CN110818872A - Preparation of low-surface-energy waterborne polyurethane and application of low-surface-energy waterborne polyurethane in printing ink - Google Patents
Preparation of low-surface-energy waterborne polyurethane and application of low-surface-energy waterborne polyurethane in printing ink Download PDFInfo
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- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- 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
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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
- C08G18/28—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
- C08G18/3203—Polyhydroxy compounds
- C08G18/3221—Polyhydroxy compounds hydroxylated esters of carboxylic acids other than higher fatty acids
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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
- C08G18/28—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
- C08G18/4825—Polyethers containing two hydroxy groups
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- 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
- C08G18/28—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
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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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
- C08G18/28—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
- C08G18/61—Polysiloxanes
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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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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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
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
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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
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
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Abstract
The invention discloses preparation of low-surface-energy waterborne polyurethane and application thereof in printing ink, and relates to the technical field of preparation and application of waterborne polyurethane. The preparation of the waterborne polyurethane comprises the steps of utilizing hydroxyethyl acrylate to seal the end of the polyurethane, introducing a carbon-carbon double bond functional group, and introducing an organosilicon group and an octadecane long-alkane side chain into the main chain of the polyurethane; the application of the preparation of the waterborne polyurethane on the ink comprises the step of compounding the waterborne polyurethane acrylate prepolymer, the acrylate monomer, the photoinitiator, the pigment, the solvent and the auxiliary agent to prepare the waterborne UV ink with low surface energy. Polysiloxane and glyceryl monostearate are introduced during synthesis of the polyurethane acrylate resin, the surface energy of silicon-carbon groups in the polysiloxane is low, and the polysiloxane can migrate towards a membrane/air interface in a film drying process to form a film and then migrate towards the surface of the membrane, so that the surface energy of the resin is reduced, and the hydrophobic and oleophobic properties of the coating are improved.
Description
Technical Field
The invention belongs to the technical field of preparation and application of waterborne polyurethane, and particularly relates to preparation of low-surface-energy waterborne polyurethane and application of the low-surface-energy waterborne polyurethane in printing ink.
Background
The environment-friendly ink mainly comprises water-based ink, water-based UV ink, alcohol-soluble ink and the like, wherein the water-based ink is the most environment-friendly ink generally recognized, has no volatile organic solvent, and is widely applied to the fields of food and drug packaging and the like. The main component of the water-based ink is the binder, and the quality of the binder of the water-based ink directly influences the quality and performance of the water-based ink. The water-based ink vehicle is mainly composed of water-based polyester resin, water-based acrylate resin, water-based polyurethane acrylic resin and the like, wherein the water-based polyurethane acrylic resin has the unique advantage of adjustable proportion of soft segments and hard segments of the polyurethane resin and the advantage of the acrylic resin, and the water-based polyurethane acrylic resin is endowed with various properties and becomes an important vehicle in the water-based ink industry.
The hydrophilic group is introduced in the preparation process of the aqueous polyurethane acrylate connecting material, so that the surface energy of the aqueous polyurethane acrylate connecting material after being coated and formed into a film reaches 40mJ/m2And is not favorable for the application of the ink in industry and life. Polysiloxane and glyceryl monostearate are introduced into the preparation of the waterborne polyurethane acrylate, so that the surface energy of an ink coating can be reduced, the purposes of hydrophobicity and oleophobicity are achieved, and the adhesive force of the ink to a nonpolar substrate is also improved.
Disclosure of Invention
The invention aims to provide preparation of low-surface-energy waterborne polyurethane and application of the low-surface-energy waterborne polyurethane in printing ink, so that the hydrophobic and oleophobic properties of the prepared printing ink and the adhesive force of the printing ink to a nonpolar substrate are enhanced.
In order to solve the technical problems, the invention is realized by the following technical scheme:
the invention relates to a preparation method of low-surface-energy waterborne polyurethane, which comprises the following steps: end capping is carried out on polyurethane by utilizing hydroxyethyl acrylate, and a carbon-carbon double bond functional group is introduced; introducing organosilicon group and one octadecane long alkane side chain into the main chain of polyurethane.
Further, the method specifically comprises the following steps:
s01, under the protection of nitrogen, adding polyester or polyether polyol, diisocyanate, polysiloxane and glyceryl monostearate into a reactor, and reacting at the temperature of 75-90 ℃ for 2-4h to obtain a solution A;
s02, adding a hydrophilic chain extender and a micromolecular dihydric alcohol chain extender into the solution A, and reacting for 1-2 hours at the temperature of 70-80 ℃ to obtain a solution B;
s03, adding a catalyst into the solution B, and reacting for 2-4h at the temperature of 60-75 ℃ until-NCO reaches a theoretical value to obtain a solution C;
s04, adding hydroxyethyl acrylate into the solution C, and reacting at the temperature of 60-70 ℃ for 1-2h to obtain a solution D;
s05, cooling the solution D to below 50 ℃, adding triethylamine for neutralization, and then adding deionized water for emulsification to obtain the low-surface-energy waterborne polyurethane acrylate.
Further, the molar ratio of the used amount of the diisocyanate to the sum of the used amounts of the polyester or polyether diol and the polysiloxane is 2 to 7.
Further, the mass percentage of the catalyst in the total mass of the polyester or polyether polyol, the diisocyanate, the polysiloxane and the glyceryl monostearate is 0.0004-0.002%.
Further, the polyester or polyether polyol is one or a mixture of more of polyoxyethylene glycol, polyoxypropylene glycol, poly adipic acid-1, 4-butanediol ester glycol, polytetrahydrofuran ether glycol, hydroxyl-terminated polybutadiene, polycaprolactone diol and polycarbonate diol.
Further, the diisocyanate is one or a mixture of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate and hexamethylene diisocyanate.
Further, the polysiloxane is hydroxyl-terminated polydimethylsiloxane with the molecular weight of 600-4000.
Further, the catalyst is one or a mixture of stannous octoate, dibutyltin dilaurate, triethanolamine and triethylene diamine.
Further, the hydrophilic chain extender is one or a mixture of dimethylolpropionic acid and dimethylolbutyric acid.
The application of the low-surface-energy waterborne polyurethane in the preparation of the ink comprises the following steps:
adding 40-55 parts of low-surface-energy waterborne polyurethane acrylate and 20-30 parts of acrylate monomer into a stirring barrel, and stirring for 10-20 minutes at the stirring speed of 700-; transferring the pre-dispersed liquid into a grinder, and grinding for 1-3 times; transferring the ground liquid into a stirring barrel, adding 1-10 parts of photoinitiator, 5-10 parts of pigment, 5-15 parts of solvent and 1-5 parts of auxiliary agent into the stirring barrel in sequence, and stirring for 20-30 minutes at the stirring speed of 700 plus materials and 1000rpm to obtain the water-based UV ink with low surface energy.
Further, the acrylate monomer is one or a mixture of butyl acrylate, methyl methacrylate, styrene, acrylic acid and hydroxyethyl acrylate.
Further, the photoinitiator is one or a mixture of 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-acetone, ethyl 2,4, 6-trimethylbenzoylphenylphosphonate and 2-hydroxy-2-methyl-1-phenylpropanone.
Further, one or a mixture of several of deionized water and ethanol as the solvent
Further, the pigment is one or a mixture of more of water-based red pigment, water-based green pigment, water-based blue pigment, water-based yellow pigment and water-based carbon black.
Further, the auxiliary agent is one or a mixture of several of defoaming agent, thickening agent, polymerization inhibitor, flatting agent, dispersing agent and antibacterial agent
The invention has the following beneficial effects:
polysiloxane and glyceryl monostearate are introduced during synthesis of the polyurethane acrylate resin, and the surface energy of silicon-carbon groups in the polysiloxane is low, so that the polysiloxane can migrate to a film/air interface in a coating film drying process; the glyceryl monostearate contains eighteen long alkane side chains, and the long alkane side chains and silicon-carbon groups both belong to hydrophobic groups, and migrate to the surface of the film after the glyceryl monostearate is coated into a film, so that the surface energy of the resin is reduced, and the hydrophobic and oleophobic properties of the coating are improved. The introduction of polysiloxane and monoglyceride reduces the polarity of the ink, and can be widely applied to the surfaces of various base materials such as metal, glass, plastic and the like.
Of course, it is not necessary for any product in which the invention is practiced to achieve all of the above-described advantages at the same time.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings used in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art that other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a water contact angle diagram of an aqueous polyurethane acrylic resin adhesive film.
Detailed Description
The invention will be further illustrated by the following examples of embodiment, without thereby limiting the invention to the scope of the embodiments described, in connection with the drawings of the embodiment of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
(1) Under the protection of nitrogen, 30g of polyoxypropylene glycol (with the molecular weight of 1000), 2.45g of polysiloxane, 3.7g of glyceryl monostearate and 21.42g of isophorone diisocyanate are taken to react for 2-4h at the temperature of 90-95 ℃ in a three-neck flask provided with a stirring rod and a reflux condenser pipe to obtain a solution A; adding 2.59g of dimethylolpropionic acid, 1.11g of 1, 4-butanediol and 10mL of acetone into the solution A, and reacting at 75-80 ℃ for 1h to obtain a solution B; adding 2 drops of stannous octoate, 4 drops of dibutyltin dilaurate and 10mL of acetone into the solution B, and reacting for 3-4h at the temperature of 65-70 ℃ until-NCO reaches a theoretical value to obtain a solution C; adding 3.1g of hydroxyethyl acrylate into the solution C, and reacting at the temperature of 60-70 ℃ for 1-2h to obtain a solution D; and cooling the solution D to below 50 ℃, adding 2.67mL of triethylamine for neutralization, and adding deionized water for emulsification to obtain the low-surface-energy waterborne polyurethane acrylate.
(2) Adding 40 parts of low-surface-energy waterborne polyurethane acrylate, 15 parts of methyl methacrylate and 10 parts of butyl acrylate into a stirring barrel, and stirring for 10-20 minutes at the stirring speed of 700-; transferring the pre-dispersed liquid into a grinder, and grinding for 1-3 times; transferring the ground liquid into a stirring barrel, adding 2 parts of 2,4, 6-trimethyl benzoyl phenyl ethyl phosphonate photoinitiator, 5 parts of water-based red pigment, 10 parts of deionized water and 2 parts of auxiliary agent into the stirring barrel in sequence, and stirring for 20-30 minutes at the stirring speed of 700-1000rpm to obtain the water-based UV ink with low surface energy.
Example 2
(1) Under the protection of nitrogen, 30g of polyoxypropylene glycol (molecular weight 2000), 0.96g of polysiloxane, 2.88g of glyceryl monostearate and 11.03g of toluene diisocyanate are taken to react for 3-4h at 80-85 ℃ in a three-neck flask provided with a stirring rod and a reflux condenser tube to obtain solution A; adding 2.01g of dimethylolpropionic acid, 0.89g of 1, 4-butanediol and 10mL of acetone into the solution A, and reacting at 75-80 ℃ for 1h to obtain a solution B; adding 2 drops of stannous octoate, 3 drops of dibutyltin dilaurate and 10mL of acetone into the solution B, and reacting for 3-4h at the temperature of 65-70 ℃ until-NCO reaches a theoretical value to obtain a solution C; adding 2.05g of hydroxyethyl acrylate into the solution C, and reacting at the temperature of 60-70 ℃ for 1-2h to obtain a solution D; and cooling the solution D to below 50 ℃, adding 2.08mL of triethylamine for neutralization, and adding deionized water for emulsification to obtain the low-surface-energy waterborne polyurethane acrylate.
(2) Adding 45 parts of low-surface-energy waterborne polyurethane acrylate, 12 parts of methyl methacrylate, 12 butyl acrylate and 2 parts of acrylic acid into a stirring barrel, and stirring for 10-20 minutes at the stirring speed of 700-; transferring the pre-dispersed liquid into a grinder, and grinding for 1-3 times; transferring the ground liquid into a stirring barrel, adding 2 parts of 2-hydroxy-2-methyl-1-phenyl-1-acetone photoinitiator, 5 parts of water green pigment, 8 parts of deionized water and 2 parts of auxiliary agent into the stirring barrel in sequence, and stirring for 20-30 minutes at the stirring speed of 700 plus materials and 1000rpm to obtain the water UV ink with low surface energy.
Example 3
1) Under the protection of nitrogen, 30g of polytetrahydrofuran ether glycol (molecular weight 2000), 1.39g of polysiloxane, 2.8g of glyceryl monostearate and 9.88g of toluene diisocyanate are put into a three-neck flask provided with a stirring rod and a reflux condenser tube to react for 3-4h at the temperature of 85-90 ℃ to obtain a solution A; adding 2.09g of dimethylolpropionic acid, 0.08g of 1, 4-butanediol and 10mL of acetone into the solution A, and reacting at 75-80 ℃ for 1h to obtain a solution B; adding 2 drops of stannous octoate, 3 drops of dibutyltin dilaurate and 10mL of acetone into the solution B, and reacting for 3-4h at the temperature of 65-70 ℃ until-NCO reaches a theoretical value to obtain a solution C; adding 2.55g of hydroxyethyl acrylate into the solution C, and reacting at the temperature of 60-70 ℃ for 1-2h to obtain a solution D; and cooling the solution D to below 50 ℃, adding 2.16mL of triethylamine for neutralization, and adding deionized water for emulsification to prepare the low-surface-energy waterborne polyurethane acrylate.
(2) Adding 50 parts of low-surface-energy waterborne polyurethane acrylate, 10 parts of methyl methacrylate and 15 parts of butyl acrylate into a stirring barrel, and stirring for 10-20 minutes at the stirring speed of 700-; transferring the pre-dispersed liquid into a grinder, and grinding for 1-3 times; transferring the ground liquid into a stirring barrel, adding 2 parts of 2,4, 6-trimethyl benzoyl phenyl ethyl phosphonate photoinitiator, 3 parts of water-based carbon black, 10 parts of deionized water and 2 parts of auxiliary agent into the stirring barrel in sequence, and stirring for 20-30 minutes at the stirring speed of 700-1000rpm to obtain the water-based UV ink with low surface energy.
Table one:
group of | Contact angle (°) | Surface energy (mJ/m)2) |
Example 1 | 102.5 | 25.8 |
Example 2 | 108.2 | 17.5 |
Example 3 | 111.6 | 16.4 |
The results of the measurements of the contact angle and the surface energy of the above examples 1 to 3 are shown in Table I.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The preferred embodiments of the invention disclosed above are intended to be illustrative only. The preferred embodiments are not intended to be exhaustive or to limit the invention to the precise embodiments disclosed. Obviously, many modifications and variations are possible in light of the above teaching. The embodiments were chosen and described in order to best explain the principles of the invention and the practical application, to thereby enable others skilled in the art to best utilize the invention. The invention is limited only by the claims and their full scope and equivalents.
Claims (10)
1. The preparation method of the low-surface-energy waterborne polyurethane is characterized by comprising the following steps of: end capping is carried out on polyurethane by utilizing hydroxyethyl acrylate, and a carbon-carbon double bond functional group is introduced; introducing organosilicon group and one octadecane long alkane side chain into the main chain of polyurethane.
2. The preparation method of the low-surface-energy waterborne polyurethane as claimed in claim 1, wherein the preparation method specifically comprises the following steps:
s01, under the protection of nitrogen, adding polyester or polyether polyol, diisocyanate, polysiloxane and glyceryl monostearate into a reactor, and reacting at the temperature of 75-90 ℃ for 2-4h to obtain a solution A;
s02, adding a hydrophilic chain extender and a micromolecular dihydric alcohol chain extender into the solution A, and reacting for 1-2 hours at the temperature of 70-80 ℃ to obtain a solution B;
s03, adding a catalyst into the solution B, and reacting for 2-4h at the temperature of 60-75 ℃ until-NCO reaches a theoretical value to obtain a solution C;
s04, adding hydroxyethyl acrylate into the solution C, and reacting at the temperature of 60-70 ℃ for 1-2h to obtain a solution D;
s05, cooling the solution D to below 50 ℃, adding triethylamine for neutralization, and then adding deionized water for emulsification to obtain the low-surface-energy waterborne polyurethane acrylate.
