IP Library Granted Patent US 8,778,319
Granted Patent B2
US 8,778,319 · App. 13/522,560 · Granted Jul 15, 2014

Polysiloxanes having quaternary ammonium groups, method for producing same and use thereof in formulations for cleansing and care

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Quick Facts
Patent No.
US 8,778,319
App. No.
13/522,560
Granted
Jul 15, 2014
Kind
B2
Abstract

The invention relates to novel polysiloxanes having quaternary ammonium groups, and to a method for producing same. The invention further relates to the use of said polymers as an active care ingredient in formulations for the care and cleansing of skin and skin appendages, for example, as conditioning agents for hair.

Claims (99)

1. A polysiloxane comprising at least one quaternary ammonium group and of the formula (I)

M a M′ a1 M″ a2 M′″ a3 D b D′ b1 D″ b2 D′″ b3 T c T′ c1 Q d   formula (I),

wherein

M=(R 1 3 SiO 1/2 )

M′=(R 2 R 1 2 SiO 1/2 )

M″=(R 3 R 1 2 SiO 1/2 )

M′″=(R 4 R 1 2 SiO 1/2 )

D=(R 1 2 SiO 2/2 )

D′=(R 2 R 1 SiO 2/2 )

D″=(R 3 R 1 SiO 2/2 )

D′″=(R 4 R 1 SiO 2/2 )

T=(R 5 SiO 3/2 )

T′=(R 2 SiO 3/2 )

Q=(SiO 4/2 )

a=0 to 32,

a1=0 to 10,

a2=0 to 32,

a3=0 to 10,

with the proviso that

a+a1+a2+a3>3,

b=1 to 600,

b1=0 to 10,

b2=0 to 80,

b3=0 to 20,

c=0 to 30,

c1=0 to 10,

d=0 to 15,

with the proviso that

a2+b2>1, and

c+c1+d>1,

each R 1 is, independently of one another, an identical or different linear or branched, hydrocarbon radical having 1 to 30 carbon atoms,

each R 2 is, independently of one another, an identical or different alkoxy or acyloxy radical,

each R 3 is, independently of one another, an identical or different organic radical which has a quaternary ammonium function,

each R 4 is, independently of one another, an identical or different organic epoxy radical, and

each R 5 is, independently of one another, an identical or different radical, R 1 , R 3 or R 4 .

2. The polysiloxane as claimed in claim 1 , wherein said R 4 radicals are identical or different radicals selected from the group consisting of:

3. The polysiloxane as claimed in claim 1 , wherein said R 3 groups are groups with the structure —R 6 —R 7 , wherein R 6 radicals are identical or different divalent radicals selected from the group consisting of

R 7 is selected from the group consisting of

each R 8 is an identical or different radical and comprises hydrogen or an alkyl having 1 to 6 C atoms;

each R 9 is an identical or different divalent hydrocarbon radical;

R 10 , R 11 , and R 12 are in each case independently of one another hydrogen or alkyl radicals having 1 to 30 C atoms, or radicals of formula

each R 13 is an identical or different radical and is

—O— or —NR 16 —;

each R 14 is an identical or different divalent hydrocarbon radical;

each R 15 is an identical or different alkyl, aryl or alkaryl radical having 1 to 30 C atoms;

each R 16 is an identical or different radical and is hydrogen or an alkyl having 1 to 6 C atoms;

m=2 to 18;

n=2 to 18,

o=0 to 30,

p=0 to 30,

A − are identical or different counterions to positive charges on the quaternized nitrogen groups, and are inorganic or organic anions of the acids HA, or derivatives thereof.

4. A process for preparing a polysiloxane comprising:

A) preparing an SiH-group-containing siloxane framework, branched via at least two units selected from T and Q units, by equilibration and condensation of a mixture comprising the components

a) at least one SiH-functional siloxane,

b) at least one SiH-function-free siloxane,

and either component c) or component d),

or both components c) and d), where

c) is at least one tetraalkoxysilane,

d) is at least one trialkoxysilane

with addition of water and at least one suitable catalyst,

B) hydrosilylating the SiH-functional siloxanes from process step A) with at least one unsaturated epoxide, and

C) quaternizing the epoxysiloxanes from process step B) with at least one tertiary amine, wherein steps a)-d) provide a polysiloxane comprising at least one quaternary ammonium group and of the formula (I)

M a M′ a1 M″ a2 M′″ a3 D b D′ b1 D″ b2 D′″ b3 T c T′ c1 Q d   formula (I),

wherein

M=(R 1 3 SiO 1/2 )

M′=(R 2 R 1 2 SiO 1/2 )

M″=(R 3 R 1 2 SiO 1/2 )

M′″=(R 4 R 1 2 SiO 1/2 )

D=(R 1 2 SiO 2/2 )

D′=(R 2 R 1 SiO 2/2 )

D″=(R 3 R 1 SiO 2/2 )

D′″=(R 4 R 1 SiO 2/2 )

T=(R 5 SiO 3/2 )

T′=(R 2 SiO 3/2 )

Q=(SiO 4/2 )

a=0 to 32,

a1=0 to 10,

a2=0 to 32,

a3=0 to 10,

with the proviso that

a+a1+a2+a3>3,

b=1 to 600,

b1=0 to 10,

b2=0 to 80,

b3=0 to 20,

c=0 to 30,

c1=0 to 10,

d=0 to 15,

with the proviso that

a2+b2>1, and

c+c1+d>1,

each R 1 is, independently of one another, an identical or different linear or branched hydrocarbon radical having 1 to 30 carbon atoms,

each R 2 is, independently of one another, an identical or different alkoxy or acyloxy radical,

each R 3 is, independently of one another, an identical or different organic radical which has a quaternary ammonium function,

each R 4 is, independently of one another, an identical or different organic epoxy radical, and

each R 5 is, independently of one another, an identical or different radical, R 1 , R 3 or R 4 .

5. A composition comprising:

at least one polysiloxane of claim 1 , and a cosmetic active ingredient, a pharmaceutical active ingredient, or a dermatological active ingredient.

6. A formulation comprising at least one polysiloxane according to claim 1 , and at least one additional ingredient, said at least one additional ingredient comprising an emollient, an emulsifier, a thickener/viscosity regulator/stabilizer, an antioxidant, a hydrotrope, a solid, a filler, a pearlescent additive, an active deodorant ingredient, an antiperspirant ingredient, an insect repellant, a self-tanning agent, a preservative, a conditioner, a perfume, a dye, an active cosmetic ingredient, a care additive, a superfatting agent, or a solvent.

Assignments (2)
MERGER Recorded May 15, 2014
From: EVONIK GOLDSCHMIDT GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 032900/0372 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2012
From: HERRWERTH, SASCHA; HARTUNG, CHRISTIAN; WINTER, PATRICK; FERENZ, MICHAEL; HENNING, FRAUKE
To: EVONIK GOLDSCHMIDT GMBH
Reel/Frame 028565/0919 →