HYDROLYSIS RESISTANT ORGANOMODIFIED SILYLATED IONIC SURFACTANTS
The present invention provides for a composition comprising 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 independently selected from the group consisting of 1 to 6 monovalent hydrocarbon radicals, aryl, and a hydrocarbon group of 7 to 10 carbons containing an aryl group; R 4 is a hydrocarbon group of 1 to 3 carbons; R 7 comprises an anionic, cationic or zwitterionic substituent. The silanes of the present invention exhibit resistance to hydrolysis over a wide pH range.
1 . An agricultural composition comprising:
a) 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 independently selected from the group consisting of 1 to 6 monovalent hydrocarbon radicals, aryl, and a hydrocarbon group of 7 to 10 carbons containing an aryl group;
R 4 is a hydrocarbon group of 1 to 3 carbons;
R 7 is R 8 —R A , R 9 —R C , and R 10 —R Z ;
R 8 is selected from the group consisting of R 11 (O) t (R 12 ) u (O) v —,
R 14 O(C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c —;
where R 11 and R 12 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms, that may each be optionally substituted with one or more OH radicals; R 13 is a divalent hydrocarbon group of 2 to 4 carbon atoms; R 14 is a divalent linear or branched hydrocarbon group of 1 to 6 carbons; subscripts t, u and v are zero or 1;
the subscripts a, b and c are zero or positive and satisfy the following relationships:
1 ≦a+b+c ≦10 with a≧1;
R A is a monovalent radical selected from the group consisting of —SO 3 M K ,
—C(═O)CH 2 CH(R 15 )COO-M K ; —PO 3 HM K ; —COOM K ; where R 15 is H or —SO 3 M K ;
M K is a cation selected from the group consisting of Na + , K + , Ca 2+ , NH 4 + , Li + , and monovalent ammonium ions derived from mono-, di- and trialkylamines comprising alkyl groups of 2 to 4 carbons or mono-, di- and trialkanolamines comprising alkyl groups of 2 to 4 carbons;
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 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 zero or 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) i 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 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 or a branched or 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 zero or 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 45 , 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 or linear monovalent hydrocarbon radical of 1 to 4 carbons, and an alkanolamine group comprising alkyl groups 2 to 4 carbons; R 45 is a divalent group of 3 to 4 carbons;
subscripts subscripts α, β, γ, δ and ε 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;
b) and an agricultural component,
wherein said agricultural composition has an enhanced resistance to hydrolysis.
2 . The composition of claim 1 where R 1 , R 2 , R 3 , R 5 and R 6 are methyl.
3 . The composition of claim 2 where R 7 is R 8 —R A .
4 . The composition of claim 3 where R A is —SO 3 M K .
5 . The composition of claim 3 where R A is —COOM K .
6 . The composition of claim 2 where R 7 is R 9 —R C .
7 . The composition of claim 6 where R C is N(R 19 )(R 20 ).
8 . The composition of claim 2 where R 7 is R 10 —R Z .
9 . The composition of claim 8 where R Z is —N—(R 43 )(R 44 ) □ R 45 SO 3 (M K ) □ .
10 . The composition of claim 8 where R Z is —N—(R 46 )(R 47 ) □ R 48 COO(M K ) □ .
11 . A personal care composition comprising:
a) the silane of claim 1 ; and
b) a personal care component,
wherein said personal care composition has an enhanced resistance to hydrolysis.
12 . The composition of claim 11 where R 1 , R 2 , R 3 , R 5 and R 6 are methyl.
13 . The composition of claim 12 where R 7 is R 8 —R A .
14 . The composition of claim 13 where R A is —SO 3 M K .
15 . The composition of claim 13 where R A is —COOM K .
16 . The composition of claim 12 where R 7 is R 9 —R C .
17 . The composition of claim 16 where R C is N(R 19 )(R 20 ).
18 . The composition of claim 12 where R 7 is R 10 —R Z .
19 . The composition of claim 18 where R Z is —N—(R 43 )(R 44 ) □ R 45 SO 3 (M K ) □ .
20 . The composition of claim 18 where R Z is —N—(R 46 )(R 47 ) □ R 48 COO(M K ) □ .
21 . An oil and gas treatment composition comprising:
a) the silane of claim 1 ; and
b) an oil and gas treating component,
wherein said oil and gas treatment composition has an enhanced resistance to hydrolysis.
22 . The composition of claim 21 where R 1 , R 2 , R 3 , R 5 and R 6 are methyl.
23 . The composition of claim 22 where R 7 is R 8 —R A .
24 . The composition of claim 23 where R A is —SO 3 M K .
