CN109370506A - A kind of ultraviolet light solidfication water polyurethane binder and preparation method thereof - Google Patents
A kind of ultraviolet light solidfication water polyurethane binder and preparation method thereof Download PDFInfo
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- CN109370506A CN109370506A CN201811129295.7A CN201811129295A CN109370506A CN 109370506 A CN109370506 A CN 109370506A CN 201811129295 A CN201811129295 A CN 201811129295A CN 109370506 A CN109370506 A CN 109370506A
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- acrylate
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- 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
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
-
- 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
- C08G18/70—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
-
- 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
- C08G18/70—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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
Abstract
The present invention relates to a kind of ultraviolet light solidfication water polyurethane binders and preparation method thereof.Ultraviolet light solidfication water polyurethane binder of the present invention is mainly prepared by waterborne ultraviolet curing resin, ultraviolet light curing initiator, deionized water and water-soluble co-solvents；The waterborne ultraviolet curing resin mainly is synthesized to obtain by the reaction of polyether polyol, isocyanates, acrylate, photo-curing monomer and salt forming agent.The preparation method simple process of ultraviolet light solidfication water polyurethane binder of the present invention, gained ultraviolet light solidfication water polyurethane binder cured film shrinking percentage is low, bonding force is strong, high, heat-resist, VOC free the volatilization of quick solidifying, peel strength, bonding easy to use, suitable for glue film and glue film, glue film and rubber and plastic materials.
Description
Technical field
The invention belongs to technical field of chemical products, are related to a kind of binder.
Background technique
Many advantages, such as ultraviolet photo-curing cementing agent is fast, low energy consumption, environmental-friendly with its curing rate in recent years is in gluing
Agent field obtains extensive research and extension.In addition, being usually used in being bonded transparent substrate, such as: glass due to its good optical property
Glass, crystal, transparent plastic, coloured glaze, the materials such as jewel.But there are still some drawbacks for existing ultraviolet curing adhesive: such as it
Contain volatile organic compounds component in diluting monomer and other multi-functional acrylates, has to environment and human body certain
Damage, although the ultraviolet curing adhesive of high solids content can be prepared by improveing the degree of polymerization of functional polymer,
To reduce VOC discharge capacity, but since its product viscosity is to the dependence of molecular weight, low molecular weight product will lead to system viscosity mistake
Greatly, it and is difficult to adjust.Therefore the ultraviolet light solidfication water polyurethane binder of high molecular weight has become following development trend.
Summary of the invention
The present invention is intended to provide a kind of shrinking percentage is low, bonding force is strong, quick solidifying, peel strength are high, heat-resist, VOC free
Volatilization, ultraviolet light solidfication water polyurethane binder easy to use and preparation method thereof, asked with solving the prior art
Topic.
The method of the present invention be using by waterborne ultraviolet curing resin, ultraviolet light curing initiator, water-soluble co-solvents and
Deionized water is mixed and made into ultraviolet light solidfication water polyurethane binder, wherein the weight fraction ratio of various raw materials are as follows:
Waterborne ultraviolet curing resin 30~70
Ultraviolet light curing initiator 1~6
Water-soluble co-solvents 1~20
Deionized water 10~40
The preferred weight portion rate of various raw materials is
Waterborne ultraviolet curing resin 35~65
Ultraviolet light curing initiator 2~5
Water-soluble co-solvents 5~15
Deionized water 20~30
The optimum weight portion rate of raw material is
Waterborne ultraviolet curing resin 49
Ultraviolet light curing initiator 3
Water-soluble hydrotropy 9
Deionized water 27
The manufacturing technique of the present invention are as follows: take the waterborne ultraviolet curing resin of above-mentioned weight fraction ratio and molten with water-soluble co-solvents
The ultraviolet light curing initiator of solution stirs, and being eventually adding deionized water mixing, that UV-curable water-borne is made is poly-
Urethane binder.
Wherein waterborne ultraviolet curing resin is poly- by polyester polyol, isocyanates, photo-curing monomer and acrylate etc.
