TWI244495B - Process for producing coatings siloxane photoinitiators - Google Patents
Process for producing coatings siloxane photoinitiators Download PDFInfo
- Publication number
- TWI244495B TWI244495B TW090118671A TW90118671A TWI244495B TW I244495 B TWI244495 B TW I244495B TW 090118671 A TW090118671 A TW 090118671A TW 90118671 A TW90118671 A TW 90118671A TW I244495 B TWI244495 B TW I244495B
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- Prior art keywords
- alkyl
- group
- substituted
- unsubstituted
- radical
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- 238000000576 coating method Methods 0.000 title claims abstract description 77
- 238000000034 method Methods 0.000 title claims abstract description 76
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims description 23
- 230000008569 process Effects 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 227
- -1 anthracyl Chemical group 0.000 claims abstract description 172
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 72
- 239000001257 hydrogen Substances 0.000 claims abstract description 72
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 55
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 15
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 8
- 125000005561 phenanthryl group Chemical group 0.000 claims abstract description 4
- 150000003254 radicals Chemical class 0.000 claims description 158
- 239000000126 substance Substances 0.000 claims description 149
- 239000000203 mixture Substances 0.000 claims description 136
- 125000003118 aryl group Chemical group 0.000 claims description 122
- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 239000011248 coating agent Substances 0.000 claims description 55
- 239000003999 initiator Substances 0.000 claims description 40
- 238000009472 formulation Methods 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 27
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- 239000011347 resin Substances 0.000 claims description 26
- 239000000843 powder Substances 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 21
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
- 239000007858 starting material Substances 0.000 claims description 20
- 239000000654 additive Substances 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
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- 229920000877 Melamine resin Polymers 0.000 claims description 15
- 239000002585 base Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000004450 alkenylene group Chemical group 0.000 claims description 13
- 125000004419 alkynylene group Chemical group 0.000 claims description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 239000000049 pigment Substances 0.000 claims description 13
- 239000005977 Ethylene Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000000853 adhesive Substances 0.000 claims description 11
- 230000001070 adhesive effect Effects 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 229920005862 polyol Polymers 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 9
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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- 239000005056 polyisocyanate Substances 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 5
- 239000012965 benzophenone Substances 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
- 239000003504 photosensitizing agent Substances 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
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- 238000006467 substitution reaction Methods 0.000 claims description 4
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- 229930006711 bornane-2,3-dione Natural products 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
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- 150000002976 peresters Chemical class 0.000 claims description 3
- 229920000582 polyisocyanurate Polymers 0.000 claims description 3
- 239000011495 polyisocyanurate Substances 0.000 claims description 3
- 230000003678 scratch resistant effect Effects 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 239000002966 varnish Substances 0.000 claims description 3
- 239000000080 wetting agent Substances 0.000 claims description 3
