EP0894122A1 - Adhesif compostable - Google Patents

Adhesif compostable

Info

Publication number
EP0894122A1
EP0894122A1 EP97920622A EP97920622A EP0894122A1 EP 0894122 A1 EP0894122 A1 EP 0894122A1 EP 97920622 A EP97920622 A EP 97920622A EP 97920622 A EP97920622 A EP 97920622A EP 0894122 A1 EP0894122 A1 EP 0894122A1
Authority
EP
European Patent Office
Prior art keywords
acids
bifunctional
aliphatic
alcohols
optionally
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.)
Withdrawn
Application number
EP97920622A
Other languages
German (de)
English (en)
Inventor
Ernst Grigat
Karsten-Josef Idel
Uwe Westeppe
Wolfgang Schulz-Schlitte
Winfried Pommeranz
Jürgen Lörcks
Harald Schmidt
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.)
Bayer AG
BioTec Biologische Naturverpackungen GmbH and Co KG
Original Assignee
Bayer AG
BioTec Biologische Naturverpackungen GmbH and Co KG
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 Bayer AG, BioTec Biologische Naturverpackungen GmbH and Co KG filed Critical Bayer AG
Publication of EP0894122A1 publication Critical patent/EP0894122A1/fr
Withdrawn legal-status Critical Current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
    • C08G18/28—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
    • 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
    • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
    • 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
    • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
    • C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • 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
    • C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
    • C09J167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
    • 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
    • C09J169/00—Adhesives based on polycarbonates; Adhesives based on derivatives of polycarbonates
    • C09J169/005—Polyester-carbonates
    • 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
    • C09J175/06—Polyurethanes from polyesters
    • 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
    • C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
    • C09J177/12—Polyester-amides
    • 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
    • C08G2230/00—Compositions for preparing biodegradable polymers

