EP3774988A1 - Adhésifs de contrecollage utilisant un polyester obtenu par transestérification d'acide polylactique avec des huiles naturelles - Google Patents

Adhésifs de contrecollage utilisant un polyester obtenu par transestérification d'acide polylactique avec des huiles naturelles

Info

Publication number
EP3774988A1
EP3774988A1 EP19782395.8A EP19782395A EP3774988A1 EP 3774988 A1 EP3774988 A1 EP 3774988A1 EP 19782395 A EP19782395 A EP 19782395A EP 3774988 A1 EP3774988 A1 EP 3774988A1
Authority
EP
European Patent Office
Prior art keywords
component
adhesive
isocyanate
product
polyol
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.)
Pending
Application number
EP19782395.8A
Other languages
German (de)
English (en)
Other versions
EP3774988A4 (fr
Inventor
Alexander P. Mgaya
Zhengmian Chang
Balasubramaniam Ramalingam
Grant B. Kenion
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel IP and Holding GmbH
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
Application filed by Henkel IP and Holding GmbH filed Critical Henkel IP and Holding GmbH
Publication of EP3774988A1 publication Critical patent/EP3774988A1/fr
Publication of EP3774988A4 publication Critical patent/EP3774988A4/fr
Pending legal-status Critical Current

Links

Classifications

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    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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    • B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
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    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
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    • 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
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C—CHEMISTRY; METALLURGY
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    • 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
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W90/00—Enabling technologies or technologies with a potential or indirect contribution to greenhouse gas [GHG] emissions mitigation
    • Y02W90/10—Bio-packaging, e.g. packing containers made from renewable resources or bio-plastics

Definitions

  • a first component comprises an isocyanate-functionalized compound such as NCO-terminated
  • the disclosed flexible packaging adhesive in ready to use form comprises a substantially homogeneous mixture of Component A and Component B.
  • Components A and B are stored separately and mixed in a predetermined ratio just before use. Mixing the components initiates a relatively quick reaction between the isocyanate groups in Component A and the OH groups of the polyols in Component B.
  • a polyurethane prepolymer is a compound such as results, for example, from the reaction of a polyol component (or other active hydrogen-functionalized compound) with at least one polyisocyanate having a functionality of at least two.
  • the term“polyurethane prepolymer” embraces not only compounds having a relatively low molecular weight, such as are formed, for example, from the reaction of a polyol with an excess of polyisocyanate, but also oligomeric or polymeric compounds.
  • polyurethane prepolymers are compounds formed, for example, from the reaction of a trivalent or tetravalent polyol with a molar excess of polyisocyanate, relative to the polyol.
  • polyester polyols are preparable by polycondensation.
  • difunctional and/or trifunctional alcohols can be condensed with a
  • MDI diphenylmethane diisocyanate
  • H12MDI hydrogenated MDI
  • XDI xylylene diisocyanate
  • TXDI tetramethylxylylene diisocyanate
  • Bond strength was tested by preparing a flexible packaging laminate material and allowing that material to cure for a desired time. One inch by 4 inch to 6 inch sample is cut from the pouch and tested for bond strength via a tensile strength tester at room temperature or a desired elevated temperature with failure mode noted. This is a T peel test with the laminated tail held at 90 degrees to the ends being pulled.
  • Loctite Liofol LA 7773 was used as the isocyanate functional component A1.
  • Component A3 and Component B2 were mixed at a ratio of 1.4 parts component A3 to 1-part component B2 (for an NCO/OH equivalents ratio of 1.4/1) to form curable mixed lamination adhesive Ad3.
  • Flexible laminates were prepared using laminate combination 1 at an application temperature of 40 °C, a coating weight of 1.2 Ibs/ream, and a nip temperature of 60 °C. Flexible laminates were cured at 20 °C for 16 days.
  • Component A3 and Component B1 were mixed at a ratio of 1.4 to 1 (for an NCO/OH equivalents ratio of 1.4/1) to form curable mixed lamination adhesive
  • Ad4 Flexible laminates were prepared using 48 ga PET as the primary web, and laminated to 1000 ppm slip 2 mil PE (laminate combination 1). Lamination was done at an application temperature of 40 °C, a coating weight of 1.2 Ibs/ream, and a nip temperature of 60 °C. The flexible laminate was cured at 20 °C for 16 days.
  • Comparative sample AdPC-1-1 comprising cured reaction products of a comparative adhesive based on PA and PC-1 had low bond strength and very poor product resistance. Neither comparative sample AdPC-1-1 nor the comparative adhesive AdPC-1 would be suitable for use as adhesives in laminating materials for food and other products.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Wrappers (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Laminated Bodies (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

