IP Library › Patent Application 14261590

Patent Application

App. No. 14/261,590

COPOLYMERS OF EPOXY COMPOUNDS AND AMINO SILANES

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Patent No.: US None
App. No.: 14/261,590

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Abstract

A composition includes a non-crosslinked reaction product of an oxirane or oxetane compound (I) comprising at least two oxirane or oxetane groups; a compound (II) comprising silicon and one or more amino groups; and optionally a polyamine (III); and a secondary amine (IV).

Claims (237)

1 . A composition comprising the non-crosslinked reaction product of

I) an oxirane or oxetane compound (I) comprising at least two oxirane or oxetane groups:

II) a compound (II) comprising silicon and one or more amino groups; and optionally

III) a polyamine (III); and optionally

IV) a secondary amine (IV).

2 . The composition of claim 1 wherein the oxirane or oxetane compound (I) is selected from the group consisting of siloxanes, silanes, hydrocarbons and polyethers particularly where the oxirane or oxetane compound is a siloxane having the formula:

M′ a M′ E b M′ PE c M′ H d D′ e D′ E f D′ PE g D′ H h T′ i T′ E j T′ PE k T′ H l Q′ m (1)

with

M′=R 41 R 42 R 43 SiO 1/2 ;

M′ H =R 41 R 42 H SiO 1/2 ;

M′ PE =R 41 R 42 (—CH 2 CH(R 44 )(R 45 ) n O(C 2 H 4 O) o (C 3 H 6 O) p (C 4 H 8 O) q R 46 )SiO 1/2 ;

M′ E =R 41 R 42 (R′ E )SiO 1/2 ;

D′=R 41 R 42 SiO 2/2 ; and

D′ H =R 41 HSiO 2/2 ;

D′ PE =R 41 (—CH 2 CH(R 4 )(R 45 ) n O(C 2 H 4 O) o (C 3 H 6 O) p (C 4 H 8 O) q R 46 )SiO 2/2 ;

D′ E =R 41 R′ E SiO 2/2 ;

T′=R 41 SiO 3/2 ;

T′ H =HSiO 3/2 ;

T′ PE =(—CH 2 CH(R 44 )(R 45 ) n O(C 2 H 4 O) o (C 3 H 6 O) p (C 4 H 8 O) q R 46 )SiO 3/2 ;

T′ E =R′ E SiO 3/2 ; and

Q′=SiO 4/2 ;

where R 41 , R 42 and R 43 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to about 60 carbon atoms;

R 44 is H or a 1 to about 6 carbon atom containing alkyl group;

R 45 is a divalent hydrocarbon radical of 1 to about 6 carbons;

R 46 is H, a monofunctional hydrocarbon radical of 1 to about 6 carbons, or acetyl;

R′ E is independently a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from about two to about sixty carbon atoms subject to the limitation that the oxirane or oxetane compound (I) contains at least two oxirane or oxetane groups;

the subscript a is 0 to about 20, 1 to about 20, preferably 0 to about 10, and more preferably 0 to about 5;

the subscript b is 0 to about 20, 1 to about 20, preferably 0 to about 10, and more preferably 0 to about 3 subject to the limitation that (b+f+j)>0;

the subscript e is 0 to about 1,000, 1 to about 1000, preferably 0 to about 500, and more preferably 0 to about 200;

the subscript f is 0 to about 400, 1 to about 400, preferably 0 to about 100, and more preferably 0 to about 20 subject to the limitation that (b+f+j)>0;

the subscript i is 0 to about 50, 1 to about 50, preferably 0 to about 10, and more preferably 0 to about 5;

the subscript j is 0 to about 30, 1 to about 30, preferably 0 to about 10, and more preferably 0 to about 5 subject to the limitation that (b+f+j)>0;

the subscript m is 0 to about 20, 1 to about 20, preferably 0 to about 10, and more preferably 0 to about 7.5;

the subscript c is 0 to about 20, 1 to about 20, preferably 0 to about 15, and more preferably 0 to about 10;

the subscript g is 0 to about 200, 1 to about 200, preferably 0 to about 100, and more preferably 0 to about 50;

the subscript k is 0 to about 30, 1 to about 30, preferably 0 to about 20, and more preferably 0 to about 10;

the subscript d is 0 to about 20, 1 to about 20, preferably 0 to about 10, and more preferably 0 to about 3;

the subscript h is 0 to about 20, 1 to about 20, preferably 0 to about 10, and more preferably 0 to about 3;

the subscript l is 0 to about 30, 1 to about 30, preferably 0 to about 10, and more preferably 0 to about 3;

the subscript n is zero or one;

the subscript o is 0 to about 1(O), 1 to about 100, subject to the limitation that (o+p+q)>0;

the subscript p is 0 to about 100, 1 to about 100, subject to the limitation that (o+p+q)>0;

the subscript q is 0 to about 100, 1 to about 100, subject to the limitation that (o+p+q)>0.

