WO2007139157A1 - Acrylamide ou méthacrylamide multivalent et formule aqueuse de résine durcissable le contenant - Google Patents

Acrylamide ou méthacrylamide multivalent et formule aqueuse de résine durcissable le contenant Download PDF

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Publication number
WO2007139157A1
WO2007139157A1 PCT/JP2007/061003 JP2007061003W WO2007139157A1 WO 2007139157 A1 WO2007139157 A1 WO 2007139157A1 JP 2007061003 W JP2007061003 W JP 2007061003W WO 2007139157 A1 WO2007139157 A1 WO 2007139157A1
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meth
acrylamide
compound
polyvalent
group
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PCT/JP2007/061003
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English (en)
Japanese (ja)
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Yasuhiro Matsuda
Akihiko Fukada
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Nippon Shokubai Co., Ltd.
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Priority to JP2008517971A priority Critical patent/JPWO2007139157A1/ja
Publication of WO2007139157A1 publication Critical patent/WO2007139157A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen

Definitions

  • the present invention relates to a polyvalent (meth) acrylamide compound and an aqueous curable resin composition containing the same. More specifically, the present invention relates to a polyvalent (meth) acrylamide compound that has good active energy ray curability and is difficult to hydrolyze, and an aqueous curable resin composition containing the same. Background art
  • a composition that forms and cures a crosslinked structure by heating or irradiation with active energy rays is used in various applications such as inks, coating agents, paints, and adhesives, and is very useful industrially. It is known (for example, see Patent Document 1).
  • a curable composition by using a compound having a plurality of reactive functional groups, it can be processed into various shapes because of its low viscosity at the time of work. Since the structure is formed, the composition can be a cured product having excellent heat resistance and solvent resistance.
  • curable compositions having such characteristics, unsaturated polyester resins, urethane acrylate resins, polyester acrylate resins, epoxy acrylate resins, and the like are known. Goods are used for various purposes. These curable compositions often use toluene-methyl ethyl ketone and les, organic solvents, and highly volatile reactive diluents such as styrene and (meth) acrylates to reduce viscosity. The However, in recent years, curable materials using water as a diluent instead of organic solvents and highly volatile reactive diluents have been demanded due to environmental problems.
  • polyvalent (meth) acrylamide compounds as a curable material have good curability when heated or irradiated with a line of active energy, and are more resistant to calories than (meth) ataretoy compounds. It has the property of being excellent in degradability.
  • a polyvalent (meth) acrylamide compound is applied to a composition containing water, hydrolysis produces N-hydroxymethylatanolenamide, which is further divided into toxic substances such as acrylamide and formaldehyde. To understand. Therefore, the polyvalent (meth) acrylamide compound has room for ingenuity in that the generation of harmful substances due to decomposition is suppressed and it can be used in a curable composition using water as a solvent. .
  • Patent Document 1 Japanese Patent Laid-Open No. 2002-284832 (Pages 1-2)
  • Patent Document 2 Japanese Patent Application Laid-Open No. 2004-83842 (Pages 1-2)
  • the present invention has been made in view of the above-mentioned present situation, and is cured well by heating or irradiation with active energy rays, has good water resistance and heat resistance after curing, and is resistant to hydrolysis.
  • An object of the present invention is to provide a polyvalent (meth) atyramide compound that is excellent, suppresses the generation of harmful substances, and can adjust the molecular weight, and a water-based curable resin composition containing the same.
  • the present inventors have made various studies on polyvalent (meth) atyramide compounds that can be used in a curable composition using water as a solvent. As a result, two or more (meth) acrylamides in one molecule are obtained. When it has a group, curing by heating or irradiation with active energy rays is good, water resistance and heat resistance after curing can be made good, and a carboxyl group or carboxyl group in the molecule can be obtained. It has been found that when the hydrogen atom has a group having a structure substituted with a base, water solubility, which is a characteristic necessary for use in an aqueous curable resin composition using water as a solvent, is improved.
  • the present invention relates to a polyvalent (meth) acrylamide compound having two or more (meth) acrylamide groups in one molecule, wherein the polyvalent (meth) acrylamide compound has a force lpoxyl group in the molecule.
