Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
  • G03C1/00—Photosensitive materials
  • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
  • G03C1/7614—Cover layers; Backing layers; Base or auxiliary layers characterised by means for lubricating, for rendering anti-abrasive or for preventing adhesion
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
  • Y10S430/162—Protective or antiabrasion layer

Definitions

• the object of this invention is to provide a photographic light-sensitive material which is not sticky or adherant without substantially impairing its inherent photographic characteristics or causing objectionable side-effect during manufacture.
• This object has been accomplished by introducing on the surface layer of a photographic silver halide lightsensitive material a polymer containing as recurring units a monoester of an alipathic polyhydric alcohol withacrylic acid or methacrylic acid. 7
• a photographic material having at least one silver halide photosensitive emulsion layer on a support can be rendered non-sticky or non-adhesive by admixing with the non-photosensitive surface layer of the photographic material a homopolymer or copolymer of at least one monoester of an aliphatic polyhydric alcohol with either acrylic acid or methacrylic acid.
• non-photosensitive surface layer used herein includes a non-photosensitive surface layer which is provided on the emulsion layer side of the photographic light-sensitive material and a nonphotosensitive outer layer which is provided on the surface of the opposite side of the emulsion layer.
• a protective coating layer and a back coating layer of a photographic lightsensitive material, an intermediate layer, filter layer or like non-photosensitive layers of an intermediate product include a protective coating layer and a back coating layer of a photographic lightsensitive material, an intermediate layer, filter layer or like non-photosensitive layers of an intermediate product.
• the polymer used in this invention i.e., that contains as its recurring unit a monoester of an aliphatic polyhydric alcohol with acrylic acid or methacrylic acid, includes, for example, homopolymers, copolymers or graft copolymers of monomethacrylic acid esters or monoacrylic acid esters of an aliphatic polyhydric alcohol.
• esters examples include 2-hydroxyethyl methacrylate, 3-hydroxypropyl methacrylate, 2- hydroxypropyl methacrylate, '4-hydroxybutyl methacrylate, S-hydroxypentyl methacrylate, 2,2-dimethyl-3- hydroxypropyl methacrylate, diethylene glycol monomethacrylate, trimethylolpropane monomethacrylate, pentaerythritol monomethacrylate, 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 4-hydro'xybutyl acrylate,S-hydroxypentyl acrylate, 2,2-dimethyl-3-hydroxypropyl acrylate, diethylene glycol monoacrylate, trimethyl-olpropane monoacrylate and pentaerythritol monoacrylate, and the like.
• Preferred aliphatic polyhydric alcohols include those containing from 2 to 5 hydroxy gro ups and from 2 to about carbon atoms.
• the comonomers constituting other monomers to be copolyme'rized with the above monoesters can be any of the well known olefinic polymerizable monomers including the vinylic monomers and the diolefmic monomers.
• the vinylic monomers can include styrene or substituted styrenes, acrylic acid esters, methacrylic acid esters, vinyl ethers, vinyl ketones, vinylidene chloride, vinyl chloride, vinyl esters, acrylonitrile, substituted acrylonitriles, vinyl pyridines, acrylamides, allylamines, and similar well known vinylic monomers.
• the polymerizable diolefms such as l,3-butadiene, isoprene, chloroprene, 2,3-dimethyl-l ,3-butadiene and similar diolefinic monomers are suitable for use in practicing the invention.
