CN111607183B - Styrene-acrylic copolymer resin and preparation method and application thereof - Google Patents
Styrene-acrylic copolymer resin and preparation method and application thereof Download PDFInfo
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- CN111607183B CN111607183B CN202010513962.2A CN202010513962A CN111607183B CN 111607183 B CN111607183 B CN 111607183B CN 202010513962 A CN202010513962 A CN 202010513962A CN 111607183 B CN111607183 B CN 111607183B
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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
- C08L35/00—Compositions of 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 a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/06—Copolymers with vinyl aromatic monomers
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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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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/087—Binders for toner particles
- G03G9/08702—Binders for toner particles comprising macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- G03G9/08706—Polymers of alkenyl-aromatic compounds
- G03G9/08708—Copolymers of styrene
- G03G9/08711—Copolymers of styrene with esters of acrylic or methacrylic acid
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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
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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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
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
- C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
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Abstract
The invention discloses a styrene-acrylic copolymer resin and a preparation method and application thereof, wherein the styrene-acrylic copolymer resin is prepared by co-extruding a resin A, a resin B and a resin C in the presence of a terpolymer; the preparation of the resin A comprises the steps of adding styrene, hydroxyethyl acrylate, monobutyl fumarate, an initiator and a crosslinking agent into boiling toluene, and removing a solvent after heat preservation reaction to obtain the resin A; the preparation of the resin B comprises the steps of adding styrene, butyl acrylate, an initiator and a cross-linking agent into boiling dimethylbenzene, then keeping refluxing and reacting at a constant temperature, and removing a solvent to obtain the resin B; the preparation of the resin C is that styrene, butyl methacrylate, an initiator and a cross-linking agent are added into boiling toluene, and the solvent is removed after the heat preservation reaction to obtain the resin C. The particle size of the random resin powder obtained by the invention is 0.5-1.5 mm, and the random resin powder is used for carbon powder printing and has good fixation firmness.
Description
Technical Field
The invention belongs to a high polymer synthesis technology, and particularly relates to styrene-acrylic copolymer resin and a preparation method and application thereof.
Background
Carbon powder resins used in printers and copiers are mostly styrene-acrylic copolymer resins, but in view of structural characteristics of the styrene-acrylic copolymer resins, the softening point (Ts) is also high at a relatively suitable glass transition temperature (Tg), so that the low-temperature fixing is not good, and the application of the styrene-acrylic copolymer resins in high-speed printers and copiers is also limited.
Disclosure of Invention
The invention discloses a styrene-acrylic copolymer resin and a preparation method and application thereof, wherein styrene-acrylic resins with different molecular weights are obtained through selection of monomers and limitation of polymer parameters, and then are co-extruded into sheets and crushed to obtain resin powder (the particle size is about 0.5-1.5 mm), so that the styrene-acrylic copolymer resin is used for carbon powder printing and has good fixation firmness.
The invention adopts the following technical scheme:
a styrene-acrylic copolymer resin is prepared by co-extruding a resin A, a resin B and a resin C in the presence of a terpolymer; the preparation of the resin A comprises the steps of adding styrene, hydroxyethyl acrylate, monobutyl fumarate, an initiator and a crosslinking agent into boiling toluene, and removing a solvent after heat preservation reaction to obtain the resin A; the preparation of the resin B comprises the steps of adding styrene, butyl acrylate, an initiator and a cross-linking agent into boiling dimethylbenzene, and removing a solvent after heat preservation reaction to obtain the resin B; the preparation of the resin C is that styrene, butyl methacrylate, an initiator and a cross-linking agent are added into boiling toluene, and the solvent is removed after the heat preservation reaction to obtain the resin C.
In the invention, the weight ratio of the resin A to the resin B to the resin C is 50: 30-40: 10-20, preferably 50: 35: 15; the prepared styrene-acrylic copolymer resin has good thermal property and electrical property according to a proper proportion, can be suitable for high-performance printing and particularly has good fixation firmness.
