CN105504140A - Synthetic method of high-hydroxyl-value acrylic resin - Google Patents
Synthetic method of high-hydroxyl-value acrylic resin Download PDFInfo
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- CN105504140A CN105504140A CN201610015071.8A CN201610015071A CN105504140A CN 105504140 A CN105504140 A CN 105504140A CN 201610015071 A CN201610015071 A CN 201610015071A CN 105504140 A CN105504140 A CN 105504140A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—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 an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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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
- C09D125/00—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 an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
- C09D125/04—Homopolymers or copolymers of styrene
- C09D125/08—Copolymers of styrene
- C09D125/14—Copolymers of styrene with unsaturated esters
-
- 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
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
- C09D133/12—Homopolymers or copolymers of methyl methacrylate
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- 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a synthetic method of high-hydroxyl-value acrylic resin. The synthetic method includes the steps that 17-25 parts, by weight, of hard monomers, 5-15 parts, by weight, of soft monomers, 13-25 parts, by weight, of hydroxyl monomers, 0-2.5 parts, by weight, of carboxylic monomers and 0.3-1.5 parts, by weight, of initiator are mixed to be uniform, and a material a is obtained; 30-35 parts of organic solvent is added into a reaction container, the temperature is raised to 70-90 DEG C, backflow is stable, the material a is dropwise added for 4-5 hours, then the temperature is maintained for 1-1.5 hours, and a material b is obtained; 5-10 parts of the organic solvent and 0.1-0.7 parts of the initiator are mixed to be uniform, and a material c is obtained; the material c is dropwise added to the material b for 0.5-1.5 hours, then the temperature is maintained for 2-3 hours, then the temperature is lowered to 60 DEG C and below, 4-9 parts of the organic solvent is added to adjust the resin viscosity and the solid content, and the high-hydroxyl-value acrylic resin is obtained. The synthetic method is easy, convenient and safe, the hydroxyl value of the obtained resin is high, the compatibility with toner is high, and adhesive force and fullness are good.
Description
Technical field
The present invention relates to functional high-polymer resin technology field, particularly relate to a kind of Hydroxylated acrylic resin preparation method.
Background technology
Existing Hydroxylated acrylic resin synthesis; adopt logical protection of inert gas high―temperature nuclei; energy consumption high safety factor is low; the not volatile VOC of solvent is residual many; resin hydroxyl value all can not more than 130mgKOH/g, and after the dark toner of use vast scale, fullness ratio and guarantor's light protect degradation in the performance such as look, metal adhesion.High hydroxyl value acrylic resin, has fine toner and the base material general character; Using excellent to metal adhesion to the dark toner of vast scale is this money high hydroxyl value acrylic resin feature.Significantly optimum synthesis process modification is filled a prescription simultaneously, reduces energy consumption, safety simple to operate is easily controlled, VOC residual quantity is low, has responded national environmental protection call.
Summary of the invention
Based on the technical problem that background technology exists, the present invention proposes a kind of high hydroxyl value acrylic resin synthetic method, method safety, be easy to control, save energy consumption, easy and simple to handle, gained resin VOC remains low, has widened the scope of application, can arrange in pairs or groups with water-borne coatings and use, its hydroxyl value, up to 130 ~ 165mgKOH/g, has the compatible consistency of fine toner, and sticking power, fullness ratio and guarantor's light unfading are good.
The one high hydroxyl value acrylic resin synthetic method that the present invention proposes, comprises the steps:
S1, the initiator of 17 ~ 25 parts of hard monomers, 5 ~ 15 parts of soft monomers, 13 ~ 25 parts of carboxylic monomers, 0 ~ 2.5 part of carboxylic monomer and 0.3 ~ 1.5 part is mixed obtain material a by weight;
S2, in reaction vessel, add 30 ~ 35 parts of organic solvents, be warming up to 70 ~ 90 DEG C, after reflux stabilizes, then drip material a, time for adding is 4 ~ 5h, is then incubated 1 ~ 1.5h and obtains material b;
S3,5 ~ 10 parts of organic solvents and 0.1 ~ 0.7 part of initiator are mixed obtain material c; In material b, drip material c, time for adding is 0.5 ~ 1.5h, is then incubated 2 ~ 3h, is then cooled to less than 60 DEG C, adds 4 ~ 9 parts of organic solvents adjustment resin viscosities and solid content obtains high hydroxyl value acrylic resin.
