NOVEL LINEAR POLYDIMETHYLSILOXANE-POLYETHER COPOLYMERS HAVING AMINO AND/OR QUATERNARY AMMONIUM GROUPS AND USE THEREOF

• US 20120308494A1
• Filed: 12/29/2010
• Published: 12/06/2012
• Est. Priority Date: 01/29/2010
• Status: Active Grant

• Current Assignee: Evonik Degussa GmbH
• Original Assignee: Evonik Degussa GmbH
• Inventors: Schubert, Frank, Knott, Wilfried, Ferenz, Michael, Klein, Klaus-Dieter, Maurer, Tobias, Panandiker, Rajan Keshav, Scheurmann, Ralph, Kluesener, Bernhard William
• Granted Patent: US 8,957,009 B2
• Time in Patent Office: Days
• US Class Current: 424/59
• CPC Class Codes: A61K 8/898 containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• 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 77/388 containing nitrogen
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: D06M 15/6436 containing amino groups
• CPC Class Codes: D06M 15/647 containing polyether sequences

Abstract

Linear polydimethylsiloxane-polyether copolymers with amino and/or quaternary ammonium groups, obtainable by the reaction of organopolysiloxanes functionalized with secondary aminoalkyl groups with the reaction products formed from compounds containing epoxy groups and amines, the use thereof and process for preparation thereof.

Claims

1. A linear polydimethylsiloxane-polyether copolymer with an amino group and/or a quaternary ammonium group, obtained by:

reacting an organopolysiloxane functionalized with a secondary aminoalkyl group with a reaction product formed from compounds containing epoxy groups and amines.

10. The linear polydimethylsiloxane-polyether copolymer according to claim 1:

wherein the linear polydimethylsiloxane-polyether copolymer is of the formula (4);

H-A—

[(B−

C)_x−

B-A]_y—

H 

 

Formula (4);

where A is a siloxane fragment according to formula (5);

11. The linear polydimethylsiloxane-polyether copolymer according to claim 10, and derivatives thereof;

wherein the linear polydimethylsiloxane-polyether copolymer has been quaternized with acids and/or alkylating agents and bears an ammonium group.

12. A composition comprising:

the linear polydimethylsiloxane-polyether copolymer according to claim 1.

13. A method of permanently softening a fabric, comprising:

utilizing the process of claim 2 to obtain a linear polydimethylsiloxane-polyether copolymer according to claim 1;

utilizing the linear polydimethylsiloxane-polyether copolymer as a permanent softener for a fabric selected from the group consisting of wovens, textile wovens, knits, nonwovens, tissue, paper fiber, fibers of natural and/or synthetic raw materials, leather, hair, and hide.

14. The method according to claim 13;

wherein the softener imparts hydrophilic properties to the fabric treated therewith.

15. A method of making a formulation for applying to hair, comprising:

utilizing the process of claim 2 to obtain the linear polydimethylsiloxane-polyether copolymer according to claim 1;

utilizing the linear polydimethylsiloxane-polyether copolymer to make the formulation;

wherein;

the formulation improves combability, softness, volume, shapeability, manageability, and disentangleability of undamaged and damaged hair after the formulation is applied to the hair as compared to before the formulation is applied to the hair; and

/or

the formulation imparts shine to the hair after the formulation is applied to the hair as compared to before the formulation is applied to the hair.

16. The method according to claim 15;

wherein the linear polydimethylsiloxane-polyether copolymer obtained by utilizing the process of claim 2 is the linear polydimethylsiloxane-polyether copolymer according to claim 10;

wherein the formulation is a shine improving cosmetic formulation selected from the groups consisting of hair treatment compositions and hair aftertreatment compositions to be rinsed out of or to remain in the hair, conditioners, 2 in 1 shampoos, rinses, hair repair treatments, hair masks, styling aids, styling compositions, hair drying lotions, hair-setting compositions, permanent wave compositions, hair smoothing compositions, and compositions for dyeing the hair.

17. A method comprising:

forming a mixture comprising;

the linear polydimethylsiloxane-polyether copolymer according to claim 10; and

at least one additional component selected from the group consisting of emollients, emulsifiers and surfactants, thickeners/viscosity regulators/stabilizers, UV light protection filters, antioxidants, hydrotropes and polyols, solids and fillers, film formers, pearlescent additives, active deodorant and antiperspirant ingredients, insect repellents, self-tanning agents, preservatives, conditioners, perfumes, dyes, active cosmetic ingredients, care additives, superfatting agents, and solvents;

wherein the mixture is for at least one of a cosmetic formulation, a dermatological formulation, a pharmaceutical formulation, a cosmetic personal care composition, and body/skin cleaning compositions.

18. The method according to claim 17;

wherein the mixture is in the form of an aqueous surfactant formulation for achieving a pleasant, silky-smooth skinfeel.

2. A process for preparing a linear polydimethylsiloxane-polyether with an amino group and/or a quaternary ammonium group, comprising:

a) first reacting a diepoxide with at least one amine compound to give a chain-extended adduct bearing a terminal glycidyl group, the molar ratio of diepoxide to amine being variable but at least greater than 1;

1; and

b) the reacting this intermediate with a linear polysiloxane bearing a terminal secondary amino group;

c) optionally, completely or partially quaternizing the nitrogen atoms at any point in this process by adding acids or alkylating reagents; and

d) also optionally, adding water or organic compounds selected from the group of polyethers, polyols, and alcohols, as diluents, emulsifiers, or modifiers.

3. The process according to claim 2:

wherein the diepoxide used is a compound of the formula (1);

4. The process according to claim 3:

wherein Y is a divalent polyether radical of the type;

—

(CH₂—

CHR²—

O)_m—

CH₂—

CHR²—

;

where m is an integer from 0 to 50; and

where R² is hydrogen or an alkyl group having 1-4 carbon atoms.

5. The process according to claim 2:

wherein the amine compound used in process step (a) is a di-secondary amine of the formula (2);

6. The process according to claim 5;

wherein the compound of the formula (2) is a cyclic amine where;

p is 1 or a linear diamine;

or

the two nitrogen atoms are constituents of a heterocyclic fragment.

7. The process according to claim 6;

wherein the compound of the formula (2) used is at least one of piperazine, N,N′

-dimethylhexamethylene-1,6-diamine, and N,N′

-dimethyltetramethylene-1,4-diamine.

8. The process according to claim 2:

wherein the linear polysiloxane used in reaction step (b) has a terminal secondary amino group and is of the formula (3);

9. The process according to claim 2:

wherein an acid or an alkylating reagent is added in process step (c).