CN102585223B - Long carbon chain semi-aromatic polyamide-imide and synthesis method thereof - Google Patents
Long carbon chain semi-aromatic polyamide-imide and synthesis method thereof Download PDFInfo
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- CN102585223B CN102585223B CN 201110450285 CN201110450285A CN102585223B CN 102585223 B CN102585223 B CN 102585223B CN 201110450285 CN201110450285 CN 201110450285 CN 201110450285 A CN201110450285 A CN 201110450285A CN 102585223 B CN102585223 B CN 102585223B
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- diamine
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- imide
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- diamines
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- 239000004962 Polyamide-imide Substances 0.000 title abstract 7
- 229920002312 polyamide-imide Polymers 0.000 title abstract 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title abstract 4
- 238000001308 synthesis method Methods 0.000 title abstract 3
- -1 diamine compound Chemical class 0.000 claims abstract description 25
- 239000000126 substance Substances 0.000 claims abstract description 16
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 14
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 claims abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 150000003949 imides Chemical class 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229920006012 semi-aromatic polyamide Polymers 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 238000010189 synthetic method Methods 0.000 claims description 10
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 claims description 8
- 238000009413 insulation Methods 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 8
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 8
- 239000001488 sodium phosphate Substances 0.000 claims description 8
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 8
- 238000007599 discharging Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 5
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 4
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims description 4
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 3
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 claims description 2
- JCUZDQXWVYNXHD-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diamine Chemical compound NCCC(C)CC(C)(C)CN JCUZDQXWVYNXHD-UHFFFAOYSA-N 0.000 claims description 2
- YXOKJIRTNWHPFS-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diamine Chemical compound NCC(C)CCC(C)CN YXOKJIRTNWHPFS-UHFFFAOYSA-N 0.000 claims description 2
- BUGIFNPYQVKODR-UHFFFAOYSA-N 2-methylhexane-1,6-diamine Chemical compound NCC(C)CCCCN BUGIFNPYQVKODR-UHFFFAOYSA-N 0.000 claims description 2
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 2
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical compound CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000005453 pelletization Methods 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000004953 Aliphatic polyamide Substances 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 229920003231 aliphatic polyamide Polymers 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C)(*)[N+](NC)[O-] Chemical compound CC(C)(*)[N+](NC)[O-] 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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CN 201110450285 CN102585223B (en) | 2011-12-29 | 2011-12-29 | Long carbon chain semi-aromatic polyamide-imide and synthesis method thereof |
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CN 201110450285 CN102585223B (en) | 2011-12-29 | 2011-12-29 | Long carbon chain semi-aromatic polyamide-imide and synthesis method thereof |
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CN102585223A CN102585223A (en) | 2012-07-18 |
CN102585223B true CN102585223B (en) | 2013-08-28 |
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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TWI507576B (en) * | 2012-12-26 | 2015-11-11 | Taiwan Textile Res Inst | Modified long chain polyamide |
CN105237767A (en) * | 2015-07-25 | 2016-01-13 | 常州大学 | Liquid-crystal polyamide imide and preparation method therefor |
KR102430056B1 (en) | 2017-09-08 | 2022-08-05 | 삼성전자주식회사 | Poly(amide-imide) copolymer, composition for preparing poly(amide-imide) copolymer, article including poly(amide-imide) copolymer, and display device including the article |
CN115678276A (en) * | 2022-12-14 | 2023-02-03 | 宁波东鑫高强度螺帽有限公司 | Fastener for composite material |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE756218A (en) * | 1969-09-16 | 1971-03-01 | Bayer Ag | IMIDOCARBOXYLIC ACID PRODUCTION PROCESS |
US3961009A (en) * | 1970-04-22 | 1976-06-01 | Toray Industries, Inc. | Process for the production of a shaped article of a heat resistant polymer |
FR2932486B1 (en) * | 2008-06-12 | 2012-12-07 | Rhodia Operations | PROCESS FOR THE PREPARATION OF A POLYAMIDEIMIDE, POLYAMIDEIMIDE AND COMPOSITION COMPRISING THE POLYAMIDEIMIDE |
CN102532545B (en) * | 2011-12-29 | 2013-11-06 | 东莞市信诺橡塑工业有限公司 | Long-carbon-chain semi-aromatic polyamide imide and synthetic method thereof |
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Denomination of invention: Long carbon chain semi-aromatic polyamide-imide and synthesis method thereof Effective date of registration: 20140924 Granted publication date: 20130828 Pledgee: Guangdong Development Bank Limited by Share Ltd. Dongguan Humen branch Pledgor: DONGGUAN SINOPLAST INDUSTRIAL Ltd. Registration number: 2014990000803 |
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Date of cancellation: 20151130 Granted publication date: 20130828 Pledgee: Guangdong Development Bank Limited by Share Ltd. Dongguan Humen branch Pledgor: DONGGUAN SINOPLAST INDUSTRIAL Ltd. Registration number: 2014990000803 |
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Address after: 355 No. 523850 Guangdong city in Dongguan Province town of Changan Wusha Cun BBK Avenue Patentee after: GUANGDONG SINOPLAST ADVANCED MATERIAL CO.,LTD. Address before: 355 No. 523860 Guangdong city in Dongguan Province town of Changan Wusha Cun BBK Avenue Patentee before: DONGGUAN SINOPLAST INDUSTRIAL Ltd. |
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Address after: 523850 Baibugao Avenue, Wushajiang, Chang'an Town, Dongguan City, Guangdong Province, 355 Patentee after: Guangdong Sinoplast New Materials Co.,Ltd. Address before: 523850 Baibugao Avenue, Wushajiang, Chang'an Town, Dongguan City, Guangdong Province, 355 Patentee before: GUANGDONG SINOPLAST ADVANCED MATERIAL CO.,LTD. |