CN111205431B - Polyurethane resin and preparation method and application thereof - Google Patents
Polyurethane resin and preparation method and application thereof Download PDFInfo
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- CN111205431B CN111205431B CN202010122565.2A CN202010122565A CN111205431B CN 111205431 B CN111205431 B CN 111205431B CN 202010122565 A CN202010122565 A CN 202010122565A CN 111205431 B CN111205431 B CN 111205431B
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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
- C08G18/675—Low-molecular-weight compounds
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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
- C08G18/58—Epoxy resins
- C08G18/584—Epoxy resins having nitrogen
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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
- C08G18/6705—Unsaturated polymers not provided for in the groups C08G18/671, C08G18/6795, C08G18/68 or C08G18/69
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
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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
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
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Abstract
The invention discloses a polyurethane resin and a preparation method and application thereof. The polyurethane resin is prepared from the following components in parts by mass: 2-10 parts of alkylamine modified epoxy resin, 50-90 parts of castor oil modified glycol, 10-35 parts of isocyanate and 5-40 parts of allyl ether. The application of the polyurethane resin in preparing paint is also disclosed. The polyurethane resin is a solvent-free product, and the preparation method has the advantages of less chemical raw materials and environmental friendliness. The polyurethane resin is used for preparing the coating, no additional solvent is needed during construction, no VOC is generated, and the comprehensive performance is excellent. Compared with the existing single-component system, the product performance of the invention is better; compared with a double-component system, the product of the invention can achieve high gloss and fullness as same as the double-component system, does not need to consider the accuracy of proportioning and the operation window period, can be used for a long time, and has wide application prospect.
Description
Technical Field
The invention relates to the technical field of polyurethane, in particular to solvent-free polyurethane resin and a preparation method and application thereof.
Background
With the growing awareness of environmental protection and the perfection of laws and regulations, the use of solvent-based system coatings for light corrosion protection is greatly hindered, and although water-based coatings are developed vigorously, the performance of the water-based coatings is not nearly different from that of solvent-based coatings due to the existence of some hydrophilic groups, and the water-based coatings pollute water sources and soil and are damaged greatly if the water-based coatings are not treated well. Therefore, it is important to develop a solvent-free low-viscosity eco-friendly resin with high performance.
In the prior art, CN106995651A mentions that epoxy resin and thermosetting acrylic resin are used for blending modification of polyurethane resin, and graphene pre-powder is used for obtaining a coating with good salt fog resistance. CN104017532A discloses that an agent a is modified by epoxy resin to obtain a polyurethane cured resin; the agent B is a diluent of the catalyst, a layer of glue is coated on the substrate in a rolling way, and the amount of the sprayed catalyst B is adjusted according to the requirement, so that the moisture curing glue with controllable operation period is obtained. CN105419714A discloses that a component A is obtained by mixing an epoxy resin curing agent MeTHPA and polyether polyol, and then a polyurethane NCO-terminated prepolymer is mixed with epoxy resin to obtain an NCO-terminated prepolymer which is used as a curing agent to obtain a coating with excellent performance. CN103059278A modifies alkyd resin by using drying or non-drying vegetable oil to obtain light-colored alkyd resin.
The prior art mainly uses a solvent-free two-component system, so that workers are easy to cause improper proportion in actual operation or generate bubbles when the humidity is high, and a cured product can not meet the set requirement. And the performance of a single-component system is not easy to reach the performance of a double-component product, and a large amount of organic solvent is often needed to adjust the viscosity in the construction and paint preparation processes, so that the body damage of workers and the environment unfriendliness are caused. Therefore, there is a need for improved studies on polyurethane resins.
Disclosure of Invention
In order to overcome the problems of the prior art, the invention aims at providing a solvent-free polyurethane resin, the invention aims at providing a preparation method of the polyurethane resin, and the invention aims at providing the application of the polyurethane resin.
The invention concept of the invention is as follows: part of epoxy groups of the epoxy resin are attacked by alkylamine to obtain a modified epoxy resin. The modified epoxy resin, castor oil modified diol, diisocyanate and allyl ether are used for combined modification to prepare the air-dried multiple-modified solvent-free low-viscosity polyurethane resin.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the invention provides polyurethane resin which is prepared from the following components in parts by mass: 2-10 parts of alkylamine modified epoxy resin, 50-90 parts of castor oil modified glycol, 10-35 parts of isocyanate and 5-40 parts of allyl ether.
