GB2032937A - Photosensitive Resin Compositions Having Increased Viscosity - Google Patents

Photosensitive Resin Compositions Having Increased Viscosity Download PDF

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Publication number
GB2032937A
GB2032937A GB7843274A GB7843274A GB2032937A GB 2032937 A GB2032937 A GB 2032937A GB 7843274 A GB7843274 A GB 7843274A GB 7843274 A GB7843274 A GB 7843274A GB 2032937 A GB2032937 A GB 2032937A
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photosensitive
polycarboxylic acid
unsaturated
layer
polyol
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GB2032937B (en
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Hercules LLC
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Hercules LLC
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    • 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
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
    • C08F299/0407—Processes of polymerisation
    • C08F299/0421—Polymerisation initiated by wave energy or particle radiation
    • C08F299/0428—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F299/0435—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • 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
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

Photosensitive compositions useful for producing high quality relief printing plates comprise at least one unsaturated polyester, at least one ethylenically unsaturated, addition polymerisable monomer, at least one photosensitive initiator and a poly(hydroxyl ether) derived from a diphenol and an epihalohydrin, such as bisphenol A-epichlorohydrin resin. The poly(hydroxyl ether) increases the viscosity of the photosensitive composition such that the composition is less likely to flow during the plate-making process, thereby avoiding undesirable blemishes on the finished plate.

