Polyorganosiloxane gels having glycoside groups

• US 10,053,543 B2
• Filed: 12/15/2014
• Issued: 08/21/2018
• Est. Priority Date: 12/17/2013
• Status: Active Grant

• Current Assignee: Wacker Chemie AG (Dr. Alexander Wacker Familiengesellschaft Mit Beschrã¤Nkter Haftung)
• Original Assignee: Wacker Chemie AG (Dr. Alexander Wacker Familiengesellschaft Mit Beschrã¤Nkter Haftung)
• Inventors: Knoer, Sebastian
• Primary Examiner(s): Pipic, Alma
• Application Number:
  US15/104,053
• Publication Number:
  US 20160311980A1
• Time in Patent Office: 1,345 Days
• CPC Class Codes: A61K 8/042 Gels
• CPC Class Codes: A61K 8/891 saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: C08G 2210/00 Compositions for preparing hydrogels
• CPC Class Codes: C08G 77/08 characterised by the catalysts used
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/14 containing silicon bound to oxygen-containing groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08K 5/1545 Six-membered rings
• CPC Class Codes: C08K 5/56 Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

Organopolysiloxane gel compositions containing an organopolysiloxane gel produced by hydrosilylation of an unsaturated silicone resin and a compound containing glycoside residues and a hydrosilylatable group with at least one Si—H-functional organopolysiloxane can form creamy, storage-stable gels which are capable of containing large amounts of polar or hydrophilic substances such as water and glycerol while remaining monophasic. The compositions are especially useful in providing cosmetic compositions with a silky skinfeel.

Claims

1. A composition comprising at least one organopolysiloxane gel having glycoside residues prepared by reacting:

(1a) unsaturated organopolysiloxane resin(s) and

(1b) compound(s) having a glycoside residue and a hydrosilylatable group,

with the proviso that the proportion by weight of the compound (1b), based on the total weight of the organopolysiloxane gel, is 0.1% to 10% by weight,

with

(2) Si-H-functional organopolysiloxane(s) of the formula

H_cR_3-cSiO(R₂SiO)_a(RHSiO)_bSiR_3-cH_c 

 

(I)

where

c is 0 or 1,

R are the same or different and are monovalent, optionally substituted hydrocarbyl radicals having 1 to 18 carbon atoms per radical,

a and b are integers, with the proviso that the sum of a+b is 66 to 248,

wherein the organopolysiloxanes (2) contain Si-bonded hydrogen in amounts of 0.011% to 0.044% by weight,

and the average number of Si-H groups per molecule is greater than 2 and less than 5,

or mixtures of Si-H-functional organopolysiloxanes (2) with

(2′

) Si-H-functional organopolysiloxanes of the formula

H_cR_3-cSiO(R₂SiO)_a(RHSiO)_bSiR_3-cH_c 

 

(I′

)

where

c is 0 or 1,

R is as defined above,

a and b are integers, with the proviso that the sum of a+b is 8 to 248,

and the organopolysiloxanes (2′

) contain Si-bonded hydrogen in amounts of 0.045% to 0.35% by weight,

in the presence of

(3) catalysts that promote the addition of Si-bonded hydrogen onto aliphatic multiple bonds, where (1a) and (1b), and (2) or mixtures of (2) and (2′

) are dispersed in

(4) diluent(s).

2. The composition of claim 1, wherein the diluent(s) comprise organopolysiloxanes having 2 to 200 silicon atoms or organic diluents or mixtures of organopolysiloxanes having 2 to 200 silicon atoms and organic diluents.

3. The composition of claim 1, wherein Si—

H-functional organopolysiloxanes (2) contain Si-bonded hydrogen in an amount of 0.019-0.044 wt. %.

4. The composition of claim 1, wherein Si—

H-functional organopolysiloxanes (2′

) contain Si-bonded hydrogen in an amount of 0.045-0.156 wt. %.

5. A creamy, storage-stable organopolysiloxane gel composition, prepared by homogenizing a composition of claim 1.

6. A creamy, storage-stable organopolysiloxane gel composition, prepared by homogenizing a composition of claim 1 in the presence of further diluent(s) (4) and/or active ingredients for personal care or healthcare.

7. The composition of claim 1, wherein

(1a) the unsaturated organopolysiloxane resins comprise

MQ resins composed of units of the formulae

SiO₂(Q units) and

R₃SiO_1/2 and R₂R′

SiO1/2(M units),

where

R are the same or different and are monovalent, optionally substituted hydrocarbyl radical having 1 to 18 carbon atoms per radical,

R′

is a monovalent hydrocarbyl radical onto which may be added Si—

H groups in a hydrosilylation reaction,

with the proviso that the MQ resins contain at least 2 R′

radicals, and that the molar ratio of M units to Q units is in the range from 0.5 to 4.0.

8. The composition of claim 7, wherein the R′

radicals comprise vinyl radicals.

9. The composition of claim 7, wherein the molar ratio of M units to Q units is from 0.5 to 2.0.

10. The composition of claim 1, wherein the compound(s) (1b) correspond to the formula

Z—

(R¹O)_p—

R² 

 

(III)

where

Z is a glycoside residue formed from 1 to 10 monosaccharide units,

R¹ are the same or different and are divalent hydrocarbyl radicals having 2 to 4 carbon atoms,

R² are monovalent hydrocarbyl radicals having 2 to 12 carbon atoms, onto which may be added Si—

H groups in a hydrosilylation reaction, and

p is 0 or an integer from 1 to 20.

