CN108949092B - Water-based UV (ultraviolet) curing adhesive and preparation method and application thereof - Google Patents
Water-based UV (ultraviolet) curing adhesive and preparation method and application thereof Download PDFInfo
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- CN108949092B CN108949092B CN201810831387.3A CN201810831387A CN108949092B CN 108949092 B CN108949092 B CN 108949092B CN 201810831387 A CN201810831387 A CN 201810831387A CN 108949092 B CN108949092 B CN 108949092B
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- 239000000853 adhesive Substances 0.000 title claims abstract description 55
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000004814 polyurethane Substances 0.000 claims abstract description 33
- 229920002635 polyurethane Polymers 0.000 claims abstract description 33
- 125000002091 cationic group Chemical group 0.000 claims abstract description 24
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 19
- 238000003848 UV Light-Curing Methods 0.000 claims abstract description 19
- 238000003756 stirring Methods 0.000 claims abstract description 17
- 239000013067 intermediate product Substances 0.000 claims abstract description 10
- 239000008367 deionised water Substances 0.000 claims abstract description 8
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 8
- 239000002562 thickening agent Substances 0.000 claims abstract description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 amine compound Chemical class 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 8
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- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 claims description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004310 lactic acid Substances 0.000 claims description 6
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- 239000005056 polyisocyanate Substances 0.000 claims description 6
- 229920001228 polyisocyanate Polymers 0.000 claims description 6
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- 239000003549 soybean oil Substances 0.000 claims description 5
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- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 4
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 4
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- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
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- 239000004417 polycarbonate Substances 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- UEEJHVSXFDXPFK-UHFFFAOYSA-O N-dimethylethanolamine Chemical compound C[NH+](C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-O 0.000 claims description 3
- 239000004359 castor oil Substances 0.000 claims description 3
- 235000019438 castor oil Nutrition 0.000 claims description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- YLYIXDZITBMCIW-UHFFFAOYSA-N n-hydroxy-n-phenylbenzamide Chemical compound C=1C=CC=CC=1N(O)C(=O)C1=CC=CC=C1 YLYIXDZITBMCIW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 4
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- 238000000576 coating method Methods 0.000 description 4
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- RTJGBIGSNVJSDM-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(C(C)(C)N=C=O)=C1 RTJGBIGSNVJSDM-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- KKBYLNUMPXZUGE-UHFFFAOYSA-K di(decanoyloxy)bismuthanyl decanoate Chemical compound [Bi+3].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O KKBYLNUMPXZUGE-UHFFFAOYSA-K 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
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- 239000001809 ammonium phosphatide Substances 0.000 description 1
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- 238000005260 corrosion Methods 0.000 description 1
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
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- 229920000728 polyester Polymers 0.000 description 1
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- 238000007639 printing Methods 0.000 description 1
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- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
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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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- 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
- C08G18/4833—Polyethers containing oxyethylene units
-
- 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
- C08G18/58—Epoxy resins
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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
- C08G18/65—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
- C08G18/6629—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
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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
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- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
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- C08G18/6644—Compounds of group C08G18/42 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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- 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
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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
- 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
- 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
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- 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
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a water-based UV curing adhesive, a preparation method and application thereof, wherein the preparation method comprises the following steps: (1) preparing an intermediate product with 3-6-NCO isocyanate groups; (2) preparing cationic waterborne UV polyurethane acrylate resin; (3) preparation of aqueous UV-curing adhesive: adding deionized water and cationic waterborne UV polyurethane acrylate resin into dispersing equipment, adjusting the stirring speed to 800-4000 r/min, dispersing for 1-3 h, adding a thickening agent, and continuously stirring for 0.5-2 h to obtain the waterborne UV curing adhesive. The product of the invention has the characteristics of environmental protection, strong adhesive force and convenient use, and can be widely applied to the fields of soles, automotive interiors, electronic products, children toys and the like.
Description
Technical Field
The invention relates to a water-based UV curing adhesive, a preparation method and application thereof, in particular to a cationic water-based UV polyurethane acrylate resin adhesive, belonging to the technical field of adhesives and coatings.
Background
The polyurethane has excellent mechanical property, adjustable molecular structure and good mechanical property, and can be widely applied to the fields of coatings, elastomers, printing ink, adhesives and the like. The polyurethane adhesives are various in variety, but most of the polyurethane adhesives on the market at present are solvent-based, are diluted by organic solvents, even use forbidden solvents such as toluene, benzene and the like, and have good bonding effect, but the disadvantages and hazards brought by the organic solvents are obvious, such as difficulty in safe storage, air pollution, harm to human health, waste of resources and the like.