It closes reaction to be made, wherein above-mentioned raw materials weight fraction ratio are as follows:
Polyester polyol 20~40
Isocyanates 15~30
Acrylate 20~40
Photo-curing monomer 15~25
Salt forming agent 2~8
The optimum weight portion rate of raw material are as follows:
Polyester polyol 38
Isocyanates 25
Acrylate 29
Photo-curing monomer 19
Salt forming agent 6
Polyester polyol can be replaced by polyether polyol.
Alkenyl urethane acrylate in end is synthesized using acetone method method: firstly, more by excessive isocyanates and polyester
First alcohol synthesizes base polyurethane prepolymer for use as in 60 DEG C~90 DEG C 2~5h of reaction, and acrylate is then added and reacts at 30 DEG C~50 DEG C
1h~3h is added salt forming agent and deionized water obtains the polyurethane propylene in water-soluble finally by the salt-forming reaction of hydroxyl
Acid esters, i.e. waterborne ultraviolet curing resin.
Wherein water-soluble photoinitiator is derivative by arone class, including benzophenone derivative, thioxanthone derivative, alkyl arone
It is selected in object, benzil derivatives.Currently preferred photoinitiator is the hydroxy-cyclohexyl phenyl ketone of alkyl arone class.
Water-soluble additive may is that ethyl alcohol, acetone, n-butanol, propylene-glycol ethyl ether, propandiol butyl ether, N, N- dimethyl methyl
One of amide, DMAC N,N' dimethyl acetamide are several.Currently preferred water-soluble additive is acetone and N, N- bis-
Methylacetamide.
Acrylate may is that methyl acrylate, ethyl acrylate, butyl acrylate, 2- methyl methacrylate and 2-
One or more of ethyl methacrylate.Currently preferred acrylate is butyl acrylate.
Salt forming agent can be one or more of triethylamine, hydrochloric acid, acetic acid kind propylene oxide.It is currently preferred at salt
Agent is triethylamine.
By the Hg lamp irradiation of 500W when ultraviolet light solidfication water polyurethane binder made of the present invention uses, when dry
Between be 10~15 seconds, solidification effect meets national standard, to human body and environment without any harm.
Specific embodiment:
Example 1
1. 26 grams of isophorone diisocyanate and 40 grams of polytetrahydrofuran ether glycol through dehydration are added at 80 DEG C
In 500ml three-necked flask equipped with agitating paddle, condenser pipe and nitrogen protection, be added 0.02 gram of dibutyl tin dilaurate be used as draw
Agent is sent out, keeps the temperature 40~50 minutes at 70~80 DEG C.
2. 7 grams of 2,2- dihydromethyl propionic acids and a small amount of n,N-dimethylacetamide is added, react 2 hours, it can during reaction
To use acetone to adjust viscosity.
3. cooling, makes temperature in three-necked flask are as follows: 40~48 DEG C.
4. being added 7 grams to defend tetrol triacrylate and 29 grams of butyl acrylates season the reaction was continued 30 minutes.
5. 20 grams are added after 30 minutes double defends six acrylate of tetrol and 20 grams of dipropylene glycol diacrylates season and will be warm
Degree is adjusted to 60 DEG C, reacts 2 hours.
6. after 2 hours, it is cooled to 40 DEG C of addition triethylamines and a small amount of deionized water neutralizes, after being uniformly dispersed, consolidate
The UV-Curing Waterborne Resin that content is 80% or so.
Example 2
1. 16.3 grams of toluene di-isocyanate(TDI)s (TDI) and 40 grams of polytetrahydrofuran ether glycol (PTMG) through dehydration are added
Enter into the 500ml three-necked flask equipped with agitating paddle, condenser pipe and nitrogen protection, 0.02 gram of dibutyl tin dilaurate is added and uses
Make initiator, 3 grams of organo montmorillonites are added and are stirred 40~50 minutes at 90 DEG C.
2. 5 grams of 2,2- dihydromethyl propionic acids and a small amount of n,N-dimethylacetamide is added, react 1 hour, it can during reaction
To use acetone to adjust viscosity.
