Source: http://www.google.com/patents/US5190845?dq=5,987,610
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Patent US5190845 - Photosensitive resin composition and color filter comprising a polymer ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsA photosensitive resin composition comprising: (a) a polymer dyeable with an anionic dye (b) an azide photosensitive compound, and (c) a compound having at least two acryloyl and/or methacryloyl groups in the same molecule thereof, and a color filter obtained by using the resin composition....http://www.google.com/patents/US5190845?utm_source=gb-gplus-sharePatent US5190845 - Photosensitive resin composition and color filter comprising a polymer dyeable with an anionic dye, an azide compound and a compound with at least two acrylol groupsAdvanced Patent SearchPublication numberUS5190845 APublication typeGrantApplication numberUS 07/345,543PCT numberPCT/JP1988/000700Publication dateMar 2, 1993Filing dateJul 14, 1988Priority dateJul 28, 1987Fee statusLapsedAlso published asDE3852756D1, DE3852756T2, EP0329791A1, EP0329791A4, EP0329791B1, WO1989001186A1Publication number07345543, 345543, PCT/1988/700, PCT/JP/1988/000700, PCT/JP/1988/00700, PCT/JP/88/000700, PCT/JP/88/00700, PCT/JP1988/000700, PCT/JP1988/00700, PCT/JP1988000700, PCT/JP198800700, PCT/JP88/000700, PCT/JP88/00700, PCT/JP88000700, PCT/JP8800700, US 5190845 A, US 5190845A, US-A-5190845, US5190845 A, US5190845AInventorsMatsuo Hashimoto, Nobuyuki Futamura, Sumio Yoda, Yoshifumi SaikiOriginal AssigneeNippon Kayaku Kabushiki KaishaExport CitationBiBTeX, EndNote, RefManPatent Citations (24), Non-Patent Citations (2), Referenced by (63), Classifications (9), Legal Events (4) External Links: USPTO, USPTO Assignment, EspacenetPhotosensitive resin composition and color filter comprising a polymer dyeable with an anionic dye, an azide compound and a compound with at least two acrylol groups
US 5190845 AAbstract
1. A photosensitive resin composition comprising(a) a polymer dyeable with an anionic dye, (b) an azide photosensitive compound, and (c) a compound having at least two acryloyl groups in the same molecule thereof, selected from the group consisting of spiroglycol diacrylate and cyclohexanedimethylol diacrylate. 2. A resin composition according to claim 1, wherein 0.1 to 20 arts of the azide photosensitive compound and 0.1 to 20 parts of the compound having at least two acryloyl groups int eh same molecule thereof are used per 100 parts of the polymer dyeable with an anionic dye.
3. A resin composition according to claim 1 or 2, wherein the azide photosensitive compound is at least one compound selected from the group consisting of4,4'-diazidochalcone, 2,6-bis(4'-azidobenzal)cyclohexanone, 2,6-bis(4'-azidobenzal)- 4-methylcyclohexanone, 1,3-bis(4'-azidobenzal)- 2-propanone, p-azidobenzalacetophenone, p-azidobenzalacetone, 1,3-bis(4'-azidobenzal)- 2-propanone-2'-sulfonic acid, 4,4'-diazidostilbene-2,2'-disulfonic acid, sodium 4,4'-diazidostilbene-2,2'-disulfonate, 1. 3-bis(4'-azido-2'-sulfobenzal)-2-propanone,1,3-bis(4'-azido-2'-sodiumsulfonatobenzal)-2-propanone, 2,6-bis(4'-azido-2'-sulfobenzal)cyclohexanone, 2,6-bis(4'-azido-2'-sulfobenzal)methylcyclohexanone, 2,6-bis(4'-azido-2'-sodiumsulfonatobenzal)methylcyclohexanone, and N,N'-diethyl-2,2'-disulfonamido-4,4'-diazidostilbene. 4. A color filter obtained by using a resin composition according to claim 1 or 2.
6. A resin composition according to claim 1, wherein said polymer dyeable with an anionic dye is a polymer prepared by polymerizing:a. a dyeable monomer; b. a hydrophilic monomer; and c. a hydrophobic monomer. 7. A resin according to claim 6, wherein the dyeable monomer is selected from the group consisting of (N,N-dimethylamino)ethyl acrylate, (N,N-dimethylamino)ethyl methacrylate, (N,N-diethylamino)ethyl acrylate, (N,N-diethylamino)ethyl methacrylate, (N,N-dimethylamino)propyl acrylamide, (N,N-dimethylamino)propyl methacrylamide, (N,N-dimethylamino)ethyl vinyl ether, (N,N-dimethylamino)propyl acrylate, (N,N-dimethylamino)propyl methacrylate, 4-vinylpyridine, 2-hydroxy-3-methacryloyloxypropyltrimethylammonium chloride, and methacryloyloxyethyltrimethylammonium chloride.
The development is preferably carried out in the range from normal temperature to 60� C. (for instance, 10 to 60� C.). The thickness of the resin coating thus developed can be set to an arbitrary value, for instance, 0.2 to 10 μ. The substrate, such as glass and plastic, having a predetermined pattern thus developed is dyed with an anionic dye.
