JPS6229461B2 - - Google Patents

Info

Publication number

JPS6229461B2

JPS6229461B2 JP5048680A JP5048680A JPS6229461B2 JP S6229461 B2 JPS6229461 B2 JP S6229461B2 JP 5048680 A JP5048680 A JP 5048680A JP 5048680 A JP5048680 A JP 5048680A JP S6229461 B2 JPS6229461 B2 JP S6229461B2

Authority

JP

Japan

Prior art keywords

group

aminophenoxy

bis

phenyl

formula

Prior art date

1980-04-18

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

Links

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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
• -1 oxydiphenylene group Chemical group 0.000 claims description 28
• 229920002614 Polyether block amide Polymers 0.000 claims description 27
• 239000011342 resin composition Substances 0.000 claims description 14
• 239000004952 Polyamide Substances 0.000 claims description 12
• 229920002647 polyamide Polymers 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
• 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 5
• 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 4
• 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 4
• 125000004957 naphthylene group Chemical group 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 239000000460 chlorine Substances 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 229910052757 nitrogen Inorganic materials 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 32
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 30
• 125000003118 aryl group Chemical group 0.000 description 23
• OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 16
• 239000001294 propane Substances 0.000 description 16
• 230000015572 biosynthetic process Effects 0.000 description 9
• 239000000203 mixture Substances 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• 238000000034 method Methods 0.000 description 8
• 239000002253 acid Substances 0.000 description 7
• 150000004985 diamines Chemical class 0.000 description 7
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 5
• 238000001746 injection moulding Methods 0.000 description 5
• 239000008188 pellet Substances 0.000 description 5
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
• 238000002156 mixing Methods 0.000 description 4
• HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 238000005452 bending Methods 0.000 description 3
• 239000000843 powder Substances 0.000 description 3
• 239000002994 raw material Substances 0.000 description 3
• YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
• KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 2
• 238000005299 abrasion Methods 0.000 description 2
• KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
• QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 238000000465 moulding Methods 0.000 description 2
• 238000006068 polycondensation reaction Methods 0.000 description 2
• 239000000243 solution Substances 0.000 description 2
• RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
• JCUZDQXWVYNXHD-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diamine Chemical compound NCCC(C)CC(C)(C)CN JCUZDQXWVYNXHD-UHFFFAOYSA-N 0.000 description 1
• DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
• UOFDVLCOMURSTA-UHFFFAOYSA-N 2-(2-carboxyphenoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1C(O)=O UOFDVLCOMURSTA-UHFFFAOYSA-N 0.000 description 1
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
• HSSYVKMJJLDTKZ-UHFFFAOYSA-N 3-phenylphthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1C(O)=O HSSYVKMJJLDTKZ-UHFFFAOYSA-N 0.000 description 1
• JQSRUJUKMCULGS-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)-3,5-dibromophenyl]propyl]-2,6-dibromophenoxy]aniline Chemical compound C=1C(Br)=C(OC=2C=CC(N)=CC=2)C(Br)=CC=1C(CC)C(C=C1Br)=CC(Br)=C1OC1=CC=C(N)C=C1 JQSRUJUKMCULGS-UHFFFAOYSA-N 0.000 description 1
• CKXLOUZITCMXEJ-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)-3,5-dimethylphenyl]propyl]-2,6-dimethylphenoxy]aniline Chemical compound C=1C(C)=C(OC=2C=CC(N)=CC=2)C(C)=CC=1C(CC)C(C=C1C)=CC(C)=C1OC1=CC=C(N)C=C1 CKXLOUZITCMXEJ-UHFFFAOYSA-N 0.000 description 1
• DDUOTTYELMRWJE-UHFFFAOYSA-N 4-[4-[1-[4-(4-aminophenoxy)phenyl]propyl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(CC)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 DDUOTTYELMRWJE-UHFFFAOYSA-N 0.000 description 1
• BZIWJKPYZLPVIN-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dibromophenyl]-1,1,1,3,3,3-hexachloropropan-2-yl]-2,6-dibromophenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=C(Br)C=C(C(C=2C=C(Br)C(OC=3C=CC(N)=CC=3)=C(Br)C=2)(C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)C=C1Br BZIWJKPYZLPVIN-UHFFFAOYSA-N 0.000 description 1