Definitions

  • the present invention relates to a compostable adhesive, a method for producing the same and the use of the adhesive for gluing materials.
  • Adhesives as such have long been known (see Römpp Chemielexikon, 9th edition, Thieme Verlag 1990, keyword “adhesives”).
  • the use of synthetic polymers in particular has significantly expanded the development of adhesives.
  • the disadvantage of the adhesive polymers used hitherto is, especially after
  • the task was solved by dissolving completely biodegradable polymers in suitable solvents and using this solution for gluing parts.
  • the bond binds through the evaporation of the solvent and the precipitation or crystallization of the polymers into those to be bonded
  • Suitable biodegradable polymers are aliphatic or partially aromatic polyesters, thermoplastic aliphatic or partially aromatic polyester urethanes, aliphatic or aliphatic-aromatic polyester carbonates, aliphatic polyester amides.
  • A) aliphatic bifunctional alcohols preferably linear C 2 -C 10 dialcohols such as ethanediol, butanediol, hexanediol, particularly preferably butanediol and / or optionally cycloaliphatic see bifunctional alcohols, preferably with C 5 -C 6 C atoms
  • cycloaliphati see ring such as cyclohexanedimethanol and / or partially or completely instead of the diols monomeric or oligomeric polyols based on ethylene glycol, propylene glycol, tetrahydrofuran or copolymers thereof with molecular weights up to 4000, preferably up to 1000, and / or small amounts of branched bifunctional alcohols, if appropriate , preferably C 3 -C 12 -
  • Alkyl diols such as neopentyl glycol and, if necessary, small amounts of higher functional alcohols, preferably C 3 -C 12 alkyl polyols such as 1,2,3-propanetriol or trimethylol propane, and from aliphatic bifunctional acids, preferably C 2 -C 12 alkyl dicarboxylic acids such as and preferably succinic acid or
  • Adipic acid and / or optionally aromatic bifunctional acids such as terephthalic acid or isophthalic acid or naphthalenedicarboxylic acid and additionally optionally small amounts of higher functional acids such as trimellitic acid or
  • aromatic acids not more than 50 wt .-%, based on all
  • acids can also be used in the form of derivatives such as acid chlorides or esters, both as monomeric and as oligomeric esters;
  • Aliphatic or partially aromatic polyester urethanes C) aliphatic bifunctional alcohols, preferably linear C 2 -C ] 0 dialcohols such as ethanediol, butanediol, hexanediol, particularly preferably butanediol and / or optionally cycloaliphatic bifunctional alcohols, preferably with a C 5 -C 6 cycloaliphatic ring such as for example cyclohexanedimethanol and / or partially or completely instead of
  • aromatic acids making up no more than 50% by weight, based on all acids.
  • acids can also be used in the form of derivatives such as acid chlorides or esters, both as monomeric and as oligomeric esters;
  • cycloaliphatic see isocyanates for example tetramethylene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, if additionally with linear and / or branched and / or cycloaliphatic bifunctional and / or higher-functional alcohols, preferably C 3 -C 12 -alkyl di- or polyols or 5 to 8 C atoms in the case of cycloaliphatic alcohols, for example ethanediol, Hexanediol, butanediol, cyclohexanedimethanol, and / or optionally additionally with linear and / or branched and / or cycloaliphatic bifunctional and / or higher functional amines and / or amino alcohols with preferably 2 to 12 carbon atoms of the alkyl chain, e.g. Ethylene diamine or aminoethanol, and / or optionally further modified
  • ester content C) and / or D) is at least 75% by weight, based on the sum of C), D) and E), where, in the case of polymer structure typical of polyurethane, optionally from soft segments C) and D) and also from Hard segments E) a complete statistical distribution of the raw materials in the polymer is not to be expected;
  • aliphatic bifunctional alcohols preferably linear C 2 -C 10 dialcohols such as, for example, ethanediol, butanediol, hexanediol, particularly preferably butanediol and / or optionally cycloaliphatic bifunctional alcohols, preferably having 5 to 8 carbon atoms in the cyclo ⁇ aliphatic ring, such as cyclohexanedimethanol and / or partially or completely instead of the diols, monomeric or oligomeric polyols based on ethylene glycol, propylene glycol, tetrahydrofuran or copolymers thereof with molecular weights up to 4000, preferably up to 1000, and / or optionally small amounts of branched bifunctional alcohols, preferably C 3 -C 12 -alkyldiols such as neopentylglycol and additionally optionally small amounts of higher-functional alcohols, preferably C 3
  • G from acid- and alcohol-functionalized building blocks, preferably with 2 to 12 carbon atoms in the alkyl chain, for example hydroxybutyric acid or hydroxyvaleric acid or lactic acid, or their derivatives, for example ⁇ -caprolactone or dilactide,
  • aromatic acids making up no more than 50% by weight, based on all acids.
  • acids can also be used in the form of derivatives such as acid chlorides or esters, both as monomeric and as oligomeric esters;
  • ester fraction F) and / or G) must be at least 70% by weight, based on the sum of F), G) and H);
  • Dialcohols such as ethanediol, butanediol, hexanediol, particularly preferably butanediol and / or optionally cycloaliphatic bifunctional alcohols, preferably having 5 to 8 carbon atoms such as, for example, cyclohexanedimethanol and / or partially or completely instead of the diols, monomeric or oligomeric polyols based on ethylene glycol, Propylene glycol, tetrahydrofuran or copolymers thereof with molecular weights up to 4000, preferably up to 1000, and / or optionally small amounts of branched bifunctional alcohols, preferably C 3 - C 12 alkyldiols such as neopentyl glycol and, if appropriate, small amounts of higher functional alcohols, preferably C 3 -C 12 alkyl polyols such as 1,2,3-propanetriol or trimethylol propane and from aliphatic bi