  • it is a polyvalent (meth) acrylamide compound having a group having a structure in which a hydrogen atom of a carboxynole group is substituted with a base and having a plurality of urethane bonds.
  • the polyvalent (meth) acrylamide compound in the present invention has two or more (meth) acrylamido groups in one molecule.
  • the polyvalent (meth) acrylamide compound has a carboxyl group or a group having a structure in which a hydrogen atom of the carboxyl group is substituted with a base in the molecule.
  • water can be used as a diluent.
  • a group having a structure in which a hydrogen atom of a carboxynole group is substituted with a base is preferable.
  • the groups may be the same or different.
  • the polyvalent (meth) acrylamide compound is preferably obtained by reacting with a base. What is obtained by reacting with a base is preferably a polyvalent (meth) acrylamide compound in which the hydrogen atom of the carboxyl group is substituted (neutralized) with a base in the molecule.
  • Examples of the polyvalent (meth) acrylamide compound include the following chemical structural formulas (1) to (5); [0012]
  • Examples of the base include ammonia, butylamine, triethylamine, monoethanolamine, diethanolamine, triethanolamine, triisopropanolamine, aniline, pyridine, lithium hydroxide, sodium hydroxide, potassium hydroxide, Magnesium hydroxide, barium hydroxide, lithium acetate, sodium acetate, potassium acetate, magnesium acetate, calcium acetate, lithium carbonate, potassium carbonate, sodium carbonate, sodium bicarbonate, potassium bicarbonate, lithium benzoate, sodium benzoate And potassium benzoate, trisodium phosphate, tripotassium phosphate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, and the like.
  • the present invention is also a polyvalent (meth) atrylamide compound having two or more (meth) acrylamide groups in one molecule, wherein the polyvalent (meth) acrylamide compound is a polyfunctional isocyanate compound.
  • A a polyol-based compound (B) having a carboxyl group and a compound (C) having a (meth) acrylamide group, and the compound (C) having the (meth) acrylamide group ,
  • R 1 represents a hydrogen atom or a methyl group.
  • R 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • N is an integer of 2 or more
  • It is also a meta) acrylamide compound.
  • the compound (C) having the (meth) acrylamide group is represented by the following general formula (1);
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • n is an integer of 2 or more
  • the polyfunctional isocyanate is not particularly limited as long as it is a compound having two or more isocyanate groups in the molecule.
  • Adaku Totaipu tolylene iso Xia sulfonates and the like can be used as one or a mixture of two or more.
  • the above-mentioned Polio-Rui compound is not particularly limited as long as it is a compound having one or more carboxyl groups and two or more hydroxyl groups in the molecule.
  • 2,2-bis (hydroxyethyl) propionic acid 2, 2 —Bis (hydroxypropyl) propionic acid, bis (hydroxymethyl) acetic acid, bis (hydrochichetil) acetic acid, 2,4 dihydroxybenzoic acid, 3,5 dihydroxybenzoic acid, 4,4 bis (4-hydroxyphenyl)
  • pentanoic acid and tartaric acid These can be used alone or as a mixture of two or more.
  • the polyvalent (meth) acrylic compound of the present invention may be a compound obtained by attaching ethylene oxide or propylene oxide to a polyol compound having these carboxy
  • the polyvalent (meth) acrylamide compound of the present invention is obtained by reacting the polyfunctional isocyanate compound (A), the polyol compound (B) having a carboxyl group, and the compound (C) having a (meth) acrylamide group. Is obtained.
  • the (meth) acrylic compound obtained by such a reaction is useful for various applications, and is a polyfunctional isocyanate compound (A ),
  • the polyol compound (B) having a carboxyl group and the compound (C) having a (meth) acrylamide group the molecular weight can be easily adjusted, so that the viscosity can be adjusted. It can be cured well by heating or irradiation with active energy rays, and can have good water resistance and heat resistance after curing.
  • the polyvalent (meth) acrylamide compound is preferably obtained by reacting with a base.
