CN108070066B - Paint and ink anti-settling agent and preparation method thereof - Google Patents
Paint and ink anti-settling agent and preparation method thereof Download PDFInfo
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- CN108070066B CN108070066B CN201711484273.8A CN201711484273A CN108070066B CN 108070066 B CN108070066 B CN 108070066B CN 201711484273 A CN201711484273 A CN 201711484273A CN 108070066 B CN108070066 B CN 108070066B
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- diamine
- settling agent
- prepolymerization
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- acid
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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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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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
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
Abstract
The coating ink anti-settling agent comprises an NCO-terminated polyurethane prepolymer A and an amino-terminated copolyamide prepolymer B, wherein the molar ratio of NCO groups in the prepolymer A to amino groups in the prepolymer B is 0.5-2: 1, the prepolymer A is prepared by polymerizing a monohydroxy compound and isocyanate according to the molar ratio of 0.5-1.5: 1, the prepolymer B is prepared by polymerizing dibasic acid and diamine according to the molar ratio of 0.4-0.8: 1, and the prepolymer A and the prepolymer B are reacted to form urea during preparation. The product not only has excellent thickening and anti-settling effects, but also can endow a paint ink system with higher thixotropic property, and simultaneously can ensure the transparency of the paint.
Description
Technical Field
The invention belongs to the field of coating ink chemical industry, and particularly relates to a coating ink anti-settling agent and a preparation method thereof.
Background
The anti-settling agent is a rheological control agent of the coating, and enables the coating to have thixotropy and greatly improve the viscosity. The anti-settling agent plays an important role in modern coatings and has an important influence on the production, storage, coating and film coating performance of the coatings, so that the use of the anti-settling agent is increasingly emphasized, and novel varieties with better performance are continuously developed. Among the compounds that control the rheology of liquid coating inks are mainly organically modified bentonites, silicic acid, hydrogenated castor oil and polyamide waxes. The disadvantages of these substances are: they are generally solid and must be introduced into the system by means of a certain shear force at a certain temperature using a solvent to disperse the semifinished product formed. If the temperature of the system is once too high or too low, the resulting coating system precipitates particles, which can lead to defects in the coating. For polyamides, polyesteramides and polymers of modified bentonites and polyamides, a disadvantage of these rheology auxiliaries is that they lead to haze and haze which renders the coating opaque. Furthermore, dust from handling dried powdered products is undesirable during processing.
Disclosure of Invention
The invention aims to overcome the problems in the prior art and provide a coating ink anti-settling agent which has excellent thickening and anti-settling effects and can provide a coating ink system with higher thixotropic property and a preparation method thereof.
In order to achieve the above purpose, the invention provides the following technical scheme:
the coating ink anti-settling agent comprises an NCO-terminated polyurethane prepolymer A and an amino-terminated copolyamide prepolymer B, wherein the molar ratio of NCO groups in the A to amino groups in the B is 0.5-2: 1, the A is formed by polymerizing a monohydroxy compound and isocyanate according to the molar ratio of 0.5-1.5: 1, and the B is formed by polymerizing dibasic acid and diamine according to the molar ratio of 0.4-0.8: 1.
The structural formula of the monohydroxy compound is R1(EO) mOH, wherein R1 is methyl, ethyl, isopropyl or isoamyl, and m is a positive integer of 10-40;
the isocyanate is toluene diisocyanate, isophorone diisocyanate, hexane diisocyanate, tetramethyl xylene diisocyanate, diphenylmethane-4, 4' -diisocyanate or diphenylmethane-2, 4-diisocyanate;
the dibasic acid is one or a mixture of two of dimer acid, adipic acid, terephthalic acid, azelaic acid, succinic acid and glutaric acid;
the diamine is one or two of hexamethylene diamine, decamethylene diamine, p-phenylene diamine, m-phenylene diamine, polyethylene diamine, octamethylene diamine, nonane diamine, diethylene triamine, butane diamine, pentane diamine and 4,4 diamino xylene.
R1 is methyl, and m is 20-30.
A preparation method of a paint ink anti-settling agent sequentially comprises the following steps:
step one, preparing A and B;
and step two, reacting the prepared A and B to form urea to obtain the coating ink anti-settling agent.