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 claims description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 2
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims description 2
- 150000008062 acetophenones Chemical class 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
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- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical class [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- 239000003381 stabilizer Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 claims 1
- FXKQPQOOZSXQAG-UHFFFAOYSA-N 4-methyltriazine Chemical class CC1=CC=NN=N1 FXKQPQOOZSXQAG-UHFFFAOYSA-N 0.000 claims 1
- 241000234282 Allium Species 0.000 claims 1
- 101150001915 CHI3 gene Proteins 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 101100497572 Pisum sativum CVCA gene Proteins 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical class CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims 1
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 39
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- 239000010457 zeolite Substances 0.000 description 1
- HASDHSVWTCCGIM-UHFFFAOYSA-N zinc iron(2+) oxygen(2-) Chemical compound [O-2].[O-2].[Fe+2].[Zn+2] HASDHSVWTCCGIM-UHFFFAOYSA-N 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- PKJOUIVGCFHFTK-UHFFFAOYSA-L zinc;hexanoate Chemical compound [Zn+2].CCCCCC([O-])=O.CCCCCC([O-])=O PKJOUIVGCFHFTK-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- 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
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Silicon Polymers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00810720 | 2000-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI244495B true TWI244495B (en) | 2005-12-01 |
Family
ID=8174856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090118671A TWI244495B (en) | 2000-08-14 | 2001-07-31 | Process for producing coatings siloxane photoinitiators |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7279200B2 (enExample) |
| EP (1) | EP1311627B1 (enExample) |
| JP (1) | JP5068413B2 (enExample) |
| KR (1) | KR100818643B1 (enExample) |
| CN (1) | CN1211439C (enExample) |
| AT (1) | ATE360666T1 (enExample) |
| AU (1) | AU2001293732A1 (enExample) |
| BR (1) | BR0113233B1 (enExample) |
| CA (1) | CA2417112A1 (enExample) |
| DE (1) | DE60128105T8 (enExample) |
| MX (1) | MXPA03001383A (enExample) |
| TW (1) | TWI244495B (enExample) |
| WO (1) | WO2002014439A2 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10022352A1 (de) * | 2000-05-08 | 2001-11-22 | Georg Gros | Verfahren zur Beschichtung von elektrolytisch- oder feuerverzinkten Blechen |
| US20030185990A1 (en) * | 2000-09-25 | 2003-10-02 | Klaus Bittner | Method for pretreating and coating metal surfaces prior to forming, with a paint-like coating and use of substrates so coated |
| ATE402195T1 (de) | 2002-02-04 | 2008-08-15 | Ciba Holding Inc | Oberflächenaktive siloxanphotoinitiatoren |
| CA2471810A1 (en) * | 2002-02-04 | 2003-08-14 | Ciba Speciality Chemicals Holding Inc. | Fluorinated photoinitiators in highly fluorinated monomers |
| EP1481074B1 (en) | 2002-03-06 | 2010-10-06 | Basf Se | Enzymatic process for preparing organosilicon group containing photoinitiators |
| CA2483004A1 (en) * | 2002-04-26 | 2003-11-06 | Ciba Specialty Chemicals Holding Inc. | Incorporable photoinitiator |
| US20040115363A1 (en) * | 2002-12-13 | 2004-06-17 | Desai Umesh C. | Sealant and sound dampening composition |
| CN100432122C (zh) * | 2003-06-06 | 2008-11-12 | 西巴特殊化学品控股有限公司 | 新颖的表面活性聚硅氧烷光引发剂 |
| AU2004321917B2 (en) * | 2004-07-27 | 2011-08-25 | Duluxgroup (Australia) Pty Ltd | System for providing powder coated reconstituted cellulosic substrate |
| EP1803553B1 (en) * | 2004-10-22 | 2012-08-01 | Mitsubishi Rayon Co., Ltd. | Matt acrylic resin film product for thermoforming, process for producing the same, and laminated product comprising the same |
| US20060234026A1 (en) * | 2005-04-18 | 2006-10-19 | Huusken Robert W M | Non-combustible high pressure laminate |
| US7919222B2 (en) * | 2006-01-29 | 2011-04-05 | Rohm And Haas Electronics Materials Llc | Coating compositions for use with an overcoated photoresist |