3. being cooled to 50 DEG C of additions, 31 grams of hy-droxybutyls, 80 DEG C are warming up to, is reacted two hours
4. being cooled to 40 DEG C, being added in triethylamine and a small amount of deionized water and dispersing, the photocuring for obtaining solid content 75% is aqueous
Resin
Example 3
1. by 43 grams of isophorone diisocyanate (IPDI) and 40 grams of polytetrahydrofuran ether glycol (PTMG) through dehydration
It is added in the 500ml three-necked flask at 80 DEG C equipped with agitating paddle, condenser pipe and nitrogen protection, 0.02 gram of tin dilaurate two is added
Butyl tin is used as initiator, keeps the temperature 40~50 minutes at 70~80 DEG C.
2. 7 grams of 2,2- dihydromethyl propionic acids and a small amount of n,N-dimethylacetamide is added, react 2 hours, it can during reaction
To use acetone to adjust viscosity.
3. cooling, makes temperature in three-necked flask are as follows: 40~48 DEG C.
4. 25 grams of hy-droxybutyls are added, and the reaction was continued 30 minutes
5. 20 grams are added after 30 minutes double defends six acrylate of tetrol and 20 grams of dipropylene glycol diacrylates season and by temperature tune
Section reacts 2 hours to 60 DEG C.
6. after 2 hours, it is cooled to 40 DEG C of addition triethylamines and a small amount of deionized water neutralizes, after being uniformly dispersed, consolidate
The UV-Curing Waterborne Resin that content is 85% or so.
Example 4
By in 69 grams of addition mixing vessels of ultraviolet light solidfication water polyurethane acrylate obtained in examples detailed above 1, unlatching is stirred
Mix, while 3 grams of photoinitiators, 27 grams of deionized waters and 9 grams of n,N-dimethylacetamide be added, stirring to be uniformly mixed to get
To ultraviolet light solidfication water polyurethane binder.
This binder cementability is excellent, and has rapid curing nature, while to bases such as glass, product of rubber and plastic and glue film products
Adhesive force is good for material.
Claims (10)
1. a kind of preparation method of ultraviolet light solidfication water polyurethane binder, which is characterized in that by UV-curable waterborne tree
Rouge, ultraviolet light curing initiator, water-soluble co-solvents and deionized water are mixed, wherein each raw material weight number ratio is as follows:
Waterborne ultraviolet curing resin 30~70
Ultraviolet light curing initiator 1~6
Water-soluble co-solvents 1~20
Deionized water 10~40
Wherein waterborne ultraviolet curing resin is made of polymerization reactions such as polyester polyol, isocyanates, acrylate, wherein on
State material weight portion rate are as follows:
Polyether polyol 10~50
Isocyanates 15~35
Acrylate 10~20
Photo-curing monomer 10~30
Salt forming agent 1~10
Alkenyl urethane acrylate in end is synthesized using acetone method method: firstly, passing through excessive isocyanates and polyester polyol
In 60 DEG C~90 DEG C 2~4h of reaction, synthesize base polyurethane prepolymer for use as, then be added acrylate 30 DEG C~50 DEG C reaction 1h~
3h is added salt forming agent and deionized water obtains the urethane acrylate in water-soluble finally by the salt-forming reaction of hydroxyl,
That is waterborne ultraviolet curing resin.
2. the binder belonging to according to claim 1, it is characterised in that: the weight fraction ratio of raw material are as follows:
Waterborne ultraviolet curing resin 35~65
Ultraviolet light curing initiator 2~5
Water-soluble co-solvents 5~15
Deionized water 20~30.
3. the binder belonging to according to claim 1, it is characterised in that: waterborne ultraviolet curing resin is by polyester polyol, different
Cyanate, acrylic ester polymerization reaction are made, the weight fraction ratio of above-mentioned material are as follows:
Polyester polyol 20~40
Isocyanates 15~30
Acrylate 20~40
Photo-curing monomer 15~25
Salt forming agent 2~8.
4. binder according to claim 1, it is characterised in that: in waterborne ultraviolet curing resin, polyester polyol by
Polyether polyol substitution.
5. binder according to claim 1, it is characterised in that: the water-soluble photoinitiator is by arone class, including two
Benzophenone derivatives, alkyl arone derivative, select in benzil derivatives thioxanthone derivative.
