IP Library Granted Patent US 11,572,428
Granted Patent B2
US 11,572,428 · App. 17/147,664 · Granted Feb 7, 2023

Acrylate comb dispersing agent and preparation method and use thereof, and white ink-jet color paste and preparation method thereof

Inventors: Yun-chieh Chang (Zhuhai, CN); Guojing Wei (Zhuhai, CN); Xiangmei Tao (Zhuhai, CN)
Assignee: Zhuhai Trendvision New Materials Co., Ltd.
C08F220/18C09D17/008C08K3/22C08K2003/2241
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Quick Facts
Patent No.
US 11,572,428
App. No.
17/147,664
Granted
Feb 7, 2023
Kind
B2
Abstract

The present disclosure relates to the technical field of pigment dispersing agents, and provides an acrylate comb dispersing agent and a preparation method and use thereof, and a white ink-jet color paste and a preparation method thereof. The dispersing agent provided by the present disclosure is similar to a comb in structure and is synthesized from a hydrophobic monomer (comb handle) and a hydrophilic macromonomer (comb teeth). The acrylate comb dispersing agent provided by the present disclosure is good in dispersity, capable of stably dispersing titanium dioxide, relatively low in molecular weight and capable of meeting the requirements of ink-jet ink. The white ink-jet color paste provided by the present disclosure is strong in stability and low in viscosity, is not easy to settle and flocculate, and meets the requirements of the ink-jet ink.

Claims (38)

1. An acrylate comb dispersing agent, which is prepared from the following components in percentage by mass: 20-50% of a hydrophilic macromonomer, 30-50% of a hydrophobic monomer, 0.1-1% of a first initiator and 10-30% of a first solvent; wherein the hydrophobic monomer is a hydrophobic acrylate monomer and/or a hydrophobic olefinic monomer;

the acrylate comb dispersing agent has a molecular weight lower than 30,000;

the hydrophilic macromonomer has a molecular weight lower than 3,000;

the hydrophilic macromonomer is prepared from the following components in percentage by mass: 25-50% of a hydrophilic monomer, 0.1-1% of a second initiator, 0.1-1% of a chain transfer agent, 0.1-1% of a capping agent, and 47-74.7% of a second solvent; wherein the hydrophilic monomer is a hydrophilic acrylate monomer and/or a hydrophilic olefinic monomer;

the hydrophilic monomer and the hydrophobic monomer are not olefinic monomers at the same time.

2. The acrylate comb dispersing agent according to claim 1 , wherein the hydrophobic acrylate monomer comprises one or more of dimethylaminoethyl methacrylate, methyl methacrylate, ethoxy triethylene glycol methacrylate, isobornyl methacrylate, dimethylaminoethyl acrylate, diethylaminoethyl methacrylate, 1,6-hexanediol diacrylate, 1,4-butanediol diacrylate, and dipropylene glycol diacrylate; and the hydrophobic olefinic monomer comprises N-acryloyl morpholine and/or N-vinylpyrrolidone.

3. The acrylate comb dispersing agent according to claim 1 , wherein the structure of the hydrophilic acrylate monomer contains one or more of an amine group, an amide group, a carboxylic acid group, and a hydroxyl group.

4. The acrylate comb dispersing agent according to claim 1 , wherein the hydrophilic acrylate monomer comprises one or more of acrylic acid, methacrylic acid, hydroxyethyl methacrylate, maleic anhydride, and ethylene glycol dimethacrylate; and the hydrophilic olefinic monomer comprises acrylamide and/or N,N-dimethylacrylamide.

