CN111621001B - UV (ultraviolet) curing water-based resin and preparation method thereof - Google Patents
UV (ultraviolet) curing water-based resin and preparation method thereof Download PDFInfo
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Abstract
The invention provides a UV-curable water-based resin and a preparation method thereof. The UV-cured waterborne resin is polyurethane modified acrylate UV resin generated by the reaction of polyurethane modified acrylate and amine alkyl sulfonate, has hardness adjustability, and can adjust and control the hardness and flexibility of a cured film by changing the molecular weight of dihydric alcohol in raw materials for synthesizing the polyurethane modified acrylate; the curing agent has the characteristics of polyurethane and acrylate, and a curing film of the curing agent has high hardness, good adhesive force and flexibility, smooth appearance and full paint film; the emulsifying property of the resin and the water resistance of the cured film can be balanced by controlling the content of the hydrophilic group. When the UV-curable water-based resin is used as the main component of the UV-curable water-based paint, the fluidity of the paint can be adjusted by replacing an active diluent with water, the UV-curable water-based resin is environment-friendly, the film curing shrinkage phenomenon is improved, and the UV-curable water-based resin has the advantages of thin coating, easy cleaning of construction equipment and the like. The preparation method is simple, has low requirements on equipment, and is easy to realize industrialization.
Description
Technical Field
The invention relates to the technical field of water-based paint, in particular to UV (ultraviolet) curing water-based resin and a preparation method thereof.
Background
The UV curing coating has the advantages of environmental protection, high efficiency and the like, and the formed curing film has excellent comprehensive performance and is widely applied to coating of wooden products, plastic products and metal products. The UV-curable water-based resin is a key component in the UV-curable water-based paint, and the molecular structure, molecular weight, functionality and the like of the UV-curable water-based resin determine the performance of a cured film. The polyurethane modified acrylate UV resin has good flexibility, adhesive force, wear resistance, weather resistance and the like, the hardness can be regulated and controlled through a molecular structure, the viscosity is usually high, and an active diluent is required to be added in a coating formula. The traditional UV curing coating needs to be added with an acrylate reactive diluent, and the reactive diluent has certain sensitization, possibly causes certain harm to human bodies and can cause a curing film to shrink to a certain extent.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: the novel UV-curing water-based resin is obtained by modifying the existing polyurethane modified acrylate, so that the novel UV-curing water-based resin does not need to be added with an acrylate reactive diluent during application.
In order to solve the technical problems, the invention adopts the technical scheme that:
the UV-curable water-based resin is prepared by reacting A and B, wherein A is polyurethane modified acrylate, and B is amine alkyl sulfonate.
Further, the structural formula of A is as follows:
wherein R is
R1Is composed of
R2Is composed of
R3Is composed of
R5Is composed of
R6Is composed of
R0Is H or Me, R4Is H or Me, R7Is H or Me, R8Is H or Me; n ranges from 2 to 20, n1The value range of (1) to (30), the value range of m is from 2 to (20), m1The value range of (a) is 1-30, and the value range of p is 1-30.
Further, said B is composed of
wherein, the value range of x is 2-20, and Y+Is Na+And/or K+And/or NH4 +，Z+Is Na+And/or K+And/or NH4 +。
Further, the reaction is a Michael addition reaction, and the molar weight ratio of the A to the B is 1: (0.5-2.0) carrying out the reaction.
A preparation method of UV-cured water-based resin comprises the steps of preparing A and B as required, adding A into a reaction bottle, adding a solvent to dissolve A, heating to 40-50 ℃, slowly dropwise adding B into the reaction bottle, keeping the temperature after dropwise adding is finished, reacting until the reaction is finished, and carrying out post-treatment to obtain the UV-cured water-based resin, wherein A is polyurethane modified acrylate, and B is amine alkyl sulfonate.
Further, the volume of the added solvent is 0.5-2 times of the volume of the A; the solvent is prepared by mixing water and an organic solvent according to a volume ratio of 1: and (1-4) are mixed according to the proportion.
Further, the solvent is one of ethanol/water mixed solvent, acetone/water mixed solvent and N-methylpyrrolidone/water mixed solvent.
Further, the reaction time of the heat preservation reaction is 24-48 h.
Further, the post-processing is as follows: removing the organic solvent by distillation under reduced pressure; the pressure of the reduced pressure distillation is-0.09 MPa to-0.1 MPa, and the temperature is 40-150 ℃.
Further, detecting the primary amine value in the reaction system, and judging that the reaction is finished when the primary amine value is less than 4mg KOH/g and tends to be stable.
The invention has the beneficial effects that:
1. the UV-cured water-based resin is polyurethane modified acrylate UV resin, has hardness adjustability, and can adjust and control the hardness and flexibility of a cured film by changing the molecular weight of dihydric alcohol in raw materials for synthesizing the polyurethane modified acrylate.
2. The UV-cured water-based resin has the characteristics of polyurethane and acrylate, and a cured film of the UV-cured water-based resin has high hardness, good adhesive force and flexibility, smooth appearance and full paint film.
3. The UV-curable aqueous resin of the present invention can balance the emulsification properties of the resin and the water resistance of the cured film by controlling the content of hydrophilic groups.
4. The preparation method of the UV-curable water-based resin provided by the invention is simple, has low requirements on equipment, and is easy to realize industrialization.
5. The UV-curable water-based resin provided by the invention is used as a UV-curable water-based paint, the fluidity of the paint can be adjusted by replacing an active diluent with water, and the UV-curable water-based resin is environment-friendly and can improve the film curing shrinkage phenomenon. In addition, the UV-curable water-based paint also has the advantages of thin coating, easy cleaning of construction equipment and the like.
Detailed Description
The most key concept of the invention is as follows: hydrophilic groups are introduced into the molecular structure to enable the molecular structure to have certain hydrophilicity, the UV-cured waterborne polyurethane modified acrylate resin is prepared, and water is used for replacing an acrylate reactive diluent for dilution when the UV-cured waterborne polyurethane modified acrylate resin is applied.
In order to further discuss the feasibility of the inventive concept, the detailed description of the technical content, the constructional features, the objects and the effects achieved according to the invention is given in detail.
Example 1
A UV-curable waterborne resin is generated by performing Michael addition reaction on A and B, wherein A is polyurethane modified acrylate, and B is amine alkyl sulfonate; the molar weight ratio of the A to the B is 1: (0.5-2.0) carrying out the reaction. The structural formula of A is as follows:
wherein R is
R1Is composed of
R2Is composed of
R3Is composed of
R5Is composed of
R6Is composed of
R0Is H or Me, R4Is H or Me, R7Is H or Me, R8Is H or Me; n ranges from 2 to 20, n1The value range of (1) to (30), the value range of m is from 2 to (20), m1The value range of (a) is 1-30, and the value range of p is 1-30.
Said B is composed of
And/or
The value range of x is 2-20, and Y is+Is Na+And/or K+And/or NH4 +，Z+Is Na+And/or K+And/or NH4 +. B can also be H with two or more x values different in value2N-(CH2)x-SO3 -Y+And (4) mixing.
Example 2
A preparation method of UV curing water-based resin comprises the steps of preparing A and B as required, adding A into a reaction bottle, adding a proper amount of solvent to dissolve A, heating to 40-50 ℃, slowly dropwise adding B into the reaction bottle, and after dropwise adding is completed, carrying out heat preservation reaction for 24-48 h; detecting the primary amine value in the reaction system when the heat preservation reaction is carried out for 24-48h, and judging that the reaction is finished when the primary amine value is less than 4mg KOH/g and tends to be stable; when the difference between the two values is less than 1mg KOH/g, the reaction is judged to be stable; and finally, removing the organic solvent in the reaction system by a reduced pressure distillation mode under the conditions of-0.09 MPa to-0.1 MPa and 40 ℃ to 150 ℃ to obtain the UV curing water-based resin. Preferably, the volume of the added amount of the solvent is 0.5 to 2 times of the volume of the A; the solvent is prepared by mixing water and an organic solvent according to a volume ratio of 1: (1-4), wherein the solvent is one of an ethanol/water mixed solvent, an acetone/water mixed solvent and an N-methylpyrrolidone/water mixed solvent; a is polyurethane modified acrylate, and B is amine alkyl sulfonate.
To further discuss the feasibility of the inventive concept, the discussion is made in terms of the following test examples and test data of the test examples:
test example 1
Adding 348.3g of toluene diisocyanate into a reaction bottle, heating to 60 ℃, starting stirring, slowly dropwise adding 600g of polyethylene glycol (PEG) 600 under the protection of nitrogen, continuing to perform heat preservation reaction after dropwise adding is finished, and stopping reaction when the measured-NCO value is close to the theoretical residual-NCO value and is stable to obtain 948.3g of monomer 1.
Adding 1185.2g of trimethylolpropane triacrylate into a reaction bottle, heating to 50 ℃, starting stirring, slowly dripping 122g of ethanolamine in the dark, continuing the heat preservation reaction after the dripping is finished, and stopping the reaction after no raw material peak is detected by a chromatograph to obtain monomer 2 of 1307.2 g.
Under the protection of argon and in the dark, 1307.2g of the monomer 2 is added into a reaction bottle, the temperature is raised to 60 ℃, stirring is started, 948.3g of the monomer 1 is slowly dripped, the heat preservation reaction is continued after the dripping is finished, no-NCO group is detected, the reaction is stopped, and the temperature is reduced to obtain 2255.5g of the polyurethane modified acrylate E6UV 8.
Adding 500g E6UV8 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 50.4g of ethylenediamine ethanesulfonic acid sodium salt (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W1-E6UV 8.
Test example 2
With reference to the preparation method and the compounding ratio of test example 1, urethane-modified acrylate E6UV8 was obtained.
Adding 500g E6UV8 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 67.2g of ethylenediamine ethanesulfonic acid sodium salt (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W2-E6UV 8.
Test example 3
With reference to the preparation method and the compounding ratio of test example 1, urethane-modified acrylate E6UV8 was obtained.
Adding 500g E6UV8 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 84g of ethylenediamine ethanesulfonic acid sodium salt (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W3-E6UV 8.
Test example 4
Adding 348.3g of toluene diisocyanate into a reaction bottle, heating to 60 ℃, starting stirring, slowly dripping 1000g of polyethylene glycol (PEG) 1000 under the protection of nitrogen, continuing heat preservation reaction after dripping is finished, and stopping reaction when the measured-NCO value is close to the theoretical residual-NCO value and is stable to obtain 1348.3g of monomer 3.
Adding 592.6g of trimethylolpropane triacrylate and 600.6g of tripropylene glycol diacrylate into a reaction bottle, heating to 50 ℃, starting stirring, slowly dripping 122g of ethanolamine in the dark, continuing the heat preservation reaction after finishing dripping, and stopping the reaction after no raw material peak is detected by chromatography to obtain 1315.2g of monomer 4.
Under the protection of argon and in the dark, 1315.2g of the monomer 4 is added into a reaction bottle, the temperature is raised to 60 ℃, stirring is started, 1348.3g of the monomer 3 is slowly dripped, the heat preservation reaction is continued after the dripping is finished, no-NCO group is detected, the reaction is stopped, and the temperature is reduced to obtain 2663.5g of the polyurethane modified acrylate E10UV 6.
Adding 500g E10UV6 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 42.8g of ethylenediamine ethanesulfonic acid sodium salt (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W1-E10UV 6.
Test example 5
With reference to the preparation method and the compounding ratio of test example 4, urethane-modified acrylate E10UV6 was obtained.
Adding 500g E10UV6 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 57.1g of ethylenediamine ethanesulfonic acid sodium salt (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W2-E10UV 6.
Test example 6
With reference to the preparation method and the compounding ratio of test example 4, urethane-modified acrylate E10UV6 was obtained.
Adding 500g E10UV6 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 71.4g of ethylenediamine ethanesulfonic acid sodium salt (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W3-E10UV 6.
Test example 7
Adding 348.3g of toluene diisocyanate into a reaction bottle, heating to 60 ℃, starting stirring, slowly dropwise adding 600g of polypropylene glycol PPG600 under the protection of nitrogen, continuing the heat preservation reaction after the dropwise adding is finished, and stopping the reaction to obtain 5g of monomer, 948.3g, wherein the measured-NCO value is close to the theoretical residual-NCO value and is stable.
Adding 1185.2g of trimethylolpropane triacrylate into a reaction bottle, heating to 50 ℃, starting stirring, slowly dripping 122g of ethanolamine in the dark, continuing the heat preservation reaction after the dripping is finished, and stopping the reaction after no raw material peak is detected by a chromatograph to obtain 6, 1307.2g of monomer.
Under the protection of argon and in the dark, 1307.2g of the monomer 6 is added into a reaction bottle, the temperature is raised to 60 ℃, stirring is started, 948.3g of the monomer 5 is slowly dripped, the heat preservation reaction is continued after the dripping is finished, no-NCO group is detected, the reaction is stopped, and the temperature is reduced to obtain 2255.5g of the polyurethane modified acrylate P6UV 8.
Adding 500g P6UV8 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 35.6g of sodium aminomethane sulfonate (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W1-P6UV 8.
