WO2019195066A1 - 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 Download PDF

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Publication number
WO2019195066A1
WO2019195066A1 PCT/US2019/024478 US2019024478W WO2019195066A1 WO 2019195066 A1 WO2019195066 A1 WO 2019195066A1 US 2019024478 W US2019024478 W US 2019024478W WO 2019195066 A1 WO2019195066 A1 WO 2019195066A1
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WO
WIPO (PCT)
Prior art keywords
component
adhesive
isocyanate
product
polyol
Prior art date
Application number
PCT/US2019/024478
Other languages
English (en)
Inventor
Grant B. Kenion
Alexander P. Mgaya
Zhengmain CHANG
Balasubramaniam Ramalingam
Original Assignee
Henkel IP & 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 & Holding GmbH filed Critical Henkel IP & Holding GmbH
Priority to JP2020554471A priority Critical patent/JP7391870B2/ja
Priority to CN201980023474.9A priority patent/CN111971325B/zh
Priority to EP19782395.8A priority patent/EP3774988A4/fr
Publication of WO2019195066A1 publication Critical patent/WO2019195066A1/fr
Priority to US17/019,617 priority patent/US11891480B2/en

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    • 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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Definitions

  • polyether polyols are those having a molecular weight from about 100 to about 10,000, preferably from about 200 to about 5,000.
  • polycarboxylic acids include succinic acid, adipic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, tetra- chlorophthalic anhydride, endomethylenetetrahydrophthalic anhydride, glutaric anhydride, maleic acid, maleic anhydride, fumaric acid, dimer fatty acid or trimer fatty acid or mixtures of two or more thereof. Where appropriate, minor amounts of monofunctionai fatty acids may be present in the reaction mixture.
  • Polyisocyanates which can be used in component A are not limited and include compounds having two or more reactive isocyanate groups or mixtures of compounds having an average of two or more reactive isocyanate groups.
  • Component A preferably is formulated to have an isocyanate functionality of 2 or greater. Use of a component A having an isocyanate functionality of less than 2 is not likely to provide a laminating adhesive having desired properties.
  • Component B comprises the transesterification product of the polymer polylactic acid with a natural oil. In some embodiments Component B comprises a mixture of polyols including the transesterification product of the polymer polylactic acid with a natural oil and a different polyol. In some embodiments Component B comprises a mixture of polyols including the transesterification product of the polymer polylactic acid with a natural oil, a different polyol and a high OH functionality polyol product.
  • Cured reaction products of the laminating adhesive must have minimum room temperature bond strengths to common laminating film materials of 400 grams/inch or more for a higher stress application. The most preferred result is for the cured reaction products of the laminating adhesive top have sufficient room temperature bond strength to common laminating film materials so that the laminating film fails before the adhesive. Cured reaction products of the laminating adhesive must retain most of this room temperature bond strength to common laminating film materials after exposure to the packaged food product. For some applications the cured reaction products of the laminating adhesive must retain most of this bond strength after exposure to elevated temperatures.
  • Product resistance was tested by preparing a flexible packaging laminate material and allowing that material to cure for a desired time.
  • 4 inch by 4 inch pouches were prepared from the cured laminate and about 30 ml of a test food product (2 gm for the coffee and flavoured coffee samples) was sealed within.
  • the sealed pouch is aged for 100 hours at 60 °C.
  • a 1 inch by 4 inch to 6 inch sample of a bond area is cut from the pouch and tested for bond strength with failure mode noted.
  • Test food products include water, ketchup, mayonnaise, vegetable oil, 1- 1-1 sauce (a 1 to 1 to 1 mixture of ketchup, vinegar and vegetable oil), non-flavoured coffee and hazelnut flavoured coffee. Failure modes and their abbreviations are:
  • 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.

Landscapes

  • 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)
  • Polyesters Or Polycarbonates (AREA)
  • Laminated Bodies (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.
PCT/US2019/024478 2016-02-01 2019-03-28 Adhésifs de contrecollage utilisant un polyester obtenu par transestérification d'acide polylactique avec des huiles naturelles WO2019195066A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2020554471A JP7391870B2 (ja) 2018-04-06 2019-03-28 天然油によるポリ乳酸のエステル交換反応からのポリエステルを使用したラミネート接着剤
CN201980023474.9A CN111971325B (zh) 2018-04-06 2019-03-28 使用来自聚乳酸与天然油的酯交换的聚酯的层合粘合剂
EP19782395.8A EP3774988A4 (fr) 2018-04-06 2019-03-28 Adhésifs de contrecollage utilisant un polyester obtenu par transestérification d'acide polylactique avec des huiles naturelles
US17/019,617 US11891480B2 (en) 2016-02-01 2020-09-14 Laminating adhesives using polyester from transesterification of polylactic acid with natural oils

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201862653795P 2018-04-06 2018-04-06
US62/653,795 2018-04-06

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US16/374,350 Continuation-In-Part US10941246B2 (en) 2016-02-01 2019-04-03 Transesterification of polylactic acid with natural oils

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US16/374,350 Continuation US10941246B2 (en) 2016-02-01 2019-04-03 Transesterification of polylactic acid with natural oils
US17/019,617 Continuation US11891480B2 (en) 2016-02-01 2020-09-14 Laminating adhesives using polyester from transesterification of polylactic acid with natural oils

Publications (1)

Publication Number Publication Date
WO2019195066A1 true WO2019195066A1 (fr) 2019-10-10

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PCT/US2019/024478 WO2019195066A1 (fr) 2016-02-01 2019-03-28 Adhésifs de contrecollage utilisant un polyester obtenu par transestérification d'acide polylactique avec des huiles naturelles

Country Status (4)

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

Cited By (1)

* Cited by examiner, † Cited by third party
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EP4168462A4 (fr) * 2020-06-19 2024-03-13 Dow Global Technologies Llc Composés de polyol et compositions adhésives préparées à l'aide de ceux-ci

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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
CN102282194B (zh) * 2009-01-16 2015-02-25 生物基础塑料开发有限公司 聚乳酸树脂组合物和聚乳酸树脂用添加剂
WO2017136373A1 (fr) * 2016-02-01 2017-08-10 Henkel IP & Holding GmbH Transestérification de poly(acide lactique) à l'aide des huiles naturelles

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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
US8772433B2 (en) * 2009-12-14 2014-07-08 Nec Corporation Polyactic acid-based polyol composition, process for production thereof, urethane resin composition, process for production of same, and molded products thereof
TR201808241T4 (tr) * 2010-10-22 2018-07-23 Henkel IP & Holding GmbH Esnek ambalaj malzemesi̇ i̇çi̇n sağlam lami̇ne edi̇ci̇ yapiştiricilari
WO2013016136A2 (fr) * 2011-07-22 2013-01-31 H.B. Fuller Company Adhésif à deux parties à polymérisation double à utiliser en électronique
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
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 Priority date Publication date Assignee Title
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
CN102282194B (zh) * 2009-01-16 2015-02-25 生物基础塑料开发有限公司 聚乳酸树脂组合物和聚乳酸树脂用添加剂
WO2017136373A1 (fr) * 2016-02-01 2017-08-10 Henkel IP & Holding GmbH Transestérification de poly(acide lactique) à l'aide des huiles naturelles

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4168462A4 (fr) * 2020-06-19 2024-03-13 Dow Global Technologies Llc Composés de polyol et compositions adhésives préparées à l'aide de ceux-ci

Also Published As

Publication number Publication date
EP3774988A1 (fr) 2021-02-17
JP7391870B2 (ja) 2023-12-05
CN111971325B (zh) 2023-08-22
JP2021521283A (ja) 2021-08-26
CN111971325A (zh) 2020-11-20
EP3774988A4 (fr) 2021-12-29

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