CN107446483A - 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
- Publication number
- CN107446483A CN107446483A CN201710187834.1A CN201710187834A CN107446483A CN 107446483 A CN107446483 A CN 107446483A CN 201710187834 A CN201710187834 A CN 201710187834A CN 107446483 A CN107446483 A CN 107446483A
- Authority
- CN
- China
- Prior art keywords
- preparation
- ultraviolet light
- dual cure
- cure resin
- moisture dual
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Classifications
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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
Abstract
The present invention relates to a kind of ultraviolet light/moisture dual cure resin and its preparation method and application, the preparation method comprises the following steps：(1) prepolymer A preparation：Add catalyst and polymerization inhibitor catalysis acrylic ester compound carries out Michael addition reaction with β ketone esters；(2) prepolymer B preparation：Polyester diol is heated to 70~90 DEG C, adds catalyst and aliphatic diisocyanate, stirring reaction 2~3 hours；(3) preparation of ultraviolet light/moisture dual cure resin：The prepolymer A is mixed with prepolymer B, adds catalyst, after stirring is warming up to 80~90 DEG C, it is 8%~13% to react into mixed liquor NCO content, adds polymerization inhibitor, discharging, produces.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 obtained paint film has the excellent combination properties such as the excellent, high temperature resistant of chemicals-resistant, adhesive force.
Description
Technical field
The present invention relates to high polymer material, more particularly to a kind of ultraviolet light/moisture dual cure resin and its preparation side
Method and application.
Background technology
Woodwork coating occupies very important position in modern furniture application, and it can play the decoration to base material, protect
Protect or assign the multiple uses such as other specific functions.With the development of the social economy, national energy-saving emission reduction implementation, and
People's ecological requirements and desired raising, solvent wood coatings will be increasingly restricted.
Ultra-violet curing woodwork coating due to environmental protection, energy-conservation, it is efficient the characteristics of, be increasingly taken seriously, develop
It is very swift and violent.Uv curing coating is generally by the composition structure such as UV resins, reactive diluent or organic solvent, light trigger and auxiliary agent
Into, there is the features such as solid containing height, power consumption discharge is few, and rapid curing, paint film property is excellent, and production efficiency is high, 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 is also required, and shaped piece solidification is restricted.The coating of other curing types is then difficult to meet market to applying
The requirement of the combination properties such as the chemicals-resistant of material, adhesive force, high temperature resistant.
The content of the invention
Based on this, it is necessary to a kind of environmental protection is provided, not limited by article shape, and can make obtained paint film chemicals-resistant,
The preparation method of the ultraviolet light of the excellent combination properties such as adhesive force, high temperature resistant/moisture dual cure resin.
A kind of preparation method of ultraviolet light/moisture dual cure resin, comprises the following steps：
(1) prepolymer A preparation：Add catalyst and polymerization inhibitor catalysis acrylic ester compound is stepped with 'beta '-ketoester
Ke Er addition reactions, obtain polymer A；
(2) prepolymer B preparation：Polyester diol is heated to 70~90 DEG C, adds catalyst and the isocyanide of aliphatic two
Acid esters, stirring reaction 2~3 hours；Wherein, the polyester diol and the mol ratio of the aliphatic diisocyanate are 1:30
~40；
(3) preparation of ultraviolet light/moisture dual cure resin：By the prepolymer A and prepolymer B according to mol ratio 2~
4:1 mixing, catalyst is added, after stirring is warming up to 80~90 DEG C, it is 8%~13% that NCO content, which is reacted into mixed liquor, is added
Polymerization inhibitor, discharging, produces the ultraviolet light/moisture dual cure resin.
The preparation method of ultraviolet light of the present invention/moisture dual cure resin, include the process of three：
Process one is to use acrylic ester compound and 'beta '-ketoester progress addition reaction, in 'beta '-ketoester on active methylene group
Form new covalent bond with acrylate carbon-carbon double bond end group carbon, form 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 two is to prepare the prepolymer that end is NCO group using polyester diol and aliphatic diisocyanate reaction
In the curing process, NCO therein can be with the component of hydroxyl in the moisture in air, coating by B, prepolymer B
And the composition such as hydroxyl cellulose wood quality on timber is further crosslinked, the network structure of densification is formed；Meanwhile in the mistake
Reasonable control-NCO/-OH mol ratio in journey, it is cross-linking modified in progress, the toughness of paint film and anti-can be effectively improved after solidification
Impact.
