Copolymers of epoxy compounds and amino silanes
View Patent ↗The present invention provides for a composition comprising the reaction product of a. an oxirane or oxetane compound comprising at least two oxirane or oxetane groups; and b. an amino silane having the formula: N(H)(R 1 )R 2 Si(OR 3 )3-a-b-c(OR 4 )a(R 5 Si(OR 6 )d(R 7 )e) b Rc with R 1 is chosen from the group consisting of H or a monovalent hydrocarbon radical containing one to 20 carbon atoms; R 2 and R 5 are independently selected from a group consisting of oxygen or a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons; R 4 is a hydrocarbon radical that contains 3 to 200 carbon atoms; R 3 , R 6 , R 7 , and R 8 and are each independently selected from the group of monovalent linear or branched hydrocarbon radicals having from 1 to 200 carbon atoms; the subscript b is zero or a positive number and has a value ranging from 0 to 3; the subscripts a, and c are zero or positive and have a value ranging from 0 to 3 subject to the limitation that (a+b+c)≦3; the subscripts d and e are zero or positive and have a value ranging from 0 to 3 subject to the limitation that (d+e)≦3.
1. A textile treated with a composition comprising the reaction product of
a) an oxirane or oxetane compound comprising at least two oxirane or oxetane groups; and
b) an amino silane having the formula:
N(H)(R 1 )R 2 Si(OR 3 ) 3-a-b-c (OR 4 ) a (R 5 Si(OR 6 ) d (R 7 ) e ) b R 8 c
with R 1 is chosen from the group consisting of H or a monovalent hydrocarbon radical containing one to 20 carbon atoms;
R 2 is selected from a group consisting of a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons;
R 4 is a hydrocarbon radical that contains 3 to 200 carbon atoms;
R 5 is selected from a group consisting of oxygen or a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons;
R 3 , R 6 , R 7 , and R 8 and are each independently selected from the group of monovalent linear or branched hydrocarbon radicals having from 1 to 200 carbon atoms;
a positive number and has a value ranging from 0 to 3;
the subscripts a, and c are zero and b is equal to 3;
the subscripts d and e are zero or positive and have a value ranging from 0 to 3 subject to the limitation that (d+e) is equal to 3, wherein said textile has an enhanced response to water.
2. The composition of claim 1 where the oxirane or oxetane compound is selected from the group consisting of siloxanes, hydrocarbons and polyethers.
3. The composition of claim 2 where the oxirane or oxetane compound is a siloxane having the formula:
M f M E h M PE i M H j D k D E l D PE m D H n T o T E p T PE q T H r Q s with
M=R 9 R 10 R 11 SiO 1/2 ;
M H =R 12 R 13 H SiO 1/2 ;
M PE =R 12 R 13 (—CH 2 CH(R 14 )(R 15 ) t O(R 16 ) u (C 2 H 4 O) v (C 3 H 6 O) w (C 4 H 8 O) x R 17 )SiO 1/2 ;
M E =R 12 R 13 (R E )SiO 1/2
D=R 18 R 19 SiO 2/2 ; and
D H =R 20 HSiO 2/2
D PE =R 20 (—CH 2 CH(R 14 )(R 15 ) t O(R 16 ) u (C 2 H 4 O) v (C 3 H 6 O) w(C 4 H 8 O) x R 17 )SiO 2/2
D E =R 20 R E SiO 2/2 ;
T=R 21 SiO 3/2 ;
T H =HSiO 3/2 ;
T PE =(—CH 2 CH(R 14 )(R 15 ) t O(R 16 ) u (C 2 H 4 O) v (C 3 H 6 O) w (C 4 H 8 O) x R 17 )SiO 3/2 ;
T E =R E SiO 3/2 ; and
Q=SiO 4/2 ;
where R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 60 carbon atoms;
R 14 is H or a 1 to 6 carbon atom alkyl group; R 15 is a divalent alkyl radical of 1 to 6 carbons; R 16 is selected from the group of divalent radicals consisting of —C 2 H 4 O—, —C 3 H 6 O—, and —C 4 H 8 O—; R 17 is selected from the group consisting of H, monofunctional hydrocarbon radicals of 1 to 6 carbons, and acetyl;
R E is independently a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from one to sixty carbon atoms;
the subscript f may be zero or positive subject to the limitation that when the subscript f is zero, h must be positive;
the subscript h is zero or positive subject to the limitations that when h is zero, the subscript f is positive, and that the sum of the subscripts h, l and p is positive;
the subscript k is zero or positive and has a value ranging from about 0 to about 1,000;
the subscript l is zero or positive and has a value ranging from about 0 to about 400 subject to the limitation that the sum of the subscripts h, l and p is positive;
the subscript o is zero or positive and has a value ranging from 0 to about 50;
the subscript p is zero or positive and has a value ranging from 0 to about 30 subject to the limitation that the sum of the subscripts h, l and p is positive;
the subscript s is zero or positive and has a value ranging from 0 to about 20;
the subscript i is zero or positive and has a value ranging from 0 to about 20;
the subscript m is zero or positive and has a value ranging from 0 to about 200;
the subscript q is zero or positive and has a value ranging from 0 to about 30;
the subscript j is zero or positive and has a value ranging from 0 to about 2;
the subscript n is zero or positive and has a value ranging from 0 to about 20;
the subscript r is zero or positive and has a value ranging from 0 to about 30;
the subscript t is zero or one;
the subscript u is zero or one;
the subscript v is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v+w+x)>0;
the subscript w is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v+w+x)>0;
the subscript x is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v+w+x)>0.