Chinese patent CN107129786A discloses a preparation method of a polyurethane adhesive, isocyanate reacts with polyester in a catalyst and a solvent, and then a dispersant is added for dispersion to obtain the polyurethane adhesive, which has good bonding effect, but uses a large amount of organic solvent, even toluene with extremely high toxicity, and has high VOC; chinese patent CN101508785A discloses a dispersion adhesive, relating to an aqueous dispersion adhesive of a mixture of aqueous polyurethane or a polyurethane-urea dispersion system, which has the defects of complicated steps, unstable dispersion prepared by a partial method and poor bonding effect.
In particular, development of aqueous polyurethane resin and downstream application technology is proposed in "guidance for development of key industrial common technology" (2017) issued by the ministry of industry and informatization. Aiming at the problem that the existing polyurethane adhesive is in the water-based polyurethane resin technology advocated in key points, the cationic water-based UV polyurethane acrylate has the advantages of no toxicity, no odor, energy conservation, long-term storage and quick curing.
Disclosure of Invention
The invention is developed aiming at the problems that the existing adhesive containing organic solvent is toxic and has strong odor, and the common cationic water-based adhesive has poor adhesive force.
The technical scheme of the invention is to provide a preparation method of a water-based UV-curable adhesive, which comprises the following steps:
(1) preparing an intermediate product with 3-6 isocyanate groups (-NCO): adding polyisocyanate, polyol compounds and a catalyst into a reaction device, uniformly mixing, heating to 60-100 ℃, and reacting for 1-4 h to obtain an intermediate product with 3-6 isocyanate groups;
(2) preparing cationic water-based UV polyurethane acrylate resin: adding an intermediate product with 3-6 isocyanate groups, an amine compound, a hydroxyl-terminated vinyl compound and an epoxy compound into a reaction device at 50-90 ℃ to react for 5-8 h, removing excess organic solvent by reduced pressure distillation, dropwise adding an organic acid and a photoinitiator, and stirring for 1-3 h to obtain a cationic waterborne UV polyurethane acrylate resin;
(3) preparation of aqueous UV-curing adhesive: adding deionized water and cationic aqueous UV polyurethane acrylate resin into dispersing equipment, adjusting the stirring speed to 800-4000 r/min, dispersing for 1-3 h, adding a thickening agent, and continuously stirring for 0.5-2 h to obtain the aqueous UV curing adhesive.
Preferably, the various raw materials for preparing the cationic water-based UV polyurethane acrylate resin and the mass percentages thereof are respectively as follows:
25-40% of polyisocyanate, 30-50% of polyol compound, 0.5-2% of catalyst, 3-7% of amine compound, 7.5-15% of hydroxyl-terminated vinyl compound, 1-3% of epoxy compound, 3-5% of organic acid and 2-6% of photoinitiator.
Preferably, the various raw materials for preparing the water-based UV curing adhesive and the mass percentages thereof are as follows: 9.9 to 49.9 percent of cationic water-based UV polyurethane acrylate resin, 50 to 90 percent of deionized water and 0.1 to 0.5 percent of thickening agent.
Preferably, the polyisocyanate is one or more of isophorone diisocyanate (IPDI), tetramethylxylylene diisocyanate (TMXDI), diphenylmethane diisocyanate (MDI), and Toluene Diisocyanate (TDI).
Preferably, the polyalcohol compound is one or more of polycaprolactone dihydric alcohol, polycaprolactone trihydric alcohol, polycarbonate dihydric alcohol, glycerol, trimethylolpropane, polybutylene adipate, polyethylene glycol and polypropylene glycol; the average molecular weight of the polyalcohol compound is 50-8000.
Preferably, the amine compound is one or more of N-methyldiethanolamine, N-dimethylethanolamine, diethanolamine, triethylamine, N-benzoylphenylhydroxylamine and the like.
Preferably, the hydroxyl-terminated vinyl compound is one or more of hydroxyethyl acrylate, beta-hydroxyethyl methacrylate, hydroxypropyl acrylate and pentaerythritol triacrylate; the organic acid is one or two of acetic acid and lactic acid.
Preferably, the epoxy compound is one or more of epoxy resin E-44, epoxy resin E-51, epoxidized soybean oil and epoxidized castor oil.
The solid content of the water-based UV curing adhesive obtained by the preparation method is 30-60%, the pH value is 4.2-6.3, and the viscosity is 1000-75000 cPa.
