CN111117554A - Ultraviolet light and moisture dual-curing polyurethane hot melt adhesive and preparation method thereof - Google Patents
Ultraviolet light and moisture dual-curing polyurethane hot melt adhesive and preparation method thereof Download PDFInfo
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
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- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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- 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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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
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- C08G18/6611—Compounds of groups C08G18/42, 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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- 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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Abstract
The invention relates to the field of hot melt adhesives, in particular to an ultraviolet light and moisture dual-curing hot melt adhesive and a preparation method thereof. The ultraviolet and moisture dual-curing polyurethane hot melt adhesive is prepared from the following raw materials in parts by weight: 20-50 parts of thermoplastic resin, 20-50 parts of polyester polyol, 5-35 parts of polyether polyol, 1-10 parts of trifunctional micromolecule polyol, 1-10 parts of hydroxyl-terminated acrylate or amino-terminated vinyl monomer, 2-20 parts of polyisocyanate, 0.1-1 part of catalyst, 1-5 parts of photoinitiator, 0.2-2 parts of silane coupling agent and 0.2-2 parts of defoaming agent. The invention prepares the polyurethane hot melt adhesive containing vinyl and isocyanate double reaction groups by reacting a vinyl functional monomer containing terminal hydroxyl or amino, polyester and polyether polyol with polyisocyanate. After the product is sized, the molecular weight of the vinyl polymer in the product is further increased through ultraviolet irradiation, and a high molecular weight reticular polymer is formed to generate pressure sensitivity and good initial adhesion strength, so that the function of quick positioning and pressure maintaining free is achieved.
Description
Technical Field
The invention relates to the field of hot melt adhesives, in particular to an ultraviolet light and moisture dual-curing hot melt adhesive and a preparation method thereof.
Background
The moisture curing type polyurethane hot melt adhesive is wide in application in the electronic assembly industry due to the fact that the curing mode is simple, the positioning speed is high, reworking is easy, and if a mobile phone frame is bonded with a TP screen, a middle frame is bonded with a decoration, intelligent bracelet cover plate glass is bonded with a watch shell in a sealing and waterproof mode, a control screen is bonded with a support frame in a vehicle-mounted mode, and the like.
Common moisture curing type polyurethane hot melt adhesive in the market at present can not use a large amount of high molecular weight thermoplastic resin because of the requirement of the sizing process on viscosity, so that the initial adhesion is low, the curing speed of the common moisture curing type polyurethane hot melt adhesive is limited by the moisture absorption speed and the reaction speed of isocyanate groups and moisture, the dependence on the humidity and the temperature of the environment is large, the adhesion is slowly increased, and the yield of a bonded sample piece is generally ensured by the pressure maintaining time from 1 to 8 small tests in precision assembly. The pressure maintaining process not only consumes an artificial field and reduces the production efficiency, but also occupies a large number of pressure maintaining jigs and increases the manufacturing cost.
Disclosure of Invention
In order to solve the problems, the invention introduces vinyl groups into a moisture curing polyurethane hot melt adhesive system, so that the hot melt adhesive can rapidly generate higher initial adhesion under the irradiation of ultraviolet light, thereby reducing the pressure maintaining time or achieving the pressure maintaining-free effect. The specific scheme is as follows:
an ultraviolet and moisture dual-curing polyurethane hot melt adhesive is prepared from the following raw materials in parts by weight: 20-50 parts of thermoplastic resin, 20-50 parts of polyester polyol, 5-35 parts of polyether polyol, 1-10 parts of trifunctional micromolecule polyol, 1-10 parts of hydroxyl-terminated acrylate or amino-terminated vinyl monomer, 2-20 parts of polyisocyanate, 0.1-1 part of catalyst, 1-5 parts of photoinitiator, 0.2-2 parts of silane coupling agent and 0.2-2 parts of defoaming agent.
