Process of making β-hydroxyamino compounds

• US 8,748,646 B2
• Filed: 06/20/2012
• Issued: 06/10/2014
• Est. Priority Date: 06/20/2011
• Status: Active Grant

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Kluesener, Bernard William, Shumate, Robert Edward, Panandiker, Rajan Keshav, Yelm, Kenneth Edward
• Primary Examiner(s): Davis, Brian J
• Application Number:
  US13/528,114
• Publication Number:
  US 20120323032A1
• Time in Patent Office: 720 Days
• Field of Search: 556/425
• US Class Current: 556/425
• CPC Class Codes: A61K 2800/10 General cosmetic use
• CPC Class Codes: A61K 8/898 containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: C07C 213/04 by reaction of ammonia or amines with olefin oxides or halohydrins
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C11D 3/3742 Nitrogen containing silicones

Abstract

The present application relates to molecules comprising one or more beta-hydroxyamine moieties, for example, aminosilicones and compositions such as consumer products comprising such molecules, as well as processes for making and using such molecules and such compositions. The aforementioned process is safer, more efficient and thus more economical. Thus, the aforementioned moleculers may be more widely used.

Claims

1. A process of making one or more molecules comprising one or more beta-hydroxyamine moieties said process comprising:

a) combining one or more molecules comprising one or more primary and/or secondary amine moieties, said one or more molecules comprising an amino silicone, with one or more molecules comprising one or more epoxide moieties and a catalyst comprising a protic solvent, said protic solvent;

(i) having a hydroxyl equivalents of at least 0.007 equivalents per gram; and

(ii) comprising at least two hydroxyl moieties per protic solvent molecule, and solubility of at least 0.2% by weight of protic solvent in the mixture at the conditions of the reaction, to form a first mixture;

b) heating said first mixture to a temperature of from about 20°

C. to about 200°

C., and maintaining said temperature for a time of from about 10 seconds to about 48 hours, to form a composition comprising one or more molecules comprising one or more beta-hydroxyamine moieties; and

c) optionally purifying said composition comprising one or more molecules comprising one or more beta-hydroxyamine moieties.

2. The process of claim 1 wherein said protic solvent'"'"'s at least two hydroxyl moieties per protic solvent molecule, have at least one conformation selected from the group consisting of α

-β

, α

-γ

, and α

-δ

.

3. The process of claim 1 wherein said protic solvent'"'"'s at least two hydroxyl moieties per protic solvent molecule, have at least one conformation that is α

-β

.

4. The process of claim 1 wherein said protic solvent comprises two or three hydroxyl moieties per protic solvent molecule.

5. The process of claim 1 wherein said protic solvent has a flash point of at least 50°

C.

6. The process of claim 1 wherein said composition comprising one or more molecules comprising one or more beta-hydroxyamine moieties comprises an organomodified silicone comprising one or more beta-hydroxyamine moieties.

7. The process of claim 1 wherein said protic solvent is selected from the group consisting of diols, triols, polyols and mixtures thereof.

8. The process of claim 7 wherein the said diol is selected from the group consisting of ethylene glycol, 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 2,2-dibutyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2-methylene-1,3-propanediol, 3-ethoxy-1,2-propanediol, 2-methyl-2-propyl-1,3-propanediol, 3-methoxy-1,2-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,2-pentanediol, 1,4-pentanediol, 1,5-pentanediol, 2,4-pentanediol, 1,2-hexanediol, neopentyl glycol, 1,5-hexanediol, 1,6-hexanediol, 2,5-hexanediol, 1,7-heptanediol, 1,4-heptanediol, 2-hydroxymethyl-1,3-propanediol, 1,2-octanediol, 1,8-octanediol, 4,5-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,2-decanediol, 1,2-dodecanediol, 1,12-dodecanediol, 1,14-tetradecanediol, 1,2-tetradecanediol, 1,16-hexadecanediol, 1,2-hexadecanediol, 1,2-octadecanediol, 1,18-octadecanediol, and glycerol monoethers and mixtures thereof.

9. The process of claim 8 wherein the said glycerol monoethers are selected from the group consisting of 3-propoxypropane-1,2-diol, batyl alcohol and mixtures thereof.

10. The process of claim 7 wherein the said triol is selected from the group consisting of glycerol, ethoxylated glycerol, propoxylated glycerol, alkoxyated glycerol, 1,1,1-tris(hydroxymethyl)ethane, 1,1,1-tris(hydroxymethyl)propane, 2-hydroxymethyl-1,3-propanediol, 1,2,4-butanetriol, 1,2,4-butanetriol, 3-methyl-1,3,5-pentanetriol, 1,2,3-hexanetriol, 1,2,6-hexanetriol, 1,2,3-heptanetriol, 1,2,3-octanetriol and mixtures thereof.

11. The process of claim 7 wherein the said polyol is selected from the group consisting of pentaerythritol, alkoxylated pentaerythritol, sorbitol, alkoxylated sorbitol, glucose, alkoxylated glucose, fructose, alkoxylated fructoses, and mixtures thereof.

12. The process of claim 11 wherein the said:

a) alkoxylated pentaerythritol is selected from the group consisting of ethoxylated pentaerythritol, proxylated pentaerythritol, and mixtures thereof;

b) alkoxylated sorbitol is selected from the group consisting of ethoxylated sorbitol, proxylated sorbitol and mixtures thereof;

c) alkoxylated glucose is selected from the group consisting of ethoxylated glucose, proxylated glucose, and mixtures thereof;

d) alkoxylated fructose is selected from the group consisting of ethoxylated fructose, proxylated fructose and mixtures thereof.

13. The process of claim 7 wherein the said polyol is selected from the group consisting of a sugar, a carbohydrate, an alkoxylated sugar, an alkoxylated carbohydrate and mixtures thereof.

14. The process of claim 1 wherein said amino silicone is selected from the group consisting of an aminopropylmethylsiloxane-dimethylsiloxane copolymer, aminoethylaminopropylmethylsiloxane-dimethylsiloxane copolymer, aminoethylaminopropyl terminated polydimethylsiloxane, aminopropyl terminated polydimethylsiloxane and mixtures thereof.

15. A process of making one or more molecules comprising one or more beta-hydroxyamine moieties said process comprising:

a) combining one or more molecules comprising one or more primary and/or secondary amine moieties, said one or more molecules comprising an amino silicone, with one or more molecules comprising one or more epoxide moieties and a catalyst comprising a protic solvent, said protic solvent being selected from the group consisting of diols, a water/diol mixture, triols, a water/triol mixture, polyols, a water/polyol mixture, a water/surfactant mixture and mixtures thereof;

b) heating said first mixture to a temperature of from about 20°

C. to about 200°

C., and maintaining said temperature for a time of from about 10 seconds to about 48 hours, to form a composition comprising one or more molecules comprising one or more beta-hydroxyamine moieties; and

c) optionally purifying said composition comprising one or more molecules comprising one or more beta-hydroxyamine moieties.