And coating the water-based UV curing adhesive on an interface to be bonded, baking for 5-10 min at the temperature of 75-85 ℃, and then putting the interface into ultraviolet curing equipment for curing for 1-3 min to bond.
The invention provides a preparation method of a cationic waterborne UV polyurethane acrylate adhesive, which is characterized in that an intermediate product with 3-6-NCO groups is prepared through a high-molecular grafting reaction, and the functionality can be effectively improved; and then, by utilizing the reaction of-NCO and-OH, the defects of weak adhesive force of the cationic aqueous UV polyurethane adhesive are overcome by using the end capping of hydroxyl-terminated acrylate, amine compounds and epoxy resin.
The reaction solvent is selected from the following organic solvents: one or more of ethyl acetate, butyl acetate, propylene glycol butyl ether and acetone, and the dosage of the organic solvent during synthesis is 10-20% of the total mass of the resin. The catalyst is dibutyl tin dilaurate or bismuth decanoate.
Compared with the prior art, the invention has the following beneficial effects:
(1) the waterborne UV curing adhesive disclosed by the invention is prepared by synthesizing an intermediate product with 3-6-NCO groups, and the functional degree of the intermediate product is high, so that the adhesive force of the cationic waterborne UV polyurethane acrylate adhesive is greatly improved.
(2) The water-based UV curing water-based UV adhesive has good storage stability, can be stored for one year under natural conditions, and is convenient to store and transport.
(3) The water-based UV curing adhesive is a water-based UV adhesive, has good biocompatibility, is quick to adhere, is non-toxic and environment-friendly, and saves energy.
(4) The water-based UV curing adhesive also has a certain antibacterial effect.
The product of the invention can be directly applied to the bonding field and can be widely applied to the fields of soles, automotive interiors, electronic products, children toys and the like.
Drawings
FIG. 1 is an infrared spectrum of the molecular structure of the aqueous UV-curable adhesive in example 1 provided by the present invention.
FIG. 2 is a particle size distribution plot of a dispersion of an aqueous UV-curable adhesive in example 1 provided by the present invention.
Fig. 3 is an appearance picture of a cationic aqueous UV urethane acrylate resin and a prepared adhesive in example 3 provided by the present invention (resin on the left side, adhesive on the right side).
Detailed Description
For a better understanding of the present invention, the invention is further illustrated in detail below with reference to the examples, all of which are commercially available and the catalyst is bismuth decanoate.
Example 1
Preparing the following raw materials in percentage by mass: raw material components of the resin and mass percentages (wt.%):
26% of isophorone diisocyanate, 7% of glycerol, 20% of polycarbonate diol, 18% of polycaprolactone triol, 6.5% of lactic acid, 0.5% of catalyst, 2.7% of pentaerythritol triacrylate, 11.3% of beta-hydroxyethyl methacrylate, 4% of N-methyldiethanolamine, epoxy resin E-442% and 2% of photoinitiator.
Uniformly mixing the isophorone diisocyanate, the polycaprolactone triol, the polycarbonate diol, the glycerol, the catalyst and the solvent in the proportion in a reactor provided with a reflux device, a heating device and a stirring device. Heating to 90-100 ℃ for mixing reaction, continuing to react for 2h at constant temperature, reducing the temperature, adding the pentaerythritol triacrylate, the beta-hydroxyethyl methacrylate and the N-methyldiethanolamine in the proportion for reaction for 6h at 70-80 ℃, removing redundant amines and organic solvents by reduced pressure distillation, dropwise adding the lactic acid and the photoinitiator into a reaction device, and stirring for 2h after dropwise addition is finished to obtain the aqueous UV polyurethane acrylate resin with the amine value of 37.1 mgKOH/g. And then, adding a certain amount of resin into deionized water for high-speed dispersion, adjusting the solid content to 21%, adding 0.1% of thickening agent when the dispersion is transparent with blue light, and continuously stirring for 1h to obtain the cationic water-based UV polyurethane acrylate adhesive.
The infrared spectrum of cationic water-based UV polyurethane acrylate resin is shown in figure 1, wherein the infrared spectrum is 3500cm-1No obvious stretching vibration of O-H is found, which indicates that most of-OH is completely reacted; 3736cm-12988cm, as a telescopic shock absorption peak of-NH-)-1、2843cm-1Are respectively-CH3、-CH2Characteristic absorption peak of functional group, 2266cm-1In order to find no obvious characteristic absorption peak of the-NCO group, the-NCO is completely reacted; 1714cm-1Is a C-O-C asymmetric stretching vibration characteristic absorption peak in an ester bond, and the formation of the urethane bond is shown above. 1640cm-1Characteristic absorption of stretching vibration of C ═ C skeleton under alkenyl group, and 800cm-1The stretching vibration peak of C-H on the C ═ C double bond appears, which indicates that the vinyl monomer is successfully terminated, and 1100cm-1The stretching vibration of the C-N bond in the N-methyldiethanolamine shows that the synthesis of the cationic aqueous UV polyurethane acrylate is successful.
