CN106866929A - A kind of polyfunctionality castor oil-base light-cured resin and its preparation method and application - Google Patents
A kind of polyfunctionality castor oil-base light-cured resin and its preparation method and application Download PDFInfo
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- CN106866929A CN106866929A CN201710101874.XA CN201710101874A CN106866929A CN 106866929 A CN106866929 A CN 106866929A CN 201710101874 A CN201710101874 A CN 201710101874A CN 106866929 A CN106866929 A CN 106866929A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y70/00—Materials specially adapted for additive manufacturing
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
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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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/06—Biodegradable
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- 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
A kind of polyfunctionality castor oil-base light-cured resin and its preparation method and application, reaction raw materials are isocyanates, hydroxy acrylate, add polymerization inhibitor and catalyst, logical nitrogen protection reaction certain hour to obtain the blocked prepolymer of inter-mediate isocyanate half；By the blocked prepolymer of isocyanates half obtained in castor oil addition step, polyurethane based on castor oil acrylate is obtained；Resin is mixed with light trigger, diluent, under ultraviolet radiation, the UV castor oil-base resins of function admirable is obtained.The light-cured resin of present invention synthesis has molecular weight and viscosity higher, enhances the interaction between molecular resin, improves the photo-crosslinking efficiency of resin；The product contains more terminal double bond, and fast-photocurable suitably does coating, 3D printing material of UV-curable etc.；, with cured film water absorption rate and cubical contraction is greatly improved, while with low cost, process is simple is controllable, and product is more green for obtained light-cured resin.
Description
Technical field
The invention belongs to photo-curing material field, it is related to a kind of preparation method of hydrophobic light-cured resin, it is especially a kind of
Polyfunctionality plant oil base light-cured resin and its preparation method and application.
Background technology
Ultraviolet (uv) curing technology is the new technique of an energy-conservation and environmental protection, because its curing rate is fast, environment-friendly,
The characteristics such as energy-output ratio is few, solvent-free volatilization, make the application of photocuring product increasingly extensive.At present, most light-cured resins
All rely on the related chemical reagent of petroleum resources.At present, and fossil resources are limited and environmental issue, vegetable oil is used as can be again
Production-goods source is cheap, aboundresources and biodegradable, therefore, researcher consolidates more sight steering plant oil base light
Change material direction.
Natural oil is a major class natural organic-compound, is defined as mixed fatty acid triglycercide.Research is main to concentrate
Chemical modification synthesis is carried out in consaturated oil, some special functional groups are introduced（Such as rigid radical, ignition-proof element）Adapt to material
The need for material technique, aspect of performance.Castor oil is a kind of unedible oil, wide material sources, cheap, environment-friendly renewable
Resource.Contain native hydroxyl in its molecule, with typical unrighted acid triglyceride structure.Castor oil is a kind of stickiness
The nondrying oil of faint yellow non-volatility, containing double bond, 3 kinds of active function groups of hydroxyl and ester group, thus is prone to hydrolysis, soap
The series of chemical such as change, amidatioon, oxidation, so that the chemical modification castor oil that availability can be various.Castor oil it is main by
Castor oil acid constitute, wherein castor oil acid (chemical entitled ricinoleic acid) content more than 89%, in natural plants
Oily middle hydroxyl value highest.Remaining aliphatic acid includes linoleic acid (4.2%), oleic acid (3.0%), stearic acid (1%), palmitic acid
(1%) etc..Castor oil can also occur alcoholysis with low-carbon polyol, obtain the castor oil polyhydric alcohol containing different hydroxyl-functional numbers and enter
Row alcoholysis and ester exchange, obtain the castor oil derivative of different hydroxyl values, degree of functionality.These castor oil derivatives can exist as raw material
Coating, ink and polyurethane industrial are widely available application.
In recent years, having in succession can UV polyurethane based on castor oil acrylate（COPUA）Preparation, Liu Yaode using dehydration castor
Sesame oil produces dry alkyd resin, and the alkyd resin for obtaining has preferable rate of drying, alkali resistance and pliability etc. physical
Energy.Yeganeh new polyurethane coatings with castor oil as Material synthesis, find subtracting with polyol hydroxyl value
Few, crosslinked polymer density is also reduced therewith.Trevino prepares castor-oil plant with castor oil and t-butylacetoacetate ester as raw material
Oily beta-ketoester, then carry out anabolic reaction with multiple functionalized amine crosslinker and obtain the good film of brightness and flexibility.Apply
Literary virtue etc. prepares super branched polyurethane with diisocyanate and diethanol amine reaction, then with homemade diisocyanate-propylene
Sour hydroxyl ethyl ester monomer is extremely modified to hyperbranched poly ammonia, prepares ultra-branched polyurethane acrylate.