The first step comprises preparation of A and preparation of B;
the preparation method of the A comprises the following steps: mixing the dried monohydroxy compound, isocyanate, a prepolymerization solvent and a prepolymerization catalyst, and then carrying out prepolymerization for 1-2 h at the temperature of 30-80 ℃;
the preparation of B is specifically as follows: mixing the dried dibasic acid and diamine with a polycondensation solvent and a polycondensation catalyst, and performing polycondensation for 1-4 h at 80-200 ℃;
the second step is as follows: mixing A and B, adding a reaction buffering agent, and carrying out prepolymerization for 1-3 h at 60-120 ℃.
In the first step of the method,
the prepolymerization solvent is a high-boiling-point solvent, and the addition mass of the prepolymerization solvent is one time of that of A;
the prepolymerization catalyst is organic tin or triethylamine, and the addition mass of the prepolymerization catalyst is 0.01-1% of the addition mass of A;
the polycondensation solvent is an aromatic hydrocarbon solvent, and the addition mass of the aromatic hydrocarbon solvent is one time of that of B;
the polycondensation catalyst is pyridine, imidazole or triphenyl phosphite, and the addition mass of the polycondensation catalyst is 0.5-1% of that of B;
in the second step, the first step is carried out,
the reaction buffering agent is lithium chloride, and the addition amount of the reaction buffering agent is 0.5-1.5% of the coating and ink anti-settling agent.
In the first step, the structural formula of the monohydroxy compound is R1(EO) mOH, wherein R1 is methyl, ethyl, isopropyl or isoamyl, and m is a positive integer of 10-40;
the isocyanate is toluene diisocyanate, isophorone diisocyanate, hexane diisocyanate, tetramethyl xylene diisocyanate, diphenylmethane-4, 4' -diisocyanate or diphenylmethane-2, 4-diisocyanate;
the dibasic acid is one or a mixture of two of dimer acid, adipic acid, terephthalic acid, azelaic acid, succinic acid and glutaric acid;
the diamine is one or two of hexamethylene diamine, decamethylene diamine, p-phenylene diamine, m-phenylene diamine, polyethylene diamine, octamethylene diamine, nonane diamine, diethylene triamine, butane diamine, pentane diamine and 4,4 diamino xylene.
R1 is methyl, and m is 20-30.
Compared with the prior art, the invention has the beneficial effects that:
1. the coating ink anti-settling agent comprises an NCO-terminated polyurethane prepolymer A and an amino-terminated copolymerized polyamide prepolymer B, wherein the A is formed by polymerizing a monohydroxy compound and isocyanate according to a molar ratio of 0.5-1.5: 1, the B is formed by polymerizing dibasic acid and diamine according to a molar ratio of 0.4-0.8: 1, and the anti-settling agent is a clear transparent liquid. Therefore, the invention not only can endow the paint and ink system with higher thixotropic property, but also has excellent thickening and anti-settling effects, and simultaneously can ensure the transparency of the paint.
2. The compatibility and the tolerance of the anti-settling agent can be adjusted by selecting different substituents in the A in the paint ink anti-settling agent, so that the A is suitable for a paint ink system with specific polarity and thixotropic anti-settling under any specific condition is realized. Thus, the present invention enables thixotropic anti-settling under any particular condition.
Detailed Description
The present invention will be further described with reference to the following embodiments.
The coating ink anti-settling agent comprises an NCO-terminated polyurethane prepolymer A and an amino-terminated copolyamide prepolymer B, wherein the molar ratio of NCO groups in the A to amino groups in the B is 0.5-2: 1, the A is formed by polymerizing a monohydroxy compound and isocyanate according to the molar ratio of 0.5-1.5: 1, and the B is formed by polymerizing dibasic acid and diamine according to the molar ratio of 0.4-0.8: 1.
The structural formula of the monohydroxy compound is R1(EO) mOH, wherein R1 is methyl, ethyl, isopropyl or isoamyl, and m is a positive integer of 10-40;
the isocyanate is toluene diisocyanate, isophorone diisocyanate, hexane diisocyanate, tetramethyl xylene diisocyanate, diphenylmethane-4, 4' -diisocyanate or diphenylmethane-2, 4-diisocyanate;
the dibasic acid is one or a mixture of two of dimer acid, adipic acid, terephthalic acid, azelaic acid, succinic acid and glutaric acid;
the diamine is one or two of hexamethylene diamine, decamethylene diamine, p-phenylene diamine, m-phenylene diamine, polyethylene diamine, octamethylene diamine, nonane diamine, diethylene triamine, butane diamine, pentane diamine and 4,4 diamino xylene.
