CN114957566A - Polyester styrene-acrylic grafted powdered ink resin and preparation method thereof - Google Patents
Polyester styrene-acrylic grafted powdered ink resin and preparation method thereof Download PDFInfo
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- CN114957566A CN114957566A CN202210595851.XA CN202210595851A CN114957566A CN 114957566 A CN114957566 A CN 114957566A CN 202210595851 A CN202210595851 A CN 202210595851A CN 114957566 A CN114957566 A CN 114957566A
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- polyester
- styrene
- acid
- grafted
- acrylic
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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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- 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
Abstract
The invention provides a polyester styrene-acrylic grafted ink powder resin, which comprises the following components: polyester and styrene-acrylic resin grafted with polyester; wherein the polyester comprises: alcohol and acid, and a catalyst, wherein the styrene-acrylic resin comprises: the solvent comprises a monomer, an initiator, a cross-linking agent, a chain transfer agent and a xylene solvent. The polyester and styrene-acrylic resin copolymerized grafted resin can ensure a lower softening point temperature under the condition of high glass transition temperature, thereby meeting the requirement of low-temperature rapid fixation.
Description
Technical Field
The invention relates to the field of toner resins, in particular to a polyester styrene-acrylic grafted toner resin and a preparation method thereof.
Background
The demand for printing and copying is increasing, toner resins are required to meet the requirements of color density, low-temperature rapid fixing and non-stick fixing, and a single resin or polyester cannot meet the requirements.
Disclosure of Invention
In order to solve the technical problem, the invention provides a polyester styrene-acrylic grafted toner resin, which comprises the following components: polyester and styrene-acrylic resin grafted with polyester;
wherein the polyester comprises: alcohol, acid and catalyst
Wherein, the styrene-acrylic resin comprises: the solvent comprises a monomer, an initiator, a cross-linking agent, a chain transfer agent and a xylene solvent.
Preferably, the alcohol comprises: neopentyl glycol, trimethylolpropane, dihydroxyethoxy bisphenol A and cyclohexanediol.
Preferably, the acid comprises: adipic acid, isophthalic acid, maleic anhydride, terephthalic acid, phthalic anhydride, benzoic acid, and t-butyl benzoic acid.
Preferably, the catalyst comprises: tetrabutyl titanate and monobutyl tin oxide or the combination of the tetrabutyl titanate and the monobutyl tin oxide.
Preferably, the monomers include: one or more of styrene, n-butyl acrylate, isooctyl acrylate, methyl methacrylate, acrylic acid, maleic anhydride and monobutyl maleate.
Preferably, the initiator comprises: cumene hydroperoxide, dicumyl peroxide and ditert-butyl peroxide.
Preferably, the crosslinking agent comprises: divinylbenzene.
Preferably, the chain transfer agent comprises: one or both of dodecyl mercaptan and alpha-methylstyrene linear dimer.
Preferably, the preparation method for the polyester styrene-acrylic grafted toner resin comprises the steps of putting 60-80 parts of dimethylbenzene serving as a solvent into a reactor according to mass fraction, simultaneously putting 10-20 parts of polyester, starting stirring and heating to 140 ℃;
then uniformly mixing 80-90 parts of monomer, 1-5 parts of initiator, 1-5 parts of cross-linking agent and 1-5 parts of chain transfer agent, and then dropwise adding the mixture into a xylene solvent at 140 ℃, wherein the dropwise adding time is 3-5 hours, the reflux state is kept, the temperature is controlled at 140 +/-2 ℃, and the temperature is kept for 3 hours after the dropwise adding is finished;
after the heat preservation is finished, heating to 170 ℃ to remove the solvent, gradually increasing the negative pressure, and when the pressure reaches-0.096 MPa and no solvent flows out, indicating that the solvent is completely removed from the reaction solution;
discharging the residual product in the reactor, cooling and crushing to obtain the polyester styrene-acrylic grafted powdered ink resin.
Preferably, the preparation method for the polyester comprises the following preparation steps: firstly putting corresponding alcohol and acid into a reactor according to the mol ratio of the alcohol to the acid of 1.2-1.5:1, simultaneously adding a catalyst, heating to 150 ℃, starting stirring, slowly heating to 230 ℃ at the speed of 15-20 ℃ per hour, putting monobasic acid for end capping when the water yield reaches the requirement, and finally removing water in vacuum.