Preferably, in S1, the initiator of 20 ~ 22 parts of hard monomers, 8 ~ 12 parts of soft monomers, 18 ~ 22 parts of carboxylic monomers, 0 ~ 1.5 part of carboxylic monomer and 0.8 ~ 1.2 part is mixed obtain material a by weight.
Preferably, in S3, add 6 ~ 8 parts of organic solvent adjustment viscosity and solid content.
Preferably, organic solvent is one or more compositions in n-propyl acetate, ethyl acetate, butanone, Virahol.
Preferably, hard monomer is one or more compositions in methyl methacrylate, β-dimethyl-aminoethylmethacrylate, phenyl methacrylate, vinylbenzene, isobornyl methacrylate.
Preferably, soft monomer is one or more compositions in methyl acrylate, ethyl propenoate, propyl acrylate, butyl acrylate, ethyl acrylate, n-BMA, methacrylic acid-2-ethylhexyl, octadecyl methacrylate.
Preferably, carboxylic monomer is one or more compositions in Hydroxyethyl acrylate, Propylene glycol monoacrylate, hy-droxybutyl, hydroxyethyl methylacrylate, Rocryl 410, methacrylate.
Preferably, carboxylic monomer is one or more compositions in vinylformic acid, methacrylic acid, maleic acid, FUMARIC ACID TECH GRADE.
Preferably, initiator is one or more compositions in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), benzoyl peroxide, peroxidized t-butyl perbenzoate, tertbutyl peroxide, di-t-butyl peroxide, peroxide-2-ethyl hexanoic acid tert-butyl, di t-amyl peroxide.
Beneficial effect of the present invention is as follows:
1, VOC of the present invention remains low, has widened the scope of application, can arrange in pairs or groups use with water-borne coatings;
2, the present invention adopts low temperature to synthesize in normal temperature and pressure environment, and reaction safety is easy to control, and saves energy consumption, easy and simple to handle;
3, the hydroxyl value of gained resin of the present invention is up to 130 ~ 165mgKOH/g, have the compatible consistency of fine toner, and sticking power is outstanding, and fullness ratio is good with guarantor's light unfading; When two component uses, temperature tolerance can reach 170 ~ 190 DEG C.
Embodiment
Below, by specific embodiment, technical scheme of the present invention is described in detail.
Embodiment 1
The one high hydroxyl value acrylic resin synthetic method that the present invention proposes, comprises the steps:
S1, by weight 21 parts of methyl methacrylates, 13 parts of n-BMAs, 18 parts of hydroxyethyl methylacrylates, 2 parts of vinylformic acid and 1 part of 2,2'-Azobis(2,4-dimethylvaleronitrile) are mixed and obtain material a;
S2, in reaction vessel, add 30 parts of butanone, be warming up to 78 ~ 80 DEG C, after reflux stabilizes, then drip material a, time for adding is 4h, is then incubated 1h and obtains material b;
S3,10 parts of butanone and 0.7 part of 2,2'-Azobis(2,4-dimethylvaleronitrile) are mixed obtain material c; In material b, drip material c, time for adding is 1h, is then incubated 2h, is then cooled to less than 60 DEG C, then adds 6 parts of butanone adjustment viscosity and solid content obtains high hydroxyl value acrylic resin.
