CN111849408A - Moisture-curing polyurethane hot melt adhesive with high initial adhesion strength and preparation method thereof - Google Patents
Moisture-curing polyurethane hot melt adhesive with high initial adhesion strength and preparation method thereof Download PDFInfo
- Publication number
- CN111849408A CN111849408A CN202010577559.6A CN202010577559A CN111849408A CN 111849408 A CN111849408 A CN 111849408A CN 202010577559 A CN202010577559 A CN 202010577559A CN 111849408 A CN111849408 A CN 111849408A
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- China
- Prior art keywords
- hot melt
- melt adhesive
- polyurethane hot
- adhesion strength
- parts
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- 239000004831 Hot glue Substances 0.000 title claims abstract description 33
- 239000004814 polyurethane Substances 0.000 title claims abstract description 33
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 29
- 238000013008 moisture curing Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 16
- 229920005989 resin Polymers 0.000 claims abstract description 16
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 15
- 229920000570 polyether Polymers 0.000 claims abstract description 15
- 229920005862 polyol Polymers 0.000 claims abstract description 15
- 150000003077 polyols Chemical class 0.000 claims abstract description 15
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 14
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 11
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 5
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 5
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 5
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 34
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 238000003756 stirring Methods 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 16
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 12
- 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 11
- 239000000203 mixture Substances 0.000 claims description 11
- -1 polyoxyethylene Polymers 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 8
- 238000007789 sealing Methods 0.000 claims description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 8
- 238000003860 storage Methods 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 3
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 claims description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- IIGAAOXXRKTFAM-UHFFFAOYSA-N N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C Chemical compound N=C=O.N=C=O.CC1=C(C)C(C)=C(C)C(C)=C1C IIGAAOXXRKTFAM-UHFFFAOYSA-N 0.000 claims description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 2
- 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 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 235000007586 terpenes Nutrition 0.000 claims description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000001723 curing Methods 0.000 abstract description 3
- 238000012423 maintenance Methods 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract 1
- 239000003292 glue Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 1
- RNSLCHIAOHUARI-UHFFFAOYSA-N butane-1,4-diol;hexanedioic acid Chemical compound OCCCCO.OC(=O)CCCCC(O)=O RNSLCHIAOHUARI-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
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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
- C09J175/08—Polyurethanes from polyethers
-
- 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
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4063—Mixtures of compounds of group C08G18/62 with other macromolecular compounds
-
- 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
- C08G18/4202—Two or more polyesters of different physical or chemical nature
-
- 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
- C08G18/4236—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
-
- 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
- C08G18/4825—Polyethers containing two hydroxy groups
-
- 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
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene 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
- C08G18/48—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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
- C08G18/6229—Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
-
- 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
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a high initial adhesion strength moisture-curing polyurethane hot melt adhesive and a preparation method thereof, wherein the high initial adhesion strength moisture-curing polyurethane hot melt adhesive is prepared from the following raw materials in parts by weight: 20-50 parts of polyether polyol, 10-40 parts of crystalline polyester polyol, 5-30 parts of liquid polyester polyol, 10-20 parts of polyisocyanate, 10-35 parts of thermoplastic acrylic resin, 2-15 parts of tackifying resin, 0.1-0.5 part of catalyst and 0.1-1 part of antioxidant. The moisture-curing polyurethane hot melt adhesive provided by the invention has the advantages of long opening time, high initial adhesion strength, high curing speed, higher final adhesion strength, good damp and heat resistance and high and low temperature impact resistance, can achieve pressure-free maintenance and realizes high-efficiency production of electronic products.
Description
Technical Field
The invention belongs to the field of reactive polyurethane hot melt adhesives, and relates to a high initial adhesion strength reactive polyurethane hot melt adhesive for quickly assembling electronic products.
