CN107083228B - Single-component transparent non-yellowing polyurethane sealant and preparation method thereof - Google Patents
Single-component transparent non-yellowing polyurethane sealant and preparation method thereof Download PDFInfo
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/08—Polyurethanes from polyethers
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- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3234—Polyamines cycloaliphatic
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- 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
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
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- 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
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/02—Polyureas
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
Abstract
The invention relates to a single-component transparent non-yellowing polyurethane sealant and a preparation method thereof, wherein the single-component transparent non-yellowing polyurethane sealant comprises the following components in parts by weight: 50-75 of an allophanate polyurethane prepolymer; 5-15 parts of gas-phase silicon; 20-40 parts of plasticizer; 0.1-2 parts of latent curing agent; 0.1-0.5 of catalyst. Preparation: adding a plasticizer, gas-phase silicon and a latent curing agent into the allophanate polyurethane prepolymer, stirring and dispersing for 2 hours under a vacuum condition, and controlling the temperature to be lower than 50 ℃; and after stirring, adding a catalyst, and stirring and dispersing for 0.5h under a vacuum condition to obtain the catalyst. The sealant is one-component moisture curing, has short curing time, high transparency, no VOC volatile component, difficult bubble generation and high bonding strength, and is suitable for bonding glass and transparent plastics; it can also be used for bonding and sealing of lamp decoration and lamps.
Description
Technical Field
The invention belongs to the field of polyurethane sealant and preparation thereof, and particularly relates to a single-component transparent non-yellowing polyurethane sealant and a preparation method thereof.
Background
The polyurethane sealant has a large number of applications in the automobile industry, the building and the decoration, and at present, the polyurethane sealant is divided into a single component and a double component according to the components, and is divided into polyurethane and modified polyurethane sealants (generally, silicone modification, epoxy modification, mercaptan modification and the like) according to the components. The single-component sealant is convenient to use, free of VOC volatilization, multiple in types of bonding materials, good in elasticity and low in shrinkage rate, and is favored by markets and constructors.
However, the common single-component polyurethane sealant has the defects of easy yellowing, poor transparency and the like, and the defects of long curing time, easy foaming, poor bonding strength and the like in the production of the polyurethane sealant by non-yellowing isocyanate for adjusting the formula of the common polyurethane sealant by manufacturers.
The polyether amine and the micromolecule chain extender with high activity are introduced from the formula to produce the polyurethane sealant by matching the polyether amine and the micromolecule chain extender with the non-yellowing isocyanate, so that the curing speed is increased, the bonding strength is increased, allophanate is generated by reaction, the mechanical strength and the toughness are high, and the transparency and the yellowing resistance of the product are also high.
The invention is suitable for bonding glass and transparent plastics; it can also be used for bonding and sealing of lamp decoration and lamps.
Disclosure of Invention
The invention aims to solve the technical problem of providing a single-component transparent non-yellowing polyurethane sealant and a preparation method thereof, aiming at overcoming the defects of the traditional sealant mentioned in the description, the invention optimizes and improves isocyanate, polyol polyamine and other fillers, and provides a synthetic method of the single-component non-yellowing polyurethane sealant.
The invention relates to a single-component transparent non-yellowing polyurethane sealant which comprises the following components in parts by weight:
the allophanate polyurethane prepolymer comprises the following raw materials in parts by weight:
50-90 parts of amino-terminated polyoxypropylene ether;
10-50 parts of aliphatic diol or diamine mixture;
30-50 parts of isocyanate.
The allophanate polyurethane prepolymer is polymerized by non-yellowing isocyanate and one or more of amino-terminated polyoxypropylene ether, aliphatic diol or diamine.
The isocyanate is one or more of 4, 4-diphenylmethane diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, dicycloethyl methane diisocyanate, xylylene diisocyanate, cyclohexane dimethylene diisocyanate and methyl cyclohexyl diisocyanate; the amino-terminated polyoxypropylene ether is one or more of polyetheramines with the molecular weight Mn of 230-5000 and the functionality of 2.
The aliphatic diol is one or more of ethylene glycol, propylene glycol, butanediol, pentanediol, neopentyl glycol, methyl propylene glycol, hexanediol, diethylene glycol and triethylene glycol; the aliphatic diamine is one or more of hexamethylene diamine, isophorone diamine, trimethyl hexamethylene diamine and dimethyl diamino dicyclohexyl methane.
The gas-phase silicon is gas-phase silicon dioxide; the plasticizer is one or more of diethyl phthalate, dibutyl phthalate, dioctyl adipate, dibutyl adipate, cyclohexane 1, 2-diisononyl phthalate, glycol benzoate and triphenyl phosphate.
The latent curing agent is one or more of ALT-101, ALT-102, ALT-201, ALT-401, ALT-402 and ALT-403; the catalyst is one or more of triethylene diamine, bis (dimethylaminoethyl) ether, dibutyltin dilaurate, stannous octoate, zinc isooctanoate and bismuth isooctanoate.
