DE1795089C3 - Photopolymerisierbares Material - Google Patents
Photopolymerisierbares MaterialInfo
- Publication number
- DE1795089C3 DE1795089C3 DE1795089A DE1795089A DE1795089C3 DE 1795089 C3 DE1795089 C3 DE 1795089C3 DE 1795089 A DE1795089 A DE 1795089A DE 1795089 A DE1795089 A DE 1795089A DE 1795089 C3 DE1795089 C3 DE 1795089C3
- Authority
- DE
- Germany
- Prior art keywords
- oxime ester
- polymer
- oxime
- polymerization
- photopolymerizable
- 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.)
- Expired
Links
- 239000000463 material Substances 0.000 title claims description 24
- 239000003999 initiator Substances 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 description 36
- -1 nitrogen-containing compound Chemical class 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 150000002894 organic compounds Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- ZMTNJQODYNOQRD-UHFFFAOYSA-N (3-oxobutan-2-ylideneamino) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)ON=C(C)C(C)=O ZMTNJQODYNOQRD-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical class ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229920000578 graft copolymer Polymers 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- DAXHBZRJXBWLQA-UHFFFAOYSA-N 2-hydroxyimino-2-(4-hydroxyphenyl)acetaldehyde Chemical compound ON=C(C=O)c1ccc(O)cc1 DAXHBZRJXBWLQA-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- FSEUPUDHEBLWJY-HWKANZROSA-N diacetylmonoxime Chemical compound CC(=O)C(\C)=N\O FSEUPUDHEBLWJY-HWKANZROSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 3
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 description 2
- NDVAMUMVOJRAJV-UHFFFAOYSA-N 10h-phenanthren-9-one Chemical group C1=CC=C2C(=O)CC3=CC=CC=C3C2=C1 NDVAMUMVOJRAJV-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- AOWKYMSQZFTWNS-UHFFFAOYSA-N 2-hydroxyimino-1-(4-hydroxyphenyl)propan-1-one Chemical compound ON=C(C)C(=O)C1=CC=C(O)C=C1 AOWKYMSQZFTWNS-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical group C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UWIULCYKVGIOPW-UHFFFAOYSA-N Glycolone Natural products CCOC1=C(CC=CC)C(=O)N(C)c2c(O)cccc12 UWIULCYKVGIOPW-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- UQHBXGDYCQUWDB-UHFFFAOYSA-N N(=O)NS(=O)(=O)N Chemical compound N(=O)NS(=O)(=O)N UQHBXGDYCQUWDB-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 description 1
- IQFXJRXOTKFGPN-UHFFFAOYSA-N n-ethenyl-n-ethylethanamine Chemical group CCN(CC)C=C IQFXJRXOTKFGPN-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000005336 safety glass Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- 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
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
-
- 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
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0384—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the main chain of the photopolymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/904—Monomer or polymer contains initiating group
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- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB36394/67A GB1180846A (en) | 1967-08-08 | 1967-08-08 | Photopolymerisation of Ethylenically Unsaturated Organic Compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1795089A1 DE1795089A1 (de) | 1972-01-20 |
| DE1795089B2 DE1795089B2 (de) | 1981-05-21 |
| DE1795089C3 true DE1795089C3 (de) | 1982-03-18 |
Family
