GB2127167A - Water developable light sensitive compositions and printing plates - Google Patents
Water developable light sensitive compositions and printing plates Download PDFInfo
- Publication number
- GB2127167A GB2127167A GB08325083A GB8325083A GB2127167A GB 2127167 A GB2127167 A GB 2127167A GB 08325083 A GB08325083 A GB 08325083A GB 8325083 A GB8325083 A GB 8325083A GB 2127167 A GB2127167 A GB 2127167A
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- United Kingdom
- Prior art keywords
- water
- composition according
- insoluble polymer
- nonionic
- light sensitive
- 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.)
- Granted
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims description 30
- 125000002091 cationic group Chemical group 0.000 claims abstract description 14
- 229920003176 water-insoluble polymer Polymers 0.000 claims abstract description 14
- 238000000576 coating method Methods 0.000 claims abstract description 9
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 239000011248 coating agent Substances 0.000 claims abstract description 8
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000006185 dispersion Substances 0.000 claims abstract description 6
- 229920000126 latex Polymers 0.000 claims abstract description 4
- 239000004816 latex Substances 0.000 claims abstract 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 2
- 229920000642 polymer Polymers 0.000 claims description 20
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 239000008199 coating composition Substances 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012875 nonionic emulsifier Substances 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 5
- 239000000839 emulsion Substances 0.000 description 18
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- USSFUVKEHXDAPM-UHFFFAOYSA-N Nicotinamide N-oxide Chemical compound NC(=O)C1=CC=C[N+]([O-])=C1 USSFUVKEHXDAPM-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000000129 anionic group 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
- 229960004279 formaldehyde Drugs 0.000 description 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 2
- 231100000489 sensitizer Toxicity 0.000 description 2
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical class OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- YHQDZJICGQWFHK-UHFFFAOYSA-N 4-nitroquinoline N-oxide Chemical compound C1=CC=C2C([N+](=O)[O-])=CC=[N+]([O-])C2=C1 YHQDZJICGQWFHK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- PLXMOAALOJOTIY-FPTXNFDTSA-N Aesculin Natural products OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]1Oc2cc3C=CC(=O)Oc3cc2O PLXMOAALOJOTIY-FPTXNFDTSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GIIWGCBLYNDKBO-UHFFFAOYSA-N Quinoline 1-oxide Chemical compound C1=CC=C2[N+]([O-])=CC=CC2=C1 GIIWGCBLYNDKBO-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- -1 amine salts Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005410 aryl sulfonium group Chemical group 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- DWCZIOOZPIDHAB-UHFFFAOYSA-L methyl green Chemical compound [Cl-].[Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)[N+](C)(C)C)=C1C=CC(=[N+](C)C)C=C1 DWCZIOOZPIDHAB-UHFFFAOYSA-L 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- G03F7/016—Diazonium salts or compounds
- G03F7/021—Macromolecular diazonium compounds; Macromolecular additives, e.g. binders
- G03F7/0212—Macromolecular diazonium compounds; Macromolecular additives, e.g. binders characterised by the polymeric binder or the macromolecular additives other than the diazo resins or the polymeric diazonium compounds
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Abstract
A water developable printing plate is provided with a photopolymerisable coating formed from a latex comprising a water-soluble diazopolymer reaction product of a diazoaryl amine and an aldehyde and an aqueous cationic or nonionic dispersion of a water- insoluble polymer. The inclusion of a water miscible organic solvent improves the shelf-life of the photopolymerisable system and the printing plate especially under high humidity conditions.
Description
SPECIFICATION
Water developable, light sensitive, compositions and printing plates
This invention relates to photopolymerisable systems which include photopolymerisable compositions that are light sensitive latices which form water developable printing plates when coated on suitable backing members. Selected image areas can be insolubilised and cross linked by exposure to actinic radiation and the composition in the non-radiated non-image areas can be washed away with water to provide the desired planographic image.
Emulsion photopolymerisable systems are taught in US Patents 4 186069,4224398, and 4 288 520. In these systems, the photopolymerisable coating is an emulsion mixture of a polymer component having water insoluble polymer particulates within an aqueous suspension medium, together with a water soluble or water dispersible light-sensitive component including a polymer having at least two moieties per molecule. Such polymers are sensitive to actinic radiation, and by generating a free radical or other cross linking species form a matrix of crosslinked polymer which encapsulate or entrap therein and disperse therethrough the water insoluble polymer. Prior to curing this system is a three phase emulsion including the water insoluble polymer particulates within the aqueous suspension medium with which is also mixed the light-sensitive polymer.When the coating composition is applied to a suitable backing member, the aqueous suspension is substantially removed to realise a two-phase mixture of the polymer particulates and light sensitive polymer.
