DE60033059T2 - Haftklebstoff auf basis von polyurethan, systeme für solche klebstoffe, daraus hergestellte gegenstände und verfahren zur herstellung solcher klebstoffe - Google Patents
Haftklebstoff auf basis von polyurethan, systeme für solche klebstoffe, daraus hergestellte gegenstände und verfahren zur herstellung solcher klebstoffe Download PDFInfo
- Publication number
- DE60033059T2 DE60033059T2 DE60033059T DE60033059T DE60033059T2 DE 60033059 T2 DE60033059 T2 DE 60033059T2 DE 60033059 T DE60033059 T DE 60033059T DE 60033059 T DE60033059 T DE 60033059T DE 60033059 T2 DE60033059 T2 DE 60033059T2
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- Germany
- Prior art keywords
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- polyol
- polyurethane
- diol
- 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.)
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- 238000000034 method Methods 0.000 title description 52
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- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 115
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- 150000002009 diols Chemical class 0.000 claims description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 65
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- 238000002360 preparation method Methods 0.000 description 74
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- 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 18
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- 125000003277 amino group Chemical group 0.000 description 2
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011146 organic particle Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000012956 testing procedure 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
- 239000002470 thermal conductor Substances 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
-
- 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
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
-
- 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
- C08G18/4808—Mixtures of two or more polyetherdiols
-
- 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
- C08G2170/40—Compositions for pressure-sensitive adhesives
-
- 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
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2896—Adhesive compositions including nitrogen containing condensation polymer [e.g., polyurethane, polyisocyanate, etc.]
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31565—Next to polyester [polyethylene terephthalate, etc.]
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31573—Next to addition polymer of ethylenically unsaturated monomer
- Y10T428/31587—Hydrocarbon polymer [polyethylene, polybutadiene, etc.]
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31598—Next to silicon-containing [silicone, cement, etc.] layer
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)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/514,123 US6518359B1 (en) | 2000-02-25 | 2000-02-25 | Polyurethane-based pressure-sensitive adhesives, systems for such adhesives, articles therefrom, and methods of making |
| US514123 | 2000-02-25 | ||
| PCT/US2000/015448 WO2001062817A1 (en) | 2000-02-25 | 2000-06-05 | Polyurethane-based pressure-sensitive adhesives, systems for such adhesives, articles therefrom, and methods of making |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60033059D1 DE60033059D1 (de) | 2007-03-08 |
| DE60033059T2 true DE60033059T2 (de) | 2007-11-08 |
Family
ID=24045891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60033059T Revoked DE60033059T2 (de) | 2000-02-25 | 2000-06-05 | Haftklebstoff auf basis von polyurethan, systeme für solche klebstoffe, daraus hergestellte gegenstände und verfahren zur herstellung solcher klebstoffe |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6518359B1 (https=) |
| EP (1) | EP1257590B1 (https=) |
| JP (1) | JP2003524041A (https=) |
| AU (1) | AU2000255961A1 (https=) |
| DE (1) | DE60033059T2 (https=) |