FIG. 2 is a particle size distribution diagram of a dispersion formed by emulsifying the aqueous urethane acrylate resin of example 1 of the present invention, and it can be seen from the diagram that the average particle size is 45.32nm, which illustrates that the aqueous pendant ammonium salt UV urethane acrylate cationic resin prepared by the example of the present invention has good emulsifying ability.
Example 2
The preparation method comprises the following steps of (1) preparing raw materials according to the mass percent of the total materials, wherein the raw materials of the resin comprise the following components in percentage by mass:
37% of tetramethylxylylene diisocyanate, 10% of polycaprolactone triol, 23% of polyethylene glycol, 2.5% of acetic acid, 2.5% of lactic acid, 1% of catalyst, 3.7% of pentaerythritol triacrylate, 10.3% of hydroxyethyl acrylate, 4% of diethanolamine, 5% of photoinitiator, 0.5% of epoxidized soybean oil and 0.5% of epoxidized castor oil.
In a reactor with reflux, heating and stirring devices, the tetramethyl xylylene diisocyanate, the polycaprolactone triol, the polyethylene glycol, the catalyst and the solvent in the proportion are uniformly mixed. Heating to 90-100 ℃ for mixing reaction, continuing to react for 4h at constant temperature, reducing the temperature, adding the pentaerythritol triacrylate, the hydroxyethyl acrylate and the diethanolamine in the proportion for reaction for 7h at the temperature of 50-60 ℃, removing redundant amines and organic solvents by reduced pressure distillation, dropwise adding the lactic acid and the photoinitiator into a reaction device, and stirring for 2h after dropwise addition is finished to obtain the aqueous UV polyurethane acrylate resin with the amine value of 30.4 mgKOH/g. And then, adding a certain amount of resin into deionized water for high-speed dispersion, adjusting the solid content to 35%, adding 0.2% of thickening agent when the dispersion is transparent with blue light, and continuously stirring for 1h to obtain the cationic water-based UV polyurethane acrylate adhesive. The joints were bonded using the polyurethane adhesive of example 2 using the method of GB/T7124-1986, respectively, and the bond strength was determined and the corrosion resistance of the adhesive was tested with reference to relevant standards for coating testing, with the results shown in Table 1:
example 3
The preparation method comprises the following steps of (1) preparing raw materials according to the mass percent of the total materials, wherein the raw materials of the resin comprise the following components in percentage by mass:
18% of isophorone diisocyanate, 9.5% of 3-isopropyl-dimethylbenzyl isocyanate, 8.5% of diphenylmethane diisocyanate, 2.5% of N-methyldiethanolamine, 2.7% of N, N-dimethylethanolamine, 23.6% of polypropylene glycol, 13% of polycaprolactone triol, 6% of acetic acid, 0.7% of catalyst, 7% of pentaerythritol triacrylate, 2% of hydroxypropyl acrylate, 0.5% of hydroxypropyl methacrylate, E-441% of epoxy resin, 1% of epoxidized soybean oil and 4% of photoinitiator.