R1 is methyl, and m is 20-30.
A preparation method of a paint ink anti-settling agent sequentially comprises the following steps:
step one, preparing A and B;
and step two, reacting the prepared A and B to form urea to obtain the coating ink anti-settling agent.
The first step comprises preparation of A and preparation of B;
the preparation method of the A comprises the following steps: mixing the dried monohydroxy compound, isocyanate, a prepolymerization solvent and a prepolymerization catalyst, and then carrying out prepolymerization for 1-2 h at the temperature of 30-80 ℃;
the preparation of B is specifically as follows: mixing the dried dibasic acid and diamine with a polycondensation solvent and a polycondensation catalyst, and performing polycondensation for 1-4 h at 80-200 ℃;
the second step is as follows: mixing A and B, adding a reaction buffering agent, and carrying out prepolymerization for 1-3 h at 60-120 ℃.
In the first step of the method,
the prepolymerization solvent is a high-boiling-point solvent, and the addition mass of the prepolymerization solvent is one time of that of A;
the prepolymerization catalyst is organic tin or triethylamine, and the addition mass of the prepolymerization catalyst is 0.01-1% of the addition mass of A;
the polycondensation solvent is an aromatic hydrocarbon solvent, and the addition mass of the aromatic hydrocarbon solvent is one time of that of B;
the polycondensation catalyst is pyridine, imidazole or triphenyl phosphite, and the addition mass of the polycondensation catalyst is 0.5-1% of that of B;
in the second step, the first step is carried out,
the reaction buffering agent is lithium chloride, and the addition amount of the reaction buffering agent is 0.5-1.5% of the coating and ink anti-settling agent.
In the first step, the structural formula of the monohydroxy compound is R1(EO) mOH, wherein R1 is methyl, ethyl, isopropyl or isoamyl, and m is a positive integer of 10-40;
the isocyanate is toluene diisocyanate, isophorone diisocyanate, hexane diisocyanate, tetramethyl xylene diisocyanate or diphenylmethane-4, 4' -diisocyanate or diphenylmethane-2, 4-diisocyanate;
the dibasic acid is one or a mixture of two of dimer acid, adipic acid, terephthalic acid, azelaic acid, succinic acid and glutaric acid;
the diamine is one or two of hexamethylene diamine, decamethylene diamine, p-phenylene diamine, m-phenylene diamine, polyethylene diamine, octamethylene diamine, nonane diamine, diethylene triamine, butane diamine, pentane diamine and 4,4 diamino xylene.
R1 is methyl, and m is 20-30.
Example 1:
the coating ink anti-settling agent comprises a polyurethane prepolymer A containing terminal NCO and a copolymerized polyamide prepolymer B containing terminal amino, wherein the molar ratio of NCO groups in the A to amino groups in the B is 2:1, the A is polymerized from a monohydroxy compound MPEG750 and isocyanate toluene diisocyanate TDI according to the molar ratio of 1:1, and the B is polymerized from a dibasic acid dimer acid and diamine polyethylene diamine according to the molar ratio of 0.55: 1.
A preparation method of a paint ink anti-settling agent sequentially comprises the following steps:
step one, drying a monohydroxy compound, isocyanate, dibasic acid and diamine at 50 ℃ for 12 hours for later use;
step two, firstly, pouring the dried monohydroxy compound and isocyanate into a three-neck flask with a stirrer, then adding a prepolymerization solvent DMF and a prepolymerization catalyst organotin into the flask, heating to 40 ℃, then dropwise adding TDI while stirring, keeping the temperature and stirring for 2 hours after dropwise adding is finished, testing the NCO content, stopping stirring when the theoretical NCO content is reached, and cooling to obtain A, wherein the addition amount of the prepolymerization solvent is one time of that of the A, and the addition amount of the prepolymerization catalyst is 0.5% of that of the A;
pouring the dried dibasic acid and diamine into a four-neck flask with a stirring and condensing device, adding a polycondensation catalyst pyridine and a polycondensation solvent xylene, replacing 5 times with nitrogen, heating to 170 ℃, testing an amine value and an acid value every half an hour, keeping the temperature for two hours when the acid value is less than 5, cooling, and testing the amine value to obtain a product B, wherein the addition amount of the polycondensation solvent is one time of that of the product B, and the addition amount of the polycondensation catalyst is 0.5% of that of the product B;
step four, pouring the prepared A and B into a three-neck flask with a stirrer, adding a reaction buffering agent lithium chloride, heating to 80 ℃, pre-polymerizing for 1h, keeping the temperature for two hours, testing the amine value, diluting to 50% solid content by using a mixed solution of xylene and n-butyl alcohol, and obtaining the paint and ink anti-settling agent which is a dark yellow clear transparent liquid, wherein the addition amount of the reaction buffering agent is 0.5% of that of the paint and ink anti-settling agent.