11. The composition of claim 10, where Z is a glycoside residue comprising glucose units.

12. The composition of claim 10, wherein R² is a monovalent C_2-12 hydrocarbyl radical having a terminal aliphatic multiple C—

C bond.

13. The composition of claim 1, wherein the diluent(s) (4) comprise polydimethylsiloxane(s) having 2 to 50 silicon atoms, aliphatic or alicyclic hydrocarbons having 4 to 30 carbon atoms, or esters of carboxylic acids having 2 to 30 carbon atoms.

14. The composition of claim 1, which is a monophasic homogeneous mixture comprising:

(a) organopolysiloxane gels having glycoside residues, and

(b) at least one polar or hydrophilic solvent.

15. The composition of claim 14, wherein the at least one polar or hydrophilic solvent (b) are selected from the group consisting of water, glycerol, ethylene glycol, diethylene glycol, propylene glycol, and mixtures thereof.

16. A process for producing a composition comprising at least one organopolysiloxane gel having glycoside residues of claim 1, comprising reacting

(1a) unsaturated organopolysiloxane resin(s) and

(1b) compound(s) having a glycoside residue and a hydrosilylatable end group,

with the proviso that the proportion by weight of compound(s) (1b), based on the total weight of the organopolysiloxane gel, is 0.1% to 10% by weight,

with

(2) Si—

H-functional organopolysiloxane(s) of the formula

H_cR_3-cSiO(R2SiO)_a(RHSiO)_bSiR_3-cH_c 

 

(I)

where

c is 0 or 1,

R are the same or different and are monovalent, optionally substituted hydrocarbyl radicals having 1 to 18 carbon atoms per radical,

a and b are integers, with the proviso that the sum of a+b is 66 to 248,

the organopolysiloxanes (2) contain Si-bonded hydrogen in amounts of 0.011% to 0.044% by weight,

and the average number of Si—

H groups per molecule is greater than 2,

or mixtures of Si—

H-functional organopolysiloxane(s) (2) with

(2′

) Si—

H-functional organopolysiloxane(s) of the formula

H_cR_3-cSiO(R₂SiO)_a(RHSiO)_bSiR_3-cH_c 

 

(I′

)

where

c is 0 or 1,

R is as defined above,

a and b are integers, with the proviso that the sum of a+b is 8 to 248,

and the organopolysiloxanes (2′

) contain Si-bonded hydrogen in amounts of 0.045% to 0.35% by weight,

in the presence of

(3) catalysts that promote the addition of Si-bonded hydrogen onto aliphatic multiple bonds, where (1a) and (1b), and (2) or mixtures of (2) and (2′

) are dispersed in

(4) diluent(s).

17. The process of claim 16, wherein the diluent(s) comprise organopolysiloxanes having 2 to 200 silicon atoms or organic diluents or mixtures of organopolysiloxanes having 2 to 200 silicon atoms and organic diluents.

18. The process of claim 16, wherein the organopolysiloxane gels obtained after reacting are homogenized to form creamy, storage-stable organopolysiloxane gel compositions.

19. The process of claim 18, wherein the organopolysiloxane gels thus obtained are diluted with further diluent(s) (4) and/or active ingredients for personal care or healthcare, and then optionally homogenized.

20. The process of claim 16, wherein the

(1a) unsaturated organopolysiloxane resins comprise

MQ resins composed of units of the formulae

SiO₂(Q units) and

R₃SiO_1/2 and R₂R′

SiO_1/2(M units),

R are the same or different and are monovalent, optionally substituted hydrocarbyl radical having 1 to 18 carbon atoms per radical,

R′

is a monovalent hydrocarbyl radical onto which may be added Si—

H groups in a hydrosilylation reaction,

with the proviso that the MQ resins contain at least 2 R′

radicals, and that the molar ratio of M units to Q units is in the range from 0.5 to 4.0.

21. The process of claim 16, wherein the compound (1b) comprises a compound of the formula

Z—

(R¹O)_p—

R² 

 

(III)

where

Z is a glycoside residue formed from 1 to 10 monosaccharide units,

R¹ are the same or different and are divalent hydrocarbyl radicals having 2 to 4 carbon atoms,

R² are monovalent hydrocarbyl radicals having 2 to 12 carbon atoms, onto which may be added Si—

H groups in a hydrosilylation reaction, and

p is 0 or an integer from 1 to 20.

22. The process of claim 16, wherein the diluent(s) (4) comprise at least one of polydimethylsiloxanes having 2 to 50 silicon atoms, aliphatic or alicyclic hydrocarbons having 4 to 30 carbon atoms, or esters of carboxylic acids having 2 to 30 carbon atoms.

23. A cosmetic composition, comprising at least one composition comprising organopolysiloxane gels having glycoside residues of claim 1.

24. A cosmetic composition, comprising at least one composition comprising organopolysiloxane gels having glycoside residues produced by the process of claim 16.

25. The composition of claim 1, wherein the weight ratio of organopolysiloxanes (2) to organopolysiloxanes (2′

) is greater than 0.2.

26. The composition of claim 1, wherein the weight ratio of organopolysiloxanes (2) to organopolysiloxanes (2′

) is greater than 0.5.

27. The composition of claim 1, wherein the weight ratio of organopolysiloxanes (2) to organopolysiloxanes (2′

) is greater than 1.