CN107446483B - Ultraviolet light/moisture dual cure resin and its preparation method and application - Google Patents
Ultraviolet light/moisture dual cure resin and its preparation method and application Download PDFInfo
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- CN107446483B CN107446483B CN201710187834.1A CN201710187834A CN107446483B CN 107446483 B CN107446483 B CN 107446483B CN 201710187834 A CN201710187834 A CN 201710187834A CN 107446483 B CN107446483 B CN 107446483B
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- ultraviolet light
- dual cure
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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
-
- 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
-
- 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
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention relates to a kind of ultraviolet light/moisture dual cure resin and its preparation method and application, which includes the following steps: the preparation of (1) prepolymer A: catalyst and polymerization inhibitor catalysis acrylic ester compound is added and 'beta '-ketoester carries out Michael addition reaction；(2) preparation of prepolymer B: polyester diol is heated to 70~90 DEG C, catalyst and aliphatic diisocyanate is added, is stirred to react 2~3 hours；(3) ultraviolet light/moisture dual cure resin preparation: the prepolymer A is mixed with prepolymer B, be added catalyst, stirring be warming up to 80~90 DEG C after, reaction into mixed liquor NCO content be 8%~13%, be added polymerization inhibitor, discharging to get.The ultraviolet light that the preparation method is prepared/moisture dual cure resin solidification speed is fast, and solid content is high, NCO content is high, and paint film obtained has the excellent comprehensive performances such as chemicals-resistant, the excellent, high temperature resistant of adhesive force.
Description
Technical field
The present invention relates to high molecular materials, more particularly to a kind of ultraviolet light/moisture dual cure resin and its preparation side
Method and application.
Background technique
Woodwork coating occupies very important position in modern furniture coating, can play the decoration to substrate, protect
Protect or assign the multiple uses such as other specific functions.With the development of the social economy, national energy conservation and emission reduction implementation, and
The raising of people's ecological requirements and requirement, solvent wood coatings will be increasingly restricted.
Ultra-violet curing woodwork coating is increasingly taken seriously due to the environmental protection, energy conservation, efficient feature that have, development
It is very swift and violent.Uv curing coating is usually by the ingredients structure such as UV resin, reactive diluent or organic solvent, photoinitiator and auxiliary agent
At, there is the features such as solid containing height, energy consumption discharge is few, and rapid curing, paint film property is excellent, high production efficiency, but simultaneously because its
To solidify under ultraviolet light, some illumination less than shadow region and pigmented system and thick coating solidification conversion ratio it is low, it is right
The shape of solidification object also requires, and shaped piece solidification is restricted.The coating of other curing types is then difficult to meet market to painting
The requirement of the comprehensive performances such as chemicals-resistant, adhesive force, the high temperature resistant of material.
Summary of the invention
Based on this, it is necessary to a kind of environmental protection is provided, is not limited by article shape, and can make paint film chemicals-resistant obtained,
The ultraviolet light of the excellent combination properties such as adhesive force, high temperature resistant/moisture dual cure resin preparation method.
A kind of preparation method of ultraviolet light/moisture dual cure resin, includes the following steps:
(1) preparation of prepolymer A: be added catalyst and polymerization inhibitor catalysis acrylic ester compound carried out with 'beta '-ketoester it is advanced in years
Ke Er addition reaction obtains polymer A；
(2) preparation of prepolymer B: polyester diol is heated to 70~90 DEG C, catalyst and two isocyanide of aliphatic is added
Acid esters is stirred to react 2~3 hours；Wherein, the polyester diol and the molar ratio of the aliphatic diisocyanate are 1:30
~40；
(3) ultraviolet light/moisture dual cure resin preparation: by the prepolymer A and prepolymer B according to molar ratio 2~
Catalyst is added in 4:1 mixing, and after stirring is warming up to 80~90 DEG C, reaction NCO content into mixed liquor is 8%~13%, is added
Polymerization inhibitor discharges to get the ultraviolet light/moisture dual cure resin.
Ultraviolet light of the present invention/moisture dual cure resin preparation method, the process including three:
Process is first is that carry out addition reaction using acrylic ester compound and 'beta '-ketoester, in 'beta '-ketoester on active methylene group
It forms new covalent bond with acrylate carbon-carbon double bond end group carbon, forms a photocuring self-initiating resin, i.e. prepolymer A, in advance
Polymers A can pass through ultraviolet light-initiated Raolical polymerizable in the curing process.
