CN113388087A - Waterborne polyurethane resin and preparation method thereof, and waterborne adhesive and application thereof - Google Patents
Waterborne polyurethane resin and preparation method thereof, and waterborne adhesive and application thereof Download PDFInfo
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- CN113388087A CN113388087A CN202010176982.5A CN202010176982A CN113388087A CN 113388087 A CN113388087 A CN 113388087A CN 202010176982 A CN202010176982 A CN 202010176982A CN 113388087 A CN113388087 A CN 113388087A
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- 229920005749 polyurethane resin Polymers 0.000 title claims abstract description 26
- 239000000853 adhesive Substances 0.000 title claims abstract description 23
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 64
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 34
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 34
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 22
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000005058 Isophorone diisocyanate Substances 0.000 claims abstract description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 17
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 17
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000008367 deionised water Substances 0.000 claims abstract description 17
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 17
- 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 abstract description 17
- 229920001610 polycaprolactone Polymers 0.000 claims abstract description 17
- 239000004632 polycaprolactone Substances 0.000 claims abstract description 17
- 229920000909 polytetrahydrofuran Polymers 0.000 claims abstract description 17
- 239000002994 raw material Substances 0.000 claims abstract description 17
- 150000002009 diols Chemical class 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 238000001816 cooling Methods 0.000 claims description 20
- 239000006185 dispersion Substances 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- 238000004321 preservation Methods 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical group CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000007789 sealing Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 239000004744 fabric Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 238000004806 packaging method and process Methods 0.000 claims description 5
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 239000002518 antifoaming agent Substances 0.000 claims description 3
- 239000003899 bactericide agent Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 239000000080 wetting agent Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims 1
- 244000144992 flock Species 0.000 claims 1
- 239000003607 modifier Substances 0.000 claims 1
- 238000000034 method Methods 0.000 description 5
- 239000003292 glue Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000003475 lamination Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- HQVFKSDWNYVAQD-UHFFFAOYSA-N n-hydroxyprop-2-enamide Chemical compound ONC(=O)C=C HQVFKSDWNYVAQD-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- 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
-
- 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
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6607—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
-
- 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
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6614—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 C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6618—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 C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
-
- 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
- C08G18/6625—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/34
-
- 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
-
- 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
- C09J175/06—Polyurethanes from polyesters
-
- 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
- C09J175/08—Polyurethanes from polyethers
Abstract
The invention provides a waterborne polyurethane resin and a preparation method thereof, a waterborne adhesive and application thereof, wherein the waterborne polyurethane resin is prepared from the following raw materials in parts by weight: isophorone diisocyanate: 38-42 parts of polytetrahydrofuran ether glycol (Mn ═ 2000): 38-42 parts of polycaprolactone diol (Mn ═ 2000): 38-42 parts of N-methylpyrrolidone: 19-21 parts of 1, 4-butanediol: 6.5-7.5 parts of dimethylolbutyric acid: 5.5-6.5 parts of organic bismuth catalyst: 0.09-0.11 parts of acetone: 125-135 parts of N, N-dimethylethanolamine: 3.3-3.5 parts of deionized water: 143-153 parts, 1, 6-hexanediamine: 2.1 to 2.3 portions. The waterborne polyurethane resin, the preparation method thereof, the waterborne adhesive and the application thereof can meet the requirements of tensile property and elongation percentage.
Description
Technical Field
The invention relates to the technical field of aqueous adhesives, in particular to an aqueous polyurethane resin and a preparation method thereof, an aqueous adhesive and application thereof.
Background
The method is a general production mode of the current flocking products, and the base material for the automobile sealing strip flocking belt mainly comprises films of PVC, TPV, EPDM and the like, and the water-based adhesive mainly adopts polyacrylate emulsion.
As described in patent CN 109337008A, isooctyl acrylate, ethyl acrylate, N-butyl acrylate, methyl methacrylate, cross-linked monomer N-hydroxy acrylamide, etc. are used to perform emulsion polymerization, and a water-based flocking adhesive with certain wear resistance and structural strength is prepared by matching soft and hard monomers.
However, the flexibility and tensile strength of the glue are poor due to the weak carbon-carbon bond energy caused by the polymerization of the acrylic monomer, the glue is easy to stretch after being heated in the online hot laminating process, and the tensile property and elongation of the product cannot meet the requirements of automobile sealing strip flocking products with high requirements.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide an aqueous polyurethane resin, a preparation method thereof, an aqueous adhesive and an application thereof, which can meet the requirements of tensile property and elongation.
The technical scheme of the invention is realized as follows:
the waterborne polyurethane resin is prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 38 to 42 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 38 to 42 portions of
Polycaprolactone diol (Mn ═ 2000): 38 to 42 portions of
N-methylpyrrolidone: 19 to 21 portions of
1, 4-butanediol: 6.5 to 7.5 portions of
Dimethylolbutyric acid: 5.5 to 6.5 portions of
Organic bismuth catalyst: 0.09 to 0.11 portion
Acetone: 125 portion
N, N-dimethylethanolamine: 3.3 to 3.5 portions
Deionized water: 143 portions 153-
1, 6-hexamethylenediamine: 2.1 to 2.3 portions.
Preferably, the feed is prepared from the following raw materials in parts by weight:
the feed is prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 38 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 38 portions of
Polycaprolactone diol (Mn ═ 2000): 38 portions of
N-methylpyrrolidone: 19-part(s)
1, 4-butanediol: 6.5 parts of
Dimethylolbutyric acid: 5.5 parts of
Organic bismuth catalyst: 0.09 part
Acetone: 125 portions of
N, N-dimethylethanolamine: 3.3 parts of
Deionized water: 143 portions of
1, 6-hexamethylenediamine: 2.1 parts.
Preferably, the feed is prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 42 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 42 portions of
Polycaprolactone diol (Mn ═ 2000): 42 portions of
N-methylpyrrolidone: 21 portions of
1, 4-butanediol: 7.5 parts of
Dimethylolbutyric acid: 6.5 parts of
Organic bismuth catalyst: 0.11 portion
Acetone: 135 portions of
N, N-dimethylethanolamine: 3.5 parts of
Deionized water: 153 portions of
1, 6-hexamethylenediamine: 2.3 parts.
Preferably, the feed is prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 40 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 40 portions of
Polycaprolactone diol (Mn ═ 2000): 40 portions of
N-methylpyrrolidone: 20 portions of
1, 4-butanediol: 7 portions of
Dimethylolbutyric acid: 6 portions of
Organic bismuth catalyst: 0.1 part
Acetone: 130 portions of
N, N-dimethylethanolamine: 3.4 parts of
Deionized water: 148 portions of
1, 6-hexamethylenediamine: 2.2 parts.
A preparation method of aqueous polyurethane resin comprises the following steps:
s1, adding polytetrahydrofuran ether glycol and polycaprolactone glycol into the reaction kettle, stirring and melting, adding isophorone diisocyanate, heating to 80 ℃, and reacting for 90 minutes;
s2, cooling to 60 ℃, adding N-methylpyrrolidone and 1, 4-butanediol, stirring uniformly, heating to 80 ℃, continuing to perform heat preservation reaction for 60 minutes, adding dimethylolbutyric acid and an organic bismuth catalyst, and continuing to perform heat preservation reaction until the NCO content reaches a design value;
s3, cooling after the reaction is finished, slowly adding metered acetone, cooling to about 40 ℃ after the acetone is added, adding N, N-dimethylethanolamine, increasing the stirring speed, and adding deionized water for high-speed dispersion; after the dispersion is finished, adding 1, 6-hexamethylene diamine for chain extension reaction;
and S4, heating to 60 ℃, decompressing the dispersion liquid to remove acetone, cooling to about 40 ℃ when the acetone is completely removed, filtering by using 200-mesh filter cloth, and packaging.
The water-based adhesive is prepared from the following raw materials in parts by weight:
the aqueous polyurethane resin described above: 90 portions of
Dispersing agent: 0.5 portion
Wetting agent: 0.3 part
Leveling agent: 0.3 part
Drying and regulating agent: 3 portions of
Defoaming agent: 0.5 portion
Water: 4.0 part
Thickening agent: 1 part of
And (3) bactericide: 0.4.
preferably, the drying regulator is propylene glycol and/or glycerol.
The application of the water-based adhesive is characterized in that the water-based adhesive is used for bonding the flocked fluff of the automobile sealing strip and the substrate film.
According to the waterborne polyurethane resin, the preparation method thereof, the waterborne adhesive and the application thereof, the waterborne polyurethane resin with high solid content (more than or equal to 50%) is used as the main material of the adhesive, and the problems of tensile strength of the product in the hot bonding process are solved due to the large bond energy of the urethane bond of the polyurethane and the large cohesive energy of glue molecules, so that the adhesive force to a substrate film and the wear resistance of the product can meet the performance requirements of automobile sealing strip products.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all 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
The waterborne polyurethane resin is prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 38 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 38 portions of
Polycaprolactone diol (Mn ═ 2000): 38 portions of
N-methylpyrrolidone: 19-part(s)
1, 4-butanediol: 6.5 parts of
Dimethylolbutyric acid: 5.5 parts of
Organic bismuth catalyst: 0.09 part
Acetone: 125 portions of
N, N-dimethylethanolamine: 3.3 parts of
Deionized water: 143 portions of
1, 6-hexamethylenediamine: 2.1 parts.
The preparation method of the waterborne polyurethane resin comprises the following steps:
s1, adding polytetrahydrofuran ether glycol and polycaprolactone glycol into the reaction kettle, stirring and melting, adding isophorone diisocyanate, heating to 80 ℃, and reacting for 90 minutes;
s2, cooling to 60 ℃, adding N-methylpyrrolidone and 1, 4-butanediol, stirring uniformly, heating to 80 ℃, continuing to perform heat preservation reaction for 60 minutes, adding dimethylolbutyric acid and an organic bismuth catalyst, and continuing to perform heat preservation reaction until the NCO content reaches a design value;
s3, cooling after the reaction is finished, slowly adding metered acetone, cooling to about 40 ℃ after the acetone is added, adding N, N-dimethylethanolamine, increasing the stirring speed, and adding deionized water for high-speed dispersion; after the dispersion is finished, adding 1, 6-hexamethylene diamine for chain extension reaction;
and S4, heating to 60 ℃, decompressing the dispersion liquid to remove acetone, cooling to about 40 ℃ when the acetone is completely removed, filtering by using 200-mesh filter cloth, and packaging.
Example 2
The waterborne polyurethane resin is prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 42 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 42 portions of
Polycaprolactone diol (Mn ═ 2000): 42 portions of
N-methylpyrrolidone: 21 portions of
1, 4-butanediol: 7.5 parts of
Dimethylolbutyric acid: 6.5 parts of
Organic bismuth catalyst: 0.11 portion
Acetone: 135 portions of
N, N-dimethylethanolamine: 3.5 parts of
Deionized water: 153 portions of
1, 6-hexamethylenediamine: 2.3 parts.
The preparation method of the waterborne polyurethane resin comprises the following steps:
s1, adding polytetrahydrofuran ether glycol and polycaprolactone glycol into the reaction kettle, stirring and melting, adding isophorone diisocyanate, heating to 80 ℃, and reacting for 90 minutes;
s2, cooling to 60 ℃, adding N-methylpyrrolidone and 1, 4-butanediol, stirring uniformly, heating to 80 ℃, continuing to perform heat preservation reaction for 60 minutes, adding dimethylolbutyric acid and an organic bismuth catalyst, and continuing to perform heat preservation reaction until the NCO content reaches a design value;
s3, cooling after the reaction is finished, slowly adding metered acetone, cooling to about 40 ℃ after the acetone is added, adding N, N-dimethylethanolamine, increasing the stirring speed, and adding deionized water for high-speed dispersion; after the dispersion is finished, adding 1, 6-hexamethylene diamine for chain extension reaction;
and S4, heating to 60 ℃, decompressing the dispersion liquid to remove acetone, cooling to about 40 ℃ when the acetone is completely removed, filtering by using 200-mesh filter cloth, and packaging.
Example 3
The waterborne polyurethane resin is prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 40 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 40 portions of
Polycaprolactone diol (Mn ═ 2000): 40 portions of
N-methylpyrrolidone: 20 portions of
1, 4-butanediol: 7 portions of
Dimethylolbutyric acid: 6 portions of
Organic bismuth catalyst: 0.1 part
Acetone: 130 portions of
N, N-dimethylethanolamine: 3.4 parts of
Deionized water: 148 portions of
1, 6-hexamethylenediamine: 2.2 parts.
The preparation method of the waterborne polyurethane resin comprises the following steps:
s1, adding polytetrahydrofuran ether glycol and polycaprolactone glycol into the reaction kettle, stirring and melting, adding isophorone diisocyanate, heating to 80 ℃, and reacting for 90 minutes;
s2, cooling to 60 ℃, adding N-methylpyrrolidone and 1, 4-butanediol, stirring uniformly, heating to 80 ℃, continuing to perform heat preservation reaction for 60 minutes, adding dimethylolbutyric acid and an organic bismuth catalyst, and continuing to perform heat preservation reaction until the NCO content reaches a design value;
s3, cooling after the reaction is finished, slowly adding metered acetone, cooling to about 40 ℃ after the acetone is added, adding N, N-dimethylethanolamine, increasing the stirring speed, and adding deionized water for high-speed dispersion; after the dispersion is finished, adding 1, 6-hexamethylene diamine for chain extension reaction;
and S4, heating to 60 ℃, decompressing the dispersion liquid to remove acetone, cooling to about 40 ℃ when the acetone is completely removed, filtering by using 200-mesh filter cloth, and packaging.
