DE19639313B4 - Photohärtbare Epoxysilicone, die Fluoreszenz- oder photosensibilisierende Markierungsfarbstoffe als funktionelle Gruppen aufweisen - Google Patents
Photohärtbare Epoxysilicone, die Fluoreszenz- oder photosensibilisierende Markierungsfarbstoffe als funktionelle Gruppen aufweisen Download PDFInfo
- Publication number
- DE19639313B4 DE19639313B4 DE19639313A DE19639313A DE19639313B4 DE 19639313 B4 DE19639313 B4 DE 19639313B4 DE 19639313 A DE19639313 A DE 19639313A DE 19639313 A DE19639313 A DE 19639313A DE 19639313 B4 DE19639313 B4 DE 19639313B4
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- carbon atoms
- monovalent
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- hydrocarbon radicals
- formula
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- Expired - Fee Related
Links
- 125000000524 functional group Chemical group 0.000 title claims abstract description 28
- 239000003504 photosensitizing agent Substances 0.000 title claims description 19
- 230000002165 photosensitisation Effects 0.000 title claims description 18
- 239000000975 dye Substances 0.000 title description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 48
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 36
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 36
- 239000004593 Epoxy Substances 0.000 claims abstract description 22
- 125000001033 ether group Chemical group 0.000 claims abstract description 10
- 229910004298 SiO 2 Inorganic materials 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000011941 photocatalyst Substances 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000003700 epoxy group Chemical group 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000001295 dansyl group Chemical group [H]C1=C([H])C(N(C([H])([H])[H])C([H])([H])[H])=C2C([H])=C([H])C([H])=C(C2=C1[H])S(*)(=O)=O 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 7
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- 238000000576 coating method Methods 0.000 description 40
- 239000011248 coating agent Substances 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- -1 hydrocarbon radicals Chemical class 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 15
- 229920005573 silicon-containing polymer Polymers 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- CCFAKBRKTKVJPO-UHFFFAOYSA-N 1-anthroic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=CC=CC3=CC2=C1 CCFAKBRKTKVJPO-UHFFFAOYSA-N 0.000 description 13
- 239000007850 fluorescent dye Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 238000000016 photochemical curing Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- BBEQQKBWUHCIOU-UHFFFAOYSA-N 5-(dimethylamino)-1-naphthalenesulfonic acid(dansyl acid) Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(O)(=O)=O BBEQQKBWUHCIOU-UHFFFAOYSA-N 0.000 description 5
- 206010034972 Photosensitivity reaction Diseases 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- XGWFJBFNAQHLEF-UHFFFAOYSA-N 9-anthroic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=CC2=C1 XGWFJBFNAQHLEF-UHFFFAOYSA-N 0.000 description 4
- 206010070834 Sensitisation Diseases 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 238000002372 labelling Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 230000008313 sensitization Effects 0.000 description 4
- 239000004447 silicone coating Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000011086 glassine Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000006459 hydrosilylation reaction Methods 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 238000012417 linear regression Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000004876 x-ray fluorescence Methods 0.000 description 3
- ACMLKANOGIVEPB-UHFFFAOYSA-N 2-oxo-2H-chromene-3-carboxylic acid Chemical compound C1=CC=C2OC(=O)C(C(=O)O)=CC2=C1 ACMLKANOGIVEPB-UHFFFAOYSA-N 0.000 description 2
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000012952 cationic photoinitiator Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000001917 fluorescence detection Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 230000001699 photocatalysis Effects 0.000 description 2
- 238000007146 photocatalysis Methods 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- SFWMEKYIRKVEBC-UHFFFAOYSA-N 2-anthracen-9-ylacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=C(C=CC=C3)C3=CC2=C1 SFWMEKYIRKVEBC-UHFFFAOYSA-N 0.000 description 1
- MJKVTPMWOKAVMS-UHFFFAOYSA-N 3-hydroxy-1-benzopyran-2-one Chemical class C1=CC=C2OC(=O)C(O)=CC2=C1 MJKVTPMWOKAVMS-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XPDXVDYUQZHFPV-UHFFFAOYSA-N Dansyl Chloride Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(Cl)(=O)=O XPDXVDYUQZHFPV-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229920001577 copolymer Chemical group 0.000 description 1
- 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 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000005520 diaryliodonium group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000001227 electron beam curing Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000001215 fluorescent labelling Methods 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009681 x-ray fluorescence measurement Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/392—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing sulfur
-