Description

SPECIFICATION Polymers for Increasing the Viscosity of Photosensitive Resins This invention relates to a liquid photosensitive composition having a relatively high viscosity and to a method for increasing the viscosity of liquid unsaturated photosensitive polyester resin formulations, as well as to photosensitive elements employing the said compositions.
The use of liquid photopolymerizable resins for making relief printing plates is well known (see U.S. Patent 3,556,791). Basically, the platemaking process involves spreading a uniform layer of liquid photopolymerizable resin on a substrate and exposing selected portions of the liquid resin layer to actinic radiation, whereby the exposed areas are hardened while the unexposed areas remain liquid.
The plate is then subjected to a washing process which removes the unexposed, still liquid portions from the relief plate's surface.
Basically, most photosensitive compositions contain three components~(1 ) a binder of some type, generally a polymer or resin (referred to herein as the prepolymer), (2) a hardening and insolubilizing material, generally a cross-linking agent or polymerizable monomer, and (3) a photosensitive initiator.
Typical of the binders are the unsaturated polyesters prepared according to traditional methods from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid and at least one polyol. Examples of unsaturated polycarboxylic acids and anhydrides which can be used in the preparation of unsaturated polyesters are maleic acid, furmaric acid, citraconic acid, mesaconic acid, itaconic acid, glutaconic acid, muconic acid, aconitic acid and their anhydrides, in particular, maleic anhydride, citraconic anhydride and itaconic anhydride. Adipic acid is normally used as the saturated polycarboxylic acid.Examples of polyols which can be used in the preparation of unsaturated polyesters are ethylene glycol, 1 2-propylene glycol, propanediol-1,3, butanediol-1,4, diethylene glycol, dipropylene glycol, polyethylene glycol, polypropylene glycol, polybutylene glycol, etc.
Typical hardening materials are the ethylenically unsaturated addition polymerization monomers such as acrylic acid, methacrylic acid, methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-hexyl acrylate, n-octyl acrylate, cyclohexyl acrylate, allyl acrylate, glycidyl acrylate, styrene, vinyl toluene, divinyl benzene, carboxystyrene, diallyl phthalate, triallyl cyanurate, vinyl acetate, acrylamide, methacrylamide, N-methylol acrylamide, N-methylol methacrylamide, N-methoxymethyl acrylamide, N-ethoxymethyl acrylamide, N-ethoxymethyl methacrylamide, N-n-butoxymethyl acrylamide, N,N'-methylene bis acrylamide, N,N'-methylene bis methacrylamide, N,N'-trimethylene bis acrylamide, N,N'-hexamethylene bis acrylamide, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxpropyl acrylate, 3-chloro-2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, diethylene glycol monoacrylate, dipropylene glycol monoacrylate, polyethylene glycol monoacrylate, ethylene glycol diacrylate, tetraethylene glycol diacrylate, propylene glycol dimethacrylate, diethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, trimethylolpropane triacrylate, N-3-oxo-propyl acrylamide, N-3-oxo-butyl acrylamide, N-3-oxo- 1 -methylbutyl acrylamide, N-3-oxo- 1 -dibutyl-2-n- propylheptyl acrylamide, etc.
The specific photosensitive initiator used will depend upon the other components as well as the light source employed. Typical photosensitive initiators are the benzoins, such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, alpha-methylbenzoin, alpha-ethylbenzoin, alpha-phenylbenzoin, alpha-allylbenzoin, etc.; the anthraquinones, such as anthraquinone, chloroanthraquinone, methylanthraquinone, ethylanthraquinone, etc.; the diketones, such as benzil, diacetyl, etc.; the phenones, such as acetophenone, benzophenone, w-bromoacetophenone, etc.; the disulfides, such as diphenyldisulfide, tetraethylthiuramidisulfide, etc.; 2-naphthalene-sulfonyl chloride, etc.
Those skilled in the art will realize that the number of basic components can be more than three, such as where a mixture of two or more materials is used for one of the above components. In addition to the basic components, the photosensitive composition may also contain thermal stabilizers, fillers, plasticizers, etc., as is well known in the art.
The photosensitive unsaturated polyester resin compositions described above are liquid in their uncured state. As such, they are susceptible to undesirable flow during the platemaking process. This tendency to flow is directly related to resin viscosity, i.e., the lower the resin viscosity the more likelihood of resin flow.
Low resin viscosity results in undesirable flow of the liquid photopolymer resin during the platemaking process. This resin flow can cause split lines and abnormal shoulders on half-tone dots in the finished plate. Also, to produce relief plates of consistent quality, it is important that the viscosity of the liquid photopolymerizable resin be uniform from batch to batch.
Increasing the resin viscosity decreases the incidence of flow-related printing defects. Several methods have been used to increase the viscosity of liquid photopolymerizable resins. Using a higher molecular weight, higher viscosity photopolymer is one obvious method. However, the higher molecular weight prepolymer is closer to its gel point than a lower viscosity prepolymer. Thus, close control during the prepolymer preparation is necessary or the entire reaction mixture may gel. Also, it is difficult to prepare a high viscosity prepolymer with good batch to batch uniformity.
Another way in which the resin viscosity can be controlled is by changing the resin formulation.
By increasing the prepolymer concentration and/or decreasing the concentration of monomers which have an especially low viscosity, the overall viscosity of the resin can be increased. However, unless, the desired viscosity increase is small (e.g., a few thousand cps.), large changes in the physical properties of the cured resin can result.
