WO2005040083A1 - White solid photoinitiator in the form of powder and preparation thereof - Google Patents
White solid photoinitiator in the form of powder and preparation thereof Download PDFInfo
- Publication number
- WO2005040083A1 WO2005040083A1 PCT/EP2004/052532 EP2004052532W WO2005040083A1 WO 2005040083 A1 WO2005040083 A1 WO 2005040083A1 EP 2004052532 W EP2004052532 W EP 2004052532W WO 2005040083 A1 WO2005040083 A1 WO 2005040083A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- hydroxy
- phenyl
- propan
- phenoxy
- Prior art date
Links
- 239000000843 powder Substances 0.000 title claims abstract description 23
- 239000007787 solid Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- LYGZOGDWCOYSGJ-UHFFFAOYSA-N 2-hydroxy-1-[4-[4-(2-hydroxy-2-methylpropanoyl)phenoxy]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1OC1=CC=C(C(=O)C(C)(C)O)C=C1 LYGZOGDWCOYSGJ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 14
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- MFEWNFVBWPABCX-UHFFFAOYSA-N 1,1,2,2-tetraphenylethane-1,2-diol Chemical class C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 MFEWNFVBWPABCX-UHFFFAOYSA-N 0.000 description 1
- JZKPKNSYAHAKJY-UHFFFAOYSA-N 1-[4-(4-benzoylphenyl)sulfanylphenyl]-2-methyl-2-(4-methylphenyl)sulfonylpropan-1-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C)(C)C(=O)C(C=C1)=CC=C1SC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 JZKPKNSYAHAKJY-UHFFFAOYSA-N 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UKASIOIEWZDBIT-UHFFFAOYSA-N phenyl-(2,3,4-trimethylphenyl)methanone Chemical compound CC1=C(C)C(C)=CC=C1C(=O)C1=CC=CC=C1 UKASIOIEWZDBIT-UHFFFAOYSA-N 0.000 description 1
- JZDGWLGMEGSUGH-UHFFFAOYSA-N phenyl-(2,4,6-trimethylbenzoyl)phosphinic acid Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(O)(=O)C1=CC=CC=C1 JZDGWLGMEGSUGH-UHFFFAOYSA-N 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 231100000489 sensitizer Toxicity 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920006302 stretch film Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE602004024442T DE602004024442D1 (en) | 2003-10-27 | 2004-10-14 | WHITE SOLID PHOTOINITIATOR IN THE FORM OF A POWDER AND ITS MANUFACTURE |
US10/577,194 US7482392B2 (en) | 2003-10-27 | 2004-10-14 | White solid photoinitiator in the form of powder and preparation thereof |
AT04791220T ATE450494T1 (en) | 2003-10-27 | 2004-10-14 | WHITE SOLID PHOTOINITIATOR IN THE FORM OF A POWDER AND PRODUCTION THEREOF |
CA2541993A CA2541993C (en) | 2003-10-27 | 2004-10-14 | White solid photoinitiator in the form of powder and preparation thereof |
EP04791220A EP1692088B1 (en) | 2003-10-27 | 2004-10-14 | White solid photoinitiator in the form of powder and preparation thereof |
BRPI0415828-8A BRPI0415828B1 (en) | 2003-10-27 | 2004-10-14 | PROCEDURE FOR PREPARING 2-HYDROXY-1- {4- [4- (2-HYDROXY-2-METHYL-PROPIONYL) -PHENOXY] -FE NIL} -2-METHYL-PROPAN-1-ONA, WHITE SOLID PHOTOINICIATOR, METHOD FOR PREPARATION OF A PHOTO-POLYMERIZABLE SYSTEM, AND METHOD FOR COATING WOOD, PAPER, BOARD, PLASTIC OR METAL SURFACES |
JP2006537276A JP4889496B2 (en) | 2003-10-27 | 2004-10-14 | White solid photoinitiator in powder form and its production |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT000040A ITVA20030040A1 (en) | 2003-10-27 | 2003-10-27 | WHITE SOLID PHOTOINIZER FOR POWDER AND PROCEDURE FOR ITS PREPARATION. |