In the invention, the usage amount of the terpolymer is 0.5-0.6% of the sum of the weight of the resin A, the weight of the resin B and the weight of the resin C. The styrene-acrylic resin with good electrical property can be obtained by direct coextrusion without adding the terpolymer, but the fixation firmness is slightly low, the invention creatively adds the terpolymer originally used among different resins into the same resin A, the same resin B and the same resin C in a small amount, the printing property of a product obtained by coextrusion is improved, and the improvement of the uniformity of the properties of the three resins is possibly facilitated by adding the terpolymer.
In the invention, the cross-linking agent is divinyl benzene or butanediol diacrylate; the initiator is cumene hydroperoxide or di-tert-butyl peroxide.
In the invention, in the preparation of the resin A, the molar ratio of styrene to hydroxyethyl acrylate to the monobutyl fumarate is 7: 2: 1, the dosage of the initiator is 1.5 percent of the sum of the weight of the styrene, the hydroxyethyl acrylate and the monobutyl fumarate, and the dosage of the cross-linking agent is 5 percent of the sum of the weight of the styrene, the hydroxyethyl acrylate and the monobutyl fumarate; in the preparation of the resin B, the molar ratio of the styrene to the butyl acrylate is 8: 2, the dosage of the initiator is 2 percent of the sum of the weight of the styrene and the butyl acrylate, and the dosage of the cross-linking agent is 8 percent of the sum of the weight of the styrene and the butyl acrylate; in the preparation of the resin C, the molar ratio of the styrene to the butyl methacrylate is 3: 1, the dosage of the initiator is 4 percent of the sum of the weight of the styrene and the butyl methacrylate, and the dosage of the cross-linking agent is 3 percent of the sum of the weight of the styrene and the butyl methacrylate.
In the invention, in the preparation of the resin A, the reaction is carried out for 2.5 hours at the temperature of 110 ℃; in the preparation of the resin B, the reaction is carried out for 3 hours at the temperature of 140 ℃; in the preparation of the resin C, the reaction was carried out at 110 ℃ for 2 hours.
In the invention, the solvent is removed by vacuum reduced pressure distillation, and the operation of the vacuum reduced pressure distillation is a conventional technology, so that the solvent can be removed.
In the invention, the resin A, the resin B, the resin C and the terpolymer are added into a screw extruder, and styrene-acrylic copolymer resin is prepared by coextrusion; screw extrusion is a conventional technology, and the specific selection does not influence the realization of the technical effect of the invention.
Detailed Description
Example one
Weighing styrene, hydroxyethyl acrylate, monobutyl fumarate, an initiator cumene hydroperoxide and a cross-linking agent divinylbenzene by adopting a normal-pressure solution polymerization mode, and adding the weighed materials into a mixing tank to be fully and uniformly mixed for later use; adding toluene with the weight consistent with that of styrene, hydroxyethyl acrylate and monobutyl fumarate into a reactor, starting stirring, heating to boil, dropwise adding the liquid in the mixing tank into the boiling toluene at a constant speed, and keeping the dropwise addition of the mixed solution within 2 hours; then refluxing and reacting for 2.5 hours; after the reaction is finished, keeping the boiling reflux state, carrying out conventional vacuum-pumping reduced-pressure distillation, collecting distillate until no distillate flows out in the system, indicating that the solvent is completely removed, discharging the materials in the reactor, cooling, solidifying and crushing to obtain the resin A, wherein the number-average molecular weight is 1.0 ten thousand, and the molecular weight distribution is 3.89.