The invention has the following advantages:
the polyester and styrene-acrylic resin copolymerized graft resin can ensure lower softening point temperature under the condition of high glass transition temperature, thereby meeting the requirement of low-temperature rapid fixation.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention.
The present invention will be described in further detail with reference to examples and specific embodiments.
Example 1:
the preparation method of the polyester comprises the following steps: 178.3g of neopentyl glycol, 38.3g of trimethylolpropane, 284.6g of isophthalic acid and 14g of maleic anhydride are sequentially put into a 1L four-port glass reaction kettle according to the principle of alcohol first and acid second, and finally 3g of tetrabutyl titanate is added.
Heating to 150 ℃, starting stirring when stirring can rotate without resistance, heating to 170 ℃ after all the materials are dissolved, heating to 170 ℃, keeping the temperature for 1 hour after the materials are heated to 170 ℃, then heating to 190 ℃, keeping the temperature for 1 hour at 190 ℃, heating to 210 ℃, keeping the temperature for 2 hours at 210 ℃, and heating to 230 ℃.
When the water yield reaches 66.9g, 67.1g of monoacid is added after the temperature is reduced to 200 ℃, the temperature is continuously raised to 230 ℃, the reaction is ended when the subsequent effluent reaches 9.9g, the polyester is cooled and crushed for later use.
The preparation method of the polyester styrene-acrylic grafted toner resin comprises the following steps: 225g of dimethylbenzene and 15g of polyester are put into a 1L four-port glass reaction kettle, the temperature is raised to 140 ℃, when the stirring is free from resistance, the stirring is started, and the stirring speed is 150 rpm.
225g of styrene, 42g of n-butyl acrylate, 18g of monobutyl maleate, 0.7g of cumene hydroperoxide, 1.8g of divinylbenzene and 1.8g of dodecyl mercaptan are weighed and mixed uniformly, and then dropwise added at a constant speed for 200min, wherein the dropwise adding temperature is controlled at 140 +/-2 ℃.
After the addition, the mixture was kept at 140 ℃ for 3 hours.
After the heat preservation is finished, heating to 170 ℃ to remove the solvent xylene, removing xylene at normal pressure, starting vacuum to remove xylene when no xylene flows out basically at normal pressure, wherein the vacuum degree needs to reach-0.096 MPa, closing vacuum when no xylene flows out after vacuum devolatilization, returning to normal pressure, cooling and discharging.
And after the resin is cooled, crushing for later use.
Example 2
The preparation method of the polyester comprises the following steps: 149.1g of neopentyl glycol, 91.3g of trimethylolpropane, 235.8g of isophthalic acid, 50g of adipic acid and 5.4g of maleic anhydride are sequentially put into a 1L four-port glass reaction kettle according to the principle of first alcohol and then acid, and finally 4g of monobutyltin oxide is added.
Heating to 150 ℃, starting stirring when stirring can rotate without resistance, heating to 170 ℃ after all the materials are dissolved, heating to 170 ℃, keeping the temperature for 1 hour after the materials are heated to 170 ℃, then heating to 190 ℃, keeping the temperature for 1 hour at 190 ℃, heating to 210 ℃, keeping the temperature for 2 hours at 210 ℃, and heating to 225 and 230 ℃.
When the water yield reaches 64.7g, 140.3g of monoacid is added after the temperature is reduced to 200 ℃, the temperature is continuously raised to 230 ℃, the reaction is ended when the subsequent effluent reaches 20.7g, the polyester is cooled and crushed for later use.
The preparation method of the polyester styrene-acrylic grafted toner resin comprises the following steps: 225g of dimethylbenzene and 30g of polyester are put into a 1L four-port glass reaction kettle, the temperature is raised to 140 ℃, when the stirring is free from resistance, the stirring is started, and the stirring speed is 150 rpm.
