CN103554412B - A kind of aqueous dual-component acrylic acid-polyurethane resin and preparation method thereof - Google Patents
A kind of aqueous dual-component acrylic acid-polyurethane resin and preparation method thereof Download PDFInfo
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- CN103554412B CN103554412B CN201310499952.8A CN201310499952A CN103554412B CN 103554412 B CN103554412 B CN 103554412B CN 201310499952 A CN201310499952 A CN 201310499952A CN 103554412 B CN103554412 B CN 103554412B
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- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
- C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
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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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6237—Polymers of esters containing glycidyl groups of alpha-beta ethylenically unsaturated carboxylic acids; reaction products thereof
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- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
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- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
The present invention relates to a kind of aqueous dual-component acrylic acid-polyurethane resin and preparation method thereof, comprise component A: propyl carbinol; Monoethanolamine and/or n-Butyl Amine 99; Resorcinol and/or MEHQ; Glycidyl methacrylate; Methyl methacrylate and/or isobornyl methacrylate; Butyl acrylate and/or butyl methacrylate and/or lauryl acid esters; Hydroxyethyl acrylate; Diisopropyl azodicarboxylate; Ethylene glycol monobutyl ether and/or propylene glycol monomethyl ether; Molecular weight regulator; Dimethyl formamide; Acid acceptor; Water; B component comprises: butanone and/or ethyl acetate; 1-Methoxy-2-propyl acetate; Monoethanolamine and/or n-Butyl Amine 99; Hexahydrophthalic acid glycidyl ester and/or tetrahydrophthalic acid glycidyl ester; IPDI and/or HDI; Ethylene glycol monobutyl ether and/or ethylene glycol; Acid acceptor; Water; The weight proportion of component A and B component is 4 ~ 7:1.Utilize the coating film thickness obtained by resin of the present invention can reach more than 150 microns, without bubbling, pin hole.
Description
Technical field
The present invention relates to a kind of aqueous dual-component acrylic acid-polyurethane resin, this resin can in ambient cure.The invention still further relates to the preparation method of this resin.
Background technology
Two-component polyurethane systems has excellent mechanical property (hardness of film is high, strong adhesion, wear resistance are high), good chemical-resistant, weathering resistance and film formation at low temp performance, be widely used in the aspects such as industrial protection, wood furniture and automobile covering with paint.Along with the sound of various countries' environmental regulation and the enhancing of people's environmental consciousness, the quantity discharged of the volatile organic compounds (VOC) in traditional solvent-borne two component polyurethane is subject to more and more strict restriction.Aqueous polyurethane coating with bi component is then that the low VOC of the high-performance coating of solvent-type double-component urethane and water-borne coatings is discharged the product combined, and is a kind of environmentally friendly type coating system newly.The water-based polyvalent alcohol of current product primarily of hydroxyl and the solidifying agent containing isocyanate group form.
Although the advantage of aqueous two-component polyurethane systems is many, but because the solidifying agent used contains isocyanate groups, its some defects existed are also obvious, also its application is seriously limited, as: pot-life is short, and after mixing, isocyanic ester and hydroxyl, water at room temperature also can react, and system was lost efficacy, lose the crosslinking ability of film, affect performance.Also have in cured with isocyanates process and also react than being easier to water, produce gas CO
2if coating thickness is comparatively large, the CO produced in dry solidification process
2cannot discharge smoothly, or discharge comparatively slow, bubble or pin hole will be formed on film, have a strong impact on performance and outward appearance.The film of the aqueous polyurethane coating with bi component according to investigations in industrial production is generally difficult to reach more than 80 μm, is also noted that the moisture in environment.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of aqueous dual-component acrylic acid-polyurethane resin and preparation method thereof.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of aqueous dual-component acrylic acid-polyurethane resin, mixes obtained by A composition and composition B;
Described A composition is composed of the following components:
Described composition B is composed of the following components:
During mixing, the weight proportion of described A composition and described composition B is 4 ~ 7:1.
Further, in aqueous dual-component acrylic acid-polyurethane resin as above, described molecular weight regulator is selected from the mixture of one or more compositions in the different monooctyl ester of 3-thiohydracrylic acid, n-dodecyl mercaptan or tertiary lauryl mercaptan.
In aqueous dual-component acrylic acid-polyurethane resin as above, described acid acceptor is organic acid.
Preferably, described organic acid is selected from the mixture of one or more compositions in formic acid, acetic acid or lactic acid.
