WO2023170014A1 - Eco-friendly adhesive formulation containing 2-methyl tetrahydrofuran - Google Patents

Eco-friendly adhesive formulation containing 2-methyl tetrahydrofuran Download PDF

Info

Publication number
WO2023170014A1
WO2023170014A1 PCT/EP2023/055651 EP2023055651W WO2023170014A1 WO 2023170014 A1 WO2023170014 A1 WO 2023170014A1 EP 2023055651 W EP2023055651 W EP 2023055651W WO 2023170014 A1 WO2023170014 A1 WO 2023170014A1
Authority
WO
WIPO (PCT)
Prior art keywords
adhesive
polychloroprene
solvent
methyl tetrahydrofuran
organic solvent
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.)
Ceased
Application number
PCT/EP2023/055651
Other languages
English (en)
French (fr)
Inventor
Martin Ferdinand SCHNEIDER
Regina Yvonne FRIESE
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.)
Arlanxeo Deutschland GmbH
Original Assignee
Arlanxeo Deutschland 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 Arlanxeo Deutschland GmbH filed Critical Arlanxeo Deutschland GmbH
Priority to EP23708510.5A priority Critical patent/EP4490242A1/en
Priority to US18/845,768 priority patent/US20250197696A1/en
Priority to JP2024547282A priority patent/JP2025507541A/ja
Priority to CN202380021905.4A priority patent/CN118715299A/zh
Publication of WO2023170014A1 publication Critical patent/WO2023170014A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J111/00Adhesives based on homopolymers or copolymers of chloroprene
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2411/00Presence of chloroprene