Uniformly mixing the diphenylmethane diisocyanate, the isophorone diisocyanate, the 3-isopropyl-dimethyl benzyl isocyanate, the polycaprolactone triol, the polypropylene glycol, the catalyst and the solvent in the proportion in a reactor provided with a reflux device, a heating device and a stirring device. Heating to 90-100 ℃ for mixed reaction, continuously reacting for 4h at constant temperature, reducing the temperature to 70 DEG C～At 80 ℃ conditionAdding pentaerythritol triacrylate, hydroxypropyl acrylate, N-methyldiethanolamine, N-dimethylethanolamine, hydroxypropyl methacrylate, epoxy resin E-44 and epoxy soybean oil in the proportion for reacting for 6 hours, removing redundant amines and organic solvents by reduced pressure distillation, dropwise adding acetic acid and a photoinitiator into a reaction device, and stirring for 2 hours after dropwise adding is finished to obtain the water-based UV polyurethane acrylate resin with the amine value of 35.8 mgKOH/g. And then, adding a certain amount of resin into deionized water for high-speed dispersion, adjusting the solid content to 32%, adding 0.5% of thickening agent when the dispersion is transparent with blue light, and continuously stirring for 1h to obtain the cationic water-based UV polyurethane acrylate adhesive. FIG. 3 shows the resin and adhesive prepared in example 3.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (9)
1. A preparation method of a water-based UV curing adhesive is characterized by comprising the following steps:
(1) preparing cationic water-based UV polyurethane acrylate resin: adding an intermediate product with 3-6 isocyanate groups, an amine compound, a hydroxyl-terminated vinyl compound and an epoxy compound into a reaction device at 50-90 ℃ to react for 5-8 h, removing excess organic solvent by reduced pressure distillation, dropwise adding an organic acid and a photoinitiator, and stirring for 1-3 h to obtain a cationic waterborne UV polyurethane acrylate resin;
the preparation method of the intermediate product with 3-6 isocyanate groups comprises the following steps: adding polyisocyanate, a polyol compound and a catalyst into a reaction device, uniformly mixing, heating to 60-100 ℃, and reacting for 1-4 h to obtain an intermediate product with 3-6 isocyanate groups;
(2) preparation of aqueous UV-curing adhesive: adding deionized water and cationic aqueous UV polyurethane acrylate resin into dispersing equipment, adjusting the stirring speed to 800-4000 r/min, dispersing for 1-3 h, adding a thickening agent, and continuously stirring for 0.5-2 h to obtain an aqueous UV curing adhesive;
the polyalcohol compounds are 2 or more than 2 of polycaprolactone dihydric alcohol, polycaprolactone trihydric alcohol, polycarbonate dihydric alcohol, glycerol, trimethylolpropane, polybutylene adipate, polyethylene glycol and polypropylene glycol; the polyol compound comprises at least one dihydric alcohol and at least one trihydric alcohol; the average molecular weight of the polyalcohol compound is 50-8000;
the weight percentage of the trihydric alcohol is 10%, 13% and 25%.
2. The preparation method according to claim 1, wherein the cationic aqueous UV polyurethane acrylate resin is prepared from the following raw materials in percentage by mass:
25-40% of polyisocyanate, 30-50% of polyol compound, 0.5-2% of catalyst, 3-7% of amine compound, 7.5-15% of hydroxyl-terminated vinyl compound, 1-3% of epoxy compound, 3-5% of organic acid and 2-6% of photoinitiator.
3. The preparation method of claim 1, wherein the raw materials for preparing the aqueous UV-curable adhesive and the mass percentages thereof are as follows: 9.9-49.9% of cationic water-based UV polyurethane acrylate resin, 50-90% of deionized water and 0.1-0.5% of thickening agent.
4. The method of claim 1, wherein the polyisocyanate is one or more of isophorone diisocyanate (IPDI), tetramethylxylylene diisocyanate (TMXDI), diphenylmethane diisocyanate (MDI), and Toluene Diisocyanate (TDI).
5. The method according to claim 1, wherein the amine compound is one or more selected from the group consisting of N-methyldiethanolamine, N-dimethylethanolamine, diethanolamine, triethylamine, and N-benzoylphenylhydroxylamine.
6. The preparation method according to claim 1, wherein the hydroxyl-terminated vinyl compound is one or more of hydroxyethyl acrylate, beta-hydroxyethyl methacrylate, hydroxypropyl acrylate and pentaerythritol triacrylate; the organic acid is one or two of acetic acid and lactic acid.
7. The method of claim 1, wherein the epoxy compound is one or more of epoxy resin E-44, epoxy resin E-51, epoxidized soybean oil, and epoxidized castor oil.
8. The aqueous UV-curable adhesive obtained by the preparation method of any one of claims 1 to 7, wherein the solid content in the aqueous UV-curable adhesive is 30 to 60%, the pH is 4.2 to 6.3, and the viscosity is 1000 to 75000 cPa.
9. The application of the aqueous UV curing adhesive obtained by the preparation method of any one of claims 1 to 7 or the aqueous UV curing adhesive of claim 8 is characterized in that the aqueous UV curing adhesive is coated on an interface to be bonded, baked at the temperature of 75-85 ℃ for 5-10 min, and then placed in an ultraviolet curing device to be cured for 1-3 min to bond.
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Denomination of invention: A water-based UV curing adhesive and its preparation method and application Granted publication date: 20210507 Pledgee: Zhejiang Longyou rural commercial bank Limited by Share Ltd. Pledgor: LONGYOU HENGYU SHOES CO.,LTD. Registration number: Y2024980009078 |
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