CA1232915A - Photosensitive resin compositions - Google Patents
Photosensitive resin compositionsInfo
- Publication number
- CA1232915A CA1232915A CA000445119A CA445119A CA1232915A CA 1232915 A CA1232915 A CA 1232915A CA 000445119 A CA000445119 A CA 000445119A CA 445119 A CA445119 A CA 445119A CA 1232915 A CA1232915 A CA 1232915A
- Authority
- CA
- Canada
- Prior art keywords
- surfactant
- perfluorooctyl
- fluorocarbon
- photosensitive resin
- mixtures
- 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
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
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Detergent Compositions (AREA)
- Polymerisation Methods In General (AREA)
Abstract
ABSTRACT
A surfactant which reduces contamination in resin based printing plates is combined with the photosensitive resin and eliminates the need to separately pretreat the plates. The surfactant is preferably a nonionic fluorocarbon with four to fourteen perfluoroalkyl groups or mixtures thereof.
Case 2735
A surfactant which reduces contamination in resin based printing plates is combined with the photosensitive resin and eliminates the need to separately pretreat the plates. The surfactant is preferably a nonionic fluorocarbon with four to fourteen perfluoroalkyl groups or mixtures thereof.
Case 2735
Description
~Z~;~9~5 BACKGROUND OF TIIE INVNTION
The present invention relates to a surfactant which whan used in combination with a photosensitive resin composition n a high-speed rotary press printing plate, reduces or prevents contamination. The present invention is particularly useful with a photosensitive resin composition used to make a newspaper printing plate.
In the past, the plates generally used in high-speed rotary presses used by newspapers were metall e.g. lead. In recent years the trend has been away from such conventional metal plates and towards use of resin based plates.
The resin based letterpress plates are such that a photosensitive resin composition is irradiated with an actinic light beam through a negative film to cure the photosensitive resin. Thereafter, a cured resin is developed by various means, thereby forming a letterpress image. The resin based letterpress plates are recognized as having advantages because of the increased ease of handling based on their light weight. Although the resin based plates are easier to work with, they have the disadvantage of becoming contaminated ; (hereinafter referred to as "contamination") in the dotsl especially on the photographic face, in the course of printing. Although the mechanism o this contamination is not fully understood, when this phenomenon occurs ink and paper dust will accumulate in the valley (concave) portions of the relief plate and the quality of the normal dot (photograph) is impaired.
In the past, contamination was prevented by separately treating the resin plates with surface agents which were made by dissolving silicone oil in ~;~ a hydrocarbon solvent or with agents that were water and oil repellent. However, it was found that agents made by dissolving silicone oil in a hydrocarbon solvent were not sufficiently durable because they dissolved easily in the ink.
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As a result, contamination occurred after about 20,000 impressions ~ere made.
Further, the latter type of agent is not effective unlcss conlplete heat-curing is conduc-ted after pre-treating witll the agent. Additionally, even if the agent is heat-cured its durability is not always satisfactory and contamination still occurs aftcr printing about 30,000 impressions.
It is an object of this invention to solve the above problems in resin based letterpress printing plates.
SU~IARY 0~ INVENTION
The p~esent invention prevents or reduces contamination by use of a photosensitive resin composition which includes about 0.001 to about 5% by weight of a fluorocarbon surfactant containing perfluoroalkyl groups ~C4-C14).
The surfactant is preferably nonionic. The resin letterpress plate made from the photosensitive resin composition of the present invention displays a remarkable contamination preventing effect, i.e. an increase in the number of impressions that can be made without evidencing any contamination. Use of the composition of this invention renders quite unnecessary such conventional operations as preliminary surface treatment. By virtue of use of this composition it is possible to subject the above letterpress plate to printing merely by mounting it on a rotary press.
In the present invention the nonionic fluorocarbon surfactant contains perfluoroalkyl groups (C4-C14) and is preferably contained in a photosensitive resin composition in amounts of about 0.001 wt.% to about 5 wt.%. If the content is less than about 0.001 wt.%, its effect becomes poor.