3 . The composition of claim 1 wherein the oxirane or oxetane compound (I) has the formula:

(R 7 ) r (R 48 ) s (R 49 ) t (R 50 ) u (2)

where R 47 and R 50 are independently a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from about 2 to about 12 carbon atoms;

R 48 and R 49 are each selected from the group consisting of H or a linear or branched monovalent hydrocarbon radical of 1 to about 200 carbons; optionally substituted with nitrogen, sulphur and oxygen;

the subscripts r, s, t, u are zero or positive ranging from zero to about 10 subject to the limitation that (r+u)≧2.

4 . The composition of claim 1 wherein the oxirane or oxetane compound (I) is a polyether having the formula:

R 52 O(C 2 H 4 O) w (C 3 H 6 O) x (C 4 H 8 O) y R 53 (3)

where R 52 and R 53 are independently a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from about 2 to about 12 carbon atoms;

the subscript w is 0 to about 100, 1 to about 100, subject to the limitation that (w+x+y)>0;

the subscript x is 0 to about 100, 1 to about 100, subject to the limitation that (w+x+y)>0;

the subscript y is 0 to about 100, 1 to about 100, subject to the limitation that (w+x+y)>0.

5 . The composition of claim 1 wherein compound (II) comprises silicon and one or more amino groups selected from the group consisting of siloxanes and silanes having the formula:

M″ aa M″ A bb M″ PE cc M″ H dd M″ M ee D″ ff D″ A gg D″ PE hh D″ H ii T″ jj T″ A kk T″ PE ll T″ H mm Q″ nn (4)

with

M″=R 55 R 56 R 57 SiO 1/2 ;

M″ H =R 55 R 56 H SiO 1/2 ;

M″ PE =R 55 R 56 (—CH 2 CH(R 58 )(R 59 ) oo (C 2 H 4 O) pp (C 3 H 6 O) qq (C 4 H 8 O) rr R 60 )SiO 1/2 ;

M″ A =R 55 R 56 (R″ A )SiO 1/2 ;

M″ M =R 55 R 56 R 57 R″ A Si;

D″=R 55 R 56 SiO 2/2 ;

D″ H =R 55 HSiO 2/2 ;

D″ PE =R 55 (—CH 2 CH(R 58 )(R 59 ) oo O(C 2 H 4 O) pp (C 3 H 6 O) qq (C 4 H 8 O) rr R 60 )SiO 2/2 ;

D″ A =R 55 R″ A SiO 2/2 ;

T″=R 55 SiO 3/2 ;

T″ H =HSiO 3/2 ;

T″ PE =(—CH 2 CH(R 58 )(R 59 ) oo O(C 2 H 4 O) pp (C 3 H 6 O) qq (C 4 H 8 O) rr R 60 )SiO 3/2 ;

T″ A =R″ A SiO 3/2 ; and

Q″=SiO 4/2 ;

where R 55 , R 56 and R 57 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to about 60 carbon atoms;

R 58 is H or a 1 to about 6 carbon atom alkyl group;

R 59 is a divalent hydrocarbon radical of 1 to about 6 carbons;

R 60 is selected from the group consisting of H, monofunctional hydrocarbon radicals of 1 to about 6 carbons, and acetyl;

R″ A is independently a monovalent hydrocarbon radical containing one or more amino moieties having from one to about sixty carbon atoms;

the subscript aa is 0 to about 20, 1 to about 20, preferably 0 to about 10, and more preferably 0 to about 5;

the subscript bb is 0 to about 20, 1 to about 20, preferably 0 to about 10, and more preferably 0 to about 5 subject to the limitations that the sum of the subscripts bb, ee, gg and kk is greater than zero;

the subscript ee is zero or 1 subject to the limitation that when ee is 1 then all the subscripts aa, bb, cc, dd, ff, gg, hh, ii, jj, kk, ll, mm and nn are zero;

the subscript ff is 0 to about 1,000, 1 to about 1000, preferably 0 to about 500, and more preferably 0 to about 200;

the subscript gg is 0 to about 400, 1 to about 400, preferably 0 to about 100, and more preferably 0 to about 20 subject to the limitation that the sum of the subscripts bb, ee, gg and kk is greater than zero;

the subscript jj is 0 to about 50, 1 to about 50, preferably 0 to about 30, and more preferably 0 to about 10;

the subscript kk is 0 to about 30, 1 to about 30, preferably 0 to about 10, and more preferably 0 to about 5 subject to the limitation that the sum of the subscripts bb, gg and kk is greater than 1;

