CA2417112A1 - Process for producing coatings using surface-active photoinitiators - Google Patents
Process for producing coatings using surface-active photoinitiators Download PDFInfo
- Publication number
- CA2417112A1 CA2417112A1 CA002417112A CA2417112A CA2417112A1 CA 2417112 A1 CA2417112 A1 CA 2417112A1 CA 002417112 A CA002417112 A CA 002417112A CA 2417112 A CA2417112 A CA 2417112A CA 2417112 A1 CA2417112 A1 CA 2417112A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- radical
- phenyl
- unsubstituted
- substituted
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 85
- 238000000576 coating method Methods 0.000 title claims abstract description 63
- 230000008569 process Effects 0.000 title claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 223
- -1 anthracyl Chemical group 0.000 claims abstract description 167
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 22
- 125000005561 phenanthryl group Chemical group 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 167
- 239000000203 mixture Substances 0.000 claims description 137
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 77
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 55
- 238000009472 formulation Methods 0.000 claims description 38
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- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
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- 238000002360 preparation method Methods 0.000 description 23
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- 239000003999 initiator Substances 0.000 description 20
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 13
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- 150000001412 amines Chemical class 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
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- 239000000178 monomer Substances 0.000 description 12
- 239000000049 pigment Substances 0.000 description 12
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- 150000002148 esters Chemical class 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 229910008338 Si—(CH3) Inorganic materials 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 10
- HVGMRWPZNYUBPC-UHFFFAOYSA-N oxaldehydic acid;2-oxo-2-phenylacetic acid Chemical compound OC(=O)C=O.OC(=O)C(=O)C1=CC=CC=C1 HVGMRWPZNYUBPC-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
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- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 description 9
- 229920000570 polyether Polymers 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 7
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- 239000004593 Epoxy Substances 0.000 description 7
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 6
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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- 125000005474 octanoate group Chemical group 0.000 description 1
- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000001022 rhodamine dye Substances 0.000 description 1
- 102220042509 rs112033303 Human genes 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- ORIHZIZPTZTNCU-YVMONPNESA-N salicylaldoxime Chemical compound O\N=C/C1=CC=CC=C1O ORIHZIZPTZTNCU-YVMONPNESA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
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- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
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- 239000002344 surface layer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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- 150000001911 terphenyls Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
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- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000002469 tricosyl 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])C([H])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00810720.3 | 2000-08-14 | ||
| EP00810720 | 2000-08-14 | ||
| PCT/EP2001/009123 WO2002014439A2 (en) | 2000-08-14 | 2001-08-07 | Process for producing coatings using surface-active photoinitiators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2417112A1 true CA2417112A1 (en) | 2002-02-21 |
Family