Prepolymer B and prepolymer A are reacted 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.Thus, the ultraviolet light/moisture dual cure tree being prepared is made
Fat has moisture solidification and self-initiating function again under the structure with acrylate, can film-forming under ultraviolet light, also may be used
6-8 hour film-formings are placed at normal temperatures, 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 combination properties such as the excellent, high temperature resistant of chemicals-resistant, adhesive force,
There is good oil sealing effect particularly with more oils timber.
In one of the embodiments, the mol 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 step (1), the acrylic ester compound is the propylene of tripropylene glycol two
Acid esters, 1,6- hexanediyl esters, trimethylolpropane trimethacrylate, ethoxyquin trimethylolpropane trimethacrylate
In one or more.
Using multi-functional acrylate, the especially as above multi-functional acrylate of species can be carried 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 or more in acetylacetone,2,4-pentanedione, methacrylic acid -2- ethyl acetoacetates.Can be further using the 'beta '-ketoester of the species
Improve the self-initiating curing rate of resin.
In one of the embodiments, in step (1), the polymerization inhibitor is MEHQ, 2,6- di-t-butyls -4-
One or more in methylphenol, hydroquinones；The catalyst be isopropyl titanate, the carbon of 1,8- diazabicylos 11-
7- alkene (DBU), the one or more of benzyltriethylammoinium chloride.Dosage is Conventional catalytic amount.
In one of the embodiments, in step (2), the mean molecule quantity of the polyester diol is 1000~3000.
The mean molecule quantity of the polyester diol is rationally controlled, preferable pliability can be obtained while hardness of paint film is ensured,
Avoid paint film cracking.
In one of the embodiments, in step (2), the aliphatic diisocyanate is the isocyanic acid of hexa-methylene two
One or more in ester, IPDI, hydrogenation methylenebis phenyl isocyanate.Using the aliphatic of the species
Diisocyanate can further optimize the pliability 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 or more in the carbon -7- alkene (DBU) of diazabicylo 11.Dosage is Conventional catalytic amount.
In one of the embodiments, in step (3), the polymerization inhibitor is MEHQ, 2,6- di-t-butyls -4-
One or more in methylphenol, hydroquinones, triphenyl phosphite；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 stable storing of the ultraviolet light/moisture dual cure resin can be improved
Property.
In one of the embodiments, the carboxylic acid monomer is acrylic acid, acrylate modified phosphate, methacrylic acid
One or more in ester modified phosphate, oxalic acid；Dosage is the 0.1~0.2% of gained feed liquid.
The ultraviolet light that the preparation method of the invention for also providing described ultraviolet light/moisture dual cure resin is prepared/
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 described ultraviolet light/moisture dual cure resin and hydroxy-containing resin, hydroxyl with
NCO base mol ratios are 0.5~1：1.
The woodenware priming paint of the present invention, by using described ultraviolet light/moisture dual cure resin, while reasonable disposition light
The auxiliary agents such as initiator, filler, a small amount of solvent, levelling agent, defoamer and wetting dispersing agent, manufactured woodenware priming paint stable storing
It is good, have good workability, cured paint film excellent combination property.
In one of the embodiments, the hydroxy-containing resin is hydroxy-ethyl acrylate, hydroxypropyl acrylate, pentaerythrite
One or more in triacrylate, Hydroxylated acrylic resin, hydroxylated cellulose resin.
In one of the embodiments, the solvent is ethyl acetate, butyl acetate, propylene glycol monomethyl ether one or more.
In one of the embodiments, the filler is talcum powder.
The light trigger, levelling agent, defoamer, wetting dispersing agent can use the conventional kind of this area.
Compared with prior art, the invention has the advantages that：
The preparation method of ultraviolet light/moisture dual cure resin of the present invention is made by rationally setting each step and raw material
The ultraviolet light being prepared/moisture dual cure resin has moisture solidification and drawn certainly again under the structure with acrylate
Send out function, can film-forming under ultraviolet light, can also place 6-8 hour film-formings at normal temperatures, 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 coating of the ultraviolet light/moisture dual cure resin
The excellent combination properties such as power is excellent, high temperature resistant, there is good oil sealing effect particularly with more oils timber.
Meanwhile solidification is not limited by the shape of solidification object, colored paint and deep cure can also realize higher conversion
Rate, the use of light trigger can also be reduced.
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 property such as high temperature, water-fast, cracking resistance, and back cover effect is good, has good oil sealing particularly with more oils timber
Effect, coating surface effect is good, and no oilhole, levelling are good, gloss is high.