the subscript nn is 0 to about 20, 1 to about 20, preferably 0 to about 10, and more preferably 0 to about 5;

the subscript cc is 0 to about 20, 1 to about 20, preferably 0 to about 10, and more preferably 0 to about 5;

the subscript hh is 0 to about 200, 1 to about 200, preferably 0 to about 100, and more preferably 0 to about 50;

the subscript ll is 0 to about 30, 1 to about 30, preferably 0 to about 20, and more preferably 0 to about 5;

the subscript dd is 0 to about 2;

the subscript ii is 0 to about 20, 1 to about 20, preferably 0 to about 15, and more preferably 0 to about 5;

the subscript mm is 0 to about 30, 1 to about 30, preferably 0 to about 20, and more preferably 0 to about 5;

the subscript oo is zero or one;

the subscript pp is 0 to about 100, 1 to about 100, subject to the limitation that (pp+qq+rr)>0;

the subscript qq is 0 to about 100, 1 to about 100, subject to the limitation that (pp+qq+rr)>0;

the subscript rr is 0 to about 100, 1 to about 100, subject to the limitation that (pp+qq+rr)>0.

6 . The composition of claim 1 wherein compound II has 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 (5)

wherein

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 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.

7 . The composition of claim 1 wherein compound (I) and compound (II) are reacted in the presence of polyamine compound (III) to produce said reaction product, said polyamine compound (III) having the formula:

N(R 21 )(R 22 )A[N(R 23 )(R 24 )] zz ,

where

R 21 , R 22 , R 23 and R 24 are independently chosen from the group consisting of H or a monovalent hydrocarbon radical having 1 to about 20 carbon atoms;

A is selected from a group consisting of a divalent linear or branched hydrocarbon radical having 1 to about 60 carbons or a divalent polydialkyl-siloxane radical, optionally containing S, O or N; and subscript zz is 1 to about 20.

8 . The composition of claim 1 comprising a non-crosslinked reaction product of a polyepoxy-compound with an aminosilane free of alkoxy groups or an aminosilicone having the formula:

wherein R is a divalent organic or silicone group and R′ is a monovalent alkyl or siloxane and x is about 2 to about 1000.

9 . The composition of claim 1 wherein the reaction product has the following formula:

wherein X is about 5 to about 30 and Y is about 2 to about 100.

10 . The composition of claim 1 wherein the reaction product comprises reaction product of an epoxy compound, an amino silane, and a compound having the formula (7):

R 29 (R 30 ) κ Si(OR 31 ) 3−η−θ (R 32 ) η (OR 33 ) θ (7)

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.

11 . A composition comprising the non-crosslinked reaction product of

I) an oxirane or oxetane compound (I) comprising at least two oxirane or oxetane groups;

II) a compound (II) comprising silicon and one or more amino groups;

III) a polyamine (III); and optionally

IV) a secondary amine (IV).

12 . The composition of claim 11 wherein the oxirane or oxetane compound (I) is selected from the group consisting of siloxanes, silanes, hydrocarbons and polyethers particularly where the oxirane or oxetane compound is a siloxane having the formula:

M′ a M′ E b M′ PE c M′ H d D′ e D′ E f D′ PE g D′ H h T′ i T′ E j T′ PE k T′ H l Q′ m (1)

with

M′=R 41 R 42 R 43 SiO 1/2 ;

M′ H =R 41 R 42 H SiO 1/2 ;

M′ PE =R 41 R 42 (—CH 2 CH(R 44 )(R 45 ) n O(C 2 H 4 O) o (C 3 H 6 O) p (C 4 H 8 O) q R 46 )SiO 1/2 ;

M′ E =R 41 R 42 (R′ E )SiO 1/2 ;

D′=R 41 R 42 SiO 2/2 ; and

D′ H =R 41 HSiO 2/2 ;

D′ PE =R 41 (—CH 2 CH(R 4 )(R 45 ) n O(C 2 H 4 O) o (C 3 H 6 O) p (C 4 H 8 O) q R 46 )SiO 2/2 ;

D′ E =R 41 R′ E SiO 2/2 ;

T′=R 41 SiO 3/2 ;

T′ H =HSiO 3/2 ;

T′ PE =(—CH 2 CH(R 44 )(R 45 ) n O(C 2 H 4 O) o (C 3 H 6 O) p (C 4 H 8 O) q R 46 )SiO 3/2 ;

T′ E =R′ E SiO 3/2 ; and

Q′=SiO 4/2 ;

where R 41 , R 42 and R 43 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to about 60 carbon atoms;

R 44 is 1H or a 1 to about 6 carbon atom containing alkyl group;