GB1482887A - Process for the preparation of terpene-phenol resins - Google Patents
Process for the preparation of terpene-phenol resinsInfo
- Publication number
- GB1482887A GB1482887A GB977776A GB977776A GB1482887A GB 1482887 A GB1482887 A GB 1482887A GB 977776 A GB977776 A GB 977776A GB 977776 A GB977776 A GB 977776A GB 1482887 A GB1482887 A GB 1482887A
- Authority
- GB
- United Kingdom
- Prior art keywords
- terpene
- catalyst
- phenol
- reacting
- rubbers
- 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.)
- Expired
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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1482887 Terpene - phenol resins LES DERIVES RESINIQUES ET TERPENIQUES 11 March 1976 [16 April 1975] 09777/76 Heading C3R A terpene-phenol resin is prepared by a process comprising: (a) reacting 1 mole of a terpene with 1À8 to 2À2 moles of a phenol having at least 2 reactive sites, in the presence of an acidic condensation catalyst, to give a diphenolterpene, (b) reacting the resultant diphenolterpene, in the presence of said catalyst, with a terpene in an amount such that reactive sites remain on the resulting substituted diphenol-terpene molecule on completion of the reaction, and (c) reacting 1 mole of the substituted diphenol-terpene with 0À2 to 1À5 moles, calculated as formaldehyde, of a reagent providing methylene bridges, e.g. formaldehyde, formal, paraformaldehyde and hexamethylenetetramine; and optionally (d) heating the resin obtained in step (c) in the presence of zinc powder. The residual catalyst, if any, is preferably removed from the product obtained in step (c) or after the treatment with zinc powder, e.g. by adding lime at 100‹ C. to which an absorbent earth is added. Steps (a) and (b) are preferably carried out at a temperature of 80-120‹ C. and step (c) at a temperature of 90-120‹ C. Steps (a) to (c) are preferably carried out in the presence of a solvent, preferably an aromatic hydrocarbon. Suitable terpenes are #<SP>3</SP>-carene, #<SP>2</SP>-carene, α-pinene, #-pinene, camphene, limonene, isolimonene, dipentene or a mixture thereof. The phenol may be selected from hydroxybenzene, cresols, xylenols, thymol, naphthols, resorcinol or mixtures thereof. The catalyst may be a Lewis acid or a Friedel- Crafts catalyst preferably boron trifluoride or a complex thereof. The solvent may be removed by distillation. The resulting resin is compatible with natural rubber, SBR rubbers, neoprene, acrylo - nitrile - butadiene rubbers, chlorinated rubbers, ethylene-vinyl acetate copolymers, polyamides, polyethylene waxes, polyterpenic resins, rosins and esterified rosins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7511780A FR2307836A1 (en) | 1975-04-16 | 1975-04-16 | PROCESS FOR PREPARING TERPENE-PHENOL RESINS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1482887A true GB1482887A (en) | 1977-08-17 |
Family
ID=9154005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB977776A Expired GB1482887A (en) | 1975-04-16 | 1976-03-11 | Process for the preparation of terpene-phenol resins |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE839242A (en) |
| DE (1) | DE2616592C2 (en) |
| FI (1) | FI62546C (en) |
| FR (1) | FR2307836A1 (en) |
| GB (1) | GB1482887A (en) |
| IT (1) | IT1058771B (en) |
| NL (1) | NL176001C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018071891A1 (en) | 2016-10-14 | 2018-04-19 | Kraton Chemical, Llc | Rubber compositions containing improved tread enhancement additives and use thereof |
| WO2020144126A1 (en) * | 2019-01-10 | 2020-07-16 | Tesa Se | Use of thermally stable terpene-phenol resins |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3138180A1 (en) * | 1981-09-25 | 1983-04-14 | Bayer Ag, 5090 Leverkusen | NEW PHENOLS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS STABILIZERS FOR POLYMERS |
| ES2086474T3 (en) * | 1990-05-23 | 1996-07-01 | Shell Int Research | ADDICTS OF PHENOLIC COMPOUNDS AND CYCLIC TERPENES AND DERIVATIVES OF SUCH ADDUTS. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE340989C (en) * | 1919-05-04 | 1921-09-20 | Bakelite Ges M B H | Process for the preparation of benzene- and oil-soluble resinous condensation products from phenols and aldehydes |
| GB459549A (en) * | 1934-07-17 | 1937-01-11 | Beck Koller & Co England | A process for the manufacture of resinous condensation products |
-
1975
- 1975-04-16 FR FR7511780A patent/FR2307836A1/en active Granted
-
1976
- 1976-03-05 BE BE164894A patent/BE839242A/en not_active IP Right Cessation
- 1976-03-11 GB GB977776A patent/GB1482887A/en not_active Expired
- 1976-03-22 FI FI760757A patent/FI62546C/en not_active IP Right Cessation
- 1976-04-01 IT IT6775676A patent/IT1058771B/en active
- 1976-04-12 NL NL7603880A patent/NL176001C/en not_active IP Right Cessation
- 1976-04-14 DE DE19762616592 patent/DE2616592C2/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018071891A1 (en) | 2016-10-14 | 2018-04-19 | Kraton Chemical, Llc | Rubber compositions containing improved tread enhancement additives and use thereof |
| CN109843942A (en) * | 2016-10-14 | 2019-06-04 | 科腾化学品有限责任公司 | Rubber composition and application thereof containing improved tyre surface reinforced additive |
| EP3512890A4 (en) * | 2016-10-14 | 2020-06-03 | Kraton Chemical, LLC. | Rubber compositions containing improved tread enhancement additives and use thereof |
| WO2020144126A1 (en) * | 2019-01-10 | 2020-07-16 | Tesa Se | Use of thermally stable terpene-phenol resins |
| US12043767B2 (en) | 2019-01-10 | 2024-07-23 | Tesa Se | Use of thermally stable terpene-phenol resins |
Also Published As
| Publication number | Publication date |
|---|---|
| NL176001C (en) | 1985-02-01 |
| DE2616592A1 (en) | 1976-10-28 |
| NL7603880A (en) | 1976-10-19 |
| BE839242A (en) | 1976-09-06 |
| NL176001B (en) | 1984-09-03 |
| FI760757A (en) | 1976-10-17 |
| FI62546C (en) | 1983-01-10 |
| FI62546B (en) | 1982-09-30 |
| FR2307836A1 (en) | 1976-11-12 |
| DE2616592C2 (en) | 1982-10-21 |
| FR2307836B1 (en) | 1977-11-10 |
| IT1058771B (en) | 1982-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 746 | Register noted 'licences of right' (sect. 46/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19960310 |