  • the reaction molar ratio of the polyfunctional isocyanate compound (A), the polyol compound (B) having a carboxylate group and the compound (C) having a (meth) acrylamide group is 2 to 3: 1 to 1 to 2: It is preferable that it is 2-4. Although it may be set as appropriate depending on the use of the (meth) acrylamide compound and the desired physical properties, etc., the polyfunctional isocyanate compound (A) per 1 mole of the (meth) acrylamide group in the compound (C) having a (meth) acrylamide group ), Preferably 1 to: 10 moles. More preferably: from!
  • the polyol compound (B) having a carboxyl group should be 0.5 to 10 moles per mole of the (meth) acrylamide group in the compound (C) having a (meth) acrylamide group. preferable. More preferably, it is 0.5 to 3 mol.
  • the reaction includes the reaction (1) with the polyfunctional isocyanate compound (A) and the polyol compound (B) having a carboxyl group, the compound produced by the reaction, and the (meth) acrylamide group. And a reaction (2) for producing a (meth) acrylamide compound obtained by bonding a compound (C) having a urethane bond with a urethane bond.
  • the compound produced by the reaction (1) is preferably a compound in which the isocyanate group of the polyfunctional isocyanate compound (A) and the hydroxyl group of the polyol compound (B) having a carboxyl group are bonded by a urethane bond.
  • the addition method of the polyfunctional isocyanate compound (A) and the polyol compound (B) having a carboxyl group in the above reaction (1) may be charged all at once in the initial stage of the reaction, or both may be continued. Or you may add to a reaction system intermittently.
  • the above reaction is preferably performed in the presence of a catalyst.
  • the catalyst is preferably a urethane catalyst.
  • multifunctional isocyanate The reaction between the isocyanate group in the nate (A) and the reactive group present in the compound (C) having a hydroxyl group or a (meth) acrylamide group in the carboxyl group-containing polyol compound (B) should be sufficiently promoted. Can do.
  • Examples of the urethanization catalyst include organometallic catalysts and amine catalysts.
  • An organometallic catalyst is preferable.
  • organometallic catalyst examples include dibutyltin dilaurate, dibutyltin diacetate, dibutyltin malate, tin stearate, tin oxalate, zinc otate and the like. These can be used as one kind or a mixture of two or more kinds. Preferred is a urethane catalyst or dibutyltin dilaurate.
  • the amount of the catalyst used includes the polyfunctional isocyanate compound (A) used in the reaction, the polyol compound (B) having a carboxyl group, and the compound (C) having a (meth) acrylamide group. It may be set appropriately depending on the type and combination, but from the viewpoints of yield, catalyst stability, productivity and economy, the polyfunctional isocyanate compound (A), the polyol compound (B) having a carboxyl group and ( With respect to 100 parts by mass of the compound (C) having a meth) acrylamide group, the active ingredient as a catalyst is preferably 0.00001 parts by mass or more, and preferably 1 part by mass or less. More preferably, it is 0.000005 parts by mass or more and 0.5 parts by mass or less as an active ingredient as a catalyst.
  • the polyfunctional isocyanate compound (A), the polyol compound (B) having a carboxyl group, and the compound (C) having a (meth) acrylamide group have a radical polymerizable group.
  • Examples of the polymerization inhibitor include quinone-based polymerization inhibitors such as hydroquinone, methoxyhydroquinone, benzoquinone, and p-tert-butylcatechol 1J; 2, 6 _di-tert-butylphenol, 2, 4_di-tert —Butylphenol, 2_tert_butyl 4,6_dimethylphenol, 2,6-di-tert_butyl_4_methylphenol, 2,4,6-tri-alkyl alkylphenol polymerization such as tert-butylphenol is prohibited Lj; amine-based polymerization inhibitors such as alkylated diphenylamine, N, N r —diphenyl _p-phenylenediamine, phenothiazine; 4-hydro N-oxyls such as tetramethylpiperidine N-oxyl; copper dithiocarbamate such as copper dimethyldithiocarbamate, copper diethyldi
  • hydroquinone methoxyhydroquinone, alkylated diphenylamine, benzoquinone, phenothiazine, and N-oxyls such as 4-hydroxy-2,2,6,6-tetramethylpiperidine and N-oxyl are preferred. . More preferred are N-oxyls such as 4-hydroxy-1,2,2,6,6-tetramethylpiperidine and N-oxyl.