ITVA2003A000040 | 2003-10-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005040083A1 true WO2005040083A1 (en) | 2005-05-06 |
Family
ID=34509528
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/052532 WO2005040083A1 (en) | 2003-10-27 | 2004-10-14 | White solid photoinitiator in the form of powder and preparation thereof |
Country Status (11)
Country | Link |
---|---|
US (1) | US7482392B2 (en) |
EP (1) | EP1692088B1 (en) |
JP (2) | JP4889496B2 (en) |
CN (1) | CN100436394C (en) |
AT (1) | ATE450494T1 (en) |
BR (1) | BRPI0415828B1 (en) |
CA (1) | CA2541993C (en) |
DE (1) | DE602004024442D1 (en) |
ES (1) | ES2337691T3 (en) |
IT (1) | ITVA20030040A1 (en) |
WO (1) | WO2005040083A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2604663A1 (en) | 2011-12-16 | 2013-06-19 | Agfa Graphics N.V. | Curable liquids and inkjet inks for food packaging applications |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2388046A1 (en) | 1999-11-05 | 2001-05-17 | Z Corporation | Material systems and methods of three-dimensional printing |
ITVA20030040A1 (en) * | 2003-10-27 | 2005-04-28 | Lamberti Spa | WHITE SOLID PHOTOINIZER FOR POWDER AND PROCEDURE FOR ITS PREPARATION. |
KR20070083840A (en) * | 2004-10-29 | 2007-08-24 | 다이니혼 잉키 가가쿠 고교 가부시키가이샤 | Active energy ray-curable inkjet recording ink |
EP2664442B1 (en) | 2006-12-08 | 2018-02-14 | 3D Systems Incorporated | Three dimensional printing material system |
WO2008086033A1 (en) | 2007-01-10 | 2008-07-17 | Z Corporation | Three-dimensional printing material system with improved color, article performance, and ease of use |
WO2008103450A2 (en) | 2007-02-22 | 2008-08-28 | Z Corporation | Three dimensional printing material system and method using plasticizer-assisted sintering |
JP2009170138A (en) * | 2008-01-11 | 2009-07-30 | Sony Corp | Manufacturing method of display device, composition for display device manufacture, and display device |
CN101724099B (en) * | 2009-12-18 | 2012-09-26 | 深圳市有为化学技术有限公司 | Aromatic ketone compound and photoinitiator with same |
CN102924630A (en) * | 2011-08-09 | 2013-02-13 | 陈婷 | UV light curing application system containing amino ketone compound 1-([1,1'-biphenyl]-4-yl)-2-methyl-2-morpholinopropan-1-one |
CN102744991A (en) * | 2012-07-30 | 2012-10-24 | 昆山科望快速印务有限公司 | Printing technology |
JP6123529B2 (en) * | 2013-07-05 | 2017-05-10 | 株式会社リコー | Photopolymerizable inkjet ink, ink cartridge, and inkjet recording apparatus |
WO2015045857A1 (en) | 2013-09-30 | 2015-04-02 | 富士フイルム株式会社 | METHOD FOR PRODUCING α-HALOGENOACETOPHENON COMPOUND, AND α-BROMOACETOPHENON COMPOUND |
CN111138260B (en) * | 2019-12-31 | 2022-10-14 | 天津久日新材料股份有限公司 | Preparation method of alpha-hydroxyketone bifunctional photoinitiator |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US3340233A (en) * | 1963-07-22 | 1967-09-05 | Dow Chemical Co | Bis-vinylketo aromatic compounds and polymerization products thereof |
EP0003002A2 (en) * | 1977-12-22 | 1979-07-11 | Ciba-Geigy Ag | Use of aromatic-aliphatic ketones as photoinitiators, photopolymerisable systems containing such ketones and aromatic-aliphatic ketones |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4474990A (en) * | 1981-07-08 | 1984-10-02 | Raychem Corporation | Preparing p-phenoxy benzoyl compounds |
IT1176018B (en) * | 1984-04-12 | 1987-08-12 | Lamberti Flli Spa | ALIPHATIC POLYMERIC OR POLYMERIZABLE AROMATIC KETONES SUITABLE FOR USE AS A POLYMERIZATION PHOTO INITIATOR |
