Granted Patent B2

US 8,569,385 · App. 12/955,276 · Granted Oct 29, 2013

Abstract

Claims (144)

1. An aqueous emulsion composition comprising a discontinuous phase and a continuous phase wherein said discontinuous phase comprises water and said continuous phase a silane having the formula:

(R 1 )(R 2 )(R 3 )Si—R 4 —Si(R 5 )(R 6 )(R 7 )

wherein

R 1 , R 2 , R 3 , R 5 , and R 6 are each methyl;

R 4 is a hydrocarbon group of 1 to 3 carbons;

R 7 is selected from the group consisting of R 9 —R C , and R 10 —R Z ;

R 9 is a monovalent radical selected from the group consisting of

R 16 (O) w (R 17 ) x —, and R 18 O(C 2 H 4 O) d (C 3 H 8 O) e (C 4 H 8 O) f CH 2 CH(OH)CH 2 ;

where R 16 and R 17 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms; R 18 is a divalent hydrocarbon group of 2 to 4 carbon atoms; subscripts w and x are 1;

the subscripts d, e and f are zero or positive and satisfy the following relationships:

1 ≦d+e+f≦ 10 with d≧ 1;

R c is selected from the group consisting of N(R 19 )(R 20 ),

where R 19 and R 20 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, R 26 N(R 29 )(R 30 ), and —R 27 O(C 7 H 4 O) g (C 3 H 6 O) h (C 4 H 8 O) i R 28 ;

the subscripts g, h and i are zero or positive and satisfy the following relationships:

1 ≦g+h+i≦ 10 with g≧ 1;

R 21 , R 23 , R 24 , R 25 are each independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;

R 22 is a monovalent radical selected from the group consisting of H, branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and —R 31 O(C 2 H 4 O) j C 3 H 6 O) k (C 4 H 8 O) l R 32 ;

the subscripts j, k and l are zero or positive and satisfy the following relationships:

1 ≦j+k+l≦ 10 with j≧ 1;

R 26 is a divalent hydrocarbon radical of 1 to 6 carbons, or

R 33 O(C 7 H 4 O) m (C 3 H 6 O) n (C 4 H 8 O) o R 34 ;

the subscripts m, n and o are zero or positive and satisfy the following relationships:

1 ≦m+n+o≦ 10 with m≧ 1;

R 29 and R 30 are independently selected from the group consisting of H, branched monovalent hydrocarbon radical of 1 to 4 carbons, and linear monovalent hydrocarbon radical of 1 to 4 carbons;

R 27 , R 31 and R 33 are independently selected from the group consisting of a divalent hydrocarbon group of 2 to 4 carbon atoms;

R 28 is a monovalent radical selected from the group consisting of H, a monovalent hydrocarbon radical of 1 to 6 carbons and N(R 40 )(R 41 );

R 32 and R 34 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and R 37 N(R 38 )(R 39 ); where R 37 is a divalent hydrocarbon radical of 1 to 6 carbons;

R 35 , R 36 , R 38 and R 39 are independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;

R 10 is a monovalent radical selected from the group consisting of R 40 (O) y (R 41 ) z — and R 42 O(C 2 H 4 O) p (C 3 H 6 O) q (C 4 H 8 O) r CH 2 CH(OH)CH 2 —; where R 40 and R 41 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms;

R 42 is a divalent hydrocarbon group of 2 to 4 carbon atoms;

the subscripts y and z are 1;

the subscripts p, q and r are zero or positive and satisfy the following relationships:

1 ≦p+q+r≦ 10 with p≧ 1;

R Z is —N—(R 43 )(R 44 ) α R 45 SO 3 (M K ) β -, —N—(R 46 )(R 47 ) γ R 48 COO(M K ) δ , —N+—(R 49 )(R 50 )R 51 OP(═O)(A)(B) or, (—C(═O)N(R 52 )R 53 N—(R 54 )(R 55 )) + -(R 56 OP(═O)(A)(B))(X) ε ; where R 43 , R 44 , R 46 , R 47 , R 49 , R 50 , R 52 , R 54 and R 55 are independently selected from the group consisting of H, a branched monovalent hydrocarbon radical of 1 to 4 carbons, linear monovalent hydrocarbon radical of 1 to 4 carbons, and an alkanolamine group having alkyl groups of 2 to 4 carbons; R 45 is a divalent group of 3 to 4 carbons;