| WO (1) | WO2001062817A1 (https=) |
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| US6642304B1 (en) * | 2000-02-25 | 2003-11-04 | 3M Innovative Properties Company | Polyurethane-based adhesives, systems for such adhesives, articles therefrom, and methods of making |
| EP1361236B1 (en) * | 2002-04-25 | 2004-12-29 | Sicpa Holding S.A. | A polyurethane resin derived from hard ketonic resins |
| DE10317791A1 (de) * | 2003-04-16 | 2004-12-02 | Tesa Ag | Haftklebstoff aus Polyurethan für empfindliche Oberflächen |
| RU2230765C1 (ru) * | 2003-05-07 | 2004-06-20 | Федеральное государственное унитарное предприятие "Всероссийский научно-исследовательский институт авиационных материалов" | Клеевая композиция |
| US20050137375A1 (en) * | 2003-12-19 | 2005-06-23 | 3M Innovative Properties Company | Polyurethane-based pressure sensitive adhesives and methods of manufacture |
| WO2005105857A1 (en) * | 2004-04-27 | 2005-11-10 | Ashland Inc. | Polyester-polyether hybrid urethane acrylate oligomer for uv curing pressure sensitive adhesives |
| US7816472B2 (en) * | 2004-08-19 | 2010-10-19 | 3M Innovative Properties Company | Polydiacetylene polymer compositions and methods of manufacture |
| US7371511B2 (en) * | 2004-08-19 | 2008-05-13 | 3M Innovative Properties Company | Polydiacetylene polymer blends |
| JP5008046B2 (ja) * | 2005-06-14 | 2012-08-22 | ローム株式会社 | 半導体デバイス |
| WO2007048145A2 (en) * | 2005-10-21 | 2007-04-26 | Entrotech, Inc. | Protective sheets, articles, and methods |
| US8545960B2 (en) * | 2006-10-23 | 2013-10-01 | Entrotech, Inc. | Articles comprising protective sheets and related methods |
| US20090030146A1 (en) * | 2007-07-24 | 2009-01-29 | Yuliya Berezkin | Polyurethane dispersions for sealants |
| EP2193024A4 (en) | 2007-09-25 | 2013-11-06 | Entrotech Inc | PAINT SHEET FILMS, COMPOUNDS THEREOF AND RELATED METHODS |
| KR101503561B1 (ko) * | 2007-12-27 | 2015-03-17 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 우레아계 감압성 접착제 |
| US10981371B2 (en) * | 2008-01-19 | 2021-04-20 | Entrotech, Inc. | Protected graphics and related methods |
| US20090078590A1 (en) | 2008-01-21 | 2009-03-26 | Smith Dennis R | Ultrasecure card package |
| WO2010132176A2 (en) | 2009-05-15 | 2010-11-18 | 3M Innovative Properties Company | Urethane-based pressure sensitive adhesives |
| JP5767235B2 (ja) | 2009-11-09 | 2015-08-19 | スリーエム イノベイティブ プロパティズ カンパニー | 医療用物品及び不混和性材料を用いる製造方法 |
| WO2011057175A1 (en) | 2009-11-09 | 2011-05-12 | 3M Innovative Properties Company | Medical articles and methods of making using miscible composition |
| CN102058895A (zh) * | 2009-11-17 | 2011-05-18 | 上海普天欣生物技术有限公司 | 一种消毒活性贴膜及其制备方法和用途 |
| US9089624B2 (en) * | 2010-08-23 | 2015-07-28 | Basf Se | Ultrathin fluid-absorbent cores comprising adhesive and having very low dry SAP loss |
| WO2012158483A2 (en) | 2011-05-16 | 2012-11-22 | Avery Dennison Corporation | Adhesive containing microparticles |
| US9818499B2 (en) * | 2011-10-13 | 2017-11-14 | Flexcon Company, Inc. | Electrically conductive materials formed by electrophoresis |
| US9427945B2 (en) * | 2011-12-30 | 2016-08-30 | Liberman Distributing And Manufacturing Co. | Extendable self-supporting material composites and manufacture thereof |
| WO2013148506A1 (en) | 2012-03-30 | 2013-10-03 | 3M Innovative Properties Company | Urea-based and urethane-based pressure sensitive adhesive blends |
| JP5961474B2 (ja) * | 2012-07-31 | 2016-08-02 | 日東電工株式会社 | 表面保護フィルム |
| CN105567115B (zh) | 2013-02-07 | 2018-09-07 | 艾利丹尼森公司 | 具有改进性质的抗微生物粘合剂 |
| EP2968014B1 (en) | 2013-03-15 | 2019-04-24 | Avery Dennison Corporation | Transparent cover dressing application system and inclusion of label strip |
| EP3013294B1 (en) | 2013-06-28 | 2019-09-25 | 3M Innovative Properties Company | Fibrin-coated wound dressing |
| ES2978949T3 (es) * | 2014-05-13 | 2024-09-23 | Basf Se | Preparación con bajo contenido de fenol a base de poliuretano termoplástico |
| ES2755097T3 (es) * | 2014-05-16 | 2020-04-21 | Henkel Ag & Co Kgaa | Adhesivo de fusión en caliente de poliuretano termoplástico |