ID=10387736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1795089A Expired DE1795089C3 (de) | 1967-08-08 | 1968-08-08 | Photopolymerisierbares Material |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3558309A (oth) |
| BE (1) | BE719039A (oth) |
| DE (1) | DE1795089C3 (oth) |
| FR (1) | FR1576141A (oth) |
| GB (1) | GB1180846A (oth) |
| NL (1) | NL154518B (oth) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3905815A (en) * | 1971-12-17 | 1975-09-16 | Minnesota Mining & Mfg | Photopolymerizable sheet material with diazo resin layer |
| US4202694A (en) * | 1977-04-21 | 1980-05-13 | Polaroid Corporation | Pendant oxime polymers and photographic use thereof |
| FR2393345A1 (fr) * | 1977-06-01 | 1978-12-29 | Agfa Gevaert Nv | Fabrication d'elements modifies sous forme d'images |
| GB2029423A (en) * | 1978-08-25 | 1980-03-19 | Agfa Gevaert Nv | Photo-polymerisable materials and recording method |
| NO150963C (no) * | 1979-01-11 | 1985-01-16 | Scott Bader Co | Polyesterharpiksmateriale som er herdbart ved hjelp av synlig lys, og fremgangsmaate til herding av dette |
| US4282309A (en) * | 1979-01-24 | 1981-08-04 | Agfa-Gevaert, N.V. | Photosensitive composition containing an ethylenically unsaturated compound, initiator and sensitizer |
| JPS5695902A (en) * | 1979-12-29 | 1981-08-03 | Toyobo Co Ltd | Uv-curable resin composition |
| US4539286A (en) * | 1983-06-06 | 1985-09-03 | Dynachem Corporation | Flexible, fast processing, photopolymerizable composition |
| US4610951A (en) * | 1983-06-06 | 1986-09-09 | Dynachem Corporation | Process of using a flexible, fast processing photopolymerizable composition |
| HU196288B (en) * | 1985-06-04 | 1988-11-28 | Egyt Gyogyszervegyeszeti Gyar | Fungicides containing as active substance new derivatives of fenantren and process for production of the active substance |
| US4590145A (en) * | 1985-06-28 | 1986-05-20 | Daicel Chemical Industries, Ltd. | Photopolymerization initiator comprised of thioxanthones and oxime esters |
| US5019482A (en) * | 1987-08-12 | 1991-05-28 | Asahi Kasei Kogyo Kabushiki Kaisha | Polymer/oxime ester/coumarin compound photosensitive composition |
| JP2640470B2 (ja) * | 1987-08-19 | 1997-08-13 | 旭化成工業株式会社 | 新しい感光性組成物 |
| JP3498869B2 (ja) * | 1995-01-30 | 2004-02-23 | 富士写真フイルム株式会社 | 光重合性組成物を有する画像形成材料 |
| DE69703505T2 (de) | 1996-02-26 | 2001-06-13 | Agfa-Gevaert N.V., Mortsel | Bildaufzeichnungselement, das eine Zweiphasenbeschichtung mit einer dispergierten hydrophoben photopolymerisierbaren Phase enthält |
| SG77689A1 (en) * | 1998-06-26 | 2001-01-16 | Ciba Sc Holding Ag | New o-acyloxime photoinitiators |
| KR100591030B1 (ko) | 1999-03-03 | 2006-06-22 | 시바 스페셜티 케미칼스 홀딩 인크. | 옥심 유도체를 포함하는 광중합성 조성물 |
| NL1016815C2 (nl) * | 1999-12-15 | 2002-05-14 | Ciba Sc Holding Ag | Oximester-fotoinitiatoren. |
| SG97168A1 (en) * | 1999-12-15 | 2003-07-18 | Ciba Sc Holding Ag | Photosensitive resin composition |
| US6652970B1 (en) * | 2000-07-07 | 2003-11-25 | 3M Innovative Properties Company | Degradable crosslinkers, compositions therefrom, and methods of their preparation and use |
| KR100417091B1 (ko) * | 2001-05-15 | 2004-02-05 | 주식회사 엘지화학 | 기능성 옥심 에스테르계 화합물 및 이를 포함하는 감광성조성물 |
| KR100801457B1 (ko) * | 2001-06-11 | 2008-02-11 | 시바 스페셜티 케미칼스 홀딩 인크. | 결합된 구조를 가지는 옥심 에스테르 광개시제 |
| KR101032582B1 (ko) * | 2002-12-03 | 2011-05-06 | 시바 홀딩 인크 | 헤테로방향족 그룹을 갖는 옥심 에스테르 광개시제 |
| ATE381540T1 (de) * | 2004-08-18 | 2008-01-15 | Ciba Sc Holding Ag | Oximesther-fotoinitiatoren |