Embodiment
Ultraviolet light/moisture dual cure resin of the present invention 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, its preparing raw material are as follows：
The preparation method of above-mentioned ultraviolet light/moisture dual cure resin is as follows：
(1) prepolymer A preparation：Ethoxyquin trimethylolpropane trimethacrylate, 2,6- bis- uncles are added in a kettle
Butyl -4- methylphenols, 60 DEG C are warming up to, add DBU, started 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) prepolymer B preparation：Polyester diol is warming up to 70 DEG C, then add IPDI and
Catalyst dibutyltin cinnamic acid butyl tin, 90 DEG C are warming up to, stirring reaction 2 hours, obtains prepolymer B；Wherein, the polyester diol
Mol ratio with the aliphatic diisocyanate is 1：36；
(3) preparation of ultraviolet light/moisture dual cure resin：By the prepolymer A and prepolymer B according to mol ratio 3:1
Mixing, catalyst dibutyltin cinnamic acid butyl tin is added, 90 DEG C are reacted 2.5 hours, are treated that NCO content is down to 10% and keeps constant, are added
Enter MEHQ, 2,6- di-tert-butyl-4-methy phenols, triphenyl phosphite, acrylic acid, after stirring 30 minutes, obtain
The ultraviolet light/moisture dual cure resin.
Embodiment 2
A kind of ultraviolet light of the present embodiment/moisture dual cure resin, its preparing raw material are as follows：
The preparation method similar embodiment 1 of above-mentioned ultraviolet light/moisture dual cure resin.
Embodiment 3
A kind of ultraviolet light of the present embodiment/moisture dual cure resin, its preparing raw material are as follows：
The preparation method similar embodiment 1 of above-mentioned ultraviolet light/moisture dual cure resin.
Embodiment 4
A kind of ultraviolet light of the present embodiment/moisture dual cure resin, its preparing raw material are as follows：
The preparation method similar embodiment 1 of above-mentioned ultraviolet light/moisture dual cure resin.
Comparative example 1
A kind of ultraviolet light of this comparative example/moisture dual cure resin, its 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, its raw material and preparation method are similar to Example 1, area
It is not：In step (2), polyester diol is replaced using polyether Glycols (molecular weight is 1000).
Embodiment 5
The ultraviolet light that embodiment 1-4 and comparative example 1-2 are prepared/moisture dual cure resin respectively according to matching somebody with somebody as follows
Woodenware priming paint is made in side.
| Raw material | Dosage/kg |
| Ethyl acetate | 20 |
| Light trigger 184 | 7.5 |
| Light trigger tpo | 2.5 |
| Terminal hydroxy group acrylic resin | 30 |
| Ultraviolet light/moisture dual cure resin | 30 |
| Levelling agent TEGO2100 | 3 |
| Defoamer TEGO920 | 1.5 |
| Wetting dispersing agent | 3 |
| Filler talcum powder | 20 |
The preparation method of above-mentioned woodenware priming paint is：Each component raw material accurately is weighed according to formula, with rotating speed in dispersion machine
800r/min is stirred 1 hour, is produced.
Woodenware priming paint outward appearance is white or micro- made of the ultraviolet light described in embodiment 1-5/moisture dual cure resin
Yellow transparency liquid, performance detection is carried out respectively, it is as a result as follows：
Each technical characteristic of embodiment described above can be combined arbitrarily, to make description succinct, not to above-mentioned reality
Apply 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, the scope that this specification is recorded all is considered to be.
Embodiment described above only expresses the several embodiments of the present invention, and its description is more specific and detailed, but simultaneously
Can not therefore it be construed as limiting the scope of the patent.It should be pointed out that come for one of ordinary skill in the art
Say, without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to the protection of the present invention
Scope.Therefore, the protection domain of patent of the present invention should be determined by the appended claims.
Claims (10)
1. the preparation method of a kind of ultraviolet light/moisture dual cure resin, it is characterised in that comprise the following steps：
(1) prepolymer A preparation：Add catalyst and polymerization inhibitor catalysis acrylic ester compound carries out Michael with 'beta '-ketoester
Addition reaction, obtain polymer A；
(2) prepolymer B preparation：Polyester diol is heated to 70~90 DEG C, adds catalyst and aliphatic diisocyanate,
Stirring reaction 2~3 hours；Wherein, the polyester diol and the mol ratio of the aliphatic diisocyanate are 1:30~40；
(3) preparation of ultraviolet light/moisture dual cure resin：By the prepolymer A and prepolymer B according to mol ratio 2~4:1 is mixed
Close, add catalyst, after stirring is warming up to 80~90 DEG C, it is 8%~13% to react into mixed liquor NCO content, adds inhibition
Agent, discharging, produces the ultraviolet light/moisture dual cure resin.
