CA2389258C - Improved reactive hot melt adhesive - Google Patents
Improved reactive hot melt adhesive Download PDFInfo
- Publication number
- CA2389258C CA2389258C CA2389258A CA2389258A CA2389258C CA 2389258 C CA2389258 C CA 2389258C CA 2389258 A CA2389258 A CA 2389258A CA 2389258 A CA2389258 A CA 2389258A CA 2389258 C CA2389258 C CA 2389258C
- Authority
- CA
- Canada
- Prior art keywords
- polyol
- composition
- polyester
- tackifying resin
- grams
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000004831 Hot glue Substances 0.000 title claims abstract description 19
- 229920005989 resin Polymers 0.000 claims abstract description 116
- 239000011347 resin Substances 0.000 claims abstract description 116
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 94
- 239000012948 isocyanate Substances 0.000 claims abstract description 80
- -1 isocyanate compound Chemical class 0.000 claims abstract description 74
- 230000001070 adhesive effect Effects 0.000 claims abstract description 61
- 239000000853 adhesive Substances 0.000 claims abstract description 60
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 60
- 229920005862 polyol Polymers 0.000 claims abstract description 58
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 150000003077 polyols Chemical class 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims description 48
- 239000000178 monomer Substances 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 150000002513 isocyanates Chemical class 0.000 claims description 21
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 18
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 17
- 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 11
- 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 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 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 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 8
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 claims description 7
- 239000000539 dimer Substances 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- QYMGIIIPAFAFRX-UHFFFAOYSA-N butyl prop-2-enoate;ethene Chemical compound C=C.CCCCOC(=O)C=C QYMGIIIPAFAFRX-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229920006026 co-polymeric resin Polymers 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- 229920006272 aromatic hydrocarbon resin Polymers 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- 229920001748 polybutylene Polymers 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 19
- 239000012943 hotmelt Substances 0.000 abstract description 19
- 239000000126 substance Substances 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 229920003023 plastic Polymers 0.000 abstract description 4
- 239000004033 plastic Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 description 30
- ZMSQJSMSLXVTKN-UHFFFAOYSA-N 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine Chemical compound C1COCCN1CCOCCN1CCOCC1 ZMSQJSMSLXVTKN-UHFFFAOYSA-N 0.000 description 29
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical class C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 21
- 229940125782 compound 2 Drugs 0.000 description 17
- 229940125904 compound 1 Drugs 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 11
- 229920003314 Elvaloy® Polymers 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- 238000001723 curing Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- KIOWHOMJXAQSMW-UHFFFAOYSA-N phenol;4,6,6-trimethylbicyclo[3.1.1]hept-3-ene Chemical compound OC1=CC=CC=C1.CC1=CCC2C(C)(C)C1C2 KIOWHOMJXAQSMW-UHFFFAOYSA-N 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