The content of the invention
The technical problem of solution：:The purpose of the present invention is intended to develop UV resin new varieties, overcomes current UV resins to depend on
The low shortcoming of petrochemical materials, hydrophobicity, there is provided a kind of polyfunctionality castor oil-base light-cured resin and preparation method thereof and
Using, so that the photo-crosslinking efficiency of light-cured resin is improved, with product quality stabilization, lower-cost advantage.
Technical scheme：A kind of preparation method of polyfunctionality castor oil-base light-cured resin, comprises the following steps:（1）With
Isocyanates and hydroxy acrylate are raw material, add the catalyst and polymerization inhibitor of effective dose, lead to nitrogen protection, at 20-120 DEG C
Under the conditions of, until NCO content reaches desired value 14% ~ 7%, obtain isocyanates and partly block intermediate, wherein isocyanates and hydroxyl
The molar ratio of material of base acrylate is 0.5-1.44:1, the reaction time is 2-10 hours；The polymerization inhibitor is selected to methoxyl group
Any one in phenol, MEHQ, hydroquinones, polymerization inhibitor consumption is the 0.5-4% of reaction mass gross weight；It is described
Selected from any one in dibutyltin dilaurate, stannous octoate, dimethylethanolamine, catalyst amount is reaction to catalyst
The 1-5% of material gross weight；（2）By step（1）The isocyanates for obtaining half blocks intermediate and is reacted with castor oil, and mol ratio is
0.6-0.8:1, temperature is 30-140 DEG C, and the reaction time is 3-12 hours, until NCO content is less than 0.5%, obtains polyurethane third
Olefin(e) acid ester prepolymer；（3）By polyurethane acrylate prepolymer, account for the light trigger of reactant gross mass 1%-5% and account for reaction
Diluent of the thing gross mass no more than 40% mixes, and is sufficiently stirred for rear ultrasonic disperse, cast or film, and UV illumination obtains multifunctional
Degree castor oil-base light-cured resin.
Isocyanates described in step (1) is the compound containing two isocyanate groups (- NCO) or its mixing
Thing, the compound is IPDI（IPDI）, toluene di-isocyanate(TDI)（TDI）, the isocyanide of diphenyl methane two
Acid esters（MDI）, PPDI（PPDI）, cyclohexanedimethyleterephthalate diisocyanate（HXDI）, the isocyanide of norbornane two
Acid esters（NBDI）In any one.
Step（1）Described hydroxy acrylate be pentaerythritol triacrylate, Dipentaerythritol Pentaacrylate or
Trimethylolpropane diacrylate.
Step（1）Described raw material is to react in a solvent, the solvent be selected from n-hexane, butanone or hexamethylene, and
Step（2）Solvent is removed finally by rotary evaporation.
Step（2）It is 0.6 that the isocyanates half blocks intermediate with the molar ratio of material of castor oil:1.
Step（3）The diluent is hydroxy-ethyl acrylate, hydroxyethyl methacrylate, hydroxy-ethyl acrylate, Ji Wusi
At least one in alcohol triacrylate, triethylene-glycol diacrylate, three acrylic acid propane front three alcohol esters.
Step（3）The light trigger is 2- hydroxy-2-methyl propiophenones, and consumption accounts for the 2% of reactant gross mass.
Step（3）The mass ratio of the polyurethane acrylate prepolymer, light trigger and diluent is 0.78:
0.02:0.2。
The polyfunctionality castor oil-base light-cured resin that the above method is prepared.
Application of the above-mentioned polyfunctionality castor oil-base light-cured resin in coating, ink or 3D printing material is prepared.
Beneficial effect：Polyfunctional group castor oil-base light-cured resin synthesized by the present invention belongs to new varieties, can quickly hand over
Connection solidification.The COPUA resins of synthesis introduce rigid structure and acrylate group, and curing efficiency is increased substantially, after solidification
With good hydrophobicity and heat endurance, combination property is improved.Synthesis process is simple, be easily controlled, it is not necessary to make
With special equipment, and raw material it is renewable and can Partial digestion, meet the requirement of energy-conserving and environment-protective, it is preceding with wide application
Scape.
Brief description of the drawings
Fig. 1 is the FT-IR spectrograms of COPUA；
Fig. 2 is COPUA's1H-NMR is composed；
Fig. 3 is the contact angle figure of COPUA.
