Branched polyorganosiloxane polymers

• US 7,390,479 B2
• Filed: 03/19/2003
• Issued: 06/24/2008
• Est. Priority Date: 03/20/2002
• Status: Expired due to Fees

• Current Assignee: GE Bayer Silicones GmbH & Co. KG (Momentive Performance Materials Holdings LLC)
• Original Assignee: GE Bayer Silicones GmbH & Co. KG (Momentive Performance Materials Holdings LLC)
• Inventors: Wagner, Roland, Sockel, Karl-Heinz, Witossek, Anita, Stachulla, Karl-Heinz
• Primary Examiner(s): Zimmer; Marc S.
• Application Number:
  US10/507,551
• Publication Number:
  US 20050255073A1
• Time in Patent Office: 1,924 Days
• Field of Search: None
• US Class Current: 424/70.12
• CPC Class Codes: A61K 8/894 modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• CPC Class Codes: A61K 8/898 containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• CPC Class Codes: A61Q 5/12 Preparations containing hair conditioners
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C11D 3/3742 Nitrogen containing silicones
• CPC Class Codes: D06M 15/643 containing silicon in the main chain
• CPC Class Codes: D06M 15/6436 containing amino groups
• CPC Class Codes: D06M 15/647 containing polyether sequences
• CPC Class Codes: D06M 15/657 containing fluorine
• CPC Class Codes: D06M 2200/50 Modified hand or grip properties; Softening compositions

Abstract

Hydrophilic polyquaternary polyorganosiloxane copolymers and their use as wash-resistant hydrophilic softeners.

Claims

1. Branched polyorganosiloxane polymer containing

at least one group of the structure

2. Branched polyorganosiloxane polymer according to claim 1, wherein the divalent organic group Q containing at least one ammonium group is selected from the group consisting of

3. Branched polyorganosiloxane polymer according to claim 1, wherein

4. Branched polyorganosiloxane polymer according to claim 1, wherein V represents a divalent, straight-chain, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon group with up to 400 carbon atoms which optionally contains one or more groups selected from the group consisting of —

O—

, —

NH—

, —

NR¹—

, where R¹ is defined as above,

5. Branched polyorganosiloxane polymer according to claim 1, comprising repeating units of the structure

6. Branched polyorganosiloxane polymer according to claim 1, comprising repeating units of the structure

7. Branched polyorganosiloxane polymer according to claim 5 or 6 wherein —

V¹—

is selected from the group, consisting of

—

R⁹—

where R⁹ represents a divalent, saturated or singly or multiply unsaturated, straight-chain or branched, hydrocarbon group with two to 25 carbon atoms selected from the group, consisting of

—

(CH₂)_uC(O)O—

[(CH₂CH₂O)_q—

(CH₂CH(CH₃)O)_r]—

C(O)(CH₂)_u—

—

(CH₂)_uC(O)O—

R⁹—

O—

C(O)(CH₂)_u—

, where R⁹ is defined as previously,

—

(CH₂)_u—

R¹⁰—

(CH₂)_u—

, where R10 is an aromatic group,

—

[CH₂CH₂O]_q—

[CH₂CH(CH₃)O]_r—

CH₂CH₂—

,

—

CH(CH₃)CH₂O[CH₂CH₂O]_q—

[CH₂CH(CH₃)O]_r—

CH₂CH(CH₃)—

—

CH₂CH(OH)CH₂—

,

—

CH₂CH(OH)(CH₂)₂CH(OH)CH₂—

,

—

CH₂CH(OH)CH₂OCH₂CH(OH)CH₂OCH₂CH(OH)CH₂— and

—

CH₂CH(OH)CH₂O—

[CH₂CH₂O]_q—

[CH₂CH(CH₃)O]_r—

CH₂CH(OH)CH₂—

where

u is from 1 to 3,

q is from 0 to 200,

r is from 0 to 200, and

q+r>

0.

8. Branched polyorganosiloxane polymer according to claim 5 or 6, comprising a group of the structure

9. Branched polyorganosiloxane polymer according to claim 1, wherein

S^v is a trivalent or higher valent organopolysiloxane group which has at least three silicon atoms which are each connected to three or more groups V or V^v

via a bond to a carbon atom of the respective group V or V^v.

