JPS6154045B2 - - Google Patents
Info
- Publication number
- JPS6154045B2 JPS6154045B2 JP6686279A JP6686279A JPS6154045B2 JP S6154045 B2 JPS6154045 B2 JP S6154045B2 JP 6686279 A JP6686279 A JP 6686279A JP 6686279 A JP6686279 A JP 6686279A JP S6154045 B2 JPS6154045 B2 JP S6154045B2
- Authority
- JP
- Japan
- Prior art keywords
- oxazolone
- group
- benzoxazin
- methyl
- polyamide
- 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
Links
- 239000004952 Polyamide Substances 0.000 claims description 57
- 229920002647 polyamide Polymers 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- -1 oxazolone compound Chemical class 0.000 description 37
- 238000000034 method Methods 0.000 description 22
- 125000003277 amino group Chemical group 0.000 description 15
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- SFDGJDBLYNJMFI-UHFFFAOYSA-N 3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC=NC2=C1 SFDGJDBLYNJMFI-UHFFFAOYSA-N 0.000 description 7
- HTQKMAGYKHPFQM-UHFFFAOYSA-N 4-methyl-4h-1,3-oxazol-5-one Chemical compound CC1N=COC1=O HTQKMAGYKHPFQM-UHFFFAOYSA-N 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 6
- BWLYWJSWRDLSGY-UHFFFAOYSA-N 4,4-dimethyl-1,3-oxazol-5-one Chemical compound CC1(C)N=COC1=O BWLYWJSWRDLSGY-UHFFFAOYSA-N 0.000 description 5
- 239000000980 acid dye Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- DANDTMGGYNCQLG-UHFFFAOYSA-N 4h-1,3-oxazol-5-one Chemical compound O=C1CN=CO1 DANDTMGGYNCQLG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- DGEYLAXCRHMGLG-UHFFFAOYSA-N 4-(2-methylpropyl)-4h-1,3-oxazol-5-one Chemical compound CC(C)CC1N=COC1=O DGEYLAXCRHMGLG-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000006501 nitrophenyl group Chemical group 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical class O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 2
- VNKZACZQXVQWKA-UHFFFAOYSA-N 4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound CC(C)C1N=COC1=O VNKZACZQXVQWKA-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- HTTLBYITFHMYFK-UHFFFAOYSA-N bentranil Chemical compound N=1C2=CC=CC=C2C(=O)OC=1C1=CC=CC=C1 HTTLBYITFHMYFK-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- 238000012691 depolymerization reaction Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229920006017 homo-polyamide Polymers 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- YMVDIDRLTRKWOW-UHFFFAOYSA-N oxazin-6-one Chemical compound O=C1C=CC=NO1 YMVDIDRLTRKWOW-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ARJYLIOEJWMXTA-UHFFFAOYSA-N 2-[(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)methyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1CC1=NC(C)(C)C(=O)O1 ARJYLIOEJWMXTA-UHFFFAOYSA-N 0.000 description 1
- RFLLHIZFIWJOIH-UHFFFAOYSA-N 2-[(4-oxo-3,1-benzoxazin-2-yl)methyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(CC=3OC(=O)C4=CC=CC=C4N=3)=NC2=C1 RFLLHIZFIWJOIH-UHFFFAOYSA-N 0.000 description 1
- MNKGJLCEYRTBNX-UHFFFAOYSA-N 2-[(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)methyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1CC1=NC(C(C)C)C(=O)O1 MNKGJLCEYRTBNX-UHFFFAOYSA-N 0.000 description 1