  • Succinic acid or adipic acid and / or optionally aromatic bifunctional acids such as terephthalic acid or isophthalic acid or naphthalenedicarboxylic acid and additionally optionally small amounts of higher functional acids such as trimellitic acid or
  • acids can also be used in the form of derivatives such as acid chlorides or esters, both as monomeric and as oligomeric esters,
  • Atoms in the alkyl chain or C 5 -C 6 ring in the case of cycloaliphatic acids preferably adipic acid and / or optionally small amounts of branched bifunctional and / or optionally aromatic bifunctional acids such as, for example, terephthalic acid or isophthalic acid or naphthalenedicarboxylic acid and additionally optionally small amounts gene higher functional acids, preferably with 2 to 10 carbon atoms or M) from an amide portion of acid- and amine-functionalized building blocks, preferably with 4 to 20 carbon atoms in the cycloaliphatic chain, preferably ⁇ -laurolactam and ⁇ -caprolactam, particularly preferably ⁇ -caprolactam,
  • the ester content I) and / or K) must be at least 30% by weight, based on the sum of I), K), L) and M).
  • the proportion by weight of the ester structures is preferably between 30 and 70%, the proportion of the amide structures between 70 and 30%.
  • the biodegradable polyesteramides according to the invention can be synthesized either by the "polyamide method” by stoichiometric mixing of the starting components, if appropriate with the addition of water and subsequent removal of water from the reaction mixture, or by the “polyester method” by stoichiometric mixing of the starting components and additions of an excess of diol with esterification of the acid groups and subsequent transesterification or transamidation of these esters. In this second case, the excess diol is distilled off in addition to water. Preference is given to synthesis by the "polyester method” described.
  • polyesters, polyester urethanes, polyester carbonates or preferably polyester amides according to the invention can furthermore contain 0.1 to 5% by weight, preferably 0.1 to
  • branching 1 wt .-% of branching contain.
  • These branchers can e.g. trifunctional alcohols such as trimethylolpropane or glycerol, tetrafunctional alcohols such as pentaerythritol, trifunctional carboxylic acids such as citric acid.
  • the branching agents increase the melt viscosity of the polyester amides according to the invention to such an extent that extrusion blow molding with these polymers is possible. This does not hinder the biodegradation of these materials.
  • the polycondensation can also be accelerated by using known catalysts. Both the known phosphorus compounds, which accelerate the polyamide synthesis, and acidic or organometallic catalysts for the esterification, as well as combinations of the two, are possible to accelerate the polycondensation. Care must be taken to ensure that the catalysts do not adversely affect the biodegradability or compostability or the quality of the resulting compost.
  • polycondensation to polyester amides can be influenced by the use of lysine, lysine derivatives or other amidically branching products such as, for example, aminoethylaminoethanol, which both accelerate the condensation and lead to branched products (see, for example, DE 38 31 709).
  • Solvents which can be used according to the invention can be alcohols, ketones, ethers, halogenated or halogen-free hydrocarbons or esters. Are preferred
  • Solvents which can be used according to the invention can also be mixtures of the solvents mentioned and mixtures including other solvents such as water.
  • the concentrations of the solutions are between 70% by weight and 1% by weight of polymer, preferably between 50% by weight and 8% by weight of polymer, particularly preferably between 40% by weight and 19% by weight of polymer.
  • Additives such as fillers or additives such as adhesion improvers or viscosity influencers can also be added to the adhesive solutions according to the invention.
  • the present invention furthermore relates to a process for bonding compostable materials while maintaining the compostability of the entire composite, characterized in that solutions of compostable adhesives corresponding to the composition according to the invention are used for the bonding.
  • the present invention furthermore relates to a method for bonding compostable materials while maintaining the compostability of the entire composite, characterized in that the preparation of the solutions Postable adhesives that are used for gluing are prepared in a suitable gluing device, preferably at temperatures above 60 ° C., particularly preferably at temperatures above 70 ° C. and used immediately (in no longer than 10 minutes) for gluing. This can be done discontinuously or, preferably, continuously.
  • the present invention furthermore relates to a method for bonding compostable materials while maintaining the compostability of the entire composite, characterized in that the curing of the adhesive bond is accelerated.
  • This can be done, for example, by physical means such as accelerated removal of the solvent, for example in vacuo or at elevated temperature, or, for example, by adding crystallization accelerators (nucleating agents).
  • the materials to be bonded with the adhesives according to the invention can be leather, ceramic, wood, cardboard, paper or plastics.
  • the present invention furthermore relates to the use of a solution containing the abovementioned biodegradable polymers as an adhesive.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Biological Depolymerization Polymers (AREA)
  • Polyamides (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

L'invention concerne un adhésif compostable, son procédé de fabrication et son utilisation pour coller des pièces.
EP97920622A 1996-04-18 1997-04-07 Adhesif compostable Withdrawn EP0894122A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19615151A DE19615151A1 (de) 1996-04-18 1996-04-18 Kompostierbarer Klebstoff
DE19615151 1996-04-18
PCT/EP1997/001722 WO1997040114A1 (fr) 1996-04-18 1997-04-07 Adhesif compostable

Publications (1)

Publication Number Publication Date
EP0894122A1 true EP0894122A1 (fr) 1999-02-03

Family

ID=7791527

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97920622A Withdrawn EP0894122A1 (fr) 1996-04-18 1997-04-07 Adhesif compostable

Country Status (7)

Country Link
US (1) US6307003B1 (fr)
EP (1) EP0894122A1 (fr)
JP (1) JP2000508699A (fr)
AU (1) AU729239B2 (fr)
CA (1) CA2251821A1 (fr)
DE (1) DE19615151A1 (fr)
WO (1) WO1997040114A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19845152A1 (de) * 1998-10-01 2000-04-20 Merck Patent Gmbh Bioabbaubare Polyester-Oligomere
US8283435B2 (en) * 2003-02-21 2012-10-09 Metabolix, Inc. PHA adhesive compositions
WO2004076583A1 (fr) * 2003-02-21 2004-09-10 Metabolix Inc. Compositions adhesives de pha
EP1964879B1 (fr) * 2003-12-30 2012-06-13 Metabolix, Inc. Agents de nucléation
KR20080044274A (ko) * 2005-09-08 2008-05-20 다우 글로벌 테크놀로지스 인크. 폴리에스테르-아미드계 핫 멜트 접착제
JP5437801B2 (ja) * 2006-07-14 2014-03-12 デュポン・テイジン・フィルムズ・ユー・エス・リミテッド・パートナーシップ 多層シーラントフィルム
KR101322099B1 (ko) * 2008-07-08 2013-10-25 (주)엘지하우시스 친환경 생분해성 광고용 소재
CN104755538B (zh) 2012-08-17 2018-08-31 Cj 第一制糖株式会社 用于聚合物共混物的生物基橡胶改性剂
US10669417B2 (en) 2013-05-30 2020-06-02 Cj Cheiljedang Corporation Recyclate blends
US10611903B2 (en) 2014-03-27 2020-04-07 Cj Cheiljedang Corporation Highly filled polymer systems
KR102190917B1 (ko) 2018-08-31 2020-12-15 씨제이제일제당 주식회사 점착 조성물, 및 이의 제조방법

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1930336C3 (de) 1969-06-14 1978-12-14 Bayer Ag, 5090 Leverkusen Verwendung von Polyurethanen zur Herstellung von Klebstoffen mit hoher Anfangsfestigkeit
US4234305A (en) 1977-11-24 1980-11-18 Canon Kabushiki Kaisha Transfer sheet guiding device
US4584362A (en) 1985-02-27 1986-04-22 Cosan Chemical Corporation Bismuth catalyst system for preparing polyurethane elastomers
DE4234305A1 (de) 1992-10-12 1994-04-14 Bayer Ag Kompostierbarer Schmelzklebstoff
US5654380A (en) 1994-05-23 1997-08-05 Mitsubishi Gas Chemical Company, Inc. Aliphatic polyester carbonate and process for producing the same
JP3395375B2 (ja) * 1994-06-24 2003-04-14 東洋紡績株式会社 塗料用樹脂組成物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9740114A1 *

Also Published As

Publication number Publication date
CA2251821A1 (fr) 1997-10-30
US6307003B1 (en) 2001-10-23
AU2693997A (en) 1997-11-12
WO1997040114A1 (fr) 1997-10-30
DE19615151A1 (de) 1997-10-23
AU729239B2 (en) 2001-01-25
JP2000508699A (ja) 2000-07-11

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