CN110835398A - Preparation method of rosin-based waterborne polyurethane emulsion - Google Patents
Preparation method of rosin-based waterborne polyurethane emulsion Download PDFInfo
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4891—Polyethers modified with higher fatty oils or their acids or by resin acids
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- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
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- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
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- C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
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- 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
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- C09D175/08—Polyurethanes from polyethers
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Abstract
The invention discloses a preparation method of rosin-based waterborne polyurethane emulsion. (1) Mixing rosin, polyether glycol diglycidyl ether and a catalyst in a reaction kettle in a state of N2And reacting for 2-8 hours at 100-150 ℃ in the atmosphere, and removing the catalyst and water by reduced pressure distillation after the reaction is finished to obtain the rosin modified polyether polyol. (2) Adding rosin modified polyether glycol, solvent, diisocyanate, hydrophilic chain extender, micromolecular chain extender, crosslinking monomer and catalyst into the mixtureAnd (3) reacting for 6-10 hours in a bottle, adding a neutralizing agent, an end-capping agent and water, violently stirring and dispersing for 1 hour, and removing the solvent by reduced pressure distillation to obtain the rosin-based aqueous polyurethane emulsion which is yellowish, semitransparent and opaque to milky white. Rosin is a natural renewable resource with low price, and the synthesis of the waterborne polyurethane emulsion by using the rosin as a raw material is beneficial to reducing the cost, saving precious petroleum resources and simultaneously improving the hardness, the gloss, the water resistance and the like of a polyurethane coating.
Description
Technical Field
The invention relates to a rosin-based waterborne polyurethane emulsion and a preparation method thereof, in particular to a rosin-based waterborne polyurethane emulsion for a waterborne polyurethane coating and a preparation method thereof.
Background
The aqueous polyurethane emulsion is a polymer product which can be used for preparing paint, takes water as a solvent, has the excellent performance of the traditional polyurethane, meets the requirement of environmental protection, and is widely applied to the paint industry. Rosin-based waterborne polyurethane is modified by introducing rosin groups into polyurethane, so that the waterborne polyurethane has better hardness, gloss, water resistance and the like. At present, the modification of polyurethane by using rosin or rosin derivatives is also reported, chinese patent CN104725592A discloses a preparation method of two-component waterborne polyurethane based on maleopimaric acid, and CN101497685 utilizes rosin-based polyester polyol to prepare waterborne polyurethane. However, in the above patents, polyester polyol is prepared by using dicarboxylic acid derivatives of rosin, and aqueous polyurethane is further prepared, the triphenanthrene ring skeleton of rosin is introduced into the main chain of polyurethane, and the prepared polyurethane has too high segment rigidity and low rosin content. The rosin modified polyether glycol is used as a raw material to synthesize the waterborne polyurethane, so that rosin groups can be placed on a polymer side chain, the toughness of the polyurethane is greatly improved while other properties are basically not reduced, and the impact resistance is improved.
Disclosure of Invention
The invention aims to provide a preparation method of rosin-based waterborne polyurethane emulsion, which can be used for preparing waterborne coatings.
The method comprises the following specific steps:
(1) mixing 20-60 parts by mass of rosin, 40-80 parts by mass of polyether glycol diglycidyl ether and 0.1-1 part by mass of catalyst in a reaction kettle to enable the mixture to be in an N state2Heating to 100-150 ℃ in the atmosphere, reacting for 2-8 hours, and removing the catalyst and water by reduced pressure distillation after the reaction is finished to obtain rosin modified polyether polyol;
(2) adding 60-140 parts by mass of rosin modified polyether polyol obtained in the step (1), 50-200 parts by mass of solvent, 10-100 parts by mass of diisocyanate, 1-20 parts by mass of hydrophilic chain extender, 1-20 parts by mass of micromolecular chain extender, 0.5-20 parts by mass of crosslinking monomer and 0.1-5 parts by mass of catalyst into a flask, reacting for 6-10 hours, adding 1-20 parts by mass of neutralizer, 1-10 parts by mass of end capping agent and 100-400 parts by mass of water, violently stirring and dispersing for 1 hour, and removing the solvent by reduced pressure distillation to obtain pale yellow, semitransparent to milky opaque rosin-based aqueous polyurethane emulsion;
the polyisocyanate is one or more of 2, 4-toluene diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, xylylene diisocyanate and pentamethylene diisocyanate.
The hydrophilic chain extender is one or more of 2, 2-hydroxymethyl propionic acid, 2-hydroxymethyl butyric acid, 1, 2-propylene glycol-3-sodium sulfonate, 1, 4-butanediol-2-sodium sulfonate, N-methyldiethanolamine, benzyldimethyl (2-hydroxyethyl) ammonium chloride, dodecyl dimethyl (2-hydroxyethyl) ammonium bromide and polyoxyethylene glycol.
The cross-linking agent is one or 2 of trimethylolpropane and pentaerythritol.
The neutralizing agent is one of sodium hydroxide, potassium hydroxide, sodium bicarbonate, ammonia water, AMP-95, triethylamine, diethanolamine, triethanolamine, sodium acetate, sodium pyrophosphate, hydrochloric acid, phosphoric acid and acetic acid.
The solvent is as follows: is one or a mixture of acetone, butanone, methyl ethyl ketone and tetrahydrofuran;
the catalyst in the step (2) is one or more of dibutyltin dilaurate, stannous octoate, butylstannoic acid, zinc isooctanoate, zirconium isooctanoate and triethylamine.
The end capping agent is one or more of trihydroxymethyl aminomethane, diethanolamine and 2-hydroxyethylamine.
The rosin modified polyether polyol has the following structural characteristics:
wherein: r is polyoxyethylene ether or polyoxypropylene ether with the number average molecular weight of 200-10000.
The polyether glycol diglycidyl ether is one or more of polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polytetrahydrofuran glycol diglycidyl ether, polydiethylene glycol diglycidyl ether and polyether glycol diglycidyl ether;
the catalyst in the step (1) is one or more of triethylamine, triethylene diamine, dimethyl pyridine, N-methyl morpholine and N, N-dimethyl cyclohexylamine;
the raw materials are all industrial grade.
The prepared rosin-based waterborne polyurethane emulsion can be applied to the preparation of waterborne coatings.
The invention has the following technical characteristics:
(1) the rosin modified polyether glycol is used as a soft segment of the waterborne polyurethane, so that the polymer emulsion has better excellent performances such as hardness, gloss and water resistance.
(2) The rosin group is positioned on the side chain of the polyurethane, and the obtained polymer emulsion has better toughness than other rosin modified polyurethanes, and is more suitable for being used in paint.
(3) The rosin-based waterborne polyurethane disclosed by the invention can be used for a single-component polyurethane coating and can also be used for a double-component polyurethane coating according to different molecular weights designed during synthesis.
(4) Rosin is a natural renewable resource with low cost, and compared with the traditional product, the rosin-based waterborne polyurethane has the advantages of environmental protection and low cost.
Detailed Description
All the raw materials are technical grade.
Example 1:
(1) adding 45 parts by mass of rosin, 55 parts by mass of polypropylene glycol diglycidyl ether with the average molecular weight of 400 and 0.5 part by mass of lutidine into a reaction kettle at one time, and adding N2Replacing the air in the kettle, then heating to 130 ℃, keeping the temperature for reaction for 4 hours, and stopping the reaction. Distilling at 110 deg.C/10 mmHg under reduced pressure for 2 hr to removeCatalyst and water to obtain the rosin modified polyether polyol. The product is brown yellow viscous liquid, the hydroxyl value is 109mgKOH/g, and the acid value is 2.7 mgKOH/g.
(2) Adding 75 parts by mass of rosin modified polyether polyol obtained in the step (1), 120 parts by mass of solvent acetone, 57 parts by mass of hexamethylene diisocyanate, 10 parts by mass of dimethylolpropionic acid, 5 parts by mass of butanediol, 1 part by mass of trimethylolpropane and 0.12 part by mass of catalyst dibutyltin dilaurate into a flask, reacting for 8 hours, adding 7.5 parts by mass of neutralizing agent triethylamine, 4 parts by mass of end-capping agent trimethylolpropane and 258 parts by mass of water, violently stirring and dispersing for 1 hour, and removing the solvent by reduced pressure distillation to obtain the pale yellow semitransparent to opalescent rosin-based waterborne polyurethane emulsion.
Example 2:
(1) same as example 1, step (1).
