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US 2026/0176383 A1Published application
Antiozonant compositions and methods
OwnerWilliam M Hart-Cooper, Elliot C. Rossomme +3inventors
InventorsWilliam M Hart-Cooper, Elliot C. Rossomme, Colleen M McMahan, Anh Tran, William J. Orts
Life of this patent
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Abstract
Compositions and methods of making and using the compositions are described exemplifying compounds formed from amine-functionalized indoles and other amines for uses such as rubber antiozonants.
Claims44
A method of treating a rubber polymer to protect it against damage by ozone comprising, treating the polymer with an effective amount of a composition comprising a compound of formula:
- wherein A1 is
- n-butyl, sec-butyl, iso-butyl, tert-butyl groups or a monocyclic heteroaryl group each of which is optionally substituted by one or more of R1, R2, R3, R4, R5, R6,
- wherein, A2 and A3 are independently selected from
- a) hydrogen;
- b) a saturated or unsaturated aliphatic group optionally substituted with one or more unsubstituted or substituted alkyl groups or aryl groups or an imine functional group bearing an A1, A2 or A3 substituent;
- c) a monocyclic or polycyclic aryl or heteroaryl group optionally substituted with C1 to C20 straight or branched chain saturated alkyl, unsaturated alkyls, F, Cl, Br, I, NO2, OH, NR7R8, acyl, alkyl ether or aryl ether substituents or an imine functional group bearing an A1, A2 or A3 substituent;
- wherein the aryl substituents are optionally substituted with one or more F, Cl, Br, I, NO2, OH, NR7R8, acyl, alkyl ether or aryl ether substituents;
- wherein R1, R2, R3, R4, R5, R6 are independently selected from H, alkyl, unsaturated alkyl, F, Cl, Br, I, NO2, OH, amino, acyl, alkyl ether or aryl ether, monocyclic or polycyclic aryl or heteroaryl group;
- and wherein R7, R8 are H or alkyl.
6 more elements
A method of treating a rubber polymer to protect it from degradation by ozone by treating it with an effective amount of at least one compound selected from the group comprising of:
- or mixtures thereof wherein the composition comprises cis or trans isomers of CN imine bond(s) or a mixture of the isomers.
A rubber polymer formulation comprising an antiozonant compound of formula:
- Wherein A1 is
- n-butyl, sec-butyl, iso-butyl, tert-butyl groups or a monocyclic heteroaryl group each of which is optionally substituted by one or more of R1, R2, R3, R4, R5, R6,
- wherein, A2 and A3 are independently selected from a) hydrogen;
- b) a saturated or unsaturated aliphatic group optionally substituted with one or more unsubstituted or substituted alkyl groups or aryl groups or an imine functional group bearing A1, A2 or A3 substituents;
- c) a monocyclic or polycyclic aryl or heteroaryl group optionally substituted with C1 to C20 straight or branched chain saturated alkyl, unsaturated alkyls, F, Cl, Br, I, NO2, OH, NR7R8, acyl, alkyl ether or aryl ether substituents or an imine functional group bearing an A1, A2 or A3 substituent;
- wherein the aryl substituents are optionally substituted with one or more F, Cl, Br, I, NO2, OH, N R7R8, acyl, alkyl ether or aryl ether substituents;
- and wherein R1, R2, R3, R4, R5, R6 are independently selected from H, alkyl, unsaturated alkyl, F, Cl, Br, I, NO2, OH, amino, acyl, alkyl ether or aryl ether, monocyclic or polycyclic aryl or heteroaryl group;
- and wherein R7, R8 are H or alkyl.
5 more elements
A composition comprising a compound of formula:
- wherein A1 is
- n-butyl, sec-butyl, iso-butyl, tert-butyl groups or a monocyclic heteroaryl group optionally substituted by one or more of R1, R2, R3, R4, R5, R6,
- wherein, A2 and A3 are independently selected from a) hydrogen;
- b) a saturated or unsaturated aliphatic group optionally substituted with one or more unsubstituted or substituted alkyl groups or aryl groups or an imine functional group bearing A1, A2 or A3 substituents;
- c) a monocyclic or polycyclic aryl or heteroaryl group optionally substituted with C1 to C20 straight or branched chain saturated alkyl, unsaturated alkyls, F, Cl, Br, I, NO2, OH, NR7R8, acyl, alkyl ether or aryl ether substituents or an imine functional group bearing an A1, A2 or A3 substituent;
- wherein the aryl substituents are optionally substituted with one or more F, Cl, Br, I, NO2, OH, N R7R8, acyl, alkyl ether or aryl ether substituents;
- wherein R1, R2, R3, R4, R5, R6 are independently selected from H, alkyl, unsaturated alkyl, F, Cl, Br, I, NO2, OH, amino, acyl, alkyl ether or aryl ether, monocyclic or polycyclic aryl or heteroaryl group;
- and wherein R7, R8 are H or alkyl.