| DE602005019888D1 (de) * | 2004-08-20 | 2010-04-22 | Adeka Corp | Oximesterverbindung und photopolymerisationsinitiator, der eine solche verbindung enthält |
| JP4650211B2 (ja) * | 2005-10-31 | 2011-03-16 | 東洋インキ製造株式会社 | 光重合性組成物 |
| DE602006019788D1 (de) | 2005-12-01 | 2011-03-03 | Basf Se | Oximester-Fotoinitiatoren |
| KR100814232B1 (ko) | 2005-12-01 | 2008-03-17 | 주식회사 엘지화학 | 옥심 에스테르를 포함하는 트리아진계 광활성 화합물을포함하는 착색 감광성 조성물 |
| US8586268B2 (en) * | 2005-12-20 | 2013-11-19 | Basf Se | Oxime ester photoinitiators |
| US8026296B2 (en) * | 2005-12-20 | 2011-09-27 | 3M Innovative Properties Company | Dental compositions including a thermally labile component, and the use thereof |
| KR101075686B1 (ko) * | 2006-01-13 | 2011-10-21 | 토요잉크Sc홀딩스주식회사 | 디케토옥심에스테르화합물 및 그 용도 |
| EP2144900B1 (en) * | 2007-05-11 | 2015-03-18 | Basf Se | Oxime ester photoinitiators |
| CN102702073B (zh) | 2007-05-11 | 2015-06-10 | 巴斯夫欧洲公司 | 肟酯光引发剂 |
| US8349548B2 (en) * | 2007-05-11 | 2013-01-08 | Basf Se | Oxime ester photoinitiators |
| JP5274132B2 (ja) * | 2007-07-17 | 2013-08-28 | 富士フイルム株式会社 | 硬化性組成物、カラーフィルタ用硬化性組成物、パターン形成方法、カラーフィルタ、及びその製造方法 |
| EP2037323B1 (en) * | 2007-07-17 | 2014-12-10 | FUJIFILM Corporation | Photosensitive compositions |
| JP5507054B2 (ja) * | 2008-03-28 | 2014-05-28 | 富士フイルム株式会社 | 重合性組成物、カラーフィルタ、カラーフィルタの製造方法、及び固体撮像素子 |
| CN102112438B (zh) | 2008-06-06 | 2014-07-23 | 巴斯夫欧洲公司 | 肟酯光敏引发剂 |
| JP4344400B1 (ja) * | 2009-02-16 | 2009-10-14 | 株式会社日本化学工業所 | オキシムエステル化合物及びこれらを用いた感光性樹脂組成物 |
| CN101565472B (zh) | 2009-05-19 | 2011-05-04 | 常州强力电子新材料有限公司 | 酮肟酯类光引发剂 |
| KR101678028B1 (ko) | 2009-06-17 | 2016-11-21 | 토요잉크Sc홀딩스주식회사 | 옥심에스테르 화합물, 라디칼 중합개시제, 중합성 조성물, 네가티브형 레지스트 및 화상 패턴 |
| US8816211B2 (en) | 2011-02-14 | 2014-08-26 | Eastman Kodak Company | Articles with photocurable and photocured compositions |
| US20120207935A1 (en) | 2011-02-14 | 2012-08-16 | Deepak Shukla | Photocurable inks and methods of use |
| US20120208914A1 (en) | 2011-02-14 | 2012-08-16 | Deepak Shukla | Photoinitiator compositions and uses |
| CA2836817C (en) | 2011-05-25 | 2016-08-02 | American Dye Source Inc. | Compounds with oxime ester and/or acyl groups |
| KR101985054B1 (ko) * | 2013-09-02 | 2019-05-31 | 인사이트 하이 테크놀로지 씨오., 엘티디. | 시클로펜탄디온 옥심 에스테르 및 그 응용 |
| CN104910053B (zh) * | 2014-06-09 | 2017-09-12 | 北京英力科技发展有限公司 | 不对称二肟酯化合物及其制造方法与应用 |
| WO2016082304A1 (zh) * | 2014-11-28 | 2016-06-02 | 北京英力科技发展有限公司 | 一种光固化阻焊油墨 |
| US11041037B2 (en) | 2018-10-01 | 2021-06-22 | Solenis Technologies, L.P. | Ultra violet assisted photo initiated free radical polymerization |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE465271A (oth) * | 1941-12-31 | 1900-01-01 | ||
| DE1099166B (de) * | 1959-12-01 | 1961-02-09 | Basf Ag | Sensibilisatoren zur Photopolymerisation ungesaettigter organischer Verbindungen |
-
1967
- 1967-08-08 GB GB36394/67A patent/GB1180846A/en not_active Expired
-
1968
- 1968-07-11 US US743948A patent/US3558309A/en not_active Expired - Lifetime
- 1968-08-05 BE BE719039D patent/BE719039A/xx not_active IP Right Cessation
- 1968-08-05 FR FR1576141D patent/FR1576141A/fr not_active Expired
- 1968-08-08 NL NL686811281A patent/NL154518B/xx not_active IP Right Cessation
- 1968-08-08 DE DE1795089A patent/DE1795089C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1180846A (en) | 1970-02-11 |
| DE1795089A1 (de) | 1972-01-20 |
| NL154518B (nl) | 1977-09-15 |
| US3558309A (en) | 1971-01-26 |
| FR1576141A (oth) | 1969-07-25 |
| BE719039A (oth) | 1969-02-05 |
| NL6811281A (oth) | 1969-01-27 |
| DE1795089B2 (de) | 1981-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |