SK68695A3 - Moisture-hardening polyurethane fusion adhesive - Google Patents
Moisture-hardening polyurethane fusion adhesive Download PDFInfo
- Publication number
- SK68695A3 SK68695A3 SK686-95A SK68695A SK68695A3 SK 68695 A3 SK68695 A3 SK 68695A3 SK 68695 A SK68695 A SK 68695A SK 68695 A3 SK68695 A3 SK 68695A3
- Authority
- SK
- Slovakia
- Prior art keywords
- polyester
- adhesive
- adhesive according
- glycol
- hot
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 42
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 42
- 239000004814 polyurethane Substances 0.000 title claims abstract description 36
- 229920002635 polyurethane Polymers 0.000 title claims description 33
- 230000004927 fusion Effects 0.000 title abstract 3
- 229920000728 polyester Polymers 0.000 claims abstract description 65
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 58
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 18
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 18
- 229920005989 resin Polymers 0.000 claims abstract description 17
- 239000011347 resin Substances 0.000 claims abstract description 17
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 15
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 13
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- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 239000003381 stabilizer Substances 0.000 claims abstract description 8
- 239000011248 coating agent Substances 0.000 claims abstract description 7
- 238000000576 coating method Methods 0.000 claims abstract description 7
- 239000013032 Hydrocarbon resin Substances 0.000 claims abstract description 6
- 229920006270 hydrocarbon resin Polymers 0.000 claims abstract description 6
- 239000000155 melt Substances 0.000 claims abstract description 6
- 238000010586 diagram Methods 0.000 claims abstract description 3
- 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 abstract description 3
- 239000004831 Hot glue Substances 0.000 claims description 72
- 239000000463 material Substances 0.000 claims description 18
- 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 15
- -1 halogenation Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 239000010985 leather Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
- 239000010410 layer Substances 0.000 claims description 6
- 238000013008 moisture curing Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 3
- 238000007788 roughening Methods 0.000 claims description 3
- HEBTZZBBPUFAFE-UHFFFAOYSA-N 2-methyl-n-(oxomethylidene)benzenesulfonamide Chemical group CC1=CC=CC=C1S(=O)(=O)N=C=O HEBTZZBBPUFAFE-UHFFFAOYSA-N 0.000 claims description 2
- 229920006272 aromatic hydrocarbon resin Polymers 0.000 claims description 2
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- 238000005658 halogenation reaction Methods 0.000 claims description 2
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- 239000000654 additive Substances 0.000 abstract description 8
- 238000001035 drying Methods 0.000 abstract description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 20
- 150000002009 diols Chemical class 0.000 description 17
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 230000007704 transition Effects 0.000 description 13
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 12
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- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 4
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 4
- 229930006722 beta-pinene Natural products 0.000 description 4
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
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- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 3
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- 238000012545 processing Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
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- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
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- 239000004922 lacquer Substances 0.000 description 2
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- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000008092 positive effect Effects 0.000 description 2