The aqueous polyurethane resins prepared in the above examples 1 to 4 were respectively used to prepare aqueous adhesives according to the following raw materials in parts by weight:
the aqueous polyurethane resin described above: 90 portions of
Dispersing agent: 0.5 portion
Wetting agent: 0.3 part
Leveling agent: 0.3 part
Drying and regulating agent: 3 portions of
Defoaming agent: 0.5 portion
Water: 4.0 part
Thickening agent: 1 part of
And (3) bactericide: 0.4.
the comparison of the tensile strength and elongation of the prepared water-based adhesive and the common flocking adhesive is shown in the following table:
| tensile strength (N/cm) | Elongation (%) | |
| Aqueous adhesive of the present application | 30-33 | 50-100 |
| Common flocking adhesive | 25-27 | 200-300 |
Compared with the common flocking belt, the anti-stretching flocking adhesive has the advantages that the tensile strength is larger than 20 percent and the elongation rate is more than one time under the same glue thickness, which shows that the anti-stretching effect is better
The method has the advantages that the tensile strength and the larger elongation percentage of the product are increased, the hot-lamination process requirements of the current automobile industry on the on-line lamination of the automobile sealing strip flocking tape can be met, and the problem that the flocking tape is stretched after being heated in the production process is solved.
Finally, it is to be noted that: the above description is only a preferred embodiment of the present invention, and is only used to illustrate the technical solutions of the present invention, and not to limit the protection scope of the present invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention shall fall within the protection scope of the present invention.
Claims (8)
1. The waterborne polyurethane resin is characterized by being prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 38 to 42 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 38 to 42 portions of
Polycaprolactone diol (Mn ═ 2000): 38 to 42 portions of
N-methylpyrrolidone: 19 to 21 portions of
1, 4-butanediol: 6.5 to 7.5 portions of
Dimethylolbutyric acid: 5.5 to 6.5 portions of
Organic bismuth catalyst: 0.09 to 0.11 portion
Acetone: 125 portion
N, N-dimethylethanolamine: 3.3 to 3.5 portions
Deionized water: 143 portions 153-
1, 6-hexamethylenediamine: 2.1 to 2.3 portions.
2. The aqueous polyurethane resin according to claim 1, which is prepared from the following raw materials in parts by weight:
the feed is prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 38 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 38 portions of
Polycaprolactone diol (Mn ═ 2000): 38 portions of
N-methylpyrrolidone: 19-part(s)
1, 4-butanediol: 6.5 parts of
Dimethylolbutyric acid: 5.5 parts of
Organic bismuth catalyst: 0.09 part
Acetone: 125 portions of
N, N-dimethylethanolamine: 3.3 parts of
Deionized water: 143 portions of
1, 6-hexamethylenediamine: 2.1 parts.
3. The aqueous polyurethane resin according to claim 1, which is prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 42 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 42 portions of
Polycaprolactone diol (Mn ═ 2000): 42 portions of
N-methylpyrrolidone: 21 portions of
1, 4-butanediol: 7.5 parts of
Dimethylolbutyric acid: 6.5 parts of
Organic bismuth catalyst: 0.11 portion
Acetone: 135 portions of
N, N-dimethylethanolamine: 3.5 parts of
Deionized water: 153 portions of
1, 6-hexamethylenediamine: 2.3 parts.
4. The aqueous polyurethane resin according to claim 1, which is prepared from the following raw materials in parts by weight:
isophorone diisocyanate: 40 portions of
Polytetrahydrofuran ether glycol (Mn 2000): 40 portions of
Polycaprolactone diol (Mn ═ 2000): 40 portions of
N-methylpyrrolidone: 20 portions of
1, 4-butanediol: 7 portions of
Dimethylolbutyric acid: 6 portions of
Organic bismuth catalyst: 0.1 part
Acetone: 130 portions of
N, N-dimethylethanolamine: 3.4 parts of
Deionized water: 148 portions of
1, 6-hexamethylenediamine: 2.2 parts.