M K is a cation selected from the group consisting of Na + , K + , Ca 2+ , NH 4 + Li + monovalent ammonium ions derived from mono-, di- and trialkylamines comprising alkyl groups of 2 to 4 carbons and mono-, di- and trialkanolamines comprising alkyl groups of 2 to 4 carbons;

subscripts α, β, γ and δ are zero or 1 subject to the following relationships: α+β=1 and γ+δ=1;

R 48 and R 51 are independently a divalent group of 1 to 4 carbons;

R 53 and R 56 are each independently a divalent group of 2 to 4 carbons;

A and B are selected from O − and OM K ; X is an anion selected from the group consisting of Cl, Br, and I; and the subscript ε is 0, 1 or 2.

2. The composition of claim 1 where R 7 is R 9 —Rc.

3. The composition of claim 1 where R C C is N(R 19 )(R 20 ).

4. The composition of claim 1 where R 7 is R 10 -R Z .

5. The composition of claim 1 where R Z is —N—(R 43 )(R 44 ) α R 45 SO 3 (M K ) δ .

6. The composition of claim 1 where R Z is —N—(R 46 )(R 47 ) γ R 48 COO(M K ) δ .

7. A non-aqueous emulsion comprising a discontinuous phase and a continuous phase wherein said discontinuous phase comprises a non-aqueous hydroxylic solvent and said continuous phase a silane having the formula:

(R 1 )(R 2 )(R 3 )S 1 —R 4 —Si(R 5 )(R 6 )(R 7 )

wherein

R 1 , R 2 , R 3 , R 5 , and R 6 are each methyl;

R 4 is a hydrocarbon group of 1 to 3 carbons;

R 7 is selected from the group consisting of R 9 —R C and R 10 —R Z ;

R 9 is a monovalent radical selected from the group consisting of

R 16 (O) w (R 17 ) x — and R 18 O(C 2 H 4 O) d (C 3 H 6 O) e (C 6 H 8 O) f CH 2 CH(OH)CH 2 ;

where R 16 and R 17 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms; R 18 is a divalent hydrocarbon group of 2 to 4 carbon atoms; subscripts w and x are 1;

the subscripts d, e and f are zero or positive and satisfy the following relationships:

1 ≦d+e+f≦ 10 with d≧ 1;

R C is selected from the group consisting of N(R 19 )(R 20 ),

where R 19 and R 20 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, R 26 N(R 29 )(R 30 ), and —R 27 O(C 2 H 4 O) g (C 3 H 6 O) h (C 4 H 8 O) i R 28 ;

the subscripts g, h and i are zero or positive and satisfy the following relationships:

1 ≦g+h+i≦ 10 with g≧ 1;

R 21 , R 23 , R 24 , R 25 are each independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;

R 22 is a monovalent radical selected from the group consisting of H, branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and —R 31 O(C 2 H 4 O) i (C 3 H 6 O) k (C 4 H 8 O) l R 32 ;

the subscripts j, k and l are zero or positive and satisfy the following relationships:

1 ≦j+k+l≦ 10 with j≧ 1;

R 26 is a divalent hydrocarbon radical of 1 to 6 carbons, or

R 33 O(C 2 H 4 O) m (C 3 H 6 O) n (C 4 H 8 O) o R 34 ;

the subscripts m, n and o are zero or positive and satisfy the following relationships:

1 ≦m+n+o≦ 10 with m≧ 1;

R 29 and R 30 are independently selected from the group consisting of H, branched monovalent hydrocarbon radical of 1 to 4 carbons, and linear monovalent hydrocarbon radical of 1 to 4 carbons;

R 27 , R 31 and R 33 are independently selected from the group consisting of a divalent hydrocarbon group of 2 to 4 carbon atoms;

R 28 is a monovalent radical selected from the group consisting of H, a monovalent hydrocarbon radical of 1 to 6 carbons and N(R 40 )(R 41 );

R 32 and R 34 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and R 37 N(R 38 )(R 39 ); where R 37 is a divalent hydrocarbon radical of 1 to 6 carbons;

R 35 , R 36 , R 38 and R 39 are independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;