Weighing 225g of styrene, 27g of n-butyl acrylate, 18g of monobutyl maleate, 0.7g of dicumyl peroxide, 1.8g of divinyl benzene and 1.8g of alpha-methyl styrene linear dimer, uniformly mixing, dropwise adding at a constant speed for 200min, and controlling the dropwise adding temperature at 140 +/-2 ℃.
After the addition, the mixture was kept at 140 ℃ for 3 hours.
After the heat preservation is finished, heating to 170 ℃ to remove the solvent xylene, removing xylene at normal pressure, starting vacuum to remove xylene when no xylene flows out basically at normal pressure, wherein the vacuum degree needs to reach-0.096 MPa, closing vacuum when no xylene flows out after vacuum devolatilization, returning to normal pressure, cooling and discharging.
And after the resin is cooled, crushing for later use.
Example 3:
the preparation method of the polyester comprises the following steps: 141g of neopentyl glycol, 84.75g of trimethylolpropane, 47.5g of adipic acid, 221.25g of isophthalic acid and 5.25g of maleic anhydride are sequentially put into a 1L four-port glass reaction kettle according to the principle of first alcohol and then acid, and finally 3g of monobutyltin oxide is added.
Heating to 150 ℃, starting stirring when stirring can rotate without resistance, heating to 170 ℃ after all the materials are dissolved, heating to 170 ℃, keeping the temperature for 1 hour after the materials are heated to 170 ℃, then heating to 190 ℃, keeping the temperature for 1 hour at 190 ℃, heating to 210 ℃, keeping the temperature for 2 hours at 210 ℃, and heating to 225 and 230 ℃.
When the water yield reaches 58g, 140.3g of monoacid is added after the temperature is reduced to 200 ℃, the temperature is continuously raised to 230 ℃, the reaction is ended when the subsequent effluent reaches 20.7g, the polyester is cooled and crushed for later use.
The preparation method of the polyester styrene-acrylic grafted toner resin comprises the following steps: 225g of xylene and 60g of the polyester of example 4 are introduced into a 1L four-port glass reactor, the temperature is raised to 140 ℃ and, when stirring is not resistant, stirring is started at a speed of 150 rpm.
168g of styrene, 57.6g of n-butyl acrylate, 3.6g of monobutyl maleate, 10.8g of maleic anhydride, 0.7g of ditert-butyl peroxide, 1.8g of divinylbenzene and 1.5g of alpha-methyl styrene linear dimer are weighed, uniformly mixed and dropwise added for 200min at a constant speed, and the dropwise adding temperature is controlled at 140 +/-2 ℃.
After the addition, the mixture was kept at 140 ℃ for 3 hours.
After the heat preservation is finished, heating to 170 ℃ to remove the solvent xylene, removing xylene at normal pressure, starting vacuum to remove xylene when no xylene flows out basically at normal pressure, wherein the vacuum degree needs to reach-0.096 MPa, closing vacuum when no xylene flows out after vacuum devolatilization, returning to normal pressure, cooling and discharging.
And after the resin is cooled, crushing for later use.
Table 1 table of test results of examples of the present invention
The experimental results show that the polyester and styrene-acrylic resin copolymerized graft resin used in the invention can ensure a lower softening point temperature under the condition of high glass transition temperature, thereby meeting the requirement of low-temperature rapid fixation.
Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention.
Claims (10)
1. The polyester styrene-acrylic grafted toner resin is characterized by comprising the following components in parts by weight: polyester and styrene-acrylic resin grafted with polyester;
wherein the polyester comprises: alcohol, acid and catalyst
Wherein, the styrene-acrylic resin comprises: a monomer, an initiator, a cross-linking agent, a chain transfer agent and a xylene solvent.
2. The polyester styrene acrylic grafted toner resin according to claim 1, wherein the alcohol comprises: one or more of neopentyl glycol, trimethylolpropane, dihydroxyethoxy bisphenol A and cyclohexanediol.
3. The polyester styrene acrylic grafted toner resin according to claim 1, wherein the acid comprises: adipic acid, isophthalic acid, maleic anhydride, terephthalic acid, phthalic anhydride, benzoic acid, and t-butyl benzoic acid.