• DHIKMHDCNWDZSS-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dibromophenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]-2,6-dibromophenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=C(Br)C=C(C(C=2C=C(Br)C(OC=3C=CC(N)=CC=3)=C(Br)C=2)(C(F)(F)F)C(F)(F)F)C=C1Br DHIKMHDCNWDZSS-UHFFFAOYSA-N 0.000 description 1
• MUDNCBUJHBRRME-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dibromophenyl]butan-2-yl]-2,6-dibromophenoxy]aniline Chemical compound C=1C(Br)=C(OC=2C=CC(N)=CC=2)C(Br)=CC=1C(C)(CC)C(C=C1Br)=CC(Br)=C1OC1=CC=C(N)C=C1 MUDNCBUJHBRRME-UHFFFAOYSA-N 0.000 description 1
• LRCIDTOMCOTLFJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dichlorophenyl]propan-2-yl]-2,6-dichlorophenoxy]aniline Chemical compound C=1C(Cl)=C(OC=2C=CC(N)=CC=2)C(Cl)=CC=1C(C)(C)C(C=C1Cl)=CC(Cl)=C1OC1=CC=C(N)C=C1 LRCIDTOMCOTLFJ-UHFFFAOYSA-N 0.000 description 1
• ABCHJRPSNNTRGG-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dimethylphenyl]-1,1,1,3,3,3-hexachloropropan-2-yl]-2,6-dimethylphenoxy]aniline Chemical compound CC1=CC(C(C=2C=C(C)C(OC=3C=CC(N)=CC=3)=C(C)C=2)(C(Cl)(Cl)Cl)C(Cl)(Cl)Cl)=CC(C)=C1OC1=CC=C(N)C=C1 ABCHJRPSNNTRGG-UHFFFAOYSA-N 0.000 description 1
• VCFYKCXKADGLPS-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dimethylphenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]-2,6-dimethylphenoxy]aniline Chemical compound CC1=CC(C(C=2C=C(C)C(OC=3C=CC(N)=CC=3)=C(C)C=2)(C(F)(F)F)C(F)(F)F)=CC(C)=C1OC1=CC=C(N)C=C1 VCFYKCXKADGLPS-UHFFFAOYSA-N 0.000 description 1
• UCGUBZDRPKFHQJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3,5-dimethylphenyl]butan-2-yl]-2,6-dimethylphenoxy]aniline Chemical compound C=1C(C)=C(OC=2C=CC(N)=CC=2)C(C)=CC=1C(C)(CC)C(C=C1C)=CC(C)=C1OC1=CC=C(N)C=C1 UCGUBZDRPKFHQJ-UHFFFAOYSA-N 0.000 description 1
• BVDPIHNAIJHQJK-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)-3-methylphenyl]butan-2-yl]-2-methylphenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C(C)=CC=1C(C)(CC)C(C=C1C)=CC=C1OC1=CC=C(N)C=C1 BVDPIHNAIJHQJK-UHFFFAOYSA-N 0.000 description 1
• UXBSLADVESNJEO-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]butan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(CC)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 UXBSLADVESNJEO-UHFFFAOYSA-N 0.000 description 1
• BGKBJXVVPZPBPS-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)-3,5-dibromophenyl]pentan-3-yl]-2,6-dibromophenoxy]aniline Chemical compound C=1C(Br)=C(OC=2C=CC(N)=CC=2)C(Br)=CC=1C(CC)(CC)C(C=C1Br)=CC(Br)=C1OC1=CC=C(N)C=C1 BGKBJXVVPZPBPS-UHFFFAOYSA-N 0.000 description 1
• ZPBCBNPCENPLRR-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)-3,5-dimethylphenyl]pentan-3-yl]-2,6-dimethylphenoxy]aniline Chemical compound C=1C(C)=C(OC=2C=CC(N)=CC=2)C(C)=CC=1C(CC)(CC)C(C=C1C)=CC(C)=C1OC1=CC=C(N)C=C1 ZPBCBNPCENPLRR-UHFFFAOYSA-N 0.000 description 1
• OYGQSMMPUFNMOL-UHFFFAOYSA-N 4-[4-[3-[4-(4-aminophenoxy)phenyl]pentan-3-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(CC)(CC)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 OYGQSMMPUFNMOL-UHFFFAOYSA-N 0.000 description 1
• NAUSGUYYKKTJTC-UHFFFAOYSA-N 4-[4-[[4-(4-aminophenoxy)-3,5-dimethylphenyl]methyl]-2,6-dimethylphenoxy]aniline Chemical compound C=1C(C)=C(OC=2C=CC(N)=CC=2)C(C)=CC=1CC(C=C1C)=CC(C)=C1OC1=CC=C(N)C=C1 NAUSGUYYKKTJTC-UHFFFAOYSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 230000003078 antioxidant effect Effects 0.000 description 1
• 150000007860 aryl ester derivatives Chemical class 0.000 description 1
• FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 230000007423 decrease Effects 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 229920006351 engineering plastic Polymers 0.000 description 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
• 238000001125 extrusion Methods 0.000 description 1
• 239000003063 flame retardant Substances 0.000 description 1
• 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
• 230000001771 impaired effect Effects 0.000 description 1
• 239000003112 inhibitor Substances 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 239000007788 liquid Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 238000010137 moulding (plastic) Methods 0.000 description 1
• KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 239000000049 pigment Substances 0.000 description 1
• 239000004014 plasticizer Substances 0.000 description 1
• 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
• 229920006122 polyamide resin Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 238000006116 polymerization reaction Methods 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
• 238000005979 thermal decomposition reaction Methods 0.000 description 1
• 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1