IP Library Granted Patent US 11,083,682
Granted Patent B2
US 11,083,682 · App. 16/048,432 · Granted Aug 10, 2021

Composition and method for improving and protecting keratins

Inventors: Joseph I. Kravitz (Omaha, NE); Sara M. Dreamer (Omaha, NE); Angelia J. Francis (Omaha, NE); Steve M. Hudson (Omaha, NE); Thomas D. Boatright (Council Bluffs, IA)
A61K8/602A61K8/86A61Q5/002A61Q5/04A61Q5/08A61Q5/10A61K2800/591A61K2800/884
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Quick Facts
Patent No.
US 11,083,682
App. No.
16/048,432
Granted
Aug 10, 2021
Kind
B2
Abstract

The present invention relates in general to keratin treatment compositions and methods, and more specifically, compositions comprising up to 60% olefinic compounds and at least one unactivated double bond, the composition comprising fatty acid esters of polyhydric alcohols. The present invention is configured to be easily incorporated into bleaching processes, coloring processes, perming processes, shampoos, conditioners and/or styling products. The purpose of the invention is to provide a composition and method that will improve the overall health of keratins, in particular, texture, body, shine and strength.

Claims (81)

1. A method for improving and protecting keratins, the method comprising:

providing keratins, the keratins comprising at least one thiol group;

providing a keratin treatment composition, comprising:

a) 0.1-5% by weight olefinic compounds comprising unsaturated fatty acid esters of polyhydric alcohols, wherein the unsaturated fatty acid esters of polyhydric alcohols is selected from the group consisting of the structures:

b) 0.1-60% by weight olefinic compounds comprising:

i. unsaturated fatty acid amides of the formula R 1 —C(O)—NR2R 3 , wherein R 1 is a C 9 -C 22 fatty acid radical having at least one isolated double bond, and wherein R 2 and/or R 3 is H or a C 1 -C 4 alkyl or a C 1 -C 4 hydroxyalkyl or higher alkoxylated analogs;

ii. quaternized unsaturated fatty acid amides, having the

structure:

wherein R=unsaturated fatty acid or fatty acid fraction derived from whole-oil rich in unsaturated fatty acid;

iii. fatty acid esters of monohydric alcohols of the formula R 1 —C(O)—OR 2 , wherein R 1 is a C 9 -C 22 fatty acid radical having at least one isolated double bond, and wherein R 2 is a C 2 -C 22 alcohol; and

iv. mixtures thereof;

c) the olefinic compounds comprising at least one unactivated double bond;

d) the at least one unactivated double bond consisting of a covalent bond; and

e) the keratin treatment composition does not comprise a Michael acceptor;

providing a chemical oxidative treatment;

applying the chemical oxidative treatment to the keratins;

generating thiyl radicals in the keratin via the chemical oxidative treatment;

applying the keratin treatment composition to the keratins;

creating a thiol-ene reaction between the thiyl radicals in the keratin and the at least one unactivated double bond of the olefinic compounds;

modifying the at least one thiol group in the keratins through the thiol-ene reaction; and

forming a carbon-sulfur bond between the keratins and the at least one unactivated double bond of the olefinic compounds;

wherein the formation of the carbon-sulfur bond between the keratins and the at least one unactivated double bond of the olefinic compounds provides permanent conditioning to improve the overall health of the keratins.

2. The method for improving and protecting keratins of claim 1 , wherein the keratins are hair, nails, skin and/or combinations thereof.

3. The method for improving and protecting keratins of claim 2 , wherein the overall health of the keratins comprises texture, body, shine and strength.

4. The method for improving and protecting keratins of claim 3 , wherein the chemical oxidative treatment comprises hair bleaching.

5. The method for improving and protecting keratins of claim 3 , wherein the chemical oxidative treatment comprises hair coloring.

6. The method for improving and protecting keratins of claim 3 , wherein the chemical oxidative treatment comprises a neutralization step in hair perming.

7. The method for improving and protecting keratins of claim 3 , wherein the keratin treatment composition is incorporated as an additive into the chemical oxidative treatment.

8. The method for improving and protecting keratins of claim 3 , further comprising sealing cuticles of the keratins via the chemical oxidative treatment and the keratin treatment composition to protect the keratins.

9. The method for improving and protecting keratins of claim 3 , wherein the at least one unactivated double bond is 2-4 unactivated double bonds, the 2-4 unactivated double bonds consisting of covalent bonds.