25 . The composition of claim 23 where R A is —COOM K .
26 . The composition of claim 22 where R 7 is R 9 —R C .
27 . The composition of claim 26 where R C is N(R 19 )(R 20 ).
28 . The composition of claim 22 where R 7 is R 10 —R Z .
29 . The composition of claim 28 where R Z is —N—(R 43 )(R 44 ) □ R 45 SO 3 (M K ) □ .
30 . The composition of claim 28 where R Z is —N—(R 46 )(R 47 ) □ R 48 COO(M K ) □ .
31 . A water treatment composition comprising:
a) the silane of claim 1 ; and
b) a water treatment component,
wherein said water treatment composition has an enhanced resistance to hydrolysis.
32 . The composition of claim 31 where R 1 , R 2 , R 3 , R 5 and R 6 are methyl.
33 . The composition of claim 32 where R 7 is R 8 —R A .
34 . The composition of claim 33 where R A is —SO 3 M K .
35 . The composition of claim 33 where R A is —COOM K .
36 . The composition of claim 32 where R 7 is R 9 —R C .
37 . The composition of claim 36 where R C is N(R 19 )(R 20 ).
38 . The composition of claim 32 where R 7 is R 10 —R Z .
39 . The composition of claim 38 where R Z is —N—(R 43 )(R 44 ) ␣ R 45 SO 3 (M K ) ␣ .
40 . The composition of claim 38 where R Z is —N—(R 46 )(R 47 ) □ R 48 COO(M K ) □ .
41 . A pulp and paper treatment composition comprising:
a) the silane of claim 1 ; and
b) a pulp and paper treating component,
wherein said pup and paper treatment composition has an enhanced resistance to hydrolysis.
42 . The composition of claim 41 where R 1 , R 2 , R 3 , R 5 and R 6 are methyl.
43 . The composition of claim 42 where R 7 is R 8 —R A .
44 . The composition of claim 43 where R A is —SO 3 M K .
45 . The composition of claim 43 where R A is —COOM K .
46 . The composition of claim 42 where R 7 is R 9 —R C .
47 . The composition of claim 46 where R C is N(R 19 )(R 20 ).
48 . The composition of claim 42 where R 7 is R 10 —R Z .
49 . The composition of claim 48 where R Z is —N—(R 43 )(R 44 ) ␣ R 45 SO 3 (M K ) ␣ .
50 . The composition of claim 48 where R Z is —N—(R 46 )(R 47 ) □ R 48 COO(M K ) □ .
51 . A composition comprising 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 independently selected from the group consisting of 1 to 6 monovalent hydrocarbon radicals, aryl, and a hydrocarbon group of 7 to 10 carbons containing an aryl group;
R 4 is a hydrocarbon group of 1 to 3 carbons;
R 7 is R 8 —R A , R 9 —R C , and R 10 —R Z ;
R 8 is selected from the group consisting of R 11 (O) t (R 12 ) u (O) v —,
R 14 O(C 2 H 4 O) a (C 3 H 6 O) b (C 4 H 8 O) c —;
where R 11 and R 12 are each independently selected from the group consisting of a divalent hydrocarbon group of 1 to 4 carbon atoms, that may each be optionally substituted with one or more OH radicals; R 13 is a divalent hydrocarbon group of 2 to 4 carbon atoms; R 14 is a divalent linear or branched hydrocarbon group of 1 to 6 carbons; subscripts t, u and v are zero or 1;
the subscripts a, b and c are zero or positive and satisfy the following relationships:
1 ≦a+b+c ≦10 with a≧1;
R A is a monovalent radical selected from the group consisting of —SO 3 M K ,
—C(═O)CH 2 CH(R 15 )COO-M K ; —PO 3 HM K ; —COOM K ; where R 15 is H or —SO 3 M K ;
M K is a cation selected from the group consisting of Na + , K + , Ca 2+ , NH 4 + , Li + , and monovalent ammonium ions derived from mono-, di- and trialkylamines comprising alkyl groups of 2 to 4 carbons or mono-, di- and trialkanolamines comprising alkyl groups of 2 to 4 carbons;
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 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 zero or 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 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 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 or a branched or 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 zero or 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 ) □ R 45 SO 3 (M K ) □ , —N—(R 46 )(R 47 ) □ R 48 COO(M K ) □ , —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 − ) □ ;
where R 43 , R 45 , 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 or linear monovalent hydrocarbon radical of 1 to 4 carbons, and an alkanolamine group comprising alkyl groups 2 to 4 carbons; R 45 is a divalent group of 3 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 □ is 0, 1 or 2; wherein said silane has an enhanced resistance to hydrolysis.