CN113912784A - Preparation method and application of waterborne polyurethane acrylate resin - Google Patents
Preparation method and application of waterborne polyurethane acrylate resin Download PDFInfo
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- CN113912784A CN113912784A CN202111222712.4A CN202111222712A CN113912784A CN 113912784 A CN113912784 A CN 113912784A CN 202111222712 A CN202111222712 A CN 202111222712A CN 113912784 A CN113912784 A CN 113912784A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
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Abstract
The invention discloses a preparation method and application of waterborne polyurethane acrylate resin, wherein vinyl acetate-ethylene copolymer emulsion and a cross-linking agent are heated to react; adding an isocyanate curing agent, and continuing to react; adding hydroxyl ketone, polyester polyol and hydrophilic functional monomer, and reacting to obtain a polyurethane prepolymer; adding acrylate monomer to dilute according to the viscosity in the reaction process; adding photosensitive diluted active monomer, and reacting while maintaining the temperature; and (3) cooling, adding triethylamine under a low-temperature condition for low-temperature reaction, adding water, and stirring to obtain the waterborne polyurethane acrylate resin. The invention can be used for printing adhesives, and after heating and curing, the coating has the characteristics of high adhesive force, excellent water resistance and solvent resistance and the like.
Description
Technical Field
The invention belongs to the technical field of textile materials, and particularly relates to a preparation method of a water-based polyurethane acrylate resin.
Background
In the coating industry, polyurethane is widely applied and is one of the coating varieties with the highest growth speed. It is even thought that the proportion and growth rate of the paint in the industry represent the development level of the coating industry in a country. However, most of the traditional solvent-based PU coatings contain a large amount of organic solvents and a certain amount of free isocyanate, and a large amount of the organic solvents and the free isocyanate volatilize in the using process, so that the health of people is damaged, and the environment is also seriously polluted.
The waterborne polyurethane acrylic resin is most applied to a UV curing waterborne system due to the excellent comprehensive performance. For aqueous polyurethane acrylic resin systems, high solids contents and low system viscosities have long been the goals sought by researchers, particularly when applied to UV-curable systems. High solids content means a reduction in the amount of water used in the system, i.e. a reduction in energy consumption; however, most of the water-based polyurethane systems on the market at present contain less than 40 percent of solid content, so that great waste exists on energy sources, and the performance is not slightly lost. In addition, the common problems of low double bond content, insufficient film crosslinking degree, poor mechanical property and heat resistance and the like of the UV curing system also become difficult problems for researchers.
Disclosure of Invention
The invention mainly solves the technical problem of providing a preparation method and application of a waterborne polyurethane acrylate resin, wherein the resin can be used for printing adhesives, and after being heated and cured, a coating of the resin has the characteristics of high adhesive force, excellent water resistance and solvent resistance and the like.
In order to solve the technical problems, the invention adopts a technical scheme that:
a preparation method of the waterborne polyurethane acrylate resin comprises the following steps:
(1) heating vinyl acetate-ethylene copolymer emulsion and a cross-linking agent for reaction;
(2) adding an isocyanate curing agent, and continuing to react;
(3) adding hydroxyl ketone, polyester polyol and hydrophilic functional monomer, and reacting to obtain a polyurethane prepolymer; adding acrylate monomer to dilute according to the viscosity in the reaction process;
(4) adding photosensitive diluted active monomer, and reacting while maintaining the temperature; cooling, adding triethylamine under a low-temperature condition for low-temperature reaction, adding water, and stirring to obtain the waterborne polyurethane acrylate resin;
the vinyl acetate-ethylene copolymer emulsion has a glass transition temperature of 27-40 ℃ and a solid content of 45-60%;
the photosensitive diluted active monomer is trimethylolpropane triacrylate, hydroxyethyl acrylate and oxazolidone modified acrylate according to the weight ratio of 2: 1: 0.5 mass ratio.
The preparation method comprises the following steps of taking the weight of the non-aqueous component in the aqueous polyurethane acrylate as 100%, wherein the use amount of each component is as follows by mass: 5-10% of vinyl acetate-ethylene copolymer emulsion, 25-46% of cross-linking agent, 10-25% of isocyanate curing agent, 2-7% of hydroxy ketone, 1-3% of polyester polyol, 0.5-3% of hydrophilic functional monomer, 35-70% of acrylate monomer dilution, 1-3% of photosensitive dilution active monomer, 3-6% of triethylamine and 150-250% of water.