Embodiment 2
The one high hydroxyl value acrylic resin synthetic method that the present invention proposes, comprises the steps:
S1, by weight 10 parts of methyl methacrylates and 15 parts of vinylbenzene, 13 parts of butyl acrylates, 15 parts of hydroxyethyl methylacrylates, 1 part of vinylformic acid and 1 part of Diisopropyl azodicarboxylate are mixed and obtain material a;
S2, in reaction vessel, add 15 portions of n-propyl acetates and 15 parts of Virahols, be warming up to 80 ~ 85 DEG C, after reflux stabilizes, then drip material a, time for adding is 5h, is then incubated 1h and obtains material b;
S3,10 portions of n-propyl acetates and 0.7 part of Diisopropyl azodicarboxylate are mixed obtain material c; In material b, drip material c, time for adding is 1h, is then incubated 2h, is then cooled to less than 60 DEG C, then adds 6 parts of butanone adjustment viscosity and solid content obtains high hydroxyl value acrylic resin.
Embodiment 3
The one high hydroxyl value acrylic resin synthetic method that the present invention proposes, comprises the steps:
S1, by weight 21 parts of methyl methacrylates, 13 parts of butyl acrylates, 18 parts of hydroxyethyl methylacrylates, 2 parts of methacrylic acids and 1 part of 2,2'-Azobis(2,4-dimethylvaleronitrile) are mixed and obtain material a;
S2, in reaction vessel, add 30 parts of butanone, be warming up to 78 ~ 80 DEG C, after reflux stabilizes, then drip material a, time for adding is 4h, is then incubated 1h and obtains material b;
S3,10 parts of butanone and 0.7 part of 2,2'-Azobis(2,4-dimethylvaleronitrile) are mixed obtain material c; In material b, drip material c, time for adding is 1h, is then incubated 2h, is then cooled to less than 60 DEG C, then adds 6 parts of butanone adjustment viscosity and solid content obtains high hydroxyl value acrylic resin.
Embodiment 4
The one high hydroxyl value acrylic resin synthetic method that the present invention proposes, comprises the steps:
S1, by weight 21 parts of methyl methacrylates, 13 parts of butyl acrylates, 18 parts of hydroxyethyl methylacrylates, 1 part of methacrylic acid and 1 part of peroxide-2-ethyl hexanoic acid tert-butyl are mixed and obtain material a;
S2, in reaction vessel, add 20 parts of ethyl acetate and 10 parts of Virahols, be warming up to 78 ~ 80 DEG C, after reflux stabilizes, then drip material a, time for adding is 5h, is then incubated 1h and obtains material b;
S3,10 parts of Virahols and 0.7 part of peroxide-2-ethyl hexanoic acid tert-butyl are mixed obtain material c; In material b, drip material c, time for adding is 1h, is then incubated 3h, is then cooled to less than 60 DEG C, then adds 6 parts of butanone adjustment viscosity and solid content obtains high hydroxyl value acrylic resin.
Embodiment 5
The one high hydroxyl value acrylic resin synthetic method that the present invention proposes, comprises the steps:
S1, by weight 8 parts of methyl methacrylates, 12 parts of vinylbenzene, 13 parts of n-BMAs, 15 parts of hydroxyethyl methylacrylates, 4 parts of Propylene glycol monoacrylates, 1 part of methacrylic acid and 1 part of 2,2'-Azobis(2,4-dimethylvaleronitrile) are mixed and obtain material a;
S2, in reaction vessel, add 15 portions of n-propyl acetates and 15 parts of Virahols, be warming up to 80 ~ 85 DEG C, after reflux stabilizes, then drip material a, time for adding is 5h, is then incubated 1h and obtains material b;
S3,10 portions of n-propyl acetates and 0.7 part of 2,2'-Azobis(2,4-dimethylvaleronitrile) are mixed obtain material c; In material b, drip material c, time for adding is 1h, is then incubated 2h, is then cooled to less than 60 DEG C, then adds 6 parts of butanone adjustment viscosity and solid content obtains high hydroxyl value acrylic resin.