5. The acrylate comb dispersing agent according to claim 1 , wherein the first initiator and the second initiator independently comprise one or more of azobisisobutylimidazoline hydrochloride, azobisisoheptonitrile, azobisisobutyl amidine hydrochloride, azobisisobutyronitrile, azobisisovaleronitrile, azobiscyclohexanecarbonitrile, dimethyl azobisisobutyrate, azobiscyanovaleric acid and azoisobutyronitrile formamide;

the chain transfer agent comprises one or more of aliphatic thiol, carbon tetrachloride, dithiol ester, iodoform, 1-chloro-1-iodoalkane, 2,4-diphenyl-4-methyl-1-pentene and 3-isooctyl mercaptopropionate;

the capping agent comprises one or more of hexamethylene diisocyanate, tert-butyl peroxy-2-ethylhexanoate and methyl ethyl ketoxime;

the first solvent and the second solvent independently comprises one or more of ethanol, n-propanol, isopropanol, butanone, methyl isobutyl ketone, ethyl acetate, isopropyl acetate, dichloromethane, acetone, dichloroethane, toluene, xylene, tetrahydrofuran, and cyclohexanone.

6. A method for preparing the acrylate comb dispersing agent according to claim 1 , comprising the steps of:

(1) mixing a hydrophilic monomer, a chain transfer agent and a second solvent, and then adding a second initiator for reaction to obtain a reaction solution;

(2) mixing the reaction solution obtained in the step (1) with a capping agent for reaction to obtain a hydrophilic macromonomer; and

(3) mixing a hydrophobic monomer and a first solvent, and then adding the hydrophilic macromonomer and a first initiator for reaction to obtain the acrylate comb dispersing agent.

7. A method for preparing the acrylate comb dispersing agent according to claim 6 , wherein the hydrophobic acrylate monomer comprises one or more of dimethylaminoethyl methacrylate, methyl methacrylate, ethoxy triethylene glycol methacrylate, isobornyl methacrylate, dimethylaminoethyl acrylate, diethylaminoethyl methacrylate, 1,6-hexanediol diacrylate, 1,4-butanediol diacrylate, and dipropylene glycol diacrylate; and the hydrophobic olefinic monomer comprises N-acryloyl morpholine and/or N-vinylpyrrolidone.

8. The method for preparing the acrylate comb dispersing agent according to claim 6 , wherein the structure of the hydrophilic acrylate monomer contains one or more of an amine group, an amide group, a carboxylic acid group, and a hydroxyl group.

9. The method for preparing the acrylate comb dispersing agent according to claim 6 , wherein the hydrophilic acrylate monomer comprises one or more of acrylic acid, methacrylic acid, hydroxyethyl methacrylate, maleic anhydride, and ethylene glycol dimethacrylate; and the hydrophilic olefinic monomer comprises acrylamide and/or N,N-dimethylacrylamide.

10. The method for preparing the acrylate comb dispersing agent according to claim 6 , wherein the first initiator and the second initiator independently comprise one or more of azobisisobutylimidazoline hydrochloride, azobisisoheptonitrile, azobisisobutyl amidine hydrochloride, azobisisobutyronitrile, azobisisovaleronitrile, azobiscyclohexanecarbonitrile, dimethyl azobisisobutyrate, azobiscyanovaleric acid and azoisobutyronitrile formamide;

the chain transfer agent comprises one or more of aliphatic thiol, carbon tetrachloride, dithiol ester, iodoform, 1-chloro-1-iodoalkane, 2,4-diphenyl-4-methyl-1-pentene and 3-isooctyl mercaptopropionate;

the capping agent comprises one or more of hexamethylene diisocyanate, tert-butyl peroxy-2-ethylhexanoate and methyl ethyl ketoxime;

the first solvent and the second solvent independently comprises one or more of ethanol, n-propanol, isopropanol, butanone, methyl isobutyl ketone, ethyl acetate, isopropyl acetate, dichloromethane, acetone, dichloroethane, toluene, xylene, tetrahydrofuran, and cyclohexanone.

11. The preparation method according to claim 6 , wherein all of the temperatures of the reactions in the steps (1), (2) and (3) are 5-10° C. below the boiling point of the solvent as used.

12. The preparation method according to claim 7 , wherein all of the temperatures of the reactions in the steps (1), (2) and (3) are 5-10° C. below the boiling point of the solvent as used.