Further, the thermoplastic resin comprises one or a mixture of more than two of thermoplastic polyurethane, thermoplastic acrylic resin and thermoplastic EVA resin;
further, the polyester polyol comprises one or more than two dehydrated condensation polymers of 1, 6-adipic acid, sebacic acid and 1, 4-butanediol, diethylene glycol, methyl propylene glycol, neopentyl glycol, 1, 5-pentanediol and 1, 6-hexanediol;
further, the molecular weight of the polyester polyol is 500-;
further, the polyether polyol comprises one or a mixture of more than two of PPG400, PPG600, PPG1000, PPG2000, PPG4000, PPG6000, PTMG1000 and PTMG 2000;
further, the trifunctional small molecular polyol comprises one or a mixture of more than two of trimethylolethane, trimethylolpropane and glycerol;
furthermore, the hydroxyl-terminated acrylic resin comprises one or a mixture of more than two of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and 4-hydroxy acrylate;
further, the amino-terminated vinyl resin comprises one or two of cyanuric acid and acrylamide;
further, the isocyanate comprises one or a mixture of more than two of TDI, HDI, MDI, HMDI and XDI;
further, the catalyst; comprises the following steps: dibutyl tin dilaurate, stannous octoate, triethylene diamine, 2- (2-dimethylamino-ethoxy) ethanol, N- (dimethylamino propyl) diisopropanolamine or a mixture of more than two of the dibutyl tin dilaurate, the stannous octoate, the triethylene diamine, the 2- (2-dimethylamino-ethoxy) ethanol and the N- (dimethylamino propyl) diisopropanolamine;
further, the photoinitiator comprises one or a mixture of more than two of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide (TPO), 2-hydroxy-2-methyl-phenyl acetone-1 (1173), 2-hydroxy-2-methyl-p-hydroxyethyl ether phenyl acetone-1 (2959) or 1-hydroxy-cyclohexyl monophenyl ketone (184);
further, the silane coupling agent comprises one or a mixture of more than two of A1160, KH560 and KH 580;
further, the defoaming agent comprises one or a mixture of more than two of BYK 066N, BYK 1790, BYK A535, BYK-067, BYK-051, BYK-077, BYK-352 and BYK-359;
a preparation method of ultraviolet and moisture dual-curing polyurethane hot melt adhesive comprises the following steps:
(1) stirring and dehydrating 20-50 parts of thermoplastic resin, 20-50 parts of polyester polyol, 5-35 parts of polyether polyol and 1-10 parts of trifunctional micromolecular polyol at 80-110 ℃ for 2 hours at 300 r/min.
(2) Cooling the dehydrated mixture obtained in the step (1) to 75-95 ℃, adding 1-10 parts of hydroxyl-terminated acrylate or amino-terminated vinyl monomer which is dehydrated in advance, 2-20 parts of polyisocyanate and 0.1-1 part of catalyst, and stirring and reacting for 1-3 hours under the nitrogen atmosphere to obtain a prepolymer;
(3) and (3) adding 1-5 parts of photoinitiator, 0.2-2 parts of silane coupling agent and 0.2-2 parts of defoaming agent into the prepolymer in the step (2), and stirring and defoaming under a vacuum state to obtain the polyurethane hot melt adhesive.
According to the invention, double bonds are introduced into a moisture curing reaction system through a hydroxyl-terminated acrylic monomer and an amino-containing vinyl monomer, so that ultraviolet curing is realized. Meanwhile, through the nucleophilic addition reaction of a trihydroxy compound, a hydroxyl-terminated acrylic monomer/amino-containing vinyl monomer and polyisocyanate, the functionality of vinyl and isocyanate in a macromolecular chain of a reaction product is improved, so that the rapid improvement of the ultraviolet light and moisture curing speed is realized, and higher binding power is kept.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to specific embodiments, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. 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
A preparation method of a UV pressure-sensitive/moisture dual-curing polyurethane hot melt adhesive comprises the following steps:
(1) 20 parts of thermoplastic EVA resin, 30 parts of 2000 molecular weight polybutylene adipate glycol, 20 parts of 1000 molecular weight PPG and 1 part of trimethylolethane are stirred and dehydrated for 2hrs at the temperature of 95 ℃ and under the vacuum condition of-0.1 MPa at the speed of 300 r/min.
