IP Library › Patent Application 18169523

Patent Application

App. No. 18/169,523

SYNTHESIS OF SILANE COMPOUNDS

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Patent No.: US None
App. No.: 18/169,523

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Abstract

The present disclosures are directed to a silane coupling agent, two silane functional polymers, a method of making a silane coupling agent, the use of a silane coupling agent for making a silane functional polymer, a method of making a silane functional polymer by removing a protecting group, and a composition comprising one or more silane functional polymers.

Claims (197)

1 . A silane compound having formula (I)

wherein:

M is selected from the group consisting of nitrogen, sulfur and oxygen;

Y is a protecting group;

Q 1 is -L-Si—(X 1 ) d (X 2 ) 3-d or R 1 ;

each L is independently absent, an optionally substituted alkylene group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenylene group having from 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkylene group having from 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted arylene group having from 6 to 12 carbon atoms and optionally at least one heteroatom, or an optionally substituted aralkylene group having from 7 to 16 carbon atoms and optionally at least one heteroatom;

each X 1 is independently —OR 1 or —OC(═O)R 1 ;

each X 2 is R 1 ;

each R 1 is independently selected from the group consisting of an optionally substituted alkyl group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having from 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkynyl group having from 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having from 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted aryl group having from 6 to 12 carbon atoms and optionally at least one heteroatom, an optionally substituted aralkyl group having from 7 to 16 carbon atoms and optionally at least one heteroatom, and an optionally substituted cyclic silane; or is a divalent group formed from two R 1 groups being bonded together through a covalent bond, with the proviso that if two R 1 groups are bonded together then b is 2 or 3;

a is 0 or 1; with the proviso that if M is nitrogen, a is 1 or if M is sulfur or oxygen, a is 0;

b is 1, 2, or 3; and

d is 0, 1, 2, or 3.

2 . The silane compound of claim 1 , wherein Y is

3 . The silane compound of claim 1 , wherein each X 1 is —OR 1 .

4 . The silane compound of claim 1 , wherein each R 1 is an optionally substituted alkyl group having from 1 to 20 carbon atoms.

5 . The silane compound of claim 1 , wherein

(a) when M is nitrogen, a is 1, and Y is

the silane compound of formula (I) is

(b) when Q 1 is -L-Si—(X 1 ) d (X 2 ) 3-d and Y is

the silane compound of formula (I) is

6 . The silane compound of claim 1 , wherein the silane compound of formula (I) is

7 . A polymer represented by:

(a) formula (II)

wherein:

M is selected from the group consisting of nitrogen, sulfur and oxygen;

Y is a protecting group;

Q 2 is -L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d or R 1 ;

each X 1 is independently —OR 1 or —OC(═O)R 1 ;

each X 2 is R 1 ;

G is a polymer fragment having a backbone of carbon atoms covalently bonded together by C—C single bond, C—C double bond or a combination of C—C single bonds and C—C double bonds;

a is 0 or 1; with the proviso that if M is nitrogen, a is 1 or if M is sulfur or oxygen, a is 0;

b is 1, 2, or 3;

c is 1, 2, or 3, with the proviso that c is equal to or less than b;

d is 0, 1, 2, or 3; and

e is 0, 1, 2, or 3, with the proviso that e is equal to or less than d; or

(b) formula (III)

wherein

M is selected from the group consisting of nitrogen, sulfur and oxygen;

Q 2 is -L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d or R 1 ;

each X 1 is independently —OR 1 or —OC(═O)R 1 ;

each X 2 is R 1 ;

G is a polymer fragment having a backbone of carbon atoms covalently bonded together by C—C single bond, C—C double bond or a combination of C—C single bonds and C—C double bonds;

a is 0 or 1; with the proviso that if M is nitrogen, a is 1 or if M is sulfur or oxygen, a is 0;

b is 1, 2, or 3;

c is 1, 2, or 3, with the proviso that c is equal to or less than b;

d is 0, 1, 2, or 3; and

e is 0, 1, 2, or 3, with the proviso that e is equal to or less than d.

8 . The polymer of claim 7 , wherein Y in formula (II) is selected from the group consisting of

and further wherein:

each R 2 is independently selected from the group consisting of an optionally substituted alkyl group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having from 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having from 3 to 14 carbon atoms and optionally at least one heteroatom, an optionally substituted aryl group having from 6 to 16 carbon atoms and optionally at least one heteroatom, and an optionally substituted aralkyl group having from 7 to 20 carbon atoms and optionally at least one heteroatom.