According to the invention, a liquid photosensitive composition comprises (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated addition polymerizable monomer; (c) at least one photosensitive initiator and (d) from about 0.1 to about 15%, based on total weight, of a poly(hydrbxylether) derived from a diphenol and an epihalohydrin having a molecular weight in the range of from about 8,000 to about 200,000.
Also according to the invention, a process for increasing the viscosity of liquid photosensitive compositions containing (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; and (b) at least one ethylenically unsaturated, addition polymerizable monomer comprises dissolving from about 0.1 to about 1 5%, based on total weight, of the said poly(hydroxyl ether).
Preferably, the amount of poly(hydroxyl ether) is from about 2% to about 5% based on total weight.
The poly(hydroxyl ether) resin may be added to the photosensitive resin formulation by dissolving it in the monomer component prior to the addition of the monomer to the unsaturated polyester binder.
While the poly(hydroxyl ether) can be added to the unsaturated polyester prepolymer component, considerably more time is required for the phenoxy resin to dissolve than when added to the monomer component.
The thus prepared photosensitive resin formulation can be used to produce relief printing plates using standard platemaking techniques. The phenoxy resin does not interfere with the photochemistry of the photosensitive resin, nor does it affect the removal of uncured resin during the washing process.
Also, the addition of the phenoxy resin to the photosensitive resin formulation does not affect the clarity of the photosensitive resin. Further, the physical properties of the cured photosensitive resin remain unchanged.
Example 1 A photosensitive composition is prepared by thoroughly blending, at room temperature, 100 parts of an unsaturated polyester prepolymer, and 61.3 parts of a solution containing polymerizable monomers, a photoinitiator and thermal polymerization inhibitors. The unsaturated polyester prepolymer used in this composition is prepared by reacting 9.5 mole of furmaricacid, 0.25 mole of adipic acid, 0.25 mole of itaconic acid,0.50 mole of diethylene glycol and 0.50 mole of propylene glycol at 1 90-2000C. for 12 hours under an atmosphere of nitrogen gas. The unsaturated polyester prepolymer has an acid number of 29 and a Brookfield viscosity of 1 560 cps. at 1000C. and 272,000 cps. at 250C.The monomer solution is prepared by mixing the following ingredients and stirring until the solid ingredients dissolve: % By Weight Diethylene glycol dimethacrylate 55.2 2-Hydroxyethyl methacrylate 26.4 Diacetone acrylamide 13.3 Benzoin ethyl ether 4.7 Butylated hydroxy toluene 0.26 4-Methoxyphenol 0.14 After thoroughly blending the unsaturated polyester prepolymer and the monomer solution, the photosensitive resin formulation's Brookfield viscosity is 5640 cps. at 250C.
Examples 24 The following examples illustrate the increase in viscosity of the photosensitive resin formulation described in Example 1 upon addition of bisphenol A-epichlorohydrin resin (Bakelite Phenoxy Resin PKHH made by Union Carbide Corporation, molecular weight approximately 30,000).
Phenoxy Resin Brookfield Viscosity Example (parts per hundred) (cps. at 25 0C.) 2 1.24 8,960 3 2.48 13,840 4 4.96 21,280 Example 5 A photosensitive composition is prepared by blending, at room temperature, 77 parts of an unsaturated polyester prepolymer with 23 parts of a solution containing polymerizable monomers, a photoinitiator and thermal polymerization inhibitors, the unsaturated polyester prepolymer used in this composition is prepared by reacting 0.20 mole of fumaric acid,0.30 mole of isophthalic acid,0.50 mole of adipic acid,0.25 mole of propylene glycol and 0.75 mole of diethylene glycol at 190--2000C. for 12 hours under an atmosphere of nitrogen gas.The unsaturated polyester prepolymer has an acid number of 28 and a Brookfield viscosity of 1 700 cps. at 1000C. The monomer solution is prepared by mixing the following ingredients and stirring until the solid ingredients dissolved: Parts by Weight 2-Hydroxyethyl methacrylate 15 Diacetone acrylamide 30 Tetraethylene glycol dimethacrylate 55 Benzoin isobutyl ether 1.80 Butylated hydroxy toluene 0.10 4-Methoxyphenol 0.05 After thoroughly blending the unsaturated polyester prepolymer and the monomer solution, the photosensitive resin formulation's Brookfield viscosity is 6200 cps. at 250C.
Examples 6-8 The following examples illustrate the increase in viscosity of the photosensitive resin formulation described in Example 5 upon addition of bisphenol A-epichlorohydrin resin (Bakelite Phenoxy Resin PKHH made by Union Carbide Corporation, Molecular weight approximately 30,000).
Phenoxy Resin Brookfield Viscosity Example (parts per hundred) (cps. at 25 C.) 6 0.75 7,500 7 1.50 9.000 8 3.0 16,000 Example 9 Letterpress printing plates are made with the photosensitive resin formulation described in Example 1 with 2.3 parts per hundred phenoxy resin dissolved therein. The printing plates are made by doctoring a 40 mil thick layer of resin on a 4 mil polyester backing sheet support, and then exposing the resin through an image-bearing negative transparency to a 3 kilowatt medium pressure mercury arc lamp for two minutes. The uncured photopolymer resin is washed away with an aqueous solution containing 0.1% sodium hydroxide. The resulting plant is dried and cured by exposing it to the 3 kilowatt mercury arc light for an additional two minutes. The resulting printing plate is completely tack free.
The thus prepared printing plate is mounted on a cohnmercial newspaper printing press and printed 2000 high quality impressions. Fine lines and half-tone areas are especially sharp and clear.