(2) Cooling the dehydrated mixture obtained in the step (1) to 80 ℃, adding 5 parts of hydroxyethyl acrylate monomer with water removed in advance, 20 parts of polyisocyanate and 0.5 part of dibutyltin dilaurate, and stirring for reacting for 2hrs in a nitrogen atmosphere to obtain a prepolymer;
(3) and adding 2 parts of TPO photoinitiator, 1 part of A1160 and 0.4 part of BYK 066N into the prepolymer, and stirring and defoaming under the vacuum state of-0.1 MPa to obtain the polyurethane hot melt adhesive with ultraviolet/moisture dual curing.
Example 2
A preparation method of a UV pressure-sensitive/moisture dual-curing polyurethane hot melt adhesive comprises the following steps:
(1) 30 parts of thermoplastic acrylic resin, 30 parts of 2000 molecular weight poly (glutaric adipate) diol, 30 parts of 1000 molecular weight PPG and 2 parts of trimethylolpropane are stirred and dehydrated for 2hrs at the temperature of 95 ℃ and under the vacuum condition of-0.1 MPa at the speed of 300 r/min.
(2) Cooling the dehydrated mixture obtained in the step (1) to 80 ℃, adding 7 parts of hydroxyethyl methacrylate monomer with water removed in advance, 20 parts of HDI and 0.5 part of stannous octoate, and stirring for reaction for 2hrs in a nitrogen atmosphere to obtain a prepolymer;
(3) and 3 parts of TPO photoinitiator, 1 part of KH580 and 0.6 part of BYK 1790 are added into the prepolymer, and the mixture is stirred and defoamed under the vacuum state of-0.1 MPa to prepare the polyurethane hot melt adhesive with ultraviolet/moisture dual curing.
Example 3
A preparation method of a UV pressure-sensitive/moisture dual-curing polyurethane hot melt adhesive comprises the following steps:
(1) 40 parts of thermoplastic TPU resin, 30 parts of 2000 molecular weight poly (hexanediol adipate) glycol, 35 parts of 1000 molecular weight PPG and 3 parts of glycerol are stirred and dehydrated for 2hrs at the temperature of 95 ℃ and under the vacuum condition of-0.1 MPa at the speed of 300 r/min.
(2) And (2) cooling the dehydrated mixture obtained in the step (1) to 80 ℃, adding 9 parts of hydroxypropyl acrylate monomer with water removed in advance, 20 parts of MDI and 0.5 part of dibutyltin dilaurate, and stirring for reacting for 2hrs under the nitrogen atmosphere to obtain a prepolymer.
(3) 4 parts of 184 photoinitiator, 1 part of KH580 and 0.2 part of BYK A535 are added into the prepolymer, and the mixture is stirred and defoamed under the vacuum state of-0.1 MPa to prepare the polyurethane hot melt adhesive with ultraviolet/moisture dual curing.
Example 4
A preparation method of a UV pressure-sensitive/moisture dual-curing polyurethane hot melt adhesive comprises the following steps:
(1) 10 parts of thermoplastic EVA resin, 30 parts of acrylic resin, 30 parts of 2000 molecular weight hexanediol sebacate diol, 20 parts of 1000 molecular weight PPG, 10 parts of 1000 molecular weight PTMG and 4 parts of trimethylolethane are stirred and dehydrated for 2hrs at the temperature of 95 ℃ under the vacuum condition of-0.1 MPa by 300 r/min.
(2) Cooling the dehydrated mixture obtained in the step (1) to 80 ℃, adding 9 parts of 4-hydroxy acrylate with water removed in advance, 20 parts of HMDI and 0.5 part of dibutyltin dilaurate, and stirring for reacting for 2hrs in a nitrogen atmosphere to obtain prepolymer A;
(3) 4 parts of 1173 photoinitiator, 1 part of KH580 and 0.3 part of BYK 067 are added into the prepolymer A, and the mixture is stirred and defoamed under the vacuum state of-0.1 MPa to prepare the polyurethane hot melt adhesive with ultraviolet/moisture dual curing.
Example 5
A preparation method of a UV pressure-sensitive/moisture dual-curing polyurethane hot melt adhesive comprises the following steps:
(1) 15 parts of thermoplastic EVA resin, 25 parts of TPU resin, 30 parts of 2000 molecular weight neopentyl glycol adipate, 30 parts of 1000 molecular weight PPG, 15 parts of 1000 molecular weight PTMG and 5 parts of trimethylolethane are stirred and dehydrated for 2hrs at the temperature of 95 ℃ under the vacuum condition of-0.1 MPa by 300 r/min.
