Alkylhydrido siloxanes

• US 5,446,185 A
• Filed: 11/14/1994
• Issued: 08/29/1995
• Est. Priority Date: 11/14/1994
• Status: Expired due to Term

• Current Assignee: Dow, Inc.
• Original Assignee: Dow, Inc.
• Inventors: Legrow, Gary E., Norris, Ann W., Cobb, Vicky S., Mc Vannel, Donald E.
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US08/338,940
• Time in Patent Office: 288 Days
• Field of Search: 556/451
• US Class Current: 556/451
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence

Abstract

Alkylhydrido siloxane fluids including (i) comonomers of the formula RSi(OSiMe₂ H)₃, (ii) oligomers of the formula (HMe₂ SiO)₂ -Si(R)-O-Si(R)-(OSiMe₂ H)₂, and (iii) higher molecular weight siloxane species of the formulas RSi[(OSiMe₂)_x OSiMe₂ H]₃ and [HMe₂ SiO(Me₂ SiO)_x ]₂ SiRORSi[(OSiMe₂)_x OSiMe₂ H]₂, are described in which Me is methyl, and R is a C₂ to C₁₈ straight-chain or branched-chain alkyl substituent. Methods of making the siloxane comonomers, oligomers, and higher molecular weight species, are also disclosed.

Claims

1. Compounds selected from the group consisting of (HMe₂ SiO)₂ -Si(R)-O-Si(R)-(OSiMe₂ H)₂, RSi[(OSiMe₂)_x OSiMe₂ H]₃, and [HMe₂ SiO (Me₂ SiO)_x ]2SiRORSi[(OSiMe₂)_x OSiMe₂ H]₂, in which Me is methyl, R is a C₂ to C₁₈ straight-chain or branched-chain alkyl substituent, and x has a value of 1-100.

2. Compounds according to claim 1 in which R is selected from the group consisting of ethyl;

n-propyl;

isopropyl;

butyl;

2-methylpropyl;

pentyl;

2-methylbutyl;

2,2-dimethylpropyl;

hexyl;

2-methylpentyl;

3-methylpentyl;

2,2-dimethylbutyl;

2,3-dimethylbutyl;

heptyl;

2-methylhexyl;

3-methylhexyl;

2,2-dimethylpentyl;

2,3-dimethylpentyl;

2,4-dimethylpentyl;

3,3-dimethylpentyl;

3-ethylpentyl;

2,2,3-trimethylbutyl;

octyl;

nonyl;

decyl;

undecyl;

dodecyl;

tridecyl;

tetradecyl;

pentadecyl;

hexadecyl;

heptadecyl; and

octadecyl.

3. Compounds according to claim 1 of the formula (HMe₂ SiO)₂ -Si(R)-O-Si(R)-(OSiMe₂ H)₂, in which Me is methyl, and R is a C₂ to C₁₈ straight-chain or branched-chain alkyl substituent.

4. A compound according to claim 3 in which R is n-propyl.

5. Compounds according to claim 1 of the formula RSi[(OSiMe₂)_x OSiMe₂ H]₃, in which Me is methyl, R is a C₂ to C₁₈ straight-chain or branched-chain alkyl substituent, and x has a value of 1-100.

6. A compound according to claim 5 in which R is n-propyl, and x is 4.

7. Compounds according to claim 1 of the formula [HMe₂ SiO (Me₂ SiO)_x ]2SiRORSi[(OSiMe₂)_x OSiMe₂ H]₂, in which Me is methyl, R is a C₂ to C₁₈ straight-chain or branched-chain alkyl substituent, and x has a value of 1-100.

8. A compound according to claim 7 in which R is n-propyl.

9. A method of making compounds of the formula RSi(OSiMe₂ H)₃ and (HMe₂ SiO)₂ -Si(R)-O-Si(R)-(OSiMe₂ H)₂ comprising hydrolyzing an alkyltrichlorosilane of the formula RSiCl₃ with dimethylchlorosilane, wherein Me is methyl, and R is a C₂ to C₁₈ straight-chain or branched-chain alkyl substituent.

10. A method according to claim 9 in which the temperature of the hydrolysis reaction is maintained below 70°

C.

11. A method according to claim 9 in which the temperature of the hydrolysis reaction is maintained below 30°

C.

12. A method according to claim 9 in which the temperature of the hydrolysis reaction is maintained below 15°

C.

13. A method according to claim 9 in which there is employed at least two moles of dimethylchlorosilane for each mole of alkyltrichlorosilane.

14. A method of making compounds of the formula RSi[(OSiMe₂)_x OSiMe₂ H]₃, in which Me is methyls, R is a straight-chain or branched-chain alkyl substituent, and x has a value of 1-100, comprising (i) hydrolyzing an alkyltrichlorosilane with dimethylchlorosilane to form a compound of the formula RSi(OSiMe₂ H)₃, wherein Me is methyl, and R is a straight-chain or branched-chain alkyl substituent;

(ii) reacting the compound RSi(OSiMe₂ H)₃ with a dimethylcyclosiloxane in the presence of an acid catalyst; and

(iii) allowing the reaction to continue for a time sufficient for the reaction to reach a constant steady state condition.

15. A method according to claim 14 in which R is a C₂ to C₁₈ straight-chain or branched-chain alkyl substituent.

16. A method according to claim 15 in which R is selected from the group consisting of ethyl;

n-propyl;

isopropyl;

butyl;

2-methylpropyl;

pentyl;

2-methylbutyl;

2,2-dimethylpropyl;

hexyl;

2-methylpentyl;

3-methylpentyl;

2,2-dimethylbutyl;

2,3-dimethylbutyl;

heptyl;

2-methylhexyl;

3-methylhexyl;

2,2-dimethylpentyl;

2,3-dimethylpentyl;

2,4-dimethylpentyl;

3,3-dimethylpentyl;

3-ethylpentyl;

2,2,3-trimethylbutyl;

octyl;

nonyl;

decyl;

undecyl;

dodecyl;

tridecyl;

tetradecyl;

pentadecyl;

hexadecyl;

heptadecyl; and

octadecyl.

17. Compounds made according to the method defined in claim 14.

18. A method of making compounds of the formula [HMe₂ SiO(Me₂ SiO)_x ]2SiRORSi[(OSiMe₂)_x OSiMe₂ H]₂, in which Me is methyl, R is a straight-chain or branched-chain alkyl substituent, and x has a value of 1-100, comprising (i) hydrolyzing an alkyltrichlorosilane with dimethylchlorosilane to form a compound of the formula (HMe₂ SiO) 2SiRORSi(OSiMe₂ H)=, wherein Me is methyl, and R is a straight-chain or branched-chain alkyl substituent;

(ii) reacting the compound (HMe₂ SiO)₂ SiRORSi(OSiMe₂ H)₂ with a dimethylcyclosiloxane in the presence of an acid catalyst; and

(iii) allowing the reaction to continue for a time sufficient for the reaction to reach a constant steady state condition.

19. A method according to claim 18 in which R is a C₂ to C₁₈ straight-chain or branched-chain alkyl substituent.

20. A method according to claim 19 in which R is selected from the group consisting of ethyl;

n-propyl;

isopropyl;

butyl;

2-methylpropyl;

pentyl;

2-methylbutyl;

2,2-dimethylpropyl;

hexyl;

2-methylpentyl;

3-methylpentyl;

2,2-dimethylbutyl;

2,3-dimethylbutyl;

heptyl;

2-methylhexyl;

3-methylhexyl;

2,2-dimethylpentyl;

2,3-dimethylpentyl;

2,4-dimethylpentyl;

3,3-dimethylpentyl;

3-ethylpentyl;

2,2,3-trimethylbutyl;

octyl;

nonyl;

decyl;

undecyl;

dodecyl;

tridecyl;

tetradecyl;

pentadecyl;

hexadecyl;

heptadecyl; and

octadecyl.

21. Compounds made according to the method defined in claim 18.