3. The preparation of a low surface energy aqueous polyurethane according to claim 2, wherein the molar ratio of the amount of the diisocyanate to the sum of the amounts of the polyester or polyether diol and the polysiloxane is 2 to 7.
4. The preparation method of the low-surface-energy waterborne polyurethane as claimed in claim 2, wherein the catalyst is contained in an amount of 0.05 to 0.3% by mass.
5. The preparation method of the low surface energy waterborne polyurethane of claim 2, wherein the polyester or polyether polyol is one or more of polyoxyethylene glycol, polyoxypropylene glycol, poly-1, 4-butylene adipate glycol, polytetrahydrofuran ether glycol, hydroxyl-terminated polybutadiene, polycaprolactone diol and polycarbonate diol.
6. The preparation method of the low surface energy waterborne polyurethane of claim 2, wherein the diisocyanate is one or more of toluene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate and hexamethylene diisocyanate.
7. The preparation method of the low surface energy aqueous polyurethane as claimed in claim 2, wherein the polysiloxane is hydroxyl terminated polydimethylsiloxane with molecular weight of 600-4000.
8. The preparation method of the low-surface-energy waterborne polyurethane as claimed in claim 2, wherein the catalyst is one or a mixture of stannous octoate, dibutyltin dilaurate, triethanolamine and triethylene diamine.
9. The preparation of the low surface energy aqueous polyurethane of claim 2, wherein the hydrophilic chain extender is one or a mixture of dimethylolpropionic acid and dimethylolbutyric acid.
10. Use of a low surface energy aqueous polyurethane prepared according to any of claims 1 to 9 in the preparation of an ink comprising:
adding 40-55 parts of low-surface-energy waterborne polyurethane acrylate and 20-30 parts of acrylate monomer into a stirring barrel, and stirring for 10-20 minutes at the stirring speed of 700-; transferring the pre-dispersed liquid into a grinder, and grinding for 1-3 times; transferring the ground liquid into a stirring barrel, adding 1-10 parts of photoinitiator, 5-10 parts of pigment, 5-15 parts of solvent and 1-5 parts of auxiliary agent into the stirring barrel in sequence, and stirring for 20-30 minutes at the stirring speed of 700 plus materials and 1000rpm to obtain the water-based UV ink with low surface energy.
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CN111286199A (en) * | 2020-03-20 | 2020-06-16 | 宁波俊瑆玩具科技有限公司 | High-elasticity high-toughness recovery adhesive |
CN114075423A (en) * | 2020-08-17 | 2022-02-22 | 上海天洋热熔粘接材料股份有限公司 | Low-surface-energy copolyester hot melt adhesive and preparation method thereof |
CN114075424A (en) * | 2020-08-17 | 2022-02-22 | 上海天洋热熔粘接材料股份有限公司 | Low-surface-energy single-component moisture-curing polyurethane hot melt adhesive and preparation method thereof |
CN115785596A (en) * | 2022-12-08 | 2023-03-14 | 华南理工大学 | Modified PVA film containing hydrophobic coating and loaded with nano gas barrier material, and preparation method and application thereof |
CN116179012A (en) * | 2022-12-23 | 2023-05-30 | 杭州柏盛印刷有限公司 | Water-based UV (ultraviolet) ink and preparation method thereof |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101805438A (en) * | 2010-04-13 | 2010-08-18 | 江苏工业学院 | Preparation method and applications of cationic waterborne polyurethane surface sizing agent |
CN101735599B (en) * | 2009-12-24 | 2011-12-07 | 华南理工大学 | Ultraviolet curing organic silicon modified polyurethane aqueous dispersoid and preparation method thereof |