It has long been known to use water insoluble polymers in producing light sensitive coatings for use on substrates such as planographic printing plates in which the polymers are incorporated as part of a solvent system layer which uses organic materials and which must be driven off from the plate, a requirementwhich is time and energy consuming, wasteful of solvents and possibly hazardous to the operator and the environment.
Use of water soluble systems generally avoids the disadvantages of the organic base systems, but they are not particularly long lasting because the polymers are water soluble and are therefore subject to erosion of the image area when in use and/or through the action of atmospheric moisture. The emulsion systems of the aforementioned patents provide an improved stability with respect to other water based systems, but they are still characterised by a shelf-life which is less than optimum, especially under high humidity conditions. Additionally, the images provided by such emulsion systems often include spots which are commercially unacceptable.
It is our object to provide a photopolymerisable system and a water developable printing plate which exhibits improved properties, particularly with respecs to shelf life under high humidity conditions.
A light sensitive coating composition according to the invention comprises a water soluble diazo polymer reaction product of a diazoarylamine and an aldehyde and an aqueous cationic or nonionic dispersion of a water insoluble polymer.
The invention also includes presensitised printing plates comprising a substrate carrying a coating of this composition, and printing plates comprising a substrate carrying such a coating and which has been cured in preselected areas.
The light sensitive coating composition of the present invention is an emulsion mixture of a cationic or nonionic polar emulsion component having water insoluble polymer particulates within an aqueous suspension medium together with a water soluble or water dispersible component which is a diazo polymer reaction product of a diazoarylamine and an aldehyde. The water insoluble polymer emulsion component and the light sensitive component are generally present in quantities of the same order of magnitude but can vary from a weight percent ratio of about 25:1 to 1:25, preferably about 5:1 to 1:5.
The water soluble diazo polymers used in the present invention are prepared by the well known condensation reaction of a diazoaryl amine such as a p-diazodiphenylamine and an aldehyde such as formaldehyde or paraformaldehyde which results in the formation of an oligomer or low molecular weight polymer. Many such diazo polymers are commercially available and typical examples include
Diazo-8000 sold by Polychrome Corporation of Yonkers, New York, which is a zinc chloride salt of the reaction product of para-diazodiphenylamine with paraformaldehyde, and Diazo Resin No 4 of Fairmount Chemicals, which is a reaction product of para-diphenylamine diazonium chloride with formal- dehyde. Salts of the reaction product of pdiazodiphenylamine with paraformaldehyde are especially preferred.Zinc chloride, phosphate, sulfate salts and the like can be utilised, the zinc chloride salts being preferred.
The aqueous dispersion of the water insoluble polymer of the present invention is cationic or nonionic either as a result of the use of an emulsifier or by having the cationic or nonionic group linked to the polymer. The water insoluble polymer is preferably a solid particulate having a size in the range of about 100 Angstroms to 10 microns in diameter. In general, any polymer which carries a cationic or nonionic group orwhich can be formulated into an emulsion using a cationic or nonionic emulsifier can be employed in the present invention.Suitable polymers include the homopolymers and copolymers of styrene, ethyl acrylate, butyl acrylate, ethyl methacrylate, butyl methacrylate, vinyl acetate, vinyl chloride, vinylidene chloride, butadiene, methylstyrene, vinyl toluene, dimethylaminoethyl acrylate, acrylic acid, methacrylic acid, isoprene, chloroprene, maleic anhydride, ethylene glycol acrylates such as polyethylene glycol acrylate, halogenated vinyl aromatics such as chlorostyrene and bromostyrene, methylvinyl ether, vinyl pyrrolidone, polyurethane and the like.
Among the cationic and nonionic emulsifiers which can be used in the present invention are ammonium salts of substituted amines containing alkyl and/or aryl groups attached to the nitrogen, alkyl or aryl sulfonium salts, alkyl and alkyl-aryl polyethers, cationic or nonionic fluorosurfactants and polyoles.
Various cationic and nonionic emulsions are com merciaily available and can be used in the practice of the present invention. For example, Witcobond
W-212, a cationomeric polyurethane emulsion sold by Witco can be used in the present invention.
Reference should be made to US Patents 3 873484 and 4 160 065 which describe such emulsions. A typical nonionic emulsion is Vondic 131 OF sold by
Dainippon Inc., which is available as a polyurethane emulsion. Witcobond and Vondic are trade marks.
When it is desired to enhance the sensitivity of the light sensitive diazo polymer, known sensitisers can be included in the composition. For example, the composition can contain Michler's ketone, benzoin, benzoin methyl ether and other well known sensitisers which may be water solubilised as required by the use of amines, amine salts, quaternary amines, or polyalkoxy groups.