To perform dyeing by use of the dye, 0.01 to 200 parts by weight of the dye is dissolved in 1000 parts by weight of water. The pH of the liquid thus prepared may be in a weak basic to acidic range. Dyeing by use of the dye solution is carried out at a temperature ranging from room temperature to 100� C. It is preferable to carry out dyeing at a high temperature in the range, because a dyed product is thereby obtainable in a short time. After the dyeing, the dyed product is taken out and dried, whereby the substrate with a dyed surface coating (color filter) is obtainable.
______________________________________Dimethylaminopropylacrylamide                31 parts2-Hydroxyethyl methacrylate                14 partsVinylpyrrolidone     15 partsMethyl methacrylate  15 partsMethyl acrylate      13 partsDimethylaminoacrylamide                10 partsDioxane              200 parts&#945;,&#945;'-azobis(isobutyronitrile)                1 part______________________________________
A liquid of the above formulation was brought into polymerization reaction in a nitrogen atmosphere at 80� C. for 5 hours. The polymerization liquid was put into a large amount of isopropyl ether, and after precipitation of a polymeric component, the polymer was taken out and dried. A solution comprising a mixture of 15 parts of the dried polymer with 0.63 part of 4,4'-diazidochalcone, 0.57 part of spiroglycol diacrylate, 88 parts of ethyl cellosolve, 27 parts of diethylene glycol dimethyl ether and 0.6 part of a silane coupling agent KBM 603 (a product by Shinetsu Chemical Co., Ltd.) was used as a dyeable photosensitive resin liquid.
Next, the dyeable photosensitive resin liquid was applied to a glass plate by a spin coating method, and after drying at 80� C for 30 minutes, the dried resin coating was irradiated with UV rays at a surface illuminance of 8 mW/cm2 through a mask having a resolution test pattern for 5 seconds. The UV-irradiated resin coating was developed for 5 minutes by immersion in a developing liquid containing 2 parts of Emulgen 913 (a polyoxyethylene nonylphenylene ether type nonionic surface active agent, produced by Kao Soap Co., Ltd.) in 1000 parts of water at 60� C. under stirring, whereby a glass substrate having a dyeable coating in only the irradiated areas was obtained. The glass plate was subjected further to post-baking at 160� C. for 30 minutes, after which the thickness of the coating was 0.5 μ. The glass plate thus treated was dyed by using a 0.2% aqueous solution of Blue 43P (a dye for color filter, produced by Nippon Kayaku Co., Ltd.) at 60� C. for 10 minutes, to obtain a glass plate dyed pattern-wise in deep blue. The resolving power of the pattern of the glass plate was 5 μ, and both the transparency of the dyed coating and the dimensional stability of the image were satisfactory.
The same operation as in Example 1 was carried out except that 0.63 part of 4,4'-diazidochalcone used in Example 1 was replaced by 0.68 part of sodium 4,4'-diazidostilbene-2,2-disulfonate, 0.57 part of spiroglycol diacrylate used in Example 1 was replaced by 0.67 part of cyclohexanedimethylol diacrylate, and that the 5-minute development in the stirred developing liquid at 60� C carried out in Example 1 was replaced by 1-minute development in the stirred developing liquid at 25� C. The UV irradiation time required for obtaining the same resolving power, transparency of the dyed coating and dimensional stability of the image as those in Example 1 was 5 seconds.
The same operation as in Example 1 was carried out except that 0.63 part of 4,4'-diazidochalcone used in Example 1 was replaced by 0.67 part of 1,3-bis(4'-azidobenzal)-2-propanone-2'-sulfonic acid, 0.57 part of spiroglycol diacrylate used in Example 1 was replaced by 0.67 part of cyclohexanedimethylol diacrylate, and that the 5-minute development in the stirred developing liquid at 60� C. carried out in Example 1 was replaced by 2-minute development in the stirred developing liquid at 25� C. The UV irradiation time required for obtaining the same resolving power, transparency of the dyed coating and dimensional stability of the image as those in Example 1 was 20 seconds.
The same operation as in Example 1 was carried out except that 0.63 part of 4,4'-diazidochalcone used in Example 1 was replaced by 0.15 part of sodium 4,4'-diazidostilbene-2,2'-disulfonate and 0.48 part of 4,4'-diazidochalcone, that 0.57 part of spiroglycol diacrylate used in Example 1 was replaced by 0.67 part of cyclohexanedimethylol diacrylate, and that the 5-minute development in the stirred developing liquid at 60� C. carried out in Example 1 was replaced by 5-minute development in the stirred developing liquid at 40� C. The UV irradiation time required for obtaining the same resolving power, transparency of the dyed coating and dimensional stability of the image as those in Example 1 was 8 seconds.
______________________________________        Example        10      11        12______________________________________Dimethylaminopropyl          30     parts  28   parts                                  31   partsacrylamide2-Hydroxyethyl 18     parts  19   parts                                  17   partsmethacrylateMethyl methacrylate          33     parts  15   parts                                  15   partsMethyl acrylate          0      part   20   parts                                  19   partsVinylpyrrolidone          15     parts  0    part 21   partsDimethylaminoacrylamide          10     parts  20   parts                                  0    partDioxane        210    parts  218  parts                                  220  parts&#945;,&#945;'-azobis          2      parts  1.9  parts                                  2.3  part(isobutyronitrile)Total          318    parts  321.8                             parts                                  325.3                                       parts______________________________________
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