| EP2944662B1 (en) * | 2014-05-16 | 2018-07-18 | Henkel AG & Co. KGaA | Thermoplastic polyurethane hot melt adhesive |
| EP3151813B1 (en) | 2014-06-05 | 2020-12-09 | Avery Dennison Corporation | Articles with active agent concentrated at the substrate contacting surface and related methods |
| US10611873B2 (en) | 2014-12-16 | 2020-04-07 | 3M Innovative Properties Company | Polyurethane pressure-sensitive adhesives |
| EP3792325A1 (en) * | 2015-09-21 | 2021-03-17 | 3M Innovative Properties Company | Chemical resistant polyurethane adhesive |
| WO2018057379A1 (en) | 2016-09-20 | 2018-03-29 | Aero Advanced Paint Technology, Inc. | Paint film appliques with reduced defects, articles, and methods |
| US11453777B2 (en) | 2016-12-16 | 2022-09-27 | Oregon State University | Pressure sensitive adhesives from plant oil-based polyols |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3246049A (en) | 1963-08-30 | 1966-04-12 | Norton Co | Pressure sensitive adhesive comprising an isocyanate cross-linked polyester of castor oil and diglycolic acid, and tape coated with said adhesive |
| US3360599A (en) | 1963-11-06 | 1967-12-26 | Shell Oil Co | Preparation of coherent block copolymer films of high tensile strength and extensibility |
| GB1113925A (en) | 1964-09-18 | 1968-05-15 | Dunlop Co Ltd | Polyurethane pressure-sensitive adhesives |
| US3437622A (en) | 1965-12-06 | 1969-04-08 | Anchor Continental Inc | Polyurethane-based pressure-sensitive adhesives |
| US3503917A (en) | 1967-03-09 | 1970-03-31 | Burke Oliver W Jun | Aqueous latices of high polymer compositions and processes for producing same |
| GB1216672A (en) | 1967-05-16 | 1970-12-23 | Dunlop Co Ltd | Polyurethane pressure-sensitive adhesives |
| US3925283A (en) | 1970-06-29 | 1975-12-09 | Continental Tapes Inc | Polyurethane pressure-sensitive adhesive products and processes |
| US3796678A (en) | 1970-08-17 | 1974-03-12 | Minnesota Mining & Mfg | Highly branched,capped polyurethanes for pressure sensitive adhesives |
| US3767040A (en) | 1971-03-01 | 1973-10-23 | Minnesota Mining & Mfg | Pressure-sensitive polyurethane adhesives |
| US3718712A (en) | 1971-03-01 | 1973-02-27 | Minnesota Mining & Mfg | Pressure-sensitive adhesives based on cyclic terpene urethane resin |
| US3743617A (en) | 1971-05-17 | 1973-07-03 | D Kest | Urethane base pressure sensitive adhesive |
| DE2436873A1 (de) | 1974-07-31 | 1976-02-19 | Basf Ag | Verfahren zur herstellung von haftklebern |
| US4123403A (en) | 1977-06-27 | 1978-10-31 | The Dow Chemical Company | Continuous process for preparing aqueous polymer microsuspensions |
| JPS5552369A (en) | 1978-10-13 | 1980-04-16 | Toyo Tire & Rubber Co Ltd | Water-dispersed pressure-sensitive adhesive composition |
| JPS62270613A (ja) * | 1986-05-19 | 1987-11-25 | Dainippon Ink & Chem Inc | 接着力のすぐれたポリウレタン水性分散液の製造方法 |
| US5102714A (en) | 1988-12-20 | 1992-04-07 | The Dow Chemical Company | Removable polyurethane adhesive |
| US5037864A (en) | 1989-07-11 | 1991-08-06 | The Dow Chemical Company | Semi-continuous process for the preparation of polyurethane-urea aqueous dispersions |
| US4985491A (en) | 1989-10-05 | 1991-01-15 | Olin Corporation | Polyurethane sealants made using high molecular weight polyols prepared with double metal cyanide catalysts |
| US5532058A (en) | 1990-12-10 | 1996-07-02 | H. B. Fuller Licensing & Financing, Inc. | Dry-bonded film laminate employing polyurethane dispersion adhesives with improved crosslinkers |
| EP0552420A3 (en) | 1992-01-24 | 1993-09-15 | H.B. Fuller Licensing & Financing, Inc. | Water dispersed polyurethane polymer for improved coatings and adhesives |
| CA2095876A1 (en) | 1992-06-05 | 1993-12-06 | Nigel Barksby | Isocyante-terminated prepolymers derived from polyether polyol mixtures having low monol content and their use in polyurethanes |
| NZ248977A (en) | 1992-11-09 | 1995-06-27 | Squibb & Sons Inc | Pressure-sensitive adhesive comprising a polyurethane having excess hydroxyl functionality; medical articles comprising a layer of such adhesive |
| US5354808A (en) | 1992-12-08 | 1994-10-11 | Minnesota Mining And Manufacturing Company | Polyurethanes including pendant hindered amines and compositions incorporating same |
| DE4242687B8 (de) | 1992-12-17 | 2006-01-12 | Henkel Kgaa | Hydrophile Polyurethane |
| US5442028A (en) | 1993-08-20 | 1995-08-15 | Morton International, Inc. | Curatives for aqueous adhesives |
| US5554686A (en) | 1993-08-20 | 1996-09-10 | Minnesota Mining And Manufacturing Company | Room temperature curable silane-terminated polyurethane dispersions |
| US5608000A (en) | 1993-09-24 | 1997-03-04 | H. B. Fuller Licensing & Financing, Inc. | Aqueous polyurethane dispersion adhesive compositions with improved heat resistance |
| US5703158A (en) | 1993-09-24 | 1997-12-30 | H.B. Fuller Licensing & Financing, Inc. | Aqueous anionic poly (urethane/urea) dispersions |
| JPH07102233A (ja) | 1993-10-01 | 1995-04-18 | Sekisui Chem Co Ltd | 水性接着剤組成物 |
| US5714543A (en) | 1994-01-13 | 1998-02-03 | Bristol-Myers Squibb Company | Water soluble polymer additives for polyurethane-based pressure sensitive adhesives |
| US5486570A (en) | 1994-09-29 | 1996-01-23 | Shell Oil Company | Polyurethane sealants and adhesives containing saturated hydrocarbon polyols |
| AU722654B2 (en) | 1995-12-19 | 2000-08-10 | Bristol-Myers Squibb Company | Polyurethane pressure-sensitive adhesives |
| US5952422A (en) | 1995-12-20 | 1999-09-14 | Bristol-Myers Squibb Company | Polyurethane pressure-sensitive adhesives |
| KR0173522B1 (ko) | 1995-12-20 | 1999-04-01 | 최근배 | 폴리우레탄 프리폴리머의 제조방법, 상기 프리폴리머로부터 제조되는 수용성 폴리우레탄 분산체의 제조방법 및 그의 용도 |
| US5576382A (en) * | 1996-05-05 | 1996-11-19 | Arco Chemical Technology, L.P. | Aqueous polyurethane dispersions based on polyether polyols of low monol content |
| US5807919A (en) | 1996-08-13 | 1998-09-15 | H.B. Fuller Licensing & Financing, Inc. | Water-based sulfonated polymer compositions |
| US5880250A (en) | 1996-08-16 | 1999-03-09 | Inolex Investment Corporation | Polymeric acid functional polyols, polyurethanes and methods for making same |
| US5985317A (en) | 1996-09-06 | 1999-11-16 | Theratech, Inc. | Pressure sensitive adhesive matrix patches for transdermal delivery of salts of pharmaceutical agents |
| US6130309A (en) * | 1996-09-20 | 2000-10-10 | Tyndale Plains-Hunter, Ltd. | Hydrophilic polyether polyurethanes containing carboxylic acid |
| ES2190583T3 (es) | 1997-01-16 | 2003-08-01 | Dow Global Technologies Inc | Adhesivo de latex de poliuretano sensible a la presion y procedimiento para fabricarlo. |
| DE19725297A1 (de) | 1997-06-14 | 1998-12-17 | Basf Ag | Wässrige Polyurethandispersionen aus Polypropylenglykol mit geringem Harnstoffgehalt |
| BR9812514A (pt) | 1997-09-24 | 2000-07-25 | Henkel Kgaa | Adesivo de poliuretana |
| US6162863A (en) * | 1997-12-04 | 2000-12-19 | Henkel Kommanditgesellschaft Auf Aktien | Waterborne polyurethanes with urea-urethane linkages |
| US6359100B1 (en) * | 1998-01-28 | 2002-03-19 | Bristol-Myers Squibb Company | Methods of preparing polyurethane adhesives, adhesives produced thereby and medical devices employing the same |
-
2000
- 2000-02-25 US US09/514,123 patent/US6518359B1/en not_active Expired - Lifetime
- 2000-06-05 DE DE60033059T patent/DE60033059T2/de not_active Revoked
- 2000-06-05 JP JP2001562596A patent/JP2003524041A/ja active Pending
- 2000-06-05 EP EP00941224A patent/EP1257590B1/en not_active Revoked
- 2000-06-05 WO PCT/US2000/015448 patent/WO2001062817A1/en not_active Ceased
- 2000-06-05 AU AU2000255961A patent/AU2000255961A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US6518359B1 (en) | 2003-02-11 |
| DE60033059D1 (de) | 2007-03-08 |
| EP1257590B1 (en) | 2007-01-17 |
| EP1257590A1 (en) | 2002-11-20 |
| AU2000255961A1 (en) | 2001-09-03 |
| WO2001062817A1 (en) | 2001-08-30 |
| JP2003524041A (ja) | 2003-08-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8363 | Opposition against the patent | ||
| 8331 | Complete revocation |