Accurately weighing styrene, butyl acrylate, initiator hydrogen peroxide di-tert-butyl and cross-linking agent butanediol diacrylate by adopting a normal-pressure solution polymerization mode, and adding the materials into a mixing tank to be fully and uniformly mixed for later use; adding styrene, butyl acrylate and xylene which is 0.75 times of the weight of the styrene and the butyl acrylate into a reactor, sealing, starting stirring, heating to 140 ℃, dropwise adding the liquid in the mixing tank into the reactor at a constant speed, and keeping the dropwise addition of the mixed liquid within 5 hours to complete; the reaction was then maintained at a constant temperature of 140 ℃ for 3 hours. And then, evacuating and depressurizing, carrying out conventional vacuumizing and reduced pressure distillation, collecting distillate until no distillate flows out in the system, indicating that the solvent is completely removed, discharging the materials in the reactor, cooling, solidifying and crushing to obtain the resin B, wherein the number average molecular weight is 2.5 ten thousand, and the molecular weight distribution is 3.27.
Weighing styrene, butyl methacrylate, an initiator cumene hydroperoxide and a cross-linking agent butanediol diacrylate by adopting a normal-pressure solution polymerization mode, and adding the weighed materials into a mixing tank to be fully and uniformly mixed for later use; adding styrene and 1.1 times of toluene by weight of butyl methacrylate into a reactor, starting stirring, heating to boil, dropwise adding the liquid in the mixing tank into the boiling toluene at a constant speed, and keeping the dropwise addition of the mixed solution within 3 hours; the reaction was then refluxed for 2 hours. After that, the boiling reflux state is maintained to carry out the conventional vacuum-pumping reduced pressure distillation, and the distillate is collected until no distillate flows out in the system, which indicates that the solvent is completely removed. Discharging the materials in the reactor, cooling, solidifying and crushing to obtain the resin C with the number average molecular weight of 1.1 ten thousand and the molecular weight distribution of 2.76.
In the preparation of the resin A, the mol ratio of styrene to hydroxyethyl acrylate to monobutyl fumarate is 7: 2: 1, the dosage of the initiator is 1.5 percent of the sum of the weight of the styrene, the hydroxyethyl acrylate and the monobutyl fumarate, and the dosage of the cross-linking agent is 5 percent of the sum of the weight of the styrene, the hydroxyethyl acrylate and the monobutyl fumarate; in the preparation of the resin B, the molar ratio of the styrene to the butyl acrylate is 8: 2, the dosage of the initiator is 2 percent of the sum of the weight of the styrene and the butyl acrylate, and the dosage of the cross-linking agent is 8 percent of the sum of the weight of the styrene and the butyl acrylate; in the preparation of the resin C, the molar ratio of the styrene to the butyl methacrylate is 3: 1, the dosage of the initiator is 4 percent of the sum of the weight of the styrene and the butyl methacrylate, and the dosage of the cross-linking agent is 3 percent of the sum of the weight of the styrene and the butyl methacrylate.
Adding 50 parts by weight of resin A, 35 parts by weight of resin B, 15 parts by weight of resin C and 0.5 part by weight of terpolymer into a screw extruder, co-extruding to prepare styrene-acrylic copolymer resin, and packaging crushed resin powder (with the particle size of 0.5-1.5 mm) to obtain a resin finished product for preparing carbon powder.
The terpolymer is AN existing substance, specifically is ST-AN-GMA (70-25-5) terpolymer with number average molecular weight of 15000, wherein styrene content is 70%, acrylonitrile content is 25%, and glycerol methacrylate content is 5%.
The invention adopts a solution polymerization mode, is relatively safe and reliable, and has stable quality; the finished product is solid powder, is convenient to store and transport, and does not form hazardous waste; the carbon powder prepared by the resin has obvious advantages in low-temperature fixation compared with the conventional styrene-acrylic resin.
Application examples
According to parts by weight, 100 parts of styrene-acrylic copolymer resin powder, 8.8 parts of carbon black, 1.8 parts of polyethylene wax (molecular weight 4000), 3 parts of zinc compound of 3, 5-di-tert-butyl salicylic acid and 1.5 parts of silicon micropowder are premixed in a conventional mixer for 15 minutes and then added into a mixing machine, mixed for 20 minutes conventionally, discharged materials are cooled and then crushed, and sieved to obtain 5-12 micron powder which is carbon powder.