Process with aliphatic diisocyanate second is that react the prepolymer that preparation end is NCO group using polyester diol
B, prepolymer B in the curing process, isocyanate group therein can in air moisture, in coating hydroxyl component
And the ingredients such as hydroxyl cellulose wood quality on timber are further crosslinked, and form fine and close reticular structure；Meanwhile in the mistake
The reasonable molar ratio of control-NCO/-OH in journey, carry out in it is cross-linking modified, the toughness of paint film after solidify can be effectively improved and resisted
Impact.
Prepolymer B is reacted with prepolymer A in process three, the NCO group part in prepolymer B is reacted with the first step
In 'beta '-ketoester in remaining reactive hydrogen form new covalent bond.Make the ultraviolet light being prepared/moisture dual cure tree as a result,
Rouge has the function of moisture solidification and self-initiating under the structure with acrylate, can film-forming under ultraviolet light, can also
6-8 hours film-formings are placed at normal temperature, and curing rate is fast, while solid content is high, NCO content is high.Using the ultraviolet light/tide
Paint film made from the coating of gas dual cure resin has the excellent comprehensive performances such as chemicals-resistant, the excellent, high temperature resistant of adhesive force,
There is good oil sealing effect particularly with heavy wool class timber.
The molar ratio of the acrylic ester compound and 'beta '-ketoester is 1~3:1 in one of the embodiments,.
The acrylic ester compound is multi-functional acrylate in one of the embodiments,.
In one of the embodiments, in step (1), the acrylic ester compound is two propylene of tripropylene glycol
Acid esters, 1,6- hexanediyl ester, trimethylolpropane trimethacrylate, ethoxyquin trimethylolpropane trimethacrylate
One of or it is a variety of.
Using multi-functional acrylate, the multi-functional acrylate of type especially as above can be mentioned effectively
The curing rate of high resin, and improve the hardness of paint film.
In one of the embodiments, in step (1), the 'beta '-ketoester be ethyl acetoacetate, acetoacetic acid allyl ester,
One of acetylacetone,2,4-pentanedione, methacrylic acid -2- ethyl acetoacetate are a variety of.It can be further using the 'beta '-ketoester of the type
Improve the self-initiating curing rate of resin.
In one of the embodiments, in step (1), the polymerization inhibitor is p-hydroxyanisole, 2,6- di-t-butyl -4-
One of methylphenol, hydroquinone are a variety of；The catalyst is isopropyl titanate, 11 carbon of 1,8- diazabicylo-
7- alkene (DBU), benzyltriethylammoinium chloride it is one or more.Dosage is Conventional catalytic amount.
In one of the embodiments, in step (2), the average molecular weight of the polyester diol is 1000~3000.
The average molecular weight of the polyester diol is rationally controlled, preferable flexibility can be obtained while guaranteeing hardness of paint film,
Avoid paint film cracking.
In one of the embodiments, in step (2), the aliphatic diisocyanate is hexa-methylene diisocyanate
One of ester, isophorone diisocyanate, hydrogenation methylenebis phenyl isocyanate are a variety of.Using the aliphatic of the type
Diisocyanate can advanced optimize the flexibility and intensity of paint film.
In one of the embodiments, in step (2), the catalyst is butyl tin dilaurate, isooctyl acid tin, 1,8-
One of 11 carbon -7- alkene (DBU) of diazabicylo is a variety of.Dosage is Conventional catalytic amount.
In one of the embodiments, in step (3), the polymerization inhibitor is p-hydroxyanisole, 2,6- di-t-butyl -4-
One of methylphenol, hydroquinone, triphenyl phosphite are a variety of；The catalyst is butyl tin dilaurate.It is described
The dosage of polymerization inhibitor and catalyst is conventional amount used.
In one of the embodiments, in step (3), after the discharging, carboxylic acid type monomer is added in gained feed liquid, i.e.,
Obtain the ultraviolet light/moisture dual cure resin.Thus the ultraviolet light/moisture dual cure resin stable storing can be improved
Property.
