CN112011236A - Polyether-based phosphate ester surfactant and application thereof in water-based coating composition - Google Patents
Polyether-based phosphate ester surfactant and application thereof in water-based coating composition Download PDFInfo
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- CN112011236A CN112011236A CN202010850862.9A CN202010850862A CN112011236A CN 112011236 A CN112011236 A CN 112011236A CN 202010850862 A CN202010850862 A CN 202010850862A CN 112011236 A CN112011236 A CN 112011236A
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- aqueous
- methacrylate
- acrylate
- coating composition
- aqueous coating
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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
- 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
-
- 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
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/064—Copolymers with monomers not covered by C09D133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1687—Use of special additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2237—Oxides; Hydroxides of metals of titanium
- C08K2003/2241—Titanium dioxide
Abstract
The present invention relates to an aqueous coating composition comprising an aqueous polymer dispersion and a surfactant having the structure O = P- [ O- (RO)n‑H]3Mass ratio of aqueous resin to surfactantIs 100 (1-10). By adding polyether phosphate containing alkoxy chain segment as surfactant into water paint, the use of volatile organic compound is greatly reduced, the film opening time of water paint is increased, and the antifreezing property of water paint and the antifouling property of paint film are improved.
Description
Technical Field
The invention belongs to the field of surfactants and water-based coatings, and particularly relates to a polyether-based phosphate ester surfactant containing an alkoxy chain segment and application thereof in a water-based coating composition.
Background
In aqueous coating compositions, Volatile Organic Compounds (VOC) are often added in amounts to improve the corresponding properties of the aqueous coating. Among the most commonly used volatile organic compounds are ethylene glycol, methanol, formaldehyde, toluene, chlorobenzene, and the like. Most of these volatile organic compounds are hazardous and pose serious environmental problems. In recent years, with the awareness of environmental protection and the continuous deepening of related work, aqueous coating compositions with low voc are more popular and appreciated than those with more voc added, and a voc content of less than 5g per liter of aqueous coating composition or less has become a potential requirement in the environmental protection aqueous coating industry. Therefore, much research has been devoted to eliminating various volatile organic compounds from aqueous coatings without affecting the performance of the aqueous coatings.
However, there is still no good solution, and for this reason, the inventors of the present invention found through extensive experimental studies that a polyether-based phosphate containing an alkoxy segment can replace a volatile organic compound in an aqueous coating material, and increase the open time of the aqueous coating material, and improve the freezing resistance of the aqueous coating material and the stain resistance of a coating film.
Disclosure of Invention
In order to solve the problems of high content of volatile organic compounds or low content of volatile organic compounds but poor coating performance in the existing water-based coating, the invention aims to provide a polyether-based phosphate surfactant containing alkoxy segments and application thereof in a water-based coating composition. In the invention, polyether phosphate containing alkoxy chain segment is added into the water paint as a surfactant, so that the use of volatile organic compounds can be greatly reduced, the film opening time of the water paint is increased, and the freezing resistance of the water paint and the anti-fouling performance of a paint film are improved.
The concrete solution of the invention is as follows:
an aqueous coating composition comprising an aqueous polymer dispersion and a surfactant, characterized in that: the structure of the surfactant is shown as a formula (1), and the mass ratio of the water-based resin to the surfactant is 100 (1-10);
O=P-[ O-(RO)n-H]3 （1）
wherein R is selected from C2-C4N represents a polymerization degree and is an integer of 60 to 120.
Further, in the polyether-based phosphate ester having an alkoxy segment represented by formula (1), H at the end of three branches may be replaced with a sulfonic acid group, a sulfonate group, a benzenesulfonic acid group or a benzenesulfonate group.
Further, the sulfonate or benzenesulfonate is selected from alkali metal salts and ammonium salts.
Wherein, the aqueous polymer dispersion can be aqueous resin, and the aqueous resin is selected from aqueous acrylic resin, aqueous polyurethane resin and aqueous epoxy resin.
