CN101550203B - 用于紫外光固化的光引发剂、芳香酮类化合物及其制造方法 - Google Patents
用于紫外光固化的光引发剂、芳香酮类化合物及其制造方法 Download PDFInfo
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- CN101550203B CN101550203B CN2009101069501A CN200910106950A CN101550203B CN 101550203 B CN101550203 B CN 101550203B CN 2009101069501 A CN2009101069501 A CN 2009101069501A CN 200910106950 A CN200910106950 A CN 200910106950A CN 101550203 B CN101550203 B CN 101550203B
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- -1 aromatic ketone compound Chemical class 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title abstract description 12
- 230000005855 radiation Effects 0.000 title abstract 2
- 238000007711 solidification Methods 0.000 title abstract 2
- 230000008023 solidification Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 9
- 150000001263 acyl chlorides Chemical class 0.000 claims abstract description 7
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 6
- 239000004305 biphenyl Substances 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 230000003197 catalytic effect Effects 0.000 claims abstract description 5
- 238000005917 acylation reaction Methods 0.000 claims abstract description 4
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000000016 photochemical curing Methods 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 7
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 3
- 239000004577 thatch Substances 0.000 claims description 3
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- 239000002994 raw material Substances 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 2
- 150000008365 aromatic ketones Chemical class 0.000 abstract 3
- 239000002841 Lewis acid Substances 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 description 36
- 229910052698 phosphorus Inorganic materials 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 238000007363 ring formation reaction Methods 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 9
- 239000003999 initiator Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 4
- 239000012855 volatile organic compound Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YFKPNQBRKCNHMZ-UHFFFAOYSA-N (3-methoxyphenyl)-(4-phenylphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 YFKPNQBRKCNHMZ-UHFFFAOYSA-N 0.000 description 3
- 241000208125 Nicotiana Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 239000012434 nucleophilic reagent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003847 radiation curing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 0 *C(*)(C(c1c(*)c(*)c(*)c(*)c1*)=O)O Chemical compound *C(*)(C(c1c(*)c(*)c(*)c(*)c1*)=O)O 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QEDBLNBIVGFWCD-UHFFFAOYSA-N 2-methyl-2-phenylmethoxy-1-[4-(2-phenylmethoxyethoxy)phenyl]propan-1-one Chemical compound CC(C)(C(=O)C1=CC=C(C=C1)OCCOCC2=CC=CC=C2)OCC3=CC=CC=C3 QEDBLNBIVGFWCD-UHFFFAOYSA-N 0.000 description 1
- XHQZJYCNDZAGLW-UHFFFAOYSA-N 3-methoxybenzoic acid Chemical class COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QUBBCPUGBUEOBA-UHFFFAOYSA-N COC1=CC=C(C=C1)C2=C(C=CC(=C2)C(=O)C3=CC=CC=C3)C4=CC=CC=C4 Chemical compound COC1=CC=C(C=C1)C2=C(C=CC(=C2)C(=O)C3=CC=CC=C3)C4=CC=CC=C4 QUBBCPUGBUEOBA-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
Images
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
序号 | 项目 | 分子式 | 指标(单位:mg/m2) |
0 | 苯 | C6H6 | 不得检出 |
1 | 乙醇 | C2H6O | 50.0 |
2 | 异丙醇 | C3H8O | 5.0 |
3 | 丙酮 | C3H6O | 1.0 |
4 | 丁酮 | C4H8O | 0.5 |
5 | 乙酸乙酯 | C4H8O2 | 10.0 |
6 | 乙酸异丙酯 | C5H10O2 | 5.0 |
7 | 正丁醇 | C4H10O | 2.5 |
8 | 丙二醇甲醚 | C4H10O2 | 60.0 |
9 | 乙酸正丙酯 | C5H10O2 | 50.0 |
10 | 4-甲基-2-戊酮 | C6H12O | 1.0 |
11 | 甲苯 | C7H8 | 0.5 |
12 | 乙酸正丁酯 | C6H12O2 | 5.0 |