R 10 is a monovalent radical selected from the group consisting of

R 40 (O) y (R 41 ) z — and R 42 O(C 2 H 4 O) p (C 3 H 6 O) q (C 4 H 8 O) r CH 2 CH(OH)CH 2 —;

where R 40 and R 41 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms;

R 42 is a divalent hydrocarbon group of 2 to 4 carbon atoms;

the subscripts y and z are 1;

the subscripts p, q and r are zero or positive and satisfy the following relationships:

1 ≦p+q+r≦ 10 with p≧ 1;

R Z is —N—(R 43 )(R 44 ) α R 45 SO 3 (M K ) β , —N—(R 46 )(R 47 )γR 48 COO(M K ) δ ,

—N + —(R 49 )(R 50 )R 51 OP(═O)(A)(B) or,

(—C(═O)N(R 52 )R 53 N—(R 54 )(R 55 )) + -(R 56 OP(═O)(A)(B))(X − ) ε ;

where R 43 , R 44 , R 46 , R 47 , R 49 , R 50 , R 52 , R 54 and R 55 are independently selected from the group consisting of H, branched monovalent hydrocarbon radical of 1 to 4 carbons, linear monovalent hydrocarbon radical of 1 to 4 carbons and an alkanolamine group having alkyl groups of 2 to 4 carbons; and R 45 is a divalent group of 3 to 4 carbons;

M K is a cation selected from the group consisting of Na + ,K + , Ca 2+ , NH 4+ , and Li + , monovalent ammonium ions derived from mono-, di- and trialkylamines comprising alkyl groups of 2 to 4 carbons, and mono-, di- and trialkanolamines comprising alkyl groups of 2 to 4 carbons;

subscripts α, β, γ and δ are zero or 1 subject to the following relationships:

α+β=1 and γ+δ=1;

R 48 and R 51 are independently a divalent group of 1 to 4 carbons;

R 53 and R 56 are each independently a divalent group of 2 to 4 carbons;

A and B are selected from O − and OM K ; X is an anion selected from the group consisting of Cl, Br, and I; and the subscript ε is 0, 1 or 2.

8. The non-aqueous emulsion of claim 7 where R 7 is R 9 —R C .

9. The non-aqueous emulsion of claim 7 where R C is N(R 19 )(R 20 ).

10. The non-aqueous emulsion of claim 7 where R 7 is R 10 —R Z .

11. The non-aqueous emulsion of claim 7 where R Z is —N—(R 43 )(R 44 ) c ,R 45 SO 3 (M K ) β .

12. The non-aqueous emulsion of claim 7 where R Z is —N—(R 46 )(R 47 ) γ R 48 COO(M K ) δ .

13. A non-aqueous emulsion comprising a continuous phase and a discontinuous phase wherein said continuous phase comprises a non-aqueous hydroxylic organic solvent and said discontinuous phase comprises a silane having the formula:

(R 1 )(R 2 )(R 3 )Si—R 4 —Si(R 5 )(R 6 )(R 7 )

wherein

R 1 , R 2 , R 3 , R 5 , and R 6 are each methyl;

R 4 is a hydrocarbon group of 1 to 3 carbons;

R 7 is selected from the group consisting of R 9 —R C and R 10 —R Z ;

R 9 is a monovalent radical selected from the group consisting of

R 16 (O) w (R 17 ) x — and R 18 O(C 2 H 4 O) d (C 3 H 6 O) e (C6H 8 O) f CH 2 CH(OH)CH 2 ;

where R 16 and R 17 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms; R 18 is a divalent hydrocarbon group of 2 to 4 carbon atoms; subscripts w and x are 1;

the subscripts d, e and f are zero or positive and satisfy the following relationships:

1 ≦d+e+f≦ 10 with d≧ 1;

R C is selected from the group consisting of N(R 19 )(R 20 ),

where R 19 and R 20 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, R 26 N(R 29 )(R 30 ), and —R 27 O(C 2 H 4 O) g (C 3 H 6 O) h (C 4 H 8 O) i R 28 ;

the subscripts g, h and i are zero or positive and satisfy the following relationships:

1 ≦g+h+i≦ 10 with g≧ 1;

R 21 , R 23 , R 24 , R 25 are each independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;