The preparation method of aqueous dual-component acrylic acid-polyurethane resin described above, comprises the following steps:
Prepared by component A: add propyl carbinol, glycidyl methacrylate, Resorcinol and/or MEHQ in the reactor, be heated to 50 DEG C, drips monoethanolamine and/or n-Butyl Amine 99, within 1 ~ 2 hour, drips off, and 48 ~ 52 DEG C are incubated 2 hours; Be warming up to 70 ~ 75 DEG C, be incubated 3 ~ 4 hours, discharging, and with methyl methacrylate and/or isobornyl methacrylate, butyl acrylate and/or butyl methacrylate and/or lauryl acid esters, Hydroxyethyl acrylate, molecular weight regulator, Diisopropyl azodicarboxylate, dimethyl formamide is mixed with mixed solution; In another reactor, add ethylene glycol monobutyl ether and/or propylene glycol monomethyl ether, be heated to 110 DEG C ~ 115 DEG C, start to drip mixed solution, within 3 ~ 4 hours, drip off, be incubated 2 ~ 3 hours; Add initiator, be incubated 1 ~ 2 hour, be cooled to 90 ~ 100 DEG C, vacuumize except partial solvent, add neutralizing agent, water, adjust PH to be 6 ~ 7, cold filtration discharging is component A;
Prepared by B component: add butanone and/or ethyl acetate in the reactor, hexahydrophthalic acid glycidyl ester and/or tetrahydrophthalic acid glycidyl ester, be heated to 40 DEG C under agitation condition, start to drip monoethanolamine and/or n-Butyl Amine 99, temperature is 40 ~ 43 DEG C, within 1 ~ 1.5 hour, drips off; Be warming up to 50 ~ 53 DEG C after dripping off, be incubated 2 hours; Heat up 70 ~ 75 DEG C, be incubated 3 ~ 4 hours; Be cooled to 40 DEG C, start IPDI and/or HDI of dropping 1-Methoxy-2-propyl acetate dilution, within 2 ~ 3 hours, drip off, after dripping off, 39 ~ 42 DEG C are incubated 2 hours; Be warming up to 45 ~ 49 DEG C, be incubated 3 hours; Heat up 60 ~ 64 DEG C, be incubated 3 hours, survey NCO content, later survey per hour nco value, reacts completely to nco value <0.5; Vacuumize remove portion solvent, add neutralizing agent, ethylene glycol monobutyl ether and/or ethylene glycol, water, adjust PH to be 6 ~ 6.5, cold filtration discharging is B component.
Described A composition and described composition B are mixed by formula.
The invention has the beneficial effects as follows: so that the crosslinked at low temperature solidification modified function monomer of amido and common acrylate monomers copolymerization water-borne acrylic resin can be obtained for component A, with containing carbamate groups can with the resin of component A crosslinking curing under cryogenic for B component, common formation aqueous dual-component acrylic acid-polyurethane resin system, obtained coating dodges dry 15 minutes, 80 DEG C are toasted 30 minutes, after cooling, survey fundamental property, it is normal without bubbling that thickness can reach more than 150 microns coatingsurfaces, pin hole.
Embodiment
Be described principle of the present invention and feature below in conjunction with embodiment, example, only for explaining the present invention, is not intended to limit scope of the present invention.