Reacting for 0.5-1.5 hours at 81-300 ℃ in the reaction in the step (1); reacting for 2-4 hours at 81-300 ℃ in the reaction in the step (2); reacting for 1-4 hours at 60-90 ℃ in the reaction in the step (3); carrying out heat preservation reaction at 60-80 ℃ for 0.5-1.5 hours in the step (4); the low temperature is 0-20 ℃, the low temperature reaction time is 1-3 minutes, and the stirring time is 1-5 minutes.
The preparation method of the waterborne polyurethane acrylate resin can be summarized as follows: taking the weight of non-aqueous components in the aqueous polyurethane acrylate as a reference, reacting 5-10% of vinyl acetate-ethylene copolymer emulsion and 25-46% of cross-linking agent at 81-300 ℃ for 0.5-1.5 hours, adding 10-25% of isocyanate curing agent, and reacting at 81-300 ℃ for 2-4 hours; adding 2-7% of hydroxy ketone, 1-3% of polyester polyol and 0.5-3% of hydrophilic functional monomer, and reacting at 60-90 ℃ for 1-4 hours to obtain a polyurethane prepolymer; adding 35-70% of acrylate monomer according to the viscosity during the reaction process for dilution; then adding 1-3% of photosensitive diluted active monomer, and reacting for 0.5-1.5 hours at 60-80 ℃; adding 3-6% of triethylamine to react for 1-3 minutes at 0-20 ℃, adding 150-250% of water, and stirring for 1-5 minutes to obtain a product; the vinyl acetate-ethylene copolymer emulsion has a glass transition temperature of 27-40 ℃ and a solid content of 45-60%; the photosensitive diluted active monomer is trimethylolpropane triacrylate, hydroxyethyl acrylate and oxazolidone modified acrylate according to the weight ratio of 2: 1: 0.5 mass ratio.
Further, the cross-linking agent is one or more of isocyanate compound, melamine compound, oxazoline compound, aziridine compound, epoxy compound and carbodiimide compound.
Further, the isocyanate curing agent is BASF aliphatic polyisocyanate HI 100.
Further, the hydroxy ketone is one or more of hydroxyacetophenone, hydroxy propiophenone and hydroxy butanone.
Further, the polyester polyol contains a sulfonate group in a segment thereof.
Further, the hydrophilic functional monomer is one or more of dimethylolpropionic acid (DMPA), dimethylolbutyric acid (DMBA), pyromellitic dianhydride (BPDA), 1, 2-propylene glycol-3-sodium sulfonate, 1, 4-butanediol-2-sodium sulfonate and 2- [ (2-aminoethyl) amino ] ethanesulfonic acid sodium salt.
Further, the acrylate monomer is one or more of methyl methacrylate, methyl acrylate, butyl methacrylate, ethyl acrylate, glycidyl methacrylate and glycidyl acrylate.
Further, during the reaction, acrylate monomers are added according to the viscosity, and the viscosity is obtained through a viscosity detection system, wherein the viscosity detection system comprises: the viscosity analysis device comprises a data acquisition module, a detection information module, a central control module, a result display module and a data analysis module, wherein the data acquisition module is embedded into the inner wall of a preparation container of the waterborne polyurethane acrylate resin and connected with the data analysis module and used for acquiring detection signal test information and transmitting the acquired detection signal test information to the data analysis module, the data analysis module is further connected with the information detection module and the central control module and used for combining the detection signal test information transmitted by the data acquisition module with the detection signal information in the detection information module to perform data analysis, determining a viscosity analysis result and feeding the viscosity analysis result back to the central control module, and the central control module is further connected with the detection information module and the result display module and respectively used for controlling the detection information module to transmit the detection signal information and controlling the result display module to perform viscosity analysis And (6) presenting the analysis result.
Further, stir through the stirring rod when stirring for 1 ~ 5 minutes, the stirring rod includes: handheld device and agitating unit, handheld device is the telescopic link, agitating unit includes (mixing) shaft and fixed part, the telescopic link with stirring shaft connection, the (mixing) shaft still with fixed part connects, when utilizing when the stirring rod stirs, through fixed part will the stirring shaft supports and gets up to fix, makes the (mixing) shaft presents specific shape, adjusts according to the demand simultaneously the length of telescopic link can stir the use.
An application of water-based polyurethane acrylate resin in printing adhesives.
The invention has the following beneficial effects:
1. the polyester polyol contains a sulfonate group in a chain segment, the sulfonate group has excellent hydrophilicity, has better stability than anionic waterborne polyurethane acrylate, is not influenced by pH and electrolyte, and does not need to be neutralized by amine substances, so the synthesized waterborne polyurethane acrylate has good stability and water dispersibility;
2. according to the invention, the end of the acrylate is connected with polyurethane to form a complex crosslinked network, so that the defects of poor weather resistance, poor initial water resistance, poor heat resistance and the like of the waterborne polyurethane acrylate are overcome, the hydroxy ketone is introduced into the polyurethane chain segment by a chemical grafting method, the polyurethane chain segment has high tensile strength, the flexibility of the coating is greatly improved under the condition of not influencing the modulus of the polyurethane chain segment, and the special performance of the coating is shown.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention. In the drawings:
FIG. 1 is a schematic view of a viscosity detection system according to the present invention;
FIG. 2 is a schematic view of a stir bar according to the present invention.
Detailed Description
The following detailed description of the preferred embodiments of the present invention is provided to enable those skilled in the art to more readily understand the advantages and features of the present invention, and to clearly and unequivocally define the scope of the present invention.
Example 1
Taking the weight of non-aqueous components in the aqueous polyurethane acrylate as a reference, reacting 5% of vinyl acetate-ethylene copolymer emulsion and 46% of cross-linking agent at 300 ℃ for 1.3 hours, adding 18% of isocyanate curing agent, and reacting at 300 ℃ for 3 hours; adding 2% of hydroxy ketone, 1% of polyester polyol and 0.5% of hydrophilic functional monomer, and reacting for 4 hours at 70 ℃ to obtain a polyurethane prepolymer; adding 40% of acrylate monomer for dilution according to the viscosity in the reaction process; then adding 3% of photosensitive diluted active monomer, and reacting for 1.3 hours at 70 ℃; adding 3% of triethylamine to react for 3 minutes at the temperature of 20 ℃, adding 200% of water, and stirring for 4 minutes to obtain the waterborne polyurethane acrylate resin.
Example 2
Taking the weight of non-aqueous components in the aqueous polyurethane acrylate as a reference, reacting 7% of vinyl acetate-ethylene copolymer emulsion with 30% of cross-linking agent at 200 ℃ for 0.5 hour, adding 15% of isocyanate curing agent, and reacting at 200 ℃ for 4 hours; adding 4% of hydroxy ketone, 2% of polyester polyol and 1% of hydrophilic functional monomer, and reacting for 3 hours at 60 ℃ to obtain a polyurethane prepolymer; adding 35% of acrylate monomer for dilution according to the viscosity in the reaction process; then 2% of photosensitive diluted active monomer is added to react for 1 hour at 80 ℃; adding 4% of triethylamine to react for 2 minutes at the temperature of 0 ℃, adding 180% of triethylamine and stirring for 5 minutes to obtain the waterborne polyurethane acrylate resin.
Example 3
Taking the weight of non-aqueous components in the aqueous polyurethane acrylate as a reference, reacting 9% of vinyl acetate-ethylene copolymer emulsion and 25% of cross-linking agent at 100 ℃ for 1.5 hours, adding 10% of isocyanate curing agent, and reacting at 100 ℃ for 24 hours; adding 5% of hydroxy ketone, 1% of polyester polyol and 2% of hydrophilic functional monomer, and reacting for 2 hours at 90 ℃ to obtain a polyurethane prepolymer; adding 50 acrylate monomers according to the viscosity during the reaction process for dilution; then adding 1.6 sensitive diluted active monomer, and reacting for 0.5 hour at 60 ℃; adding 5% of triethylamine to react for 3 minutes at 10 ℃, adding 250% of water, and stirring for 1 minute to obtain the waterborne polyurethane acrylate resin.
Example 4
Taking the weight of non-aqueous components in the aqueous polyurethane acrylate as a reference, reacting 10% of vinyl acetate-ethylene copolymer emulsion with 42% of cross-linking agent at 81 ℃ for 1 hour, adding 25% of isocyanate curing agent, and reacting at 81 ℃ for 3 hours; adding 7% of hydroxy ketone, 3% of polyester polyol and 3% of hydrophilic functional monomer, and reacting at 80 ℃ for 1 hour to obtain a polyurethane prepolymer; adding 70% of acrylate monomer for dilution according to the viscosity in the reaction process; then 1% of photosensitive diluted active monomer is added to react for 1.5 hours at 70 ℃; adding 6% of triethylamine to react for 1 minute at the temperature of 5 ℃, adding 150% of water, and stirring for 2 minutes to obtain the waterborne polyurethane acrylate resin.
The aqueous urethane acrylate resins prepared in examples 1 to 4 and the commercially available aqueous urethane acrylate resins (comparative example 1 to comparative example 2) were subjected to the relevant performance tests, and the results are shown in table 1:
TABLE 1
As can be seen from the data in Table 1, the water resistance of the waterborne polyurethane acrylate resin prepared by the method is obviously superior to that of the commercially available waterborne polyurethane acrylate resin, and the peel strength of the waterborne polyurethane acrylate resin is also obviously improved.
Example 5
Based on example 1, 35-70% of acrylate monomer is added to dilute according to the viscosity during the reaction process, wherein the viscosity is obtained by a viscosity detection system, as shown in fig. 1, and the viscosity detection system comprises: the viscosity detection system comprises a data acquisition module, a detection information module, a central control module, a result display module and a data analysis module, wherein the data acquisition module is embedded into the inner wall of a preparation container of the waterborne polyurethane acrylate resin and is connected with the data analysis module, the data analysis module is also connected with the information detection module and the central control module, the central control module is also connected with the detection information module and the result display module, when the viscosity is determined by a viscosity detection system, the central control module controls the detection information module to send detection signal information, then the data acquisition module receives the detection signal information to obtain detection signal test information, transmits the acquired detection signal test information to the data analysis module, and then the data analysis module combines the detection signal test information transmitted by the data acquisition module with the detection signal information in the detection information module to perform data analysis, confirm the viscosity analysis result, feed back the viscosity analysis result to central control module again, central control module control result display module shows the viscosity analysis result at last, above-mentioned viscosity detection system not only can be through the size of result display module visual display viscosity, but also can avoid subjective analysis to judge, detect fastly, the accuracy is high to when data analysis module confirms the viscosity analysis result, confirm through the following formula:
n＝n0*(1+r)
in the above formula, n represents a viscosity detection value, n0Representing the air viscosity value under the current temperature condition, r representing the intermediate quantity, w representing the detection signal information sent by the detection information module, wiRepresenting the test information of the detection signal collected by the ith collection device in the data collection module, n representing the number of the collection devices in the data collection module, diRepresents the linear distance, w, between the ith acquisition device and the detection information module in the data acquisition moduleoTest information y representing the test information of the test signal received at a transmission distance L in the airiAnd the value of the adjusting parameter is the transmission distance in the air in the linear distance between the ith acquisition device in the data acquisition module and the information detection module.
The viscosity is specifically determined by combining the air viscosity value under the current temperature condition, so that an operation reference is provided for diluting 35-70% of acrylate monomers according to the viscosity, errors can be effectively reduced by adjusting parameters, and the accuracy of the calculated viscosity detection value is improved.
Example 6
Based on example 1, 3-6% of triethylamine is added at 0-20 ℃ for reaction for 1-3 minutes, 150-250% of water is added, and stirring is carried out for 1-5 minutes, so that in the process of obtaining the triethylamine-based organic silicon dioxide, stirring is carried out through a stirring rod when stirring is carried out for 1-5 minutes, and the stirring rod comprises: the stirring rod is supported and fixed by the fixing part when being used for stirring, so that the stirring shaft is in an S shape from top to bottom, the stirring rod can be stirred for use by adjusting the length of the telescopic rod according to requirements, materials with different viscosities can be stirred by forming the stirring shaft into the S shape from top to bottom, the applicability of the stirring rod in the preparation process of the waterborne polyurethane acrylate resin is improved, the length of the telescopic rod can be adjusted according to requirements, 3-6% of triethylamine is added at the temperature of 0-20 ℃ for reaction for 1-3 minutes, the stirring shaft can be fully stirred after 150-250% of water is added, better waterborne polyurethane acrylate resin is obtained, and when the stirring shaft is not used, the fixing of the fixing part on the stirring shaft can be released, the telescopic rod is contracted to the shortest length, and the use is convenient.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all equivalent structural changes made by using the contents of the present specification, or any other related technical fields directly or indirectly, are included in the scope of the present invention.
Claims (10)
1. A preparation method of the waterborne polyurethane acrylate resin is characterized by comprising the following steps: the method comprises the following steps:
(1) heating vinyl acetate-ethylene copolymer emulsion and a cross-linking agent for reaction;
(2) adding an isocyanate curing agent, and continuing to react;
(3) adding hydroxyl ketone, polyester polyol and hydrophilic functional monomer, and reacting to obtain a polyurethane prepolymer; adding acrylate monomer to dilute according to the viscosity in the reaction process;
(4) adding photosensitive diluted active monomer, and reacting while maintaining the temperature; cooling, adding triethylamine under a low-temperature condition for low-temperature reaction, adding water, and stirring to obtain the waterborne polyurethane acrylate resin;
the vinyl acetate-ethylene copolymer emulsion has a glass transition temperature of 27-40 ℃ and a solid content of 45-60%;
the photosensitive diluted active monomer is trimethylolpropane triacrylate, hydroxyethyl acrylate and oxazolidone modified acrylate according to the weight ratio of 2: 1: 0.5 mass ratio.