4. The polyester styrene acrylic grafted toner resin according to claim 1, wherein the catalyst comprises: tetrabutyl titanate and monobutyl tin oxide or the combination of the tetrabutyl titanate and the monobutyl tin oxide.
5. The polyester styrene acrylic grafted toner resin according to claim 1, wherein the monomers comprise: one or more of styrene, n-butyl acrylate, isooctyl acrylate, methyl methacrylate, acrylic acid, maleic anhydride and monobutyl maleate.
6. The polyester styrene acrylic grafted toner resin according to claim 1, wherein the initiator comprises: cumene hydroperoxide, dicumyl peroxide and ditert-butyl peroxide.
7. The polyester styrene acrylic grafted toner resin according to claim 1, wherein the cross-linking agent comprises: divinylbenzene.
8. The polyester styrene acrylic grafted toner resin according to claim 1, wherein the chain transfer agent comprises: one or both of dodecyl mercaptan and alpha-methylstyrene linear dimer.
9. The preparation method of the polyester styrene-acrylic grafted toner resin as claimed in claims 1 to 8 is characterized in that 60-80 parts of dimethylbenzene is used as a solvent to be put into a reactor according to mass fraction, 10-20 parts of polyester is simultaneously put into the reactor, stirring is started, and the reactor is heated to 140 ℃;
then uniformly mixing 80-90 parts of monomer, 1-5 parts of initiator, 1-5 parts of cross-linking agent and 1-5 parts of chain transfer agent, and then dropwise adding the mixture into a xylene solvent at 140 ℃, wherein the dropwise adding time is 3-5 hours, the reflux state is kept, the temperature is controlled at 140 +/-2 ℃, and the temperature is kept for 3 hours after the dropwise adding is finished;
after the heat preservation is finished, heating to 170 ℃ to remove the solvent, gradually increasing the negative pressure, and when the pressure reaches-0.096 MPa and no solvent flows out, indicating that the solvent is completely removed from the reaction liquid;
discharging the residual product in the reactor, cooling and crushing to obtain the polyester styrene-acrylic grafted powdered ink resin.
10. A process for the preparation of the polyester according to claim 9, characterized in that it comprises the following steps: firstly putting corresponding alcohol and acid into a reactor according to the mol ratio of the alcohol to the acid of 1.2-1.5:1, simultaneously adding a catalyst, heating to 150 ℃, starting stirring, slowly heating to 230 ℃ at the speed of 15-20 ℃ per hour, putting monobasic acid for end capping when the water yield reaches the requirement, and finally removing water in vacuum.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210595851.XA CN114957566A (en) | 2022-05-30 | 2022-05-30 | Polyester styrene-acrylic grafted powdered ink resin and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210595851.XA CN114957566A (en) | 2022-05-30 | 2022-05-30 | Polyester styrene-acrylic grafted powdered ink resin and preparation method thereof |
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| CN114957566A true CN114957566A (en) | 2022-08-30 |
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| CN202210595851.XA Pending CN114957566A (en) | 2022-05-30 | 2022-05-30 | Polyester styrene-acrylic grafted powdered ink resin and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115521468A (en) * | 2022-09-13 | 2022-12-27 | 张家港威迪森化学有限公司 | Powdered ink resin and preparation method thereof |
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| CN107312297A (en) * | 2017-08-07 | 2017-11-03 | 天津市合成材料工业研究所有限公司 | A kind of ink powder composite resin emulsion and preparation method thereof |
| CN111399352A (en) * | 2020-05-19 | 2020-07-10 | 湖北雨田科技有限公司 | Styrene-acrylic-polyester block copolymer resin for powdered ink |
-
2022
- 2022-05-30 CN CN202210595851.XA patent/CN114957566A/en active Pending
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| CN1103965A (en) * | 1993-06-22 | 1995-06-21 | 三洋化成工业株式会社 | Charge controller, toner binder composition and electrophotographic toner |
| US5518850A (en) * | 1994-09-30 | 1996-05-21 | Xerox Corporation | Unsaturated polyesters with vinyl side chains |
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| CN115521468A (en) * | 2022-09-13 | 2022-12-27 | 张家港威迪森化学有限公司 | Powdered ink resin and preparation method thereof |
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