10. A method for improving and protecting keratins, the method comprising:

providing keratins, the keratins comprising at least one thiol group;

providing a keratin treatment composition, comprising:

a) 0.1-5% by weight olefinic compounds comprising unsaturated fatty acid esters of polyhydric alcohols, wherein the unsaturated fatty acid esters of polyhydric alcohols is selected from the group consisting of the structures:

b) 0.1-60% by weight olefinic compounds comprising:

i. unsaturated fatty acid amides of the formula R 1 —C(O)—NR 2 R 3 , wherein R 1 is a C 9 C 22 fatty acid radical having at least one isolated double bond, and wherein R 2 and/or R 3 is H or a C 1 -C 4 alkyl or a C 1 -C 4 hydroxyalkyl or higher alkoxylated analogs;

ii. quaternized unsaturated fatty acid amides, having the

structure:

wherein R=unsaturated fatty acid or fatty acid fraction derived from whole-oil rich in unsaturated fatty acid;

iii. fatty acid esters of monohydric alcohols of the formula R 1 —C(O)—OR 2 , wherein R 1 is a C 9 -C 22 fatty acid radical having at least one isolated double bond, and wherein R 2 is a C 2 -C 22 alcohol; and

iv. mixtures thereof;

b) the olefinic compounds comprising a plurality of unactivated double bonds;

c) the plurality of unactivated double bonds consisting of covalent bonds; and

e) the keratin treatment composition does not comprise a Michael acceptor;

providing a latent oxidative treatment;

applying the latent oxidative treatment to the keratins;

generating thiyl radicals in the keratin via the latent oxidative treatment;

applying the keratin treatment composition to the keratins;

creating a thiol-ene reaction between the thiyl radicals in the keratin and the plurality of unactivated double bonds of the olefinic compounds;

modifying the at least one thiol group in the keratins through the thiol-ene reaction; and

forming a carbon-sulfur bond between the keratins and the plurality of unactivated double bonds of the olefinic compounds;

wherein the formation of the carbon-sulfur bond between the keratins and the plurality of unactivated double bonds of the olefinic compounds provides permanent conditioning to improve the overall health of the keratins.

11. The method for improving and protecting keratins of claim 10 , wherein the keratins are hair, nails, skin and/or combinations thereof.

12. The method for improving and protecting keratins of claim 11 , wherein the overall health of the keratins comprises texture, body, shine and strength.

13. The method for improving and protecting keratins of claim 12 , wherein the latent oxidative treatment comprises shampoos, conditioners and/or styling products.

14. The method for improving and protecting keratins of claim 13 , wherein the plurality of unactivated double bonds is 2-4 unactivated double bonds, the 2-4 unactivated double bonds consisting of covalent bonds.

15. A method for improving and protecting keratins, the method comprising:

providing keratins, the keratins comprising at least one thiol group;

providing a keratin treatment composition, comprising:

a) 0.1-5% by weight olefinic compounds selected from the group consisting of the structures:

b) 0.1-60% by weight olefinic compounds selected from the group consisting of:

i. unsaturated fatty acid amides of the formula R 1 —C(O)—NR 2 R 3 , wherein R 1 is a C 9 -C 22 fatty acid radical having at least one isolated double bond, and wherein R 2 and/or R 3 is H or a C 1 -C 4 alkyl or a C 1 -C 4 hydroxyalkyl or higher alkoxylated analogs;

ii. quaternized unsaturated fatty acid amides, having the

structure:

wherein R=unsaturated fatty acid or fatty acid fraction derived from whole-oil rich in unsaturated fatty acid;

iii. fatty acid esters of monohydric alcohols of the formula R 1 —C(O)—OR 2 , wherein R 1 is a C 9 -C 22 fatty acid radical having at least one isolated double bond, and wherein R 2 is a C 2 -C 22 alcohol; and

iv. mixtures thereof;

c) the olefinic compounds comprising 2-4 unactivated double bonds;

d) the 2-4 unactivated double bonds consisting of covalent bonds; and

e) the keratin treatment composition does not comprise a Michael acceptor;

providing an oxidative treatment;

applying the oxidative treatment to the keratins;

generating thiyl radicals in the keratin via the oxidative treatment;

applying the keratin treatment composition to the keratins;

creating a thiol-ene reaction between the thiyl radicals in the keratin and the 2-4 unactivated double bonds of the olefinic compounds;

modifying the at least one thiol group in the keratins through the thiol-ene reaction; and

forming a carbon-sulfur bond between the keratins and the 2-4 unactivated double bonds of the olefinic compounds;

wherein the formation of the carbon-sulfur bond between the keratins and the 2-4 unactivated double bonds of the olefinic compounds provides permanent conditioning to improve the overall health of the keratins.

16. The method for improving and protecting keratins of claim 15 , wherein the oxidative treatment is a chemical oxidative treatment comprising hair bleaching, hair coloring, a neutralization step in hair perming, and/or combinations thereof.

17. The method for improving and protecting keratins of claim 16 , wherein the keratin treatment composition is incorporated as an additive into the chemical oxidative treatment.

18. The method for improving and protecting keratins of claim 15 , wherein the oxidative treatment is a latent oxidative treatment comprising shampoos, conditioners and/or styling products.

Assignments (2)
CHANGE OF NAME Recorded Mar 5, 2025
From: MARIANNA INDUSTRIES, INC.
To: COHERE BEAUTY, OMAHA, INC.
Reel/Frame 070418/0978 →
SECURITY INTEREST Recorded May 21, 2021
From: MARIANNA INDUSTRIES, INC.
To: MONROE CAPITAL MANAGEMENT ADVISORS, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 056310/0722 →
Continuity (3)
Division 15282956 · Sep 30, 2016
Provisional Application 62284449 · Sep 30, 2015
Related Publication 20180333343A1 · Nov 22, 2018