If its content exceeds about 5 wt.% it will still be useful but will be less effective, since its ink repellency becomes too strong with the result that ` ~ the photographic printing effect becomes poor. Additionally, if the content
The present invention relates to a surfactant which whan used in combination with a photosensitive resin composition n a high-speed rotary press printing plate, reduces or prevents contamination. The present invention is particularly useful with a photosensitive resin composition used to make a newspaper printing plate.
In the past, the plates generally used in high-speed rotary presses used by newspapers were metall e.g. lead. In recent years the trend has been away from such conventional metal plates and towards use of resin based plates.
The resin based letterpress plates are such that a photosensitive resin composition is irradiated with an actinic light beam through a negative film to cure the photosensitive resin. Thereafter, a cured resin is developed by various means, thereby forming a letterpress image. The resin based letterpress plates are recognized as having advantages because of the increased ease of handling based on their light weight. Although the resin based plates are easier to work with, they have the disadvantage of becoming contaminated ; (hereinafter referred to as "contamination") in the dotsl especially on the photographic face, in the course of printing. Although the mechanism o this contamination is not fully understood, when this phenomenon occurs ink and paper dust will accumulate in the valley (concave) portions of the relief plate and the quality of the normal dot (photograph) is impaired.
In the past, contamination was prevented by separately treating the resin plates with surface agents which were made by dissolving silicone oil in ~;~ a hydrocarbon solvent or with agents that were water and oil repellent. However, it was found that agents made by dissolving silicone oil in a hydrocarbon solvent were not sufficiently durable because they dissolved easily in the ink.
: ~ ~ , ., ~ ~ Case 2735 - 1 -: ` :
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As a result, contamination occurred after about 20,000 impressions ~ere made.
Further, the latter type of agent is not effective unlcss conlplete heat-curing is conduc-ted after pre-treating witll the agent. Additionally, even if the agent is heat-cured its durability is not always satisfactory and contamination still occurs aftcr printing about 30,000 impressions.
It is an object of this invention to solve the above problems in resin based letterpress printing plates.
SU~IARY 0~ INVENTION
The p~esent invention prevents or reduces contamination by use of a photosensitive resin composition which includes about 0.001 to about 5% by weight of a fluorocarbon surfactant containing perfluoroalkyl groups ~C4-C14).
The surfactant is preferably nonionic. The resin letterpress plate made from the photosensitive resin composition of the present invention displays a remarkable contamination preventing effect, i.e. an increase in the number of impressions that can be made without evidencing any contamination. Use of the composition of this invention renders quite unnecessary such conventional operations as preliminary surface treatment. By virtue of use of this composition it is possible to subject the above letterpress plate to printing merely by mounting it on a rotary press.
In the present invention the nonionic fluorocarbon surfactant contains perfluoroalkyl groups (C4-C14) and is preferably contained in a photosensitive resin composition in amounts of about 0.001 wt.% to about 5 wt.%. If the content is less than about 0.001 wt.%, its effect becomes poor.
If its content exceeds about 5 wt.% it will still be useful but will be less effective, since its ink repellency becomes too strong with the result that ` ~ the photographic printing effect becomes poor. Additionally, if the content
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exceeds about 5% the cost becomes economically disadvantageous.
The fluorocarbon ,urfactant of the present invention is preferably nonionic. However, it has also been found that an anionic, cationic or ampholytic fluorocarbon surfactant is also effective to prevent contamination.
However, compounds having these ionic properties are generally not preferred because it is difficult to maintain their stability with time after they have been combined with a photosensitive resin composition. In the case of a liquid photosensitive resin composition, thickening or gellation is likely to occur.
Further, if the photosensitive resin composition is solid such agents are lt) likely to cause problems such as inability of development.
Examples of the fluorocarbon surfactants used in the present invention include (2-perfluorooctylethyl polyoxypropylene ether carbamyl)-polyoxyethylenecarbamyltoluene, 2-perfluorooctyl-1-acetoxymethylethyl carbamyltolylenestearyl polyoxyethylene carbamate, 2-perfluoroalkyl (C4-C14) ethanol, 2-perfluorooctyl-1-methylethyl polyoxyethylene ether, perfluoroisop-ropoxypropylcilsesquinoxane. Of course, the claimed fluorocarbon surfactant is not restricted by the above examples.