9 . The polymer of claim 7 , wherein each L is an optionally substituted alkylene group having from 1 to 20 carbon atoms.

10 . The polymer of claim 7 , wherein each X 1 is —OR 1 .

11 . The polymer of claim 7 , wherein each R 1 is an optionally substituted alkyl group having from 1 to 20 carbon atoms.

12 . The polymer of claim 7 , wherein

(a) when M is nitrogen, a is 1, and Y is

the polymer of formula (II) is

(b) when M is nitrogen, a is 1, Q 2 is -L-Si-(G) e (X) d-e (X 2 ) 3-d and Y is

the polymer of formula (II) is

(d) when M is nitrogen and a is 1, the polymer of formula (III) is

(e) when M is nitrogen, a is 1, and Q 2 is -L-Si-(G) e (X) d-e (X 2 ) 3-d , the polymer of formula (III) is

13 . The polymer of claim 7 , wherein

(a) the polymer of formula (II) is

(b) the polymer of formula (III) is

14 . The polymer of claim 7 , wherein G is a polymer fragment of formula (IV)

wherein:

each R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 is independently an alkyl group having from 1 to 20 carbon atoms, or hydrogen;

each R 6 is independently selected from the group consisting of hydrogen, an alkyl group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an alkenyl group having from 2 to 20 carbon atoms, a cycloalkyl group having from 3 to 14 carbon atoms, a cycloalkenyl group having from 4 to 14 carbon atoms, an aryl group having from 6 to 16 carbon atoms, and an aralkyl group having from 7 to 20 carbon atoms; and

f, g and h are integers, wherein f is equal to or greater than 0, g is equal to or greater than 0, and h is equal to or greater than 0, with the proviso that the sum of f, g and h is equal to or greater than 1.

15 . The polymer of claim 7 , wherein the polymer fragment G is styrene butadiene polymer.

16 . A method of making the silane compound of formula (I)

of claim 1 , comprising:

reacting a compound of formula (V)

with a protective agent; wherein:

M is selected from the group consisting of nitrogen, sulfur and oxygen;

Y is a protecting group;

Q 1 is -L-Si—(X 1 ) d (X 2 ) 3-d or R 1 ;

each X 1 is independently —OR 1 or —OC(═O)R 1 ;

each X 2 is R 1 ;

a is 0 or 1; with the proviso that if M is nitrogen, a is 1 or if M is sulfur or oxygen, a is 0;

b is 1, 2, or 3; and

d is 0, 1, 2, or 3.

17 . The method of claim 16 , wherein the protective agent is selected from the group consisting of

and further wherein:

X is halogen or OR 2 ; and

18 . The method of claim 16 , wherein

(a) when M is nitrogen, a is 1, and Y is

the silane compound of formula (I) is

and is prepared by reacting the compound of formula (V)

with the protective agent

(b) when M is nitrogen, a is 1, and Y is

and Q 1 is -L-Si—(X 1 ) d (X 2 ) 3-d , the silane compound of formula (I) is

and is prepared by reacting the compound of formula (V)

with the protective agent

Q 1 is -L-Si—(X 1 ) d (X 2 ) 3-d , L is —CH 2 CH 2 CH 2 —, X 1 is —OR 1 , and R 1 is —CH 2 CH 3 , the silane compound of formula (I) is

and is prepared by reacting the compound of formula (V)

with the protective agent

(d) when M is nitrogen, a is 1, Y is

and Q 1 is R 1 , the silane compound of formula (I) is

and is prepared by reacting the compound of formula (V)

with the protective agent

(e) when M is sulfur, a is 0, and Y is

the silane compound of formula (I) is

and is prepared by reacting the compound of formula (V)

with the protective agent

19 . A method of making the polymer of claim 7 , wherein the polymer is represented by formula (II)

and is prepared by

(i) reacting a chain of C—C unsaturated carbon atom monomers with an anionic initiator to form a polymer fragment G; and

(ii) reacting the polymer fragment G with a silane compound of formula (I)

wherein:

M is selected from the group consisting of nitrogen, sulfur and oxygen;

Y is a protecting group;

Q 1 is -L-Si—(X) d (X 2 ) 3-d or R 1 ;