The invention discloses a preparation method of a single-component transparent non-yellowing polyurethane sealant, which comprises the following steps:
(1) adding a plasticizer, gas-phase silicon and a latent curing agent into the allophanate polyurethane prepolymer, stirring and dispersing for 2 hours under a vacuum condition, and controlling the temperature to be lower than 50 ℃;
(2) and after stirring, adding a catalyst, and stirring and dispersing for 0.5h under a vacuum condition to obtain the single-component transparent non-yellowing polyurethane sealant.
The preparation of the allophanate polyurethane prepolymer specifically comprises the following steps: mixing amino-terminated polyoxypropylene ether, aliphatic diol or diamine mixtureUniformly mixing for later use, weighing the non-yellowing isocyanate, placing the non-yellowing isocyanate in a reaction container, slowly dripping the mixed polyether amine and aliphatic diol or diamine into the non-yellowing isocyanate, continuously stirring, and introducing N into the non-yellowing isocyanate2And (3) protecting, cooling the outside by using ice water, keeping the internal reaction temperature not higher than 50 ℃, continuing stirring and reacting for 0.5-2 h after the dropwise adding is finished, testing the NCO content after the reaction is finished, and obtaining the allophanate prepolymer after the NCO content is qualified.
The NCO content is 2-10% when the NCO content is qualified.
Advantageous effects
(1) The invention optimizes and improves isocyanate, polyol polyamine and other fillers, provides a synthetic method of the single-component non-yellowing polyurethane sealant, and overcomes the defects of the traditional sealant;
(2) the sealant is one-component moisture curing, has short curing time, high transparency, no VOC volatile component, difficult bubble generation and high bonding strength, and is suitable for bonding glass and transparent plastics; it can also be used for bonding and sealing of lamp decoration and lamps.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Example 1
Placing 581.2g of HMDI in a reaction container, heating until the mixture is completely clear and transparent, and cooling to room temperature;
366.5g of polyetheramine D230 and diaminodicyclohexylmethane (PACM) are mixed and stirred uniformly;
introducing N into the reaction vessel2Placing the reaction container in ice water, slowly dropwise adding the mixed D230 and PACM into HMDI, and continuously stirring in vacuum;
controlling the reaction temperature to be 40-50 ℃, and preserving heat for 2 hours after the dropwise addition is finished;
after the heat preservation is finished, NCO detection is carried out on the product, and the actual NCO is 3 percent;
placing 650g of the polyurea-urethane prepolymer after the reaction is completed in a reaction vessel;
adding 100g of fumed silica, 250g of dimethyl ethylene glycol phthalate (DMEP) and ALT-4012 g of latent curing agent into a reaction container, starting stirring under a vacuum condition, and controlling the temperature to be 40-50 ℃;
after stirring for 2h, adding 0.2g of catalyst triethylenediamine into the reaction vessel, and stirring for 0.5h again;
and after stirring, obtaining the single-component non-yellowing polyurethane sealant sample 1.
Example 2
Placing 436.9g of IPDI in a reaction vessel, heating until the mixture is completely clear and transparent, and cooling to room temperature;
242.7g of polyetheramine D400 and isophorone diamine (IPDA) are mixed and then stirred uniformly;
introducing N into the reaction vessel2Placing the reaction container in ice water, slowly dropwise adding the mixed D400 and IPDA into IPDI, and continuously stirring in vacuum;
controlling the reaction temperature to be 40-50 ℃, and preserving heat for 2 hours after the dropwise addition is finished;
after the heat preservation is finished, NCO detection is carried out on the product, and the actual NCO is 3.5 percent;
placing 550g of polyurea-urethane prepolymer after the reaction is finished in a reaction vessel;
adding 100g of fumed silica, 350g of dimethyl ethylene glycol phthalate (DMEP) and ALT-1011 g of latent curing agent into a reaction container, starting stirring under a vacuum condition, and controlling the temperature to be 40-50 ℃;
after stirring for 2h, adding 0.5g of catalyst triethylenediamine into the reaction vessel, and stirring for 0.5h again;
and after stirring, obtaining a single-component non-yellowing polyurethane sealant sample 2.