And a small amount of the kneaded and discharged material is taken for tabletting, and the dispersibility of the carbon black is good through observation of a transmission electron microscope.
The carbon powder is used for printing sample paper (the conventional operations such as ink box loading and the like are the same as the prior art), the sample paper is provided with solid circles and is used for testing the fixation firmness, the solid circles are rubbed by adopting a national office equipment and consumable material quality supervision and inspection center (OAT Tianjin) MC-3 friction tester, the fixation firmness is obtained by testing the density values of the solid circles before and after rubbing by the conventional method, the specific testing method is the prior art, and each carbon powder is measured ten times.
Tests prove that the carbon powder prepared from the styrene-acrylic copolymer resin has excellent fixation fastness of 90-91%.
If the amounts of 50 parts of resin A, 35 parts of resin B and 15 parts of resin C are adjusted to 53 parts of resin A, 37 parts of resin B and 10 parts of resin C, and the rest are unchanged, the prepared carbon powder has good fixing fastness which is 80-84% through the same test.
Comparative example 1
According to the weight parts, 50 parts of resin A, 35 parts of resin B and 15 parts of resin C are premixed in a conventional mixer for 30 minutes, then premixed with 8.8 parts of carbon black, 1.8 parts of polyethylene wax (molecular weight 4000), 3 parts of zinc compound of 3, 5-di-tert-butyl salicylic acid and 1.5 parts of silicon micropowder in the conventional mixer for 15 minutes, added into a mixing machine, mixed for 20 minutes conventionally, and crushed after discharging and cooling to obtain powder of 5-12 micrometers, namely carbon powder. By adopting the same test method, the fixing fastness is 75-78%.
Comparative example No. two
Adding 50 parts by weight of resin A, 35 parts by weight of resin B and 15 parts by weight of resin C into a screw extruder, co-extruding to prepare styrene-acrylic copolymer resin, and crushing to obtain 0.5-1.5 mm resin powder for preparing carbon powder.
According to parts by weight, 100 parts of styrene-acrylic copolymer resin powder, 8.8 parts of carbon black, 1.8 parts of polyethylene wax (with the molecular weight of 4000), 3 parts of zinc compound of 3, 5-di-tert-butyl salicylic acid and 1.5 parts of silicon micropowder are premixed in a conventional mixer for 15 minutes and then added into a mixing machine, the mixture is mixed for 20 minutes conventionally, and after discharging and cooling, the mixture is crushed and sieved to obtain 5-12 micron powder which is carbon powder.
By adopting the same test method, the fixation fastness is good and is 83-85%.
Comparative example No. three
Adding 50 parts by weight of resin A, 35 parts by weight of resin B and 0.425 part by weight of terpolymer into a screw extruder, co-extruding to prepare styrene-acrylic copolymer resin, and crushing to obtain 0.5-1.5 mm of resin powder for preparing carbon powder.
According to parts by weight, 100 parts of styrene-acrylic copolymer resin powder, 8.8 parts of carbon black, 1.8 parts of polyethylene wax (molecular weight 4000), 3 parts of zinc compound of 3, 5-di-tert-butyl salicylic acid and 1.5 parts of silicon micropowder are premixed in a conventional mixer for 15 minutes and then added into a mixing machine, mixed for 20 minutes conventionally, discharged materials are cooled and then crushed, and sieved to obtain 5-12 micron powder which is carbon powder.
By adopting the same test method, the fixing fastness is 70-72% below the middle.
According to the invention, the front-stage copolymer is used as a molecular weight regulator, and the styrene-acrylic resins with different molecular weights are combined, so that the Ts is properly reduced and the low-temperature fixing performance of the styrene-acrylic copolymer resin is improved on the premise of keeping the Tg and the good electrical property of the styrene-acrylic copolymer resin.