• Typical monomers which can be employed in practicing the invention include ethyl acrylate, n-propyl acrylate, isopropyl acrylate, isobutyl acrylate, n-amyl acrylate, isoamyl acrylate, n-hexyl' acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, n-decylacrylate, B-cyanoethyl acrylate, B-chloroethyl acrylate, n-butyl acrylate,
• styrene p-methyl styrene, 2,4-dimethyl styrene, 2,5-dimethyl styrene, 3,4-dimethyl styrene, 3,5- dimethyl styrene, 2,4,5-trimethyl styrene, 2,4,6- trimethyl styrene, 2,4,5-triethylstyrene, o-ethylstyrene, n-ethylstyrene, p-ethylstyrene, 3,5-diethyl styrene, p-nbutyl styrene, m-sec-butyl styrene, m-tert-butyl styrene, p-hexyl styrene, pn-heptyl styrene, p-2- ethylhexyl styrene
• vinyl ketones such as methylvinyl ketone, ethylvinyl ke tone, and the like
• vinyl ethers such as methylvinyl ether and the like
• alkenyl esters such as isopropenyl acetate and the like
• similar well known polymerizable unsaturated monomers such as acrylic acid, allylamine, methacrylic acid, acrylamide, methacrylamide, N-alkyl acrylamides and N-alkyl methacrylamides containing from 1 to 12 carbon atoms in the alkyl group such as N-methyl acrylamede and N-methyl methacrylamide, N,N-dimethyl acrylamide, N,N-diethyl acrylamide, N-methylol acrylamide, N-hydroxyethyl acrylamide, N-tert-butyl acrylamide, N-cyclohexyl acrylamide, diaceton-acrylamide, N-(1,l-dimethyl-3-hydroxybutyl)
• the ratio ofmonomers in the copolymerization is not critical, but the proportion of monomethacrylate or monoacrylate of the aliphatic polyhydric alcohol in the copolymer is desirably in excess of 50 mol prefera-- bly more than about 60%.
• the comonomer can be used as a combination of two or more thereof.
• the molecular weight of the homopolymer or copolymer may be in general greater than 10,000, preferably about 50,000 to 500,000, which, however, is not critical.
• the graft polymers used in the present invention include polymers in which one or more monomers described above are grafted onto a parent polymer.
• the parent or base polymer of the graft copolymer used in the present invention is a hydrophilic polymeric material containing a functional group having active hydrogen such as an amino, imino, etc., group onto which the polymerizable monomer of the above described esters is grafted, with or without another copolymerizable monomer as described above.
• Suitable parent polymers include gelatin, acylated gelatin, polyvinyl alcohol, polyacrylamide, carboxymethyl cellulose, starch, hydroxyethyl cellulose and the like.
• acylated gelatins there can be employed the reaction product of gelatin with an organic acid anhydride or a chloride such as succinyl gelatin, phthalyl gelatin or acetyl gelatin.
• Such acylated gelatin is well known in the art, and the preparation thereof is described, e.g., in U.S. Pat. Nos. 2,525,753 and 2,691,582.
• the amount of the monomer or monomers grafted ranges from about 5 to 95% by weight of the total amount of starting materials subjected to reaction, with a preferred range being 10 to 60% by weight.
• the monomers it is desirable that at least 50% thereof be the monomethacrylate and/or methacrylate of the aliphatic'polyhydric alcohol and the ester should be contained in an amount of at least 5% of the total amount of starting materials.
• the ratio of monomer is 5% (lower limit)
• all should be the ester, while'if its 6%, 5% is ester and 1% can be another monomer.
• the method of polymerization by which the polymer of thisinvention is prepared is not limited to any particular one and involves conventional solution polymerization process, graft-polymerization proceses, etc.
• Synthesis Example 4 Synthesis of the copolymer of 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate According to the procedure of Synthesis Example 2, 94g of 2-hydroxyethyl acrylate and 106g of 2- hydroxyethyl methacrylate were copolymerized to give the indicated copolymer having a molecular weight of approximately 230,000 in a yield of 186g.
• Synthesis Example 5 Synthesis of the copolymer of 2-hydroxyethyl methacrylate and methyl methacrylate To a solvent mixture comprising 500 ml. of water and 1500 ml. of' methanol were added 419g of 2- hydroxyethyl methacrylate, 81g of methyl methacrylate and 1.5g of benzoyl perioxide. The resultant mixture was continuously stirred at 60C for 4 /2 hours under a nitrogen atmosphere. The resultantproduct was treated as in Synthesis Example 3 to give the indicated copolymerhaving a molecular weight of approximately 480,000 in a yield of 430g.
