GB942594A - Polyhydric phenols - Google Patents
Polyhydric phenolsInfo
- Publication number
- GB942594A GB942594A GB2110161A GB2110161A GB942594A GB 942594 A GB942594 A GB 942594A GB 2110161 A GB2110161 A GB 2110161A GB 2110161 A GB2110161 A GB 2110161A GB 942594 A GB942594 A GB 942594A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphides
- bis
- hydroxy
- tetra
- butyl
- 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
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/115—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using acetals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention comprises tetraphenols of the formula: <FORM:0942594/C2/1> where X and Y are alkyl groups and R is a hydrocarbon group and a method for the preparation of these compounds by reacting substantially four molecular equivalents of a phenol with a dialdehyde or a dialdehyde precursor in a solvent, for example an alcohol such as ethanol or a hydrocarbon such as benzene toluene or oxylene in the presence of an acidic catalyst e.g. zinc chloride or hydrogen chloride. The dialdehyde precursor may be a diacetal, e.g. 1:1:3:3tetraethoxypropane or a cyclic acetal e.g. 2ethoxy-3:4-dihydro-2H-pyran. The group R may be methylene, ethylene, trimethylene, o-, m- or p-phenylene, or 2:21-diphenylene and groups X and Y may be methyl, ethyl, isopropyl, t-butyl or t-octyl. Detailed examples are given of the preparation of 1:4-bis [di-(5-t-butyl-4hydroxy - 2 methyl - phenyl) - methyl] - benzene, 1:4 - bis [di - (4 - hydroxy - 2:5 - dimethylphenyl) methyl] benzene, 1:1:3:3 - tetra (5 - t - butyl 4 - hydroxy - 2 - methylphenyl) propane, 1:1:4:4 tetra (5 - t - butyl - 4 - hydroxy - 2 - methylphenyl) butane, 1:1:5:5 - tetra (5 - t - butyl - 4 - hydroxy2 - methylhenyl) pentane while brief reference is made to 1:1:4:4 - tetra (4 - hydroxy - 2:5 dimethylphenyl) butane and 1:1:5:5 - tetra (4 hydroxy - 2:5 - dimethyl phenyl) pentane. The compounds are used to stabilize hydrocarbon polymers (see Division C3). The Provisional Specifications refer also to compounds of the formula: <FORM:0942594/C2/2> wherein R is a hydrocarbon group, the hydroxyl groups are positioned ortho or para to the CH groups and wherein the nuclei A may carry alkyl and/or halogen groups as substituents.ALSO:Tetraphenols of the formula: <FORM:0942594/C3/1> where X and Y are alkyl groups and R is a hydrocarbon group are used to stabilise polyethylene and polypropylene. Sulphides or polysulphides may also be added to the polymer to increase the stabilizing effect of the tetraphenolic compounds. Sulphides mentioned are dialkyl sulphide e.g. dodecyl sulphide, di (substituted alkyl) sulphides, particularly esters of bis-carboxyalkyl sulphides e.g. tetra-n-hexyl ester of di(b :g -dicarboxy propyl) sulphide and dilauryl or dioctadecyl thiodipropionates or thiodibutyrates, dibenzyl sulphides e.g. bis(2-hydroxy-5-methylbenzyl)-sulphide and bis(3-tert-butyl-2-hydroxy-5-methoxy-benzyl) sulphide, diaryl sulphides e.g. diphenyl sulphides, dicresyl sulphides, 2:21-dihydroxy-5:51-dimethyl diphenyl disulphide, and diphenyldisulphide, dialkyldithio-phosphates such as bis(diisopropyl-dithiophosphory) disulphide and bis(dinonyl dithiophosphorylmethylene) thiourea, and dialkyldithiophosphatomethyl-phenols e.g. 4-methyl-2- (O:O1-dinonyldithiophosphatomethyl) phenol and 4-methyl-2:6-bis-(O:O1 - dinonyldithiophosphatomethyl) phenol. The stabilising effect of the mixture of tetraphenolic compounds and sulphides or polysulphides is enhanced, particularly when the polymer contains copper compounds