Further, the aqueous polymer dispersion may also be a product obtained by polymerizing 50 to 70wt% of alkyl acrylate or alkyl methacrylate and 20 to 40wt% of a mixture of vinyl-containing aromatic derivatives with 1 to 10wt% of unsaturated polycarboxylic acid.
Among them, as the alkyl acrylate, methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, n-hexyl acrylate, n-octyl acrylate can be cited.
Among them, as the alkyl methacrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, n-hexyl methacrylate, and n-octyl methacrylate are cited.
Among these, as the vinyl group-containing aromatic derivatives, styrene, 2-methylstyrene, 2-n-butylstyrene, 4-methylstyrene, and 4-n-butylstyrene can be cited.
Among them, as the unsaturated polycarboxylic acids, acrylic acid, methacrylic acid, crotonic acid, and 2-ethylacrylic acid are exemplified.
Further, the water-based paint composition also comprises one or more pigments, wherein the content of the pigment is 1-10wt%, and the pigment is selected from titanium dioxide, silicon dioxide, calcium carbonate, aluminum oxide and zinc oxide.
In the invention, polyether phosphate containing alkoxy chain segment is added into the water paint as a surfactant, so that the use of volatile organic compounds can be greatly reduced, the film opening time of the water paint is increased, and the freezing resistance of the water paint and the anti-fouling performance of a paint film are improved.
Detailed Description
The following are some, but not all, specific embodiments of the invention.
Example 1
Commercially available aqueous acrylic resins, aqueous urethane resins, and aqueous epoxy resins were mixed to prepare aqueous polymer dispersions, and the aqueous polymer dispersions were mixed with a surfactant represented by formula (1) to prepare aqueous coating compositions, which are labeled as example 1-A, example 1-B, and example 1-C, respectively. In each embodiment, the mass ratio of the aqueous resin to the surfactant is 100: 5.
O=P-[ O-(RO)n-H]3 （1）
in the formula (1), R is C2N is 80.
First, the VOC content of the aqueous coating compositions obtained in the respective examples was tested, and the test method was carried out according to the relevant requirements in GB 18582-.
Secondly, for the testing of the open time of the aqueous coating compositions, reference is made to the relevant method used by basf european company in WO2014/058864, the results of which are shown in the subsequent table.
Finally, for the freezing resistance test of the aqueous coating composition, firstly, referring to the ASTM D562-2001 standard, the KU value thereof is tested by a Brookfield viscometer, then the three aqueous coating compositions obtained are respectively subjected to heat preservation at-5 ℃ for 5 hours, then are melted at 25 ℃ and the freezing and melting process is repeated three times. Then, the KU value of the aqueous coating composition was measured again, the difference between the KU values obtained by the two measurements was calculated,
if the ratio is less than 15, the product is qualified, and the other product is unqualified.
In addition, for comparison, a comparative example 1 was provided, in which comparative example 1 the surfactant used in the present invention was not added, as compared to example 1.
Table 1 results of the relevant performance tests for example 1
| VOC content | Time of opening film |  | |
| Example 1-A | Less than 2g/L | 11min | 5.5 |
| Example 1-B | Less than 2g/L | 11min | 5.2 |
| Example 1C | Less than 2g/L | 11min | 5.1 |
| Comparative example 1 | Less than 2g/L | 3min | 19 |
Example 2
An aqueous coating composition comprises an aqueous polymer dispersion, a surfactant and a pigment, wherein the structure of the surfactant is shown as the formula (1):
O=P-[ O-(RO)n-H]3 （1）
wherein R is C3N is 100; the mass ratio of the water-based resin, the surfactant and the pigment is 100:5:5。
Wherein the pigment is titanium dioxide.
Wherein the aqueous polymer dispersion is a product obtained by polymerizing 60wt% of alkyl acrylate or alkyl methacrylate and 30wt% of a mixture of vinyl-containing aromatic derivatives with 10wt% of unsaturated polycarboxylic acid.