The light sensitive composition of the present invention generally contains stabilisers which are derivatives of pyridine-N-oxide or other quaternised ammonium compounds. Typical examples include nicotinamide-N-oxide, pyridine-N-oxide, quinoline
N-oxide, 4-nitroquinoline-N-oxide, tetra-methyl ammonium chloride, dimethyldiallyl ammonium chloride. These stabilisers are present at a weight percent ratio range of from about 1:50 to 2:1, preferably 1 :10 to 1:1, relative to the light sensitive diazo polymers.
The compositions of the present invention can also include antihalation agents, dyes, pigments, fillers, plasticisers, extenders, crosslinked particles, and other materials for aiding in maintaining or modifying the viscosity, plasticity and/or stability of the compositions. It will be appreciated that any dues should be water soluble cationic or nonionic dyes although anionic dyes having at most one anionic group can also be used.
It has been found that the inclusion of a water miscible organic solvent in the aqueous dispersion of the water insoluble polymer improves the shelf life of the composition especially under high humidity conditions. Typical organic solvents which can be used include methanol, ethanol, acetone, dimethylformamide, methylcellosolve, acetonitrile, dioxane, propanol, etc. The water miscible organic solvent will generally be about 0.1 -75 weight percent, preferably about 1 to 40 weight percent, based on the weight of the total solvent system.
The photosensitive compositions of the present invention can be applied to any conventional substrate such as aluminium, copper, zinc, magnesium, steel or plastic, in any convenient fashion such as spray, roll or dip methods. After coating, the aqueous phase is evaporated or dried to remove the water or water and miscible organic solvent at low or elevated temperatures with or without imposition of a vacuum to leave the water insoluble emulsion and light sensitive polymer together with a small amount of residual water or water and miscible organic solvent on the substrate. Areas of the composition which are exposed to actinic radiation harden abd become hydrophobic, while the portions which are not so exposed remain water receptive and can be removed by simple water development.
In order to further illustrate the invention, various examples are set forth below. Throughout these examples, as well as throughout this specification and claims, all parts and percentages are by weight and all temperatures in degrees Centigrade unless otherwise specified.
Example 1
A photopolymerisable composition was prepared by mixing 5.37 percent of a cationomeric polyurethane emulsion (Witcobond W-212) and 0.64 percent of a water soluble diazopolymer which was the zinc chloride salt of a reaction product of para-diazodiphenylamine and paraformaldehyde.
The composition additionally contained 0.16 percent zinc chloride, 0.48 percent tris(2chloroethyl)phosphate, 0.16 percent nicotinamide
N-oxide, 0.032 percent methyl green, 76.6 percent water and 16.5 percent dimethylformamide. The photosensitive composition was coated on a grained anodised and silicated sheet of aluminium and allowed to dry. The plate was thereafter exposed to ultraviolet radiation, developed with tap water and gummed in the conventional fashion. The resulting lithographic plate was found to produce 30,000 good quality copies. A sample of the resultant plate with a coating weight of 0.75g/m2 was subjected to accelerated shelf-life testing under high humidity conditions by exposure to 90 percent humidity at 380C for 120h. The plate showed quite satisfactory properties in exposure speed, adhesion and development.
Another sample subjected to accelerated shelf-life testing at 600C and low humidity for 120h also performed satisfactorily.
Example 11 The substrate used in the previous example was coated with an emulsion containing 4.09 percent of a nonionic polyurethane emulsion (Vondic 1310F,
Dainippin Inc.) and 0.66 percent of the same diazopolymer used in Example 1. The composition additionally contained 0.16 percent zinc chloride, 0.49% tris(2-chloroethyl)-phosphate, 0.16 percent nicotina mide-N-oxide, 0.25% Surfynol SE (Air Products Inc), 0.04 percent Zonyl FSC (du Pont), 77.8 percent water and 16.4% 2-methoxyethanol (methylCellosolve).
The composition was ubjected to the same accelerated shelf life as in Example 1 without any negative effects. Vondic Surfynol, Zonyl and Cellosolve are trade marks.
Claims (10)
1. A light-sensitive latex coating composition comprising a water soluble diazo polymer reaction product of a diazoarylamine and an aldehyde and an aqueous cationic or nonionic dispersion of a water insoluble polymer.
2. A composition according to claim 1 in which the aqueous cationic or nonionic dispersion contains a water miscible organic solvent.
3. A composition according to claim 1 or claim 2, and which contains a quaternary nitrogen containing stabiliser.
4. A composition according to any preceding claim and which contains a compatible dye.
5. A composition according to any preceding claim and which additionally contains a zinc salt.
6. A composition according to any preceding claim wherein the water insoluble polymer is dispersed in a cationic emulsifier.
7. A composition according to any of claims 1 to 5, wherein the water insoluble polymer is dispersed in a nonionic emulsifier.