4. The reaction product of claim 3 further comprising the reaction product of the aminosilane and a compound having the formula:
R 29 (R 30 ) κ Si(OR 31 ) 3-η-θ (R 32 ) η (OR 33 ) θ
where R 29 is a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from 3 to 12 carbon atoms;
R 30 is a divalent hydrocarbon radical consisting of 1-60 carbons and the subscript κ has a value of zero or 1; R 31 and R 32 are independently selected from the group of monovalent linear or branched hydrocarbon radicals having from 1 to 60 carbon atoms;
the subscript η is zero or positive and has a value ranging from 0 to 3;
the subscript θ is greater than 0 and less than or equal to 3, subject to the limitation that 3-η-θ is greater than or equal to zero;
R 33 is a hydrocarbon radical that contains 3 to 200 carbon atoms.
5. The reaction product of claim 3 wherein
R 1 has from one to ten carbon atoms;
R 2 has from one to ten carbon atoms;
R 4 has from three to ten carbon atoms;
R 3 , R 6 , R 7 , and R 8 each independently have from one to twenty carbon atoms;
R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 each independently have from one to four carbon atoms;
the subscripts f, l, m, n, o, p, q, r, each independently range from 0 to 200;
the subscript k ranges from 0-500;
the subscripts v, w, and x each independently range from 0 to 50.
6. The reaction product of claim 3 wherein
R 1 has from one to five carbon atoms;
R 2 has from two to eight carbon atoms;
R 4 has from three to eight carbon atoms;
R 3 , R 6 , R 7 , and R 8 each independently have from one to fifteen carbon atoms;
R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 each independently have from one to three carbon atoms;
the subscripts f, l, m, n, o, p, q, r, each independently range from 0 to 100;
the subscript k ranges from 5-250;
the subscripts v, w, and x each independently range from 0 to 35.
7. The reaction product of claim 3 wherein
R 1 is hydrogen;
R 2 has from two to five carbon atoms;
R 4 has from three to five carbon atoms;
R 3 , R 6 , R 7 , and R 8 each independently have from two to eight carbon atoms;
R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 each independently methyl;
the subscripts f, l, m, n, o, p, q, r, each independently range from 0 to 50;
the subscript k ranges from 5 to 150;
the subscripts v, w, and x each independently range from 0 to 25.
8. The reaction product of claim 4 wherein
R 1 has from one to ten carbon atoms;
R 2 has from one to ten carbon atoms;
R 4 has from three to ten carbon atoms;
R 3 , R 6 , R 7 , and R 8 each independently have from one to twenty carbon atoms;
R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 each independently have from one to four carbon atoms;
the subscripts f, l, m, n, o, p, q, r, each independently range from 0 to 200;
the subscript k ranges from 0-500;
the subscripts v, w, and x each independently range from 0 to 50;
R 31 and 32 each independently have from one to ten carbon atoms and R 33 has from three to one hundred carbon atoms.