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- CJDPJFRMHVXWPT-UHFFFAOYSA-N barium sulfide Chemical compound [S-2].[Ba+2] CJDPJFRMHVXWPT-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 150000004072 triols Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920003345 Elvax® Polymers 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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- 239000012298 atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
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- 239000000835 fiber Substances 0.000 description 2
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- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000013008 moisture curing Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
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- 239000000565 sealant Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
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- 150000003505 terpenes Chemical class 0.000 description 2
- 235000007586 terpenes Nutrition 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
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- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B7/00—Mixing; Kneading
- B29B7/30—Mixing; Kneading continuous, with mechanical mixing or kneading devices
- B29B7/58—Component parts, details or accessories; Auxiliary operations
- B29B7/72—Measuring, controlling or regulating
- B29B7/726—Measuring properties of mixture, e.g. temperature or density
-
- 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
- C08G18/4027—Mixtures of compounds of group C08G18/54 with other macromolecular compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/453,361 US6387449B1 (en) | 1999-12-01 | 1999-12-01 | Reactive hot melt adhesive |
| US09/453,361 | 1999-12-01 | ||
| PCT/US2000/032641 WO2001040343A1 (en) | 1999-12-01 | 2000-12-01 | Improved reactive hot melt adhesive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2389258A1 CA2389258A1 (en) | 2001-06-07 |
| CA2389258C true CA2389258C (en) | 2011-02-08 |
Family
ID=23800275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2389258A Expired - Fee Related CA2389258C (en) | 1999-12-01 | 2000-12-01 | Improved reactive hot melt adhesive |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6387449B1 (enExample) |
| EP (1) | EP1237973B1 (enExample) |
| JP (1) | JP4699669B2 (enExample) |
| CN (1) | CN1185273C (enExample) |
| AU (1) | AU2054501A (enExample) |
| CA (1) | CA2389258C (enExample) |
| DE (1) | DE60004265T2 (enExample) |
| MX (1) | MXPA02005305A (enExample) |
| WO (1) | WO2001040343A1 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030022973A1 (en) * | 2001-04-13 | 2003-01-30 | Ju-Ming Hung | Moisture cured polyurethane hot melt adhesives with reactive tackifiers |
| US6613836B2 (en) * | 2001-06-15 | 2003-09-02 | National Starch And Chemical Investment Holding Corporation | Reactive hot melt adhesive |
| DK1361236T3 (da) * | 2002-04-25 | 2005-04-25 | Sicpa Holding Sa | En polyurethanharpiks afledt af polyhydroxylerede harpikser |
| US20060014917A1 (en) * | 2002-05-16 | 2006-01-19 | Mcp Industries, Inc. | Moisture-curing polyurethane material having a long gel time |
| US20040072953A1 (en) * | 2002-10-15 | 2004-04-15 | Ju-Ming Hung | Reactive hot melt adhesive with non-polymeric aliphatic difunctionals |
| US20060210808A1 (en) * | 2002-10-15 | 2006-09-21 | Ju-Ming Hung | Reactive hot melt adhesive with non-polymeric aliphatic difunctionals |
| JP4560702B2 (ja) * | 2002-12-13 | 2010-10-13 | 東洋紡績株式会社 | 印刷インクアンカーコート用接着剤組成物、多層複合フィルムおよび包装容器 |
| US6803412B2 (en) * | 2003-03-13 | 2004-10-12 | H.B. Fuller Licensing & Financing Inc. | Moisture curable hot melt sealants for glass constructions |
| US7189781B2 (en) * | 2003-03-13 | 2007-03-13 | H.B. Fuller Licensing & Finance Inc. | Moisture curable, radiation curable sealant composition |
| US8664330B2 (en) | 2003-04-04 | 2014-03-04 | Henkel US IP LLC | Reactive hot melt adhesive with improved hydrolysis resistance |
| WO2006014786A1 (en) * | 2004-07-28 | 2006-02-09 | Henkel Corporation | Dual cure compositions employing free radical and rtv cure |
| JP4831522B2 (ja) * | 2004-10-28 | 2011-12-07 | 日本ポリウレタン工業株式会社 | 反応性ホットメルト接着剤の製造システムおよび製造方法 |
| US7625963B2 (en) * | 2007-01-25 | 2009-12-01 | Henkel Ag & Co. Kgaa | Reactive hot melt adhesive with bituminous additive |
| US7914895B2 (en) * | 2007-05-24 | 2011-03-29 | H.B. Fuller Company | Moisture curable hot melt adhesive composition |
| JP5580982B2 (ja) | 2008-11-27 | 2014-08-27 | ヘンケル コーポレイション | 湿気硬化型ホットメルト接着剤 |
| JP2013506063A (ja) * | 2009-05-22 | 2013-02-21 | プロテクト テクノロジーズ インコーポレーテッド | 遠隔活性化ロックシステムと方法 |
| US20110081490A1 (en) * | 2009-10-05 | 2011-04-07 | Brian Comeau | Methods of curing polyurea prepolymers for golf balls |
| US20110081492A1 (en) * | 2009-10-05 | 2011-04-07 | Michael Michalewich | Methods of curing polyurethane prepolymers for golf balls |
| US20110081497A1 (en) * | 2009-10-05 | 2011-04-07 | Brian Comeau | Methods of curing polyurea prepolymers for golf balls |
| CN102051152A (zh) * | 2009-11-09 | 2011-05-11 | 上海天希化工有限公司 | 一种活性热熔性粘合剂及其制备方法 |
| JP2011116817A (ja) * | 2009-12-01 | 2011-06-16 | Henkel Japan Ltd | 湿気硬化型ホットメルト接着剤 |
| CA2834866C (en) | 2011-05-12 | 2019-06-11 | H.B. Fuller Company | Hot melt moisture cure adhesive compositions |
| KR20140044867A (ko) | 2011-07-22 | 2014-04-15 | 에이치. 비. 풀러, 컴퍼니 | 전자장치 상에 사용하기 위한 ２파트 이중 경화 접착제 |
| CN103703087B (zh) | 2011-07-22 | 2015-09-09 | H.B.富勒公司 | 用在电子器件上的单组分双固化粘合剂 |
| TWI534165B (zh) | 2011-10-24 | 2016-05-21 | 迪愛生股份有限公司 | 濕氣硬化型聚胺基甲酸酯熱熔樹脂組成物、接著劑及物品 |
| EP2970727B1 (en) * | 2013-03-14 | 2022-02-02 | Basf Se | Hot melt adhesive and method of forming the same |
| KR101480044B1 (ko) | 2014-03-24 | 2015-01-13 | 주식회사 오공 | 제본용 핫멜트 접착제 조성물 |
| WO2015164017A1 (en) * | 2014-04-22 | 2015-10-29 | Exxonmobil Chemical Patents Inc. | Hydrocarbon tackifiers for adhesive compositions |
| DE102014217783A1 (de) * | 2014-09-05 | 2016-03-10 | Evonik Degussa Gmbh | Zweikomponentiger Polyurethanschmelzklebstoff mit hoher Anfangs- und Endfestigkeit |
| US10336925B2 (en) | 2015-09-08 | 2019-07-02 | Resinate Materials Group, Inc. | Polyester polyols for reactive hot-melt adhesives |
| EP3347396A1 (en) | 2015-09-08 | 2018-07-18 | Resinate Materials Group, Inc. | Polyester polyols for reactive hot-melt adhesives |
| EP3363840A1 (en) | 2017-02-17 | 2018-08-22 | Henkel AG & Co. KGaA | Two-component polyurethane composition comprising a latent catalyst |
| CN110194940B (zh) * | 2018-02-26 | 2022-04-15 | H.B.富乐公司 | 热熔压敏粘合剂组合物及其制备方法 |
| CN108753235A (zh) * | 2018-05-28 | 2018-11-06 | 东莞华工佛塑新材料有限公司 | 一种软包装锂离子电池折边用反应型聚氨酯热熔胶 |
| CN109096977A (zh) * | 2018-07-04 | 2018-12-28 | 滁州环球聚氨酯科技有限公司 | 一种热稳定性好的胶黏剂的制备方法 |
| ES2919426T3 (es) * | 2018-10-15 | 2022-07-26 | Henkel Ag & Co Kgaa | Composición adhesiva termofusible que comprende polioles de poliéster de origen biológico |
| US12331192B2 (en) | 2019-04-05 | 2025-06-17 | Sika Technology Ag | Dimer fatty acid-polyester diol-based polymer, containing isocyanate groups |
| EP4021706A1 (en) | 2019-08-26 | 2022-07-06 | H.B. Fuller Company | Fast set moisture curable hot melt adhesive composition and articles including the same |
| CN111267439A (zh) * | 2020-02-25 | 2020-06-12 | 十倍好智能家居(广州)有限公司 | 板材、板材的制备方法和板材的使用方法 |
| CN111234768B (zh) * | 2020-03-26 | 2022-02-18 | 重庆中科力泰高分子材料股份有限公司 | 粘接非极性材料的聚氨酯热熔胶及其制备方法 |
| CN111286293B (zh) * | 2020-04-10 | 2021-12-03 | 厦门马特高科新能源有限公司 | 一种蓄电池pp塑壳胶黏剂及其制备方法 |
| US20240343957A1 (en) * | 2021-08-20 | 2024-10-17 | Dow Global Technologies Llc | High green strength reactive hot melt adhesives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3767040A (en) | 1971-03-01 | 1973-10-23 | Minnesota Mining & Mfg | Pressure-sensitive polyurethane adhesives |
| JPS5365333A (en) | 1976-11-25 | 1978-06-10 | Hitachi Chem Co Ltd | Undercoating compounds for adhesive tapes |
| US4775719A (en) | 1986-01-29 | 1988-10-04 | H. B. Fuller Company | Thermally stable hot melt moisture-cure polyurethane adhesive composition |
| US4808255A (en) | 1987-05-07 | 1989-02-28 | H. B. Fuller Company | Thermally stable reactive hot melt urethane adhesive composition having a thermoplastic polymer, a compatible, curing urethane polyester polyol prepolymer and a tackifying agent |
| JPH03111475A (ja) | 1989-09-27 | 1991-05-13 | Sekisui Chem Co Ltd | 反応性ホットメルト型接着剤組成物 |
| DE3933204C2 (de) | 1989-10-05 | 1994-05-26 | Jowat Lobers U Frank Gmbh & Co | Reaktivschmelzkleber |
| CA2116872C (en) | 1992-07-02 | 2001-02-27 | Mary E. Foster | Hot melt adhesive composition |
| JPH0635386A (ja) * | 1992-07-22 | 1994-02-10 | Bando Chem Ind Ltd | 電子写真複写機用クリーニングブレードの製法 |
| US5472785A (en) * | 1994-04-12 | 1995-12-05 | Minnesota Mining And Manufacturing Company | Reactive wax-containing moisture curable hot melt composition |
| JP4055216B2 (ja) * | 1996-12-28 | 2008-03-05 | ヤスハラケミカル株式会社 | 湿気硬化型反応性ホットメルト接着剤組成物 |
| JPH11124560A (ja) * | 1997-10-27 | 1999-05-11 | Toyo Ink Mfg Co Ltd | 反応型ホットメルト接着剤 |
| JP4023920B2 (ja) * | 1998-08-04 | 2007-12-19 | 東洋インキ製造株式会社 | 反応性ホットメルト接着剤 |
-
1999
- 1999-12-01 US US09/453,361 patent/US6387449B1/en not_active Expired - Lifetime
-
2000
- 2000-12-01 WO PCT/US2000/032641 patent/WO2001040343A1/en not_active Ceased
- 2000-12-01 JP JP2001541095A patent/JP4699669B2/ja not_active Expired - Fee Related
- 2000-12-01 DE DE60004265T patent/DE60004265T2/de not_active Expired - Lifetime
- 2000-12-01 AU AU20545/01A patent/AU2054501A/en not_active Abandoned
- 2000-12-01 EP EP00983835A patent/EP1237973B1/en not_active Expired - Lifetime
- 2000-12-01 MX MXPA02005305A patent/MXPA02005305A/es active IP Right Grant
- 2000-12-01 CN CNB008164908A patent/CN1185273C/zh not_active Expired - Fee Related
- 2000-12-01 CA CA2389258A patent/CA2389258C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1237973B1 (en) | 2003-07-30 |
| CN1402743A (zh) | 2003-03-12 |
| EP1237973A1 (en) | 2002-09-11 |
| JP4699669B2 (ja) | 2011-06-15 |
| CN1185273C (zh) | 2005-01-19 |
| AU2054501A (en) | 2001-06-12 |
| JP2003515637A (ja) | 2003-05-07 |
| US6387449B1 (en) | 2002-05-14 |
| MXPA02005305A (es) | 2003-04-10 |
| CA2389258A1 (en) | 2001-06-07 |
| WO2001040343A1 (en) | 2001-06-07 |
| DE60004265T2 (de) | 2004-04-22 |
| DE60004265D1 (de) | 2003-09-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20151201 |