CN108659775A - A kind of bi-component solvent-free reaction type polyurethane hot melt adhesive and its application method applied to electronic appliance industry - Google Patents
A kind of bi-component solvent-free reaction type polyurethane hot melt adhesive and its application method applied to electronic appliance industry Download PDFInfo
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- CN108659775A CN108659775A CN201810316880.1A CN201810316880A CN108659775A CN 108659775 A CN108659775 A CN 108659775A CN 201810316880 A CN201810316880 A CN 201810316880A CN 108659775 A CN108659775 A CN 108659775A
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- Prior art keywords
- component
- anhydride
- polyol
- type polyurethane
- reaction type
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- 239000004814 polyurethane Substances 0.000 title claims abstract description 31
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 29
- 238000006561 solvent free reaction Methods 0.000 title claims abstract description 22
- 239000004831 Hot glue Substances 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 239000000853 adhesive Substances 0.000 claims abstract description 5
- 230000001070 adhesive effect Effects 0.000 claims abstract description 5
- 239000012943 hotmelt Substances 0.000 claims abstract 2
- 150000003077 polyols Chemical class 0.000 claims description 26
- 229920005862 polyol Polymers 0.000 claims description 25
- 150000008064 anhydrides Chemical class 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 239000003292 glue Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- -1 bismuth carboxylate Chemical class 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 150000005846 sugar alcohols Polymers 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 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 10
- 239000012752 auxiliary agent Substances 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000004970 Chain extender Substances 0.000 claims description 7
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000005516 engineering process Methods 0.000 claims description 7
- 239000003822 epoxy resin Substances 0.000 claims description 7
- 229920000647 polyepoxide Polymers 0.000 claims description 7
- 229920005906 polyester polyol Polymers 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002518 antifoaming agent Substances 0.000 claims description 6
- 229910052797 bismuth Inorganic materials 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 239000005056 polyisocyanate Substances 0.000 claims description 5
- 229920001228 polyisocyanate Polymers 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- XISFOXBYRQWDNK-UHFFFAOYSA-N 2-(2-methylphenyl)propan-2-amine;hydrochloride Chemical compound [Cl-].CC1=CC=CC=C1C(C)(C)[NH3+] XISFOXBYRQWDNK-UHFFFAOYSA-N 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 3
- 238000003723 Smelting Methods 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical class CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000000320 mechanical mixture Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 229920001296 polysiloxane Polymers 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000007761 roller coating Methods 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 230000003068 static effect Effects 0.000 claims description 3
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims description 3
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 claims description 2
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 claims description 2
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 claims description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 2
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical class CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 claims description 2
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical group C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 claims description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 2
- FKBMTBAXDISZGN-UHFFFAOYSA-N 5-methyl-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical class C1C(C)CCC2C(=O)OC(=O)C12 FKBMTBAXDISZGN-UHFFFAOYSA-N 0.000 claims description 2
- DXRFZHILMCWCNG-UHFFFAOYSA-N N,N-dimethyl-1,8-naphthyridin-2-amine Chemical compound C1=CC=NC2=NC(N(C)C)=CC=C21 DXRFZHILMCWCNG-UHFFFAOYSA-N 0.000 claims description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Nonanedioid acid Natural products OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004677 Nylon Substances 0.000 claims description 2
- 229920002732 Polyanhydride Polymers 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
- 229910052787 antimony Inorganic materials 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
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 claims description 2
- ILHIHKRJJMKBEE-UHFFFAOYSA-N hydroperoxyethane Chemical compound CCOO ILHIHKRJJMKBEE-UHFFFAOYSA-N 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 229920001778 nylon Polymers 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229940014800 succinic anhydride Drugs 0.000 claims description 2
- 239000005028 tinplate Substances 0.000 claims description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims 1
- IEDKVDCIEARIIU-UHFFFAOYSA-N 2-Nonadecanone Chemical compound CCCCCCCCCCCCCCCCCC(C)=O IEDKVDCIEARIIU-UHFFFAOYSA-N 0.000 claims 1
- 235000009508 confectionery Nutrition 0.000 claims 1
- VGGRCVDNFAQIKO-UHFFFAOYSA-N formic anhydride Chemical compound O=COC=O VGGRCVDNFAQIKO-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000006757 chemical reactions by type Methods 0.000 abstract description 3
- 239000004593 Epoxy Substances 0.000 abstract description 2
- 238000010276 construction Methods 0.000 abstract description 2
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
-
- 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
-
- 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
- C08G18/70—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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- 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
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)
Abstract
The invention discloses a kind of bi-component solvent-free reaction type polyurethane hot melt adhesive applied to electronic appliance industry, polyurethane adhesive in the present invention is bi-component reaction-type polyurethane hot melt, not only contain hydroxyl in component, also contain epoxy construction, Ju oxazolidones can be generated with end NCO prepolymer reactions, the high temperature resistance after hot melt adhesive curing is increased, reaction is not mainly that humidity is limited by environment, and final Young's modulus can reach 1000Mpa or more.