Preferably, the polyurethane resin is prepared from the following components in parts by mass: 4-6 parts of alkylamine modified epoxy resin, 55-85 parts of castor oil modified glycol, 18-34 parts of isocyanate and 15-39 parts of allyl ether.
Preferably, in the polyurethane resin, the alkylamine modified epoxy resin is prepared by mixing C12-C22 alkylamine and epoxy resin according to the mass ratio of 1: (12-20) reacting.
Preferably, the alkylamine-modified epoxy resin is prepared by the following method: mixing epoxy resin with alkylamine of C12-C22, and reacting at 60-90 ℃; further preferably, the reaction conditions are: firstly reacting for 0.5-1.5 h at 60-70 ℃, and then heating to 80-90 ℃ for reacting for 1.5-2.5 h; during the reaction, C12-C22 alkylamine is dropped into the epoxy resin for mixing reaction.
Preferably, in the alkylamine-modified epoxy resin, the mass ratio of the alkylamine of C12-C22 to the epoxy resin is 1: (13-15).
Preferably, in the alkylamine-modified epoxy resin, the alkylamine having a carbon number of 12 to 22 is specifically selected from hexadecylamine or octadecylamine.
Preferably, in the alkylamine-modified epoxy resin, the epoxy resin is bisphenol a type epoxy resin; further preferably, the epoxy resin is at least one selected from E-51 and E-44. The epoxy resin is liquid epoxy resin.
According to the invention, the castor oil modified diol is adopted, and the castor oil modified diol has a long-chain large alkane side group, so that the structure of the resin can be shielded, and the weather resistance and hydrolysis resistance are further improved.
Preferably, in the polyurethane resin, the number average molecular weight of the castor oil modified diol is 600-5000; more preferably, the castor oil-modified diol has a number average molecular weight of 1000 to 3000.
In the polyurethane resin, the isocyanate is diisocyanate and is at least one selected from isophorone diisocyanate (IPDI), Hexamethylene Diisocyanate (HDI), methylcyclohexane diisocyanate (HTDI), dicyclohexylmethane diisocyanate (HMDI), 1, 4-cyclohexane diisocyanate (CHDI), HDI trimer and IPDI trimer; more preferably, the isocyanate is at least one selected from isophorone diisocyanate and hexamethylene diisocyanate. The use of these isocyanates makes it possible to obtain products having a lower viscosity.
Preferably, in the polyurethane resin, the allyl ether is at least one selected from trimethylolpropane monoallyl ether (TMPME), trimethylolpropane diallyl ether (TMPDE), glycerol diallyl ether, ethylene glycol monoallyl ether, diethylene glycol monoallyl ether, propylene glycol monoallyl ether, dipropylene glycol monoallyl ether, and pentaerythritol triallyl ether; further preferably, the allyl ether is at least one selected from trimethylolpropane monoallyl ether and trimethylolpropane diallyl ether. In the invention, allyl ether is used as an air-drying monomer, and can be subjected to partial end capping treatment to realize air crosslinking.
The invention also provides a preparation method of the polyurethane resin.
The preparation method of the polyurethane resin comprises the following steps:
1) mixing alkylamine modified epoxy resin and castor oil modified diol in a reactor, and dehydrating to obtain a prepolymer;
2) adding isocyanate to react;
3) and adding allyl ether, and continuing to react to obtain the polyurethane resin.
Preferably, in the step 1) of the preparation method, the dehydration is specifically vacuum dehydration at 105-120 ℃; further preferably, the dehydration is carried out under vacuum at 110 ℃. In step 1), the dehydration time can be adjusted according to actual conditions, so as to remove water in the system, and in some specific embodiments, the dehydration time can be preferably 1.5h to 2.5 h.
Preferably, in the step 2) of the preparation method, the reaction temperature is 60-90 ℃, and the reaction time is 1-8 h; more preferably, the reaction in step 2) is carried out for 0.5-1.5 h at 60-70 ℃, and then the temperature is raised to 80-90 ℃ for 5-7 h.
Preferably, in the step 3) of the preparation method, the reaction temperature is 60-90 ℃, and the reaction time is 1-3 h; more preferably, in the step 3), the reaction temperature is 80-90 ℃, and the reaction time is 1.5-2.5 h. In some preferred embodiments of the present invention, step 3) is performed by maintaining the reaction temperature at the end of step 2) and maintaining the temperature.
The invention also provides application of the polyurethane resin.
An application of the polyurethane resin in preparing paint.
Furthermore, the polyurethane resin is used as a film forming material when being applied to preparing coatings, and can be matched with other auxiliary agents such as wetting agents, defoaming agents, thixotropic agents, catalysts, light stabilizers and the like according to actual conditions to prepare various coatings.
Preferably, when the polyurethane resin is applied to preparing the coating, the mass percent of the polyurethane in the coating is 95-98%.
In some preferred embodiments of the present invention, there is provided a coating material, which comprises the following components by mass: 95-98% of polyurethane resin, 0.1-0.5% of wetting agent, 0.1-0.5% of defoaming agent, 0.2-0.8% of thixotropic agent, 1-2% of catalyst and 0.5-1.5% of ultraviolet absorbent.
The invention has the beneficial effects that:
the polyurethane resin is a solvent-free product, and the preparation method has the advantages of less chemical raw materials and environmental friendliness. The polyurethane resin is used for preparing the coating, no additional solvent is needed during construction, no VOC is generated, and the comprehensive performance is excellent. Compared with the existing single-component system, the product performance of the invention is better; compared with a double-component system, the product of the invention can achieve high gloss and fullness as same as the double-component system, does not need to consider the accuracy of proportioning and the operation window period, can be used for a long time, and has wide application prospect.
Specifically, compared with the prior art, the invention has the following advantages:
1) the epoxy resin is modified by the hexadecylamine, which is a modified resin with excellent corrosion resistance and tolerance, so that the resin has higher salt spray resistance and hydrophobicity;
2) the invention adopts castor oil modified alcohol as a bio-based modified raw material, thereby being more environment-friendly;
3) the polyurethane system of the invention has no free NCO group, and does not generate chemical bubbles;
4) organic solvent is not required to be added during coating construction, so that the damage to the environment and the body of a constructor is avoided;
5) the requirements for operators are reduced, strict proportion is not required, and single component construction can be realized.
Detailed Description
The present invention will be described in further detail with reference to specific examples. The starting materials, reagents or apparatus used in the examples and comparative examples were obtained from conventional commercial sources or can be obtained by a method of the prior art, unless otherwise specified. Unless otherwise indicated, the testing or testing methods are conventional in the art.
Polyurethane resin example 1
The polyurethane resin is prepared from the following components in parts by mass: 5 parts of hexadecylamine modified epoxy resin, 85 parts of castor oil modified glycol (number average molecular weight 2000), 25 parts of IPDI, and 27.9 parts of trimethylolpropane diallyl ether.
In all examples, the hexadecylamine modified epoxy resin was prepared as follows: firstly, filling epoxy resin E-51 into a three-neck flask, refluxing, placing in a water bath environment at 65 ℃, dripping hexadecylamine, reacting for 1 hour, heating to 85 ℃, and reacting for 2 hours to obtain hexadecylamine modified epoxy resin. Wherein, the used E-51 part by mass is 70 parts, and the modifier hexadecylamine is 5 parts.
The preparation method of the polyurethane resin of this example is as follows:
1) according to the proportion, placing hexadecylamine modified epoxy resin and castor oil modified diol into a three-neck flask, dehydrating for 2 hours in vacuum at 110 ℃, removing water in the system, and then cooling to 65 ℃;
2) adding IPDI, reacting at 65 ℃ for 1 hour, heating to 85 ℃, and keeping the temperature for 6 hours until the NCO% reaches a theoretical value;
3) and adding trimethylolpropane diallyl ether, continuously keeping the temperature at 85 ℃ for 2 hours, and discharging to obtain the polyurethane resin.
Polyurethane resin example 2
The polyurethane resin is prepared from the following components in parts by mass: 5 parts of hexadecylamine modified epoxy resin, 85 parts of castor oil modified glycol (number average molecular weight 2000), 18 parts of IPDI, and 15 parts of trimethylolpropane diallyl ether.
The polyurethane resin of this example was prepared in substantially the same manner as in example 1, except that the additive was composed of the raw materials in this example.
Polyurethane resin example 3
The polyurethane resin is prepared from the following components in parts by mass: 5 parts of hexadecylamine modified epoxy resin, 30 parts of castor oil modified glycol (number average molecular weight 1000), 55 parts of castor oil modified glycol (number average molecular weight 2000), 34 parts of IPDI, and 38.9 parts of trimethylolpropane diallyl ether.
The polyurethane resin of this example was prepared in substantially the same manner as in example 1, except that the additive was composed of the raw materials in this example.
Comparative example 1 of polyurethane resin
The polyurethane resin is prepared from the following components in parts by mass: 85 parts of castor oil-modified diol (number average molecular weight 2000), 25 parts of IPDI, 27.9 parts of trimethylolpropane diallyl ether.
The preparation method of the polyurethane resin in this example is basically the same as that of example 1, except that the raw materials of this example constitute the additive materials, and the hexadecylamine modified epoxy resin is not required to be added to participate in the reaction.
Comparative polyurethane resin example 2
The polyurethane resin is prepared from the following components in parts by mass: 5 parts of hexadecylamine modified epoxy resin, 85 parts of polypropylene glycol PPG2000 (number average molecular weight 2000), 25 parts of IPDI, and 27.9 parts of trimethylolpropane diallyl ether.
The polyurethane resin of this example was prepared in substantially the same manner as in example 1, except that the additive was composed of the raw materials in this example.
Comparative polyurethane resin example 3
The polyurethane resin is prepared from the following components in parts by mass: 5 parts of a hexadecylamine-modified epoxy resin, 85 parts of a polycarbonate diol PCDL2000 (number average molecular weight 2000), 25 parts of IPDI, and 27.9 parts of trimethylolpropane diallyl ether.
The polyurethane resin of this example was prepared in substantially the same manner as in example 1, except that the additive was composed of the raw materials in this example.
Coating examples 1 to 3 and coating comparative examples 1 to 3
The polyurethane resins obtained in the polyurethane resin examples 1 to 3 and the polyurethane comparative examples 1 to 3 were used to prepare coating examples 1 to 3 and coating comparative examples 1 to 3, respectively. The coating comprises the following components in percentage by mass: 96.5 percent of polyurethane resin, 0.25 percent of wetting agent BYK-306, 0.25 percent of defoaming agent TEGO-900, 0.5 percent of thixotropic agent BYK-420, 1.5 percent of drier CUCAT-CS01 and 1 percent of ultraviolet absorbent UV-531.
Comparative paint example 4
This example uses a commercially available two-component system comprising component A, a hydroxy acrylic resin, 60 wt% solids; and the component B is an isocyanate curing agent with the solid content of 90 percent by weight. When in use, the component A, the component B and a diluent (benzene solvent) are mixed according to the mass ratio of 5:1:5 to prepare the two-component coating.
Comparative coating example 5
This example uses a commercially available one-component system, a self-drying alkyd paint.
The paint examples 1-3 and the paint comparative examples 1-5 were compared in performance tests, and the test results are shown in table 1.
The test methods for each index in table 1 are illustrated below:
solvent content: GB/T1725-2007;
viscosity: GB/T22235-2008, 25 ℃;
adhesion force: GB/T9286-1998;
gloss: GB/T9754-2007, 60 °;
water resistance: GB/T1733 + 1993;
salt spray resistance: ASTM B117-2011;
resistance to 5% hydrochloric acid: GB/T9274-1988;
impact resistance: GB/T1732 + 1993.
TABLE 1 paint Performance test comparison
The test results in table 1 show that: comparative example 1 had insufficient adhesion due to lack of modified epoxy resin; the comparative example 2 is prepared by adopting common polyether, and has insufficient weather resistance such as water resistance, salt mist resistance, hydrochloric acid resistance and the like; comparative example 3, which uses polycarbonate diol, has excellent performance, but high viscosity, and requires additional solvent when in use; comparative example 4 this commercially available two-component paint requires accurate metering and has operating time limitations; the commercial one-component paint of comparative example 5 was inferior in all the properties to the effects of the examples.
In conclusion, the polyurethane resin is a solvent-free product, has low viscosity (less than 5000cps at 25 ℃), has better comprehensive performance compared with the prior bi-component or single-component system, does not need to additionally increase solvent during construction, does not generate VOC, and does not need to consider the accuracy of proportioning and the operation window period. The solvent-free polyurethane resin can be applied to preparing various coatings with excellent performance and has wide application prospect.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (9)
1. A polyurethane resin characterized by: the polyurethane resin is prepared from the following components in parts by mass: 2-10 parts of alkylamine modified epoxy resin, 50-90 parts of castor oil modified glycol, 10-35 parts of isocyanate and 5-40 parts of allyl ether;
the allyl ether is selected from at least one of trimethylolpropane diallyl ether, glycerol diallyl ether, ethylene glycol monoallyl ether, diethylene glycol monoallyl ether, propylene glycol monoallyl ether, dipropylene glycol monoallyl ether and pentaerythritol triallyl ether;
the preparation method of the polyurethane resin comprises the following steps:
1) mixing alkylamine modified epoxy resin and castor oil modified diol in a reactor, and dehydrating to obtain a prepolymer;
2) adding isocyanate to react;
3) and adding allyl ether, and continuing to react to obtain the polyurethane resin.
2. The polyurethane resin according to claim 1, characterized in that: the alkylamine modified epoxy resin is prepared by reacting C12-C22 alkylamine with epoxy resin.
3. The polyurethane resin according to claim 2, characterized in that: the epoxy resin is bisphenol A type epoxy resin.
4. The polyurethane resin according to claim 1, characterized in that: the number average molecular weight of the castor oil modified diol is 600-5000.
5. The polyurethane resin according to claim 1, characterized in that: the isocyanate is selected from at least one of isophorone diisocyanate, hexamethylene diisocyanate, methylcyclohexane diisocyanate, dicyclohexylmethane diisocyanate, 1, 4-cyclohexane diisocyanate, HDI trimer and IPDI trimer.
6. A method for producing the polyurethane resin according to any one of claims 1 to 5, characterized in that: the method comprises the following steps:
1) mixing alkylamine modified epoxy resin and castor oil modified diol in a reactor, and dehydrating to obtain a prepolymer;
2) adding isocyanate to react;
3) and adding allyl ether, and continuing to react to obtain the polyurethane resin.
7. The method of claim 6, wherein: in the step 1), the dehydration is specifically vacuum dehydration at 105-120 ℃.
8. The method of claim 6, wherein: in the step 2), the reaction temperature is 60-90 ℃, and the reaction time is 1-8 h.
9. Use of the polyurethane resin according to any one of claims 1 to 5 for the preparation of a coating.
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| CN116102963B (en) * | 2022-09-09 | 2024-05-10 | 广州昊毅新材料科技股份有限公司 | Water-based bi-component coating and preparation method and application thereof |
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| CN105238256A (en) * | 2015-11-11 | 2016-01-13 | 科顺防水科技股份有限公司 | Allyl ether modified single-component polyurethane waterproof paint and preparation method thereof |
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| JP2004051925A (en) * | 2002-07-24 | 2004-02-19 | Dainippon Ink & Chem Inc | Urethane-based coating resin composition and coating material |
| CN101173124A (en) * | 2006-10-31 | 2008-05-07 | 关西涂料株式会社 | Cationic electrodeposition coating composition and articles coated with the electrodeposition coating |
| CN103059254A (en) * | 2011-10-20 | 2013-04-24 | 展辰涂料集团股份有限公司 | Water-soluble floor paint resin and application thereof |
| CN104312378A (en) * | 2014-10-09 | 2015-01-28 | 六安市微特电机有限责任公司 | High-temperature resistant solvent-free impregnating varnish and preparation method thereof |
| CN105238256A (en) * | 2015-11-11 | 2016-01-13 | 科顺防水科技股份有限公司 | Allyl ether modified single-component polyurethane waterproof paint and preparation method thereof |
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