5. A method for producing the aqueous polyurethane resin according to any one of claims 1 to 4, characterized by comprising the steps of:
s1, adding polytetrahydrofuran ether glycol and polycaprolactone glycol into the reaction kettle, stirring and melting, adding isophorone diisocyanate, heating to 80 ℃, and reacting for 90 minutes;
s2, cooling to 60 ℃, adding N-methylpyrrolidone and 1, 4-butanediol, stirring uniformly, heating to 80 ℃, continuing to perform heat preservation reaction for 60 minutes, adding dimethylolbutyric acid and an organic bismuth catalyst, and continuing to perform heat preservation reaction until the NCO content reaches a design value;
s3, cooling after the reaction is finished, slowly adding metered acetone, cooling to about 40 ℃ after the acetone is added, adding N, N-dimethylethanolamine, increasing the stirring speed, and adding deionized water for high-speed dispersion; after the dispersion is finished, adding 1, 6-hexamethylene diamine for chain extension reaction;
and S4, heating to 60 ℃, decompressing the dispersion liquid to remove acetone, cooling to about 40 ℃ when the acetone is completely removed, filtering by using 200-mesh filter cloth, and packaging.
6. The water-based adhesive is characterized by comprising the following raw materials in parts by weight:
the aqueous polyurethane resin according to any one of claims 1 to 4: 90 portions of
Dispersing agent: 0.5 portion
Wetting agent: 0.3 part
Leveling agent: 0.3 part
Drying and regulating agent: 3 portions of
Defoaming agent: 0.5 portion
Water: 4.0 part
Thickening agent: 1 part of
And (3) bactericide: 0.4.
7. the aqueous binder of claim 6 wherein the drying modifier is propylene glycol and/or glycerol.
8. Use of an aqueous adhesive according to claim 6 or 7 for the adhesion of flock to substrate films for the flocking of sealing strips for motor vehicles.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115058184A (en) * | 2022-08-01 | 2022-09-16 | 江苏中瀛涂料有限公司 | Water-based environment-friendly coating and preparation method thereof |
| CN116144257A (en) * | 2023-02-24 | 2023-05-23 | 上海蓝欧化工科技有限公司 | Scratch-resistant wear-resistant self-extinction waterborne polyurethane emulsion and preparation method thereof |
| CN116692753A (en) * | 2023-06-13 | 2023-09-05 | 台州禾欣高分子新材料有限公司 | Synthetic process of polyurethane resin |
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| CN102936480A (en) * | 2012-11-08 | 2013-02-20 | 无锡市万力粘合材料有限公司 | Waterborne polyurethane adhesive for fabric and preparation method thereof |
| KR20150108063A (en) * | 2014-03-17 | 2015-09-25 | 주식회사 효성 | Urethane resin binder composition for adhesive coating layer, and optical film comprising the same |
| CN110105912A (en) * | 2019-05-10 | 2019-08-09 | 无锡市万力粘合材料股份有限公司 | Water-based polyurethane adhesive for automobile interiors and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102936480A (en) * | 2012-11-08 | 2013-02-20 | 无锡市万力粘合材料有限公司 | Waterborne polyurethane adhesive for fabric and preparation method thereof |
| KR20150108063A (en) * | 2014-03-17 | 2015-09-25 | 주식회사 효성 | Urethane resin binder composition for adhesive coating layer, and optical film comprising the same |
| CN110105912A (en) * | 2019-05-10 | 2019-08-09 | 无锡市万力粘合材料股份有限公司 | Water-based polyurethane adhesive for automobile interiors and preparation method thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115058184A (en) * | 2022-08-01 | 2022-09-16 | 江苏中瀛涂料有限公司 | Water-based environment-friendly coating and preparation method thereof |
| CN116144257A (en) * | 2023-02-24 | 2023-05-23 | 上海蓝欧化工科技有限公司 | Scratch-resistant wear-resistant self-extinction waterborne polyurethane emulsion and preparation method thereof |
| CN116144257B (en) * | 2023-02-24 | 2024-01-30 | 上海蓝欧化工科技有限公司 | Scratch-resistant wear-resistant self-extinction waterborne polyurethane emulsion and preparation method thereof |
| CN116692753A (en) * | 2023-06-13 | 2023-09-05 | 台州禾欣高分子新材料有限公司 | Synthetic process of polyurethane resin |
| CN116692753B (en) * | 2023-06-13 | 2023-12-26 | 台州禾欣高分子新材料有限公司 | Synthetic process of polyurethane resin |
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