Embodiment 1
In embodiment 1, aqueous dual-component acrylic acid-polyurethane resin mixes obtained by A composition and composition B;
Described A composition is composed of the following components:
Propyl carbinol | 50g; |
Monoethanolamine | 61g; |
Resorcinol | 0.05g; |
Glycidyl methacrylate | 140g; |
Methyl methacrylate | 65g; |
Butyl acrylate | 65g; |
Hydroxyethyl acrylate | 10g; |
Diisopropyl azodicarboxylate | 6g; |
Ethylene glycol monobutyl ether | 80g; |
Molecular weight regulator (tertiary lauryl mercaptan) | 4g; |
Dimethyl formamide | 24g; |
Acid acceptor (formic acid) | 13.6g; |
Water | 600g; |
Described composition B is composed of the following components:
Butanone | 40g; |
1-Methoxy-2-propyl acetate | 10g; |
N-Butyl Amine 99 | 22.8g; |
Hexahydrophthalic acid glycidyl ester | 200g; |
IPDI | 34.6g; |
Ethylene glycol monobutyl ether | 20g; |
Acid acceptor (formic acid) | 14.4g; |
Water | 10g; |
The preparation process of aqueous dual-component acrylic acid-polyurethane resin is:
Prepared by component A: in 500ml reactor, add propyl carbinol, glycidyl methacrylate and Resorcinol, be heated to 50 DEG C, drips monoethanolamine, within 1 ~ 2 hour, drips off, and 50 DEG C are incubated 2 hours; Be warming up to 70 DEG C, be incubated 3 hours, discharging.Take out 79g and methyl methacrylate, butyl acrylate, Hydroxyethyl acrylate, molecular weight regulator, Diisopropyl azodicarboxylate, dimethyl formamide is mixed with mixed solution; In another 1000ml reactor, add ethylene glycol monobutyl ether, be heated to 110 DEG C, start to drip mixed solution, within 3 ~ 4 hours, drip off, be incubated 2 ~ 3 hours; Be cooled to 100 DEG C, vacuumize except partial solvent, add neutralizing agent (be formic acid at the present embodiment), water, adjust PH to be 6 ~ 7, cold filtration discharging is A composition;
Prepared by B component: in 500ml flask, add butanone, hexahydrophthalic acid glycidyl ester, be heated to 40 DEG C under agitation condition, start to drip n-Butyl Amine 99, temperature is 40 DEG C, within 1 hour, drips off; Be warming up to 50 DEG C after dripping off, be incubated 2 hours; Heat up 70 ~ 75 DEG C, be incubated 3 hours; Be cooled to 40 DEG C, start the IPDI of dropping 1-Methoxy-2-propyl acetate dilution, within 2 ~ 3 hours, drip off, after dripping off, 39 ~ 42 DEG C are incubated 2 hours; Be warming up to 45 DEG C, be incubated 3 hours; Be warming up to 60 ~ 64 DEG C, be incubated 3 hours, survey NCO content, later survey per hour nco value, reacts completely (after 3 hours, nco value is 0.42) to nco value <0.5; Vacuumize remove portion solvent, add neutralizing agent, ethylene glycol monobutyl ether, water, adjust PH to be 6 ~ 6.5, cold filtration discharging is composition B.
Described A composition and described composition B are pressed the mixing of 4:1 weight ratio, add water tune viscosity, spraying application.
Embodiment 2
In example 2, aqueous dual-component acrylic acid-polyurethane resin mixes obtained by A composition and composition B;
Described A composition is composed of the following components:
Described composition B is composed of the following components:
The preparation process of aqueous dual-component acrylic acid-polyurethane resin is:
Prepared by component A: in 500ml reactor, add 15g propylene glycol monomethyl ether, propyl carbinol, glycidyl methacrylate and MEHQ, be heated to 50 DEG C, drips monoethanolamine, within 1 ~ 2 hour, drips off, and 50 DEG C are incubated 2 hours; Be warming up to 70 DEG C, be incubated 3 hours, discharging.Take out 82.8g and methyl methacrylate, butyl acrylate, lauryl acid esters, Hydroxyethyl acrylate, molecular weight regulator, Diisopropyl azodicarboxylate, dimethyl formamide is mixed with mixed solution; In another 1000ml reactor, add 80g propylene glycol monomethyl ether, be heated to 110 DEG C, start to drip mixed solution, within 3 ~ 4 hours, drip off, be incubated 2 ~ 3 hours; Be cooled to 100 DEG C, vacuumize except partial solvent, add neutralizing agent (be acetic acid at the present embodiment), water, adjust PH to be 6 ~ 7, cold filtration discharging is A composition;
Prepared by B component: in 500ml flask, add butanone, ethyl acetate, hexahydrophthalic acid glycidyl ester, tetrahydrophthalic acid glycidyl ester, be heated to 40 DEG C under agitation condition, start to drip n-Butyl Amine 99, temperature is 40 DEG C, within 2 hours, drips off; Be warming up to 50 DEG C after dripping off, be incubated 3 hours; Heat up 70 ~ 72 DEG C, be incubated 2 hours; Be cooled to 40 DEG C, start the IPDI of dropping 1-Methoxy-2-propyl acetate dilution, within 2 ~ 3 hours, drip off, after dripping off, 39 ~ 42 DEG C are incubated 2 hours; Be warming up to 45 DEG C, be incubated 3 hours; Be warming up to 60 DEG C, be incubated 3 hours, survey NCO content, later survey per hour nco value, reacts completely (after 3 hours, nco value is 0.48) to nco value <0.5; Vacuumize removing 30g solvent, add neutralizing agent, ethylene glycol monobutyl ether, water, adjust PH to be 6 ~ 6.5, cold filtration discharging is composition B.