DE3512179A1 (en) * | 1985-04-03 | 1986-12-04 | Merck Patent Gmbh, 6100 Darmstadt | PHOTO INITIATORS FOR PHOTOPOLYMERIZATION IN AQUEOUS SYSTEMS |
JPH06102698B2 (en) * | 1990-04-27 | 1994-12-14 | 積水化学工業株式会社 | Photopolymerizable composition |
US5118860A (en) * | 1990-11-27 | 1992-06-02 | Hoechst Celanese Corporation | Bf3 catalyzed acylation of aromatic compounds |
JPH1090891A (en) * | 1996-09-10 | 1998-04-10 | Fuji Photo Film Co Ltd | Photopolymerizable composition |
PT1140761E (en) * | 1999-01-12 | 2004-02-27 | Clariant Finance Bvi Ltd | BENZOFENONAS AND THEIR USE AS PHOTO-INITIATORS |
WO2004009651A1 (en) * | 2002-07-19 | 2004-01-29 | Ciba Specialty Chemicals Holding Inc. | New difunctional photoinitiators |
JP2006526678A (en) * | 2003-06-03 | 2006-11-24 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Process for producing pigment concentrates for use in radiation curable coatings |
ITVA20030028A1 (en) * | 2003-08-07 | 2005-02-08 | Lamberti Spa | TRANSPARENT PHOTOPOLYMIZED SYSTEMS FOR THE PREPARATION OF HIGH THICKNESS COATINGS. |
ITVA20030040A1 (en) * | 2003-10-27 | 2005-04-28 | Lamberti Spa | WHITE SOLID PHOTOINIZER FOR POWDER AND PROCEDURE FOR ITS PREPARATION. |
-
2003
- 2003-10-27 IT IT000040A patent/ITVA20030040A1/en unknown
-
2004
- 2004-10-14 WO PCT/EP2004/052532 patent/WO2005040083A1/en active Application Filing
- 2004-10-14 AT AT04791220T patent/ATE450494T1/en not_active IP Right Cessation
- 2004-10-14 JP JP2006537276A patent/JP4889496B2/en active Active
- 2004-10-14 US US10/577,194 patent/US7482392B2/en active Active
- 2004-10-14 DE DE602004024442T patent/DE602004024442D1/en active Active
- 2004-10-14 BR BRPI0415828-8A patent/BRPI0415828B1/en active IP Right Grant
- 2004-10-14 CA CA2541993A patent/CA2541993C/en not_active Expired - Fee Related
- 2004-10-14 ES ES04791220T patent/ES2337691T3/en active Active
- 2004-10-14 CN CNB2004800315364A patent/CN100436394C/en active Active
- 2004-10-14 EP EP04791220A patent/EP1692088B1/en active Active
-
2011
- 2011-10-21 JP JP2011232028A patent/JP2012051927A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3340233A (en) * | 1963-07-22 | 1967-09-05 | Dow Chemical Co | Bis-vinylketo aromatic compounds and polymerization products thereof |
EP0003002A2 (en) * | 1977-12-22 | 1979-07-11 | Ciba-Geigy Ag | Use of aromatic-aliphatic ketones as photoinitiators, photopolymerisable systems containing such ketones and aromatic-aliphatic ketones |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2604663A1 (en) | 2011-12-16 | 2013-06-19 | Agfa Graphics N.V. | Curable liquids and inkjet inks for food packaging applications |
WO2013087427A1 (en) | 2011-12-16 | 2013-06-20 | Agfa Graphics Nv | Curable liquids and inkjet inks for food packaging applications |
Also Published As
Publication number | Publication date |
---|---|
CA2541993A1 (en) | 2005-05-06 |
BRPI0415828A (en) | 2007-01-02 |
US7482392B2 (en) | 2009-01-27 |
JP4889496B2 (en) | 2012-03-07 |
CN1871200A (en) | 2006-11-29 |
BRPI0415828B1 (en) | 2014-08-05 |
JP2007513069A (en) | 2007-05-24 |
JP2012051927A (en) | 2012-03-15 |
EP1692088A1 (en) | 2006-08-23 |
CN100436394C (en) | 2008-11-26 |
CA2541993C (en) | 2012-09-11 |
US20070135531A1 (en) | 2007-06-14 |
EP1692088B1 (en) | 2009-12-02 |
ITVA20030040A1 (en) | 2005-04-28 |
DE602004024442D1 (en) | 2010-01-14 |
ES2337691T3 (en) | 2010-04-28 |
ATE450494T1 (en) | 2009-12-15 |
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