  • the amount of addition of the polymerization inhibitor includes polyfunctional isocyanate compounds (A), polyol compounds (B) having carboxyl groups, and compounds (C) having (meth) acrylamide groups.
  • the polyfunctional isocyanate compound (A), the polyol compound having a carboxyl group (B), and (in view of the polymerization inhibitory effect, yield, productivity and economy, may be set appropriately. It is preferable to use 0.001 part by mass or more with respect to 100 parts by mass of the compound (C) having a (meth) acrylamide group, and it is also preferable to use 5 parts by mass or less. More preferably, it is 0.005 parts by mass or more, and 1 part by mass or less, and particularly preferably 0.01 parts by mass or more, and 0.1 parts by mass or less.
  • the temperature of the above reaction is preferably 40 to 150 ° C from the viewpoint of yield, productivity and economy. More preferably, it is 30-100 degreeC, Most preferably, it is 20-70 degreeC.
  • the reaction time is such that the polyfunctional isocyanate compound (A), the polyol compound (B) having a carboxyl group and the compound (C) having a (meth) acrylamide group, the catalyst and the organic to be used so that the above reaction is completed. What is necessary is just to set suitably according to the kind and combination of a solvent, usage-amount, etc.
  • the reaction pressure may be appropriately set depending on the kind of the polyfunctional isocyanate compound (A), the polyol compound (B) having a carboxylate group and the compound (C) having a (meth) acrylamide group, the reaction temperature, etc. Any pressure of normal pressure (atmospheric pressure), reduced pressure, and increased pressure may be used as long as the reaction system is kept in a liquid state.
  • the above reaction may be performed without a solvent, but may be performed in an organic solvent or a reactive monomer having an unsaturated double bond, if necessary.
  • the organic solvent is not particularly limited, but a water-soluble substance is more preferable.
  • Examples of organic solvents include And methyl methyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, tetrahydrofuran, dioxane, acetonitrile, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, N-methyl 2-pyrrolidone and the like.
  • One or more of these organic solvents can also be used.
  • the (meth) acrylamide compound may contain a hydrophilic monomer having an unsaturated double bond.
  • hydrophilic monomer examples include hydroxyethyl (meth) acrylate, hydroxypropinole (meth) acrylate, hydroxybutyl (meth) acrylate, diethylene glycol mono (meth) acrylate, triethylene glycol mono Hydroxyl group-containing (meth) acrylate, such as (meth) acrylate, tetraethylene glycol mono (meth) acrylate; pentaethylene glycol di (meth) acrylate, hexaethylene glycol di (meth) acrylate, heptaethylene Polyethylene glycol di (meth) acrylate, such as glycol di (meth) acrylate and octaethylene glycol di (meth) acrylate; part of hydroxyl groups in polyhydric hydroxyl group-containing compounds such as glycerin and pentaerythritol (meth) acryl Compound obtained by reacting; epoxy acrylate obtained by addition of (meth) atalinole
  • the present invention further relates to an aqueous curable resin composition containing the polyvalent (meth) acrylamide compound, wherein the aqueous curable resin composition includes a polyvalent (meth) acrylamide compound. It is also an aqueous curable resin composition containing water and a polymerization initiator. Since the polyvalent (meth) acrylamide compound is excellent in hydrolysis resistance and improved in water solubility, it can be used in a curable composition containing water as a component.
  • the water content in the aqueous curable composition of the present invention is preferably 1% by mass or more with respect to 100% by mass of the composition containing a polyvalent (meth) acrylamide compound. It is preferable to be 99% by mass or less. More preferably, it is 5% by mass or more and 90% by mass or less. Most preferably, it is 10% by mass or more and 80% by mass or less.
  • a heat or photopolymerization initiator is used.
  • thermal polymerization initiator examples include methyl ethyl ketone peroxide, benzoyl peroxide, dicumyl peroxide, t-butyl hydride peroxide, cumene hydride peroxide, t-butyl peroxide, t-butyl peroxide.
  • organic peroxides such as xybenzoate and lauroyl peroxide; azo compounds such as azobisisoptyronitrile.
  • cobalt naphthenate, cobalt octylate, etc. or tertiary amine can be preferably used.
