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US 2026/0242544 A1Published application
Silane and silicone modified antidegradants for rubber and tire
AssigneeMomentive Performance Materials Inc.
InventorsYanjun ZHU, Christopher PAPPAS, Randy Lun-Yuan FANG
Life of this patent
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Abstract
The present disclosure provides silane compounds and silicone polymers, methods of preparing the silane compounds and silicone polymers, and use of the silane compounds and silicone polymers. The present disclosure further provides use of the silane compounds and silicone polymers as antidegradants.
Claims29
A silane compound, wherein the compound is:
- (i) a phenylenediamine of Formula (I):
- wherein
- R1, R2, R3, and R4 are each independently hydrogen, 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 12 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 14 carbon atoms and optionally at least one heteroatom, or L1X1X2SiR6R7R8, wherein the heteroatom is N, O, or S;
- each R5 is independently L1X1X2SiR6R7R8;
- a is 0, 1, 2, 3, or 4;
- each L1 is independently 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, an optionally substituted aralkylene group having from 7 to 16 carbon atoms and optionally at least one heteroatom, or is absent, wherein the heteroatom is N, O, or S;
- X1 is —C(═O)—, —C(═O)—O—, —C(═O)—N—, or is absent;
- X2 is an optionally substituted alkylene group having from 1 to 20 carbon atoms and optionally at least one heteroatom, wherein the heteroatom is N, O, or S, or is absent;
- R6, R7, and R8 are each independently —OR9, —R10, or —OC(═O)R11;
- R9, R10, and R11 are each independently hydrogen, an optionally substituted alkyl group having from 1 to 6 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having from 2 to 6 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having from 3 to 6 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 14 carbon atoms and optionally at least one heteroatom, wherein the heteroatom is N, O, or S;
- and
- at least one of R1, R2, R3, R4, and R5 is L1X1X2SiR6R7R8;
- or
- (ii) a quinone diimine of Formula (II):
- wherein
- R12 and R13 are each independently hydrogen, 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 12 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 14 carbon atoms and optionally at least one heteroatom, or L2X3X4SiR15R16R17, wherein the heteroatom is N, O, or S;
- each R14 is independently L2X3X4SiR15R16R17;
- b is 0, 1, 2, 3, or 4;
- each L2 is independently 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 12 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, an optionally substituted aralkylene group having from 7 to 16 carbon atoms and optionally at least one heteroatom, or is absent, wherein the heteroatom is N, O, or S;
- X3 is —C(═O)—, —C(═O)—O—, —C(═O)—N—, or is absent;
- X4 is an optionally substituted alkylene group having from 1 to 20 carbon atoms and optionally at least one heteroatom, wherein the heteroatom is N, O, or S, or is absent;
- R15, R16, and R17 are each independently —OR18, —R19, or —OC(═O)R20;
- R18, R19, and R20 are each independently hydrogen, an optionally substituted alkyl group having from 1 to 6 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having from 2 to 6 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having from 3 to 6 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 14 carbon atoms and optionally at least one heteroatom, wherein the heteroatom is N, O, or S;
- and
- at least one of R12, R13, and R14 is L2X3X4SiR15R16R17;
- or
- (iii) a phenylenediamine of Formula (III):
- wherein
- R21, R22, R23, and R24 are each independently hydrogen, 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 12 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 14 carbon atoms and optionally at least one heteroatom, wherein the heteroatom is N, O, or S;
- each L3 is independently 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, an optionally substituted aralkylene group having from 7 to 16 carbon atoms and optionally at least one heteroatom, or is absent, wherein the heteroatom is N, O, or S;
- R25 and R26 are each independently —OR27, —R28, or —OC(═O)R29;
- and
- R27, R28, and R29 are each independently hydrogen, an optionally substituted alkyl group having from 1 to 6 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having from 2 to 6 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having from 3 to 6 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 14 carbon atoms and optionally at least one heteroatom, wherein the heteroatom is N, O, or S.
30 more elements
(canceled)
(canceled)
(canceled)
(canceled)
(canceled)
A polymer represented by Formula (IX):
- wherein
- R30, R31, and R32 are each independently hydrogen, 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 12 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 14 carbon atoms and optionally at least one heteroatom, wherein the heteroatom is N, O, or S;
- each L4 is independently 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, an optionally substituted aralkylene group having from 7 to 16 carbon atoms and optionally at least one heteroatom, or is absent, wherein the heteroatom is N, O, or S;
- X5 is —C(═O)—, —C(═O)—O—, —C(═O)—N—, or is absent;
- X6 is an optionally substituted alkylene group having from 1 to 20 carbon atoms and optionally at least one heteroatom, wherein the heteroatom is N, O, or S, or is absent;
- R33, R34, and R35 are each independently —OR36, —R37, or —OC(═O)R38;
- and
- R36, R37, and R38 are each independently hydrogen, an optionally substituted alkyl group having from 1 to 6 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having from 2 to 6 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having from 3 to 6 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 14 carbon atoms and optionally at least one heteroatom, wherein the heteroatom is N, O, or S;
- and
- f is an integer from 1 to 60.
7 more elements
-25. (canceled)
-28. (canceled)
-32. (canceled)
Dependencies are inferred from the claim text.