Three examples were provided, denoted as example 2-A, example 2-B, and example 2-C, respectively. In example 2-A, the aqueous polymer dispersion was the product of the polymerization of a mixture of 60% by weight of methyl acrylate and 30% by weight of styrene with 10% by weight of methacrylic acid. In example 2-B, the aqueous polymer dispersion was the product of the polymerization of a mixture of 60wt% ethyl methacrylate and 30wt% 2-methylstyrene with 10wt% acrylic acid.
In example 2-C, the aqueous polymer dispersion was the product of the polymerization of 60% by weight of a mixture of isopropyl methacrylate and 30% by weight of 2-n-butylstyrene with 10% by weight of crotonic acid.
In example 2, a stain resistance test of the coating film was performed in addition to the VOC content test, the open time test, and the freezing resistance test of the aqueous coating composition in reference example 1.
For the stain resistance test of the coating film, referring to the relevant requirements of GB/T9780-2013, the water-based coating composition is coated on a substrate and dried and cured. And then, carrying out contamination treatment on the coating film for 10min by using gauze soaked with pollutants, wherein the pollutants comprise three kinds of pollutants, namely vinegar, ink and oil stain. The paint film was then subjected to scrubbing and water rinsing, dried, and tested for reflectance indices Y1, Y2 before and after staining, and the ratio of Y1/Y2 was calculated, the higher the ratio the better.
In addition, for comparison, a comparative example 2 was provided, and in the comparative example 2, the surfactant used in the present invention was not added, compared to the example 2.
Table 2 results of the relevant performance tests of example 2
| VOC content | Time of opening film |  | Y1/Y2 of vinegar | Y1/Y2 of ink | Greasy Y1/Y2 | |
| Example 1-A | Less than 2g/L | 11min | 5.6 | 0.95 | 0.84 | 0.98 |
| Example 1-B | Less than 2g/L | 11min | 5.3 | 0.94 | 0.83 | 0.98 |
| Example 1C | Less than 2g/L | 11min | 5.5 | 0.94 | 0.81 | 0.98 |
| Comparative example 1 | Less than 2g/L | 3min | 20 | 0.83 | 0.72 | 0.86 |
It can be found that in examples 1 and 2, the performance tests of the water-based paint composition and the coating film thereof prepared by the invention show that the water-based paint composition can not only greatly reduce the use of volatile organic compounds, but also increase the film opening time of the water-based paint and improve the freezing resistance of the water-based paint and the stain resistance of the paint film.
Claims (7)
1. An aqueous coating composition comprising an aqueous polymer dispersion and a surfactant, characterized in that: the structure of the surfactant is shown as a formula (1), and the mass ratio of the water-based resin to the surfactant is 100 (1-10);
O=P-[ O-(RO)n-H]3 （1）
wherein R is selected from C2-C4N represents a polymerization degree and is an integer of 60 to 120.
2. An aqueous coating composition according to claim 1, wherein: in the polyether-based phosphate ester containing an alkoxy segment shown in the formula (1), H at the tail ends of three branches is replaced by a sulfonic acid group, a sulfonate group, a benzene sulfonic acid group or a benzene sulfonate group.
3. An aqueous coating composition according to claim 2, wherein: the sulfonate or benzenesulfonate is selected from alkali metal salts and ammonium salts.
4. An aqueous coating composition according to claim 1, wherein: the aqueous polymer dispersion may be an aqueous resin selected from the group consisting of aqueous acrylic resins, aqueous polyurethane resins, aqueous epoxy resins.
5. An aqueous coating composition according to claim 1, wherein: the aqueous polymer dispersion may also be a product obtained by polymerizing 50 to 70% by weight of an alkyl acrylate or methacrylate and 20 to 40% by weight of a mixture of vinyl-containing aromatic derivatives with 1 to 10% by weight of an unsaturated polycarboxylic acid.