Specific embodiment
It is described further with specific embodiment below.
Embodiment 1
（1）Under conditions of solvent hexane presence, with isocyanates and pentaerythritol triacrylate as raw material（Isocyanates
It is 0.8 with the molar ratio of material of acrylate:1）, add catalyst dibutyltin dilaurate（The 2% of reactant gross mass）
With polymerization inhibitor MEHQ（The 1% of reactant gross mass）, lead to nitrogen protection and reacted 4 hours under the conditions of 30 DEG C, until
NCO content reaches 7%, obtains isocyanates and partly blocks intermediate；
（2）By step（1）The isocyanates for obtaining half blocks intermediate and is reacted with castor oil（Molar ratio of material is 0.9:1）, temperature
Degree in 10 hours reaction time, until NCO content is less than 0.5%, obtains polyurethane acrylate prepolymer, by rotation at 40 DEG C
Evaporation of solvent.
（3）By polyurethane acrylate prepolymer and light trigger 2- hydroxy-2-methyls propiophenone, diluent acrylic acid hydroxyl
Ethyl ester presses mass fraction 78%：2%：20% ratio mixing, is sufficiently stirred for rear ultrasonic disperse 30 minutes, pours into a mould or film, UV illumination
Obtain COPUA solidification battens.Fig. 1 is the FT-IR spectrograms of COPUA；Fig. 2 is COPUA's1H-NMR is composed；Fig. 3-a connect for COPUA's
Feeler is 105.16 °；
Embodiment 2
（1）Under conditions of solvent-free presence, with isocyanates and pentaerythritol triacrylate as raw material（Isocyanates and third
The molar ratio of material of olefin(e) acid ester is 0.9:1）, add catalyst dibutyltin dilaurate（The 2% of reactant gross mass）And resistance
Poly- agent p methoxy phenol（The 1.5% of reactant gross mass）, lead to nitrogen protection and reacted 5 hours under the conditions of 20 DEG C, until NCO
Content reaches 6.5%, obtains isocyanates and partly blocks intermediate；
（2）By step（1）The isocyanates for obtaining half blocks intermediate and is reacted with castor oil（Molar ratio of material is 0.9:1）, temperature
Degree in 8 hours reaction time, until NCO content is less than 0.5%, obtains polyurethane acrylate prepolymer at 50 DEG C；
（3）By polyurethane acrylate prepolymer and light trigger 2- hydroxy-2-methyls propiophenone, diluent hydroxyethyl methacrylate
Ethyl ester presses mass fraction 83%：2%：15% ratio mixing, is sufficiently stirred for rear ultrasonic disperse 30 minutes, pours into a mould film forming, and UV illumination is obtained
To COPUA solidify batten, later stage heat cure condition be 120 DEG C 2 hours.Fig. 3-b are 95.74 ° for the contact angle of COPUA.
Embodiment 3
（1）Under conditions of positive butanone is solvent, with isocyanates and pentaerythritol triacrylate as raw material（Isocyanates and
The molar ratio of material of acrylate is 0.7:1）, add catalyst dibutyltin dilaurate（The 3% of reactant gross mass）With
Hydroquinone of polymerization retarder（The 2% of reactant gross mass）, logical nitrogen protection is reacted about 7 hours under the conditions of 20 DEG C, until NCO contains
Amount reaches 7.8%, obtains isocyanates and partly blocks intermediate；
（2）By step（1）The isocyanates for obtaining half blocks intermediate and is reacted with castor oil（Molar ratio of material is 0.9:1）, temperature
Degree in 5 hours reaction time, until NCO content is less than 0.5%, obtains polyurethane acrylate prepolymer at 40 DEG C；
（3）By polyurethane acrylate prepolymer and light trigger 2- hydroxy-2-methyls propiophenone, diluent triethylene-glycol
Diacrylate presses mass fraction 78%：2%：20% ratio mixing, is sufficiently stirred for rear ultrasonic disperse 40 minutes, pours into a mould film forming, UV
Illumination obtain COPUA solidification batten, later stage heat cure condition be 120 DEG C 1 hour.Fig. 3-c are that the contact angle of COPUA is
112.15°
Embodiment 4
（1）Under conditions of hexamethylene is solvent, with isocyanates and pentaerythritol triacrylate as raw material（Isocyanates and
The molar ratio of material of acrylate is 0.7:1）, add catalyst dibutyltin dilaurate（The 3% of reactant gross mass）With
Hydroquinone of polymerization retarder（The 1% of reactant gross mass）, logical nitrogen protection is reacted about 4 hours under the conditions of 50 DEG C, until NCO contains
Amount reaches 7.5%, obtains isocyanates and partly blocks intermediate；
（2）By step（1）The isocyanates for obtaining half blocks intermediate and is reacted with castor oil（Molar ratio of material is 1:1.1）, temperature
Degree in 5 hours reaction time, until NCO content is less than 0.5%, obtains polyurethane acrylate prepolymer, by rotation at 80 DEG C
Evaporation of solvent.