CN103613993A (en) * | 2013-11-21 | 2014-03-05 | 武汉大学 | Hydroxyl silicone oil modified waterborne UV (Ultraviolet) printing ink and preparation method thereof |
CN103881049A (en) * | 2014-04-04 | 2014-06-25 | 中南林业科技大学 | Preparation method of eleostearic acid monoglyceride modified waterborne polyurethane emulsion |
CN105131807A (en) * | 2015-10-13 | 2015-12-09 | 厦门大学 | Hydrophobic water-based fluorescent polyurethane paint and preparation method thereof |
CN108486294A (en) * | 2018-04-04 | 2018-09-04 | 江西三越新材料有限公司 | UV type leather flatting inorganic agents and preparation method thereof |
CN108504269A (en) * | 2018-03-26 | 2018-09-07 | 华南理工大学 | A kind of floride-free nonpolluting coating and preparation method thereof of ultraviolet light/sun light curable |
CN110078928A (en) * | 2019-04-26 | 2019-08-02 | 深圳职业技术学院 | A kind of low-surface-energy highly-water-soluble UV-Curing Waterborne Resin and preparation method thereof |
-
2019
- 2019-11-15 CN CN201911120155.8A patent/CN110818872A/en active Pending
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101735599B (en) * | 2009-12-24 | 2011-12-07 | 华南理工大学 | Ultraviolet curing organic silicon modified polyurethane aqueous dispersoid and preparation method thereof |
CN101805438A (en) * | 2010-04-13 | 2010-08-18 | 江苏工业学院 | Preparation method and applications of cationic waterborne polyurethane surface sizing agent |
CN103613993A (en) * | 2013-11-21 | 2014-03-05 | 武汉大学 | Hydroxyl silicone oil modified waterborne UV (Ultraviolet) printing ink and preparation method thereof |
CN103881049A (en) * | 2014-04-04 | 2014-06-25 | 中南林业科技大学 | Preparation method of eleostearic acid monoglyceride modified waterborne polyurethane emulsion |
CN105131807A (en) * | 2015-10-13 | 2015-12-09 | 厦门大学 | Hydrophobic water-based fluorescent polyurethane paint and preparation method thereof |
CN108504269A (en) * | 2018-03-26 | 2018-09-07 | 华南理工大学 | A kind of floride-free nonpolluting coating and preparation method thereof of ultraviolet light/sun light curable |
CN108486294A (en) * | 2018-04-04 | 2018-09-04 | 江西三越新材料有限公司 | UV type leather flatting inorganic agents and preparation method thereof |
CN110078928A (en) * | 2019-04-26 | 2019-08-02 | 深圳职业技术学院 | A kind of low-surface-energy highly-water-soluble UV-Curing Waterborne Resin and preparation method thereof |
Non-Patent Citations (2)
Title |
---|
XIAOLI LIU,等: ""Novel waterborne polyurethanes containing longchain alkanes: their synthesis and application to water repellency"", 《RSC ADVANCES》 * |
詹媛媛等: "硬脂酸单甘油酯改性水性聚氨酯的研究", 《涂料工业》 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111286199A (en) * | 2020-03-20 | 2020-06-16 | 宁波俊瑆玩具科技有限公司 | High-elasticity high-toughness recovery adhesive |
CN111286199B (en) * | 2020-03-20 | 2022-04-05 | 宁波俊瑆玩具科技有限公司 | High-elasticity high-toughness recovery adhesive |
CN114075423A (en) * | 2020-08-17 | 2022-02-22 | 上海天洋热熔粘接材料股份有限公司 | Low-surface-energy copolyester hot melt adhesive and preparation method thereof |
CN114075424A (en) * | 2020-08-17 | 2022-02-22 | 上海天洋热熔粘接材料股份有限公司 | Low-surface-energy single-component moisture-curing polyurethane hot melt adhesive and preparation method thereof |
CN115785596A (en) * | 2022-12-08 | 2023-03-14 | 华南理工大学 | Modified PVA film containing hydrophobic coating and loaded with nano gas barrier material, and preparation method and application thereof |
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CN116179012A (en) * | 2022-12-23 | 2023-05-30 | 杭州柏盛印刷有限公司 | Water-based UV (ultraviolet) ink and preparation method thereof |
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