The test results are shown in the following table:
| product type | Sample 1 | Sample 2 |
| Product appearance | Colorless and transparent | Colorless and transparent |
| Surface drying time/min | 12 | 10 |
| Appearance of the article | Colorless and transparent | Colorless and transparent |
| Product appearance/90 day sunlight irradiation | Colorless and transparent | Colorless and transparent |
| hardness/Shore A of the article | 46 | 50 |
| Tensile strength/Mpa | 8.2 | 7.6 |
| Tensile elongation/% | 623 | 597 |
| Tear Strength/N/mm | 32 | 36 |
| Adhesive strength/Mpa | 7.5 | 7.1 |
Some of the test criteria involved in the present invention are as follows:
aromatic isocyanate part 4 for production of GB/T12009.4-2016 Plastic polyurethane: determination of the isocyanate content
Determination of tensile stress strain performance of GB/T528-2009 vulcanized rubber or thermoplastic rubber
Determination of GB/T529-2008-type vulcanized rubber or thermoplastic rubber tear strength
GB/T531-2008-one vulcanized rubber or thermoplastic rubber indentation hardness test method
Method for measuring tensile shear strength of adhesion of vulcanized rubber and metal in GB/T13936-
Claims (6)
1. The single-component transparent non-yellowing moisture curing polyurethane sealant is characterized in that: the components by weight portion are as follows:
50-75 parts of allophanate polyurethane prepolymer;
5-15 parts of gas-phase silicon;
20-40 parts of a plasticizer;
0.1-2 parts of latent curing agent;
0.1-0.5 part of catalyst;
wherein the latent curing agent is one of ALT-101, ALT-102, ALT-201, ALT-401, ALT-402 and ALT-403; wherein the NCO content in the allophanate polyurethane prepolymer is 2-10%; the allophanate prepolymer is prepared by polymerizing non-yellowing isocyanate, polyether amine and diamine; wherein the polyetheramine is polyetheramine D400 or D230; the diamine is aliphatic diamine, and the aliphatic diamine is one or more of hexamethylene diamine, isophorone diamine, trimethyl hexamethylene diamine and dimethyl diamino dicyclohexyl methane.
2. The one-component transparent non-yellowing moisture-curable polyurethane sealant according to claim 1, which is characterized in that: the isocyanate is one or more of isophorone diisocyanate, hexamethylene diisocyanate, cyclohexane dimethylene diisocyanate and methyl cyclohexyl diisocyanate.
3. The one-component transparent non-yellowing moisture-curable polyurethane sealant according to claim 1, which is characterized in that: the gas-phase silicon is gas-phase silicon dioxide; the plasticizer is one or more of diethyl phthalate, dibutyl phthalate, dioctyl adipate, dibutyl adipate, cyclohexane 1, 2-diisononyl phthalate, glycol benzoate and triphenyl phosphate.
4. The one-component transparent non-yellowing moisture-curable polyurethane sealant according to claim 1, which is characterized in that: the catalyst is one or more of triethylene diamine, bis (dimethylaminoethyl) ether, dibutyltin dilaurate, stannous octoate, zinc isooctoate and bismuth isooctanoate.
5. A method of preparing a one-component transparent non-yellowing moisture-curable polyurethane sealant according to claim 1, comprising:
(1) adding a plasticizer, gas-phase silicon and a latent curing agent into the allophanate polyurethane prepolymer, stirring and dispersing for 0.5-2 h under a vacuum condition, and controlling the temperature to be lower than 50 ℃;
(2) and after stirring, adding a catalyst, and stirring and dispersing for 0.5-2 hours under a vacuum condition to obtain the single-component transparent non-yellowing polyurethane sealant.
6. The preparation method of the one-component transparent non-yellowing moisture-curable polyurethane sealant according to claim 5, characterized in that: the preparation of the allophanate polyurethane prepolymer in the step (1) specifically comprises the following steps: uniformly mixing the mixture of polyether amine and aliphatic diamine, dripping the mixture into non-yellowing isocyanate, continuously stirring, and introducing N into the mixture2Protecting, cooling the outside by using ice water, keeping the internal reaction temperature not higher than 50 ℃, continuing stirring and reacting for 0.5-2 h after the dripping is finished, testing the NCO content after the reaction is finished, and obtaining the allophanate polyurethane prepolymer after the NCO content is qualified; wherein the NCO content is 2-10% when qualified.
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| AU2020220093A1 (en) * | 2019-08-26 | 2021-03-18 | Gcp Applied Technologies Inc. | Penetrating single component prepolymer system |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101415791A (en) * | 2006-02-09 | 2009-04-22 | Sika技术股份公司 | One-part type heat curable composition |
| CN106543409A (en) * | 2016-11-03 | 2017-03-29 | 高鼎精细化工(昆山)有限公司 | Moisture-curable reaction type polyurethane hot-melt adhesive and preparation method thereof, using method and purposes |
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| CN103819647B (en) * | 2014-03-06 | 2016-02-10 | 河北宇阳泽丽防水材料有限公司 | A kind of moisture curing single-component exposed type urethane and preparation method thereof |
| CN106560497B (en) * | 2016-10-31 | 2020-10-27 | 湖南神力铃胶粘剂制造有限公司 | Anti-yellowing and fast-curing stone repair face adhesive as well as preparation method and use method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101415791A (en) * | 2006-02-09 | 2009-04-22 | Sika技术股份公司 | One-part type heat curable composition |
| CN106543409A (en) * | 2016-11-03 | 2017-03-29 | 高鼎精细化工(昆山)有限公司 | Moisture-curable reaction type polyurethane hot-melt adhesive and preparation method thereof, using method and purposes |
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| CN107083228A (en) | 2017-08-22 |
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