Example 2:
the difference from example 1 is that:
the monohydroxy compound is MPEG1150, the diamine is 3, 3 dimethyl-4, 4 diaminodiphenylmethane, and the molar ratio of the dibasic acid to the diamine is 2: 3.
In the second step, the prepolymerization temperature is 80 ℃, the prepolymerization time is 1h, the addition amount of the prepolymerization catalyst is 0.01 percent of A, the polycondensation temperature is 80 ℃, the polycondensation time is 4h, and the addition amount of the polycondensation catalyst is 1 percent of A;
in the third step, the addition amount of the reaction buffering agent is 1.5 percent of the anti-settling agent of the coating ink.
Example 3:
the difference from example 1 is that:
the monohydroxy compound is MPEG350, the isocyanate is diphenylmethane-2, 4-diisocyanate, the dibasic acid is adipic acid, the diamine is m-phenylenediamine, the molar ratio of the monohydroxy compound to the isocyanate is 0.5:1, and the molar ratio of the dibasic acid to the diamine is 0.8: 1.
In the second step, the prepolymerization temperature is 60 ℃, the prepolymerization time is 2 hours, the addition amount of the prepolymerization catalyst is 1 percent of the A, the polycondensation temperature is 200 ℃, and the polycondensation time is 2 hours;
in the third step, the addition amount of the reaction buffering agent is 1 percent of the anti-settling agent of the coating ink.
The product of the above example was now tested for sag resistance:
1. formulation 1
The test formulations were prepared by adding 1% of the product of the above examples according to formulation 1 with stirring, and then cooling to 20 ℃ and diluting with the solvent mixture. After the addition of the curing agent, the sag resistance was evaluated as follows:
| test items | Example 1 | Example 2 | Example 3 |
| Gel rear thickness (um) | 650 | 850 | 700 |
2. Formulation 2
The test formulations were prepared by adding 1% of the product of the above examples according to formulation 2 with stirring, and then cooling to 20 ℃ and diluting with the solvent mixture. After the addition of the curing agent, the sag resistance was evaluated as follows:
| test items | Example 1 | Example 2 | Example 3 |
| Gel rear thickness (um) | 900 | 800 | 800 |
Claims (5)
1. The paint ink anti-settling agent is characterized in that:
the anti-settling agent comprises a polyurethane prepolymer A containing terminal NCO and a copolyamide prepolymer B containing terminal amino, wherein the molar ratio of NCO groups in the A to amino groups in the B is 0.5-2: 1, the A is formed by polymerizing a monohydroxy compound and isocyanate according to the molar ratio of 0.5-1.5: 1, and the B is formed by polymerizing dibasic acid and diamine according to the molar ratio of 0.4-0.8: 1;
the structural formula of the monohydroxy compound is R1(EO) mOH, wherein R1 is methyl, ethyl, isopropyl or isoamyl, and m is a positive integer of 10-40;
the isocyanate is toluene diisocyanate, isophorone diisocyanate, hexane diisocyanate, tetramethyl xylene diisocyanate, diphenylmethane-4, 4 '-diisocyanate or diphenylmethane-2, 4' -diisocyanate;
the dibasic acid is one or a mixture of two of dimer acid, adipic acid, terephthalic acid, azelaic acid, succinic acid and glutaric acid;
the diamine is one or two of hexamethylene diamine, decamethylene diamine, p-phenylene diamine, m-phenylene diamine, polyethylene diamine, octamethylene diamine, nonane diamine, diethylene triamine, butane diamine, pentane diamine and 4, 4' -diamino diphenylmethane.
