DE69327702D1 - Klebstoff enthaltend ein Polyurethanharz und Verfahren zur Herstellung eines Laminats - Google Patents

Klebstoff enthaltend ein Polyurethanharz und Verfahren zur Herstellung eines Laminats

Info

Publication number
DE69327702D1
DE69327702D1 DE69327702T DE69327702T DE69327702D1 DE 69327702 D1 DE69327702 D1 DE 69327702D1 DE 69327702 T DE69327702 T DE 69327702T DE 69327702 T DE69327702 T DE 69327702T DE 69327702 D1 DE69327702 D1 DE 69327702D1
Authority
DE
Germany
Prior art keywords
laminate
producing
polyurethane resin
adhesive containing
adhesive
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
Application number
DE69327702T
Other languages
English (en)
Other versions
DE69327702T2 (de
Inventor
Takahito Miyamoto
Kyoichi Kotani
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sakata Inx Corp
Original Assignee
Sakata Inx Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26547468&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DE69327702(D1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Sakata Inx Corp filed Critical Sakata Inx Corp
Application granted granted Critical
Publication of DE69327702D1 publication Critical patent/DE69327702D1/de
Publication of DE69327702T2 publication Critical patent/DE69327702T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • 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
    • C08G18/0809—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups
    • C08G18/0814—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups containing ammonium 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
    • C08G18/0804—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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
    • C08G18/3834—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing hydrazide or semi-carbazide groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
    • 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
    • C08G2170/00—Compositions for adhesives
    • C08G2170/80—Compositions for aqueous adhesives

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Lining Or Joining Of Plastics Or The Like (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)
DE1993627702 1992-11-06 1993-11-04 Klebstoff enthaltend ein Polyurethanharz und Verfahren zur Herstellung eines Laminats Expired - Fee Related DE69327702T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP29732892 1992-11-06
JP26648693A JP3001358B2 (ja) 1992-11-06 1993-10-25 プラスチックフィルム用水性印刷インキ組成物、水性ラミネート用接着剤、およびそれを用いたラミネート加工物の製造方法

Publications (2)

Publication Number Publication Date
DE69327702D1 true DE69327702D1 (de) 2000-03-02
DE69327702T2 DE69327702T2 (de) 2000-09-28

Family

ID=26547468

Family Applications (2)

Application Number Title Priority Date Filing Date
DE1993627702 Expired - Fee Related DE69327702T2 (de) 1992-11-06 1993-11-04 Klebstoff enthaltend ein Polyurethanharz und Verfahren zur Herstellung eines Laminats
DE1993633804 Revoked DE69333804T2 (de) 1992-11-06 1993-11-04 Polyurethanharz, dessen Herstellungsverfahren und seine Verwendung

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE1993633804 Revoked DE69333804T2 (de) 1992-11-06 1993-11-04 Polyurethanharz, dessen Herstellungsverfahren und seine Verwendung

Country Status (5)

Country Link
US (1) US5656701A (de)
EP (2) EP0596503B1 (de)
JP (1) JP3001358B2 (de)
DE (2) DE69327702T2 (de)
ES (2) ES2142847T3 (de)