The present invention includes photosensitive resin compositions, which are liquid or solid at room temperature. A preferred liquid type photosensitive resin includes predominantly a polyurethane, polyester or synthetic rubber. Further, a preferred solid type photosensitive resin includes mainly polyvinyl alcohol or nylon. Of course, neither the liquid or the solid resin is restricted to the above examples.
The present invention is exemplified by the following l~orking Examples and Comparative Examples.
~ Example 1 :' ~ - 3 -, ., :
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60 g of urethane tyye prepolymer obtained by the thermal reaction of polyoxypropylene glycol (molecular weight of 1000), tolylene diisocyanate and hydroxyethyl methacrylatc, 35 g of diethylene glycol dimethacrylate and 5 g of pentaerythritol tetrakis (~-lnercaptopropionate) were mixed with 0~5 g of hydroquinonemonomethyl ether as the thermal polymerization inhibitor and 1 g of benzoin ethyl ether as the sensitizer. There resulted 101.5 g of urethane type photosensitive resin composition for letterpress printing.
To this composition 0.5 g of 2-perfluorooctyl-l-methylethyl-polyoxyethylene ether was added and then mixed. The mixture exhibited good storage stability. When this mixture was used in a newspaper rotary press, no contamination occurred until 60,000 impressions were made.
Example 2 To 101.5 g of the same urethane type photosensitive resin as in Example 1, 0.5 g of (2-perfluorooctylethyl polyoxypropylene ether carbamyl)-polyoxyethylenecarbamyltoluene, was added and then mixed. The mixture exhibited good storage stability. I~hen this mixture was used in a newspaper rotary press, no contamination occurred until 60,000 impressions were made.
Example 3 ~ An unsaturated polyester was produced by the thermal reaction of dimethyl terephthalate, diethylene glycol, propylene glycol, 1,~, 8-naphthalene tricarboxylic acid anhydride and citraconic acid anhydride. To 70 g of this resin 30 g of acrylamide, 0.01 g of hydroquinone and 0.7 g of benzoin were added to produce a polyester type photosensitive resin. Further, 0.5 g of the same fluorocarbon surfactant as that in Example 2 was added to this resin. A printing plate produced using this mixture was used in a newspaper rotary press and no contamination occurred until 50J000 impressions were made.
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Example 4 A solid polyvinyl alcohol type photosensitive resin was produced by mixing 60 g of polyvinyl alcohol, 30 g of hydroethyl methacrylate, 0.1 g of hydroquinone, 5 g of ben~yl dimethyl ~etal and 0.5 g of the ; fluorocarbon surfactant used in Example 2. This blend had good storage stability. A printing p]ate produced from this mixture was used on a press ; and no contamination occurred until 50,000 impressions were made.
Comparative Example 1 In the case of a urethane type plate prepared without using the fluorocarbon surfactant of Example 1 contamination occurred at the time 10,000 impressions were made.
Comparative Example 2 In the case of a polyester type plate produced without using the fluorocarbon surfactant of Example 3 contamination occurred at the time 8,000 impressions were made.
Comparative Example 3 In the case of a polyvinyl alcohol type plate produced without using the-fluorocarbon surfactant of Example ~ contamination occurred at the time 8,000 impressions were made.
Examples 5-16 and Comparative Examples ~-7 A printing plate was produced from a composition and used in a newspaper rotary press, said composition being obtained by mixing each of the following nonionic fluorocarbon surfactants A-F in fixed amounts with various resins as shown in Table 1. The number of impressions made without detection of contamination and the photographic printing effect are shown in Table 1.
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Surfactant ~: 2-perfluorooctyl-1-methylethyl polyoxyethylene ether;
B: (2-perfluorooctylethyl polyoxypropylene ether carbamyl)-polyoxyethylenecarbamyltoluene;
C: 2-perfluorooctyl-1-acetoxymethylethyl carbamyl-tolylenestearyl polyoxyethylene carbamate;
D: 2-perfluorooctyl ethanol;
E: perfluorisopropoxypropylcilsesquinoxane; and F: perfluorooctanesulfonic acid diethanolamide.
