# US 10,245,451 B2 · Aminofunctional organosiloxanes

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- Number: US 10,245,451 B2
- Document ID: US10245451B2
- Status: Granted
- Kind: B2
- Application number: 15/823,001
- Filed: 2017-11-27
- Published: 2018-03-22
- Granted: 2019-04-02
- Earliest claimed: 2011-11-29
- Assignees: Dow Silicones Corporation
- Applicants: Dow Corning Corporation
- Inventors: Sylvie Bouzeloc; Severine Cauvin; Cindy Delvalle; Tatiana Dimitrova; Sophie Hanssens; Lok Ming Eva Li; Elodie Raynaud; Houria Seghir; Avril E. Surgenor; Blondine Donatienne Van Roy
- Web page: https://patentgrep.com/patent/US10245451B2

## CPC

- C08G 77/26: nitrogen-containing groups
- A61K 8/39: Derivatives containing from 2 to 10 oxyalkylene groups
- A61K 8/416: {Quaternary ammonium compounds (A61K8/35 takes precedence)}
- A61K 8/585: {Organosilicon compounds}
- A61K 8/86: Polyethers
- A61K 8/898: containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
- A61Q 5/00: Preparations for care of the hair
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 5/12: Preparations containing hair conditioners
- C08J 3/05: from solid polymers
- C08L 83/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08J 2383/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Aminofunctional silicone compositions are disclosed comprising: an organopolysiloxane having an average formula of (CH3)3SiO[(CH3)2SiO]x [(CH3)RNSiO]ySi(CH3)3 with less than 1 weight % of nitrogen in its formula, where RN is an aminofunctional group, x is ≥100, y is ≥1 with the proviso the sum of x+y is from 250 to 350; wherein the viscosity of the silicone composition ranges from 1000 to 2500 cP at 25° C. and is measured by a Brookfield RV DV viscometer equipped with Pro CP 52 spindle at 20 RPM; and the aminofunctional silicone composition contains less than 0.1 weight % of D4 and less than 0.1 weight % D5 cyclic siloxanes.

## Claims

### Claim 1

A method of treating a surface of a fiber, the method comprising applying an aqueous emulsion to the surface of the fiber, wherein the aqueous emulsion comprises:
A) an aminofunctional silicone composition comprising an organopolysiloxane having an average formula:
(CH3)3SiO[(CH3)2SiO]x[(CH3)RNSiO]ySi(CH3)3
with less than 1 weight % of nitrogen in its formula,
where RN is an aminofunctional group, x is ≥100, and y is ≥1, with the proviso that the sum of x+y is from 250 to 350; and
B) a quaternary ammonium surfactant having a formula:
R1R2R3R4N+X−,
where R1 is a radical containing at least 10 carbon atoms, R2 is R1 or a hydrocarbyl containing 1 to 12 carbon atoms, R3 is R1, R2, or an alcohol group containing 2 to 10 carbon atoms, R4 is R1, R2, or R3, and X− is a halide, sulfate, sulfonate, methosulfate, or ethosulfate;
wherein the viscosity of A) the aminofunctional silicone composition ranges from 1000 to 2500 cP at 25° C. as measured by a Brookfield RV DV viscometer equipped with Pro CP 52 spindle at 20 RPM;
wherein A) the aminofunctional silicone composition contains less than 0.1 weight % of octamethylcyclotetrasiloxanes (D4) and less than 0.1 weight % decamethylcyclopentasiloxanes (D5) cyclic siloxanes; and
wherein B) the quaternary ammonium surfactant is present in the aqueous emulsion in an amount of at least 0.5 weight %.

### Claim 2 (depends on 1)

The method of claim 1, wherein the aminofunctional group RN has the formula —CH2CH2CH2NHCH2CH2NH2.

### Claim 3 (depends on 1)

The method of claim 1, wherein A) the aminofunctional silicone composition is present in the aqueous emulsion in an amount of from 15 to 80 weight %.

### Claim 4 (depends on 1)

The method of claim 1, wherein B) the quaternary ammonium surfactant is present in the aqueous emulsion in an amount of from 0.5 to 10 weight %.

### Claim 5 (depends on 1)

The method of claim 1, wherein the aqueous emulsion further comprises:
C) a nonionic surfactant.

### Claim 6 (depends on 5)

The method of claim 5, wherein C) the nonionic surfactant is present in the aqueous emulsion in an amount of from 2 to 8 weight %.

### Claim 7 (depends on 1)

The method of claim 1, wherein:
i) the fiber is selected from the group of natural fibers, regenerated fibers, synthetic fibers, and combinations thereof; and/or
ii) the fiber is selected from the group of textiles, threads, filaments, tows, yarns, woven fabrics, knitted materials, non-woven materials, paper, carpet, leather, and combinations thereof.

### Claim 8 (depends on 1)

The method of claim 1, further comprising the step of drying the surface of the fiber after application of the aqueous emulsion.

### Claim 9 (depends on 1)

The method of claim 1, wherein the aqueous emulsion is applied in an amount to provide 0.1 to 15 weight % of the aqueous emulsion on the fiber based on dry weight of the fiber.