(2) Cooling the dehydrated mixture obtained in the step (1) to 80 ℃, adding 10 parts of acrylamide with pre-dehydrated, 20 parts of XDI and 0.5 part of dibutyltin dilaurate, and stirring for reaction for 2hrs under the nitrogen atmosphere to obtain prepolymer A;
(3) 4 parts of 184 photoinitiator, 1 part of KH560 and 1 part of BYK 051 are added into the prepolymer A, and the mixture is stirred and defoamed under the vacuum state of-0.1 MPa to prepare the polyurethane hot melt adhesive with ultraviolet/moisture dual curing.
Comparative example
The preparation method of the moisture curing polyurethane hot melt adhesive commonly used in the market comprises the following steps:
(1) 40 parts of thermoplastic TPU resin, 30 parts of 2000 molecular weight hexanediol adipate glycol and 35 parts of 1000 molecular weight PPG are stirred and dehydrated for 2hrs at the temperature of 95 ℃ and under the vacuum condition of-0.1 MPa at the speed of 300 r/min.
(2) Cooling the dehydrated mixture obtained in the step (1) to 80 ℃, adding 20 parts of MDI and 0.5 part of dibutyltin dilaurate, and stirring to react for 2hrs in a nitrogen atmosphere to obtain a prepolymer A;
(3) adding 1 part of KH580 and 0.2 part of BYK A535 into the prepolymer A, and stirring and defoaming under-0.1 MPa vacuum state to obtain the conventional moisture-cured polyurethane hot melt adhesive.
Samples of the UV and moisture dual cure polyurethane hot melt adhesives prepared in examples 1-5 and samples of the comparative moisture cure polyurethane hot melt adhesives were subjected to comparative tests for melt viscosity, initial strength, etc. as follows:
1. sample preparation and curing
(1) The sample preparation method comprises the following steps: examples 1-5 and comparative examples were used by dispensing at 110 ℃ and a thickness of 100. mu.m, each test piece was irradiated with a 365nm light source at 300mJ/cm2Bonding the test pieces after irradiation, pressing with 0.2MPa for 30s, respectively maintaining pressure and standing for 5min, testing shear strength for 1hr and 24 hr, preparing sample under each condition, testing in three groups, and averaging;
(2) curing conditions are as follows: the temperature was 25 ℃ and the humidity was 60% RH.
2. The results of the comparative tests of viscosity and adhesion properties are shown in Table 1 below;
table 1 examples 1-5 and comparative examples the results of the performance evaluation test
The test conditions were: temperature 25 ℃ and humidity 60% RH
As can be seen from Table 1, compared with the conventional moisture-curing polyurethane hot melt adhesive, the ultraviolet and moisture dual-curing polyurethane hot melt adhesive has the advantages that the viscosity difference is not large, but the initial bonding strength of 5min is improved by several times, even the strength is far higher than that of the conventional moisture-curing polyurethane hot melt adhesive after 1hr, the pressure maintaining time of the electronic assembly industry can be greatly shortened, the production efficiency is improved, and the jig cost is saved.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention in any way, and any simple modification, equivalent change and modification made to the above embodiment according to the technical spirit of the present invention are still within the scope of the technical solution of the present invention.
Claims (9)
1. The ultraviolet and moisture dual-curing polyurethane hot melt adhesive is characterized by being prepared from the following raw materials in parts by weight: 20-50 parts of thermoplastic resin, 20-50 parts of polyester polyol, 5-35 parts of polyether polyol, 1-10 parts of trifunctional micromolecule polyol, 1-10 parts of hydroxyl-terminated acrylate or amino-terminated vinyl monomer, 2-20 parts of polyisocyanate, 0.1-1 part of catalyst, 1-5 parts of photoinitiator, 0.2-2 parts of silane coupling agent and 0.2-2 parts of defoaming agent.
2. The polyurethane hot melt adhesive of claim 1, wherein the thermoplastic resin comprises one or a mixture of two or more of thermoplastic polyurethane, thermoplastic acrylic resin and thermoplastic EVA resin.