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~Z329~5 Number of Impressions Photo with contami- graphic . Fluorocarbon Content nation not printing Ex. No. Surfactant (wt.%) ~-- Resin detected effect Comp, ~ A 0.0005 Urethane type10,000 Good ; Ex. 4 in Example 1 Ex. 5 A 5 " 65~000 Good " 6 A 7 " 65,000 Poor Comp, B 0.0005 " 10,000 Good Exp 5 Ex. 7 B 5 " 65,000 Good " 8 B 7 " 65,000 Poor " 9 C 0.5 " 65,000 Good " 10 D 0.5 " 60,000 Good " 11 E 0.5 " 60,000 Good " 12 F 0.5 " 65,000 Good " 13 C 0.5 Polyester typeS0,000 Good in Example 3 " 14 D 0.5 Polyvinyl 60,000 Good alcohol type in Example 4 ; ~ " 15 E 0.5 Nylon type 60,000 Good " 16 F 0.5 Synthetic 50,000 Good rubber type Comp. Not Used - Nylon type 10,000 Good Exp. 6 " 7 Not Used - Synthetic 5,000 Good rubber type ~23;~9~L5 The nylon type resins, see Example 15 and Comparative Example 6 in Table 1 which comprise 100 wt. parts of a copolymer polyamide of N-bis~2-aminoethyl)methylamine, adipic acid and ~-caprolactam, 5 wt. parts of methylenel)is acrylamide, 0.1 wt. part of hydroquinone and 1 wt. part of benzoin. Table 1 shows that when the fluorocarbon surfactant of the present invention is used as in Example 15, 60,000 impressions were made without detection of contamination, whereas without the surfactant only 10,000 impressions were made as illustrated by Comparative Example 6.
The synthetic rubber type resins, see Example 16 and Comparative Example 1, comprise 100 wt. parts of a styrene-butadiene type block copolymer (styrene content:35-50 wt.%), 20 wt. parts of 1,6-hexanediol diacrylate, 0.5 wt. part of tertiary butylphenol and 1 wt. part of benzoin ethyl ether. Table 1 shows that when the surfactant of the present invention is used as in Example 16, 50,000 impressions were made with no contamination detected, whereas without the surfactant only 5,000 impressions were made as illustrated by Comparative Example 7.
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exceeds about 5% the cost becomes economically disadvantageous.
The fluorocarbon ,urfactant of the present invention is preferably nonionic. However, it has also been found that an anionic, cationic or ampholytic fluorocarbon surfactant is also effective to prevent contamination.
However, compounds having these ionic properties are generally not preferred because it is difficult to maintain their stability with time after they have been combined with a photosensitive resin composition. In the case of a liquid photosensitive resin composition, thickening or gellation is likely to occur.
Further, if the photosensitive resin composition is solid such agents are lt) likely to cause problems such as inability of development.
Examples of the fluorocarbon surfactants used in the present invention include (2-perfluorooctylethyl polyoxypropylene ether carbamyl)-polyoxyethylenecarbamyltoluene, 2-perfluorooctyl-1-acetoxymethylethyl carbamyltolylenestearyl polyoxyethylene carbamate, 2-perfluoroalkyl (C4-C14) ethanol, 2-perfluorooctyl-1-methylethyl polyoxyethylene ether, perfluoroisop-ropoxypropylcilsesquinoxane. Of course, the claimed fluorocarbon surfactant is not restricted by the above examples.
The present invention includes photosensitive resin compositions, which are liquid or solid at room temperature. A preferred liquid type photosensitive resin includes predominantly a polyurethane, polyester or synthetic rubber. Further, a preferred solid type photosensitive resin includes mainly polyvinyl alcohol or nylon. Of course, neither the liquid or the solid resin is restricted to the above examples.
The present invention is exemplified by the following l~orking Examples and Comparative Examples.
~ Example 1 :' ~ - 3 -, ., :
~: . . .. .
~ . .
:L~3~9~S
60 g of urethane tyye prepolymer obtained by the thermal reaction of polyoxypropylene glycol (molecular weight of 1000), tolylene diisocyanate and hydroxyethyl methacrylatc, 35 g of diethylene glycol dimethacrylate and 5 g of pentaerythritol tetrakis (~-lnercaptopropionate) were mixed with 0~5 g of hydroquinonemonomethyl ether as the thermal polymerization inhibitor and 1 g of benzoin ethyl ether as the sensitizer. There resulted 101.5 g of urethane type photosensitive resin composition for letterpress printing.