- WVFQIHLBBWLQGN-UHFFFAOYSA-N 2-[(5-oxo-4h-1,3-oxazol-2-yl)methyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1CC1=NCC(=O)O1 WVFQIHLBBWLQGN-UHFFFAOYSA-N 0.000 description 1
- YEGYPUXZMURDLE-UHFFFAOYSA-N 2-[10-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)decyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1CCCCCCCCCCC1=NC(C)(C)C(=O)O1 YEGYPUXZMURDLE-UHFFFAOYSA-N 0.000 description 1
- DFAWQYROSGGZCU-UHFFFAOYSA-N 2-[10-(5-oxo-4h-1,3-oxazol-2-yl)decyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1CCCCCCCCCCC1=NCC(=O)O1 DFAWQYROSGGZCU-UHFFFAOYSA-N 0.000 description 1
- QRCCSIXJZWWTKH-UHFFFAOYSA-N 2-[2-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)ethyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1CCC1=NC(C)(C)C(=O)O1 QRCCSIXJZWWTKH-UHFFFAOYSA-N 0.000 description 1
- VLHWFGPIHRTPLY-UHFFFAOYSA-N 2-[2-(4-oxo-3,1-benzoxazin-2-yl)ethyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(CCC=3OC(=O)C4=CC=CC=C4N=3)=NC2=C1 VLHWFGPIHRTPLY-UHFFFAOYSA-N 0.000 description 1
- PQJFVRDLOVJMPY-UHFFFAOYSA-N 2-[2-(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)ethyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1CCC1=NC(C(C)C)C(=O)O1 PQJFVRDLOVJMPY-UHFFFAOYSA-N 0.000 description 1
- VEENQZKPWOABER-UHFFFAOYSA-N 2-[2-(5-oxo-4h-1,3-oxazol-2-yl)ethyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1CCC1=NCC(=O)O1 VEENQZKPWOABER-UHFFFAOYSA-N 0.000 description 1
- AWZAKUFLIAIORL-UHFFFAOYSA-N 2-[3-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)phenyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1C1=CC=CC(C=2OC(=O)C(C)(C)N=2)=C1 AWZAKUFLIAIORL-UHFFFAOYSA-N 0.000 description 1
- SORNEPWIFZWRMH-UHFFFAOYSA-N 2-[3-(4-oxo-3,1-benzoxazin-2-yl)phenyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(C=3C=CC=C(C=3)C=3OC(C4=CC=CC=C4N=3)=O)=NC2=C1 SORNEPWIFZWRMH-UHFFFAOYSA-N 0.000 description 1
- JRCBWKUHJXPNEX-UHFFFAOYSA-N 2-[3-(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)phenyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1C1=CC=CC(C=2OC(=O)C(C(C)C)N=2)=C1 JRCBWKUHJXPNEX-UHFFFAOYSA-N 0.000 description 1
- ZBSAQMZWFNJJAY-UHFFFAOYSA-N 2-[3-(5-oxo-4h-1,3-oxazol-2-yl)phenyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1C1=CC=CC(C=2OC(=O)CN=2)=C1 ZBSAQMZWFNJJAY-UHFFFAOYSA-N 0.000 description 1
- GCKLGLKRQJLXNN-UHFFFAOYSA-N 2-[4-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)butyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1CCCCC1=NC(C)(C)C(=O)O1 GCKLGLKRQJLXNN-UHFFFAOYSA-N 0.000 description 1
- IQDGOCFFOPHWLN-UHFFFAOYSA-N 2-[4-(4-oxo-3,1-benzoxazin-2-yl)butyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(CCCCC=3OC(=O)C4=CC=CC=C4N=3)=NC2=C1 IQDGOCFFOPHWLN-UHFFFAOYSA-N 0.000 description 1
- UYDSINLMNOLIDT-UHFFFAOYSA-N 2-[4-(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)butyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1CCCCC1=NC(C(C)C)C(=O)O1 UYDSINLMNOLIDT-UHFFFAOYSA-N 0.000 description 1
- ILXWYZXWLRUHJC-UHFFFAOYSA-N 2-[4-(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)phenyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1C1=CC=C(C=2OC(=O)C(C(C)C)N=2)C=C1 ILXWYZXWLRUHJC-UHFFFAOYSA-N 0.000 description 1
