Method of making siloxane-based polyamide elastomers

• US 6,838,541 B2
• Filed: 02/12/2003
• Issued: 01/04/2005
• Est. Priority Date: 02/12/2003
• Status: Expired due to Term

• Current Assignee: Dow Silicones Corporation (Dow, Inc.)
• Original Assignee: Dow, Inc.
• Inventors: Nguyen, Kimmai Thi, Lin, Zuchen, Petroff, Lenin James
• Primary Examiner(s): Moore, Margaret G.
• Application Number:
  US10/365,851
• Publication Number:
  US 20040156807A1
• Time in Patent Office: 692 Days
• Field of Search: 528/15, 528/26
• US Class Current: 528/28
• CPC Class Codes: A61K 8/898 containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• CPC Class Codes: A61Q 15/00 Anti-perspirants or body deodorants deodorisation of air A61L9/00
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 5/00 Preparations for care of the hair
• CPC Class Codes: C08G 77/455 containing polyamide, polyesteramide or polyimide sequences

Abstract

Siloxane-based polyamide elastomers can be prepared by heating a reaction mixture containing an olefinic acid and an organic amine to form an organic amide, and reacting the organic amide with a hydride functional polyorganosiloxane in the presence of a hydrosilylation catalyst to form the siloxane-based polyamide elastomer. The hydride functional polyorganosiloxane contains at least one pendant hydrogen. The elastomers are useful additives in personal care products and can be applied to the hair, the skin, or the underarm. They can also be used to modify thermoplastic nylons, and for treating woven and non-woven textiles, such as air bags, carpeting, and apparel.

Claims

1. A method of making a siloxane-based polyamide elastomer comprising heating and reacting an organic amide with a hydride functional polyorganosiloxane in the presence of a hydrosilylation catalyst to form the siloxane-based polyamide elastomer;

the hydride functional polyorganosiloxane being a polymer or copolymer having a formula selected from the group consisting of

wherein R1 represents (i) an alkyl group containing 1-20 carbon atoms;

(ii) an aryl group;

(iii) an alkaryl group;

or (iv) an aralkyl group; and

(v) n and m each have a value of 1-1,000.

2. A method according to claim 1 in which the organic amide is a diamide prepared from an organic diamine selected from the group consisting of hexamethylene diamine, ethylene diamine, and decamethylene diamine, and an olefinic acid.

3. A method according to claim 2 in which the olefinic acid is a compound selected from the group consisting of undecylenic acid, acrylic acid, 3-butenoic acid, and 4-pentenoic acid.

4. A siloxane-based polyamide elastomer prepared according to the method defined in claim 2.

5. A product containing the siloxane-based polyamide elastomer of claim 4 in which the product is selected from the group consisting of antiperspirants, deodorants, skin creams, skin care lotions, moisturizers, facial treatments, acne removers, wrinkle removers, personal cleansers, facial cleansers, bath oils, perfumes, colognes, sachets, sunscreens, pre-shave lotions, after-shave lotions, shaving soaps, shaving lathers, hair shampoos, hair conditioners, hair sprays, mousses, permanents, depilatories, cuticle coats, make-up, color cosmetics, foundations, blushes, lipsticks, eyeliners, mascara, oil removers, color cosmetic removers, bath powders, body powders, pharmaceuticals, biocides, herbicides, pesticides, biologically active substances, cellulosic substrates, synthetic nonwoven substrates, wet-cleansing wipes tissues, and towels.

6. A method of treating hair, skin, or underarm, comprising applying to hair, skin, or underarm the siloxane-based polyamide elastomer of claim 4.

7. A method of modifying thermoplastic nylons comprising applying to the thermoplastic nylons the siloxane-based polyamide elastomer of claim 4.

8. A method of treating woven and non-woven textiles comprising applying to textiles the siloxane-based polyamide elastomer of claim 4.

9. A method of making a siloxane-based polyamide elastomer comprising heating and reacting (i) an organic amide with (ii) a hydride functional polyorganosiloxane, in the presence of (iii) a solvent, and (iv) a hydrosilylation catalyst, to form the siloxane-based polyamide elastomer;

the hydride functional polyorganosiloxane being a polymer or copolymer having a formula selected from the group consisting of

wherein R1 represents (i) an alkyl group containing 1-20 carbon atoms;

(ii) an aryl group;

(iii) an alkaryl group;

or (iv) an aralkyl group; and

(v) n and m each have a value of 1-1,000.

10. A method according to claim 9 in which the organic amide is a diamide prepared from an organic diamine selected from the group consisting of hexamethylene diamine, ethylene diamine, and decamethylene diamine, and an olefinic acid.

11. A method according to claim 10 in which the olefinic acid is a compound selected from the group consisting of undecylenic acid, acrylic acid, 3-butenoic acid, and 4-pentenoic acid.

12. A siloxane-based polyamide elastomer prepared according to the method defined in claim 10.

13. A product containing the siloxane-based polyamide elastomer of claim 12 in which the product is selected from the group consisting of antiperspirants, deodorants, skin creams, care lotions, moisturizers, facial treatments, acne removers, wrinkle removers, personal cleansers, facial cleansers, bath oils, perfumes, colognes, sachets, sunscreens, pre-shave lotions, after-shave lotions, shaving soaps, shaving lathers, hair shampoos, hair conditioners, hair sprays, mousses, permanents, depilatories, cuticle coats, make-up, color cosmetics, foundations, blushes, lipsticks, eyeliners, mascara, oil removers, color cosmetic removers, bath powders, body powders, pharmaceuticals, biocides, herbicides, pesticides, biologically active substances, cellulosic substrates, synthetic nonwoven substrates, wet-cleansing wipes, tissues, and towels.

14. A method of treating hair, skin, or underarm, comprising applying to hair, skin, or underarm the siloxane-based polyamide elastomer of claim 12.

15. A method of modifying thermoplastic nylons comprising applying to the thermoplastic nylons the siloxane-based polyamide elastomer of claim 12.

16. A method of treating woven and non-woven textiles comprising applying to the textiles the siloxane-based polyamide elastomer of claim 12.