Q 2 is -L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d or R 1 ; with the proviso that if Q 1 is -L-Si—(X) d (X 2 ) 3-d , Q 2 is -L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d ; and if Q 1 is R 1 , Q 2 is R 1 ;

each X 1 is independently —OR 1 or —OC(═O)R 1 ;

each X 2 is R 1 ;

each R 1 is independently selected from the group consisting of an optionally substituted alkyl group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having from 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkynyl group having from 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having from 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted aryl group having from 6 to 12 carbon atoms and optionally at least one heteroatom, and an optionally substituted aralkyl group having from 7 to 16 carbon atoms and optionally at least one heteroatom;

a is 0 or 1; with the proviso that if M is nitrogen, a is 1 or if M is sulfur or oxygen, a is 0;

b is 1, 2, or 3;

c is 1, 2, or 3, with the proviso that c is equal to or less than b;

d is 0, 1, 2, or 3; and

e is 0, 1, 2, or 3, with the proviso that e is equal to or less than d.

20 . The method of claim 19 , wherein

(a) when M is nitrogen, a is 1, and Y is

the polymer of formula (II) is

and is prepared by reacting the polymer fragment G with the silane compound of formula (I)

(b) when M is nitrogen, a is 1, Y is

and Q 2 is -L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d , the polymer of formula (II) is

and is prepared by reacting the polymer fragment G with the silane compound of formula (I)

Q 2 is -L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d , d is 3, L is —CH 2 CH 2 CH 2 —, e is 1, X 1 is —OR 1 , and R 1 is —CH 2 CH 3 , the polymer of formula (II) is

and is prepared by reacting the polymer fragment G with the silane compound of formula (I)

(d) when M is nitrogen, a is 1, Y is

and Q 2 is R 1 , the polymer of formula (II) is

and is prepared by reacting the polymer fragment G with the silane compound of formula (I)

(e) when M is sulfur, Y is

and a is 0, the polymer of formula (II) is

and is prepared by reacting the polymer fragment G with the silane compound of formula (I)

21 . The method of claim 19 , wherein the anionic initiator is n-butyllithium.

22 . A method of making the polymer of claim 7 , wherein the polymer is represented by formula (III)

comprising reacting a polymer of formula (II)

with an acid, a base, or heat, wherein:

M is selected from the group consisting of nitrogen, sulfur and oxygen;

Y is a protecting group;

Q 2 is -L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d or R 1 ;

each X 1 is independently —OR 1 or —OC(═O)R 1 ;

each X 2 is R 1 ;

each R 1 is independently selected from the group consisting of an optionally substituted alkyl group having from 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having from 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkynyl group having from 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having from 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted aryl group having from 6 to 12 carbon atoms and optionally at least one heteroatom, and an optionally substituted aralkyl group having from 7 to 16 carbon atoms and optionally at least one heteroatom;

G is a polymer fragment having a backbone of carbon atoms covalently bonded together by C—C single bond, C—C double bond or a combination of C—C single bonds and C—C double bonds;

a is 0 or 1; with the proviso that if M is nitrogen, a is 1 or if M is sulfur or oxygen, a is 0;

b is 1, 2, or 3;

c is 1, 2, or 3, with the proviso that c is equal to or less than b;

d is 0, 1, 2, or 3; and

e is 0, 1, 2, or 3, with the proviso that e is equal to or less than d.

23 . The method of claim 22 , wherein

(a) when M is nitrogen and a is 1, the polymer of formula (III) is

and is prepared by reacting the polymer of formula (II)

in the presence of an acid, a base, or heat; or

(b) when M is nitrogen, a is 1, and Q 2 is -L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d , the polymer of formula (III) is

and is prepared by reacting the polymer of formula (II)

in the presence of an acid, a base, or heat; or

Q 2 is -L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d , d is 3, L is —CH 2 CH 2 CH 2 —, e is 1, b is 3, X 1 is —OR 1 , and R 1 is —CH 2 CH 3 , the polymer of formula (III) is

and is prepared by reacting the polymer of formula (II)

in the presence of an acid, a base, or heat; or

(d) when M is nitrogen, a is 1, and Q 2 is R 1 , the polymer of formula (III) is

and is prepared by reacting the polymer of formula (II)

in the presence of an acid, a base, or heat.

24 . A rubber composition comprising one or more polymers of claim 7 .

25 . Use of the polymer of claim 7 in a rubber composition.

Assignments (6)

RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025

From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT

To: MOMENTIVE PERFORMANCE MATERIALS INC.

Reel/Frame 073168/0715 →