  • the amount of addition of the thermal polymerization initiator is preferably 0.01 to 10 parts by mass with respect to 100 parts by mass of the aqueous curable composition. More preferably, it is 0.05 to 5 parts by mass, and most preferably 0.:! To 3 parts by mass.
  • Examples of the photopolymerization initiator include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.
  • Nzoin and its alkyl ethers acetophenone, 2, 2-dimethoxy-1, 2-phenolefactophenone, 1,1-dichloroacetophenone, 4-- (1-t-butyldioxy-1-methinoleethyl) acetophenone, 2-methyl-1 [4- (Methylthio) phenyl] — 2—morpholinopropan _ 1 _one or 2-benzyl-2-dimethylamino _ 1 _ (4 _morpholinophenyl) -butane _ 1 _one, methoxyacetophenone, 2-Hydroxy-1-methyl _ 1 -phenylpropane _ 1 _one, benzyl dimethyl ketal
  • Anthraquinones such as 2-methylanthraquinone, 2_amylanthraquinone, 2_t-butylanthraquinone, 1_black mouth anthraquinone; 2,4_dimethylthioxanthone, 2,4-dipropylpropylxanthone, 2-chloro Mouth thixanthone, 2-isopropylthioxanthone, 4 isopropyl thixanthone, 2,4 jetylthioxanthone, 2,4 dichlorothixanthone, 1 chloro-4 propoxythixanthone, 2- (3 dimethylamino-2-hydroxy) 3, 4-dimethyl-9H— Thioxanthene-9 Thioxanthones such as omesochloride; Ketones such as acetophenone dimethyl ketal and benzyl dimethyl ketal; benzophenone, 4- (1-t butyldioxy-1-methylethyl) be
  • the polymerization initiator contained in the aqueous curable composition of the present invention any of the above-mentioned photopolymerization initiators can be used, and the aqueous curable composition contains water. Specifically, it is preferable to use a water-soluble photopolymerization initiator.
  • the addition amount of the photopolymerization initiator is preferably 0.01 to 30 parts by mass with respect to 100 parts by mass of the aqueous curable composition. More preferably, it is 0.05 to 20 parts by mass, and most preferably 0.:! To 10 parts by mass.
  • a basic compound can be used together with the photopolymerization initiator. It is preferable to use an amine compound as the basic compound.
  • the amine compound is not particularly limited, and specific examples thereof include monomethylamine, dimethylamine, trimethylolamine, monoethylamine, jetylamine, triethinoreamin, Examples thereof include monopropylamine, dimethylpropylamine, monoethanolamine, diethanolamine, ethylenediamine, diethylenetriamine, dimethylaminoethyl methacrylate, polyethyleneimine, triethanolamine, and triisopropanolamine. Of these, tertiary amine compounds are particularly preferred.
  • the polyvalent (meth) acrylamide compound of the present invention and an aqueous curable resin composition containing the same has the above-mentioned configuration, and is cured well by heating or irradiation with active energy rays, has good water resistance and heat resistance after curing, has excellent hydrolysis resistance, and suppresses the generation of harmful substances. It is possible to adjust the molecular weight.
  • N hydroxyethyl acrylamide (manufactured by Kojin Co., Ltd .: HEAA) 90.5 g divided into 3 parts was added every 10 minutes while paying attention to heat generation. After completion of the addition, stirring was continued at 80 ° C for 3 hours. Subsequently, 15.7 g of sodium hydroxide dissolved in 120. Og of ion-exchanged water was added, and the mixture was further stirred for 30 minutes. Finally, the solvent methyl ethyl ketone was distilled off under reduced pressure, and after distillation, ion-exchanged water 160. Og was added, and a water-soluble urethane acrylamide resin 1 (non-volatile component 51.0%) (chemical structure) Formula (6));
  • Example 2 In a flask equipped with a stirrer, thermometer, condenser, and dropping device, dimethylolpropionic acid (Nippon Kasei Co., Ltd., Nitsukamer PA) 84.8 g, methyl ethyl ketone 119.9 g, tolylene 2, 4 diisocyanate (Tokyo) 146. 8g was added and stirred and heated while maintaining the internal temperature at 80 ° C. After 2 hours, 14 mg of 4H-TEMPO was added.