Background
The reactive moisture-curing polyurethane hot melt adhesive (PUR) has 100 percent of solid content and no solvent, is an environment-friendly adhesive, is quick to position, and is widely applied to the fields of household appliances, handheld electronic equipment, woodwork, textile, automobile interior trim and the like in recent years. The PUR is solid at normal temperature, is melted into liquid after being heated, and is applied to bonding of base materials. When the adhesive cools to become a solid, the initial strength is provided due to the cooling crystallization and physical crosslinking of the polyurethane prepolymer. The isocyanate then reacts with the substrate surface and moisture in the air to form chemical crosslinks that provide the final bond.
Traditional PUR hot melt adhesive is just viscous force little, needs longer pressurize time in the electron device manufacture process, and more pressurize tool has greatly reduced production efficiency. In order to improve the production efficiency and meet the requirement of a fast assembly flow line, the high-performance and high-initial-adhesion-strength polyurethane hot melt adhesive is increasingly required.
Disclosure of Invention
In order to solve the technical problems, the invention aims to improve the PUR hot melt adhesive with weak initial adhesion strength and long pressure maintaining time, improve the initial adhesion strength and shorten the pressure maintaining time under the condition of long opening time, and simultaneously have good damp and heat resistance and high and low temperature cold and hot impact resistance.
The technical scheme of the invention is as follows:
the utility model provides a high initial adhesion strength moisture cure polyurethane hot melt adhesive which characterized in that: the coating comprises the following components in parts by weight: 20-50 parts of polyether polyol, 10-40 parts of crystalline polyester polyol, 5-30 parts of liquid polyester polyol, 10-20 parts of polyisocyanate, 10-35 parts of thermoplastic acrylic resin, 2-15 parts of tackifying resin, 0.1-0.5 part of catalyst and 0.1-1 part of antioxidant.
Further, the polyether polyol has the number average molecular weight of 1000-4000; the polyether polyol is one or more of polyoxypropylene glycol, polyoxyethylene glycol, polyoxypropylene-oxyethylene glycol and polytetrahydrofuran ether.
Further, the number average molecular weight of the crystalline polyester polyol is 1000-4000; the crystalline polyester polyol is formed by polymerizing at least one acid of adipic acid, sebacic acid and dodecanoic acid with at least one alcohol of 1, 4-butanediol, neopentyl glycol, ethylene glycol, diethylene glycol and 1, 6-hexanediol, and comprises a mixture of one or more crystalline polyester polyols.
Further, the number average molecular weight of the liquid polyester polyol is 1000-4000; the liquid polyester polyol is prepared by performing polycondensation reaction on one or more of isophthalic acid, terephthalic acid, phthalic anhydride, adipic acid and sebacic acid and one or more of ethylene glycol, diethylene glycol, neopentyl glycol, 1, 4-butanediol, 1, 6-hexanediol and 3-methyl-1, 5-pentanediol.
Further, the polyisocyanate includes one or a mixture of two or more of 4, 4-diphenylmethane diisocyanate (MDI), 1, 3-diphenylmethane diisocyanate (XDI), Toluene Diisocyanate (TDI), Xylene Diisocyanate (XDI), Hexamethylene Diisocyanate (HDI), isophorone diisocyanate (IPDI), tetramethylxylene diisocyanate (TMXDI), carbodiimide-modified MDI, and naphthalene diisocyanate.
Further, the weight average molecular weight of the thermoplastic acrylic resin is 10000-50000; the acrylic resin comprises methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, butyl methacrylate and copolymer; the acrylic acid contains active groups of hydroxyethyl acrylate and hydroxypropyl acrylate, and the hydroxyl value is 2-15mg KOH/g.
Furthermore, the tackifying resin is one or a mixture of terpene resin, rosin resin and petroleum resin.
Further, the catalyst is one or more of dibutyltin dilaurate, stannous octoate, dibutylene acetate, triethylene diamine and dimorpholinyl diethyl ether.
Further, the preparation steps are as follows:
step 1: putting polyether polyol, polyester polyol, acrylic resin, an antioxidant and tackifying resin into a reaction kettle according to a metering ratio, heating to 120 ℃, vacuumizing, stirring and dehydrating for 2 hours;
step 2: cooling to 70 ℃, adding diphenylmethane diisocyanate under the protection of nitrogen, slowly heating to 95 ℃, and stirring for reacting for 2 hours under the protection of nitrogen;
and step 3: adding dimorpholinyl diethyl ether under the protection of nitrogen, stirring at 95 ℃ for reaction for 15min, defoaming in vacuum, and sealing for storage to obtain the polyurethane hot melt adhesive.