R 22 is a monovalent radical selected from the group consisting of H, branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and —R 31 O(C 2 H 4 O) j (C 3 H 6 O) k (C 4 H 8 O) l R 32 ;

the subscripts j, k and 1 are zero or positive and satisfy the following relationships:

1 ≦j+k+l≦ 10 with j≧ 1;

R 26 is a divalent hydrocarbon radical of 1 to 6 carbons, or

R 33 O(C 2 H 4 O) m (C 3 H 6 O) n (C 4 H 8 O) o R 34 ;

the subscripts m, n and o are zero or positive and satisfy the following relationships:

1 ≦m+n+o≦ 10 with m≧ 1;

R 29 and R 30 are independently selected from the group consisting of H, branched monovalent hydrocarbon radical of 1 to 4 carbons, and linear monovalent hydrocarbon radical of 1 to 4 carbons;

R 27 , R 31 and R 33 are independently selected from the group consisting of a divalent hydrocarbon group of 2 to 4 carbon atoms;

R 28 is a monovalent radical selected from the group consisting of H, a monovalent hydrocarbon radical of 1 to 6 carbons and N(R 40 )(R 41 );

R 32 and R 34 are independently selected from the group consisting of H, a branched or linear monovalent hydrocarbon radical of 1 to 4 carbons, and R 37 N(R 38 )(R 39 ); where R 37 is a divalent hydrocarbon radical of 1 to 6 carbons;

R 35 , R 36 , R 38 and R 39 are independently selected from the group consisting of H and branched or linear monovalent hydrocarbon radicals of 1 to 4 carbons;

R 10 is a monovalent radical selected from the group consisting of

R 40 (O) y (R 41 ) n — and R 42 O(C 2 H 4 O) p (C 3 H 6 O) q (C 4 H 8 O) r CH 2 CH(OH)CH 2 —;

where R 40 and R 41 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms;

R 42 is a divalent hydrocarbon group of 2 to 4 carbon atoms;

the subscripts y and z are 1;

the subscripts p, q and r are zero or positive and satisfy the following relationships:

1 ≦p+q+r≦ 10 with p≧ 1;

R Z is —N—(R 43 )(R 44 ) α R 45 SO 3 (M K ) β , —N—(R 46 )(R 47 ) γ R 48 COO(M K ) δ ,

—N+—(R 49 )(R 50 )R 51 OP(═O)(A)(B) or,

(—C(═O)N(R 52 )R 53 N—(R 54 )(R 55 ))+—(R 56 OP(═O)(A)(B))(X) ε ;

where R 43 , R 44 , R 46 , R 47 , R 49 , R 50 , R 52 , R 54 and R 55 are independently selected from the group consisting of H, branched monovalent hydrocarbon radical of 1 to 4 carbons, linear monovalent hydrocarbon radical of 1 to 4 carbons and an alkanolamine group having alkyl groups of 2 to 4 carbons; and R 45 is a divalent group of 3 to 4 carbons;

M K is a cation selected from the group consisting of Na + ,K + , Ca 2+ , NH 4+ , and Li + , monovalent ammonium ions derived from mono-, di- and trialkylamines comprising alkyl groups of 2 to 4 carbons, and mono-, di- and trialkanolamines comprising alkyl groups of 2 to 4 carbons;

subscripts α, β, γ and δ are zero or 1 subject to the following relationships:

α+β=1 and γ+δ=1;

R 48 and R 51 are independently a divalent group of 1 to 4 carbons;

R 53 and R 56 are each independently a divalent group of 2 to 4 carbons;

A and B are selected from O − and OM K ; X is an anion selected from the group consisting of Cl, Br, and I; and the subscript ε is 0, 1 or 2.

14. The non-aqueous emulsion of claim 13 where R 7 is R 9 —R C .

15. The non-aqueous emulsion of claim 13 where R C is N(R 19 )(R 20 ).

16. The non-aqueous emulsion of claim 13 where R 7 is R 10 —R Z .

17. The non-aqueous emulsion of claim 13 where R Z is —N—(R 43 )(R 44 ) α R 45 SO 3 (M K ) β .

18. The non-aqueous emulsion of claim 13 where R Z is —N—(R 46 )(R 47 ) γ R 48 COO(M K ) δ .

Assignments (12)