The carboxylic acid monomer is acrylic acid, acrylate modified phosphate, methacrylic acid in one of the embodiments,
One of ester modified phosphate, oxalic acid are a variety of；Dosage is the 0.1~0.2% of gained feed liquid.
The ultraviolet light being prepared the present invention also provides the ultraviolet light/moisture dual cure resin preparation method/
Moisture dual cure resin.
The present invention separately provides a kind of woodenware priming paint, including the following raw material component:
Wherein, the resin includes the ultraviolet light/moisture dual cure resin and hydroxy-containing resin, hydroxyl with
NCO base molar ratio is in 0.5~1:1.
Woodenware priming paint of the invention, by using the ultraviolet light/moisture dual cure resin, while reasonable disposition light
The auxiliary agents such as initiator, filler, a small amount of solvent, levelling agent, defoaming agent and wetting dispersing agent, manufactured woodenware priming paint stable storing
It is good, it has good workability, cured paint film excellent combination property.
The hydroxy-containing resin is hydroxy-ethyl acrylate, hydroxypropyl acrylate, pentaerythrite in one of the embodiments,
One of triacrylate, Hydroxylated acrylic resin, hydroxylated cellulose resin are a variety of.
The solvent is that ethyl acetate, butyl acetate, propylene glycol monomethyl ether are one or more in one of the embodiments,.
The filler is talcum powder in one of the embodiments,.
The conventional kind of this field can be used in the photoinitiator, levelling agent, defoaming agent, wetting dispersing agent.
Compared with prior art, the invention has the following advantages:
Ultraviolet light of the invention/moisture dual cure resin preparation method is made by the way that each step and raw material is rationally arranged
The ultraviolet light being prepared/moisture dual cure resin has moisture solidification and draws certainly under the structure with acrylate
Send out function, can film-forming under ultraviolet light, 6-8 hours film-formings can also be placed at normal temperature, curing rate is fast, and contains admittedly
Amount is high, NCO content is high.There is chemicals-resistant, attachment using paint film made from the ultraviolet light/moisture dual cure resin coating
The excellent comprehensive performances such as the excellent, high temperature resistant of power have good oil sealing effect particularly with heavy wool class timber.
Meanwhile solidifying and not limited by the shape of solidification object, colored paint and deep cure also can be realized higher conversion
Rate can also reduce the use of photoinitiator.
Woodenware priming paint of the present invention, it is the paint film chemicals-resistant of formation, adhesive force, resistance to by reasonable preparation each component
The excellent combination properties such as high temperature, water-fast, cracking resistance, and back cover effect is good, has good oil sealing particularly with heavy wool class timber
Effect, surface of the paint film effect is good, and no oilhole, levelling are good, gloss is high.
Specific embodiment
Ultraviolet light of the invention/moisture dual cure resin and preparation method thereof is made into one below in conjunction with specific embodiment
Step detailed description.
Embodiment 1
A kind of ultraviolet light of the present embodiment/moisture dual cure resin, it is as follows to prepare raw material:
Above-mentioned ultraviolet light/moisture dual cure resin the preparation method is as follows:
(1) ethoxyquin trimethylolpropane trimethacrylate, 2,6- bis- uncles the preparation of prepolymer A: are added in a kettle
Butyl -4- methylphenol is warming up to 60 DEG C, and DBU is added, and starts that ethyl acetoacetate is added dropwise, 80 DEG C are warming up to after being added dropwise,
Michael addition reaction is carried out, reaction obtains prepolymer A in 2 hours；
(2) preparation of prepolymer B: being warming up to 70 DEG C for polyester diol, then be added isophorone diisocyanate and
Catalyst dibutyltin cinnamic acid butyl tin, is warming up to 90 DEG C, is stirred to react 2 hours, obtains prepolymer B；Wherein, the polyester diol
Molar ratio with the aliphatic diisocyanate is 1:36；
(3) ultraviolet light/moisture dual cure resin preparation: by the prepolymer A and prepolymer B according to molar ratio 3:1
Catalyst dibutyltin cinnamic acid butyl tin is added in mixing, and 90 DEG C are reacted 2.5 hours, is down to 10% to NCO content and remains unchanged, adds
Enter p-hydroxyanisole, 2,6- di-tert-butyl-4-methy phenol, triphenyl phosphite, acrylic acid obtains after stirring 30 minutes
The ultraviolet light/moisture dual cure resin.