ID=8174856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002417112A Abandoned CA2417112A1 (en) | 2000-08-14 | 2001-08-07 | Process for producing coatings using surface-active photoinitiators |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7279200B2 (https=) |
| EP (1) | EP1311627B1 (https=) |
| JP (1) | JP5068413B2 (https=) |
| KR (1) | KR100818643B1 (https=) |
| CN (1) | CN1211439C (https=) |
| AT (1) | ATE360666T1 (https=) |
| AU (1) | AU2001293732A1 (https=) |
| BR (1) | BR0113233B1 (https=) |
| CA (1) | CA2417112A1 (https=) |
| DE (1) | DE60128105T8 (https=) |
| MX (1) | MXPA03001383A (https=) |
| TW (1) | TWI244495B (https=) |
| WO (1) | WO2002014439A2 (https=) |
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 |
| WO2002024344A2 (de) * | 2000-09-25 | 2002-03-28 | Chemetall Gmbh | Verfahren zur vorbehandlung und beschichtung von metallischen oberflächen vor der umformung mit einem lackähnlichen überzug und verwendung der derart beschichteten substrate |
| WO2003066693A1 (en) * | 2002-02-04 | 2003-08-14 | Ciba Specialty Chemicals Holding Inc. | Fluorinated photoinitiators in highly fluorinated monomers |
| EP1472292B1 (en) | 2002-02-04 | 2008-07-23 | Ciba Holding Inc. | Surface-active siloxane photoinitiators |
| MXPA04007993A (es) * | 2002-03-06 | 2004-11-26 | Ciba Sc Holding Ag | Proceso enzimatico para la preparacion de fotoiniciadores que contienen grupos de silicio organicos. |
| CN1307207C (zh) * | 2002-04-26 | 2007-03-28 | 西巴特殊化学品控股有限公司 | 可引入的光敏引发剂 |
| US20040115363A1 (en) * | 2002-12-13 | 2004-06-17 | Desai Umesh C. | Sealant and sound dampening composition |
| JP4767840B2 (ja) * | 2003-06-06 | 2011-09-07 | チバ ホールディング インコーポレーテッド | 新規な界面活性ポリシロキサン光開始剤 |
| EP1781750A4 (en) * | 2004-07-27 | 2012-08-08 | Duluxgroup Australia Pty Ltd | SYSTEM FOR PROVIDING A POWDER-COATED WOOD MATERIAL |
| US20080038544A1 (en) * | 2004-10-22 | 2008-02-14 | Mitsubishi Rayon Co., Ltd. | Matt Acrylic Resin Filmy Product For Thermoforming, Process For Production Thereof, and Laminates Comprising the Product |
| 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 |
| US20100276059A1 (en) * | 2009-04-30 | 2010-11-04 | Dong Tian | 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 |
| WO2017112653A1 (en) * | 2015-12-22 | 2017-06-29 | 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 |
|---|---|---|---|---|
| US4038164A (en) * | 1975-09-18 | 1977-07-26 | Stauffer Chemical Company | Photopolymerizable aryl and heterocyclic glyoxylate compositions and process |
| US3991416A (en) * | 1975-09-18 | 1976-11-09 | Hughes Aircraft Company | AC biased and resonated liquid crystal display |
| EP0956280B1 (en) * | 1997-01-30 | 2002-10-30 | Ciba SC Holding AG | Non-volatile phenylglyoxalic esters |
| 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 CN CNB018141595A patent/CN1211439C/zh not_active Expired - Lifetime
- 2001-08-07 DE DE60128105T patent/DE60128105T8/de active Active
- 2001-08-07 WO PCT/EP2001/009123 patent/WO2002014439A2/en not_active Ceased
- 2001-08-07 US US10/343,620 patent/US7279200B2/en not_active Expired - Lifetime
- 2001-08-07 MX MXPA03001383A patent/MXPA03001383A/es active IP Right Grant
- 2001-08-07 CA CA002417112A patent/CA2417112A1/en not_active Abandoned
- 2001-08-07 AU AU2001293732A patent/AU2001293732A1/en not_active Abandoned
- 2001-08-07 JP JP2002519570A patent/JP5068413B2/ja not_active Expired - Lifetime
- 2001-08-07 AT AT01974127T patent/ATE360666T1/de not_active IP Right Cessation
- 2001-08-07 BR BRPI0113233-4B1A patent/BR0113233B1/pt not_active IP Right Cessation
- 2001-08-07 KR KR1020037002201A patent/KR100818643B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE60128105T8 (de) | 2008-04-30 |
| JP2004506776A (ja) | 2004-03-04 |
| EP1311627A2 (en) | 2003-05-21 |
| US20030213931A1 (en) | 2003-11-20 |
| US7279200B2 (en) | 2007-10-09 |
| AU2001293732A1 (en) | 2002-02-25 |
| BR0113233A (pt) | 2003-06-24 |
| DE60128105T2 (de) | 2007-12-27 |
| TWI244495B (en) | 2005-12-01 |
| BR0113233B1 (pt) | 2013-10-01 |
| CN1211439C (zh) | 2005-07-20 |
| KR20030055249A (ko) | 2003-07-02 |
| DE60128105D1 (de) | 2007-06-06 |
| EP1311627B1 (en) | 2007-04-25 |
| ATE360666T1 (de) | 2007-05-15 |
| MXPA03001383A (es) | 2003-06-06 |
| WO2002014439A3 (en) | 2002-06-13 |
| JP5068413B2 (ja) | 2012-11-07 |
| KR100818643B1 (ko) | 2008-04-04 |
| WO2002014439A2 (en) | 2002-02-21 |
| CN1447844A (zh) | 2003-10-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |