Silicone polyether surfactants synthesized using carbamate linkage

• US 5,539,136 A
• Filed: 09/22/1994
• Issued: 07/23/1996
• Est. Priority Date: 08/21/1992
• Status: Expired due to Fees

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Lucarelli, Michael A., Raleigh, William J., Thimineur, Raymond J.
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US08/310,600
• Time in Patent Office: 670 Days
• Field of Search: 556/420
• US Class Current: 556/420
• CPC Class Codes: A61K 8/894 modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
• CPC Class Codes: A61Q 15/00 Anti-perspirants or body deodorants deodorisation of air A61L9/00
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C09K 23/54 Silicon compounds

Abstract

A novel polysiloxane polyether copolymer useful as a silicone surface active agent is disclosed having improved polyether versatility.

Claims

1. A silicone polyether of the general formula

View Dependent Claims (2)

2. A silicone polyether as defined in claim 1 wherein R¹ represents a monomethyl poly(oxyethylene)carbamylisopropylarylmethylethenyl group.

3. A silicone polyether of the general formula ##STR1##

4. A method for preparing a silicone polyether surfactant comprising a polysiloxane copolymer selected from those of the general formulae:

TD_x M'"'"'₃ ;

TD_x D'"'"'_y M'"'"'₃ ;

TD'"'"'_y M'"'"'₃ ;

TD_x D'"'"'_y M₃ ;

TD'"'"'_y M₃ ;

T'"'"'D_x M'"'"'₃ ;

T'"'"'D_x D'"'"'_y M'"'"'₃ ;

T'"'"'D'"'"'_y M'"'"'₃ ;

T'"'"'D'"'"'_y M'"'"'₃ ;

T'"'"'D_x D'"'"'_y M₃ ;

T'"'"'D'"'"'M₃ ;

T'"'"'D_x M₃ ;

M'"'"'D_x D'"'"'_y M'"'"';

M'"'"'D_x M'"'"';

MD'"'"'_y M;

MD_x D'"'"'_y M, M'"'"'D'"'"'_y M'"'"';

M'"'"'Q;

(D'"'"')_z or mixtures of any of the foregoing;

wherein M represents R₃ SiO.sub. 2/2 ;

D represents R₂ SiO.sub. 2/2 ;

T represents RSiO.sub. 3/2 ;

Q represents SiO.sub. 4/2 ;

M'"'"' represents R₂ R¹ SiO.sub. 1/2 ;

D represents RR¹ SiO.sub. 2/2 ;

T'"'"' represents R¹ SiO.sub. 3/2 ;

each R independently represents a saturated or unsaturated monovalent hydrocarbon;

R¹ represents an alkyl poly(oxyalkylene) group;

x is greater than about 1;

y is greater than about 1 and z ranges from 4 to about 12;

comprising the steps of;

(a) reacting an alkenylarylalkylisocyanate with a hydroxy endcapped polyoxyalkylene to produce an alkyl(polyoxyalkylene)carbamylalkylarylalkenyl compound;

(b) reacting the alkyl(polyoxyalkylene)carbamylalkylarylalkenyl compound with a siloxane hydride fluid selected from those of the general formulae;

TD_x M^H₃ ;

TD_x D^Hy M^H₃ ;

TD^H_y M^H₃ ;

TD_x D^H_y M₃ ;

TD^H_y M₃ ;

T^H D_x M^H₃ ;

T^H D_x D^H_y M^H₃ ;

T^H D^H_y M^H₃ ;

T^H D^H_y M^H₃ ;

T^H D_x D^H_y M₃ ;

T^H D^H M₃ ;

T^H D_x M₃ ;

M^H D_x D^H_y M^H ;

M^H D_x M^H ;

MD^H_y M;

MD_x D^H_y M, M^H D^H_y M^H ;

M^H Q;

(D^H)_z wherein M^H represents a dialkyl hydrogen siloxy of the formula R₂ HSiO.sub. 1/2 ;

D^H represents an alkyl hydrogen siloxy of the formula RHSiO.sub. 2/2 ;

T^H represents an hydrogen siloxy of the formula HSiO.sub. 3/2, and wherein M, D, T, Q, R, x, y and z are as defined above to produce said polysiloxane copolymer.

5. A method as defined in claim 4 wherein said siloxane hydride fluid is of the formula MD_x D^H_y M and said polysiloxane copolymer is of the general formula MD_x D'"'"'_y M;

wherein M, D, D'"'"', D^H, x and y are as defined above.

6. A method as defined in claim 5 wherein R represents methyl.

7. A method as defined in claim 5 wherein R¹ represents a monomethyl poly(oxyethylene)carbamylisopropylcumenyl group.

8. A method as defined in claim 5 wherein x ranges from about 1 to about 1000.

9. A method as defined in claim 5 wherein x ranges from about 1 to about 50.

10. A method as defined in claim 5 wherein y ranges from about 1 to about 1000.

11. A method as defined in claim 5 wherein y ranges from about 1 to about 10.

12. A method as defined in claim 5 wherein said alkenylarylalkylisocyanate comprises 1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl)-benzene.

13. A method as defined in claim 5 wherein said hydroxy endcapped polyoxyalkylene comprises monomethyl poly(oxyethylene)hydroxyl.

14. A method as defined in claim 5 wherein step (a) proceeds under substantially anhydrous conditions and in the presence of a stannous carboxylate catalyst.

15. A method as defined in claim 5 wherein step (b) is a hydrosilation reaction in the presence of a platinum catalyst.