Embodiment 2
A kind of ultraviolet light of the present embodiment/moisture dual cure resin, it is as follows to prepare raw material:
Above-mentioned ultraviolet light/moisture dual cure resin preparation method similar embodiment 1.
Embodiment 3
A kind of ultraviolet light of the present embodiment/moisture dual cure resin, it is as follows to prepare raw material:
Above-mentioned ultraviolet light/moisture dual cure resin preparation method similar embodiment 1.
Embodiment 4
A kind of ultraviolet light of the present embodiment/moisture dual cure resin, it is as follows to prepare raw material:
Above-mentioned ultraviolet light/moisture dual cure resin preparation method similar embodiment 1.
Comparative example 1
A kind of ultraviolet light of this comparative example/moisture dual cure resin, raw material and preparation method are similar to Example 1, area
It is not: in step (1), the 'beta '-ketoester is replaced with benzophenone.
Comparative example 2
A kind of ultraviolet light of this comparative example/moisture dual cure resin, raw material and preparation method are similar to Example 1, area
It is not: in step (2), replaces polyester diol (molecular weight 1000) with polyether Glycols.
Embodiment 5
By ultraviolet light/moisture dual cure resin that embodiment 1-4 and comparative example 1-2 are prepared respectively according to matching as follows
Woodenware priming paint is made in side.
| Raw material | Dosage/kg |
| Ethyl acetate | 20 |
| Photoinitiator 184 | 7.5 |
| Photoinitiator tpo | 2.5 |
| Terminal hydroxy group acrylic resin | 30 |
| Ultraviolet light/moisture dual cure resin | 30 |
| Levelling agent TEGO2100 | 3 |
| Defoaming agent TEGO920 | 1.5 |
| Wetting dispersing agent | 3 |
| Filler talcum powder | 20 |
Above-mentioned woodenware priming paint the preparation method comprises the following steps: accurate weigh each component raw material according to formula, with revolving speed in dispersion machine
800r/min stir 1 hour to get.
Woodenware priming paint appearance made of the ultraviolet light described in embodiment 1-5/moisture dual cure resin is white or micro-
Yellow transparency liquid carries out performance detection respectively, as a result as follows:
Each technical characteristic of embodiment described above can be combined arbitrarily, for simplicity of description, not to above-mentioned reality
It applies all possible combination of each technical characteristic in example to be all described, as long as however, the combination of these technical characteristics is not deposited
In contradiction, all should be considered as described in this specification.
The embodiments described above only express several embodiments of the present invention, and the description thereof is more specific and detailed, but simultaneously
It cannot therefore be construed as limiting the scope of the patent.It should be pointed out that coming for those of ordinary skill in the art
It says, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to protection of the invention
Range.Therefore, the scope of protection of the patent of the invention shall be subject to the appended claims.
Claims (10)
1. a kind of ultraviolet light/moisture dual cure resin preparation method, which comprises the steps of:
(1) preparation of prepolymer A: being added catalyst and polymerization inhibitor catalysis acrylic ester compound and 'beta '-ketoester carries out Michael
Addition reaction obtains polymer A；The 'beta '-ketoester is ethyl acetoacetate, acetoacetic acid allyl ester, methacrylic acid -2- acetyl
One of ethyl acetate is a variety of；
(2) preparation of prepolymer B: being heated to 70~90 DEG C for polyester diol, catalyst and aliphatic diisocyanate be added,
It is stirred to react 2~3 hours；Wherein, the polyester diol and the molar ratio of the aliphatic diisocyanate are 1:30~40；
(3) ultraviolet light/moisture dual cure resin preparation: the prepolymer A and prepolymer B is mixed according to 2~4:1 of molar ratio
It closes, catalyst is added, after stirring is warming up to 80~90 DEG C, reaction NCO content into mixed liquor is 8%~13%, and polymerization inhibitor is added
Agent discharges to get the ultraviolet light/moisture dual cure resin.