Description
Technical field
The present invention relates to a kind of bi-component solvent-free reaction type polyurethane hot melt adhesive and its application methods, more particularly to one kind
Bi-component solvent-free reaction type polyurethane hot melt adhesive and its application method applied to electronic appliance industry.
Background technology
The PUR for being traditionally used for electronic appliance industry is usually one-component reaction type polyurethane hot-melt adhesive, is designed by connector
Relatively long with the hardening time of the influence of moisture content in environment, PUR, adhesion strength rises slowly, and Young's modulus is relatively low, heat-resisting
Property is poor.In this way, in the production of electronic appliance industry such as electronics and automobile lamp, seriously affect the production technology efficiency and
How quality can both improve the efficiency of production, it is also ensured that required bond quality, be the technical staff of the industry urgently
It solves the problems, such as.
Invention content
The present invention is intended to overcome the deficiencies of existing technologies, and it is an object of the present invention to provide a kind of applied to electronic appliance industry
Bi-component solvent-free reaction type polyurethane hot melt adhesive, can both improve the efficiency of production, it is also ensured that required bond quality.
The technical solution adopted by the present invention to solve the technical problems is：A kind of bi-component applied to electronic appliance industry
Solvent-free reaction type polyurethane hot melt adhesive, including component A and component B：
--- the component A includes performed polymer, auxiliary agent, the first catalyst that side chain or main chain carry isocyanato；
Wherein performed polymer degree of functionality is more than or equal to 1, isocyano-content 0.1%-30%；Performed polymer in the component A is
Polyisocyanates polymerize generation with polyol b, wherein polyisocyanates be isophorone diisocyanate (IPDI) and
Methyl diphenylene diisocyanate (MDI) (IPDI by a certain percentage:MDI=0.2-1 composition), and account for the total matter of component A
The 30-80% of amount；The polyol b is one or more compositions that side chain or main chain carry hydroxyl group, including
Polyether polyol, polyester polyol, hydroxyl value ranging from 60-220mgKOH/g, molecular weight are 50-2000 dalton, preferably 400-
1000 dalton；Wherein polyol b accounts for the 20-70% of component A gross masses.It is water-fast after IPDI increase glue curings
Solution property and adhesion strength, polyol b ratios are higher, and glue curing speed is slower, and oligomer molecules amount is bigger, and viscosity is got over
It is high；
Auxiliary agent in the component A includes antifoaming agent, levelling agent, antioxidant, and additive amount is the 0.1- of component A total weights
5%；The antifoaming agent is non-silicone high molecular polymer, and the levelling agent is Siloxane-Oxyalkylene Copolymers compound, described anti-
Oxygen agent is Hinered phenols.
First catalyst includes triethylenediamine, bis- (dimethylaminoethyl) ethers and dibutyl tin laurate, carboxylic
The sour one or more compositions of bismuth, preferably bismuth carboxylate, content are the 0.01-0.5% of component A gross masses；First catalyst improves
Reaction speed shortens the reaction time；
The synthesis technology of the component A is：Polyol b, MDI, IPDI and the first catalysis is added to reaction kettle
Agent, control material temperature react 1-2h at 40-50 DEG C；60-70 DEG C, react 1-2h；80-100 DEG C, 1-4h is reacted, finger is reached
Determine viscosity (2000-20000cps/120 DEG C, preferably 5000-10000cps/120 DEG C), then auxiliary agent is added into reaction kettle, 80-
It is cooled to 40 DEG C after 100 DEG C of stirring 0.5-1h and terminates reaction, and 400 mesh filter screen filtering and dischargings form component A finished products.
--- the component B includes polyol a, anhydride modified polyalcohol, bisphenol A epoxide resin, chain extender, amine
Class catalyst；
Polyol a in the component B is one or more compositions that side chain or main chain carry hydroxyl group,
Including polyether polyol, polyester polyol, molecular weight is 500-4000 dalton, preferably 500-2000 dalton, hydroxyl value range
For 10-250mgKOH/g, the 10-70% of component B total weights is accounted for.(after the higher glue curing of ratio of polyol (1)
Modulus is lower, and adhesion strength is lower；Viscosity is lower after AB mixing, is conducive to improve production line coating speed)
Anhydride modified polyalcohol accounts for the 5-60% of component B total weights in the component B, anhydride modified more in the component B
First alcohol synthesis signal：
R ', R1, R2For alkyl, aryl；Or alkyl, the aryl replaced with methacryloxy or vinyl；Or
Alkoxy, phenoxy group；Optimizing alkyl (carbon atom number 1-5) or aryl (carbon atom number 6-10)；X is NH3-, OH-, SH-
Deng；R is alkyl (carbon atom number 1-20) or aryl (carbon atom number 6-20).
Acid anhydrides in the anhydride modified polyalcohol is phthalic anhydride, maleic anhydride, tetrabydrophthalic anhydride, six
Hydrogen phthalic anhydride, 3- methyl and 4- methylhexahydrophthalic anhydrides, 3- methyl and 4- ethyl hexahydrophthalic acids
Acid anhydride, itaconic anhydride, succinic anhydride, the eleventh of the twelve Earthly Branches dicarboxylic anhydride, adipic anhydride, carbic anhydride, methylnadic anhydride, hydrogenating methyl receive enlightening
Gram acid anhydrides, poly- azelaic acid acid anhydride, poly sebacic polyanhydride, poly- icosane diacid anhydride, trimellitic anhydride, pyromellitic acid anhydride,
Any one in 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydrides.
Further, the anhydride modified polyalcohol synthesis preparation method：By chemical compounds I and II and second catalyst
Reactor is added, temperature is controlled at 80-120 DEG C, reacts 1-4h, and interval half an hour measures acid value, after acid value is stablized, is continued
Compound III is added to reactor, control temperature measures acid value in 80 DEG C of -140 DEG C of reaction 1-6h, when acid value is less than 10mg
It is considered as reaction end when KOH/g, preferably smaller than 5mg KOH/g；
Second catalyst is triethylamine, trimethyl benzyl ammonia chloride, N, N- dimethyl benzylamines, N, N- dimethylbenzyl benzene
Amine, trimethyl benzyl ammonia chloride, triphenylphosphine, antimony triphenyl, acetylacetone metal complex, tetraethylammonium bromide, pyridine or
Any one in dimethylamino naphthyridine or several mixture.
The bisphenol A epoxide resin, epoxy-ester 0.2-0.6 account for the 5-60% of component B total weights.(epoxy resin ratio
Modulus is higher after higher glue curing, and adhesion strength is higher, and heat-resisting water resistance is better after solidification)
The chain extender is 4,4'- diamino -3,3'- dichloro diphenyl methanes, 2,4- diamino -3,5- dimethyl sulphur-based first
Benzene, glycerine, hydroquinone two hydroxy ethyl ether, one or more compositions in resorcinol two (2- ethoxys) ether account for component B
The 0.1-10% of gross mass, preferably 1-5%.Chain extender is for improving glue curing reaction speed and final glue after AB is mixed
Molecular weight, modulus is higher after the higher glue curing of content, and adhesion strength is higher)
The amines catalyst includes N, N- dimethyl cyclohexyl amines, N, and one kind in N- dimethyl benzylamines or composition account for
The 0.01-1% of component B gross masses.