Definitions

  • the present invention relates to an adhesive formulation preferably based on poly chloroprene, comprising a preferably bio-based solvent or solvent mixture with a long open time together with a high solution viscosity.
  • the adhesive formulation is eco-friendly.
  • Solvent borne contact adhesives can be based on a variety of polymers including polychloroprene, nitrile rubbers, polyurethanes, ethylene-propylene-diene-rubber, styrene-butadiene-styrene or styrene-isoprene-styrene blockcopolymers amongst others.
  • CA 2 527 561 discloses solvent-containing compositions based on polychloroprene.
  • the polymerization is halted at conversions of between 60% and 100%, and unconverted monomers are removed by devolatilization.
  • the dispersion is first adjusted to a pH of 5.5-7.0 by addition of dilute acetic acid.
  • the polychloroprene is recovered subsequently by deposition on the dispersion on a chilled roll (about -15°C) (freeze coagulation).
  • the thin, frozen polychloroprene layer is thawed, washed, dried, gathered to form a strand and chopped into chips.
  • Polychloroprene finds use in applications including rubber articles, and also in contact adhesives and sealants.
  • polychloroprene For the production of adhesives strongly crystallizing types of polychloroprene are predominantly used which can be obtained by emulsion polymerization at low temperatures (of lower than 15 °C). In addition polychloroprene with medium tendency to crystallize can be used, which are obtained by emulsion polymerization at temperatures between 15 and 40 °C.
  • the adhesives produced therefrom produce adhesive bonds which have high initial strength and which set rapidly. These properties are particularly important in all cases where the adhesive bond is exposed to high material stresses, such as for example when bonding highly arched soles in the shoe industry or curved surfaces in the furniture industry, and especially when the bonded articles have to undergo rapid further processing, such as for example on a conveyor belt.
  • Preferred types of polychloroprene to be used according to the invention have a solution viscosity (10% by weight in toluene) of 50 - 15,000 mPas at 23 °C.
  • the composition according to the invention is an adhesive composition and/or a sealant composition.
  • 2-methyl tetrahydrofuran is (commercially) available to the skilled person. [0037] In a preferred embodiment, 2-methyl tetrahydrofuran is understood to include the racemat, the (R) enantiomer and the (S) enantiomer.
  • the content of the first organic solvent, which is 2-methyl tetrahydrofuran is 5 to less than 100 wt-%, based on the total weight of the mixture, and the content of the second organic solvent, which is ethyl acetate, is greater than 0 to 95 wt-%, based on the total weight of the mixture;
  • the total amount of the first organic solvent, which is 2-methyl tetrahydrofuran, and of the second organic solvent, which is ethyl acetate, is preferably 100 wt-%, based on the total weight of the solvent mixture.
  • the compositions according to the invention do not comprise a solvent in addition to the first organic solvent, which is 2-methyl tetrahydrofuran, and the second organic solvent, which is ethyl acetate.
  • the compositions according to the invention additionally comprise further solvents, i.e. solvents in addition to the first organic solvent, which is 2-methyl tetrahydrofuran.
  • An optional second organic solvent is an alkylacetate, preferably ethyl acetate. Beyond or instead of alkylacetate, preferably ethyl acetate other organic solvents may be present.
  • Organic solvents are carbon-containing solvents.
  • the polychloroprene types of adhesives are soluble in many organic solvents and solvent mixtures. In the compositions according to the invention the polychloroprene is therefore present, at least partially, in dissolved form.
  • the solvent or solvent mixture to be used for the production of the adhesive is selected on the basis of commercial and technical factors, it being necessary to take into account, inter alia, that the solvent has a considerable effect on
  • aliphatic hydrocarbons and/or aromatic hydrocarbons having a variable chain length, degree of branching and molecular weight, paraffinic, naphthenic and aromatic oils and waxes and long-chain esters, alcohols, ketones, ethers, halogenated aliphatic and/or aromatic hydrocarbons and combinations/mixtures thereof.
  • Aliphatic, branched, straightchain, cyclic or aromatic hydrocarbons such as pentane, hexane, cyclohexane, methyl cyclohexane, heptane, octane, benzene, toluene, xylene, etc. and mixtures such as solvent naphtha or petrol are preferred.
  • mixtures of the abovementioned polar and non-polar solvents are particularly preferred.
  • a preferred solvent mixture consists of aliphatic esters and/or ketones and aliphatic and/or aromatic hydrocarbons.
  • the carbonates of these metals are occasionally also used; zinc carbonate has a more transparent appearance in the adhesive than zinc oxide.
  • the produced composition is an adhesive and/or sealant composition.
  • the adhesive compositions were produced in a direct dissolution process. For this process, all of the solid constituents, apart from polychloroprene and the ethylene-vinyl acetate copolymers, were charged to a closable container, the solvents were weighed in, and then the poly chloroprene was added. Dissolution was done with 4.5 cm dissolver disc at 23 °C with 1000 rpm.
  • Antioxidant 6PPD (Vulkanox 4020 LG) from Lanxess
  • compositions according to the invention exhibit a long open time in combination with a high solution viscosity, whereas the compositions according to JP 2003 226 852 do not exhibit such advantageous combination.
  • any reference to "%” in the description is preferably understood to represent “weight %", more preferably “weight %, based on the total weight of the composition according to the invention”.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Sealing Material Composition (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/EP2023/055651 2022-03-11 2023-03-07 Eco-friendly adhesive formulation containing 2-methyl tetrahydrofuran Ceased WO2023170014A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP23708510.5A EP4490242A1 (en) 2022-03-11 2023-03-07 Eco-friendly adhesive formulation containing 2-methyl tetrahydrofuran
US18/845,768 US20250197696A1 (en) 2022-03-11 2023-03-07 Eco-friendly adhesive formulation containing 2-methyl tetrahydrofuran
JP2024547282A JP2025507541A (ja) 2022-03-11 2023-03-07 2-メチルテトラヒドロフランを含有する、生態系にやさしい接着剤配合物
CN202380021905.4A CN118715299A (zh) 2022-03-11 2023-03-07 含有2-甲基四氢呋喃的生态友好的粘合剂配制品

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22161713.7 2022-03-11
EP22161713 2022-03-11

Publications (1)

Publication Number Publication Date
WO2023170014A1 true WO2023170014A1 (en) 2023-09-14

Family

ID=81074203

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2023/055651 Ceased WO2023170014A1 (en) 2022-03-11 2023-03-07 Eco-friendly adhesive formulation containing 2-methyl tetrahydrofuran

Country Status (5)

Country Link
US (1) US20250197696A1 (https=)
EP (1) EP4490242A1 (https=)
JP (1) JP2025507541A (https=)
CN (1) CN118715299A (https=)
WO (1) WO2023170014A1 (https=)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2234215A (en) 1939-03-28 1941-03-11 Du Pont Plastic polymeric derivatives of chloroprene and process of producing the same
US3488315A (en) 1967-08-09 1970-01-06 Exxon Research Engineering Co Neoprene cements with extended open time
US3933719A (en) 1973-03-07 1976-01-20 Nippon Oil Company Ltd. Polychloroprene-base adhesive composition
JP2003226852A (ja) 2002-02-04 2003-08-15 Aica Kogyo Co Ltd クロロプレンゴム系接着剤組成物
CA2527561A1 (en) 2003-05-30 2004-12-09 Lanxess Deutschland Gmbh Solvent-containing compositions based on polychloroprene
US20200216722A1 (en) * 2017-09-05 2020-07-09 Sika Technology Ag Adhesive composition and use thereof for providing a self-healing adhered roofing systems