- VQWJISOFRUNGDF-UHFFFAOYSA-N 2-[4-(5-oxo-4h-1,3-oxazol-2-yl)butyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1CCCCC1=NCC(=O)O1 VQWJISOFRUNGDF-UHFFFAOYSA-N 0.000 description 1
- XGFJSJXJDMMICL-UHFFFAOYSA-N 2-[4-(5-oxo-4h-1,3-oxazol-2-yl)phenyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1C1=CC=C(C=2OC(=O)CN=2)C=C1 XGFJSJXJDMMICL-UHFFFAOYSA-N 0.000 description 1
- QYDLRLMAAAQEJO-UHFFFAOYSA-N 2-[6-(4,4-dimethyl-5-oxo-1,3-oxazol-2-yl)hexyl]-4,4-dimethyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1CCCCCCC1=NC(C)(C)C(=O)O1 QYDLRLMAAAQEJO-UHFFFAOYSA-N 0.000 description 1
- GUGNJNZNMSOYGT-UHFFFAOYSA-N 2-[6-(4-oxo-3,1-benzoxazin-2-yl)hexyl]-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(CCCCCCC=3OC(=O)C4=CC=CC=C4N=3)=NC2=C1 GUGNJNZNMSOYGT-UHFFFAOYSA-N 0.000 description 1
- RMCCLDYXKPJFOC-UHFFFAOYSA-N 2-[6-(5-oxo-4-propan-2-yl-4h-1,3-oxazol-2-yl)hexyl]-4-propan-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C(C)C)N=C1CCCCCCC1=NC(C(C)C)C(=O)O1 RMCCLDYXKPJFOC-UHFFFAOYSA-N 0.000 description 1
- AAMDZCJYHVRVGV-UHFFFAOYSA-N 2-[6-(5-oxo-4h-1,3-oxazol-2-yl)hexyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1CCCCCCC1=NCC(=O)O1 AAMDZCJYHVRVGV-UHFFFAOYSA-N 0.000 description 1
- FWACJXSHEZUCSG-UHFFFAOYSA-N 2-methyl-6-[(2-methyl-4-oxo-3,1-benzoxazin-6-yl)methyl]-3,1-benzoxazin-4-one Chemical compound N1=C(C)OC(=O)C2=CC(CC3=CC=C4N=C(OC(=O)C4=C3)C)=CC=C21 FWACJXSHEZUCSG-UHFFFAOYSA-N 0.000 description 1
- GBYFEFHQXLNYJE-UHFFFAOYSA-N 2-naphthalen-2-yl-3,1-benzoxazin-4-one Chemical compound C1=CC=CC2=CC(C=3OC(C4=CC=CC=C4N=3)=O)=CC=C21 GBYFEFHQXLNYJE-UHFFFAOYSA-N 0.000 description 1
- BBQPVSIIXLPVTA-UHFFFAOYSA-N 2-naphthalen-2-yl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)CN=C1C1=CC=C(C=CC=C2)C2=C1 BBQPVSIIXLPVTA-UHFFFAOYSA-N 0.000 description 1
- KXERQWRKBSGUMN-UHFFFAOYSA-N 2-nitro-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=C1)C(=O)OC(=N2)[N+](=O)[O-] KXERQWRKBSGUMN-UHFFFAOYSA-N 0.000 description 1
- QKCKCXFWENOGER-UHFFFAOYSA-N 2-phenyloxazol-5(4H)-one Chemical compound O1C(=O)CN=C1C1=CC=CC=C1 QKCKCXFWENOGER-UHFFFAOYSA-N 0.000 description 1
- LNARBTSTFCUKML-UHFFFAOYSA-N 4,4-dimethyl-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)(C)N=C1C1=CC=CC=C1 LNARBTSTFCUKML-UHFFFAOYSA-N 0.000 description 1
- PHGJBXLIMZOGAN-UHFFFAOYSA-N 4-(2-methylpropyl)-2-[2-[4-(2-methylpropyl)-5-oxo-4h-1,3-oxazol-2-yl]ethyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(CC(C)C)N=C1CCC1=NC(CC(C)C)C(=O)O1 PHGJBXLIMZOGAN-UHFFFAOYSA-N 0.000 description 1
- HKBLCYFNESISIY-UHFFFAOYSA-N 4-(2-methylpropyl)-2-[3-[4-(2-methylpropyl)-5-oxo-4h-1,3-oxazol-2-yl]phenyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(CC(C)C)N=C1C1=CC=CC(C=2OC(=O)C(CC(C)C)N=2)=C1 HKBLCYFNESISIY-UHFFFAOYSA-N 0.000 description 1
- CWSQHIFYUFIBTO-UHFFFAOYSA-N 4-(2-methylpropyl)-2-[4-[4-(2-methylpropyl)-5-oxo-4h-1,3-oxazol-2-yl]phenyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(CC(C)C)N=C1C1=CC=C(C=2OC(=O)C(CC(C)C)N=2)C=C1 CWSQHIFYUFIBTO-UHFFFAOYSA-N 0.000 description 1