Claims (7)

Claims
1. A liquid photosensitive composition comprising: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated addition polymerizable monomer; (c) at least one photosensitive initiator; and (d) from about 0.1 to about 1 5%, based on total weight, of a poly(hydroxyl ether) derived from a diphenol and an epihalohydrin having a molecular weight in the range of from about 8,000 to about 200,000.
2. A liquid photosensitive composition comprising: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated addition polymerizable monomer; (c) at least one photosensitive initiator; and (d) from about 0.1 to about 1 5%, based on total weight, of a bisphenol A-epichlorohydrin resin having a molecular weight in the range of from about 8,000 to about 200,000.
3. A process for increasing the viscosity of liquid photosensitive compositions containing: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated addition polymerizable monomer; and (c) at least one photosensitive initiator, staid process comprising dissolving from about 0.1 to about 15%, based on total weight of a poly(hydroxyl ether derived from a diphenol and an epihalohydrin having a molecular weight in the range of from about 8,000 to about 200,000 in the photosensitive composition.
4. A process for increasing the viscosity of liquid photosensitive compositions containing: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated addition polymerizable monomer; and (c) at least one photosensitive initiator, said process comprising dissolving from about 0.1 to about 15%, based on total weight, of a bisphenol A-epichlorohydrin resin having a molecular weight in the range of from about 8,000 to about 200,000 in the photosensitive composition.
5. A process for preparing printing plates which comprises forming a photosensitive element by depositing a layer of a photosensitive composition onto a support, said composition comprising: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated, addition polymerizable monomer; (c) at least one photosensitive initiator; and (d) a bisphenol Aepichlorohydrin resin, exposing a selected area of the photosensitive layer to actinic radiation until photo cross-linking of the exposed area of said layer is substantially completed, and subsequently removing the nonexposed area of said layer.
6. A photosensitive element comprising a support layer and a liquid photosensitive layer, said liquid photosensitive layer comprising: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated addition polymerizable monomer; (c) at least one photosensitive initiator; and (d) from about 0.1 to about 15%, based on total weight, of a bisphenol A-epichlorohydrin resin having a molecular weight in the range of from about 8,000 to about 200,000.
7. A photosensitive element comprising a support layer and a layer of a liquid photosensitive composition as claimed in claim 1,2 or 3.
7. In a liquid photosensitive composition comprising: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated addition polymerizable monomer; and (c) at least one photosensitive initiator; the improvement of adding from about 0.1 to about 15%, based on total weight, of a poly(hydroxyl ether) derived from a diphenol and an epihalohydrin having a molecular weight in the range of from about 8,000 to about 200,000.
8. The composition of claim 7 wherein the said polythydroxyl ether) is a bisphenol Aepichlorohydrin resin.
9. In a process for increasing the viscosity of a liquid photosensitive composition comprising: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated addition polymerizable monomer; and (c) at least one photosensitive initiator; the improvement of dissolving in the said liquid photosensitive composition from about 0.1 to about 15%, based on total weight, of a poly(hydroxyl ether) derived from a diphenol and an epihalohydrin having a molecular weight in the range of from about 8,000 to about 200,000.
10. The process of claim 9 wherein the said poly(hydroxyl ether) is a bisphenol A-epichlorohydrin resin.
11. In a photosensitive element comprising a support layer and a liquid photosensitive layer, said liquid photosensitive layer comprising: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated, addition polymerizable monomer; and (c) at least one photosensitive initiator; the improvement of adding from about 0.1 to about 15%, based on total weight, of a bisphenol A-epichlorohydrin resin having a molecular weight in the range of from about 8,000 to about 200,000.
New Claims or Amendments to Claims filed on 20 April 1979 and 6 November 1978.
Superseded Claims 1 to 11.
New or Amended Claims 1 to 7:
1. A liquid photosensitive composition comprising: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated addition polymerizable monomer; (c) at least one photosensitive initiator; and (d) from about 0.1 to about 15 per cent, based on total weight, of a poly(hydroxyl ether) derived from a diphenol and an epihalohydrin having a molecular weight in the range of from about 8,000 to about 200,000.
2. A composition according to claim 1 wherein the poly(hydroxyl ether) is a bisphenol Aepichlorohydrin resin.
3. A composition according to claim 1 substantially as described in the foregoing Examples.
4. A process for increasing the viscosity of liquid photosensitive compositions containing: (a) at least one unsaturated polyester produced from at least one unsaturated polycarboxylic acid, a saturated polycarboxylic acid, and at least one polyol; (b) at least one ethylenically unsaturated addition polymerizable monomer; and (c) at least one photosensitive initiator, said process comprising dissolving from about 0.1 to about 1 5 per cent, based on total weight, of a poly(hydroxyl ether) derived from a diphenol and an epihalohydrin having a molecular weight in the range of from about 8,000 to about 200,000 in the photosensitive composition.
5. A process according to claim 4 wherein the poly(hydroxyl ether) is a bisphenol Aepichlorohydrin resin.
6. A process for preparing printing plates which comprises forming a photosensitive element by depositing a layer of a photosensitive composition as claimed in claim 1,2 or 3 onto a support, exposing a selected area of the photosensitive layer to actinic radiation until photo cross-linking of the exposed area of said layer is substantially completed, and subsequently removing the nonexposed area of said layer.
GB7843274A 1978-11-06 1978-11-06 Photosensitive resin compositions having increased viscosity Expired GB2032937B (en)

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GB7843274A GB2032937B (en) 1978-11-06 1978-11-06 Photosensitive resin compositions having increased viscosity

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Application Number Priority Date Filing Date Title
GB7843274A GB2032937B (en) 1978-11-06 1978-11-06 Photosensitive resin compositions having increased viscosity

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GB2032937A true GB2032937A (en) 1980-05-14
GB2032937B GB2032937B (en) 1982-10-20

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