10. Branched polyorganosiloxane polymer according to claim 2, comprising a branching group of the formula

V^1v(—

Q—

)_x, where V^1v(—

Q—

)_x is a trivalent or higher valent group, where Q is defined as above, and x is a whole number of at least three, and where V^1v is selected from the group consisting of;

R¹¹—

[(CH₂CH₂O)_v(CH₂CH(CH₃)O)_w—

CO—

(CH₂)_u]_3-6—

, where

R¹¹ is a trivalent or hexavalent group which is derived from a polyol in which 3 to 6 hydroxyl-hydrogen atoms are substituted,

v and w are numbers from 0 to 200,

v+w≧

0, and

u=1 to 3

R¹¹—

[(CH₂CH₂O)_v(CH₂CH(CH₃)O)_w—

CH₂CH(OH)CH₂]_3-6—

, where R¹¹, v, and w are defined as above

11. Branched polyorganosiloxane polymer according to claim 10, wherein the polyol is selected from the group consisting of:

glycerol, trimethylolpropane, pentaerythritol, sorbitol, and sorbitan.

12. Branched polyorganosiloxane polymer according to claim 1, comprising a branching group of the structure V^2v which is connected to at least one group S or S^v and where V^2v is a trivalent or higher valent group which is selected from the group consisting of:

—

(Z—

)_yR¹²[—

CH₂CH₂O)_v(CH₂CH(CH₃)O)_w—

CO—

CH₂)_u]_z—

, where

R¹² is a trivalent or hexavalent group which is derived from a polyol in which 3 to 6 hydroxyl-hydrogen atoms are substituted, and

Z is a divalent hydrocarbon group with up to 20 carbon atoms which optionally contains one or more groups selected from the group consisting of —

O— and

—

C(O)—

, which optionally are substituted with one or more hydroxyl groups, and where the group Z is bonded by one of its carbon atoms to a silicon atom of the groups S or S^v,

v and w are numbers from 0 to 200,

v+w≧

0,

u=1 to 3,

y=1 to 6,

z=0 to 5,

z+y=3 to 6,

(—

)_mR¹³[—

O(CH₂CH₂O)_v(CH₂CH(CH₃)O)_w—

CO—

CH₂)_u]_n—

, where

R¹³ is a trivalent or hexavalent, saturated or unsaturated, linear, branched or cyclic hydrocarbon group with up to 10 carbon atoms,

(—

) represents a single bond to a silicon atom of the group S or S^v,

v and w are numbers from 0 to 200,

v+w≧

0,

u=1 to 3,

m=1 or 2,

n=1 to 5, and

m+n=3 to 6

(—

)_mR¹³[—

O(CH₂CH₂O)_v(CH₂CH(CH₃)O)_w—

CH₂CH(OH)CH₂]_n—

, where

m, R¹³, v, w, and n are defined as above,

—

(Z—

)_yR¹²[—

(CH₂CH₂O)_v(CH₂CH(CH₃)O)_w—

CH₂CH(OH)CH₂]_z—

, where

Z, y, R¹², v, w, and z are defined as above.

13. Branched polyorganosiloxane polymer according to claim 1, wherein S^v and V^v are branching units and the molar ratio of the sum of the branching units S^v and V^v to the sum of the linear repeating units S, V, and Q is 0.001% to 20%.

14. Branched polyorganosiloxane polymer according to one of claims 9 to 13, where the molar ratio of V^v to V is from 0.002% to 20%.

15. Branched polyorganosiloxane polymer according to claim 1, 2, 3, 4, 5, 6, 9, 10, 11, 12, or 13, where the molar ratio of S^v to S is from 0.002% to 20%.

16. Process for the production of the branched polyorganosiloxane polymer of claim 1, comprising conversion of:

a) at least one organic compound which has two amino groups and which optionally comprises a polyorganosiloxane group, with

b) at least one organic compound which has two epoxy groups and which optionally comprises a polyorganosiloxane group, with

c) at least one organic compound which has two halogen alkylcarbonyloxy groups and which optionally comprises a polyorganosiloxane group, as well as

d) at least one branching compound containing at least three functionalities selected from the group consisting of amine, epoxy, or chloroalkylcarbonyloxy functional groups.

wherein at least one of the compounds a) to d) contains a polyorganosiloxane group.

17. A cosmetic formulation, washing agent or formulation for the surface treatment of substrates comprising the branched polyorganosiloxane polymer of claim 1.

18. A shampoo, 2-in-1 shampoo, clear and turbid leave-on conditioner, hair rinse or pearl sheen formulation, setting gel, setting foam, setting aerosol, or hair-dyeing formulation, comprising the branched polyorganosiloxane polymer of claim 1.