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5952429A (en) * 1995-06-14 1999-09-14 Nippon Shokubai Co., Ltd. Carbon black graft polymer, method for production thereof, and use thereof
US5821299A (en) * 1996-02-16 1998-10-13 The Proctor & Gamble Company Solvent extraction of polyhydroxy-alkanoates from biomass facilitated by the use of marginal nonsolvent
JP4911143B2 (ja) * 2008-08-15 2012-04-04 信越化学工業株式会社 高温耐性接着剤組成物、基板の接着方法、及び3次元半導体装置
KR102592147B1 (ko) * 2018-04-20 2023-10-23 삼성전자주식회사 복합분리막, 그 제조방법 및 이를 포함하는 리튬이차전지

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2234215A (en) 1939-03-28 1941-03-11 Du Pont Plastic polymeric derivatives of chloroprene and process of producing the same
US3488315A (en) 1967-08-09 1970-01-06 Exxon Research Engineering Co Neoprene cements with extended open time
US3933719A (en) 1973-03-07 1976-01-20 Nippon Oil Company Ltd. Polychloroprene-base adhesive composition
JP2003226852A (ja) 2002-02-04 2003-08-15 Aica Kogyo Co Ltd クロロプレンゴム系接着剤組成物
CA2527561A1 (en) 2003-05-30 2004-12-09 Lanxess Deutschland Gmbh Solvent-containing compositions based on polychloroprene
US20200216722A1 (en) * 2017-09-05 2020-07-09 Sika Technology Ag Adhesive composition and use thereof for providing a self-healing adhered roofing systems

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
"Baypren adhesives product portfolio", 2021, ARLANXEO
SKEIST I, HANDBOOK OF ADHESIVES, vol. 3, 1990, pages 295
SKEIST I: "Handbook of Adhesives", vol. 3, 1990, pages: 295

Also Published As

Publication number Publication date
US20250197696A1 (en) 2025-06-19
CN118715299A (zh) 2024-09-27
JP2025507541A (ja) 2025-03-21
EP4490242A1 (en) 2025-01-15

Similar Documents

Publication Publication Date Title
US4028292A (en) Hot melt adhesive
EP0758009B1 (en) Hot melt adhesives for bonding to sensitive areas of the human body
EP2999760B1 (en) Hot melt adhesive based on low melting point polypropylene homopolymers
US5183705A (en) Pressure-sensitive adhesive composition having high shear strength
US10072186B2 (en) Farnesene-based tackifying resins and adhesive compositions containing the same
US6214935B1 (en) Intermediate softening point resin-based hot melt PSAs
AU2007338452B2 (en) Hot melt pressure sensitive adhesives for paper labels
KR20150045474A (ko) 아크릴레이트 및 스티렌 블록 공중합체의 접착제 블렌드를 갖는 접착제
EP4087882B1 (en) Farnesene-based tackifying resins and adhesive compositions containing the same
US3577372A (en) Hot melt adhesive compositions
US2697084A (en) Adhesives comprising polyvinyl ether
WO2023170014A1 (en) Eco-friendly adhesive formulation containing 2-methyl tetrahydrofuran
KR101299422B1 (ko) 중간 연화점 수지-기재 고온 용융 피에스에이에스
CN113412303A (zh) 包括水基面漆的制品
US3935135A (en) Heat-sealing adhesives
JPS61115977A (ja) 反応性ホツトメルト接着剤
JP5726411B2 (ja) エマルジョン型粘着剤及びこれを用いた粘着テープ
TWI300090B (en) Pressure sensitive adhesive and compositions prepared with same
WO2022150688A1 (en) A hot melt pressure sensitive adhesive composition
JP4438411B2 (ja) フェノール変性芳香族石油樹脂組成物及びそれよりなるホットメルト接着剤組成物
FR3079835A1 (fr) Additif pour feuille impermeable contenant de l'asphalte, procede de production d'une feuille impermeable contenant de l'asphalte, composition d'asphalte, et feuille impermeable contenant de l'asphalte
SE130036C1 (https=)
JP2025040156A (ja) ホットメルト組成物
Benedek et al. Design and formulation basis
EP4549327A1 (en) Protective coating for hot-melt pressure sensitive adhesives

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 23708510

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2024547282

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 202380021905.4

Country of ref document: CN

WWE Wipo information: entry into national phase

Ref document number: 18845768

Country of ref document: US

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112024018702

Country of ref document: BR

WWE Wipo information: entry into national phase

Ref document number: 2023708510

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2023708510

Country of ref document: EP

Effective date: 20241011

ENP Entry into the national phase

Ref document number: 112024018702

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20240911

WWP Wipo information: published in national office

Ref document number: 18845768

Country of ref document: US