• Synthesis Example 6 Synthesis of the graft-copolymer of hydroxyethyl cellulose with 2-hydroxy diethyl methacrylate To a solvent mixture comprising 750 ml. of water and 150 ml. of ethanol was added 50g of hydroxyethyl cellulose (molecular weight of about 150,000) and dissolved at 60C. After flushing the system with nitrogen, the solution was further heated to a temperature of 75C, and thereafter 50g of 2-hydroxyethyl methacrylate containing 0.3g of benzoyl peroxide was added dropwise thereto from a dropping funnel under stirring for 4 hours. Reaction was under a nitrogen gas atmosphere. The reaction product was put in a dialysis film and subjected to dialysis for 20 hours by immersion in flowing water, and then freeze-dried to give the indicated copolymer in a yield of 88g.
• Synthesis Example 7 Synthesis of the graft-copolymer of gelatin with 2- hydroxyethyl methacrylate
• Twenty grams of photographic grade gelatin was dissolved at 60C in 100 ml. of a glycerin/water (1:1 by volume) mixture.
• 300 ml. of an ethanol/water (3:1 by volume) mixture was added slowly thereto, after which 20g of 2-hydroxyethyl methacrylate and lg of benzoyl peroxide were added over about 10 minutes.
• the resultant mixture was heated at 80C for 2 hours to effect polymerization. After cooling the reacted mixture to 60C and allowing it to stand for 20 minutes, the reacted mixture was poured into water to obtain a fibrous precipitate which was washed with water and dried to give the indicated graft-copolymer.
• solvents may be used to dissolve the polymer.
• solvents include water, methanol, ethanol, propanol, butanol, glycols,
• methyl cellusolve etc.
• solvents may be used, if desired, as a combination of two or more thereof.
• the polymer-containing coating solution may contain, if desired, a hydrophilic high molecular weight substance as is commonly used as a hydrophilic colloid or binder in the field of silver halide photographic materials, such as gelatin, gelatin derivatives, e.g., acylated gelatin such as those described hereinbefore as to the parent polymer, cellulose derivatives such as carboxymethyl cellulose, hydroxyethyl cellulose, et'c., polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylamide, starch, etc.
• a hydrophilic high molecular weight substance as is commonly used as a hydrophilic colloid or binder in the field of silver halide photographic materials
• gelatin gelatin derivatives, e.g., acylated gelatin such as those described hereinbefore as to the parent polymer
• cellulose derivatives such as carboxymethyl cellulose, hydroxyethyl cellulose, et'c.
• polyvinyl alcohol polyvinyl
• the coating solution may further contain other additives conventionally usedin the art, for example, a hardening agent such as an aldehyde hardening agent. a methylol hardening agent. a 1,4-dioxane hardening agent, an axiridine hardening agent, an iso-oxazole hardening agent, a carbodiimide hardening agent, an active halogen hardening agent or an active vinyl hardening agent (typical examples of such hardening agents are described in U.S. Pat. Nos. 3,232,764; 3,288,775;
• 2,336,327; 2,360,290; 2,403,721; 2,418,613; 2,704,713; 2,728,659; 2,732,300 and 2,735,765, 'a coating aid such as an anionic, cationic, nonionic or'ampholitic surface active agent, a surface-roughening agent or matting agent such as silica, strontium barium sulfate, etc., an antistatic agent and the like.
• the coating solution containing the. above polymer may be applied to the surface of the silver halidecontaining photo-sensitive material according to any known manner which has heretofore been employed in the production of photographic materials.
• Such coating methods include, for instance, dip coating, air-knife coating, curtain coating,extrusion coating and a simultaneous multi-layer coating process as described in U.S. Pat. Nos. 2,761,791 and 3,526,528 and British Patent No. 837,095.
• the support material'used in this invention to which the silver halide-containingphotographic emulsion is applied can be any of those knownin the art and is exemplified by cellulose esters, polyvinyl acetal, polyethylene terephthalate,polystyrene, baryta paper, polyethylene laminated paper, synthetic paper, etc.
• the silver halide-containing emulsion used in the photographic emulsion(s) of this invention contain, as a silver halide, for example, silver chloride, silver bromide, silver iodobromide, silver chlorobromide, silver iodochlorobromide and like crystalline mixtures of two or more thereof, which are conventionally prepared and optionally chemically sensitized according to widely known methods.
• a silver halide for example, silver chloride, silver bromide, silver iodobromide, silver chlorobromide, silver iodochlorobromide and like crystalline mixtures of two or more thereof, which are conventionally prepared and optionally chemically sensitized according to widely known methods.
• the above emulsion can be a single or multicomponent vmixture. While photographic additives other than the' above are not necessary,-in commercial practice terme as arecommonly used in the artto improve the ease of coating, storability or handling characteristics of the emulsion will commonly be added to in an amount as is used by the art, for example, such as a spectral sensitizer, stabilizer, fog inhibitor, color coupler, polyalkylene oxide, gelatin plasticizer, vinyl polymerlatex, hardener, coating aid, etc. Needless to say, these components are not mandatory and the present invention should not be construed as requiring the presence of such components, though practically speaking theywill generally be used in commercial size operations.
• the use of gelatin as a main component is generally preferred.
• the emulsion layer may contain other materials such as gelatin derivatives such as acylated gelatin described hereinbefore as to the parent polymer, cellulose derivatives such as carboxymethyl cellulose, hydroxyethyl cellulose, etc., polysaccharide,-synthetic high molecular weight substance (e.g., polyvinyl alcohol, poyvinyl pyrrolidone), and thelike.
• the photosensitive material of this invention is characterized by having at least one surface layer formed of or containing at least one of the above polymers, it is possible, of course, to add and use any other known components or any other conventional techniques without departing from the essential spirit of this invention.
• Adhering or sticking problems which previously unavoidably took place whenever the coated surface layer is put together in tight contact with other surfaces under an atmosphere of high humidity, e.g under a relative humidity as high or more than 65%, have now been obviated to a great extent in accordance with this invention, in which the surface layer of a photographic material is provided with a coating layer consisting of or containing the above-described polymer.
• the surface treatment of this invention using the above polymer can be combined, if desired,-with any other known stickiness-reducing treatment which has been proposed up to now, e.g., a surface-coarsening process and the addition of a specific type of. surface active agent as described previously. In this case, a corresponding additional effect is generally obtained.
• the non-photosensitive layer containing the specific polymer of this invention exhibits a superior stickproofing or non-tacky property whenever it is formed on a complete product or on an intermediate product, and effectively prevents the photographic materials during their production or handling from problems invited by the adhesive or tacky surface thereof.
• the protective layer of the present invention is, essentially speaking, either the topmost layer on the emulsion side of the film and/or the topmost layer on the rear side of the film, in a final product.
• the protective layer When used for an intermediate product, generally the protective layer will be anintermediate layer in the final product. Therefore, inorder to secure a low adhesion surface in a final product, it will be obvious the surface layer in the final product must contain the polymer.
• the use in an intermediatelayer per se is not, however, excluded from the present invention where the main adhesion problem is encountered with the intermediate product.
• the thickness of the layer containing the polymer of the invention is less important than the-proportion of the polymer present. Generally speaking, however, considering the handling of photographic elements and the fact they are sometimes subjected to rough handling, itis preferred that the minimum thickness of the layer containing the polymer of the present invention, be it present alone or in mixture form with another substance, be about O.3 micron, and it is more preferred that the thickness be at least 0.5 micron. No significant improvement is obtained by'using a layer greater than 3 microns thick, and accordingly it is particularly pre: ferred to use a layer of from 0.5 to 3 microns in thickness.
• test films A and B (yunine coupler having the following formula 0 ONHCmHu dried thickness of 1.5 ,u. to thereby prepare test films A and B, respectively.
• test films A and B were each cut into fragments each having an area ofa square cm on a side, each surface of which was brought into tight contact with the rear face of a cellulose triacetate base while imposing a pressing load of 3 Kg and allowed to stand under a relative humidity (RH) of 85% at a temperature of 40C over a period of 3 days and 6 days. Thereafter, the pressed film was stripped from the cellulose triacetate base, and the condition of the film sur- I face was examined. The surface of the film which had been closely attached to the base by being tightly contacted and adhered thereto had a rather smooth and glossy appearance to such an extent that it could not be clearly distinguished from other parts where no tight adhesion took place. The proportion of such glossy area to the total surface area in'percent was taken to evaluate the effectiveness of the top coating of this invention containing the specific polymer. The results are given in Table 1 below.
• the tendency of surface tackiness or adhesiveness can be conveniently evaluated by comparing the size of the glossy area, i.e., the larger the percent of glossy area the greater the adhesion.
• film B of this invention which is a photosensitive material having a surface layercontaining poly-Z-hydroxyethyl methacrylate has a more reduced surface tackiness than film A prepared according to a known method.
• This type of film is usually formed as an intermediate product during the course of manufacturing multilayered color photographic materials, so that adherance problems which often take place during the hairdling thereof can be efficiently overcome by providing a surface layer containing a specific polymer of this invention, as seen in the case of test film B.
• Example 2 Test film A prepared in Example 1 was coated in a 6 LII that used in Example I as the red-sensitive-layer with 150g of a 0.1% methanol solution of a spectral sensitizer represented by the following formula 2H5 iHa 50g of a 1% aqueous solution of 5-methyl-7-hydroxy- 2,3,4-triazaindolidine, 600g of a magneta coupler dispersion having the following recipe and 20g of a 2% aqueous solution of 2,4-dichloro-6-hydroxy-S-triazine sodium salt.
• a green sensitive emulsion layer was formed.
• Magenta coupler dispersion Aqueous gelatin solution (10%) lOOOg Aqueous sodium dodecylbenzene sulfonate solution (5%) g Magenta coupler 100g Ethyl acetate 200g ibutyl phthalate l20g Magenta coupler having the following chemical formula:
• a 5% aqueous gelatin solution containing yellow colloidal silver was applied in a dried thickness of l'.5 u so as to form a yellow filter layer.
• a blue-sensitive emulsion layer was formed by coating the resultant film with a layer of a dried thickness of 6 p. with a coating liquid prepared by adding to l000g of a gelatin-based silver iodobromide photographic emulsion [containing 6 mol silver iodide (comprising 10% silver-halide, 12% gelatin and 78% water); having an average particle diameter of 1.2 ,u] 20g of a 1% aqueous solution of 5-methyl-7-hydroxy- 2,3,4-triazaindolidine, 500g of a yellow coupler dispersion having the following recipe and 20g of a 2% aqueous solution of 2,4-dichloro-6-hydroxy-S-triazine sodium salt.
• a gelatin-based silver iodobromide photographic emulsion [containing 6 mol silver iodide (comprising 10% silver-halide, 12% gelatin and 78% water); having an average particle diameter of 1.2 ,u]
• Test films C, D and E were each' subjected to a sticking test in the same manner as employed in Example 1.
• Test film D having the surface layer according to this invention exhibited a remarkably improved resistance to-sticking or lack of adhesiveness as compared to test films C and D which had been coated with a liquid containing no specific polymer. 1
• EXAMPLE 3 A conventionally undercoated polyethylene terephthalate base was coated to a dried thickness of 10 1.4. with a coating solution prepared by admixing 1000g of the same silver halide emulsion .used in the blue C5Hu Film Composition V F Bone gelatin G Poly(2-hydroxyethyl methacrylate/hydroxyethyl acrylatc)* Bone gelatin containing 5% of globular particles of polymothyl methacrylatc(average particle size of 2 p.) v
• Test film G having a surface layer according to this invention exhibited an excellent antirsticking property compared to known films F, H, l and J.'After developing these films, film l-l lost its original transparency, whereas film G of this invention remained transparent.
• EXAMPLE 4 g A conventionally undercoated cellulose triacetate base was coated to a dried thickness of 14 p. with a coating liquid prepared by mixing 1000g of a gelatinbase silver iodobromide photographic emulsion [comprising 7% silver halide, 6% gelatin and 87% water; containing 5 mol silver iodide and having an average particle size of 0.70 ,u] with 5g of a 0.1% methanol solution of l,l-diethyl-2,2-cyanine chloride, 40g of a 0.1% methanol solution of 3,3-diethyl-9-methylthiacarbocyanine bromide, 50g of a 1% aqueous solution of 5-methyl-7-hydroxy-2,3,4-triazaindolidine, 400g of a polyethyl acrylate latex having a particle size of 0.2 a, 5g ofa 5% aqueous solution of sodium lauryl sulfate and 20g of a
• AMP 5 Using the same silver halide emulsion as employed in Example 3, a conventionally undercoated cellulose triacetate base was coated with protective coating liquid N or P according to the simultaneous twot-layer coating.
• EXAMPLE 6 The surface of a biaxially stretched, crystallized polyethylene terephthalate film was coated with a solution having the following recipe and dried at 120C for 10 minutes to provide a back layer of a dried film thick ness of 0.5 a, which was called film Q.
• the back face of the resultant film was further coated with the following composition which was dried at 120C for 10 minutes to form a surface layer of a film thickness of 0.2 p. to provide film R.
• film R having a backing layer containing a specific polymer according to this invention has a markedly improved anti-sticking property compared to film Q containing no polymer.
• the advantageous effect of this invention is also attained by admixing the specific polymer with a backing layer of a photosensitive material.
• EXAMPLE 7 To l000g of a gelatino silver iodobromide photographic emulsion containing 1.5 mol silver iodide (the emulsion comprised 14% silver halide, 3.8% gelatin and 82.2% water, the silver halide having an average particle size of 1.4 p.) and sensitized with sodium thiosulfate and sodium tetrachloroaurate there were added 44g of a 1% aqueous solution of -methyl-7-hydroxy- Coating solution S 1 Aqueous bone gelatin solution (6.5%)
• films S and T were cut into 2 square pieces 4 cm. on a side and stored for 2 days at lC, 90% RH, and then protective layers of the film S samples were contacted with each other and the protective layers of the film T samples were contacted with each other and all samples stored for 2 days at 35C, 90% RH.
• the films were stripped off and the surfaces observed as in Example 1.
• Table 7 Film T, a photographic material having the surface layer according to this invention, exhibited a remarkably improved resictance to sticking, as compared to comparative photographic material Film S. Further, film T had the changes and modifications can be made therein without departing from the spirit and scope thereof.
• a photographic silver halide-containing lightsensitive material characterized by having at least one non-photosensitive surface layer containing at least one polymer containing as its recurringunit at least one monoester of an aliphatic polyhydric alcohol with acrylic acid or methacrylic acid.
• a material as claimed in claim 1 wherein the polymer is a copolymer.
• yhydric alcohol and the ester being contained in an amount of at least 5% by. weight.
• nonphotosensitive surface layer consists essentially of said at least one polymer.
• nonphotosensitive surface layer comprises said at least one polymer plus a different polymer.
• non-photosensitive surface layer comprises at least 10% by weight of said at least one polymer.
• a material as claimed in claim 11 wherein said non-photosensitive surface comprises at least 20% of said at least one polymer.
• a material as claimed in claim 13 wherein the thickness of said non-photosensitive surface layer is from 0.5 to 3 microns.
• a material as claimed in claim 15 wherein said olefinic polymerizable monomer is a vinylic monomer or a diolefinic' monomer.
• ester is selected from the group consisting of 2- hydroxyethyl methacrylate, 3-hydroxypropyl methacrylate, 2-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, S-hydroxypentyl methacrylate, 2,2-dimethyl-3-hydroxypropyl methacrylate, diethylene glycol monomethacrylate, trimethylolpropane monomethacrylate, pentaer thritol monomethacrylate, Z-hydroxyethyl acrylate, 3- ydroxypropyl acrylate, 2- hydroxypropyl acrylate, 4-hydroxybutyl acrylate, 5- hydroxypentyl acrylate, 2,2-dimethyl-3-hydroxypropyl acrylate,.diethylene glycol monoacrylate, trimethylolpropane monoacrylate and pentaerythritol monoacrylate.

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• 1972
  • 1972-06-15 JP JP47059743A patent/JPS5127534B2/ja not_active Expired
• 1973
  • 1973-06-14 FR FR7321601A patent/FR2189773B1/fr not_active Expired
  • 1973-06-14 CA CA174,020A patent/CA1006037A/en not_active Expired
  • 1973-06-15 GB GB2870273A patent/GB1384967A/en not_active Expired
  • 1973-06-15 DE DE2330573A patent/DE2330573A1/de active Pending
  • 1973-06-15 US US00370571A patent/US3840371A/en not_active Expired - Lifetime

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