CN106589237B - 基于Diels-Alder点击化学的复合型大分子光稳定剂及其制备方法 - Google Patents
基于Diels-Alder点击化学的复合型大分子光稳定剂及其制备方法 Download PDFInfo
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- CN106589237B CN106589237B CN201610920706.9A CN201610920706A CN106589237B CN 106589237 B CN106589237 B CN 106589237B CN 201610920706 A CN201610920706 A CN 201610920706A CN 106589237 B CN106589237 B CN 106589237B
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- light stabilizer
- diels
- maleimide
- aminomethyl
- macromolecular light
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- 239000004611 light stabiliser Substances 0.000 title claims abstract description 70
- 150000001875 compounds Chemical class 0.000 title claims abstract description 49
- 238000005698 Diels-Alder reaction Methods 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims abstract description 50
- -1 tetramethylpiperidinol maleimidopropionic acid esters Chemical class 0.000 claims abstract description 30
- 239000000178 monomer Substances 0.000 claims abstract description 24
- 150000002148 esters Chemical class 0.000 claims abstract description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 17
- 229920002866 paraformaldehyde Polymers 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 13
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 12
- 229940043237 diethanolamine Drugs 0.000 claims description 12
- 239000002994 raw material Substances 0.000 claims description 12
- IUTPJBLLJJNPAJ-UHFFFAOYSA-N 3-(2,5-dioxopyrrol-1-yl)propanoic acid Chemical compound OC(=O)CCN1C(=O)C=CC1=O IUTPJBLLJJNPAJ-UHFFFAOYSA-N 0.000 claims description 11
- WCILBWLDYPEMNA-UHFFFAOYSA-N 3-(2,5-dioxopyrrol-3-yl)propanoic acid Chemical compound OC(=O)CCC1=CC(=O)NC1=O WCILBWLDYPEMNA-UHFFFAOYSA-N 0.000 claims description 11
- 230000001376 precipitating effect Effects 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 239000002131 composite material Substances 0.000 claims description 9
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000005457 ice water Substances 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 229940116351 sebacate Drugs 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 claims description 5
- 238000003760 magnetic stirring Methods 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 4
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 230000002292 Radical scavenging effect Effects 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 229920000305 Nylon 6,10 Polymers 0.000 abstract 1
- 230000009977 dual effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000001228 spectrum Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000002861 polymer material Substances 0.000 description 8
- 239000002250 absorbent Substances 0.000 description 7
- 230000002745 absorbent Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- GPWJTWDMCFTAPQ-UHFFFAOYSA-N C1(C=CC(N1C(C(=O)O)C)=O)=O.CC1(N(C(CCC1)(C)C)O)C Chemical compound C1(C=CC(N1C(C(=O)O)C)=O)=O.CC1(N(C(CCC1)(C)C)O)C GPWJTWDMCFTAPQ-UHFFFAOYSA-N 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 0 CCC(C(C)(C)C1)C(C)(C)CC1O[N+](C*(C(C(C12)C(C=C3)OC13OC(*C)=O)=O)C2=O)[O-] Chemical compound CCC(C(C)(C)C1)C(C)(C)CC1O[N+](C*(C(C(C12)C(C=C3)OC13OC(*C)=O)=O)C2=O)[O-] 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- NXNBLFIGGAWJLJ-UHFFFAOYSA-N O=C(CCC1CCN=O)C=CC1=O Chemical compound O=C(CCC1CCN=O)C=CC1=O NXNBLFIGGAWJLJ-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- SLSHDMNFHLQTSK-UHFFFAOYSA-N bis(furan-2-ylmethyl) hexanedioate Chemical compound C=1C=COC=1COC(=O)CCCCC(=O)OCC1=CC=CO1 SLSHDMNFHLQTSK-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000009982 effect on human Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/02—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F232/04—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/02—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F232/06—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having two or more carbon-to-carbon double bonds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
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CN201610920706.9A CN106589237B (zh) | 2016-10-21 | 2016-10-21 | 基于Diels-Alder点击化学的复合型大分子光稳定剂及其制备方法 |
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CN201610920706.9A CN106589237B (zh) | 2016-10-21 | 2016-10-21 | 基于Diels-Alder点击化学的复合型大分子光稳定剂及其制备方法 |
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CN101096391A (zh) * | 2007-06-26 | 2008-01-02 | 四川大学 | 高分子化紫外线吸收剂的制备方法 |
CN104419112B (zh) * | 2013-08-19 | 2016-08-17 | 开滦能源化工股份有限公司 | 耐候型聚甲醛复合物及其制备方法 |
CN104231187B (zh) * | 2014-07-30 | 2016-12-07 | 广西师范学院 | 一种两亲性梳状复合型高分子光稳定剂及其制备方法 |
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Address after: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 No. 175 Patentee after: Nanning Normal University Address before: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 Guangxi Teachers Education University No. 175 Patentee before: Guangxi Normal University |
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TR01 | Transfer of patent right |
Effective date of registration: 20191118 Address after: 226200 No.1 Xinglong Road, Chengbei Industrial Park, Qidong City, Nantong City, Jiangsu Province Patentee after: Qidong Hezi New Material Co.,Ltd. Address before: Mingxiu Road East of Nanning city the Guangxi Zhuang Autonomous Region 530001 No. 175 Patentee before: Nanning Normal University |
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Effective date of registration: 20220221 Address after: 226000 Yuelong East Road, Chengbei Industrial Park, Qidong City, Nantong City, Jiangsu Province Patentee after: Jiangsu Duoqi Medical Equipment Co.,Ltd. Address before: 226200 No.1 Xinglong Road, Chengbei Industrial Park, Qidong City, Nantong City, Jiangsu Province Patentee before: Qidong Hezi New Material Co.,Ltd. |
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