13. The preparation method according to claim 8 , wherein all of the temperatures of the reactions in the steps (1), (2) and (3) are 5-10° C. below the boiling point of the solvent as used.

14. A white ink-jet color paste comprising the following components in percentage by mass: 2-30% of the acrylate comb dispersing agent according to claim 1 , 20-60% of titanium dioxide, 1-5% of a neutralizing agent, and 5-77% of water.

15. The white ink-jet color paste comprising the following components in percentage by mass: 2-30% of the acrylate comb dispersing agent according to claim 14 , 20-60% of titanium dioxide, 1-5% of a neutralizing agent, and 5-77% of water;

wherein the hydrophobic acrylate monomer comprises one or more of dimethylaminoethyl methacrylate, methyl methacrylate, ethoxy triethylene glycol methacrylate, isobornyl methacrylate, dimethylaminoethyl acrylate, diethylaminoethyl methacrylate, 1,6-hexanediol diacrylate, 1,4-butanediol diacrylate, and dipropylene glycol diacrylate; and the hydrophobic olefinic monomer comprises N-acryloyl morpholine and/or N-vinylpyrrolidone.

16. The white ink-jet color paste comprising the following components in percentage by mass: 2-30% of the acrylate comb dispersing agent according to claim 14 , 20-60% of titanium dioxide, 1-5% of a neutralizing agent, and 5-77% of water;

wherein the structure of the hydrophilic acrylate monomer contains one or more of an amine group, an amide group, a carboxylic acid group, and a hydroxyl group.

17. The white ink-jet color paste comprising the following components in percentage by mass: 2-30% of the acrylate comb dispersing agent according to claim 14 , 20-60% of titanium dioxide, 1-5% of a neutralizing agent, and 5-77% of water;

wherein the hydrophilic acrylate monomer comprises one or more of acrylic acid, methacrylic acid, hydroxyethyl methacrylate, maleic anhydride, and ethylene glycol dimethacrylate; and the hydrophilic olefinic monomer comprises acrylamide and/or N,N-dimethylacrylamide.

18. The white ink-jet color paste comprising the following components in percentage by mass: 2-30% of the acrylate comb dispersing agent according to claim 14 , 20-60% of titanium dioxide, 1-5% of a neutralizing agent, and 5-77% of water;

wherein the first initiator and the second initiator independently comprise one or more of azobisisobutylimidazoline hydrochloride, azobisisoheptonitrile, azobisisobutyl amidine hydrochloride, azobisisobutyronitrile, azobisisovaleronitrile, azobiscyclohexanecarbonitrile, dimethyl azobisisobutyrate, azobiscyanovaleric acid and azoisobutyronitrile formamide;

the chain transfer agent comprises one or more of aliphatic thiol, carbon tetrachloride, dithiol ester, iodoform, 1-chloro-1-iodoalkane, 2,4-diphenyl-4-methyl-1-pentene and 3-isooctyl mercaptopropionate;

the capping agent comprises one or more of hexamethylene diisocyanate, tert-butyl peroxy ethylhexanoate and methyl ethyl ketoxime;

the first solvent and the second solvent independently comprises one or more of ethanol, n-propanol, isopropanol, butanone, methyl isobutyl ketone, ethyl acetate, isopropyl acetate, dichloromethane, acetone, dichloroethane, toluene, xylene, tetrahydrofuran, and cyclohexanone.

Assignments (2)
CHANGE OF NAME Recorded Sep 14, 2022
From: TRENDVISION TECHNOLOGY (ZHUHAI) CO., LTD.
To: ZHUHAI TRENDVISION NEW MATERIALS CO., LTD.
Reel/Frame 061432/0583 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 13, 2021
From: ZHANG, YUNJIE; WEI, GUOJING; TAO, XIANGMEI
To: TRENDVISION TECHNOLOGY (ZHUHAI) CO., LTD.
Reel/Frame 054903/0873 →
Priority Claims (1)
CN 202010030757.0 · Jan 13, 2020 · national
Continuity (1)
Related Publication 20210214480A1 · Jul 15, 2021