3. The polyurethane hot melt adhesive of claim 1, wherein the polyester polyol comprises one or more dehydrated condensation polymers of 1, 6-adipic acid with 1, 4-butanediol, diethylene glycol, methyl propylene glycol, neopentyl glycol, 1,5 pentanediol, and 1,6 hexanediol.
4. The polyurethane hot melt adhesive of claim 1, wherein the polyether polyol comprises one or a mixture of more than two of PPG400, PPG600, PPG1000, PPG2000, PPG4000, PPG6000, PTMG1000 and PTMG 2000.
5. The polyurethane hot melt adhesive of claim 1, wherein the trifunctional small-molecule polyol comprises one or a mixture of two or more of trimethylolethane, trimethylolpropane and glycerol.
6. The polyurethane hot melt adhesive according to claim 1, wherein the hydroxyl-terminated acrylic resin comprises one or a mixture of two or more of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and 4-hydroxy acrylate, and the amino-terminated vinyl resin comprises one or two of cyanuric acid and acrylamide.
7. The polyurethane hot melt adhesive of claim 1, wherein the catalyst comprises one or a mixture of two or more of dibutyltin dilaurate, stannous octoate, triethylene diamine, 2- (2-dimethylamino-ethoxy) ethanol, and N- (dimethylaminopropyl) diisopropanolamine.
8. The polyurethane hot melt adhesive according to claim 1, wherein the photoinitiator comprises one or a mixture of two or more of 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide (TPO), 2-hydroxy-2-methyl-phenylacetone-1 (1173), 2-hydroxy-2-methyl-p-hydroxyethyl ether-phenylpyruvate-1 (2959), or 1-hydroxy-cyclohexyl-monophenyl ketone (184).
9. A preparation method of ultraviolet and moisture dual-curing polyurethane hot melt adhesive is characterized by comprising the following steps:
(1) stirring and dehydrating 20-50 parts of thermoplastic resin, 20-50 parts of polyester polyol, 5-35 parts of polyether polyol and 1-10 parts of trifunctional micromolecular polyol at 80-110 ℃ for 2 hours at 300 r/min.
(2) Cooling the dehydrated mixture obtained in the step (1) to 75-95 ℃, adding 1-10 parts of hydroxyl-terminated acrylate or amino-terminated vinyl monomer which is dehydrated in advance, 2-20 parts of polyisocyanate and 0.1-1 part of catalyst, and stirring and reacting for 1-3 hours under the nitrogen atmosphere to obtain a prepolymer;
(3) and (3) adding 1-5 parts of photoinitiator, 0.2-2 parts of silane coupling agent and 0.2-2 parts of defoaming agent into the prepolymer in the step (2), and stirring and defoaming under a vacuum state to obtain the polyurethane hot melt adhesive.
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| CN201911420848.9A CN111117554B (en) | 2019-12-31 | 2019-12-31 | Ultraviolet light and moisture dual-curing polyurethane hot melt adhesive and preparation method thereof |
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Cited By (8)
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| CN112708354A (en) * | 2021-01-07 | 2021-04-27 | 镝普材料(深圳)有限公司 | Single-component ultraviolet and moisture dual-curing polyurethane hot melt adhesive and preparation method thereof |
| CN113088240A (en) * | 2021-05-25 | 2021-07-09 | 佛山禾邦新材料科技有限公司 | Reactive polyurethane hot melt adhesive and preparation method thereof |
| CN113337220A (en) * | 2021-06-16 | 2021-09-03 | 苏州环明电子科技有限公司 | High-resilience ultraviolet light and moisture dual-curing hot melt adhesive and preparation method thereof |
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| CN113881013A (en) * | 2021-10-27 | 2022-01-04 | 上海古原草科技有限公司 | Acrylic acid modified polyurethane epoxy toughening agent and preparation method thereof |
| CN114634789A (en) * | 2022-04-15 | 2022-06-17 | 韦尔通(厦门)科技股份有限公司 | Light/moisture dual-curing polyurethane hot melt adhesive composition with high initial bonding strength and preparation method thereof |
| CN114989773A (en) * | 2022-07-22 | 2022-09-02 | 上海美采新材料科技有限公司 | Polyurethane adhesive and preparation method thereof |
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