（3）By polyurethane acrylate prepolymer and light trigger 2- hydroxy-2-methyls propiophenone, the acrylic acid of diluent three
Propane front three alcohol ester presses mass fraction 78%：2%：20% ratio mixing, is sufficiently stirred for rear ultrasonic disperse 30 minutes, pours into a mould film forming,
UV illumination obtain COPUA solidification batten, later stage heat cure condition be 120 DEG C 1 hour.Fig. 3-d are that the contact angle of COPUA is
109.81°
Embodiment 5
（1）In the absence of a solvent, with isocyanates and pentaerythritol triacrylate as raw material（Isocyanates and acrylic acid
The molar ratio of material of ester is 1.2:1）, add catalyst dibutyltin dilaurate（The 2% of reactant gross mass）And polymerization inhibitor
Hydroquinones（The 0.5% of reactant gross mass）, logical nitrogen protection is reacted about 2 hours under the conditions of 80 DEG C, until NCO content reaches
To 8%, obtain isocyanates and partly block intermediate；
（2）By step（1）The isocyanates for obtaining half blocks intermediate and is reacted with castor oil（Molar ratio of material is 1:1.2）, temperature
Degree in 7 hours reaction time, until NCO content is less than 0.5%, obtains polyurethane acrylate prepolymer at 70 DEG C；
（3）By polyurethane acrylate prepolymer and light trigger 2- hydroxy-2-methyls propiophenone, diluent hydroxy-ethyl acrylate
By mass fraction 68%：2%：30% ratio mixing, is sufficiently stirred for rear ultrasonic disperse 40 minutes, pours into a mould film forming, and UV illumination is obtained
COPUA solidifies batten.Fig. 3-e are 118.36 ° for the contact angle of COPUA
The invention is not restricted to above-described embodiment, can implement and with the good result described in present invention.
Claims (10)
1. a kind of preparation method of polyfunctionality castor oil-base light-cured resin, it is characterised in that comprise the following steps:
（1）With isocyanates and hydroxy acrylate as raw material, the catalyst and polymerization inhibitor of effective dose are added, lead to nitrogen protection,
Under the conditions of 20-120 DEG C, until NCO content reaches desired value 14% ~ 7%, obtain isocyanates and partly block intermediate, wherein different
The molar ratio of material of cyanate and hydroxy acrylate is 0.5-1.44:1, the reaction time is 2-10 hours；The polymerization inhibitor choosing
Any one from p methoxy phenol, MEHQ, hydroquinones, polymerization inhibitor consumption is reaction mass gross weight
0.5-4%；The catalyst is selected from any one in dibutyltin dilaurate, stannous octoate, dimethylethanolamine, catalysis
Agent consumption is the 1-5% of reaction mass gross weight；
（2）By step（1）The isocyanates for obtaining half blocks intermediate and is reacted with castor oil, and mol ratio is 0.6-0.8:1, temperature
It it is 30-140 DEG C, the reaction time is 3-12 hours, until NCO content is less than 0.5%, obtains polyurethane acrylate prepolymer；
（3）By polyurethane acrylate prepolymer, account for the light trigger of reactant gross mass 1%-5% and account for reactant gross mass not
Diluent mixing more than 40%, is sufficiently stirred for rear ultrasonic disperse, cast or film, and UV illumination obtains polyfunctionality castor oil-base
Light-cured resin.
2. preparation method according to claim 1, it is characterised in that the isocyanates described in step (1) is different containing two
The compound of cyanate group (- NCO) or its mixture, the compound are IPDI（IPDI）, first
Phenylene diisocyanate（TDI）, methyl diphenylene diisocyanate（MDI）, PPDI（PPDI）, the methylene of hexamethylene two
Group diisocyanate（HXDI）, norbornene alkyl diisocyanate（NBDI）In any one.
3. preparation method according to claim 1, it is characterised in that step（1）Described hydroxy acrylate is Ji Wusi
Alcohol triacrylate, Dipentaerythritol Pentaacrylate or trimethylolpropane diacrylate.