Further, the vacuum degree in the step 1 is-0.09 Mpa to-0.1 Mpa.
By the scheme, the invention at least has the following advantages:
the moisture-curing polyurethane hot melt adhesive provided by the invention has the advantages of long opening time, high initial adhesion strength, high curing speed, higher final adhesion strength, good damp and heat resistance and high and low temperature impact resistance, can achieve pressure-free maintenance, and is used for realizing high-efficiency production of electronic products in electronic products.
The foregoing is a summary of the present invention, and in order to provide a clear understanding of the technical means of the present invention and to be implemented in accordance with the present specification, the following is a detailed description of the preferred embodiments of the present invention.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The preparation method of the reactive polyurethane hot melt adhesive comprises the following steps:
step 1: putting polyether polyol, polyester polyol, acrylic resin, an antioxidant and tackifying resin into a reaction kettle according to a metering ratio, heating to 120 ℃, vacuumizing (the vacuum degree is-0.09 Mpa to-0.1 Mpa), and stirring for dehydration for 2 hours;
Step 2: cooling to 70 ℃, adding diphenylmethane diisocyanate under the protection of nitrogen, slowly heating to 95 ℃, and stirring for reacting for 2 hours under the protection of nitrogen;
and step 3: adding dimorpholinyl diethyl ether under the protection of nitrogen, stirring at 95 ℃ for reaction for 15min, defoaming in vacuum, and sealing for storage to obtain the polyurethane hot melt adhesive.
Example 1
Adding 270g of polyether polyol, 210g of a mixture of polydodecanoic acid-1, 6-hexanediol ester diol and poly adipic acid-1, 6-hexanediol ester diol, 107g of liquid polyester polyol, 250g of hydroxy acrylic resin, 30g of tackifying resin and 1.9g of antioxidant into a reaction kettle, heating to 120 ℃, and vacuumizing (the vacuum degree is-0.09 Mpa to-0.1 Mpa), and stirring and dehydrating for 2 hours; cooling to 70 ℃, adding 130g of diphenylmethane diisocyanate under the protection of nitrogen, slowly heating to 95 ℃, and stirring for reaction for 2 hours under the protection of nitrogen; adding 2g of dimorpholinyl diethyl ether serving as a catalyst under the protection of nitrogen, stirring at 95 ℃ for reaction for 15min, defoaming in vacuum, and sealing for storage to prepare the polyurethane hot melt adhesive.
Example 2
Adding 270g of polyether polyol, 210g of a mixture of polysebacic acid-1, 6-hexanediol glycol and polyhexamethylene adipate-1, 6-hexanediol glycol, 107g of liquid polyester polyol, 250g of acrylic resin, 30g of tackifying resin and 1.9g of antioxidant into a reaction kettle, heating to 120 ℃, and vacuumizing (the vacuum degree is-0.09 Mpa to-0.1 Mpa), and stirring and dehydrating for 2 hours; cooling to 70 ℃, adding 127g of diphenylmethane diisocyanate under the protection of nitrogen, slowly heating to 95 ℃, and stirring for reaction for 2h under the protection of nitrogen; adding 2g of dimorpholinyl diethyl ether serving as a catalyst under the protection of nitrogen, stirring at 95 ℃ for reaction for 15min, defoaming in vacuum, and sealing for storage to prepare the polyurethane hot melt adhesive.
Example 3
Adding 280g of polyether polyol, 220g of a mixture of polysebacic acid-1, 6-hexanediol glycol and poly adipic acid-1, 4-butanediol glycol, 110g of liquid polyester polyol, 250g of hydroxy acrylic resin and 2g of antioxidant into a reaction kettle, heating to 120 ℃, vacuumizing (the vacuum degree is-0.09 Mpa to-0.1 Mpa), and stirring and dehydrating for 2 hours; cooling to 70 ℃, adding 135g of diphenylmethane diisocyanate under the protection of nitrogen, slowly heating to 95 ℃, and stirring for reaction for 2 hours under the protection of nitrogen; adding 2g of dimorpholinyl diethyl ether serving as a catalyst under the protection of nitrogen, stirring at 100 ℃ for reaction for 15min, defoaming in vacuum, and sealing for storage to prepare the polyurethane hot melt adhesive.
Example 4
Adding 280g of polyether polyol, 220g of a mixture of poly dodecanoic acid-1, 6-hexanediol ester diol and poly adipic acid-1, 4-butanediol ester diol, 110g of liquid polyester polyol, 250g of acrylic resin and 2g of antioxidant into a reaction kettle, heating to 120 ℃, vacuumizing (the vacuum degree is-0.09 MPa to-0.1 MPa), and stirring and dehydrating for 2 hours; cooling to 70 ℃, adding 135g of diphenylmethane diisocyanate under the protection of nitrogen, slowly heating to 95 ℃, and stirring for reaction for 2 hours under the protection of nitrogen; adding 2.5g of dimorpholinyl diethyl ether serving as a catalyst under the protection of nitrogen, stirring at 95 ℃ for reaction for 15min, defoaming in vacuum, and sealing for storage to prepare the polyurethane hot melt adhesive.
Comparative examples
Adding 350g of polyether polyol, 300g of a mixture of poly dodecanoic acid-1, 6-hexanediol ester diol and poly adipic acid-1, 6-hexanediol ester diol, 150g of liquid polyester polyol and 1.9g of antioxidant into a reaction kettle, heating to 120 ℃, vacuumizing (the vacuum degree is-0.09 MPa to-0.1 MPa), and stirring and dehydrating for 2 hours; cooling to 70 ℃, adding 137g of diphenylmethane diisocyanate under the protection of nitrogen, slowly heating to 95 ℃, and stirring for reacting for 2 hours under the protection of nitrogen; adding 3g of dimorpholinyl diethyl ether serving as a catalyst under the protection of nitrogen, stirring at 95 ℃ for reaction for 15min, defoaming in vacuum, and sealing for storage to prepare the polyurethane hot melt adhesive.
Table 1 results of performance tests of examples 1 to 4 and comparative examples
Test methods for examples and comparative examples:
and (3) viscosity testing: test using a Brookfield Thermosel viscometer at 110 ℃, 27# spindle.
Opening time: melting the adhesive at 130 deg.C for 20min, dispensing a 0.6mm wide glue line on the plastic substrate, and sticking PC sheet on the glue line at certain intervals, wherein the open time is the PC surface glue residue less than 50%.
Drawing strength: two 10mm by 40mm PC test pieces are crossly lapped, the thickness of a glue layer is 0.15mm, the pressure is maintained for 1min, the PC test pieces are cured under the environment of temperature and humidity of 25 +/-1 ℃/50 +/-5% RH, and the drawing test is carried out for 100 mm/min.
Cold and hot impact: after the glue is cured for 72h, the temperature is cycled from minus 40 ℃ to 70 ℃, 1h/cycle, 500cycles, and then the glue is kept for 24h at room temperature and tested at room temperature.
High temperature and high humidity: and after the glue is cured for 72h, the temperature and the humidity are 85 ℃/85% RH for 500h, then the glue is kept for 24h at room temperature, and the test is carried out at the room temperature.
The invention has at least the following advantages:
the moisture-curing polyurethane hot melt adhesive provided by the invention has the advantages of long opening time, high initial adhesion strength, high curing speed, higher final adhesion strength, good damp and heat resistance and high and low temperature impact resistance, can achieve pressure-free maintenance, and is used for realizing high-efficiency production of electronic products in electronic products.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, it should be noted that, for those skilled in the art, many modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (10)
1. The utility model provides a high initial adhesion strength moisture cure polyurethane hot melt adhesive which characterized in that: the coating comprises the following components in parts by weight: 20-50 parts of polyether polyol, 10-40 parts of crystalline polyester polyol, 5-30 parts of liquid polyester polyol, 10-20 parts of polyisocyanate, 10-35 parts of thermoplastic acrylic resin, 2-15 parts of tackifying resin, 0.1-0.5 part of catalyst and 0.1-1 part of antioxidant.