Test example 8
With reference to the preparation method and the compounding ratio of test example 7, urethane-modified acrylate P6UV8 was obtained.
Adding 500g P6UV8 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 47.6g of sodium aminomethane sulfonate (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W2-P6UV 8.
Test example 9
With reference to the preparation method and the compounding ratio of test example 7, urethane-modified acrylate P6UV8 was obtained.
Adding 500g P6UV8 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 59.4g of sodium aminomethane sulfonate (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W3-P6UV 8.
Test example 10
Adding 348.3g of toluene diisocyanate into a reaction bottle, heating to 60 ℃, starting stirring, slowly dropwise adding 1000g of polyethylene glycol PPG1000 under the protection of nitrogen, continuing the heat preservation reaction after the dropwise adding is finished, and stopping the reaction to obtain 1348.3g of a monomer 7, wherein the measured-NCO value is close to the theoretical residual-NCO value and is stable.
Adding 592.6g of trimethylolpropane triacrylate and 600.6g of tripropylene glycol diacrylate into a reaction bottle, heating to 50 ℃, starting stirring, slowly dripping 122g of ethanolamine in the dark, continuing the heat preservation reaction after finishing dripping, and stopping the reaction after no raw material peak is detected by chromatography to obtain 8g of monomer 1315.2 g.
Under the protection of argon and in the dark, 1315.2g of the monomer 8 is added into a reaction bottle, the temperature is raised to 60 ℃, stirring is started, 1348.3g of the monomer 7 is slowly dripped, the heat preservation reaction is continued after the dripping is finished, no-NCO group is detected, the reaction is stopped, and the temperature is reduced to obtain 2663.5g of the polyurethane modified acrylate P10UV 6.
Adding 500g P10UV6 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 30.2g of sodium aminomethane sulfonate (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W1-P10UV 6.
Test example 11
With reference to the preparation method and the compounding ratio of test example 10, urethane-modified acrylate P10UV6 was obtained.
Adding 500g P10UV6 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 40.4g of sodium aminomethane sulfonate (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W2-P10UV 6.
Test example 12
With reference to the preparation method and the compounding ratio of test example 10, urethane-modified acrylate P10UV6 was obtained.
Adding 500g P10UV6 into an acetone/water mixed solvent, heating to 50-60 ℃, slowly dropwise adding 50.4g of sodium aminomethane sulfonate (50% aqueous solution) for reaction, detecting that no primary amine exists, and then carrying out reduced pressure distillation to remove acetone, thus obtaining the UV-cured water-based resin W3-P10UV 6.
Preferably, the tests of the test examples 1 to 3 are carried out by using the same batch of the UV-curable waterborne resin E6UV8, the tests of the test examples 4 to 6 are carried out by using the same batch of the UV-curable waterborne resin E10UV6, the tests of the test examples 7 to 9 are carried out by using the same batch of the UV-curable waterborne resin P6UV8, and the tests of the test examples 10 to 12 are carried out by using the same batch of the UV-curable waterborne resin P10UV 6.
The UV curable aqueous resin synthesized in the above test examples 1 to 12 was added with a certain amount of deionized water, and stirred at a high speed for 1 hour for emulsification to prepare a UV curable aqueous resin emulsion.
Weighing a certain amount of UV curing water-based resin emulsion, adding 1-3 wt% of initiator, stirring to dissolve the emulsion uniformly, respectively coating the emulsion on a tinplate and a PC-ABS plate, drying in a 65 ℃ oven for 20 minutes, taking out, cooling and curing by a UV machine.
And (3) carrying out a series of performance characterizations on the cured coating film: the adhesion of the coating film was tested according to GB 1720-79 (89); the hardness of the coating films was tested according to GB/T6739-; the flexibility of the coating film was tested according to GB/T1731-93. The emulsion solids content is determined according to GB 1725-79 (88); water absorption A certain amount of film was coated (weighed as M) according to GB/T1733-930) After 24 hours of soaking in deionized water, the solution was taken out, and after drying the surface water with filter paper, the weight was M1Water absorption rate ═ M1-M0)/M0×100％。
The data of the performance tests of the UV curable aqueous resins of test examples 1 to 12 are detailed in Table 1.
The invention also tests the performance of the UV-cured oleoresin E6UV8, E10UV6, P6UV8 and P10UV6 for comparison test, during the test, 50% acrylate reactive diluent is added in the paint formula, and the measured performance data of the UV-cured oleoresin are detailed in Table 2.
