Skin care cosmetic methods of sebum control using carboxyalkylates of branched alcohols and/or alkoxylates thereof

A cosmetic method of providing a skin benefit, the method comprising applying to the skin a compound of the formula A:

• R—O-M (A)
• wherein:
• R is a branched alkyl or alkenyl chain having at least 7 carbon atoms, and
• at least two branches;
• O is an oxygen atom;
• and
• M is (—(CH2)pO)n—(CH2)mCO2X), where n is 0 or an integer between 1 and 7,
• m is an integer between 2 and 4, p is an integer between 2 and 4;
• and
• X is hydrogen, a methyl group, an ethyl group, or a cation;
• said benefit selected from the group consisting of:
• (a) reducing or preventing oily skin conditions;
• (b) reducing or preventing sebum secretion from sebocytes;
• (c) stimulating collagen synthesis by fibroblasts in the skin;
• and
• (d) controlling microbial activity of bacteria associated with acne.

A process of synthesizing a compound of the formula A:

• R—O-M (A)
• wherein:
• R is a branched alkyl or alkenyl chain having at least 7 carbon atoms, and at least two branches;
• O is an oxygen atom;
• M is (—(CH2)pO)n—(CH2)mCO2X), where n is 0 or an integer between 1 and 7,
• m is an integer between 2 and 4, p is an integer between 2 and 4;
• comprising:
• (a) combining a branched alcohol with acrylonitrile to form alkyl or alkenyl oxypropionitrile;
• (b) reacting said alkyl or alkenyl oxypropionitrile nitrile with aqueous solution of acid to form carboxyethyl iso-alcohol.

A process of synthesizing a compound of the formula A:

• R—O-M (A)
• wherein:
• R is a branched alkyl or alkenyl chain having at least 7 carbon atoms, and at least two branches;
• O is an oxygen atom;
• M is (—(CH2)pO)n—(CH2)mCO2X), where n is 0 or an integer between 1 and 7,
• m is an integer between 2 and 4, p is an integer between 2 and 4;
• comprising:
• (a) combining a branched alcohol with a compound selected from the group consisting of chloroacetic acid, chloropripionic acid, chlorobutyric acid, and mixtures thereof to form a heterogeneous reaction mixture;
• (b) stirring and heating said heterogeneous reaction mixture at slight reflux under nitrogen;
• (c) cooling to room temperature;
• (d) filtering and washing to form a paste;
• (e) dissolving said paste in water;
• (f) acidifying said dissolved paste with HCl;
• (g) extracting said acidified paste with chloroform or hexane;
• (h) removal of chloroform to form said compound of formula A.