Claims (6)
1. A styrene-acrylic copolymer resin is prepared by co-extruding a resin A, a resin B and a resin C in the presence of a terpolymer; the preparation of the resin A comprises the steps of adding styrene, hydroxyethyl acrylate, monobutyl fumarate, an initiator and a crosslinking agent into boiling toluene, and removing a solvent after heat preservation reaction to obtain the resin A; the preparation of the resin B comprises the steps of adding styrene, butyl acrylate, an initiator and a cross-linking agent into boiling dimethylbenzene, and removing a solvent after heat preservation reaction to obtain the resin B; the preparation of the resin C comprises the steps of adding styrene, butyl methacrylate, an initiator and a cross-linking agent into boiling toluene, carrying out heat preservation reaction, and removing a solvent to obtain the resin C; the terpolymer is ST-AN-GMA terpolymer with number average molecular weight of 15000, wherein the styrene content is 70%, the acrylonitrile content is 25%, and the methacrylic acid glyceride is 5%; the weight ratio of the resin A to the resin B to the resin C is 50: 35: 15; the using amount of the terpolymer is 0.5-0.6% of the sum of the weight of the resin A, the weight of the resin B and the weight of the resin C; the cross-linking agent is divinyl benzene or butanediol diacrylate; the initiator is cumene hydroperoxide or di-tert-butyl peroxide.
2. The styrene-acrylic copolymer resin as claimed in claim 1, wherein the molar ratio of styrene to hydroxyethyl acrylate to monobutyl fumarate in the preparation of the resin A is 7: 2: 1, the dosage of the initiator is 1.5 percent of the weight sum of the styrene, the hydroxyethyl acrylate and the monobutyl fumarate, and the dosage of the cross-linking agent is 5 percent of the weight sum of the styrene, the hydroxyethyl acrylate and the monobutyl fumarate.
3. The styrene-acrylic copolymer resin as claimed in claim 1, wherein in the preparation of the resin B, the molar ratio of styrene to butyl acrylate is 8: 2, the dosage of the initiator is 2% of the sum of the weights of the styrene and the butyl acrylate, and the dosage of the cross-linking agent is 8% of the sum of the weights of the styrene and the butyl acrylate; in the preparation of the resin C, the molar ratio of the styrene to the butyl methacrylate is 3: 1, the dosage of the initiator is 4 percent of the sum of the weight of the styrene and the butyl methacrylate, and the dosage of the cross-linking agent is 3 percent of the sum of the weight of the styrene and the butyl methacrylate.
4. The styrene-acrylic copolymer resin as claimed in claim 1, wherein in the preparation of the resin A, the reaction is carried out for 2.5 hours at 110 ℃; in the preparation of the resin B, the reaction is carried out for 3 hours at the temperature of 140 ℃; in the preparation of the resin C, the reaction is carried out for 2 hours at 110 ℃.
5. Use of the styrene-acrylic copolymer resin as defined in claim 1 for the preparation of carbon powder.
6. The use according to claim 5, wherein said carbon powder has a constant temperature fixing fastness property.
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| CN202010513962.2A CN111607183B (en) | 2020-06-08 | 2020-06-08 | Styrene-acrylic copolymer resin and preparation method and application thereof |
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| CN111607183B true CN111607183B (en) | 2022-05-13 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2022283C (en) * | 1989-07-31 | 1996-07-30 | Takayoshi Matsunaga | Resin composition for toners and a toner containing the same |
| CN101851321B (en) * | 2009-04-03 | 2012-05-23 | 上海日之升新技术发展有限公司 | Terpolymer resin and preparation method thereof |
| CN102731922B (en) * | 2012-07-20 | 2013-10-09 | 张家港威迪森化学有限公司 | Copolymer resin for powdered ink and preparation method thereof |
| CN111057173A (en) * | 2019-12-19 | 2020-04-24 | 张家港威迪森化学有限公司 | Styrene-acrylic copolymer resin with good low-temperature fixation and preparation method thereof |
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