In embodiment 1-5 gained high hydroxyl value acrylic resin, add polyisocyanate curing agent, thinner, toner, auxiliary agent etc. be mixed with coating.By coatings on water-based release film, 170 DEG C of baking 40s, then aluminize and do total transfer, test to metal adhesion and toner consistency, heat resistance, water-based from property film versatility, and wherein, temperature tolerance test adopts baking oven baking method; Metal adhesion test uses extraordinary mightiness belt reverse drawing, and whether observation coating and metal are peeled off and come off.Its performance test results is as follows:
The above; be only the present invention's preferably embodiment; but protection scope of the present invention is not limited thereto; anyly be familiar with those skilled in the art in the technical scope that the present invention discloses; be equal to according to technical scheme of the present invention and inventive concept thereof and replace or change, all should be encompassed within protection scope of the present invention.
Claims (9)
1. a high hydroxyl value acrylic resin synthetic method, is characterized in that, comprise the steps:
S1, the initiator of 17 ~ 25 parts of hard monomers, 5 ~ 15 parts of soft monomers, 13 ~ 25 parts of carboxylic monomers, 0 ~ 2.5 part of carboxylic monomer and 0.3 ~ 1.5 part is mixed obtain material a by weight;
S2, in reaction vessel, add 30 ~ 35 parts of organic solvents, be warming up to 70 ~ 90 DEG C, after reflux stabilizes, then drip material a, time for adding is 4 ~ 5h, is then incubated 1 ~ 1.5h and obtains material b;
S3,5 ~ 10 parts of organic solvents and 0.1 ~ 0.7 part of initiator are mixed obtain material c; In material b, drip material c, time for adding is 0.5 ~ 1.5h, is then incubated 2 ~ 3h, is then cooled to less than 60 DEG C, adds 4 ~ 9 parts of organic solvents adjustment resin viscosities and solid content obtains high hydroxyl value acrylic resin.
2. high hydroxyl value acrylic resin synthetic method according to claim 1, it is characterized in that, in S1, the initiator of 20 ~ 22 parts of hard monomers, 8 ~ 12 parts of soft monomers, 18 ~ 22 parts of carboxylic monomers, 0 ~ 1.5 part of carboxylic monomer and 0.8 ~ 1.2 part is mixed obtain material a by weight.
3. high hydroxyl value acrylic resin synthetic method according to claim 1 or 2, is characterized in that, in S3, adds 6 ~ 8 parts of organic solvent adjustment viscosity and solid content.
4. high hydroxyl value acrylic resin synthetic method according to any one of claim 1-3, is characterized in that, organic solvent is one or more compositions in n-propyl acetate, ethyl acetate, butanone, Virahol.
5. high hydroxyl value acrylic resin synthetic method according to any one of claim 1-4, it is characterized in that, hard monomer is one or more compositions in methyl methacrylate, β-dimethyl-aminoethylmethacrylate, phenyl methacrylate, vinylbenzene, isobornyl methacrylate.
6. high hydroxyl value acrylic resin synthetic method according to any one of claim 1-5, it is characterized in that, soft monomer is one or more compositions in methyl acrylate, ethyl propenoate, propyl acrylate, butyl acrylate, ethyl acrylate, n-BMA, methacrylic acid-2-ethylhexyl, octadecyl methacrylate.
7. high hydroxyl value acrylic resin synthetic method according to any one of claim 1-6, it is characterized in that, carboxylic monomer is one or more compositions in Hydroxyethyl acrylate, Propylene glycol monoacrylate, hy-droxybutyl, hydroxyethyl methylacrylate, Rocryl 410, methacrylate.
8. high hydroxyl value acrylic resin synthetic method according to any one of claim 1-7, is characterized in that, carboxylic monomer is one or more compositions in vinylformic acid, methacrylic acid, maleic acid, FUMARIC ACID TECH GRADE.
