GB790644A - Phenolic oxo-aldehyde resins - Google Patents
Phenolic oxo-aldehyde resinsInfo
- Publication number
- GB790644A GB790644A GB12714/55A GB1271455A GB790644A GB 790644 A GB790644 A GB 790644A GB 12714/55 A GB12714/55 A GB 12714/55A GB 1271455 A GB1271455 A GB 1271455A GB 790644 A GB790644 A GB 790644A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- hydrogen chloride
- catalyst
- resorcinol
- chloride gas
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Phenol-aldehyde resins are made by reacting phenols with oxo-aldehydes. Oxo-aldehydes are defined as aldehydes made by the oxonation of olefins with carbon monoxide and hydrogen. Specified phenols are those of the general formula C6H3OHRX, where R is a hydrogen atom or an alkyl group containing 1 to 20 carbon atoms and X is hydrogen or an hydroxy group, e.g. phenol, o-, m- or p-cresol, ethyl phenol, propyl or iso-propyl phenol, butyl phenol, tertiary-amyl phenol, resorcinol, dodecyl phenol, pentadecyl resorcinol, mixed phenols from coal tar or petroleum phenols. Preferred oxoaldehydes are those of the general formula X-CHO, where X is an alkyl group containing 4 to 9 carbon atoms. Acid or basic catalyst, e.g. hydrogen chloride gas, boron trifluoride or sodium hydroxide may be used for the condensation reaction. In the examples, an iso-octyl aldehyde is condensed with (1) phenol at a temperature of 100-110 DEG C., hydrogen chloride gas being passed into the reaction mixture; (2) phenol at 100 DEG C., boron trifluoride gas being passed into the reaction mixture; (3) phenol at 85 DEG C. or 100-110 DEG C. in the presence of aqueous caustic soda; (4) tertiary butyl phenol at 95-100 DEG C. using hydrogen chloride gas as catalyst; (5) dodecyl phenol at 100-110 DEG C. using hydrogen chloride gas as catalyst; (6) resorcinol at 20-30 DEG C. using hydrogen chloride gas as catalyst; (7) resorcinol at 40-50 DEG C. in the presence of aqueous caustic soda; (8) pentadecyl resorcinol with benzene as solvent at 80 DEG C. using gaseous hydrogen chloride as catalyst; (9) para-cresol at 100-110 DEG C. using gaseous hydrogen chloride as catalyst. The products may be used as modifiers for rubber or synthetic rubber or as plasticizer resins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US790644XA | 1954-05-27 | 1954-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB790644A true GB790644A (en) | 1958-02-12 |
Family
ID=22148188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12714/55A Expired GB790644A (en) | 1954-05-27 | 1955-05-02 | Phenolic oxo-aldehyde resins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB790644A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2642078A1 (en) * | 1989-01-25 | 1990-07-27 | Ceca Sa | FORMOPHENOLIC RESINS OF NOVOLAQUE TYPE RESULTING FROM THE CONDENSATION OF PHENOLS AND HEAVY ALDEHYDES. PREPARATION. THEIR APPLICATION TO STRENGTHENING RUBBER |
| EP0409403A2 (en) * | 1989-06-29 | 1991-01-23 | Zeneca Limited | Composition providing surface protection |
| FR2665165A1 (en) * | 1990-07-25 | 1992-01-31 | Ceca Sa | NEW NOVOLAQUE RESINS OF PARA-ALKYLPHENOLS. THEIR PREPARATION PROCESS. |
| JP2018532027A (en) * | 2015-10-29 | 2018-11-01 | ヘキシオン・インコーポレイテッド | Novel alkylphenol resin and preparation method thereof |
| US20190106566A1 (en) * | 2017-10-06 | 2019-04-11 | Hexion Inc. | Rubber compositions containing tackifiers |
| US10808068B2 (en) | 2018-01-26 | 2020-10-20 | Hexion Inc. | Manufacture of novolacs and resoles using lignin |
-
1955
- 1955-05-02 GB GB12714/55A patent/GB790644A/en not_active Expired
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2642078A1 (en) * | 1989-01-25 | 1990-07-27 | Ceca Sa | FORMOPHENOLIC RESINS OF NOVOLAQUE TYPE RESULTING FROM THE CONDENSATION OF PHENOLS AND HEAVY ALDEHYDES. PREPARATION. THEIR APPLICATION TO STRENGTHENING RUBBER |
| WO1990008790A1 (en) * | 1989-01-25 | 1990-08-09 | Ceca S.A. | Novel novolaks of the phenol-dense aldehyde type |
| AU631399B2 (en) * | 1989-01-25 | 1992-11-26 | Ceca S.A. | Novel novolaks of the phenol-dense aldehyde type |
| US5412058A (en) * | 1989-01-25 | 1995-05-02 | Ceca S.A. | Novolaks of the phenol-dense aldehyde type |
| EP0409403A2 (en) * | 1989-06-29 | 1991-01-23 | Zeneca Limited | Composition providing surface protection |
| EP0409403B1 (en) * | 1989-06-29 | 1995-08-02 | Zeneca Limited | Composition providing surface protection |
| FR2665165A1 (en) * | 1990-07-25 | 1992-01-31 | Ceca Sa | NEW NOVOLAQUE RESINS OF PARA-ALKYLPHENOLS. THEIR PREPARATION PROCESS. |
| EP0472446A2 (en) * | 1990-07-25 | 1992-02-26 | Ceca S.A. | Para-alkylphenol based novolak resins. Method for preparation therof |
| EP0472446A3 (en) * | 1990-07-25 | 1992-03-04 | Ceca S.A. | Para-alkylphenol based novolak resins. method for preparation therof |
| US10982034B2 (en) | 2015-10-29 | 2021-04-20 | Hexion Inc. | Alkylphenol resins and a method of preparing thereof |
| JP2018532027A (en) * | 2015-10-29 | 2018-11-01 | ヘキシオン・インコーポレイテッド | Novel alkylphenol resin and preparation method thereof |
| US11518839B2 (en) | 2015-10-29 | 2022-12-06 | Bakelite UK Holding Ltd. | Alkylphenol resins and a method of preparing thereof |
| US20190106566A1 (en) * | 2017-10-06 | 2019-04-11 | Hexion Inc. | Rubber compositions containing tackifiers |
| WO2019071117A1 (en) * | 2017-10-06 | 2019-04-11 | Hexion Inc. | Rubber compositions containing tackifiers |
| CN111247184A (en) * | 2017-10-06 | 2020-06-05 | 瀚森公司 | Rubber composition containing tackifier |
| US10696838B2 (en) | 2017-10-06 | 2020-06-30 | Hexion Inc. | Rubber compositions containing tackifiers |
| US10982087B2 (en) | 2017-10-06 | 2021-04-20 | Hexion Inc. | Rubber compositions containing tackifiers |
| AU2018346682B2 (en) * | 2017-10-06 | 2024-01-18 | Bakelite UK Holding Ltd. | Rubber compositions containing tackifiers |
| US10808068B2 (en) | 2018-01-26 | 2020-10-20 | Hexion Inc. | Manufacture of novolacs and resoles using lignin |
| US11697703B2 (en) | 2018-01-26 | 2023-07-11 | Bakelite UK Holding Ltd. | Manufacture of novolacs and resoles using lignin |
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