(2) Adding 60 parts by mass of rosin modified polyether polyol obtained in the step (1), 90 parts by mass of solvent acetone, 45 parts by mass of toluene diisocyanate, 8.4 parts by mass of hydrophilic chain extender dimethylolpropionic acid, 2.4 parts by mass of micromolecular chain extender butanediol, 1 part by mass of crosslinking monomer pentaerythritol and 0.18 part by mass of catalyst dibutyltin dilaurate into a flask, reacting for 6 hours, adding 6 parts by mass of neutralizing agent triethylamine, 1.2 parts by mass of end capping agent diethanolamine and 124 parts by mass of water, violently stirring and dispersing for 16 hours, and removing the solvent by reduced pressure distillation to obtain the pale yellow, semitransparent to milky opaque rosin-based waterborne polyurethane emulsion.
Example 3:
(1) same as example 1, step (1).
(2) Adding 60 parts by mass of rosin modified polyether polyol obtained in the step (1), 120 parts by mass of solvent acetone, 45 parts by mass of isophorone diisocyanate, 8 parts by mass of hydrophilic chain extender dimethylolpropionic acid, 8 parts by mass of small molecular chain extender, 1 part by mass of crosslinking monomer trimethylolpropane and 0.1 part by mass of catalyst dibutyltin dilaurate into a flask, reacting for 6 hours, adding 6 parts by mass of neutralizing agent triethylamine, 4 parts by mass of end capping agent 2-hydroxyethylamine and 258 parts by mass of water, violently stirring and dispersing for 1 hour, and removing the solvent by reduced pressure distillation to obtain the pale yellow, semitransparent to milky opaque rosin-based waterborne polyurethane emulsion.
Application example:
the rosin-based aqueous polyurethane emulsion obtained in example 1 and a Kostew Polymer company XP2655 are painted according to the NCO/OH ratio of 1.4, the pendulum hardness of the obtained paint film is 0.65, the adhesion force is 1 grade, the gloss is 144, the flexibility is 1mm, the impact strength (positive impact/recoil) is 50/50kg.cm, the water resistance is 72 hours, no rust exists, and the comparison sample is 48 hours, no rust exists.
Claims (2)
1. A preparation method of rosin-based waterborne polyurethane emulsion is characterized by comprising the following specific steps:
(1) mixing 20-60 parts by mass of rosin, 40-80 parts by mass of polyether glycol diglycidyl ether and 0.1-1 part by mass of catalyst in a reaction kettle to enable the mixture to be in an N state2Heating to 100-150 ℃ in the atmosphere, reacting for 2-8 hours, and removing the catalyst and water by reduced pressure distillation after the reaction is finished to obtain rosin modified polyether polyol;
(2) adding 60-140 parts by mass of rosin modified polyether polyol obtained in the step (1), 50-200 parts by mass of solvent, 10-100 parts by mass of diisocyanate, 1-20 parts by mass of hydrophilic chain extender, 1-20 parts by mass of micromolecular chain extender, 0.5-20 parts by mass of crosslinking monomer and 0.1-5 parts by mass of catalyst into a flask, reacting for 6-10 hours, adding 1-20 parts by mass of neutralizer, 1-10 parts by mass of end capping agent and 100-400 parts by mass of water, violently stirring and dispersing for 1 hour, and removing the solvent by reduced pressure distillation to obtain pale yellow, semitransparent to milky opaque rosin-based aqueous polyurethane emulsion;
the polyisocyanate is one or more of 2, 4-toluene diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, xylylene diisocyanate and pentamethylene diisocyanate;
the hydrophilic chain extender is one or more of 2, 2-hydroxymethyl propionic acid, 2-hydroxymethyl butyric acid, 1, 2-propanediol-3-sodium sulfonate, 1, 4-butanediol-2-sodium sulfonate, N-methyldiethanolamine, benzyldimethyl (2-hydroxyethyl) ammonium chloride, dodecyl dimethyl (2-hydroxyethyl) ammonium bromide and polyoxyethylene glycol;
the cross-linking agent is one or 2 of trimethylolpropane and pentaerythritol;
the neutralizing agent is one of sodium hydroxide, potassium hydroxide, sodium bicarbonate, ammonia water, AMP-95, triethylamine, diethanolamine, triethanolamine, sodium acetate, sodium pyrophosphate, hydrochloric acid, phosphoric acid and acetic acid;
the solvent is as follows: is one or a mixture of acetone, butanone, methyl ethyl ketone and tetrahydrofuran;
the catalyst in the step (2) is one or more of dibutyltin dilaurate, stannous octoate, butylstannoic acid, zinc isooctanoate, zirconium isooctanoate and triethylamine;
the end capping agent is one or more of trihydroxymethyl aminomethane, diethanolamine and 2-hydroxyethylamine;
the rosin modified polyether polyol has the structural characteristic general formula as follows:
wherein: r is polyoxyethylene ether or polyoxypropylene ether, and the number average molecular weight of the polyoxyethylene ether or polyoxypropylene ether is 200-10000;
the polyether glycol diglycidyl ether is one or more of polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, polytetrahydrofuran glycol diglycidyl ether, polydiethylene glycol diglycidyl ether and polyether glycol diglycidyl ether;
the catalyst in the step (1) is one or more of triethylamine, triethylene diamine, dimethyl pyridine, N-methyl morpholine and N, N-dimethyl cyclohexylamine;
the raw materials are all industrial grade.