2. ultraviolet light according to claim 1/moisture dual cure resin preparation method, which is characterized in that step (1)
In, the acrylic ester compound is tri (propylene glycol) diacrylate, 1,6- hexanediyl ester, trihydroxy methyl
One of propane triacrylate, ethoxyquin trimethylolpropane trimethacrylate are a variety of.
3. ultraviolet light according to claim 1/moisture dual cure resin preparation method, which is characterized in that step (1)
In, the molar ratio of the acrylic ester compound and 'beta '-ketoester is 1~3:1.
4. ultraviolet light according to claim 1/moisture dual cure resin preparation method, which is characterized in that step (1)
In, the polymerization inhibitor is one of p-hydroxyanisole, 2,6- di-tert-butyl-4-methy phenol, hydroquinone or a variety of；Institute
State catalyst be isopropyl titanate, 11 carbon -7- alkene of 1,8- diazabicylo, benzyltriethylammoinium chloride it is one or more.
5. ultraviolet light according to claim 1/moisture dual cure resin preparation method, which is characterized in that step (2)
In, the average molecular weight of the polyester diol is 1000~3000.
6. ultraviolet light according to claim 1/moisture dual cure resin preparation method, which is characterized in that step (2)
In, the aliphatic diisocyanate is hexamethylene diisocyanate, isophorone diisocyanate, hydrogenation phenylmethane two
One of isocyanates is a variety of.
7. ultraviolet light according to claim 1/moisture dual cure resin preparation method, which is characterized in that step (2)
In, the catalyst be one of dibutyl tin dilaurate, isooctyl acid tin, 1,8- diazabicylo, 11 carbon -7- alkene or
It is a variety of.
8. ultraviolet light according to claim 1-7/moisture dual cure resin preparation method, feature exist
In in step (3), the polymerization inhibitor is p-hydroxyanisole, 2,6- di-tert-butyl-4-methy phenol, hydroquinone, phosphorous acid
One of triphenylmethyl methacrylate is a variety of；The catalyst is dibutyl tin dilaurate.
9. the described in any item ultraviolet lights of claim 1-8/moisture dual cure resin preparation method is prepared ultraviolet
Light/moisture dual cure resin.
10. a kind of woodenware priming paint, which is characterized in that by weight percentage, including the following raw material component:
Wherein, the resin includes the described in any item ultraviolet lights of claim 1-8/moisture dual cure resin and hydroxyl
Resin, hydroxyl and NCO base molar ratio are in 0.5~1:1.
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| CN201710187834.1A CN107446483B (en) | 2017-03-27 | 2017-03-27 | Ultraviolet light/moisture dual cure resin and its preparation method and application |
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| CN114031743B (en) * | 2021-12-10 | 2023-07-21 | 河源然生新材料有限公司 | Self-initiated small molecule chain extender, self-initiated polyurethane acrylate prepolymer and preparation method thereof |
| CN114085353B (en) * | 2021-12-31 | 2023-08-11 | 武汉中科先进材料科技有限公司 | Photo-thermal dual-curing resin and preparation method thereof |
| CN114605595B (en) * | 2022-03-28 | 2023-06-09 | 天津科技大学 | Preparation method and application of lignin-based polyurethane photosensitive resin composition for photocuring 3D printing |
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| CN101006103A (en) * | 2004-04-29 | 2007-07-25 | 亚什兰许可和知识产权有限公司 | Radiation-curable coatings for wood substrates from multifunctional acrylate oligomers |
| CN104558501A (en) * | 2014-12-15 | 2015-04-29 | 北京海斯迪克新材料有限公司 | Ultraviolet ray and moisture dual-cured modified polyurethane and preparation method thereof |
| EP2960298A1 (en) * | 2014-06-26 | 2015-12-30 | Dymax Corporation | Actinic radiation and moisture dual curable composition |
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| CN101006103A (en) * | 2004-04-29 | 2007-07-25 | 亚什兰许可和知识产权有限公司 | Radiation-curable coatings for wood substrates from multifunctional acrylate oligomers |
| EP2960298A1 (en) * | 2014-06-26 | 2015-12-30 | Dymax Corporation | Actinic radiation and moisture dual curable composition |
| CN104558501A (en) * | 2014-12-15 | 2015-04-29 | 北京海斯迪克新材料有限公司 | Ultraviolet ray and moisture dual-cured modified polyurethane and preparation method thereof |
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