GB1493760A - Polyhydroxy phenols and process for their preparation - Google Patents
Polyhydroxy phenols and process for their preparationInfo
- Publication number
- GB1493760A GB1493760A GB4239176A GB4239176A GB1493760A GB 1493760 A GB1493760 A GB 1493760A GB 4239176 A GB4239176 A GB 4239176A GB 4239176 A GB4239176 A GB 4239176A GB 1493760 A GB1493760 A GB 1493760A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- derivative
- water
- dimethylol
- phase
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/08—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols from phenol-aldehyde condensates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- 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
- C08G8/24—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20
Abstract
1493760 Polyhydroxyphenols and their production SOC ITALIANA RESINE SIR SpA 12 Oct 1976 [30 Oct 1975] 42391/76 Heading C2C The invention relates to a polyhydroxyphenol of formula where R is an alkyl radical containing from 1 to 10 carbon atoms, the methylene bridges being bonded to the central phenol ring in the orthopositions in relation to the hydroxyl group, and to the other phenol rings in the ortho- or para-position in relation to the hydroxyl group. This compound may be obtained by a process comprising the steps of (a) reacting formaldehyde and a substituted phenol of formula where R is an alkyl radical containing from 1 to 10 carbon atoms, in a formaldehyde/phenol molar ratio of at least 2 : 1, preferably from 2 : 1 to 3 : 1, in the presence of an inorganic base and at a temperature of at least 40‹ C., preferably 40‹ to 80‹ C. thereby to form a dimethylol derivative of said phenol, preferably the reaction mixture of this step does not contain more than 50% by weight of water; (b) adding an acid, e.g. HCl, H 2 SO 4 and phosphoric acids, to the reaction products of (a) in an amount at least equivalent to that of said inorganic base and in the presence of water, and separating the aqueous phase and the dimethylol derivative phase thus obtained; (c) adding to said dimethylol derivative phase an organic solvent capable of dissolving said derivative, normally immiscible or slightly miscible with water and forming with the latter an azeotropic mixture, contacting the resulting solution with phenol in a molar ratio between said phenol and said derivative of at least 2 :1, preferably 2 to 3À5 in the presence of an acid catalyst, e.g. oxalic, benzoic, p-tertiarybutylbenzoic, salicylic and isophthalic acids, and at a temperature of at least 100‹ C., preferably 100‹ to 160‹ C., and maintaining the resulting mixture at boiling point until substantially complete reaction of said derivative with said phenol, while distilling the forming water as an azeotrope with said organic solvent; and (d) recovering the polyhydroxy phenol from the reaction products of (c).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2880975A IT1043743B (en) | 1975-10-30 | 1975-10-30 | POLYUSSIORILIC PHENOLS AND PROCEDURE FOR THEIR PREPARATION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1493760A true GB1493760A (en) | 1977-11-30 |
Family
ID=11224223
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4239176A Expired GB1493760A (en) | 1975-10-30 | 1976-10-12 | Polyhydroxy phenols and process for their preparation |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5257153A (en) |
| CA (1) | CA1078874A (en) |
| DE (1) | DE2648051A1 (en) |
| FR (1) | FR2329631A1 (en) |
| GB (1) | GB1493760A (en) |
| IT (1) | IT1043743B (en) |
| NL (1) | NL7612021A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4173541A (en) | 1978-06-05 | 1979-11-06 | Cincinnati Milacron Chemicals Inc. | Polynuclear hindered phenols and stabilized organic materials containing the phenols |
| EP1637337A1 (en) * | 2003-06-25 | 2006-03-22 | Asahi Kasei Chemicals Corporation | Developer for recording materials |
| US20150322193A1 (en) * | 2014-05-12 | 2015-11-12 | Si Group, Inc. | Modified phenolic resins and methods of making and using the same as reinforcing resins |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62119220A (en) * | 1985-11-18 | 1987-05-30 | Arakawa Chem Ind Co Ltd | Production of polyhydroxyl compound |
| JP2005232038A (en) * | 2004-02-17 | 2005-09-02 | Sumitomo Bakelite Co Ltd | Phenol compound and method for producing the same |
| WO2006075604A1 (en) * | 2005-01-11 | 2006-07-20 | Oji Paper Co., Ltd. | Thermosensitive recording material |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744882A (en) * | 1949-01-26 | 1956-05-08 | Union Carbide & Carbon Corp | Unsymmetrical diphenylol methanes |
| DE915341C (en) * | 1950-09-06 | 1954-07-19 | Union Carbide & Carbon Corp | Process for the preparation of triphenylene compounds |
| US2841627A (en) * | 1952-10-10 | 1958-07-01 | Monsanto Chemicals | Method of preserving a rubber with an alpha, alpha'-bis(hydroxyphenyl)-2, 6-xylenol ad resulting compositions |
| US2773907A (en) * | 1954-02-05 | 1956-12-11 | American Cyanamid Co | Tris-phenols |
| GB928169A (en) * | 1960-12-02 | 1963-06-06 | Distillers Co Yeast Ltd | Trinuclear phenol antioxidants |
-
1975
- 1975-10-30 IT IT2880975A patent/IT1043743B/en active
-
1976
- 1976-10-12 GB GB4239176A patent/GB1493760A/en not_active Expired
- 1976-10-19 CA CA263,674A patent/CA1078874A/en not_active Expired
- 1976-10-23 DE DE19762648051 patent/DE2648051A1/en not_active Ceased
- 1976-10-29 JP JP13040876A patent/JPS5257153A/en active Pending
- 1976-10-29 FR FR7632819A patent/FR2329631A1/en active Granted
- 1976-10-29 NL NL7612021A patent/NL7612021A/en not_active Application Discontinuation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4173541A (en) | 1978-06-05 | 1979-11-06 | Cincinnati Milacron Chemicals Inc. | Polynuclear hindered phenols and stabilized organic materials containing the phenols |
| EP1637337A1 (en) * | 2003-06-25 | 2006-03-22 | Asahi Kasei Chemicals Corporation | Developer for recording materials |
| EP1637337A4 (en) * | 2003-06-25 | 2006-11-22 | Asahi Kasei Chemicals Corp | Developer for recording materials |
| US20150322193A1 (en) * | 2014-05-12 | 2015-11-12 | Si Group, Inc. | Modified phenolic resins and methods of making and using the same as reinforcing resins |
| WO2015175551A1 (en) * | 2014-05-12 | 2015-11-19 | Si Group, Inc. | Modified phenolic resins and methods of making and using the same as reinforcing resins |
| CN106536585A (en) * | 2014-05-12 | 2017-03-22 | Si集团有限公司 | Modified phenolic resins and methods of making and using the same as reinforcing resins |
| JP2017515941A (en) * | 2014-05-12 | 2017-06-15 | エスアイ・グループ・インコーポレイテッドSi Group, Inc. | Modified phenolic resin and method for producing and using it as a reinforcing resin |
| US9765174B2 (en) * | 2014-05-12 | 2017-09-19 | Si Group, Inc. | Modified phenolic resins and methods of making and using the same as reinforcing resins |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2329631B1 (en) | 1981-12-04 |
| FR2329631A1 (en) | 1977-05-27 |
| IT1043743B (en) | 1980-02-29 |
| NL7612021A (en) | 1977-05-03 |
| JPS5257153A (en) | 1977-05-11 |
| CA1078874A (en) | 1980-06-03 |
| DE2648051A1 (en) | 1977-05-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 746 | Register noted 'licences of right' (sect. 46/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |