CN113527229B - 叔胺型苯甲酸酯化合物及其制备方法、光固化组合物 - Google Patents
叔胺型苯甲酸酯化合物及其制备方法、光固化组合物 Download PDFInfo
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- CN113527229B CN113527229B CN202010318405.5A CN202010318405A CN113527229B CN 113527229 B CN113527229 B CN 113527229B CN 202010318405 A CN202010318405 A CN 202010318405A CN 113527229 B CN113527229 B CN 113527229B
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- Prior art keywords
- tertiary amine
- substituted
- compound
- unsubstituted
- benzoate compound
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- -1 Tertiary amine benzoate compound Chemical class 0.000 title claims abstract description 97
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000000016 photochemical curing Methods 0.000 title abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 9
- 239000012670 alkaline solution Substances 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 4
- 238000007142 ring opening reaction Methods 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000003444 phase transfer catalyst Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 11
- 238000013508 migration Methods 0.000 abstract description 9
- 230000005012 migration Effects 0.000 abstract description 9
- 238000001723 curing Methods 0.000 abstract description 7
- 239000011159 matrix material Substances 0.000 abstract description 6
- 239000003999 initiator Substances 0.000 abstract description 5
- 239000011347 resin Substances 0.000 abstract description 5
- 229920005989 resin Polymers 0.000 abstract description 5
- 150000003512 tertiary amines Chemical class 0.000 description 15
- 239000000976 ink Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 125000003884 phenylalkyl group Chemical group 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000852 hydrogen donor Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 1
- KJSGODDTWRXQRH-UHFFFAOYSA-N 2-(dimethylamino)ethyl benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC=C1 KJSGODDTWRXQRH-UHFFFAOYSA-N 0.000 description 1
- SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (14)
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CN202010318405.5A CN113527229B (zh) | 2020-04-21 | 2020-04-21 | 叔胺型苯甲酸酯化合物及其制备方法、光固化组合物 |
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CN202010318405.5A CN113527229B (zh) | 2020-04-21 | 2020-04-21 | 叔胺型苯甲酸酯化合物及其制备方法、光固化组合物 |
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CN113527229B true CN113527229B (zh) | 2023-09-12 |
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Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101519462A (zh) * | 2009-03-20 | 2009-09-02 | 常州强力电子新材料有限公司 | 光引发剂用叔胺增感剂及其制备方法 |
CN101979373A (zh) * | 2010-09-28 | 2011-02-23 | 北京英力科技发展有限公司 | 低迁移性邻苯甲酰基苯甲酸酯 |
CN102532967A (zh) * | 2011-12-17 | 2012-07-04 | 东莞隽思印刷有限公司 | 一种可用于uv-led光源快速固化涂料及其制备方法 |
WO2015032069A1 (zh) * | 2013-09-06 | 2015-03-12 | 北京英力科技发展有限公司 | 一种低迁移性光引发剂 |
CN110317320A (zh) * | 2018-03-28 | 2019-10-11 | 常州格林感光新材料有限公司 | 阳离子型光固化化合物及包含其的组合物 |
CN110713561A (zh) * | 2018-07-12 | 2020-01-21 | 常州强力电子新材料股份有限公司 | 环氧改性的丙烯酸树脂及其制备方法 |
CN110713797A (zh) * | 2018-07-12 | 2020-01-21 | 常州强力电子新材料股份有限公司 | 环氧接枝松香及其制备方法、包含该环氧接枝松香的组合物及其应用 |
CN110713593A (zh) * | 2018-07-12 | 2020-01-21 | 常州强力电子新材料股份有限公司 | 环氧改性聚酯树脂及其制备方法、包含该环氧改性聚酯树脂的组合物及其应用 |
CN110845702A (zh) * | 2018-08-21 | 2020-02-28 | 常州强力电子新材料股份有限公司 | 可能量固化的超支化环氧树脂、含有其的可能量固化组合物及应用 |
CN110845628A (zh) * | 2018-08-21 | 2020-02-28 | 常州强力电子新材料股份有限公司 | 可能量固化的环氧接枝改性硝酸纤维素、含有其的可能量固化组合物及应用 |
-
2020
- 2020-04-21 CN CN202010318405.5A patent/CN113527229B/zh active Active
Patent Citations (10)
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CN101519462A (zh) * | 2009-03-20 | 2009-09-02 | 常州强力电子新材料有限公司 | 光引发剂用叔胺增感剂及其制备方法 |
CN101979373A (zh) * | 2010-09-28 | 2011-02-23 | 北京英力科技发展有限公司 | 低迁移性邻苯甲酰基苯甲酸酯 |
CN102532967A (zh) * | 2011-12-17 | 2012-07-04 | 东莞隽思印刷有限公司 | 一种可用于uv-led光源快速固化涂料及其制备方法 |
WO2015032069A1 (zh) * | 2013-09-06 | 2015-03-12 | 北京英力科技发展有限公司 | 一种低迁移性光引发剂 |
CN110317320A (zh) * | 2018-03-28 | 2019-10-11 | 常州格林感光新材料有限公司 | 阳离子型光固化化合物及包含其的组合物 |
CN110713561A (zh) * | 2018-07-12 | 2020-01-21 | 常州强力电子新材料股份有限公司 | 环氧改性的丙烯酸树脂及其制备方法 |
CN110713797A (zh) * | 2018-07-12 | 2020-01-21 | 常州强力电子新材料股份有限公司 | 环氧接枝松香及其制备方法、包含该环氧接枝松香的组合物及其应用 |
CN110713593A (zh) * | 2018-07-12 | 2020-01-21 | 常州强力电子新材料股份有限公司 | 环氧改性聚酯树脂及其制备方法、包含该环氧改性聚酯树脂的组合物及其应用 |
CN110845702A (zh) * | 2018-08-21 | 2020-02-28 | 常州强力电子新材料股份有限公司 | 可能量固化的超支化环氧树脂、含有其的可能量固化组合物及应用 |
CN110845628A (zh) * | 2018-08-21 | 2020-02-28 | 常州强力电子新材料股份有限公司 | 可能量固化的环氧接枝改性硝酸纤维素、含有其的可能量固化组合物及应用 |
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