CN100402538C - 大分子型的多酰基氧化膦光引发剂及生产方法 - Google Patents
大分子型的多酰基氧化膦光引发剂及生产方法 Download PDFInfo
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- CN100402538C CN100402538C CNB2006100881461A CN200610088146A CN100402538C CN 100402538 C CN100402538 C CN 100402538C CN B2006100881461 A CNB2006100881461 A CN B2006100881461A CN 200610088146 A CN200610088146 A CN 200610088146A CN 100402538 C CN100402538 C CN 100402538C
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- Prior art keywords
- many
- alkyl
- compound
- acylphosphine oxides
- light trigger
- 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.)
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- -1 phosphine imide Chemical class 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 230000000977 initiatory effect Effects 0.000 title description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 150000001805 chlorine compounds Chemical class 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229920000570 polyether Polymers 0.000 claims description 13
- 229920000728 polyester Polymers 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 7
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 238000012661 block copolymerization Methods 0.000 claims description 3
- CAHISRVKQBZLDQ-UHFFFAOYSA-N ethoxyphosphinous acid Chemical compound CCOPO CAHISRVKQBZLDQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005447 octyloxy 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])O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 5
- 239000011230 binding agent Substances 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 239000003999 initiator Substances 0.000 abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract 1
- 241000482268 Zea mays subsp. mays Species 0.000 abstract 1
- 239000000976 ink Substances 0.000 abstract 1
- 239000002367 phosphate rock Substances 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 150000003457 sulfones Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000005516 engineering process Methods 0.000 description 8
- 238000010792 warming Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229920000909 polytetrahydrofuran Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- VZEGPPPCKHRYGO-UHFFFAOYSA-N diethoxyphosphorylbenzene Chemical compound CCOP(=O)(OCC)C1=CC=CC=C1 VZEGPPPCKHRYGO-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
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- Polyesters Or Polycarbonates (AREA)
Abstract
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CNB2006100881461A CN100402538C (zh) | 2006-06-28 | 2006-06-28 | 大分子型的多酰基氧化膦光引发剂及生产方法 |
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CNB2006100881461A CN100402538C (zh) | 2006-06-28 | 2006-06-28 | 大分子型的多酰基氧化膦光引发剂及生产方法 |
Publications (2)
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CN1896083A CN1896083A (zh) | 2007-01-17 |
CN100402538C true CN100402538C (zh) | 2008-07-16 |
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CNB2006100881461A Expired - Fee Related CN100402538C (zh) | 2006-06-28 | 2006-06-28 | 大分子型的多酰基氧化膦光引发剂及生产方法 |
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JP6016768B2 (ja) * | 2013-02-21 | 2016-10-26 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、及び、高分子開始剤 |
CN112334551B (zh) * | 2018-06-19 | 2022-11-08 | 爱克发有限公司 | 酰基氧化膦引发剂 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4298738A (en) * | 1979-03-14 | 1981-11-03 | Basf Aktiengesellschaft | Acylphosphine oxide compounds their preparation and use |
CN1659175A (zh) * | 2002-06-11 | 2005-08-24 | 西巴特殊化学品控股有限公司 | 单酰基和二酰基氧化膦的多聚体形式 |
-
2006
- 2006-06-28 CN CNB2006100881461A patent/CN100402538C/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4298738A (en) * | 1979-03-14 | 1981-11-03 | Basf Aktiengesellschaft | Acylphosphine oxide compounds their preparation and use |
CN1659175A (zh) * | 2002-06-11 | 2005-08-24 | 西巴特殊化学品控股有限公司 | 单酰基和二酰基氧化膦的多聚体形式 |
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C06 | Publication | ||
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Changshang Newsun Chemical Industry Co.,Ltd. Assignor: NANTONGYOUSHANG CHEMICAL Co.,Ltd. Contract record no.: 2010430000028 Denomination of invention: Macromolecular polyacyl phosphine imide light initiating agent and its production Granted publication date: 20080716 License type: Exclusive License Open date: 20070117 Record date: 20100428 |
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C56 | Change in the name or address of the patentee |
Owner name: NANTONG XINYU CHEMICAL CO., LTD. Free format text: FORMER NAME: NANTONGYOUSHANG CHEMICAL CO., LTD. |
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CP03 | Change of name, title or address |
Address after: 226532, 2, Qianjiang Road, fine chemical industrial park, Rugao port, Jiangsu, Rugao Patentee after: NANTONG XINYU CHEMICAL ENGINEERING CO.,LTD. Address before: 226532 No. 1, chemical Avenue, fine chemical industrial park, Rugao Port Economic Development Zone, Jiangsu, Rugao Patentee before: NANTONGYOUSHANG CHEMICAL Co.,Ltd. |
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CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080716 |