  • dimethylolpropionic acid Nippon Kasei Co., Ltd., Nitsukamer PA
  • Tokyo 4 diisocyanate
  • isophorone diisocyanate (Sumitomo Bayer Urethane Co., Ltd., Death Module I) 151.3g, Methyl Ethanolene 41.3g, The mixture was heated to a temperature of 70 ° C by stirring 0.4 g of 4 g of rice cake and 84 mg of 4H-TEMPO.
  • a mixture of N-hydroxyethylacrylamide (manufactured by Kojin Co., Ltd .: HEAA) 78.3 and 78.3 g of methinoretino ketone was continuously added dropwise for 2 hours.
  • neopentyl alcohol MPG, NPG
  • methyl ethyl ketone 120 g tolylene 2, 4 diisocyanate
  • Tokyo 142. 9g was added and stirred, and heated while maintaining the internal temperature at 80 ° C. After 2 hours, 14 mg of 4-hydroxy-2,2,6,6-tetramethylpiperidine mono-N-oxyl (hereinafter referred to as “4H—TEMPO”) was calories.
  • 4H—TEMPO 4-hydroxy-2,2,6,6-tetramethylpiperidine mono-N-oxyl
  • N hydroxyethyl acrylamide (manufactured by Kojin Co., Ltd .: HEAA) 94.4 g divided into 3 parts was added every 10 minutes while paying attention to heat generation. After completion of the addition, stirring was continued at 80 ° C for 3 hours. After the reaction, methyl ethyl ketone as a solvent was distilled off under heating and reduced pressure, and 160. Og of ion-exchanged water was added after the distillation. Although stirring and mixing were performed, the obtained resin was insoluble in water.
  • nonanediol ditalylate manufactured by Kyoeisha Igaku Co., Ltd., light acrylate 9EG-A was used as it was.
  • the polyvalent (meth) acrylamide compound of the present invention (Examples:! To 3) was able to obtain a cured resin film even after removal after storage. As a result, it was found that the polyvalent (meth) acrylamide compound of the present invention has excellent hydrolysis resistance.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un acrylamide ou un méthacrylamide qui peut être durci par chauffage ou irradiation à l'aide d'un rayonnement énergétique activant. L'acrylamide ou méthacrylamide présente une bonne résistance à l'eau et à la chaleur après durcissement, ainsi qu'une excellente résistance à l'hydrolyse. En outre, l'acrylamide ou méthacrylamide ne génère pas de substances dangereuses et sa masse moléculaire peut être maîtrisée. La présente invention concerne également une formule aqueuse de résine durcissable contenant un tel acrylamide ou méthacrylamide. La présente invention concerne spécifiquement un acrylamide ou méthacrylamide multivalent comportant deux groupements acrylamide ou méthacrylamide ou plus par molécule. L'acrylamide ou méthacrylamide multivalent porte un groupement carboxy ou un groupement au sein duquel un atome d'hydrogène de groupement carboxy est substitué par une base, tout en comportant une multitude de liaisons uréthane au sein d'une même molécule.
PCT/JP2007/061003 2006-05-31 2007-05-30 Acrylamide ou méthacrylamide multivalent et formule aqueuse de résine durcissable le contenant WO2007139157A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
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WO2015029878A1 (fr) * 2013-08-30 2015-03-05 Ｄｉｃグラフィックス株式会社 Composition aqueuse de vernis de surimpression durcissable par rayonnement uv
WO2015141537A1 (fr) * 2014-03-17 2015-09-24 Ｋｊケミカルズ株式会社 Oligomère d'uréthane et composition de résine durcissable par rayons d'énergie active le contenant
WO2017047565A1 (fr) * 2015-09-15 2017-03-23 Ｋｊケミカルズ株式会社 Composé (méth)acrylamide à modification uréthane et composition de résine durcissable par des rayons d'énergie active le contenant
WO2020011805A1 (fr) * 2018-07-10 2020-01-16 Dsm Ip Assets B.V. Dispersions aqueuses de polyuréthane durcissables par rayonnement
WO2021002307A1 (fr) * 2019-07-03 2021-01-07 株式会社Adeka Composé amide, composition polymérisable, produit durci et leur procédé de production

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