2. The rosin-based aqueous polyurethane emulsion according to claim 1, wherein the rosin-based aqueous polyurethane emulsion is applicable to the preparation of an aqueous coating.
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| CN201911074508.5A CN110835398A (en) | 2019-11-06 | 2019-11-06 | Preparation method of rosin-based waterborne polyurethane emulsion |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111171272A (en) * | 2020-03-12 | 2020-05-19 | 山东天庆科技发展有限公司 | Novel composite ion solvent-free waterborne polyurethane and preparation method thereof |
| CN111607056A (en) * | 2020-05-27 | 2020-09-01 | 英德市国彩精细化工有限公司 | High-hardness quick-drying hydroxyl polyurethane dispersion composition and preparation method thereof |
| CN112760021A (en) * | 2020-12-31 | 2021-05-07 | 湖州白洋装饰材料有限公司 | Water-based decorative coating and preparation method thereof |
| CN113105850A (en) * | 2021-03-12 | 2021-07-13 | 华南理工大学 | Waterborne polyurethane-acrylate-epoxidized soybean oil label adhesive and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6258310B1 (en) * | 1999-03-18 | 2001-07-10 | Basf Corporation | Cross-linking thermoplastic polyurethane |
| CN101497685A (en) * | 2009-02-23 | 2009-08-05 | 中国林业科学研究院林产化学工业研究所 | Production of rosin based aqueous polyurethanes |
| CN107099015A (en) * | 2017-03-24 | 2017-08-29 | 广东科茂林产化工股份有限公司 | A kind of modified aqueous polyurethane dispersoid and preparation method thereof |
-
2019
- 2019-11-06 CN CN201911074508.5A patent/CN110835398A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6258310B1 (en) * | 1999-03-18 | 2001-07-10 | Basf Corporation | Cross-linking thermoplastic polyurethane |
| CN101497685A (en) * | 2009-02-23 | 2009-08-05 | 中国林业科学研究院林产化学工业研究所 | Production of rosin based aqueous polyurethanes |
| CN107099015A (en) * | 2017-03-24 | 2017-08-29 | 广东科茂林产化工股份有限公司 | A kind of modified aqueous polyurethane dispersoid and preparation method thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111171272A (en) * | 2020-03-12 | 2020-05-19 | 山东天庆科技发展有限公司 | Novel composite ion solvent-free waterborne polyurethane and preparation method thereof |
| CN111607056A (en) * | 2020-05-27 | 2020-09-01 | 英德市国彩精细化工有限公司 | High-hardness quick-drying hydroxyl polyurethane dispersion composition and preparation method thereof |
| CN112760021A (en) * | 2020-12-31 | 2021-05-07 | 湖州白洋装饰材料有限公司 | Water-based decorative coating and preparation method thereof |
| CN113105850A (en) * | 2021-03-12 | 2021-07-13 | 华南理工大学 | Waterborne polyurethane-acrylate-epoxidized soybean oil label adhesive and preparation method thereof |
| CN113105850B (en) * | 2021-03-12 | 2022-07-12 | 华南理工大学 | Waterborne polyurethane-acrylate-epoxidized soybean oil label adhesive and preparation method thereof |
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Application publication date: 20200225 |