The each component of said components B is uniformly mixed stirring 1-2 hours at normal temperatures, is then allowed to stand 1-2 hours and is consolidated
The component B of body state.
In addition, the invention further relates to bi-component solvent-free reaction type polyurethane hot melt adhesive to be applied to electronic appliance industry
Application method includes the following steps：
(1) before use, component A and component B are packed with independent sealing container respectively, the sealing container include but
It is not limited to tinplate bucket, PET/Al/Nylon/PP films etc. or combinations thereof.
(2) process is used, component A and B component are not put into glue-smelting machine and are heated to 80-120 DEG C of melting, passes through metering pump
In proportion (100：30~100：100) being output to static mixing tube mixing or mechanical mixture makes two kinds of components be uniformly mixed, and obtains
The bi-component solvent-free reaction type polyurethane glue.
(3) reach 40-50 DEG C to applying gum base materials and carrying out being preheated to substrate surface；
(4) after uniformly mixed polyurethane adhesive being heated to 80-120 DEG C, pass through the modes such as spraying, roller coating, showering, squeezing and coating
Substrate surface is glued.
(5) another base material being bonded will be needed to be bonded by mechanical force realization with gum base materials are applied.
Further, the ratio of the component A and component B is 1：0.3~1：0.5
Further, bi-component solvent-free reaction type polyurethane hot melt adhesive modulus after mixing for 24 hours reaches 200-
1500Mpa。
The bi-component solvent-free reaction type polyurethane hot melt adhesive be applied to electronic appliance industry, the present invention in bi-component without
Not only contain hydroxyl in the component of solvent reaction type polyurethane hot melt adhesive, also contains epoxy construction, it can be with end NCO prepolymer reactions
Poly- oxazolidone is generated, increases the high temperature resistance after hot melt adhesive curing, reaction is not mainly that humidity is limited by environment, finally
Young's modulus can reach 1000Mpa or more.Both the efficiency of production had been improved, it is also ensured that required bond quality has wide
Market prospects.
Specific implementation mode
Embodiment 1
A kind of bi-component solvent-free reaction type polyurethane applied to electronic appliance industry described in the embodiment of the present invention 1
Hot melt adhesive, including component A and component B：
--- the component A includes performed polymer, auxiliary agent, the first catalyst that side chain carries isocyanato；It is wherein pre-
Aggressiveness degree of functionality is more than or equal to 1, isocyano-content 20%；
Performed polymer in the component A is that polyisocyanates polymerize generation, wherein polyisocyanic acid with polyol b
Ester is isophorone diisocyanate (IPDI) and methyl diphenylene diisocyanate (MDI) (IPDI in proportion:MDI=0.6)
Made of composition, and account for the 60% of component A gross masses；The polyol b is polyether polyol, selects day Winsization
Work limited liability company P-2707 hydroxyl value of polyester polyol ranging from 150-180mgKOH/g, molecular weight are 700 dalton；Its
Middle polyol b accounts for the 50% of component A gross masses.
Auxiliary agent in the component A includes antifoaming agent, levelling agent, antioxidant, and additive amount is the 3% of component A total weights；
The antifoaming agent is non-silicone high molecular polymer, and the levelling agent is Siloxane-Oxyalkylene Copolymers compound, the antioxidant
For Hinered phenols.
First catalyst is bismuth carboxylate, and content is the 0.25% of component A gross masses.
The synthesis technology of the component A is：To P-2707 polyester polyol is added in reaction kettle, MDI, IPDI and first are urged
Agent, control material temperature react 2h at 50 DEG C；70 DEG C, react 2h；100 DEG C, 1h is reacted, specified viscosity is reached
(9000cps/120 DEG C), then auxiliary agent is added into reaction kettle, being cooled to 40 DEG C after 100 DEG C of stirring 1h terminates reaction, and 400 mesh
Strainer filtering discharging forms component A finished products.
--- the component B includes anhydride modified polyalcohol, polyol a, bisphenol A epoxide resin, chain extender, amine
Class catalyst；
Polyol a in the component B is polyether polyol, selects day Wins chemical inc P-2715
Hydroxyl value of polyester polyol ranging from molecular weight is 1500 dalton, hydroxyl value ranging from 72-78mgKOH/g；Account for component B total weights
40%.
Anhydride modified polyalcohol accounts for the 30% of component B total weights in the component B, anhydride modified polynary in the component B
Alcohol synthesis signal：
R ', R1, R2 are alkyl (carbon atom number 4)；X is OH-；R is alkyl (carbon atom number 4).It is described anhydride modified more
Acid anhydrides in first alcohol is 3,3 ', 4,4 '-benzophenone tetracarboxylic dianhydrides；
The anhydride modified polyalcohol synthesis preparation method：By chemical compounds I and II and second catalyst be added reaction
Device, temperature are controlled at 120 DEG C, react 2h, and interval half an hour measures acid value, after acid value is stablized, continue to be added to reactor
Compound III, control temperature react 4h at 120 DEG C, measure acid value, are considered as reaction end when acid value is less than 5mg KOH/g；Institute
It is tetraethylammonium bromide to state the second catalyst.
The bisphenol A epoxide resin, epoxy-ester 0.4 account for the 40% of component B total weights.
The chain extender is resorcinol two (2- ethoxys) ether, accounts for the 0.1-10% of component B gross masses, preferably 3%.
Described to urge the first agent for bismuth carboxylate, content is the 0.25% of component A gross masses.
The each component of said components B is uniformly mixed stirring 1 hour at normal temperatures, is then allowed to stand 1 hour and obtains solid-like
The component B of state.
Embodiment 2
The embodiment of the present invention 2 is described, and the invention further relates to bi-component solvent-free reaction type polyurethane hot melt adhesive to be used for
The application method of plastic film industry, includes the following steps：
(1) before use, component A and component B are packed with independent foil laminated film sealing container respectively；
(2) process is used, component A and B component are not put into glue-smelting machine and are heated to 100 DEG C of meltings, is pressed by metering pump
Ratio (100：50) being output to static mixing tube mixing or mechanical mixture makes two kinds of components be uniformly mixed, and obtains the bi-component
Solvent-free reaction type polyurethane glue.
(3) 50 DEG C of preheating is carried out to applying gum base materials.
(4) after uniformly mixed polyurethane adhesive being heated to 100 DEG C, pass through the modes pair such as spraying, roller coating, showering, squeezing and coating
Substrate surface is glued.
(5) another base material being bonded will be needed to be bonded by mechanical force realization with gum base materials are applied.
Above-mentioned bi-component solvent-free reaction type polyurethane hot melt adhesive modulus after mixing for 24 hours reaches 1300Mpa.
The above described is only a preferred embodiment of the present invention, not making any form to the technology contents of the present invention
On limitation.It is every according to the technical essence of the invention to any simple modification made by above example, equivalent variations and repair
Decorations, in the range of still falling within technical scheme of the present invention.
Claims (7)
1. a kind of bi-component solvent-free reaction type polyurethane hot melt adhesive applied to electronic appliance industry, which is characterized in that including
Component A and component B：
--- the component A includes performed polymer, auxiliary agent, the first catalyst that side chain or main chain carry isocyanato；Wherein
Performed polymer degree of functionality is more than or equal to 1, isocyano-content 0.1%-30%；
Performed polymer in the component A is that polyisocyanates polymerize generation with polyol b, and wherein polyisocyanates is
Isophorone diisocyanate (IPDI) and methyl diphenylene diisocyanate (MDI) (IPDI by a certain percentage:MDI=0.2-
1) composition, and account for the 30-80% of component A gross masses；The polyol b is that side chain or main chain carry hydroxyl base
One or more compositions of group, including polyether polyol, polyester polyol, hydroxyl value ranging from 60-220mgKOH/g, molecular weight
For 50-2000 dalton, preferably 400-1000 dalton；Wherein polyol b accounts for the 20-70% of component A gross masses；
Auxiliary agent in the component A includes antifoaming agent, levelling agent, antioxidant, and additive amount is the 0.1-5% of component A total weights；Institute
It is non-silicone high molecular polymer to state antifoaming agent, and the levelling agent is Siloxane-Oxyalkylene Copolymers compound, and the antioxidant is
Hinered phenols；
First catalyst includes triethylenediamine, bis- (dimethylaminoethyl) ethers and dibutyl tin laurate, bismuth carboxylate
One or more compositions, preferably bismuth carboxylate, content are the 0.01-0.5% of component A gross masses；
The synthesis technology of the component A is：Polyol b, MDI, IPDI and the first catalyst, control is added to reaction kettle
Temperature of charge reacts 1-2h at 40-50 DEG C；60-70 DEG C, react 1-2h；80-100 DEG C, 1-4h is reacted, specified viscosity is reached
(2000-20000cps/120 DEG C, preferably 5000-10000cps/120 DEG C), then auxiliary agent is added into reaction kettle, 80-100 DEG C is stirred
40 DEG C of termination reactions are cooled to after mixing 0.5-1h, and 400 mesh filter screen filtering and dischargings are to form the component A finished products of solid state；
--- the component B is urged comprising anhydride modified polyalcohol, polyol a, bisphenol A epoxide resin, chain extender, amine
Agent, uniform stirring mixes each component at normal temperatures；
Anhydride modified polyalcohol accounts for the 5-60% of component B total weights in the component B；
Polyol a in the component B is one or more compositions that side chain or main chain carry hydroxyl group, including
Polyether polyol, polyester polyol, molecular weight are 500-4000 dalton, preferably 500-2000 dalton, hydroxyl value ranging from 10-
250mgKOH/g accounts for the 10-70% of component B total weights；
The bisphenol A epoxide resin, epoxy-ester 0.2-0.6 account for the 5-60% of component B total weights；
The chain extender is 4,4'- diamino -3,3'- dichloro diphenyl methanes, and 2,4- diamino -3,5- dimethyl sulphur-based toluene are sweet
Oil, hydroquinone two hydroxy ethyl ether, one or more compositions in resorcinol two (2- ethoxys) ether account for the total matter of component B
The 0.1-10% of amount, preferably 1-5%；
The amines catalyst includes N, N- dimethyl cyclohexyl amines, N, and one kind in N- dimethyl benzylamines or composition account for component B
The 0.01-1% of gross mass.
2. a kind of bi-component solvent-free reaction type polyurethane applied to electronic appliance industry heats according to claim 1
Glue, it is characterised in that：Shown in anhydride modified polyalcohol synthesis schematically as follows in the component B：
R ', R1, R2For alkyl, aryl；Or alkyl, the aryl replaced with methacryloxy or vinyl；Or alcoxyl
Base, phenoxy group；Optimizing alkyl (carbon atom number 1-5) or aryl (carbon atom number 6-10)；X is NH3-, OH-, SH- etc.；R
For alkyl (carbon atom number 1-20) or aryl (carbon atom number 6-20).
3. a kind of bi-component solvent-free reaction type polyurethane applied to electronic appliance industry heats according to claim 1
Glue, it is characterised in that：Acid anhydrides used in the anhydride modified polyalcohol is phthalic anhydride, maleic anhydride, tetrahydrochysene O-phthalic
Acid anhydrides, hexahydrophthalic anhydride, 3- methyl and 4- methylhexahydrophthalic anhydrides, 3- methyl and 4- ethyl hexahydro neighbours benzene two
Formic anhydride, itaconic anhydride, succinic anhydride, the eleventh of the twelve Earthly Branches dicarboxylic anhydride, adipic anhydride, carbic anhydride, methylnadic anhydride, hydrogenating methyl
Carbic anhydride, poly- azelaic acid acid anhydride, poly sebacic polyanhydride, poly- icosane diacid anhydride, trimellitic anhydride, Pyromellitic Acid two
Acid anhydride, 3,3 ', any one in 4,4 '-benzophenone tetracarboxylic dianhydrides.
4. a kind of bi-component solvent-free reaction type polyurethane applied to electronic appliance industry heats according to claim 2
Glue, it is characterised in that：The anhydride modified polyalcohol synthesis preparation method is：By chemical compounds I and II and second catalyst add
Enter reactor, temperature is controlled at 80-120 DEG C, reacts 1-4h, and interval half an hour measures acid value, after acid value is stablized, continue to
Composition III is added in reactor, and control temperature measures acid value in 80 DEG C of -140 DEG C of reaction 1-6h, when acid value is less than 10mg KOH/
It is considered as reaction end when g, preferably smaller than 5mg KOH/g；Second catalyst be triethylamine, trimethyl benzyl ammonia chloride, N,
N- dimethyl benzylamines, N, N- dimethylbenzyls aniline, trimethyl benzyl ammonia chloride, triphenylphosphine, antimony triphenyl, cetylacetone metallic
Any one in complex compound, tetraethylammonium bromide, pyridine or dimethylamino naphthyridine or several mixture.
5. a kind of bi-component solvent-free reaction type polyurethane adhesive is applied to the application method of woodworking, it is characterised in that：
Include the following steps：
(1) before use, component A and component B are packed with independent sealing container respectively, the sealing container includes but unlimited
In tinplate bucket, PET/Al/Nylon/PP films etc. or combinations thereof；
(2) use process, component A and B component are not put into glue-smelting machine be heated to 80-120 DEG C melting, by metering pump press than
Example, which is output to static mixing tube mixing or mechanical mixture, makes two kinds of components be uniformly mixed, and obtains the bi-component solvent-free reaction
Type polyurethane glue；
(3) reach 40-50 DEG C to applying gum base materials and carrying out being preheated to substrate surface；
(4) after uniformly mixed polyurethane adhesive being heated to 80-120 DEG C, by modes such as spraying, roller coating, showering, squeezing and coating to base
Material surface is glued；
(5) another base material being bonded will be needed to be bonded by mechanical force realization with gum base materials are applied.
6. the application method according to claim 5, it is characterised in that：The ratio of the component A and component B is 1：0.3~
1：0.5.
7. the application method according to claim 5, it is characterised in that：The bi-component solvent-free reaction type polyurethane hot melt
Glue modulus after mixing for 24 hours reaches 200-1500Mpa.
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| EP4083158A4 (en) * | 2019-12-25 | 2024-01-24 | Mitsui Chemicals, Inc. | POLYURETHANE STRUCTURAL ADHESIVE |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020097900A1 (en) | 2018-11-16 | 2020-05-22 | Dow Global Technologies Llc | Solventless adhesive composition process and laminate with same |
| CN113166620A (en) * | 2018-11-16 | 2021-07-23 | 陶氏环球技术有限责任公司 | Solvent-free adhesive composition method and laminates thereof |
| JP2022518657A (en) * | 2018-11-16 | 2022-03-16 | ダウ グローバル テクノロジーズ エルエルシー | Solvent-free adhesive compositions, processes, and laminates thereof |
| EP3880767A4 (en) * | 2018-11-16 | 2022-06-29 | Dow Global Technologies LLC | Solventless adhesive composition process and laminate with same |
| JP7275265B2 (en) | 2018-11-16 | 2023-05-17 | ダウ グローバル テクノロジーズ エルエルシー | Solventless Adhesive Compositions, Processes, and Laminates Thereof |
| CN113166620B (en) * | 2018-11-16 | 2024-03-08 | 陶氏环球技术有限责任公司 | Solvent-free adhesive composition method and laminates thereof |
| US12157841B2 (en) | 2018-11-16 | 2024-12-03 | Dow Global Technologies Llc | Solventless adhesive composition process and laminate with same |
| TWI696638B (en) * | 2018-12-06 | 2020-06-21 | 財團法人工業技術研究院 | Resin and hot melt adhesive |
| EP4083158A4 (en) * | 2019-12-25 | 2024-01-24 | Mitsui Chemicals, Inc. | POLYURETHANE STRUCTURAL ADHESIVE |
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