2. The coating ink anti-settling agent of claim 1, wherein: r1 is methyl, and m is 20-30.
3. A method for preparing the coating ink anti-settling agent of claim 1, which is characterized in that:
the method comprises the following steps in sequence:
step one, preparing A and B, wherein,
the preparation method of the A comprises the following steps: mixing the dried monohydroxy compound, isocyanate, a prepolymerization solvent and a prepolymerization catalyst, and then carrying out prepolymerization for 1-2 h at the temperature of 30-80 ℃;
the preparation of B is specifically as follows: mixing the dried dibasic acid and diamine with a polycondensation solvent and a polycondensation catalyst, and performing polycondensation for 1-4 h at 80-200 ℃;
and step two, mixing the prepared A and B, adding a reaction buffering agent, and carrying out prepolymerization for 1-3 h at 60-120 ℃ to obtain urea, thereby obtaining the coating ink anti-settling agent.
4. The method for preparing the coating ink anti-settling agent according to claim 3, wherein the method comprises the following steps:
in the first step of the method,
the prepolymerization solvent is a high-boiling-point solvent, and the addition mass of the prepolymerization solvent is one time of that of A;
the prepolymerization catalyst is organic tin or triethylamine, and the addition mass of the prepolymerization catalyst is 0.01-1% of the addition mass of A;
the polycondensation solvent is an aromatic hydrocarbon solvent, and the addition mass of the aromatic hydrocarbon solvent is one time of that of B;
the polycondensation catalyst is pyridine, imidazole or triphenyl phosphite, and the addition mass of the polycondensation catalyst is 0.5-1% of that of B;
in the second step, the first step is carried out,
the reaction buffering agent is lithium chloride, and the addition mass of the reaction buffering agent is 0.5-1.5% of that of the coating and ink anti-settling agent.
5. The method for preparing the coating ink anti-settling agent according to claim 3, wherein the method comprises the following steps: r1 is methyl, and m is 20-30.
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| CN113999390A (en) * | 2021-10-29 | 2022-02-01 | 江西省龙海化工有限公司 | Polyurea modified polyamide aqueous rheological additive and preparation method thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2822908C2 (en) * | 1978-05-26 | 1980-03-20 | Byk-Mallinckrodt Chemische Produkte Gmbh, 4230 Wesel | Thixotropic agents for coating agents |
| AT367078B (en) * | 1980-02-27 | 1982-05-25 | Vianova Kunstharz Ag | METHOD FOR THE PRODUCTION OF ADHESIVE RESIN FOR THE THIXOTROPROTECTION OF LONG-TERM ALKYD RESIN |
| AU582614B2 (en) * | 1984-12-25 | 1989-04-06 | Nippon Paint Co., Ltd. | Composition containing dispersed pigment and preparation method thereof |
| NL8500476A (en) * | 1985-02-20 | 1986-09-16 | Akzo Nv | THIXOTROPE COATING COMPOSITION. |
| DE19919482C2 (en) * | 1999-04-29 | 2001-04-26 | Byk Chemie Gmbh | Process for the preparation of a thixotropic agent and its use |
| DE10039837C2 (en) * | 2000-08-16 | 2003-03-20 | Byk Chemie Gmbh | Process for the preparation of a storage-stable, rheologically effective urea urethane solution with broad compatibility |
| DE102006010721B4 (en) * | 2006-03-08 | 2010-04-15 | Byk-Chemie Gmbh | Biuret compounds for rheology control |
| KR20160148873A (en) * | 2015-06-17 | 2016-12-27 | 민병호 | Thixotropic Agent for thinner of shipping paint |
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2017
- 2017-12-29 CN CN201711484273.8A patent/CN108070066B/en active Active
Non-Patent Citations (2)
| Title |
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| Development of Thixotropic Coatings Using Dimerized Soybean Oil Fatty Acids: The Case of Polyamide of 1,2-Phenylene Diamine;Ikechukwu D等;《Journal of Polymers and the Environment》;20100319;第18卷(第2期);第104-115页 * |
| 浅谈流变剂在高固体分环氧防腐涂料中的应用;姜显华，等;《中国涂料》;20160131;第31卷(第1期);第56-59页 * |
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Effective date of registration: 20201209 Address after: No.28, Huangjin Road, Xiaoqiao Industrial Park, Xishan Street office, Ezhou City, Hubei Province Patentee after: Ezhou Anjikang Technology Co.,Ltd. Address before: 436000, 50 meters south of Dushan Road, Ezhou Economic Development Zone, Ezhou City, Hubei Province Patentee before: Chen Peng |