TABLE 1 UV-curable waterborne resin Properties
TABLE 2 UV-curable oleoresin Properties
As can be seen from the performance results of tables 1 and 2, the cured films of the UV-curable aqueous resins provided in test examples 1 to 12 of the present invention have high hardness, good adhesion, good flexibility, smooth appearance, and full paint film.
Compared with the UV curing oleoresin with the same main structure, the UV curing water-based resin has almost the same performance, but can replace the reactive diluent with water to regulate the viscosity,
the UV-curable water-based resin disclosed by the invention is good in emulsibility, and the emulsifying property and the water resistance of a cured film can be balanced by controlling the content of a hydrophilic group.
In conclusion, the invention provides the UV-curable water-based resin and the preparation method thereof. The UV-cured water-based resin is polyurethane modified acrylate UV resin, has hardness adjustability, and can adjust and control the hardness and flexibility of a cured film by changing the molecular weight of dihydric alcohol in raw materials for synthesizing the polyurethane modified acrylate; the curing agent has the characteristics of polyurethane and acrylate, and a curing film of the curing agent has high hardness, good adhesive force and flexibility, smooth appearance and full paint film; the emulsifying property of the resin and the water resistance of the cured film can be balanced by controlling the content of the hydrophilic group. When the UV-curable water-based resin is used as the main component of the UV-curable water-based paint, the fluidity of the paint can be adjusted by replacing an active diluent with water, so that the UV-curable water-based resin is environment-friendly, and the phenomenon of film curing shrinkage is improved. In addition, the UV-curable water-based paint also has the advantages of thin coating, easy cleaning of construction equipment and the like. The preparation method of the UV curing water-based resin is simple, has low requirements on equipment, and is easy to realize industrialization.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications of equivalent structures and equivalent processes, which are made by the present specification, or directly or indirectly applied to other related technical fields, are included in the scope of the present invention.
Claims (7)
1. The UV-curable water-based resin is characterized by being prepared by reacting A and B, wherein A is polyurethane modified acrylate, and B is amine alkyl sulfonate;
the structural formula of A is as follows:
wherein R is
R1Is composed of
R2Is composed of
R3Is composed of
R5Is composed of
R6Is composed of
R0Is H or Me, R4Is H or Me, R7Is H or Me, R8Is H or Me; n ranges from 2 to 20, n1The value range of (1) to (30), the value range of m is from 2 to (20), m1The value range of (a) is 1-30, and the value range of p is 1-30;
said B is composed of
wherein, the value range of x is 2-20, and Y+Is Na+And/or K+And/or NH4 +，Z+Is Na+And/or K+And/or NH4 +；
The reaction is a Michael addition reaction, and the molar weight ratio of the A to the B is 1: (0.5-2.0) carrying out the reaction.
2. The preparation method of the UV-curable water-based resin according to claim 1, wherein A and B are prepared as required, A is added into a reaction bottle, a solvent is added to dissolve A, the temperature is increased to 40-50 ℃, B is slowly dripped into the reaction bottle, after the dripping is finished, the heat preservation reaction is carried out until the reaction is finished, and the UV-curable water-based resin is obtained through post-treatment, wherein A is polyurethane modified acrylate, and B is amine alkyl sulfonate.
3. The method for producing a UV-curable aqueous resin according to claim 2, wherein the solvent is added in an amount of 0.5 to 2 times by volume based on the volume of the solvent a; the solvent is prepared by mixing water and an organic solvent according to a volume ratio of 1: and (1-4) are mixed according to the proportion.
4. The method for preparing a UV-curable aqueous resin according to claim 3, wherein the solvent is one of an ethanol/water mixed solvent, an acetone/water mixed solvent, and an N-methylpyrrolidone/water mixed solvent.
5. The method for preparing the UV-curable aqueous resin according to claim 4, wherein the reaction time of the incubation reaction is 24 to 48 hours.
6. The method for producing a UV-curable aqueous resin according to any one of claims 2 to 5, wherein the post-treatment is: removing the organic solvent by distillation under reduced pressure; the pressure of the reduced pressure distillation is-0.09 MPa to-0.1 MPa, and the temperature is 40-150 ℃.
7. The method for producing a UV-curable aqueous resin according to claim 6, wherein the primary amine value in the reaction system is detected, and when the primary amine value is less than 4mg KOH/g and tends to be stable, the reaction is judged to be completed.
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| CN112279992A (en) * | 2020-10-30 | 2021-01-29 | 深圳飞扬兴业科技有限公司 | UV-curable water-based resin and preparation method and application thereof |
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