9. high hydroxyl value acrylic resin synthetic method according to any one of claim 1-8, it is characterized in that, initiator is one or more compositions in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), benzoyl peroxide, peroxidized t-butyl perbenzoate, tertbutyl peroxide, di-t-butyl peroxide, peroxide-2-ethyl hexanoic acid tert-butyl, di t-amyl peroxide.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201610015071.8A CN105504140A (en) | 2016-01-08 | 2016-01-08 | Synthetic method of high-hydroxyl-value acrylic resin |
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| CN201610015071.8A CN105504140A (en) | 2016-01-08 | 2016-01-08 | Synthetic method of high-hydroxyl-value acrylic resin |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106084143A (en) * | 2016-06-29 | 2016-11-09 | 潍坊富乐新材料有限公司 | A kind of low VOC Hydroxylated acrylic resin and preparation technology thereof |
| CN107828026A (en) * | 2017-11-15 | 2018-03-23 | 六安科瑞达新型材料有限公司 | A kind of modified high hydroxyl value solid propenoic acid resin and preparation method thereof |
| CN110105488A (en) * | 2019-04-28 | 2019-08-09 | 英德市雅家涂料有限公司 | A kind of high abrasion Hydroxylated acrylic resin and its preparation process |
| CN111019469A (en) * | 2019-12-05 | 2020-04-17 | 立邦涂料（中国）有限公司 | Acrylic-based overprint varnish compositions, varnishes and uses thereof |
| CN114181366A (en) * | 2021-12-30 | 2022-03-15 | 广东裕田霸力科技股份有限公司 | Modified acrylic polyol composition |
| CN114316116A (en) * | 2020-10-21 | 2022-04-12 | 广东邦固薄膜涂料创新研究院有限公司 | Antibacterial acrylic resin and preparation method and application thereof |
| CN116042019A (en) * | 2023-02-23 | 2023-05-02 | 重庆宏图新材料科技有限公司 | Environment-friendly ink special for temperature change of food packaging bag and preparation method thereof |
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| KR20150134154A (en) * | 2014-05-21 | 2015-12-01 | 주식회사 대현에스티 | Manufacturing method of heat-peelable adhesive sheet or adhesive tape using uv curing system |
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| US20110081505A1 (en) * | 2005-09-08 | 2011-04-07 | 3M Innovative Properties Company | Adhesive composition and articles made therefrom |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106084143A (en) * | 2016-06-29 | 2016-11-09 | 潍坊富乐新材料有限公司 | A kind of low VOC Hydroxylated acrylic resin and preparation technology thereof |
| CN106084143B (en) * | 2016-06-29 | 2019-07-09 | 潍坊富乐新材料有限公司 | A kind of low VOC Hydroxylated acrylic resin and its preparation process |
| CN107828026A (en) * | 2017-11-15 | 2018-03-23 | 六安科瑞达新型材料有限公司 | A kind of modified high hydroxyl value solid propenoic acid resin and preparation method thereof |
| CN110105488A (en) * | 2019-04-28 | 2019-08-09 | 英德市雅家涂料有限公司 | A kind of high abrasion Hydroxylated acrylic resin and its preparation process |
| CN110105488B (en) * | 2019-04-28 | 2021-12-07 | 英德市雅家涂料有限公司 | High-wear-resistance hydroxyl acrylic resin and preparation process thereof |
| CN111019469A (en) * | 2019-12-05 | 2020-04-17 | 立邦涂料（中国）有限公司 | Acrylic-based overprint varnish compositions, varnishes and uses thereof |
| CN114316116A (en) * | 2020-10-21 | 2022-04-12 | 广东邦固薄膜涂料创新研究院有限公司 | Antibacterial acrylic resin and preparation method and application thereof |
| CN114181366A (en) * | 2021-12-30 | 2022-03-15 | 广东裕田霸力科技股份有限公司 | Modified acrylic polyol composition |
| CN114181366B (en) * | 2021-12-30 | 2023-11-07 | 广东裕田霸力科技股份有限公司 | Modified acrylic polyol composition |
| CN116042019A (en) * | 2023-02-23 | 2023-05-02 | 重庆宏图新材料科技有限公司 | Environment-friendly ink special for temperature change of food packaging bag and preparation method thereof |
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