9. Method of treating a textile, comprising the steps of
(i) applying to the textile, a composition comprising the reaction product of
c) an oxirane or oxetane compound comprising at least two oxirane or oxetane groups wherein the oxirane or oxetane compound is selected from the group consisting of siloxanes, hydrocarbons and polyethers; and
d) an amino silane having the formula:
N(H)(R 1 )R 2 Si(OR 3 ) 3-a-b-c (OR 4 ) a (R 5 Si(OR 6 ) d (R 7 ) e ) b R 8 c
with
R 1 is chosen from the group consisting of H or a monovalent hydrocarbon radical containing one to 20 carbon atoms;
R 2 is selected from a group consisting of a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons;
R 4 is a hydrocarbon radical that contains 3 to 200 carbon atoms;
R 5 is selected from a group consisting of oxygen or a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons;
R 3 , R 6 , R 7 , and R 8 and are each independently selected from the group of monovalent linear or branched hydrocarbon radicals having from 1 to 200 carbon atoms;
the subscripts a, and c are zero, and b is equal to 3
the subscripts d and e are zero or positive and have a value ranging from 0 to 3 subject to the limitation that (d+e) is equal to 3, wherein said textile has an enhanced response to water, and
(ii) curing.
10. The method of claim 9 where the oxirane or oxetane compound is a siloxane having the formula:
M f M E h M PE i M H j D k D E l D PE m D H n T o T E p T PE q T H r Q s with
M=R 9 R 10 R 11 SiO 1/2 ;
M H =R 12 R 13 H SiO 1/2 ;
M PE =R 12 R 13 (—CH 2 CH(R 14 )(R 15 ) t O(R 16 ) u (C 2 H 4 O) v (C 3 H 6 O) w (C 4 H 8 O) x R 17 )SiO 1/2 ;
M E =R 12 R 13 (R E )SiO 1/2
D=R 18 R 19 SiO 2/2 ; and
D H =R 20 HSiO 2/2
D PE =R 20 (—CH 2 CH(R 14 )(R 15 ) t O(R 16 ) u (C 2 H 4 O) v (C 3 H 6 O) w(C 4 H 8 O) x R 17 )SiO 2/2
D E =R 20 R E SiO 2/2 ;
T=R 21 SiO 3/2 ;
T H =HSiO 3/2 ;
T PE =(—CH 2 CH(R 14 )(R 15 ) t O(R 16 ) u (C 2 H 4 O) v (C 3 H 6 O) w (C 4 H 8 O) x R 17 )SiO 3/2 ;
T E =R E SiO 3/2 ; and
Q=SiO 4/2 ;
where R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 60 carbon atoms;
R 14 is H or a 1 to 6 carbon atom alkyl group; R 15 is a divalent alkyl radical of 1 to 6 carbons; R 16 is selected from the group of divalent radicals consisting of —C 2 H 4 O—, —C 3 H 6 O- , and —C 4 H 8 O—; R 17 is selected from the group consisting of H, monofunctional hydrocarbon radicals of 1 to 6 carbons, and acetyl;
R E is independently a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from one to sixty carbon atoms;
the subscript f may be zero or positive subject to the limitation that when the subscript f is zero, h must be positive;
the subscript h is zero or positive subject to the limitations that when h is zero, the subscript f is positive, and that the sum of the subscripts h, l and p is positive;
the subscript k is zero or positive and has a value ranging from about 0 to about 1,000;
the subscript l is zero or positive and has a value ranging from about 0 to about 400 subject to the limitation that the sum of the subscripts h, l and p is positive;
the subscript o is zero or positive and has a value ranging from 0 to about 50;
the subscript p is zero or positive and has a value ranging from 0 to about 30 subject to the limitation that the sum of the subscripts h, l and p is positive;
the subscript s is zero or positive and has a value ranging from 0 to about 20;
the subscript i is zero or positive and has a value ranging from 0 to about 20;
the subscript m is zero or positive and has a value ranging from 0 to about 200;
the subscript q is zero or positive and has a value ranging from 0 to about 30;
the subscript j is zero or positive and has a value ranging from 0 to about 2;
the subscript n is zero or positive and has a value ranging from 0 to about 20;
the subscript r is zero or positive and has a value ranging from 0 to about 30;
the subscript t is zero or one;
the subscript u is zero or one;
the subscript v is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v+w+x)>0;
the subscript w is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v+w +x) >0;
the subscript x is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v+w +x) >0.