6. An aqueous coating composition according to claim 5, wherein: the alkyl acrylate is selected from one or more of methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, n-hexyl acrylate or n-octyl acrylate; the alkyl methacrylate is selected from one or more of methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, n-hexyl methacrylate or n-octyl methacrylate; the aromatic derivative containing vinyl is selected from one or more of styrene, 2-methylstyrene, 2-n-butylstyrene, 4-methylstyrene or 4-n-butylstyrene; the unsaturated polycarboxylic acid is selected from one or more of acrylic acid, methacrylic acid, crotonic acid and 2-ethyl acrylic acid.
7. An aqueous coating composition according to claim 1, wherein: the water-based paint composition also comprises one or more pigments, wherein the content of the pigment is 1-10wt%, and the pigment is selected from titanium dioxide, silicon dioxide, calcium carbonate, aluminum oxide and zinc oxide.
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| CN202010850862.9A CN112011236A (en) | 2020-08-21 | 2020-08-21 | Polyether-based phosphate ester surfactant and application thereof in water-based coating composition |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4244988A (en) * | 1976-04-14 | 1981-01-13 | Ciba-Geigy Ag | Method of coating linear polyester with aqueous latex |
| CN1433268A (en) * | 1999-12-28 | 2003-07-30 | 阿温提斯作物科学有限公司 | Tenside/solvent systems |
| CN1934290A (en) * | 2004-03-23 | 2007-03-21 | 约翰逊迪瓦西公司 | Cleaning and corrosion inhibition system and composition for surfaces of aluminum or colored metals and alloys thereof under alkaline conditions |
| CN101263205A (en) * | 2005-09-12 | 2008-09-10 | 巴斯夫欧洲公司 | Method to increase resistance against stain penetration of aqueous coating compositions |
| CN104704064A (en) * | 2012-10-11 | 2015-06-10 | 巴斯夫欧洲公司 | Surfactants for aqueous based coatings |
| WO2016037292A1 (en) * | 2014-09-08 | 2016-03-17 | Nanograde Ag | Solution-processable hri optical films comprising titanate nanoparticles |
| CN107250300A (en) * | 2014-12-22 | 2017-10-13 | 陶氏环球技术有限责任公司 | The aqueous emulsion paint of decontamination and anti-clogging characteristic with improvement |
-
2020
- 2020-08-21 CN CN202010850862.9A patent/CN112011236A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4244988A (en) * | 1976-04-14 | 1981-01-13 | Ciba-Geigy Ag | Method of coating linear polyester with aqueous latex |
| CN1433268A (en) * | 1999-12-28 | 2003-07-30 | 阿温提斯作物科学有限公司 | Tenside/solvent systems |
| CN1934290A (en) * | 2004-03-23 | 2007-03-21 | 约翰逊迪瓦西公司 | Cleaning and corrosion inhibition system and composition for surfaces of aluminum or colored metals and alloys thereof under alkaline conditions |
| CN101263205A (en) * | 2005-09-12 | 2008-09-10 | 巴斯夫欧洲公司 | Method to increase resistance against stain penetration of aqueous coating compositions |
| CN104704064A (en) * | 2012-10-11 | 2015-06-10 | 巴斯夫欧洲公司 | Surfactants for aqueous based coatings |
| WO2016037292A1 (en) * | 2014-09-08 | 2016-03-17 | Nanograde Ag | Solution-processable hri optical films comprising titanate nanoparticles |
| CN107250300A (en) * | 2014-12-22 | 2017-10-13 | 陶氏环球技术有限责任公司 | The aqueous emulsion paint of decontamination and anti-clogging characteristic with improvement |
Non-Patent Citations (1)
| Title |
|---|
| 金谷: "《表面活性剂化学》", 31 August 2013, 中国科学技术大学出版社 * |
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