2. The high initial adhesion strength moisture-curable polyurethane hot melt adhesive according to claim 1, wherein the polyether polyol has a number average molecular weight of 1000 to 4000; the polyether polyol is one or more of polyoxypropylene glycol, polyoxyethylene glycol, polyoxypropylene-oxyethylene glycol and polytetrahydrofuran ether.
3. The high initial adhesion strength moisture-curing polyurethane hot melt adhesive according to claim 1, which is characterized in that: the number average molecular weight of the crystalline polyester polyol is 1000-4000; the crystalline polyester polyol is formed by polymerizing at least one acid of adipic acid, sebacic acid and dodecanoic acid with at least one alcohol of 1, 4-butanediol, neopentyl glycol, ethylene glycol, diethylene glycol and 1, 6-hexanediol, and comprises a mixture of one or more crystalline polyester polyols.
4. The high initial adhesion strength moisture-curing polyurethane hot melt adhesive according to claim 1, which is characterized in that: the number average molecular weight of the liquid polyester polyol is 1000-4000; the liquid polyester polyol is prepared by performing polycondensation reaction on one or more of isophthalic acid, terephthalic acid, phthalic anhydride, adipic acid and sebacic acid and one or more of ethylene glycol, diethylene glycol, neopentyl glycol, 1, 4-butanediol, 1, 6-hexanediol and 3-methyl-1, 5-pentanediol.
5. The high initial adhesion strength moisture-curing polyurethane hot melt adhesive according to claim 1, which is characterized in that: the polyisocyanate comprises one or a mixture of more than two of 4, 4-diphenylmethane diisocyanate (MDI), 1, 3-diphenylmethane diisocyanate (XDI), Toluene Diisocyanate (TDI), Xylene Diisocyanate (XDI), Hexamethylene Diisocyanate (HDI), isophorone diisocyanate (IPDI), tetramethylxylene diisocyanate (TMXDI), carbodiimide modified MDI and naphthalene diisocyanate.
6. The high initial adhesion strength moisture-curing polyurethane hot melt adhesive according to claim 1, which is characterized in that: the weight average molecular weight of the thermoplastic acrylic resin is 10000-50000; the acrylic resin comprises methyl acrylate, ethyl acrylate, butyl acrylate, methyl methacrylate, butyl methacrylate and copolymer; the acrylic acid contains active groups of hydroxyethyl acrylate and hydroxypropyl acrylate, and the hydroxyl value is 2-15mg KOH/g.
7. The high initial adhesion strength moisture-curing polyurethane hot melt adhesive according to claim 1, which is characterized in that: the tackifying resin is one or a mixture of terpene resin, rosin resin and petroleum resin.
8. The high initial adhesion strength moisture-curing polyurethane hot melt adhesive according to claim 1, which is characterized in that: the catalyst is one or more of dibutyltin dilaurate, stannous octoate, dibutylene acetate, triethylene diamine and dimorpholinyl diethyl ether.
9. The polyurethane hot melt adhesive according to any one of claims 1 to 9, wherein: the preparation steps are as follows:
step 1: putting polyether polyol, polyester polyol, acrylic resin, an antioxidant and tackifying resin into a reaction kettle according to a metering ratio, heating to 120 ℃, vacuumizing, stirring and dehydrating for 2 hours;
step 2: cooling to 70 ℃, adding diphenylmethane diisocyanate under the protection of nitrogen, slowly heating to 95 ℃, and stirring for reacting for 2 hours under the protection of nitrogen;
and step 3: adding dimorpholinyl diethyl ether under the protection of nitrogen, stirring at 95 ℃ for reaction for 15min, defoaming in vacuum, and sealing for storage to obtain the polyurethane hot melt adhesive.
10. The polyurethane hot melt adhesive of claim 9, wherein: the vacuum degree in the step 1 is-0.09 Mpa to-0.1 Mpa.
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