims description 6
125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
125000005724 cycloalkenylene group Chemical group 0.000 claims description 6
229920005613 synthetic organic polymer Polymers 0.000 claims description 6
150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000004957 naphthylene group Chemical group 0.000 claims description 5
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 5
125000003884 phenylalkyl group Chemical group 0.000 claims description 5
125000005591 trimellitate group Chemical group 0.000 claims description 5
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 4
125000001326 naphthylalkyl group Chemical group 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000003963 antioxidant agent Substances 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
150000001925 cycloalkenes Chemical class 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
229930192474 thiophene Natural products 0.000 claims description 3
LJRWNCBKRLYXHQ-UHFFFAOYSA-N 6-(3-tert-butyl-4-hydroxy-5-methylphenyl)hexyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCC1=CC(C)=C(O)C(C(C)(C)C)=C1 LJRWNCBKRLYXHQ-UHFFFAOYSA-N 0.000 claims description 2
GYTKHIWTONFGKP-UHFFFAOYSA-N bis[6-(3,5-ditert-butyl-4-hydroxyphenyl)hexyl] benzene-1,3-dicarboxylate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCCCCCOC(=O)C=2C=C(C=CC=2)C(=O)OCCCCCCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 GYTKHIWTONFGKP-UHFFFAOYSA-N 0.000 claims description 2
SMBCSJBYDSGLKV-UHFFFAOYSA-N bis[6-(3-tert-butyl-4-hydroxy-5-methylphenyl)hexyl] benzene-1,3-dicarboxylate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCCCCCOC(=O)C=2C=C(C=CC=2)C(=O)OCCCCCCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 SMBCSJBYDSGLKV-UHFFFAOYSA-N 0.000 claims description 2
AKXAPAAVMGIZCU-UHFFFAOYSA-N bis[6-(3-tert-butyl-4-hydroxy-5-methylphenyl)hexyl] butanedioate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCCCCCOC(=O)CCC(=O)OCCCCCCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 AKXAPAAVMGIZCU-UHFFFAOYSA-N 0.000 claims description 2
SCKDFDJDXKPXTN-UHFFFAOYSA-N bis[6-(3-tert-butyl-4-hydroxy-5-methylphenyl)hexyl] hexanedioate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCCCCCOC(=O)CCCCC(=O)OCCCCCCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 SCKDFDJDXKPXTN-UHFFFAOYSA-N 0.000 claims description 2
239000005416 organic matter Substances 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
DJJPODJJYQUWEP-UHFFFAOYSA-N bis[6-(3-tert-butyl-4-hydroxy-5-methylphenyl)hexyl] octanedioate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCCCCCOC(=O)CCCCCCC(=O)OCCCCCCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 DJJPODJJYQUWEP-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 29
239000003508 Dilauryl thiodipropionate Substances 0.000 description 29
235000019304 dilauryl thiodipropionate Nutrition 0.000 description 29
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
239000002656 Distearyl thiodipropionate Substances 0.000 description 26
235000019305 distearyl thiodipropionate Nutrition 0.000 description 26
238000004458 analytical method Methods 0.000 description 25
PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000047 product Substances 0.000 description 20
150000002148 esters Chemical class 0.000 description 18
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
238000004566 IR spectroscopy Methods 0.000 description 16
239000002253 acid Substances 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
239000004743 Polypropylene Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
238000004821 distillation Methods 0.000 description 11
239000004952 Polyamide Substances 0.000 description 10
229920002647 polyamide Polymers 0.000 description 10
229920002857 polybutadiene Polymers 0.000 description 10
239000000243 solution Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000005062 Polybutadiene Substances 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
229920001684 low density polyethylene Polymers 0.000 description 9
239000004702 low-density polyethylene Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000003921 oil Substances 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
239000012043 crude product Substances 0.000 description 7
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 7
239000002184 metal Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
229920006324 polyoxymethylene Polymers 0.000 description 7
229920001155 polypropylene Polymers 0.000 description 7
229920003048 styrene butadiene rubber Polymers 0.000 description 7
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 6
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
239000000654 additive Substances 0.000 description 6
230000032683 aging Effects 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
238000001035 drying Methods 0.000 description 6
HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 6
229920000126 latex Polymers 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000004417 polycarbonate Substances 0.000 description 6
229920000915 polyvinyl chloride Polymers 0.000 description 6
239000004800 polyvinyl chloride Substances 0.000 description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
239000002904 solvent Substances 0.000 description 6
RNOAMAIYLHZSOP-UHFFFAOYSA-N 2-tert-butyl-4-(4-hydroxybutyl)-6-methylphenol Chemical compound CC1=CC(CCCCO)=CC(C(C)(C)C)=C1O RNOAMAIYLHZSOP-UHFFFAOYSA-N 0.000 description 5
229920002943 EPDM rubber Polymers 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229920000877 Melamine resin Polymers 0.000 description 5
239000004698 Polyethylene Substances 0.000 description 5
239000002174 Styrene-butadiene Substances 0.000 description 5
150000001252 acrylic acid derivatives Chemical class 0.000 description 5
238000012512 characterization method Methods 0.000 description 5
229910052681 coesite Inorganic materials 0.000 description 5
239000007859 condensation product Substances 0.000 description 5
229910052906 cristobalite Inorganic materials 0.000 description 5
JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 5
150000001993 dienes Chemical class 0.000 description 5
229920001903 high density polyethylene Polymers 0.000 description 5
239000004700 high-density polyethylene Substances 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
229920000728 polyester Polymers 0.000 description 5
229920000573 polyethylene Polymers 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
239000007858 starting material Substances 0.000 description 5
229910052682 stishovite Inorganic materials 0.000 description 5
150000005846 sugar alcohols Polymers 0.000 description 5
238000012360 testing method Methods 0.000 description 5
229910052905 tridymite Inorganic materials 0.000 description 5
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000004721 Polyphenylene oxide Substances 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
150000001733 carboxylic acid esters Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
229920001971 elastomer Polymers 0.000 description 4
239000004816 latex Substances 0.000 description 4
239000000178 monomer Substances 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
150000002815 nickel Chemical class 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
229920000570 polyether Polymers 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
239000004814 polyurethane Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
235000013772 propylene glycol Nutrition 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000006641 stabilisation Effects 0.000 description 4
238000011105 stabilization Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
238000005809 transesterification reaction Methods 0.000 description 4
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 3
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229920002396 Polyurea Polymers 0.000 description 3
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
229920000800 acrylic rubber Polymers 0.000 description 3
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125000003118 aryl group Chemical group 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
239000000806 elastomer Substances 0.000 description 3
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238000005886 esterification reaction Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
238000010348 incorporation Methods 0.000 description 3
239000003446 ligand Substances 0.000 description 3
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
150000005673 monoalkenes Chemical class 0.000 description 3
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229920001707 polybutylene terephthalate Polymers 0.000 description 3
229920000647 polyepoxide Polymers 0.000 description 3
229920006380 polyphenylene oxide Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000006277 sulfonation reaction Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
229920001169 thermoplastic Polymers 0.000 description 3
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 3
229920002554 vinyl polymer Polymers 0.000 description 3
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125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
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