6. binder according to claim 1, which is characterized in that the water-soluble additive may is that ethyl alcohol, acetone,
One of n-butanol, propylene-glycol ethyl ether, propandiol butyl ether, N,N-dimethylformamide, DMAC N,N' dimethyl acetamide are several
Kind.
7. binder according to claim 1, which is characterized in that the salt forming agent can be triethylamine, hydrochloric acid, acetic acid
One or more of kind propylene oxide.
8. binder according to claim 1, it is characterised in that: the acrylate can be methyl acrylate, third
One or more of olefin(e) acid ethyl ester, butyl acrylate, 2- methyl methacrylate and ethyl 2-methacrylate.
9. binder according to claim 1, it is characterised in that: the photo-curing monomer, which can be, double defends tetrol six season
One or more of acrylate and dipropylene glycol diacrylate.
10. the preparation method of binder according to claim 1, which is characterized in that include the following:
Step 1: alkenyl urethane acrylate in end is synthesized using acetone method method: firstly, passing through excessive isocyanates and polyester
Polyalcohol synthesizes base polyurethane prepolymer for use as in 60 DEG C~90 DEG C 2~5h of reaction, and photo-curing monomer then is added and acrylate exists
30 DEG C~50 DEG C reaction 1h~3h, finally by the salt-forming reaction of hydroxyl, be added salt forming agent and deionized water obtain it is water-soluble
In urethane acrylate, i.e. waterborne ultraviolet curing resin；
Step 2: aqueous UV-cured resin and with water-soluble co-solvents dissolve ultraviolet light curing initiator be sufficiently stirred
Uniformly, it is eventually adding deionized water mixing and ultraviolet light solidfication water polyurethane binder is made.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811129295.7A CN109370506A (en) | 2018-09-27 | 2018-09-27 | A kind of ultraviolet light solidfication water polyurethane binder and preparation method thereof |
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| CN201811129295.7A CN109370506A (en) | 2018-09-27 | 2018-09-27 | A kind of ultraviolet light solidfication water polyurethane binder and preparation method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109868110A (en) * | 2019-02-25 | 2019-06-11 | 江苏大学 | A kind of veneer application type flexibility glue and preparation method thereof and implementing process |
| CN110791251A (en) * | 2019-10-30 | 2020-02-14 | 广东普赛达密封粘胶有限公司 | Acrylate modified polyurethane sealant and preparation method thereof |
| WO2020181454A1 (en) * | 2019-03-11 | 2020-09-17 | 福建华峰新材料有限公司 | Composite cloth and preparation method therefor |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101372530A (en) * | 2008-08-08 | 2009-02-25 | 中国工程物理研究院化工材料研究所 | Aqueous photo-curing polyurethane resin and preparation thereof |
| CN102399525A (en) * | 2010-09-10 | 2012-04-04 | 宏峰行化工(深圳)有限公司 | Flexible package composite membrane ultraviolet cured water-based adhesive and preparation method thereof |
| CN104031227A (en) * | 2013-03-07 | 2014-09-10 | 上海恩多水性树脂有限公司 | Aqueous polyurethane preparation method |
-
2018
- 2018-09-27 CN CN201811129295.7A patent/CN109370506A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101372530A (en) * | 2008-08-08 | 2009-02-25 | 中国工程物理研究院化工材料研究所 | Aqueous photo-curing polyurethane resin and preparation thereof |
| CN102399525A (en) * | 2010-09-10 | 2012-04-04 | 宏峰行化工(深圳)有限公司 | Flexible package composite membrane ultraviolet cured water-based adhesive and preparation method thereof |
| CN104031227A (en) * | 2013-03-07 | 2014-09-10 | 上海恩多水性树脂有限公司 | Aqueous polyurethane preparation method |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109868110A (en) * | 2019-02-25 | 2019-06-11 | 江苏大学 | A kind of veneer application type flexibility glue and preparation method thereof and implementing process |
| WO2020181454A1 (en) * | 2019-03-11 | 2020-09-17 | 福建华峰新材料有限公司 | Composite cloth and preparation method therefor |
| CN110791251A (en) * | 2019-10-30 | 2020-02-14 | 广东普赛达密封粘胶有限公司 | Acrylate modified polyurethane sealant and preparation method thereof |
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