2. The method for producing the aqueous urethane acrylate resin according to claim 1, characterized in that: the preparation method comprises the following steps of taking the weight of the non-aqueous component in the aqueous polyurethane acrylate as 100%, wherein the use amount of each component is as follows by mass: 5-10% of vinyl acetate-ethylene copolymer emulsion, 25-46% of cross-linking agent, 10-25% of isocyanate curing agent, 2-7% of hydroxy ketone, 1-3% of polyester polyol, 0.5-3% of hydrophilic functional monomer, 35-70% of acrylate monomer dilution, 1-3% of photosensitive dilution active monomer, 3-6% of triethylamine and 150-250% of water.
3. The method for producing the aqueous urethane acrylate resin according to claim 1, characterized in that: reacting for 0.5-1.5 hours at 81-300 ℃ in the reaction in the step (1); reacting for 2-4 hours at 81-300 ℃ in the reaction in the step (2); reacting for 1-4 hours at 60-90 ℃ in the reaction in the step (3); carrying out heat preservation reaction at 60-80 ℃ for 0.5-1.5 hours in the step (4); the low temperature is 0-20 ℃, the low temperature reaction time is 1-3 minutes, and the stirring time is 1-5 minutes.
4. The method for preparing an aqueous urethane acrylate resin according to claim 1, wherein: one or more of isocyanate compound, melamine compound, oxazoline compound, aziridine compound, epoxy compound and carbodiimide compound serving as the crosslinking agent; the isocyanate curing agent is BASF aliphatic polyisocyanate HI 100.
5. The method for preparing an aqueous urethane acrylate resin according to claim 1, wherein: the hydroxy ketone is one or more of hydroxyacetophenone, hydroxy propiophenone and hydroxy butanone; the chain segment of the polyester polyol contains sulfonate groups.
6. The method for preparing an aqueous urethane acrylate resin according to claim 1, wherein: the hydrophilic functional monomer is one or more of dimethylolpropionic acid (DMPA), dimethylolbutyric acid (DMBA), pyromellitic dianhydride (BPDA), 1, 2-propylene glycol-3-sodium sulfonate, 1, 4-butanediol-2-sodium sulfonate and 2- [ (2-aminoethyl) amino ] ethanesulfonic acid sodium salt.
7. The method for preparing an aqueous urethane acrylate resin according to claim 1, wherein: the acrylate monomer is one or more of methyl methacrylate, methyl acrylate, butyl methacrylate, ethyl acrylate, glycidyl methacrylate and glycidyl acrylate.
8. The method for preparing an aqueous urethane acrylate resin according to claim 1, wherein: in the reaction process, an acrylate monomer is added according to the viscosity to dilute, the viscosity is obtained through a viscosity detection system, and the viscosity detection system comprises: the viscosity analysis device comprises a data acquisition module, a detection information module, a central control module, a result display module and a data analysis module, wherein the data acquisition module is embedded into the inner wall of a preparation container of the waterborne polyurethane acrylate resin and connected with the data analysis module and used for acquiring detection signal test information and transmitting the acquired detection signal test information to the data analysis module, the data analysis module is further connected with the information detection module and the central control module and used for combining the detection signal test information transmitted by the data acquisition module with the detection signal information in the detection information module to perform data analysis, determining a viscosity analysis result and feeding the viscosity analysis result back to the central control module, and the central control module is further connected with the detection information module and the result display module and respectively used for controlling the detection information module to transmit the detection signal information and controlling the result display module to perform viscosity analysis And (6) presenting the analysis result.
9. The method for preparing an aqueous urethane acrylate resin according to claim 1, wherein: stir through the stirring rod when stirring 1 ~ 5 minutes, the stirring rod includes: handheld device and agitating unit, handheld device is the telescopic link, agitating unit includes (mixing) shaft and fixed part, the telescopic link with stirring shaft connection, the (mixing) shaft still with fixed part connects, when utilizing when the stirring rod stirs, through fixed part will the stirring shaft supports and gets up to fix, makes the (mixing) shaft presents specific shape, adjusts according to the demand simultaneously the length of telescopic link can stir the use.
10. An application of water-based polyurethane acrylate resin in printing adhesives.
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2021
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