To this composition 0.5 g of 2-perfluorooctyl-l-methylethyl-polyoxyethylene ether was added and then mixed. The mixture exhibited good storage stability. When this mixture was used in a newspaper rotary press, no contamination occurred until 60,000 impressions were made.
Example 2 To 101.5 g of the same urethane type photosensitive resin as in Example 1, 0.5 g of (2-perfluorooctylethyl polyoxypropylene ether carbamyl)-polyoxyethylenecarbamyltoluene, was added and then mixed. The mixture exhibited good storage stability. I~hen this mixture was used in a newspaper rotary press, no contamination occurred until 60,000 impressions were made.
Example 3 ~ An unsaturated polyester was produced by the thermal reaction of dimethyl terephthalate, diethylene glycol, propylene glycol, 1,~, 8-naphthalene tricarboxylic acid anhydride and citraconic acid anhydride. To 70 g of this resin 30 g of acrylamide, 0.01 g of hydroquinone and 0.7 g of benzoin were added to produce a polyester type photosensitive resin. Further, 0.5 g of the same fluorocarbon surfactant as that in Example 2 was added to this resin. A printing plate produced using this mixture was used in a newspaper rotary press and no contamination occurred until 50J000 impressions were made.
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Example 4 A solid polyvinyl alcohol type photosensitive resin was produced by mixing 60 g of polyvinyl alcohol, 30 g of hydroethyl methacrylate, 0.1 g of hydroquinone, 5 g of ben~yl dimethyl ~etal and 0.5 g of the ; fluorocarbon surfactant used in Example 2. This blend had good storage stability. A printing p]ate produced from this mixture was used on a press ; and no contamination occurred until 50,000 impressions were made.
Comparative Example 1 In the case of a urethane type plate prepared without using the fluorocarbon surfactant of Example 1 contamination occurred at the time 10,000 impressions were made.
Comparative Example 2 In the case of a polyester type plate produced without using the fluorocarbon surfactant of Example 3 contamination occurred at the time 8,000 impressions were made.
Comparative Example 3 In the case of a polyvinyl alcohol type plate produced without using the-fluorocarbon surfactant of Example ~ contamination occurred at the time 8,000 impressions were made.
Examples 5-16 and Comparative Examples ~-7 A printing plate was produced from a composition and used in a newspaper rotary press, said composition being obtained by mixing each of the following nonionic fluorocarbon surfactants A-F in fixed amounts with various resins as shown in Table 1. The number of impressions made without detection of contamination and the photographic printing effect are shown in Table 1.
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Surfactant ~: 2-perfluorooctyl-1-methylethyl polyoxyethylene ether;
B: (2-perfluorooctylethyl polyoxypropylene ether carbamyl)-polyoxyethylenecarbamyltoluene;
C: 2-perfluorooctyl-1-acetoxymethylethyl carbamyl-tolylenestearyl polyoxyethylene carbamate;
D: 2-perfluorooctyl ethanol;
E: perfluorisopropoxypropylcilsesquinoxane; and F: perfluorooctanesulfonic acid diethanolamide.