Described A composition and described composition B are pressed the mixing of 6:1 weight ratio, add water tune viscosity, spraying application.
Embodiment 3
In embodiment 3, aqueous dual-component acrylic acid-polyurethane resin mixes obtained by A composition and composition B;
Described A composition is composed of the following components:
Described composition B is composed of the following components:
Butanone | 40g; |
1-Methoxy-2-propyl acetate | 8g; |
N-Butyl Amine 99 | 22.8g; |
Tetrahydrophthalic acid glycidyl ester | 200g; |
HDI | 26.2g; |
Ethylene glycol | 15g; |
Acid acceptor (lactic acid) | 14.4g; |
Water | 10g; |
The preparation process of aqueous dual-component acrylic acid-polyurethane resin is:
Prepared by component A: in 500ml reactor, add 50g ethylene glycol monobutyl ether, glycidyl methacrylate and Resorcinol, be heated to 50 DEG C, drips monoethanolamine, within 1 ~ 2 hour, drips off, and 50 DEG C are incubated 2 hours; Be warming up to 70 DEG C, be incubated 3 hours, discharging.Take out 79g and methyl methacrylate, isobornyl methacrylate, butyl acrylate, lauryl acid esters, Hydroxyethyl acrylate, molecular weight regulator, Diisopropyl azodicarboxylate, dimethyl formamide is mixed with mixed solution; In another 1000ml reactor, add 60g ethylene glycol monobutyl ether, propylene glycol monomethyl ether, be heated to 110 DEG C, start to drip mixed solution, within 3 ~ 4 hours, drip off, insulation 2, hour; Be cooled to 100 DEG C, vacuumize except partial solvent, add neutralizing agent (be lactic acid at the present embodiment), water, adjust PH to be 6 ~ 7, cold filtration discharging is A composition;
Prepared by B component: in 500ml flask, add butanone, tetrahydrophthalic acid glycidyl ester, be heated to 40 DEG C under agitation condition, start to drip n-Butyl Amine 99, temperature is 40 DEG C, within 1 hour, drips off; Be warming up to 50 DEG C after dripping off, be incubated 2 hours; Heat up 70 ~ 75 DEG C, be incubated 3 hours; Be cooled to 40 DEG C, start the HDI of dropping 1-Methoxy-2-propyl acetate dilution, within 2 ~ 3 hours, drip off, after dripping off, 39 ~ 42 DEG C are incubated 2 hours; Be warming up to 45 DEG C, be incubated 3 hours; Be warming up to 60 DEG C, be incubated 3 hours, survey NCO content, later survey per hour nco value, reacts completely (after 3 hours, nco value is 0.36) to nco value <0.5; Vacuumize removing 30g solvent at 60 DEG C of temperature, add neutralizing agent, ethylene glycol, water, adjust PH to be 6 ~ 6.5, cold filtration discharging is composition B.
Described A composition and described composition B are pressed the mixing of 7:1 weight ratio, add water tune viscosity, spraying application.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (3)
1. an aqueous dual-component acrylic acid-polyurethane resin, mixes obtained by A composition and composition B;
Described A composition is composed of the following components:
Laurate
Described composition B is composed of the following components:
Formic acid glycidyl ester
During mixing, the weight proportion of described A composition and described composition B is 4 ~ 7:1.
2. aqueous dual-component acrylic acid-polyurethane resin according to claim 1, is characterized in that, described molecular weight regulator is selected from the mixture of one or more compositions in the different monooctyl ester of 3-thiohydracrylic acid, n-dodecyl mercaptan or tertiary lauryl mercaptan.