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- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- SDAMTPCXBPNEQC-UHFFFAOYSA-N 3,4-dimethylphthalic acid Chemical compound CC1=CC=C(C(O)=O)C(C(O)=O)=C1C SDAMTPCXBPNEQC-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 241000845082 Panama Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 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 description 1
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
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- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
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- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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- 229920001187 thermosetting polymer Polymers 0.000 description 1
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- 239000005028 tinplate Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
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- 239000003440 toxic substance Substances 0.000 description 1
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- 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 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-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
-
- 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
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/26—Natural polymers, natural resins or derivatives thereof according to C08L1/00 - C08L5/00, C08L89/00, C08L93/00, C08L97/00 or C08L99/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S528/905—Polymer prepared from isocyanate reactant has adhesive property
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)
- Paints Or Removers (AREA)
- Processing Of Solid Wastes (AREA)
- Disintegrating Or Milling (AREA)
- Polyesters Or Polycarbonates (AREA)
- Footwear And Its Accessory, Manufacturing Method And Apparatuses (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/982,203 US6136136A (en) | 1992-11-25 | 1992-11-25 | Moisture-curable polyurethane hotmelt adhesives with high green strength |
| PCT/EP1993/003216 WO1994012552A1 (de) | 1992-11-25 | 1993-11-16 | Feuchtigkeitshärtender polyurethan-schmelzklebstoff |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK68695A3 true SK68695A3 (en) | 1995-10-11 |
Family
ID=25528936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK686-95A SK68695A3 (en) | 1992-11-25 | 1993-11-16 | Moisture-hardening polyurethane fusion adhesive |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US6136136A (no) |
| EP (1) | EP0670853B1 (no) |
| JP (1) | JPH08503513A (no) |
| KR (1) | KR100287577B1 (no) |
| CN (1) | CN1056169C (no) |
| AT (1) | ATE170197T1 (no) |
| AU (1) | AU675473B2 (no) |
| BG (1) | BG99510A (no) |
| BR (1) | BR9307524A (no) |
| CA (1) | CA2150228A1 (no) |
| CZ (1) | CZ287996B6 (no) |
| DE (1) | DE59308935D1 (no) |
| DK (1) | DK0670853T3 (no) |
| ES (1) | ES2119998T3 (no) |
| FI (1) | FI952538A0 (no) |
| HK (1) | HK1004487A1 (no) |
| HU (1) | HU216659B (no) |
| LV (1) | LV11476B (no) |
| MX (1) | MX9307374A (no) |
| NO (1) | NO309682B1 (no) |
| PL (1) | PL176121B1 (no) |
| RU (1) | RU2113450C1 (no) |
| SK (1) | SK68695A3 (no) |
| WO (1) | WO1994012552A1 (no) |
| ZA (1) | ZA938798B (no) |
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| US20070193179A1 (en) * | 2006-01-27 | 2007-08-23 | Prolam, Societe En Commandite | Wooden laminated floor product to improve strength, water protection and fatigue resistance |
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| CA2605215C (en) * | 2006-10-02 | 2014-12-02 | Prolam, Societe En Commandite | Utilization of coloration to improve the detection of "hit or miss" defects when using scanner equipment and an automated saw to remove defects in wood pieces |
| US9579869B2 (en) * | 2009-02-17 | 2017-02-28 | Henkel IP & Holding GmbH | Liquid moisture curable polyurethane adhesives for lamination and assembly |
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| JP2011001465A (ja) * | 2009-06-18 | 2011-01-06 | Yokohama Rubber Co Ltd:The | 反応性ホットメルト接着剤 |
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| WO2014014499A1 (en) | 2012-07-16 | 2014-01-23 | Dow Global Technologies Llc | Curable compositions containing isocyanate functional components and amorphous linear polymers, adhesives therof |
| TWI600737B (zh) * | 2013-01-22 | 2017-10-01 | 東洋油墨Ｓｃ控股股份有限公司 | 接著劑組成物、以及積層體及其製造方法 |
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| JP6196851B2 (ja) * | 2013-09-06 | 2017-09-13 | 積水フーラー株式会社 | 湿気硬化型ホットメルト接着剤 |
| CN103645288A (zh) * | 2013-11-16 | 2014-03-19 | 中山欧麦克仪器设备有限公司 | 一种多功能便携式水质检测分析仪 |
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| JP6636943B2 (ja) | 2014-05-15 | 2020-01-29 | ノヴァラング ゲゼルシャフト ミット ベシュレンクテル ハフツング | 医療技術的測定装置、及び測定方法 |
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| CN104479617B (zh) * | 2014-12-17 | 2018-06-12 | 广东菲安妮皮具股份有限公司 | 高抗刮性皮革粘合剂 |
| WO2016154191A1 (en) * | 2015-03-24 | 2016-09-29 | Chen Zhijin | Two-part urethane adhesive |
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| US10336925B2 (en) | 2015-09-08 | 2019-07-02 | Resinate Materials Group, Inc. | Polyester polyols for reactive hot-melt adhesives |
| EP3159026A1 (de) | 2015-10-23 | 2017-04-26 | novalung GmbH | Zwischenelement für eine medizintechnische extrakorporale fluidleitung, medizintechnisches extrakorporales fluidsystem und verfahren zum messen eines in einem medizintechnischen extrakorporalen fluidsystem geführten fluid des menschlichen oder tierischen körpers enthaltenen gases |
| KR102286769B1 (ko) * | 2016-11-01 | 2021-08-09 | 현대모비스 주식회사 | 핫멜트 접착제 조성물, 이의 제조방법 및 자동차용 헤드램프 |
| EP3757143B1 (en) * | 2018-05-14 | 2022-01-05 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Polyurethane prepolymer, adhesive and synthetic imitation leather |
| EP3841177A4 (en) * | 2018-08-23 | 2022-04-06 | Henkel AG & Co. KGaA | Moisture curable polyurethane adhesive composition |
| EP4051747A4 (en) * | 2019-10-30 | 2023-11-22 | Henkel AG & Co. KGaA | HOT MELT POLYURETHANE ADHESIVE FOR LOW TEMPERATURE APPLICATION |
| JP2022011881A (ja) * | 2020-06-30 | 2022-01-17 | 東洋インキＳｃホールディングス株式会社 | ポリイソシアネート組成物の製造方法 |
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-
1992
- 1992-11-25 US US07/982,203 patent/US6136136A/en not_active Expired - Lifetime
-
1993
- 1993-11-16 US US08/436,320 patent/US5599895A/en not_active Expired - Lifetime
- 1993-11-16 WO PCT/EP1993/003216 patent/WO1994012552A1/de active IP Right Grant
- 1993-11-16 RU RU95117110A patent/RU2113450C1/ru active
- 1993-11-16 EP EP94901808A patent/EP0670853B1/de not_active Expired - Lifetime
- 1993-11-16 ES ES94901808T patent/ES2119998T3/es not_active Expired - Lifetime
- 1993-11-16 BR BR9307524-3A patent/BR9307524A/pt active Search and Examination
- 1993-11-16 AT AT94901808T patent/ATE170197T1/de active
- 1993-11-16 PL PL93309227A patent/PL176121B1/pl unknown
- 1993-11-16 CZ CZ19951320A patent/CZ287996B6/cs not_active IP Right Cessation
- 1993-11-16 DE DE59308935T patent/DE59308935D1/de not_active Expired - Lifetime
- 1993-11-16 DK DK94901808T patent/DK0670853T3/da active
- 1993-11-16 JP JP6512712A patent/JPH08503513A/ja not_active Ceased
- 1993-11-16 SK SK686-95A patent/SK68695A3/sk unknown
- 1993-11-16 KR KR1019950702093A patent/KR100287577B1/ko not_active Expired - Fee Related
- 1993-11-16 CA CA002150228A patent/CA2150228A1/en not_active Abandoned
- 1993-11-16 AU AU56248/94A patent/AU675473B2/en not_active Ceased
- 1993-11-16 HU HU9501527A patent/HU216659B/hu not_active IP Right Cessation
- 1993-11-24 ZA ZA938798A patent/ZA938798B/xx unknown
- 1993-11-24 MX MX9307374A patent/MX9307374A/es not_active IP Right Cessation
- 1993-11-25 CN CN93121256A patent/CN1056169C/zh not_active Expired - Fee Related
-
1995
- 1995-03-20 BG BG99510A patent/BG99510A/bg unknown
- 1995-04-03 NO NO951278A patent/NO309682B1/no not_active IP Right Cessation
- 1995-05-24 FI FI952538A patent/FI952538A0/fi not_active Application Discontinuation
- 1995-05-25 LV LVP-95-141A patent/LV11476B/lv unknown
-
1998
- 1998-05-02 HK HK98103758A patent/HK1004487A1/xx not_active IP Right Cessation
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