L'invention concerne un mélange spécifique de polyols, dont au moins l'un contient le produit de la transestérification de l'acide polylactique polymère avec des huiles naturelles. Le mélange de polyols peut être utilisé en tant que constituant d'un adhésif à deux constituants pour le contrecollage d'un emballage souple. L'autre constituant comprend un composé à fonctionnalité isocyanate. Les deux constituants sont combinés avant usage et l'adhésif obtenu peut être utilisé pour coller des films pour former un matériau d'emballage souple.
EP19782395.8A 2018-04-06 2019-03-28 Adhésifs de contrecollage utilisant un polyester obtenu par transestérification d'acide polylactique avec des huiles naturelles Pending EP3774988A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201862653795P 2018-04-06 2018-04-06
PCT/US2019/024478 WO2019195066A1 (fr) 2018-04-06 2019-03-28 Adhésifs de contrecollage utilisant un polyester obtenu par transestérification d'acide polylactique avec des huiles naturelles

Publications (2)

Publication Number Publication Date
EP3774988A1 true EP3774988A1 (fr) 2021-02-17
EP3774988A4 EP3774988A4 (fr) 2021-12-29

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EP (1) EP3774988A4 (fr)
JP (1) JP7391870B2 (fr)
CN (1) CN111971325B (fr)
WO (1) WO2019195066A1 (fr)

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MX2022015759A (es) * 2020-06-19 2023-01-19 Dow Global Technologies Llc Compuestos de poliol y composiciones adhesivas preparadas con estos.

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Publication number Priority date Publication date Assignee Title
JP4546708B2 (ja) * 2003-09-19 2010-09-15 伊藤製油株式会社 ポリオール組成物及びそれを用いた接着剤組成物
JP2006143829A (ja) * 2004-11-18 2006-06-08 Kanebo Ltd ポリ乳酸系樹脂成形品及びその製造方法
WO2010082639A1 (fr) * 2009-01-16 2010-07-22 バイオベース株式会社 Composition de resine d'acide polylactique et additif pour ladite resine
JP5733217B2 (ja) * 2009-12-14 2015-06-10 日本電気株式会社 ポリ乳酸系ポリオール組成物、その製造方法、ウレタン樹脂組成物、その製造方法及び成形体
PT2630212T (pt) * 2010-10-22 2018-03-26 Henkel IP & Holding GmbH Adesivos robustos para laminação de material para embalagem flexível
US20150159062A1 (en) * 2011-07-22 2015-06-11 Albert M. Giorgini Two part dual-cure adhesive for use in electronics
CN102850743A (zh) * 2012-10-09 2013-01-02 广东益德环保科技有限公司 一种生物降解材料及其制备方法和应用
WO2017003872A1 (fr) * 2015-07-01 2017-01-05 H.B. Fuller Company Composition adhésive à base de polyols de polylactide
CN108602945B (zh) * 2016-02-01 2020-05-15 汉高知识产权控股有限责任公司 聚乳酸与天然油的酯交换
JP2018051796A (ja) * 2016-09-26 2018-04-05 大日本印刷株式会社 積層体およびそれを備える包装製品

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Publication number Publication date
CN111971325B (zh) 2023-08-22
CN111971325A (zh) 2020-11-20
JP7391870B2 (ja) 2023-12-05
EP3774988A4 (fr) 2021-12-29
WO2019195066A1 (fr) 2019-10-10
JP2021521283A (ja) 2021-08-26

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