4. preparation method according to claim 1, it is characterised in that step（1）Described raw material is to react in a solvent,
The solvent is selected from n-hexane, butanone or hexamethylene, and in step（2）Solvent is removed finally by rotary evaporation.
5. preparation method according to claim 1, it is characterised in that step（2）The isocyanates half block intermediate with
The molar ratio of material of castor oil is 0.6:1.
6. preparation method according to claim 1, it is characterised in that step（3）The diluent be hydroxy-ethyl acrylate,
Hydroxyethyl methacrylate, hydroxy-ethyl acrylate, pentaerythritol triacrylate, triethylene-glycol diacrylate, 3 third
At least one in olefin(e) acid propane front three alcohol ester.
7. preparation method according to claim 1, it is characterised in that step（3）The light trigger is 2- hydroxyl -2- first
Base propiophenone, consumption accounts for the 2% of reactant gross mass.
8. preparation method according to claim 1, it is characterised in that step（3）The polyurethane acrylate prepolymer,
The mass ratio of light trigger and diluent is 0.78:0.02:0.2.
9. the polyfunctionality castor oil-base light-cured resin that any methods described of claim 1 ~ 8 is prepared.
10. the polyfunctionality castor oil-base light-cured resin described in claim 9 is in coating, ink or 3D printing material is prepared
Application.
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| CN114605598A (en) * | 2022-03-31 | 2022-06-10 | 长兴化学（天津）有限公司 | Bio-based dispersant, preparation method and application thereof |
| CN114686097A (en) * | 2020-12-25 | 2022-07-01 | 洛阳尖端技术研究院 | Castor oil modified photocuring wave-absorbing coating and preparation method thereof, and honeycomb sandwich wave-absorbing material and preparation method thereof |
| CN114736380A (en) * | 2022-05-23 | 2022-07-12 | 中国林业科学研究院林产化学工业研究所 | Light-curable castor oil-based shape memory elastomer and preparation method and application thereof |
| CN114835876A (en) * | 2022-05-20 | 2022-08-02 | 上海三桐材料科技有限公司 | Dual-curing polyurethane acrylate resin and preparation method thereof |
| CN115160917A (en) * | 2022-08-01 | 2022-10-11 | 浙江理工大学 | Ultraviolet-cured solvent-free polyurethane coating and preparation method thereof |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS565818A (en) * | 1979-06-28 | 1981-01-21 | Mitsubishi Electric Corp | Curable high polymer composition |
| CN102414233A (en) * | 2009-02-13 | 2012-04-11 | 拜尔材料科学股份公司 | Aqueous coating systems based on physically drying urethane acrylates |
| CN102702469A (en) * | 2012-06-20 | 2012-10-03 | 惠州市汉诺新材料有限公司 | Ultraviolet-curable aqueous polyurethane dispersion and preparation method thereof |
| CN103421156A (en) * | 2013-07-10 | 2013-12-04 | 华南理工大学 | UV curing resin, preparation method thereof and application of UV curing resin in UV curing colored paint |
| CN105542702A (en) * | 2015-12-23 | 2016-05-04 | 华南理工大学 | Ultraviolet-cured polyurethane adhesive and preparation method thereof |
-
2017
- 2017-02-24 CN CN201710101874.XA patent/CN106866929A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS565818A (en) * | 1979-06-28 | 1981-01-21 | Mitsubishi Electric Corp | Curable high polymer composition |
| CN102414233A (en) * | 2009-02-13 | 2012-04-11 | 拜尔材料科学股份公司 | Aqueous coating systems based on physically drying urethane acrylates |
| CN102702469A (en) * | 2012-06-20 | 2012-10-03 | 惠州市汉诺新材料有限公司 | Ultraviolet-curable aqueous polyurethane dispersion and preparation method thereof |
| CN103421156A (en) * | 2013-07-10 | 2013-12-04 | 华南理工大学 | UV curing resin, preparation method thereof and application of UV curing resin in UV curing colored paint |
| CN105542702A (en) * | 2015-12-23 | 2016-05-04 | 华南理工大学 | Ultraviolet-cured polyurethane adhesive and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| KAIBIN LI等: "Preparation and properties of castor oil/pentaerythritol triacrylate-based UV curable waterborne polyurethane acrylate", 《PROGRESS IN ORGANIC COATINGS》 * |
| VIKASH MISHRA等: "Development of Green Waterborne UV-Curable Castor Oil-Based Urethane Acrylate Coatings: Preparation and Property Analysis", 《INTERNATIONAL JOURNAL OF POLYMER ANALYSIS AND CHARACTERIZATION》 * |
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