2. the preparation method of ultraviolet light according to claim 1/moisture dual cure resin, it is characterised in that step (1)
In, the acrylic ester compound is tri (propylene glycol) diacrylate, 1,6- hexanediyl esters, trihydroxy methyl
One or more in propane triacrylate, ethoxyquin trimethylolpropane trimethacrylate.
3. the preparation method of ultraviolet light according to claim 1/moisture dual cure resin, it is characterised in that step (1)
In, the 'beta '-ketoester is ethyl acetoacetate, acetoacetic acid allyl ester, acetylacetone,2,4-pentanedione, methacrylic acid -2- ethyl acetoacetates
In one or more.
4. the preparation method of ultraviolet light according to claim 1/moisture dual cure resin, it is characterised in that step (1)
In, the polymerization inhibitor is the one or more in MEHQ, 2,6- di-tert-butyl-4-methy phenols, hydroquinones；Institute
Catalyst is stated as isopropyl titanate, the carbon -7- alkene of 1,8- diazabicylos 11, the one or more of benzyltriethylammoinium chloride.
5. the preparation method of ultraviolet light according to claim 1/moisture dual cure resin, it is characterised in that step (2)
In, the mean molecule quantity of the polyester diol is 1000~3000.
6. the preparation method of ultraviolet light according to claim 1/moisture dual cure resin, it is characterised in that step (2)
In, the aliphatic diisocyanate is hexamethylene diisocyanate, IPDI, hydrogenation phenylmethane two
One or more in isocyanates.
7. the preparation method of ultraviolet light according to claim 1/moisture dual cure resin, it is characterised in that step (2)
In, the catalyst is one kind or more in butyl tin dilaurate, isooctyl acid tin, the carbon -7- alkene of 1,8- diazabicylos 11
Kind.
8. the preparation method of ultraviolet light/moisture dual cure resin according to claim any one of 1-7, its feature exist
In in step (3), the polymerization inhibitor is MEHQ, 2,6- di-tert-butyl-4-methy phenols, hydroquinones, phosphorous acid
One or more in triphenylmethyl methacrylate；The catalyst is butyl tin dilaurate.
9. the preparation method of ultraviolet light/moisture dual cure resin described in claim any one of 1-8 is prepared ultraviolet
Light/moisture dual cure resin.
10. a kind of woodenware priming paint, it is characterised in that including the following raw material component：
Wherein, the resin includes the ultraviolet light/moisture dual cure resin and hydroxyl described in claim any one of 1-8
Resin, hydroxyl is with NCO base mol ratios 0.5~1：1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710187834.1A CN107446483B (en) | 2017-03-27 | 2017-03-27 | Ultraviolet light/moisture dual cure resin and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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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| Publication Number | Publication Date |
|---|---|
| CN107446483A true CN107446483A (en) | 2017-12-08 |
| CN107446483B CN107446483B (en) | 2019-11-12 |
Family
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| CN201710187834.1A Active CN107446483B (en) | 2017-03-27 | 2017-03-27 | Ultraviolet light/moisture dual cure resin and its preparation method and application |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114031743A (en) * | 2021-12-10 | 2022-02-11 | 河源然生新材料有限公司 | Self-initiated micromolecule chain extender, self-initiated polyurethane acrylate prepolymer and preparation method |
| CN114085353A (en) * | 2021-12-31 | 2022-02-25 | 武汉中科先进技术研究院有限公司 | Light-heat dual-curing resin and preparation method thereof |
| CN114605595A (en) * | 2022-03-28 | 2022-06-10 | 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 |
| EP2960298A1 (en) * | 2014-06-26 | 2015-12-30 | Dymax Corporation | Actinic radiation and moisture dual curable composition |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114031743A (en) * | 2021-12-10 | 2022-02-11 | 河源然生新材料有限公司 | Self-initiated micromolecule chain extender, self-initiated polyurethane acrylate prepolymer and preparation method |
| CN114085353A (en) * | 2021-12-31 | 2022-02-25 | 武汉中科先进技术研究院有限公司 | Light-heat dual-curing resin 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 |
| CN114605595A (en) * | 2022-03-28 | 2022-06-10 | 天津科技大学 | Preparation method and application of lignin-based polyurethane photosensitive resin composition for photocuring 3D printing |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107446483B (en) | 2019-11-12 |
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