5 more elements
A composition comprising a compound of formula:
- wherein A1 is
- n-butyl, sec-butyl, iso-butyl, tert-butyl groups or a monocyclic heteroaryl group optionally substituted by one or more of R1, R2, R3, R4, R5, R6,
- wherein, A2 and A3 are independently selected from
- a) hydrogen;
- b)
- wherein R1, R2, R3, R4, R5, R6, R9 are independently selected from H, alkyl, unsaturated alkyl, F, Cl, Br, I, NO2, OH, amino, acyl, alkyl ether or aryl ether, monocyclic or polycyclic aryl or heteroaryl group;
- and wherein R7, R8 are H or alkyl,
- wherein A4 is hydrogen or CHA2A3.
5 more elements
A composition comprising a compound of formula:
- wherein A1 is
- n-butyl, sec-butyl, iso-butyl, tert-butyl groups or a monocyclic heteroaryl group optionally substituted by one or more of R1, R2, R3, R4, R5, R6,
- wherein, A2 is independently selected from
- a) hydrogen;
- b) a saturated or unsaturated aliphatic group optionally substituted with one or more unsubstituted or substituted alkyl groups or aryl groups or an imine functional group bearing an A1, A2 or A3 substituent;
- c) a monocyclic or polycyclic aryl or heteroaryl group optionally substituted with C1 to C20 straight or branched chain saturated alkyl, unsaturated alkyls, F, Cl, Br, I, NO2, OH, NR7R8, acyl, alkyl ether or aryl ether substituents or an imine functional group bearing an A1, A2 or A3 substituent;
- wherein the aryl substituents are optionally substituted with one or more F, Cl, Br, I, NO2, OH, N R7R8, acyl, alkyl ether or aryl ether substituents;
- wherein R1, R2, R3, R4, R5, R6, R9 are independently selected from H, alkyl, unsaturated alkyl, F, Cl, Br, I, NO2, OH, amino, acyl, alkyl ether or aryl ether, monocyclic or polycyclic aryl or heteroaryl group;
- and wherein R7, R8 are H or alkyl,
- wherein at least one R10, R11, R12, R13, R14 is a CHA2(NA1A4) group, and the remaining are independently selected from H, alkyl, unsaturated alkyl, F, Cl, Br, I, NO2, OH, amino, acyl, alkyl ether or aryl ether, monocyclic or polycyclic aryl or heteroaryl, group;
- and wherein R7, R8 are H or alkyl,
- wherein A4 is hydrogen or CHA2A3.
9 more elements
A method of treating a rubber polymer to protect it against damage by ozone comprising, treating the polymer with an effective amount of a composition comprising a compound of formula:
- wherein A1 is
- n-butyl, sec-butyl, iso-butyl, tert-butyl groups or a monocyclic heteroaryl group optionally substituted by one or more of R1, R2, R3, R4, R5, R6,
- wherein, A2 and A3 are independently selected from
- a) hydrogen;
- b)
- wherein R1, R2, R3, R4, R5, R6, R9 are independently selected from H, alkyl, unsaturated alkyl, F, Cl, Br, I, NO2, OH, amino, acyl, alkyl ether or aryl ether, monocyclic or polycyclic aryl or heteroaryl group;
- and wherein R7, R8 are H or alkyl,
- wherein A4 is hydrogen or CHA2A3.
5 more elements
A method of treating a rubber polymer to protect it against damage by ozone comprising, treating the polymer with an effective amount of a composition comprising a compound of formula:
- wherein A1 is
- n-butyl, sec-butyl, iso-butyl, tert-butyl groups or a monocyclic heteroaryl group optionally substituted by one or more of R1, R2, R3, R4, R5, R6,
- wherein, A2 is independently selected from
- a) hydrogen;
- b) a saturated or unsaturated aliphatic group optionally substituted with one or more unsubstituted or substituted alkyl groups or aryl groups or an imine functional group bearing an A1, A2 or A3 substituent;
- c) a monocyclic or polycyclic aryl or heteroaryl group optionally substituted with C1 to C20 straight or branched chain saturated alkyl, unsaturated alkyls, F, Cl, Br, I, NO2, OH, NR7R8, acyl, alkyl ether or aryl ether substituents or an imine functional group bearing an A1, A2 or A3 substituent;
- wherein the aryl substituents are optionally substituted with one or more F, Cl, Br, I, NO2, OH, N R7R8, acyl, alkyl ether or aryl ether substituents;
- wherein R1, R2, R3, R4, R5, R6, R9 are independently selected from H, alkyl, unsaturated alkyl, F, Cl, Br, I, NO2, OH, amino, acyl, alkyl ether or aryl ether, monocyclic or polycyclic aryl or heteroaryl group;
- and wherein R7, R8 are H or alkyl,
- wherein at least one R10, R11, R12, R13, R14 is a CHA2(NA1A4) group, and the remaining are independently selected from H, alkyl, unsaturated alkyl, F, Cl, Br, I, NO2, OH, amino, acyl, alkyl ether or aryl ether, monocyclic or polycyclic aryl or heteroaryl, group;
- and wherein R7, R8 are H or alkyl,
- wherein A4 is hydrogen or CHA2A3.
9 more elements
Dependencies are inferred from the claim text.