- GZQTUSFXPKQVPG-UHFFFAOYSA-N 4-(2-methylpropyl)-2-[6-[4-(2-methylpropyl)-5-oxo-4h-1,3-oxazol-2-yl]hexyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(CC(C)C)N=C1CCCCCCC1=NC(CC(C)C)C(=O)O1 GZQTUSFXPKQVPG-UHFFFAOYSA-N 0.000 description 1
- YWEHSBFBCPLPRK-UHFFFAOYSA-N 4-(2-methylpropyl)-2-[[4-(2-methylpropyl)-5-oxo-4h-1,3-oxazol-2-yl]methyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(CC(C)C)N=C1CC1=NC(CC(C)C)C(=O)O1 YWEHSBFBCPLPRK-UHFFFAOYSA-N 0.000 description 1
- OPHIINOMBFPLBL-UHFFFAOYSA-N 4-(2-methylpropyl)-2-phenyl-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(CC(C)C)N=C1C1=CC=CC=C1 OPHIINOMBFPLBL-UHFFFAOYSA-N 0.000 description 1
- JHAWCQQLNBHSIB-UHFFFAOYSA-N 4-methyl-2-[(4-methyl-5-oxo-4h-1,3-oxazol-2-yl)methyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)N=C1CC1=NC(C)C(=O)O1 JHAWCQQLNBHSIB-UHFFFAOYSA-N 0.000 description 1
- JCOSXJNAQFCARR-UHFFFAOYSA-N 4-methyl-2-[10-(4-methyl-5-oxo-4h-1,3-oxazol-2-yl)decyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)N=C1CCCCCCCCCCC1=NC(C)C(=O)O1 JCOSXJNAQFCARR-UHFFFAOYSA-N 0.000 description 1
- NDGHTEABFVIVHK-UHFFFAOYSA-N 4-methyl-2-[2-(4-methyl-5-oxo-4h-1,3-oxazol-2-yl)ethyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)N=C1CCC1=NC(C)C(=O)O1 NDGHTEABFVIVHK-UHFFFAOYSA-N 0.000 description 1
- HIVQLZGHAAODNQ-UHFFFAOYSA-N 4-methyl-2-[6-(4-methyl-5-oxo-4h-1,3-oxazol-2-yl)hexyl]-4h-1,3-oxazol-5-one Chemical compound O1C(=O)C(C)N=C1CCCCCCC1=NC(C)C(=O)O1 HIVQLZGHAAODNQ-UHFFFAOYSA-N 0.000 description 1
- FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical class O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 239000004305 biphenyl Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005760 substituted naphthylene group Chemical group 0.000 description 1
Landscapes
- Polyamides (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6686279A JPS55160025A (en) | 1979-05-31 | 1979-05-31 | Production of modified polyamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6686279A JPS55160025A (en) | 1979-05-31 | 1979-05-31 | Production of modified polyamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55160025A JPS55160025A (en) | 1980-12-12 |
| JPS6154045B2 true JPS6154045B2 (enExample) | 1986-11-20 |
Family
ID=13328081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6686279A Granted JPS55160025A (en) | 1979-05-31 | 1979-05-31 | Production of modified polyamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55160025A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2694008B1 (fr) * | 1992-07-24 | 1994-10-21 | Atochem Elf Sa | Polymères et copolymères issus de l'addition d'oligomères à terminaisons di-amino et di-hydroxy et de bisoxazinones ou de bisoxazolinones, et leur procédé d'obtention. |
| DE4410539A1 (de) * | 1994-03-26 | 1995-09-28 | Sandoz Ag | Verwendung von 4 H-3,1-Benzoxazin-4-on-Verbindungen zur Verbesserung der Lichtechtheit von Textilmaterialien |
| US6951905B2 (en) * | 2000-01-26 | 2005-10-04 | Qinetiq Limited | Bisoxazolone based polymers |
-
1979
- 1979-05-31 JP JP6686279A patent/JPS55160025A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55160025A (en) | 1980-12-12 |
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