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~Z329~5 Number of Impressions Photo with contami- graphic . Fluorocarbon Content nation not printing Ex. No. Surfactant (wt.%) ~-- Resin detected effect Comp, ~ A 0.0005 Urethane type10,000 Good ; Ex. 4 in Example 1 Ex. 5 A 5 " 65~000 Good " 6 A 7 " 65,000 Poor Comp, B 0.0005 " 10,000 Good Exp 5 Ex. 7 B 5 " 65,000 Good " 8 B 7 " 65,000 Poor " 9 C 0.5 " 65,000 Good " 10 D 0.5 " 60,000 Good " 11 E 0.5 " 60,000 Good " 12 F 0.5 " 65,000 Good " 13 C 0.5 Polyester typeS0,000 Good in Example 3 " 14 D 0.5 Polyvinyl 60,000 Good alcohol type in Example 4 ; ~ " 15 E 0.5 Nylon type 60,000 Good " 16 F 0.5 Synthetic 50,000 Good rubber type Comp. Not Used - Nylon type 10,000 Good Exp. 6 " 7 Not Used - Synthetic 5,000 Good rubber type ~23;~9~L5 The nylon type resins, see Example 15 and Comparative Example 6 in Table 1 which comprise 100 wt. parts of a copolymer polyamide of N-bis~2-aminoethyl)methylamine, adipic acid and ~-caprolactam, 5 wt. parts of methylenel)is acrylamide, 0.1 wt. part of hydroquinone and 1 wt. part of benzoin. Table 1 shows that when the fluorocarbon surfactant of the present invention is used as in Example 15, 60,000 impressions were made without detection of contamination, whereas without the surfactant only 10,000 impressions were made as illustrated by Comparative Example 6.
The synthetic rubber type resins, see Example 16 and Comparative Example 1, comprise 100 wt. parts of a styrene-butadiene type block copolymer (styrene content:35-50 wt.%), 20 wt. parts of 1,6-hexanediol diacrylate, 0.5 wt. part of tertiary butylphenol and 1 wt. part of benzoin ethyl ether. Table 1 shows that when the surfactant of the present invention is used as in Example 16, 50,000 impressions were made with no contamination detected, whereas without the surfactant only 5,000 impressions were made as illustrated by Comparative Example 7.
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Claims (12)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A surfactant for reducing contamination in resin based printing plates usable in a photosensitive resin composition wherein the surfactant comprises a fluorocarbon with C4-C14 perfluoralkyl groups or mixtures thereof.
2. A surfactant as in Claim 1 wherein the fluorocarbon is nonionic.
3. A surfactant as in claim 1 or 2 wherein the surfactant comprises about 0.001% to about 5% by weight of the resin composition.
4. A surfactant as in claim 2 wherein the surfactant is selected from the group consisting of 2-perfluorooctyl-1-methylethyl polyoxyethylene ether, (2-perfluorooctylethyl polyoxypropylene ether carbamyl)-polyoxyethylene-carbamyltoluene, 2-perfluorooctyl-1-acetoxymethylethyl carbamyltolylenestearyl polyoxyethylene carbamate, 2-perfluorooctyl ethanol, perfluoroisopropoxypropyl-cilsesquinoxane, perfluoro-octanesulfonic acid diethanolamide, and mixtures thereof.
5. A composition suitable for use with a resin based printing plate comprising a photosensitive resin and a surfactant comprised of a fluorocarbon with C4-C14 perfluoroalkyl groups or mixtures thereof.
6. A composition as in Claim 5 wherein the fluorocarbon is nonionic.
7. A composition as in Claim 5 or 6 wherein the surfactant comprises about 0.001% to about 5% by weight of the photosensitive resin.
8. A composition as in Claim 6 wherein the surfactant is selected Case 2735 9 from the group consisting of 2-perfluorooctyl-1-methylethyl polyoxyethylene ether, (2-perfluorooctylethyl polyoxypropylene ether carbamyl)-polyoxyethylene-carbamyltoluene, 2-perfluorooctyl carbamate, 2-perfluorooctyl ethanol, perfluoroisopropoxypropylcilsesquinoxane, perfluorooctanesulfonic acid diethanolamide, and mixtures thereof.
9. A method of reducing contamination of resin based printed plates comprising including in a photosensitive resin composition a surfactant comprising a fluorocarbon with C4-C14 perfluoroalkyl groups or mixtures thereof.
10. A method as in Claim 9 wherein the fluorocarbon is nonionic.
11. A method as in Claim 8 or 9 wherein the surfactant comprises about 0.01% to about 5% by weight of the resin composition.