| US20100022676A1 (en) * | 2006-10-03 | 2010-01-28 | Jonathan Rogers | Photocurable compositions comprising a photoinitiator of the phenylglyoxylate type |
| US8680176B2 (en) * | 2007-03-21 | 2014-03-25 | The University Of Southern Mississippi | Nanoencapsulation of isocyanates via aqueous media |
| WO2010126618A1 (en) * | 2009-04-30 | 2010-11-04 | Armstrong World Industries, Inc. | Uvv curable coating compositions and method for coating flooring and other substrates with same |
| CN101880482B (zh) * | 2010-07-12 | 2012-10-24 | 重庆大学 | 一种偶合接枝改性纳米金属氧化物的方法 |
| DE102014107518A1 (de) * | 2014-05-28 | 2015-12-03 | Heraeus Kulzer Gmbh | Reaktiver Mikro-Applikator mit Metall enthaltenden Additiven zur Verwendung mit dental Adhäsiven |
| US10350823B2 (en) | 2015-12-22 | 2019-07-16 | Carbon, Inc. | Dual precursor resin systems for additive manufacturing with dual cure resins |
| JP6531729B2 (ja) * | 2016-07-19 | 2019-06-19 | 株式会社Sumco | シリコン試料の炭素濃度評価方法、シリコンウェーハ製造工程の評価方法、シリコンウェーハの製造方法およびシリコン単結晶インゴットの製造方法 |
| CN213006569U (zh) | 2017-06-21 | 2021-04-20 | 卡本有限公司 | 用于增材制造的系统和对分配用于增材制造的树脂有用的分配系统 |
| US11793289B2 (en) | 2018-03-08 | 2023-10-24 | Applied Lacquer Industries Inc. | Artificial nail tip and curing composition set and applying method thereof |
| US11304492B2 (en) * | 2018-03-08 | 2022-04-19 | Applied Lacquer Industries Inc. | Artificial nail tip and curing composition set and applying method thereof |
| CN113583539B (zh) * | 2021-08-11 | 2022-05-10 | 武汉工程大学 | 一种光学树脂组合物及其制备方法和应用 |
| CN114409902B (zh) * | 2021-12-27 | 2023-04-25 | 北京化工大学 | 多功能型pdms基预聚体、基于该预聚体的膜及其制备 |
| EP4491688A4 (en) * | 2022-03-07 | 2025-07-09 | Lg Chemical Ltd | COMPOUND |
| JP7722248B2 (ja) | 2022-04-22 | 2025-08-13 | 信越化学工業株式会社 | 光反応性オルガノポリシロキサン、その製造方法および光硬化性組成物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3991416A (en) | 1975-09-18 | 1976-11-09 | Hughes Aircraft Company | AC biased and resonated liquid crystal display |
| US4038164A (en) * | 1975-09-18 | 1977-07-26 | Stauffer Chemical Company | Photopolymerizable aryl and heterocyclic glyoxylate compositions and process |
| DK0956280T3 (da) * | 1997-01-30 | 2003-02-24 | Ciba Sc Holding Ag | Ikke-flygtige phenylglyoxylsyreestere |
| TW557298B (en) * | 2000-08-14 | 2003-10-11 | Ciba Sc Holding Ag | A compound, a photopolymerizible composition, a process for producing coatings and a method for causing a photoinitiator to accumulate at the surface of coatings |
-
2001
- 2001-07-31 TW TW090118671A patent/TWI244495B/zh not_active IP Right Cessation
- 2001-08-07 EP EP01974127A patent/EP1311627B1/en not_active Expired - Lifetime
- 2001-08-07 AT AT01974127T patent/ATE360666T1/de not_active IP Right Cessation
- 2001-08-07 KR KR1020037002201A patent/KR100818643B1/ko not_active Expired - Fee Related
- 2001-08-07 WO PCT/EP2001/009123 patent/WO2002014439A2/en not_active Ceased
- 2001-08-07 CN CNB018141595A patent/CN1211439C/zh not_active Expired - Lifetime
- 2001-08-07 MX MXPA03001383A patent/MXPA03001383A/es active IP Right Grant
- 2001-08-07 DE DE60128105T patent/DE60128105T8/de active Active
- 2001-08-07 CA CA002417112A patent/CA2417112A1/en not_active Abandoned
- 2001-08-07 JP JP2002519570A patent/JP5068413B2/ja not_active Expired - Lifetime
- 2001-08-07 BR BRPI0113233-4B1A patent/BR0113233B1/pt not_active IP Right Cessation
- 2001-08-07 US US10/343,620 patent/US7279200B2/en not_active Expired - Lifetime
- 2001-08-07 AU AU2001293732A patent/AU2001293732A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR100818643B1 (ko) | 2008-04-04 |
| EP1311627A2 (en) | 2003-05-21 |
| CN1211439C (zh) | 2005-07-20 |
| WO2002014439A3 (en) | 2002-06-13 |
| US7279200B2 (en) | 2007-10-09 |
| AU2001293732A1 (en) | 2002-02-25 |
| JP5068413B2 (ja) | 2012-11-07 |
| EP1311627B1 (en) | 2007-04-25 |
| US20030213931A1 (en) | 2003-11-20 |
| CN1447844A (zh) | 2003-10-08 |
| BR0113233A (pt) | 2003-06-24 |
| BR0113233B1 (pt) | 2013-10-01 |
| WO2002014439A2 (en) | 2002-02-21 |
| CA2417112A1 (en) | 2002-02-21 |
| KR20030055249A (ko) | 2003-07-02 |
| JP2004506776A (ja) | 2004-03-04 |
| DE60128105D1 (de) | 2007-06-06 |
| ATE360666T1 (de) | 2007-05-15 |
| DE60128105T8 (de) | 2008-04-30 |
| MXPA03001383A (es) | 2003-06-06 |
| DE60128105T2 (de) | 2007-12-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |