WO2023170014A1 - Eco-friendly adhesive formulation containing 2-methyl tetrahydrofuran - Google Patents
Eco-friendly adhesive formulation containing 2-methyl tetrahydrofuran Download PDFInfo
- 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
Links
Classifications
-
- 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
- C09J111/00—Adhesives based on homopolymers or copolymers of chloroprene
-
- 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- 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
- C09J2411/00—Presence 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)
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)
| 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)
| 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 |
-
2023
- 2023-03-07 WO PCT/EP2023/055651 patent/WO2023170014A1/en not_active Ceased
- 2023-03-07 CN CN202380021905.4A patent/CN118715299A/zh active Pending
- 2023-03-07 US US18/845,768 patent/US20250197696A1/en active Pending
- 2023-03-07 EP EP23708510.5A patent/EP4490242A1/en active Pending
- 2023-03-07 JP JP2024547282A patent/JP2025507541A/ja active Pending
Patent Citations (6)
| 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)
| 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 |
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