DE60030242T2 - Reaktiver heissschmelzkleber mit hoher anfangsfestigkeit hergestellt durch prepolymerisierung im hauptreaktor - Google Patents
Reaktiver heissschmelzkleber mit hoher anfangsfestigkeit hergestellt durch prepolymerisierung im hauptreaktor Download PDFInfo
- Publication number
- DE60030242T2 DE60030242T2 DE60030242T DE60030242T DE60030242T2 DE 60030242 T2 DE60030242 T2 DE 60030242T2 DE 60030242 T DE60030242 T DE 60030242T DE 60030242 T DE60030242 T DE 60030242T DE 60030242 T2 DE60030242 T2 DE 60030242T2
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- polyols
- prepolymer
- reactive hot
- diisocyanate
- 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 - Lifetime
Links
- 239000000853 adhesive Substances 0.000 title description 10
- 230000001070 adhesive effect Effects 0.000 title description 10
- 229920005862 polyol Polymers 0.000 claims abstract description 29
- 150000003077 polyols Chemical class 0.000 claims abstract description 29
- 229920000728 polyester Polymers 0.000 claims abstract description 26
- 239000004831 Hot glue Substances 0.000 claims abstract description 19
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 15
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 15
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 229920000642 polymer Polymers 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- GPCIDUIBGGUBJG-UHFFFAOYSA-N hexanedioic acid;hexane-1,1-diol Chemical compound CCCCCC(O)O.OC(=O)CCCCC(O)=O GPCIDUIBGGUBJG-UHFFFAOYSA-N 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 229920003054 adipate polyester Polymers 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 239000004970 Chain extender Substances 0.000 claims description 2
- 229930182556 Polyacetal Natural products 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 239000002318 adhesion promoter Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 229920001281 polyalkylene Polymers 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920006324 polyoxymethylene Polymers 0.000 claims description 2
- 229920005992 thermoplastic resin Polymers 0.000 claims description 2
- XDGWKBYFXMRODP-UHFFFAOYSA-N 4-[2-[2-(2,6-dimethylmorpholin-4-yl)ethoxy]ethyl]-2,6-dimethylmorpholine Chemical compound C1C(C)OC(C)CN1CCOCCN1CC(C)OC(C)C1 XDGWKBYFXMRODP-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims 1
- 229920006295 polythiol Polymers 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 4
- 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 description 13
- 229920001610 polycaprolactone Polymers 0.000 description 8
- 239000004632 polycaprolactone Substances 0.000 description 8
- 238000012936 correction and preventive action Methods 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000012943 hotmelt Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- -1 hexanediol dodecane Chemical compound 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- ZGDSDWSIFQBAJS-UHFFFAOYSA-N 1,2-diisocyanatopropane Chemical compound O=C=NC(C)CN=C=O ZGDSDWSIFQBAJS-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 1
- ZVEMLYIXBCTVOF-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(C(C)(C)N=C=O)=C1 ZVEMLYIXBCTVOF-UHFFFAOYSA-N 0.000 description 1
- BWSRWWPISOBDNX-UHFFFAOYSA-N 1-ethenyl-3-(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C=C)=C1 BWSRWWPISOBDNX-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- DUFKCOQISQKSAV-UHFFFAOYSA-N Polypropylene glycol (m w 1,200-3,000) Chemical compound CC(O)COC(C)CO DUFKCOQISQKSAV-UHFFFAOYSA-N 0.000 description 1
- 238000003723 Smelting Methods 0.000 description 1
- 229920013701 VORANOL™ Polymers 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- VJKKCRAXPXYVHP-UHFFFAOYSA-N hexane-1,1-diol;nonanedioic acid Chemical compound CCCCCC(O)O.OC(=O)CCCCCCCC(O)=O VJKKCRAXPXYVHP-UHFFFAOYSA-N 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 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
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2250/00—Compositions for preparing crystalline polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/326,855 US6365700B1 (en) | 1999-06-07 | 1999-06-07 | High green strength reactive hot melt by a prepolymerization in the main reactor |
| US326855 | 1999-06-07 | ||
| PCT/US2000/015604 WO2000075209A1 (en) | 1999-06-07 | 2000-06-07 | High green strength reactive hot melt by a prepolymerization in the main reactor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60030242D1 DE60030242D1 (de) | 2006-10-05 |
| DE60030242T2 true DE60030242T2 (de) | 2006-12-14 |
Family
ID=23274016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60030242T Expired - Lifetime DE60030242T2 (de) | 1999-06-07 | 2000-06-07 | Reaktiver heissschmelzkleber mit hoher anfangsfestigkeit hergestellt durch prepolymerisierung im hauptreaktor |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6365700B1 (enExample) |
| EP (1) | EP1112296B1 (enExample) |
| JP (1) | JP2003501529A (enExample) |
| AT (1) | ATE337349T1 (enExample) |
| AU (1) | AU5468000A (enExample) |
| CA (1) | CA2339822C (enExample) |
| DE (1) | DE60030242T2 (enExample) |
| ES (1) | ES2265947T3 (enExample) |
| WO (1) | WO2000075209A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19961941A1 (de) * | 1999-12-22 | 2001-07-05 | Henkel Kgaa | Polyurethan-Zusammensetzungen auf der Basis von Polyether-Copolymeren |
| US7074297B2 (en) * | 2000-09-21 | 2006-07-11 | Rohm And Haas Company | Method for forming a hot melt adhesive |
| TW200407390A (en) * | 2002-09-03 | 2004-05-16 | Rohm & Haas | Reactive hot-melt adhesive compositions with improved adhesion to difficult substrates |
| JP4279155B2 (ja) * | 2003-05-13 | 2009-06-17 | ローム アンド ハース カンパニー | 湿分反応性ホットメルト接着剤 |
| MXPA06002031A (es) * | 2003-08-22 | 2006-05-31 | Dow Global Technologies Inc | Composicion util como adhesivo para instalar ventanas en vehiculos. |
| US20050192387A1 (en) * | 2004-03-01 | 2005-09-01 | Williams David A. | RTV silicone composition offering rapid bond strength |
| US7361292B2 (en) * | 2004-11-08 | 2008-04-22 | Dow Global Technologies Inc. | High modulus, nonconductive adhesive useful for installing vehicle windows |
| DE102004057292A1 (de) * | 2004-11-26 | 2006-06-01 | Klebchemie, M.G. Becker Gmbh & Co Kg | Verfahren zur Herstellung von reaktiven Polyurethanzusammensetzungen |
| US20070244249A1 (en) * | 2006-04-06 | 2007-10-18 | General Electric Company | Two-part translucent silicone rubber-forming composition |
| US20090159206A1 (en) * | 2007-12-20 | 2009-06-25 | National Starch And Chemical Investment Holding Corporation | Moisture curable hot melt adhesive |
| CN101570676B (zh) * | 2009-06-04 | 2012-01-04 | 长兴三伟热熔胶有限公司 | 一种衬布用聚氨酯热熔胶及其制备方法 |
| CN102965064B (zh) * | 2012-11-27 | 2014-03-19 | 上海汇得化工有限公司 | 一种无溶剂聚氨酯胶粘剂制备及其应用 |
| ES2755097T3 (es) * | 2014-05-16 | 2020-04-21 | Henkel Ag & Co Kgaa | Adhesivo de fusión en caliente de poliuretano termoplástico |
| JP6665161B2 (ja) * | 2014-08-15 | 2020-03-13 | エイチ．ビー．フラー カンパニー | リワーク性湿気硬化型ホットメルト接着剤組成物、これを使用する方法およびこれを含む物品 |
| CN107094365B (zh) * | 2016-02-18 | 2019-10-29 | 深圳市汇顶科技股份有限公司 | 模组及其组装方法 |
| KR102162494B1 (ko) * | 2018-03-28 | 2020-10-07 | 주식회사 엘지화학 | 수지 조성물 |
| CN108840992B (zh) * | 2018-05-16 | 2020-06-09 | 中国科学院化学研究所 | 水性油墨组合物、水性油墨树脂及其制备方法和应用 |
| ES3042081T3 (en) | 2019-10-30 | 2025-11-18 | Henkel Ag & Co Kgaa | Polyurethane hot melt adhesive for low temperature application |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3770555A (en) * | 1971-06-14 | 1973-11-06 | Norton Co | Partially cured preformed film and its use in joining overlapped ends of a coated abrasive article |
| GB1554102A (en) * | 1976-07-09 | 1979-10-17 | Bostik Ltd | Polyurethanes |
| US4413111A (en) * | 1982-09-29 | 1983-11-01 | Mobay Chemical Corporation | Isocyanate-terminated prepolymers with low free monomer contents |
| US4704445A (en) * | 1985-10-14 | 1987-11-03 | Kuraray Co., Ltd. | Polyurethane compositions |
| GB8728358D0 (en) * | 1987-12-04 | 1988-01-13 | Bostik Ltd | Sheet materials |
| DE3931844A1 (de) * | 1989-09-23 | 1991-04-04 | Bayer Ag | Lagerstabile polyurethanklebstoffe |
| DE4035280A1 (de) * | 1990-11-07 | 1992-05-14 | Bayer Ag | Schmelzklebstoffe |
| US5472785A (en) * | 1994-04-12 | 1995-12-05 | Minnesota Mining And Manufacturing Company | Reactive wax-containing moisture curable hot melt composition |
-
1999
- 1999-06-07 US US09/326,855 patent/US6365700B1/en not_active Expired - Lifetime
-
2000
- 2000-06-07 JP JP2001502489A patent/JP2003501529A/ja active Pending
- 2000-06-07 CA CA002339822A patent/CA2339822C/en not_active Expired - Fee Related
- 2000-06-07 WO PCT/US2000/015604 patent/WO2000075209A1/en not_active Ceased
- 2000-06-07 EP EP00939619A patent/EP1112296B1/en not_active Expired - Lifetime
- 2000-06-07 ES ES00939619T patent/ES2265947T3/es not_active Expired - Lifetime
- 2000-06-07 AT AT00939619T patent/ATE337349T1/de not_active IP Right Cessation
- 2000-06-07 AU AU54680/00A patent/AU5468000A/en not_active Abandoned
- 2000-06-07 DE DE60030242T patent/DE60030242T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003501529A (ja) | 2003-01-14 |
| EP1112296A1 (en) | 2001-07-04 |
| EP1112296B1 (en) | 2006-08-23 |
| CA2339822C (en) | 2008-08-05 |
| ATE337349T1 (de) | 2006-09-15 |
| ES2265947T3 (es) | 2007-03-01 |
| CA2339822A1 (en) | 2000-12-14 |
| WO2000075209A1 (en) | 2000-12-14 |
| DE60030242D1 (de) | 2006-10-05 |
| US6365700B1 (en) | 2002-04-02 |
| AU5468000A (en) | 2000-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: MEISSNER, BOLTE & PARTNER GBR, 80538 MUENCHEN |
|
| R082 | Change of representative |
Ref document number: 1112296 Country of ref document: EP Representative=s name: MEISSNER, BOLTE & PARTNER GBR, DE |