12. A method as in Claim 10 wherein the surfactant is selected from the group consisting of 2-perfluorooctyl-1-methylethyl polyoxyethylene ether, (2-perfluorooctylethyl polyoxypropylene ether carbamyl)-polyoxyethylenecarbamyl-toluene, 2-perfluorooctyl-1-acetoxymethylethyl carbamyl-tolylenestearyl polyoxyethylene carbamate, 2-perfluorooctyl ethanol, perfluoroispropoxypropyl-cilsesquinoxane perfluorooctanesulfonic acid diethanolamide and mixtures thereof.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11249/83 | 1983-01-28 | ||
| JP58011249A JPS59137943A (en) | 1983-01-28 | 1983-01-28 | Photosensitive resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1232915A true CA1232915A (en) | 1988-02-16 |
Family
ID=11772662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000445119A Expired CA1232915A (en) | 1983-01-28 | 1984-01-11 | Photosensitive resin compositions |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS59137943A (en) |
| AU (1) | AU556611B2 (en) |
| CA (1) | CA1232915A (en) |
| DE (1) | DE3402465A1 (en) |
| GB (1) | GB2134275B (en) |
| IT (1) | IT1206696B (en) |
| NL (1) | NL8400257A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61226746A (en) * | 1985-03-30 | 1986-10-08 | Japan Synthetic Rubber Co Ltd | Radiation sensitive composition |
| JPS61226745A (en) * | 1985-03-30 | 1986-10-08 | Japan Synthetic Rubber Co Ltd | Radiation sensitive composition |
| JPH0721626B2 (en) * | 1985-08-10 | 1995-03-08 | 日本合成ゴム株式会社 | Resist composition for semiconductor fine processing |
| JPH083630B2 (en) * | 1986-01-23 | 1996-01-17 | 富士写真フイルム株式会社 | Photosensitive composition |
| JPH06105351B2 (en) * | 1986-03-27 | 1994-12-21 | 富士写真フイルム株式会社 | Photosensitive composition |
| JPH0762761B2 (en) * | 1986-03-28 | 1995-07-05 | 富士写真フイルム株式会社 | Image forming material |
| JPH06105350B2 (en) * | 1987-07-13 | 1994-12-21 | 富士写真フイルム株式会社 | Photosensitive composition for lithographic printing plate |
| JP2878150B2 (en) * | 1994-04-27 | 1999-04-05 | 東京応化工業株式会社 | Coating solution for resist and resist material using the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3347676A (en) * | 1964-04-30 | 1967-10-17 | Du Pont | Photopolymerizable compositions and process |
| JPS54135004A (en) * | 1978-04-10 | 1979-10-19 | Fuji Photo Film Co Ltd | Photosensitive flat printing plate |
| US4252887A (en) * | 1979-08-14 | 1981-02-24 | E. I. Du Pont De Nemours And Company | Dimers derived from unsymmetrical 2,4,5-triphenylimidazole compounds as photoinitiators |
| JPS5660441A (en) * | 1979-10-22 | 1981-05-25 | Asahi Chem Ind Co Ltd | Photosensitive resin composition improved in water development property and manufacture of photosensitive resin plate using this composition |
| DE3022362A1 (en) * | 1980-06-14 | 1981-12-24 | Hoechst Ag, 6000 Frankfurt | LIGHT-SENSITIVE COPYING MATERIAL AND METHOD FOR THE PRODUCTION THEREOF |
-
1983
- 1983-01-28 JP JP58011249A patent/JPS59137943A/en active Pending
-
1984
- 1984-01-11 CA CA000445119A patent/CA1232915A/en not_active Expired
- 1984-01-23 GB GB08401661A patent/GB2134275B/en not_active Expired
- 1984-01-24 AU AU23716/84A patent/AU556611B2/en not_active Ceased
- 1984-01-25 DE DE19843402465 patent/DE3402465A1/en not_active Withdrawn
- 1984-01-27 IT IT8419349A patent/IT1206696B/en active
- 1984-01-27 NL NL8400257A patent/NL8400257A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IT8419349A0 (en) | 1984-01-27 |
| JPS59137943A (en) | 1984-08-08 |
| GB2134275B (en) | 1987-05-13 |
| GB2134275A (en) | 1984-08-08 |
| AU2371684A (en) | 1984-08-02 |
| IT1206696B (en) | 1989-04-27 |
| GB8401661D0 (en) | 1984-02-22 |
| AU556611B2 (en) | 1986-11-13 |
| DE3402465A1 (en) | 1984-08-02 |
| NL8400257A (en) | 1984-08-16 |
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