8. A composition according to claim 1, substantially as herein described with reference to either of the Examples.
9. A presensitised printing plate comprising a substrate carrying a light-sensitive latex coating of a composition according to any preceding claim.
10. A printing plate comprising a substrate carrying a coating of a composition according to any of claims 1 to 8 and which has been cured on preselected areas thereof.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42075482A | 1982-09-21 | 1982-09-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8325083D0 GB8325083D0 (en) | 1983-10-19 |
| GB2127167A true GB2127167A (en) | 1984-04-04 |
| GB2127167B GB2127167B (en) | 1986-03-05 |
Family
ID=23667708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08325083A Expired GB2127167B (en) | 1982-09-21 | 1983-09-20 | Water developable light sensitive compositions and printing plates |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS59146049A (en) |
| CA (1) | CA1208473A (en) |
| DE (1) | DE3328019A1 (en) |
| FR (1) | FR2533227B1 (en) |
| GB (1) | GB2127167B (en) |
| NL (1) | NL8303171A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4430680A1 (en) | 1994-08-29 | 1996-03-07 | Hoechst Ag | Photosensitive mixture |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1517961A (en) * | 1975-05-20 | 1978-07-19 | Nippon Paint Co Ltd | Photosensitive composition and process for preparing same |
| GB2007379A (en) * | 1977-10-11 | 1979-05-16 | Eastman Kodak Co | Light sensitive diazo resin compositions for producing dye images |
| GB2013918A (en) * | 1978-01-30 | 1979-08-15 | Richardson Co | Photopolymerizable latex systems |
| GB2075702A (en) * | 1980-05-09 | 1981-11-18 | Fuji Photo Film Co Ltd | Photosensitive printing plate precursor |
| EP0048160A1 (en) * | 1980-09-15 | 1982-03-24 | Napp Systems (Usa) Inc. | Photosensitive recording material, and method of half-tone etching |
| EP0008038B1 (en) * | 1978-08-03 | 1983-05-18 | Hoechst Aktiengesellschaft | Process for the preparation of a light-sensitive copying material based on condensation products of diazonium salts |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1447954C3 (en) * | 1960-08-05 | 1975-11-06 | Hoechst Ag, 6000 Frankfurt | Presensitized planographic printing plate |
| US3382069A (en) * | 1964-06-18 | 1968-05-07 | Azoplate Corp | Planographic printing plate |
| DD96345A1 (en) * | 1972-01-05 | 1973-03-12 | ||
| GB1523762A (en) * | 1975-02-25 | 1978-09-06 | Oce Van Der Grinten Nv | Photocopying materials |
| CA1091969A (en) * | 1975-06-19 | 1980-12-23 | Robert W. Hallman | Photosensitive unilayer film structure cast from a polymeric emulsion dispersion |
-
1983
- 1983-08-03 DE DE19833328019 patent/DE3328019A1/en not_active Ceased
- 1983-09-07 CA CA000436187A patent/CA1208473A/en not_active Expired
- 1983-09-14 NL NL8303171A patent/NL8303171A/en not_active Application Discontinuation
- 1983-09-20 GB GB08325083A patent/GB2127167B/en not_active Expired
- 1983-09-21 JP JP17516683A patent/JPS59146049A/en active Pending
- 1983-09-21 FR FR8315005A patent/FR2533227B1/en not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1517961A (en) * | 1975-05-20 | 1978-07-19 | Nippon Paint Co Ltd | Photosensitive composition and process for preparing same |
| GB2007379A (en) * | 1977-10-11 | 1979-05-16 | Eastman Kodak Co | Light sensitive diazo resin compositions for producing dye images |
| GB2013918A (en) * | 1978-01-30 | 1979-08-15 | Richardson Co | Photopolymerizable latex systems |
| EP0008038B1 (en) * | 1978-08-03 | 1983-05-18 | Hoechst Aktiengesellschaft | Process for the preparation of a light-sensitive copying material based on condensation products of diazonium salts |
| GB2075702A (en) * | 1980-05-09 | 1981-11-18 | Fuji Photo Film Co Ltd | Photosensitive printing plate precursor |
| EP0048160A1 (en) * | 1980-09-15 | 1982-03-24 | Napp Systems (Usa) Inc. | Photosensitive recording material, and method of half-tone etching |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2127167B (en) | 1986-03-05 |
| DE3328019A1 (en) | 1984-03-22 |
| GB8325083D0 (en) | 1983-10-19 |
| JPS59146049A (en) | 1984-08-21 |
| NL8303171A (en) | 1984-04-16 |
| CA1208473A (en) | 1986-07-29 |
| FR2533227A1 (en) | 1984-03-23 |
| FR2533227B1 (en) | 1986-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |