WO1981000569A1 - A polymerizable water-based composition - Google Patents

A polymerizable water-based composition Download PDF

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Publication number
WO1981000569A1
WO1981000569A1 PCT/AU1980/000056 AU8000056W WO8100569A1 WO 1981000569 A1 WO1981000569 A1 WO 1981000569A1 AU 8000056 W AU8000056 W AU 8000056W WO 8100569 A1 WO8100569 A1 WO 8100569A1
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WO
WIPO (PCT)
Prior art keywords
composition
water
monomer
radiation
curing
Prior art date
Application number
PCT/AU1980/000056
Other languages
English (en)
French (fr)
Inventor
K Jones
K Jarrett
Original Assignee
Staybond Pty Ltd
K Jones
K Jarrett
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Staybond Pty Ltd, K Jones, K Jarrett filed Critical Staybond Pty Ltd
Priority to DE803049830T priority Critical patent/DE3049830T1/de
Publication of WO1981000569A1 publication Critical patent/WO1981000569A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/06—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent

Definitions

  • the present invention relates to water-based compositions, and methods of operation using the water-based compositions. Whilst initially developed in relation to inks and related printing methods, the composition and method of the invention have been found to be equally efficacious in other coating, and in binding, environments.
  • compositions which form a film or lattice as the carrier therefor evapor ⁇ ates consist of compositions which form a film or lattice as the carrier therefor evapor ⁇ ates.
  • These compositions generally comprise inert dispersed solids or soluble substances of desired properties, which properties are obtained on evaporation.
  • these properties viz. film hardness, gloss, adhesion
  • these properties must be achieved rapidly in order for the substrate to withstand high substrate velocity through the press.
  • enormous quantities of energy are required to be expended and "fast" organic solvents.are used, thereby introducing fire hazard and pollution problems.
  • water-based inks as a substitute for solvent- based products is not novel per se. Hitherto, such water- based inks were in the form of dispersion polymers. However, while water-based inks had potential advantages over solvent- based inks - such as cost savings, elimination of fire hazard, reduction in air pollution and more importantly the absence of a hydrocarbon base (hydrocarbons being subject to increas- ing shortages and subsequent price rises) - they also had numerous disadvantages such as difficulties with pigment dispersion, gloss, film thickness, curing time and flow characteristics which difficulties resulted in aqueous inks
  • the present invention relates to water-based compositions, and methods of operation using the water-based compositions. Whilst initially developed in relation to inks and related printing methods, the composition and method of the invention have been found to be equally efficacious in other coating/ and in binding , environments.
  • compositions which form a film or lattice as the carrier therefor evapor ⁇ ates consist of compositions which form a film or lattice as the carrier therefor evapor ⁇ ates.
  • These compositions generally comprise inert dispersed solids or soluble substances of desired properties, which properties are obtained on evaporation.
  • these properties viz. film hardness, gloss, adhesion
  • these properties must be achieved rapidly in order for the substrate to withstand high substrate velocity through the press.
  • enormous quantities of energy are required to be expended and "fast" organic solvents are used, thereby introducing fire hazard and pollution problems.
  • water-based inks as a substitute for solvent- based products is not novel per se. Hitherto, such water- based inks were in the form of dispersion polymers.
  • water-based inks had potential advantages over solvent- based inks - such as cost savings, elimination of fire hazard, reduction in air pollution and more importantly the absence of a hydrocarbon base (hydrocarbons being subject to increas- ing shortages and subsequent price rises) - they also had numerous disadvantages such as difficulties with pigment dispersion, gloss, film thickness, curing time and flow characteristics which difficulties resulted in aqueous inks based on dispersion polymers not being attractive.
  • the principal object of the invention is seen as the provision of a water-based ink which obviates the disadvantages inherent in prior art aqueous inks as indicated above (without resurrecting the disadvan ⁇ tages associated with solvent-based inks) and which, at the same time, is inexpensive, easy to apply, and devoid of toxicity.
  • Further objects include the provision of other water-based coating and binding compositions which (as our research developed) were found to be (i) superior to such compositions of the prior art, and (ii) within the ambit of our inventive concept. These will be elaborated hereafter.
  • the invention provides a polymerizable water-based composition
  • a polymerizable water-based composition comprising a primary component and an aqueous monomer system, wherein the said system comprises at least one water-soluble or water-miscible (or -dispersible) monomer; the composition being curable by radiation or otherwise.
  • a reactive monomer is used which is soluble in a very economical carrier viz. water.
  • the water carrier imparts a fluidic mobility to the compo ⁇ sition. It is not necessary for this carrier to be removed by evaporation for the composition to attain its desired physical properties.
  • the composition may be cured to a solid polymer, with carrier (or proportion thereof) in situ, by the application of radiation.
  • the radiation may be of any type (.e.g. heat, U.V., I.R., electron beam, gamma and other radiations) which is able to initiate and sustain polymerizatio
  • the expression primary component is defined- by refer ⁇ ence to the aspects of the invention in which the compositi and related methods, are applied.
  • t component may include pigments, or dyestuffs or like coatin compounds / supplemented (or partially or wholly replaced as appropriate) by non-reactive water borne components.
  • it may be an appropriate filler (the invention having application as a binder for various solids - and also as a foa able preparation) .
  • the present invention firstly provides a method of coating on a suitable substrate.
  • this method comprises the steps of applying the above-defined polymerizable water-based composition to a said substrate; and subjecting the so applied composition t curing (e.g. by exposure to heat, U.V., I.R., electron beam gamma or other radiation) , whereby the aqueous monomer syste reacts to form a hydrophobic polymer (the water present being rapidly lost e.g. by being absorbed into the substrat and/or by evaporation) .
  • the invention provides a method of binding or foaming.
  • t method comprises the steps of mixing the aforesaid aqueous monomer system with the appropriate primary component, and catalyst as and if required, and subjecting the resultant
  • the low viscosity composition in addition to the aqueous monomer system and the appropriate coating (e.g. pigment, dyestuff et al) component - will invariably contain a said catalyst to promote curing, and may also contain one or more of the said non-reactive water borne components (such as emulsions, dispersed or dissolved resins, polymers, and the like) .
  • the composition will generally be formulated in the light of such factors as the type of coating required and the type of radiation to be employed. For example, when curing is carried out by means of electron beam radiation, a catalyst is not required.
  • the aqueous monomer system is invariably associated, as required, with filler(s) , plasticizer(s) , catalyst(s) and foaming agent(s) .
  • the filler may be selected from those set forth hereafter.
  • This aspect features a dispersion of solid in mobile fluid, the composition being curable as by radiation or by the use of (e.g.) free radical-producing catalysts.
  • the especially preferred aqueous monomer system is ' a one-part monomer system; however, a two- or three-part monomer system may also be used. These are described in further detail below.
  • the water-soluble or -miscible (or -dispersible) monomer may be selected from any conventional monomer.
  • Such monomers include acrylic and methacrylic acid and derivatives thereof; acrylamide and N-methylol acrylamide and derivatives thereof; modified acrylamide, especially acrylamide modified with aldehydes and the like to ultimately form polymerization-condensation type polymers; and pyrrolid- ones such as vinyl pyrrolidones and mixtures thereof.
  • the catalysts are generally conven ⁇ tional free radical-producing components which are chosen in accordance with the type of radiation (heat, U.V. , et al) , or other curing, to be employed. Their purpose is to initiate and/or increase the rate of reaction.
  • the catalysts may be (e.g.) U.V. photoinitiators or free radical-producing catalysts (either alone or as redox couple) or other type - and, as specific examples, there are mentioned persulphates (e.g. ammonium persulphate), peroxides, AZDN, together with various reducing agents such as sodium bisulphite, sodium formaldehyde sulphoxylate , and zinc formaldehyde sulphoxy- late.
  • persulphates e.g. ammonium persulphate
  • peroxides AZDN
  • the benzildimethylketal compound known as "IRGACURE 651" (a Registered Trade Mark of Ciba-Geigy) is a typically suitable compound for promoting (.the initiating effect of) U.V. radiation. Where curing is effected by electron beam radiation a catalyst is not required. The catalyst may be added simultaneously with the monomer. Alternatively, it may be added subsequently together with other optional conventional additives (such as fillers) , or as prior application to the substrate upon which the composition is subsequently to be applied.
  • the plasticizer which functions to improve the flex ⁇ ibility of the cured composition, is preferably a humectant plasticizer.
  • Typical examples are calcium and zinc chloride, sugar, glycerine and glycols; other examples include synthetics such as starch and starch derivatives, polyvinyl alcohol, gum and modified cellulose.
  • non- reactive water borne components which are exemplified by emulsions or dispersed or dissolved resins or polymers, do not take part in the polymerization reaction. However, they are easily dispersed or dissolved in the compositions and function to improve the end properties.
  • oxygen inhibition can be a performance problem.
  • we overcome the problem by externally applying nitrogen to the printed substrate.
  • alkali e.g. basic carbonate for an acidic form ⁇ ulation
  • acid-base reactants may be used, such as hydrochloric acid and basic carbonate (e.g. sodium bicarbonate or ammonium carbonate) .
  • a basic carbonate alone may be used. The monomer system during reaction turns acid and thus subsequently reacts with the carbonate alkali to ultimately form C0 2 .
  • a three-part system may comprise a first water-soluble or 5 -miscible (or-dispersible) monomer part, a second part including plasticizer (e.g. a low-cost carbohydrate plasti ⁇ cizer) , an acid and a free-radical catalyst, and a third part comprising a plasticizer, a C0 2 inclusive alkali and a reducing redox couple.
  • plasticizer e.g. a low-cost carbohydrate plasti ⁇ cizer
  • the three parts may be mixed and,
  • a two-part monomer system may have one part including a water-soluble or -miscible (or -dispersible) monomer, a plasticizer (e.g. a carbohydrate plasticizer) , a CO., inclusive alkali and a U.V. catalyst, and a second part consisting of
  • L5 carbohydrate plasticizer solution and acid (the parts may be alternatively constituted as indicated in the detailed examples below) .
  • the parts are mixed and cured (e.g. by exposure to U.V. light) , polymerization, with formation of C0 2 gas, takes place. The gas so formed produces foaming
  • Such a system may comprise a water- soluble or -miscible (or -dispersible) monomer, a latent
  • the coating component may be a dyestuff or pigment.
  • these terms encompass water-soluble dyestuffs, aqueous pigment dispersions, and such materials as clays (e.g. china clay) and whiting.
  • Other additivies - such as surfactant(s) (to aid dispersion), plasticizers (as indicated above) and viscosity controllers - may also be present as required.
  • the especially preferred water-soluble or -dispersible monomers are acrylamide or N-methylol derivatives thereof.
  • the con ⁇ ventional method for producing acrylamide is by hydrating acrylonitrile in the presence of sulphuric acid and water at 100 C, thus forming acrylamide sulphate and subsequently removing the sulphate and recovering pure acrylamide.
  • the acrylamide may be produced by reacting acrylonitrile in the presence of hydrochloric acid to produce acrylamide chloride.
  • hydrochloric acid By further addition of calcium hydroxide, calcium chloride is formed. The production of calcium chloride in this way is a convenient and inexpensive means of eliminating an otherwise unwanted by-product.
  • Acrylamide monomer as such (without further modification) is suitable as the water-soluble or dispersible monomer.
  • modification of the acrylamide to the N-methylol derivatives adds even greater latitude to the formulation.
  • the reaction of acrylamide with various aldehydes will form the corresponding methylol products and then .upon polymeriz ation the condensation reaction occurs simultaneously.
  • Formaldehyde in the form of paraformaldehyde
  • the percentage solids is not critical.
  • suc compositions may be applied to a substrate using convention techniques and cured using such methods as described above.
  • Typical substrates includepaper, board, wood, metal masonry glass, cloth synthetic surfaces and the like.
  • the compo ⁇ sitions may contain conventional solid carriers (fillers) a primary component.
  • solid carriers there may be mentione (ground) natural minerals, such as clays, talc, chalk, kaol quartz, diatomaceous earth and the like and (ground) synthe minerals such as alumina and silicates and the like.
  • ground natural minerals
  • talc clays, talc, chalk, kaol quartz, diatomaceous earth and the like
  • ground synthe minerals such as alumina and silicates and the like.
  • ro crushed and fractionated
  • IP such as marble, calcite pumice and the like as well as (granules of) organic materials such as solid synthetic poly ⁇ mers (e.g. polyethylene) , sawdust and vegetable fibres and organic pulp such as paper pulp and the like.
  • the water-soluble or -miscible (or -dispersible) monomer acts as a binder for such solid carriers.
  • methylol acrylamide together with a heat induced free radical catalyst acts as a binder for sand and/or marble chips.
  • the advantage of the process lies in the considerable energy savings resulting from the polymerization reaction which is exothermic.
  • the above-mentioned carrier(s) can, of course, be augmented.
  • plasticizer(s) , stabilizer(s) , dyestuff(s) and the like may also be added.
  • the com ⁇ position may be based on water-soluble monomer, plasticizer(s) 5 and foaming agent(s) .
  • the water-soluble monomer may be in the form of a two-part monomeric system, the parts (including monomer, plasticizer, catalyst et al) being as constituted heretofore or as specifically exemplified in the subsequent examples.
  • a three-part system may comprise a first monomer part, a second part incorporating a plasti ⁇ cizer, an acid and a free radical catalyst, and a third par incorporating plasticizer, C0 2 inclusive alkali and reducin redox couple.
  • the components may be formulated to equal volume and mixed - with resultant simultaneous foaming and polymerization.
  • the foam composition thus produced (where air may act as a filler material) has use, inter alia, in insulation environments and as a protective coating for animals.
  • the first part comprises 100 parts by weight of N-methylol acrylamide -(.60%) (hereinafter sometimes referred to, for convenience, simply as N.M.A.).
  • the second part was formed from.50 parts by weight water, 45 parts by weight sugar, 3.5 parts by weight hydrochloric acid and 1.5 parts by weight ammonium .persulphate and a third part from 50 parts by weight water, 45 parts by weight sugar, 1.5 parts by weight sodium formaldehyde sulphox late, and 3.5 parts by weight sodium bicarbonate.
  • the three parts were mixed together in equal proportions.
  • This example illustrates a two-part monomer system.
  • the first part was produced by mixing 37.5 parts by weight water, 52 parts by weight calcium chloride, 2 parts by weight hydrochloric acid, 8 parts by weight acetone co-solvent, and 0.5 parts by weight of the catalyst known as "IRGACURE 651" Csee.heretofore) .
  • the second part was produced by 87 parts by weight 60% N.M.A. , 5 parts by weight ammonium hydroxide and 8 parts by weight ammonium carbonate and the two parts mixed together.
  • This example further illustrates a two-part monomer system.
  • the first part was formed by mixing 66 parts by weight 60% N.M.A. , 28 parts by weight 50% sugar/water solution 0.3 parts by weight "IRGACURE 651" and 5.7 parts by weight of sodium bicarbonate.
  • the second part was produced by
  • Gravure ink black: cured by U.V. radiation.
  • Composition 60% N-methylolacrylamide (water-soluble monomer) 52.0
  • the Primal 1-94 is neutralized with aqueous ammonia
  • Example 10 The P.V.P. K-30 (polyvinylpyrrolidone) is dissolved in the N.M.A. solution, and the surfactant and water are then added. The pigment and photoinitiator catalyst are dispersed as in Example 8. Printing upon the paper sub ⁇ strate is effected with a flexographic press. U.V. curing is carried out as in Example 8.
  • Example 10 The P.V.P. K-30 (polyvinylpyrrolidone) is dissolved in the N.M.A. solution, and the surfactant and water are then added. The pigment and photoinitiator catalyst are dispersed as in Example 8. Printing upon the paper sub ⁇ strate is effected with a flexographic press. U.V. curing is carried out as in Example 8.
  • Example 10 Example 10
  • Irgacure 651 photoinitiator catalyst 1.0 acetone 5.0 water 34.0
  • Example 11 The polymer emulsion is stirred into the N.M.A. solution and water is added.
  • the photoinitiator catalyst is dissolved in the acetone, following which the dissolved catalyst is slowly added to the N.M.A. solution with high speed mixing. Coating is effected per medium of a roll coater with doctor blade. Radiation is carried out as in Examples 8 and 9.
  • Example 11 Example 11
  • Transparent coating for clay coated paper cured by electron beam radiation.
  • Composition
  • Example 10 60% N-methylolacrylamide (water-soluble monomer) 50.0 33% Platamid M1255 (water-soluble copolyamide resin) 48.0 Eriosin blue dye 2.0
  • the polyamide and N.M.A. solutions are mixed, and the dye is dissolved therein.
  • Coating is effected as in Example 10.
  • Electrom bean radiation is carried out using a 250kV electron accelerator.
  • Irgacure 651 2.0 The photoinitiator catalyst is dispersed in N.M.A. solution, using a bead or sand mill. Thereafter, the clay is dispersed in a similar manner. Coating is carried out as in Examples 10 and 11 (alternatively, the doctor blade can be substituted by an air knife) . U.V. radiation is carr out as in Examples 8 to 10.
  • Glazing upon ceramic tiles cured by U.V. radiation.
  • Composition 60% N-methylolacrylamide (water-soluble monomer) 35.0 powdered red glazing glass (pigment) 40.0
  • Sandoray 1000 photoinitiator catalyst 1.0 acetone 4.0 water 10.0
  • the N.M.A. solution is diluted with water, the photo ⁇ initiator catalyst is dissolved in acetone, and the former is added to the latter with vigorous mixing.
  • the glazing compound is dispersed (with continued vigorous mixing) .
  • Silk screen printing is effected, and the U.V. radiation is performed as above.
  • Example 14 see Example 2
  • Foaming mix cured by U.V. radiation.
  • Composition Part A: 60% N-methylolacrylamide 87.0 aqueous ammonia 5.0 ammonium carbonate 8.0
  • Part B water 37.5 calcium chloride 52.0 hydrochloric acid (10M) 2.0 acetone 8.0
  • the aqueous ammonia and N.M.A. solution are mixed, and the ammonium carbonate is dissolved therein.
  • the calcium chloride plasti ⁇ cizer is dissolved in water, hydrochloric acid is added, the photoinitiator catalyst is dissolved in acetone, and the solutions are mixed with rapid stirring. Foaming commences when the two parts are mixed together. Radiation may be effected by direct sunlight.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Paints Or Removers (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Surface Treatment Of Glass (AREA)
  • Preparation Of Fruits And Vegetables (AREA)
  • Feed For Specific Animals (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Paper (AREA)
  • Fodder In General (AREA)
PCT/AU1980/000056 1979-08-31 1980-08-29 A polymerizable water-based composition WO1981000569A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE803049830T DE3049830T1 (de) 1979-08-31 1980-08-29 A polymerizable water-based composition

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
AUPE028879 1979-08-31
AU288/79 1979-08-31
AUPE122979 1979-11-06

Publications (1)

Publication Number Publication Date
WO1981000569A1 true WO1981000569A1 (en) 1981-03-05

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ID=25642328

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PCT/AU1980/000056 WO1981000569A1 (en) 1979-08-31 1980-08-29 A polymerizable water-based composition

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JP (1) JPH0379362B2 (enrdf_load_stackoverflow)
DE (1) DE3049830T1 (enrdf_load_stackoverflow)
GB (1) GB2070047B (enrdf_load_stackoverflow)
WO (1) WO1981000569A1 (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1982002894A1 (en) * 1981-02-27 1982-09-02 Pty Ltd Staybond Aqueous polymerizable compositions
GB2217338A (en) * 1988-04-11 1989-10-25 Sericol Group Ltd Printing inks
US6803112B1 (en) 2000-03-29 2004-10-12 Sun Chemical Corporation Radiation curable aqueous compositions for low extractable film packaging
US7037953B2 (en) 2000-03-29 2006-05-02 Sun Chemical Corporation Radiation curable aqueous compositions

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2008307151B2 (en) * 2007-10-05 2015-05-21 Filsen Pty Ltd Method for manufacturing sheet material
AU2018344119B9 (en) * 2017-10-02 2020-10-08 Dic Graphics Corporation Electron beam-curable water-based flexo ink for surface printing and boilable/retort pouch using same

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AU501686B2 (en) * 1975-02-18 1979-06-28 Flecto Coatings Ltd Stable aqueous emulsions
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AU5646365A (en) * 1965-03-17 1966-09-22 Celanese Corporation Of America Copolymer compositions and method of preparation
GB1320688A (en) * 1969-11-17 1973-06-20 Ici Ltd Asbestos filled compositions
US3959224A (en) * 1971-02-01 1976-05-25 The Lubrizol Corporation Water-soluble hydroxyalkylated and alkoxyalkylated compositions and the like derived from N-3-oxohydrocarbon-substituted acrylamides, and polymers thereof
CH562283A5 (enrdf_load_stackoverflow) * 1971-03-10 1975-05-30 Kema Nord Ab
GB1419462A (en) * 1972-07-19 1975-12-31 Lubrizol Corp Conversion coatings based on watersoluble substituted acrylamide compositions
FR2202923A1 (enrdf_load_stackoverflow) * 1972-10-14 1974-05-10 Nippon Paint Co Ltd
DE2360415A1 (de) * 1972-12-04 1974-06-06 Lion Fat Oil Co Ltd Verfahren zur herstellung von mit kunststoff ueberzogenen metallpulvern
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JPS528092A (en) * 1975-07-09 1977-01-21 Japan Synthetic Rubber Co Ltd Process for preparing organic pigments for use in paper coating
JPS5237946A (en) * 1975-09-18 1977-03-24 Takayoshi Kimimura Fluorescent brightened vinyl resin emulsion
AU505580B2 (en) * 1976-03-15 1979-11-22 Milchev Incorporated Graft vinyl copolymer on inorganic substrate
AU2341077A (en) * 1976-04-15 1978-09-21 American Cyanamid Co Composition of matter useful for earthen formation treatment
AU1320776A (en) * 1976-04-21 1977-10-27 Rohm & Haas Copolymers
JPS5319349A (en) * 1976-08-09 1978-02-22 Kansai Paint Co Ltd Aqueous coating compositions
JPS5330680A (en) * 1976-09-03 1978-03-23 Toshiba Corp Manufacture of magnetic material composites

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1982002894A1 (en) * 1981-02-27 1982-09-02 Pty Ltd Staybond Aqueous polymerizable compositions
GB2217338A (en) * 1988-04-11 1989-10-25 Sericol Group Ltd Printing inks
GB2217338B (en) * 1988-04-11 1991-12-18 Sericol Group Ltd Printing inks
US6803112B1 (en) 2000-03-29 2004-10-12 Sun Chemical Corporation Radiation curable aqueous compositions for low extractable film packaging
US7037953B2 (en) 2000-03-29 2006-05-02 Sun Chemical Corporation Radiation curable aqueous compositions

Also Published As

Publication number Publication date
DE3049830C2 (enrdf_load_stackoverflow) 1992-03-05
JPS56501404A (enrdf_load_stackoverflow) 1981-10-01
DE3049830T1 (de) 1982-02-25
JPH0379362B2 (enrdf_load_stackoverflow) 1991-12-18
GB2070047B (en) 1984-05-02
GB2070047A (en) 1981-09-03

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