or will come into contact with copper, by the addition of amines and amine derivatives. Amines and amine derivatives mentioned are 4:41-diaminodiphenylmethane, alkylene diamines, ethyleneimine polymers e.g. triethylene tetramine and diethylene triamine, N:N1-di (b -aminoethyl) piperazine, disalicylideneethylene diamine and mercaptbenzimidazole. The Provisional Specifications refer also to stabilizing polyethylene or polypropylene by the addition of a compound of the formula: <FORM:0942594/C3/2> wherein r is a hydrocarbon group, the hydroxyl groups are positioned ortho or para to the CH groups and wherein the nuclei A may carry alkyl and/or halogen group as substituents.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE618841D BE618841A (en) | 1961-06-12 | ||
NL279609D NL279609A (en) | 1961-06-12 | ||
GB2110161A GB942594A (en) | 1961-06-12 | 1961-06-12 | Polyhydric phenols |
US200677A US3309337A (en) | 1961-06-12 | 1962-06-07 | Polyethylene and polypropylene stabilized with tetraphenolic compounds |
DEJ21906A DE1235582B (en) | 1961-06-12 | 1962-06-08 | Process for stabilizing polyethylene or polypropylene |
DEI32030A DE1297865B (en) | 1961-06-12 | 1962-06-08 | Process for stabilizing polyethylene or polypropylene |
FR900453A FR1329787A (en) | 1961-06-12 | 1962-06-12 | Production and application of tetraphenols |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2110161A GB942594A (en) | 1961-06-12 | 1961-06-12 | Polyhydric phenols |
Publications (1)
Publication Number | Publication Date |
---|---|
GB942594A true GB942594A (en) | 1963-11-27 |
Family
ID=10157241
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2110161A Expired GB942594A (en) | 1961-06-12 | 1961-06-12 | Polyhydric phenols |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB942594A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5012016A (en) * | 1990-03-20 | 1991-04-30 | Shell Oil Company | Process for preparing tetraphenolic compounds |
WO2009114383A1 (en) * | 2008-03-12 | 2009-09-17 | Dow Global Technologies Inc. | Polyphenolic compounds and epoxy resins comprising cycloaliphatic moieties and process for the production thereof |
WO2011023756A3 (en) * | 2009-08-31 | 2011-06-23 | Evonik Oxeno Gmbh | Organophosphorus compounds based on tetraphenol (tp)-substituted structures |
-
1961
- 1961-06-12 GB GB2110161A patent/GB942594A/en not_active Expired
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5012016A (en) * | 1990-03-20 | 1991-04-30 | Shell Oil Company | Process for preparing tetraphenolic compounds |
WO2009114383A1 (en) * | 2008-03-12 | 2009-09-17 | Dow Global Technologies Inc. | Polyphenolic compounds and epoxy resins comprising cycloaliphatic moieties and process for the production thereof |
CN102026949A (en) * | 2008-03-12 | 2011-04-20 | 陶氏环球技术公司 | Polyphenolic compounds and epoxy resins comprising cycloaliphatic moieties and process for the production thereof |
EP2703378A1 (en) * | 2008-03-12 | 2014-03-05 | Dow Global Technologies LLC | Polyphenolic compounds and epoxy resins comprising cycloaliphatic moieties and process for the production thereof |
WO2011023756A3 (en) * | 2009-08-31 | 2011-06-23 | Evonik Oxeno Gmbh | Organophosphorus compounds based on tetraphenol (tp)-substituted structures |
CN102574798A (en) * | 2009-08-31 | 2012-07-11 | 赢创奥克森诺有限责任公司 | Organophosphorus compounds based on tetraphenol (tp)-substituted structures |
US9000220B2 (en) | 2009-08-31 | 2015-04-07 | Evonik Degussa Gmbh | Organophosphorus compounds based on tetraphenol (TP)-substituted structures |
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