Families Citing this family (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2657203B2 (ja) * 1993-10-01 1997-09-24 中小企業事業団 水性印刷インキ組成物
JP3052740B2 (ja) * 1994-08-12 2000-06-19 東洋インキ製造株式会社 包装用表刷り水性印刷インキ組成物および包装用材料
JP3391910B2 (ja) * 1994-10-19 2003-03-31 サカタインクス株式会社 ラミネート用水性印刷インキ組成物およびそれを用いるラミネート方法
US5700851A (en) * 1995-10-17 1997-12-23 Tektronix, Inc. Ink-jet ink composition containing a colored polyurethane dispersion
JP3456841B2 (ja) * 1996-07-08 2003-10-14 サカタインクス株式会社 ドライラミネート接着剤残液のゲル化防止方法
JP3181854B2 (ja) * 1997-03-31 2001-07-03 三洋化成工業株式会社 水性接着剤組成物
JPH1110799A (ja) * 1997-06-20 1999-01-19 Dainippon Printing Co Ltd 積層材およびそれを使用した包装用袋
CN1134516C (zh) 1997-10-15 2004-01-14 美国3M公司 包含印刷图象的弹性绷带
CA2260402C (en) * 1998-01-22 2001-10-23 Pierre Boisvert Display card
DE19812751C2 (de) 1998-03-24 2001-11-22 Skw Bauchemie Gmbh Lösemittelfreie Polyurethan-Dispersion
US6500289B2 (en) 1998-11-12 2002-12-31 Kimberly-Clark Worldwide, Inc. Method of using water-borne epoxies and urethanes in print bonding fluid and products made therefrom
US6127514A (en) * 1998-11-23 2000-10-03 Bayer Corporation One-component thermoset coating compositions
US6455132B1 (en) 1999-02-04 2002-09-24 Kodak Polychrome Graphics Llc Lithographic printing printable media and process for the production thereof
US6528127B1 (en) * 1999-03-08 2003-03-04 Cryovac, Inc. Method of providing a printed thermoplastic film having a radiation-cured overprint coating
USH2113H1 (en) * 1999-08-16 2005-01-04 Xerox Corporation Ink compositions
US6455631B1 (en) * 2000-12-01 2002-09-24 Bayer Corporation Aqueous polyurethane dispersions containing modified hydrazide groups and their use in one-component thermoset compositions
KR100395154B1 (ko) * 2000-12-18 2003-08-21 주식회사지엠피 라이트 프로텍터 시트
JP4763138B2 (ja) * 2001-02-08 2011-08-31 中央理化工業株式会社 ラミネート用接着剤
US20040242725A1 (en) * 2001-10-18 2004-12-02 Gordon Kotora Ionically cross-linked paste inks
US6624240B2 (en) 2001-12-28 2003-09-23 Sun Chemical Corporation Low molecular weight polyurethane resins
JP4494708B2 (ja) * 2002-08-23 2010-06-30 大日精化工業株式会社 コーティング剤用ベヒクル組成物及びポリスチレン製シュリンクフィルムに印刷する方法並びにポリスチレン製シュリンクフィルム印刷物
US7829631B2 (en) 2002-09-18 2010-11-09 Valspar Sourcing, Inc. Self-crosslinkable waterborne coating composition
DE10339479A1 (de) 2003-08-27 2005-05-12 Basf Ag Schaumregulierungsmittel auf Basis von kationischen Urethan-Oligomeren
DE10353953A1 (de) * 2003-11-18 2005-06-09 Basf Ag Kaschierklebstoffe, enthaltend Polyurethan und Epoxidharz
EP1813631B1 (de) * 2004-09-30 2011-03-23 Asahi Glass Company, Limited Verfahren zur herstellung von urethanharz und haftklebstoff
ES2557442T3 (es) * 2005-01-25 2016-01-26 Dai Nippon Printing Co., Ltd. Lámina de conformación y método para la preparación de una placa de decoración
US8187695B2 (en) * 2005-09-30 2012-05-29 Dai Nippon Printing Co., Ltd. Shaping sheet, resin decorative material and method of producing the same
JP5224640B2 (ja) * 2005-10-07 2013-07-03 昭和電工株式会社 カルボキシル基含有ポリウレタンおよび熱硬化性ポリウレタン樹脂組成物
EP1983012A4 (de) * 2006-02-10 2012-03-14 Asahi Glass Co Ltd Herstellungsverfahren für urethanharz und haftmittel
MX277854B (es) * 2006-09-21 2010-08-04 Clariant Finance Bvi Ltd Dispersiones de poliuretano/poliurea acuosas.
CN101583675B (zh) * 2006-11-10 2016-03-02 太阳化学公司 用于非织造基材的水基印刷油墨
US20110176753A1 (en) * 2007-02-01 2011-07-21 Michael Nowak Package having a printed laminate
JP2008231188A (ja) * 2007-03-19 2008-10-02 Dic Corp 一液型水性コーティング剤、その製造方法および塗装物
EP2300508A1 (de) * 2008-07-14 2011-03-30 DSM IP Assets B.V. Formaldehydfreie haftstoffe auf wasserbasis
CN101805439B (zh) * 2009-10-28 2012-02-22 张伟公 聚氨酯纯水油墨链接料及其纯水油墨
EP2545010B1 (de) * 2010-03-08 2015-01-21 Dow Global Technologies LLC Primer-zusammensetzung auf wasserbasis für isocyanat- und silan-funktionelle haftstoffe
JP5408000B2 (ja) * 2010-03-31 2014-02-05 宇部興産株式会社 水性ポリウレタン樹脂分散体及びその使用
CN102741366B (zh) * 2010-05-28 2014-11-05 Dic株式会社 喷墨印刷墨液用粘合剂的制造方法、喷墨印刷用墨液以及印刷物
US20130085217A1 (en) * 2010-06-17 2013-04-04 Hewlett-Packard Development Company, Lp Polyurethane-containing inkjet ink
JP5730113B2 (ja) * 2010-07-05 2015-06-03 キヤノン株式会社 インクジェット用インク、インクジェット記録方法、及びインクカートリッジ
TWI421320B (zh) * 2011-01-21 2014-01-01 Toyo Ink Sc Holdings Co Ltd 接著劑組成物及積層體
CN104169387B (zh) * 2012-03-15 2015-11-25 Dic株式会社 热密封剂、使用了其的层叠体及太阳能电池模块
JP6201348B2 (ja) * 2012-03-15 2017-09-27 Dic株式会社 水性インクジェット記録用インク及び積層体の製造方法
US8573762B1 (en) * 2012-11-16 2013-11-05 Hewlett-Packard Development Company, L.P. Inkjet inks having sustained decap
WO2015107078A1 (en) * 2014-01-17 2015-07-23 Basf Se Lamination printing ink comprising an aqueous dispersion comprising polyurethane
US9523021B2 (en) 2014-04-25 2016-12-20 Ppg Industries Ohio, Inc. Waterborne coating compositions for soft touch coatings
WO2017062760A1 (en) * 2015-10-08 2017-04-13 Basf Se Preparation of retort packaging ink through cross-linking of polyurethane resins
US10865326B2 (en) 2017-09-20 2020-12-15 Ppg Industries Ohio, Inc. Coating compositions, elastic barrier coatings formed therefrom, and methods of applying such coatings
CN109575219B (zh) * 2017-09-28 2021-09-03 中国石油化工股份有限公司 一种水性环氧改性水性聚氨酯油墨连结料及其制备方法
CN108841239A (zh) * 2018-06-12 2018-11-20 苏州中亚油墨有限公司 软包装用复合水性聚氨酯油墨
WO2020026935A1 (ja) * 2018-08-01 2020-02-06 Dic株式会社 粘着剤組成物及び表面保護フィルム
JP7238715B2 (ja) * 2018-09-19 2023-03-14 東洋インキＳｃホールディングス株式会社 水性グラビアまたはフレキソインキ、印刷物および積層体
CN109880575B (zh) * 2018-12-29 2021-12-07 新纶新能源材料(常州)有限公司 一种水性聚氨酯胶黏剂及其制备方法
US10836924B2 (en) 2019-03-15 2020-11-17 Ppg Industries Ohio, Inc. Coating compositions and elastic barrier coatings formed therefrom
US10829664B2 (en) 2019-03-15 2020-11-10 Ppg Industries Ohio, Inc. Coating compositions containing polythioethers and elastic barrier coatings formed therefrom
CN114920916B (zh) * 2022-03-27 2023-11-28 上海师范大学 一种聚丁二酸丁二醇酯的连续合成方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3687952A (en) * 1968-05-31 1972-08-29 Dynamit Nobel Ag HALOGENPHENOXY-s-TRIAZINE DERIVATIVES HAVING IMPROVED SOLUBILITY
DE1770591A1 (de) * 1968-06-07 1971-11-04 Bayer Ag Lineare,segmentierte Polyurethanelastomere
DE2707659A1 (de) * 1977-02-23 1978-08-24 Bayer Ag Selbstvernetzbare polyurethane
US4412022A (en) * 1981-05-19 1983-10-25 Kuraray Co., Ltd. Polyurethane coating compositions prepared from a polymeric diol, an alicyclic diisocyanate, an alicyclic diamine and either hydrazine or isophthalic acid dihydrazide
DE3227017A1 (de) * 1982-07-20 1984-01-26 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung von kunststoffen aus polyisocyanat-basis
DE3344693A1 (de) * 1983-12-10 1985-06-20 Bayer Ag, 5090 Leverkusen Waessrige loesungen oder dispersionen von polyisocyanat-polyadditionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als bzw. zur herstellung von klebemittel
DE3431144A1 (de) * 1984-08-24 1986-03-06 Hüls AG, 4370 Marl Kaltvernetzende pur-dispersionen, ihre herstellung und verwendung
DE3630045A1 (de) * 1986-09-04 1988-03-17 Bayer Ag Klebstoff und die verwendung des klebstoffs zur herstellung von verklebungen
DE3837519A1 (de) * 1988-11-04 1990-05-10 Basf Lacke & Farben Lagerstabile vernetzbare waessrige polyurethandispersionen
US5137967A (en) * 1990-07-06 1992-08-11 Reichhold Chemicals, Inc. Hydrazine extended aqueous polyurethane

Also Published As

Publication number Publication date
DE69333804D1 (de) 2005-06-09
US5656701A (en) 1997-08-12
DE69327702T2 (de) 2000-09-28
ES2142847T3 (es) 2000-05-01
EP0596503A1 (de) 1994-05-11
JPH06206972A (ja) 1994-07-26
EP0931802A1 (de) 1999-07-28
JP3001358B2 (ja) 2000-01-24
EP0596503B1 (de) 2000-01-26
ES2242324T3 (es) 2005-11-01
DE69333804T2 (de) 2006-03-02
EP0931802B1 (de) 2005-05-04

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