GB823544A - 2-hydroxy-4-alkoxy-4-alkylbenzophenones and compositions containing the same - Google Patents
2-hydroxy-4-alkoxy-4-alkylbenzophenones and compositions containing the sameInfo
- Publication number
- GB823544A GB823544A GB592456A GB592456A GB823544A GB 823544 A GB823544 A GB 823544A GB 592456 A GB592456 A GB 592456A GB 592456 A GB592456 A GB 592456A GB 823544 A GB823544 A GB 823544A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- alkyl
- para
- methoxy
- vinyl
- 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
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Abstract
The invention comprises 2-hydroxy-4-alkoxy-41-alkylbenzophenones in which the alkyl and alkoxy groups each contain up to eight carbon atoms. The compounds may be prepared by a Friedel Crafts reaction with a para toluyl halide or other para-alkylbenzoyl halide having not more than eight carbon atoms in the alkyl group, and a resorcinol mono or dialkyl ether in which the alkyl groups contain one to eight carbon atoms. Substantially equimolecular quantities of the two reactants may be used. Resorcinol itself may also be employed as the second reactant in which case the product is a 2,4, dihydroxy 41-alkyl-benzophenone, which can then be alkylated with an alkylating agent having one to eight carbon atoms in the alkyl groups. The alkylation may be carried out in solution or suspension in aqueous alkali by heating with, for example, a dialkyl sulphate, such as dimethyl sulphate, or an alkyl para-toluene sulphonate, or an alkyl halide. Preferably an equimolar quantity of the two reactants or a slight excess of the alkylating agent is used. Examples are given of the preparation of 2 - hydroxy - 4 - methoxy - 41 methylbenzophenone from (1) para-toluyl chloride and resorcinol dimethyl ether, from (2) resorcinol, and para-toluyl chloride, using dimethyl sulphate as an alkylating agent; 2-hydroxy-4-ethoxy - 41 - methylbenzophenone from para-toluyl chloride and resorcinol diethyl ether. Other compounds mentioned are 2-hydroxy-4-methoxy - 41 - ethylbenzophenone, 2 - hydroxy-4 - ethoxy - 41 - ethylbenzophenone and 2 - hydroxy - 4 - n - butoxy - 41 - n - butylbenzophenone. Specification 789,070 is referred to.ALSO:The invention comprises 2-hydroxy-4-alkoxy-41-alkylbenzophenones in which the alkyl and alkoxy groups each contain up to eight carbon atoms for use as absorbers of ultra-violet light. Examples of these compounds are 2-hydroxy-4 - methoxy - 41 - methyl - benzophenone, 2 - hydroxy - 4 - methoxy - 41 - ethylbenzophenone, 2 - hydroxy - 4 - ethoxy - 41 - methylbenzophenone, 2 - hydroxy - 4 - ethoxy - 41 - ethylbenzophenone and 2 - hydroxy - 4 - n - butoxy41 - n - butylbenzophenone. Compositions resistant to the action of ultra-violet light comprise an organic polymeric material and at least one of the above defined compounds. The preferred polymeric materials are cellulose esters and ethers, homopolymers and copolymers of compounds containing a vinyl or vinylidene group such as styrene, vinyl chloride, vinyl acetate, vinyl butyrate, vinylidene chloride, alkyl esters of acrylic and methacrylic acids and compounds obtained by copolymerization of ethylenically unsaturated compounds containing a plurality of ester groups and compounds containing a vinyl group. Suitable amounts of 2 - hydroxy - 4 - alkoxy - 41 - alkylbenzophenones incorporated in the compositions are 0.05 to 0.5% of the weight of polymeric material, although amounts of 0.01 to 10% may be used. The benzophenones may be incorporated into cellulose esters or ethers together with plasticizers. The selected benzophenone may first be dissolved or dispersed in part or the whole of the plasticizer, which may then be incorporated with the ester or ether. Alternatively the benzophenone may be dissolved directly in whole or part of the cellulose derivative. Compositions of the benzophenones with vinyl polymers may be prepared by incorporating the benzophenone into the vinyl polymers during their formation. A free radical generating catalyst may be present. Examples are given of a composition of (1) polymerized methyl methacrylate or butyl methacrylate and 2 - hydroxy - 4 - methoxy - 41 - methylbenzophenone; (2) nitrocellulose lacquer and 2-hydroxy - 4 - methoxy - 41 - methylbenzophenone. Specification 789,070 is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB592456A GB823544A (en) | 1956-02-24 | 1956-02-24 | 2-hydroxy-4-alkoxy-4-alkylbenzophenones and compositions containing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB592456A GB823544A (en) | 1956-02-24 | 1956-02-24 | 2-hydroxy-4-alkoxy-4-alkylbenzophenones and compositions containing the same |
Publications (1)
Publication Number | Publication Date |
---|---|
GB823544A true GB823544A (en) | 1959-11-11 |
Family
ID=9805190
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB592456A Expired GB823544A (en) | 1956-02-24 | 1956-02-24 | 2-hydroxy-4-alkoxy-4-alkylbenzophenones and compositions containing the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB823544A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0371255A1 (en) * | 1988-11-02 | 1990-06-06 | BASF Aktiengesellschaft | Process for the preparation of 2-hydroxy-4-alkoxy-benzophenones |
CN115300493A (en) * | 2022-07-12 | 2022-11-08 | 厦门大学 | Application of nuclear receptor RXR alpha ligand and antitumor drug |
-
1956
- 1956-02-24 GB GB592456A patent/GB823544A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0371255A1 (en) * | 1988-11-02 | 1990-06-06 | BASF Aktiengesellschaft | Process for the preparation of 2-hydroxy-4-alkoxy-benzophenones |
CN115300493A (en) * | 2022-07-12 | 2022-11-08 | 厦门大学 | Application of nuclear receptor RXR alpha ligand and antitumor drug |
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