3. the preparation method of aqueous dual-component acrylic acid-polyurethane resin according to claim 1 or 2, described preparation method comprises the following steps:
Prepared by component A: add propyl carbinol, glycidyl methacrylate, Resorcinol and/or MEHQ in the reactor, be heated to 50 DEG C, drips monoethanolamine and/or n-Butyl Amine 99, within 1 ~ 2 hour, drips off, and 48 ~ 52 DEG C are incubated 2 hours; Be warming up to 70 ~ 75 DEG C, be incubated 3 ~ 4 hours, discharging, and with methyl methacrylate and/or isobornyl methacrylate, butyl acrylate and/or butyl methacrylate and/or lauryl acid esters, Hydroxyethyl acrylate, molecular weight regulator, Diisopropyl azodicarboxylate, dimethyl formamide is mixed with mixed solution; In another reactor, add ethylene glycol monobutyl ether and/or propylene glycol monomethyl ether, be heated to 110 DEG C ~ 115 DEG C, start to drip mixed solution, within 3 ~ 4 hours, drip off, be incubated 2 ~ 3 hours; Add Diisopropyl azodicarboxylate, be incubated 1 ~ 2 hour, be cooled to 90 ~ 100 DEG C, vacuumize except partial solvent, add neutralizing agent, water, adjust PH to be 6 ~ 7, cold filtration discharging is component A;
Prepared by B component: add butanone and/or ethyl acetate in the reactor, hexahydrophthalic acid glycidyl ester and/or tetrahydrophthalic acid glycidyl ester, be heated to 40 DEG C under agitation condition, start to drip monoethanolamine and/or n-Butyl Amine 99, temperature is 40 ~ 43 DEG C, within 1 ~ 1.5 hour, drips off; Be warming up to 50 ~ 53 DEG C after dripping off, be incubated 2 hours; Heat up 70 ~ 75 DEG C, be incubated 3 ~ 4 hours; Be cooled to 40 DEG C, start IPDI and/or HDI of dropping 1-Methoxy-2-propyl acetate dilution, within 2 ~ 3 hours, drip off, after dripping off, 39 ~ 42 DEG C are incubated 2 hours; Be warming up to 45 ~ 49 DEG C, be incubated 3 hours; Heat up 60 ~ 64 DEG C, be incubated 3 hours, survey NCO content, later survey per hour nco value, reacts completely to nco value <0.5; Vacuumize remove portion solvent, add acid acceptor, ethylene glycol monobutyl ether and/or ethylene glycol, water, adjust PH to be 6 ~ 6.5, cold filtration discharging is B component;
Described A composition and described composition B are mixed by formula.
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CN201310499952.8A CN103554412B (en) | 2013-10-22 | 2013-10-22 | A kind of aqueous dual-component acrylic acid-polyurethane resin and preparation method thereof |
PCT/CN2014/089100 WO2015058679A1 (en) | 2013-10-22 | 2014-10-21 | Aqueous bicomponent acrylic acid-polyurethane resin and preparation method therefor |
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CN103554412B (en) * | 2013-10-22 | 2015-08-05 | 北京金汇利应用化工制品有限公司 | A kind of aqueous dual-component acrylic acid-polyurethane resin and preparation method thereof |
CN104893527B (en) * | 2015-06-09 | 2017-11-03 | 浩力森涂料(上海)有限公司 | A kind of aqueous polyurethane coating for improving limiting film thickness and preparation method thereof |
CN105838223A (en) * | 2016-06-13 | 2016-08-10 | 四川颜鼎水性环保漆科技有限公司 | Aqueous double-ingredient polyurethane paint without limit film thickness and preparation method thereof |
CN113788918A (en) * | 2021-10-15 | 2021-12-14 | 湖北天鹅科技有限公司 | Primer-topcoat integrated electrophoretic paint wear-resistant resin and preparation method thereof |
WO2024138658A1 (en) * | 2022-12-30 | 2024-07-04 | 中国船舶集团有限公司第七〇七研究所 | Block-structure uv adhesive for sensing coil, and preparation method therefor |
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CN101914185A (en) * | 2010-09-08 | 2010-12-15 | 廊坊金汇利工业涂料有限公司 | Hydroxy acrylic resin aqueous dispersion and water-based coating prepared therefrom |
CN101921374A (en) * | 2009-06-12 | 2010-12-22 | 成都市新津托展油墨有限公司 | Preparation method of polyacrylate-polyurethane resin binder for single-fluid general plastic gravure alcohol-soluble and water-soluble composite ink |
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CN103554412B (en) * | 2013-10-22 | 2015-08-05 | 北京金汇利应用化工制品有限公司 | A kind of aqueous dual-component acrylic acid-polyurethane resin and preparation method thereof |
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CN101921374A (en) * | 2009-06-12 | 2010-12-22 | 成都市新津托展油墨有限公司 | Preparation method of polyacrylate-polyurethane resin binder for single-fluid general plastic gravure alcohol-soluble and water-soluble composite ink |
CN101914185A (en) * | 2010-09-08 | 2010-12-15 | 廊坊金汇利工业涂料有限公司 | Hydroxy acrylic resin aqueous dispersion and water-based coating prepared therefrom |
CN102585650A (en) * | 2011-12-30 | 2012-07-18 | 江苏创基新材料有限公司 | High-silicon-content organic silicon-polyurethane-acrylate composite coating agent and preparation method thereof |
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