13 | 乙苯 | C8H10 | 0.25 |
14 | 二甲苯 | C8H10 | 0.25 |
15 | 环己酮 | C6H10O | 1.0 |
序号 | 项目 | 实施例引发剂SPT-11 | 商用引发剂Irgacure 184 |
0 | 苯 | 未检出 | 0.0446 |
1 | 乙醇 | 1.81 | 3.24 |
2 | 异丙醇 | 0.01 | 0.03 |
3 | 丙酮 | 0.08 | 0.31 |
4 | 丁酮 | 0.01 | 0.03 |
5 | 乙酸乙酯 | 0.70 | 0.21 |
6 | 乙酸异丙酯 | 未检出 | 未检出 |
7 | 正丁醇 | 未检出 | 0.03 |
8 | 丙二醇甲醚 | 0.03 | 0.07 |
9 | 乙酸正丙酯 | 0.02 | 未检出 |
10 | 4-甲基-2-戊酮 | 未检出 | 未检出 |
11 | 甲苯 | 0.06 | 0.02 |
12 | 乙酸正丁酯 | 0.07 | 0.04 |
13 | 乙苯 | 0.01 | 0.03 |
14 | 二甲苯 | 未检出 | 0.03 |
15 | 环己酮 | 0.01 | 158.98 |
统计 | ∑(xi/yi-1) | 0.00 | 157.98 |
Claims (3)
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CN2009101069501A CN101550203B (zh) | 2009-05-08 | 2009-05-08 | 用于紫外光固化的光引发剂、芳香酮类化合物及其制造方法 |
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CN2009101069501A CN101550203B (zh) | 2009-05-08 | 2009-05-08 | 用于紫外光固化的光引发剂、芳香酮类化合物及其制造方法 |
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Publication Number | Publication Date |
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CN101550203A CN101550203A (zh) | 2009-10-07 |
CN101550203B true CN101550203B (zh) | 2011-11-23 |
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Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101812142B (zh) * | 2010-02-05 | 2012-12-26 | 深圳市有为化学技术有限公司 | 双官能团化芳香酮类化合物及含有该类化合物的光引发剂 |
CN101921184A (zh) * | 2010-06-04 | 2010-12-22 | 深圳市有为化学技术有限公司 | 多官能团型芳香酮类化合物及含有该化合物的光引发剂 |
CN103601629B (zh) * | 2010-11-12 | 2015-08-26 | 深圳市有为化学技术有限公司 | 对位或间位官能团化芳香酮类化合物、其制备方法及其光聚合引发剂 |
CN102924630A (zh) * | 2011-08-09 | 2013-02-13 | 陈婷 | 含有胺基酮化合物1-([1,1’-联苯基]-4-基)-2-甲基-2-吗啉基丙烷-1-酮的uv光固化应用体系 |
CN102351676A (zh) * | 2011-08-19 | 2012-02-15 | 滨海锦翔化学助剂有限公司 | 一种高分子羟基酮类光引发剂的制备方法 |
-
2009
- 2009-05-08 CN CN2009101069501A patent/CN101550203B/zh active Active
Non-Patent Citations (1)
Title |
---|
Kumar et al.Friedel-Craft Aroylation of Benzene Biphenyl in Methylene Chloride.《Indian Journal of Chemistry》.1983,第22B卷(第1期),17-22. * |
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Effective date of registration: 20100630 Address after: 518000 12-B room, SED science and technology building, 1 science Road, Shenzhen, Guangdong, Nanshan District Applicant after: SHENZHEN UV-CHEMTECH Co.,Ltd. Address before: 518129, Nanshan District Shenzhen science and Technology Park, Guangdong South University of Hong Kong Research Base Building 305 Applicant before: Shenzhen Dongfangxinwei Technology Co.,Ltd. |
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CP03 | Change of name, title or address | ||
CP03 | Change of name, title or address |
Address after: 518000 Room 2401A, 24th Floor, Coastal Huanqing Building, 24 Futian Street, Zhenzhen Community, Futian Road, Futian District, Shenzhen City, Guangdong Province Patentee after: Shenzhen Youwei Technology Holding Co.,Ltd. Address before: Room 12-B, Sanda Science and Technology Building, No. 1 Science and Technology Road, Nanshan District, Shenzhen City, Guangdong Province, 518000 Patentee before: SHENZHEN UV-CHEMTECH Co.,Ltd. |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Photoinitiators, aromatic ketone compounds for UV curing and their manufacturing methods Effective date of registration: 20201102 Granted publication date: 20111123 Pledgee: Industrial and Commercial Bank of China Limited Shenzhen gaoxinyuan sub branch Pledgor: Shenzhen Youwei Technology Holding Co.,Ltd. Registration number: Y2020980007427 |
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PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20111123 Pledgee: Industrial and Commercial Bank of China Limited Shenzhen gaoxinyuan sub branch Pledgor: Shenzhen Youwei Technology Holding Co.,Ltd. Registration number: Y2020980007427 |