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Silicon Polymers (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US536867 | 1995-09-29 | ||
| US08/536,867 US5583195A (en) | 1995-09-29 | 1995-09-29 | Photocurable epoxy silicones functionalized with fluorescent or photosensitizing marker dyes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE19639313A1 DE19639313A1 (de) | 1997-04-03 |
| DE19639313B4 true DE19639313B4 (de) | 2007-08-16 |
Family
ID=24140246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19639313A Expired - Fee Related DE19639313B4 (de) | 1995-09-29 | 1996-09-25 | Photohärtbare Epoxysilicone, die Fluoreszenz- oder photosensibilisierende Markierungsfarbstoffe als funktionelle Gruppen aufweisen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US5583195A (https=) |
| JP (1) | JPH09183853A (https=) |
| DE (1) | DE19639313B4 (https=) |
| FR (1) | FR2739385B1 (https=) |
| GB (1) | GB2305671B (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5998099A (en) * | 1996-03-08 | 1999-12-07 | Lucent Technologies Inc. | Energy-sensitive resist material and a process for device fabrication using an energy-sensitive resist material |
| US6071585A (en) * | 1998-06-30 | 2000-06-06 | Ncr Corporation | Printable sheet with removable label and method for producing same |
| US6232362B1 (en) * | 1999-05-04 | 2001-05-15 | General Electric Company | Self-sensitized epoxysilicones curable by ultraviolet light and method of synthesis therefor |
| US6824879B2 (en) | 1999-06-10 | 2004-11-30 | Honeywell International Inc. | Spin-on-glass anti-reflective coatings for photolithography |
| US6268457B1 (en) | 1999-06-10 | 2001-07-31 | Allied Signal, Inc. | Spin-on glass anti-reflective coatings for photolithography |
| EP1190277B1 (en) * | 1999-06-10 | 2009-10-07 | AlliedSignal Inc. | Semiconductor having spin-on-glass anti-reflective coatings for photolithography |
| EP1099737A1 (en) * | 1999-11-12 | 2001-05-16 | General Electric Company | Radiation curable silicone composition |
| US6368400B1 (en) * | 2000-07-17 | 2002-04-09 | Honeywell International | Absorbing compounds for spin-on-glass anti-reflective coatings for photolithography |
| RU2196149C2 (ru) * | 2001-03-30 | 2003-01-10 | Кемеровский государственный университет | Способ отверждения высокомолекулярного полидиметилсилоксанового каучука |
| KR20040075866A (ko) | 2001-11-15 | 2004-08-30 | 허니웰 인터내셔날 인코포레이티드 | 포토리소그래피용 스핀-온 무반사 코팅 |
| JP3874108B2 (ja) * | 2002-08-13 | 2007-01-31 | 信越化学工業株式会社 | エポキシ樹脂組成物 |
| RU2229485C1 (ru) * | 2002-11-10 | 2004-05-27 | Кемеровский государственный университет | Способ получения композиционного материала |
| US8053159B2 (en) | 2003-11-18 | 2011-11-08 | Honeywell International Inc. | Antireflective coatings for via fill and photolithography applications and methods of preparation thereof |
| US7517929B2 (en) * | 2004-12-03 | 2009-04-14 | Momentive Performance Materials Inc. | Star-branched silicone polymers as anti-mist additives for coating applications |
| US8198389B2 (en) * | 2006-05-25 | 2012-06-12 | The University Of Akron | Mold release compounds using cycloaliphatic epoxide functionalized polydimethylsiloxane coatings and photo-initiated polymerization |
| US8642246B2 (en) | 2007-02-26 | 2014-02-04 | Honeywell International Inc. | Compositions, coatings and films for tri-layer patterning applications and methods of preparation thereof |
| US8557877B2 (en) | 2009-06-10 | 2013-10-15 | Honeywell International Inc. | Anti-reflective coatings for optically transparent substrates |
| US8864898B2 (en) | 2011-05-31 | 2014-10-21 | Honeywell International Inc. | Coating formulations for optical elements |
| CN105295050B (zh) * | 2014-06-20 | 2017-11-21 | 北京化工大学 | 一类含硅氧链三芳基硫鎓盐及其在光固化环氧树脂中应用 |
| JP6803842B2 (ja) | 2015-04-13 | 2020-12-23 | ハネウェル・インターナショナル・インコーポレーテッドＨｏｎｅｙｗｅｌｌ Ｉｎｔｅｒｎａｔｉｏｎａｌ Ｉｎｃ． | オプトエレクトロニクス用途のためのポリシロキサン製剤及びコーティング |
| US11397185B2 (en) | 2016-11-11 | 2022-07-26 | National Institute Of Advanced Industrial Science And Technology | Method for analyzing protein-containing sample |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE68912024T2 (de) * | 1988-07-29 | 1994-06-16 | Gen Electric | Polysiloxan-Trennmittel-Überzugsmischungen. |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2950986A (en) * | 1957-08-22 | 1960-08-30 | Union Carbide Corp | Ultraviolet light absorbing compositions |
| US3427273A (en) * | 1964-08-10 | 1969-02-11 | Owens Illinois Inc | Process for making luminescent organopolysiloxanes and compositions thereof |
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-
1995
- 1995-09-29 US US08/536,867 patent/US5583195A/en not_active Expired - Lifetime
-
1996
- 1996-09-19 JP JP8246766A patent/JPH09183853A/ja active Pending
- 1996-09-20 FR FR9611472A patent/FR2739385B1/fr not_active Expired - Fee Related
- 1996-09-25 DE DE19639313A patent/DE19639313B4/de not_active Expired - Fee Related
- 1996-09-25 GB GB9619996A patent/GB2305671B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE68912024T2 (de) * | 1988-07-29 | 1994-06-16 | Gen Electric | Polysiloxan-Trennmittel-Überzugsmischungen. |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19639313A1 (de) | 1997-04-03 |
| GB2305671A (en) | 1997-04-16 |
| US5583195A (en) | 1996-12-10 |
| FR2739385A1 (fr) | 1997-04-04 |
| GB2305671B (en) | 1999-05-26 |
| FR2739385B1 (fr) | 2004-04-30 |
| JPH09183853A (ja) | 1997-07-15 |
| GB9619996D0 (en) | 1996-11-13 |
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