Reaction of carbon black with diazonium salts, resultant carbon black products and their uses
AssigneeCabot Corporation
InventorsJames A. Belmont, Robert M. Amici, Collin P. Galloway
Life of this patent
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Abstract
Processes for preparing a carbon black product having an organic group attached to the carbon black. In one process at least one diazonium salt reacts with a carbon black in the absence of an externally applied electric current sufficient to reduce the diazonium salt. In another process at least one diazonium salt reacts with a carbon black in a protic reaction medium. Carbon black products which may be prepared according to process of the invention are described as well as uses of such carbon black products in plastic compositions, rubber compositions, paper compositions, and textile compositions.
Claims177
A rubber composition prepared by the process comprising mixing rubber and a carbon black product comprising a carbon black and at least one organic group Ar(CH2)qSk(CH2)rAr′ attached to the carbon black, wherein Ar and Ar′, which may be the same or different, are substituted or unsubstituted arylene or heteroarylene groups;
- k is an integer from 1 to 8;
- q is an integer from 0 to 4;
- and r is an integer from 0 to 4.
A rubber composition prepared by the process comprising mixing rubber and a carbon black product comprising carbon black and at least one organic group Ar(CH2)qSk(CH2)rAr′ attached to the carbon black, wherein Ar is an arylene or a heteroarylene;
- Ar′ is an aryl or a heteroaryl;
- k is an integer from 1 to 8;
- q is an integer from 0 to 4;
- and r is an integer from 0 to 4.
A rubber composition prepared by the process comprising mixing rubber and a carbon black product comprising a carbon black and at least one organic group ArSH attached to the carbon black, wherein Ar is an arylene or a heteroarylene.
A rubber composition prepared by the process comprising mixing rubber and a carbon black product having at least one organic group attached to the carbon black, wherein the organic group is AyAr, wherein:
- Ar is an aromatic or heteroaromatic radical;
- A, which can be the same or different when y is greater than 1, is independently a substituent on the aromatic radical selected from:
- a functional group selected from the group consisting of OR, COR, COOR, OCOR, a carboxylate salt, halogen, CN, NR2, SO3H, a sulfonate salt, OSO3H, OSO3— salts, NR(COR), CONR2, NO2, OPO3H2, a monobasic or dibasic phosphate salt, PO3H2, a monobasic or dibasic phosphonate salt, N═NR, N2+X−, NR3+X−, PR3+X−, SkR, SO2NRR′, SO2SR, SNRR′, SSO3H, a SSO3− salt, SNQ, SO2NQ, CO2NQ, S—(1,4-piperazinediyl)—SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl), SOR, and SO2R;
- and
- a linear, branched or cyclic hydrocarbon radical, unsubstituted or substituted with one or more of said functional groups;
- where R and R′, which can be the same or different, are hydrogen;
- branched or unbranched C1-C20 unsubstituted or substituted alkyl, alkenyl, or alkynyl;
- unsubstituted or substituted aryl;
- unsubstituted or substituted heteroaryl;
- unsubstituted or substituted alkylaryl;
- unsubstituted or substituted arylalkyl, arylene, heteroarylene, or alkylarylene;
- wherein
- k is an integer from 1 to 8;
- X− is a halide or an anion derived from a mineral or organic acid;
- y is an integer from 1 to the total number of —CH radicals present in the aromatic radical;
- and
- Q is (CH2)w, (CH2)xO(CH2)z, (CH2)xNR(CH2)z, or (CH2)xS(CH2)z, where x is 1 to 6, z is 1 to 6, and w is 2 to 6, wherein said Ar is directly attached to the carbon black.
An elastomeric composition comprising at least one elastomer and at least one modified carbon black product comprising a carbon black and at least one organic group attached to the carbon black, wherein said at least one organic group comprises an aromatic group or a C1-C12 alkyl group directly attached to said carbon black.
A method of decreasing the tan delta max at 70° C. of an elastomeric composition, said method comprising combining said elastomeric composition with at least one modified carbon black product to form an improved elastomeric composition, said carbon black product comprising a carbon black and at least one organic group attached to the carbon black, wherein said organic group comprises an aromatic group which is directly attached to the carbon black.
A method of increasing the abrasion resistance of an elastomeric composition, said method comprising combining said elastomeric composition with at least one modified carbon black product to form an improved elastomeric composition, said carbon black product comprising a carbon black and at least one organic group attached to the carbon black, wherein said organic group comprises an aromatic group which is directly attached to the carbon black.
An elastomeric composition obtained by mixing at least one elastomer and a carbon black product having an organic group attached to the carbon black, wherein said carbon black product is obtained by a process comprising the step of reacting at least one diazonium salt with a carbon black in a protic reaction medium, wherein said diazonium salt is generated in situ from a primary amine, the protic medium is an aqueous medium, and the primary amine is an amine of the formula AyArNH2, in which:
- Ar is an aromatic or heteroaromatic radical;
- y is an integer from 1 to the total number of —CH radicals present in the aromatic radical;
- and
- A, which can be the same or different when y is greater than 1, is independently a substituent on the aromatic radical selected from:
- a functional group selected from the group consisting of a branched or unbranched C1-C20 substituted alkyl, branched or unbranched C3-C20 unsubstituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted alkylaryl, and unsubstituted or substituted arylalkyl;
- a functional group selected from the group consisting of OR, COR, COOR, OCOR, a carboxylate salt, CN, NR2, SO3H, a sulfonate salt, OSO3H, OSO3— salts, NR(COR), CONR2, NO2, OPO3H2, a monobasic or dibasic phosphate salt, PO3H2, a monobasic or dibasic phosphonate salt, N═NR, N2+X−, NR3+X−, PR3+X−, SkR, SO2NRR′, SSO3H, a SSO3− salt, SNQ, SO2NQ, CO2NQ, S—(1,4-piperazinediyl)—SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl), SOR, and SO2R;
- and
- a linear, branched, aromatic, or cyclic hydrocarbon radical, substituted with one or more of said functional groups and/or halogen(s);
- wherein R and R′, which can be the same or different, are hydrogen;
- branched or unbranched C1-C20 unsubstituted or substituted alkyl, alkenyl, or alkynyl;
- unsubstituted or substituted aryl;
- unsubstituted or substituted heteroaryl;
- unsubstituted or substituted alkylaryl;
- or unsubstituted or substituted arylalkyl;
- k is an integer from 1 to 8;
- X− is a halide or an anion derived from a mineral or organic acid;
- and Q is (CH2)w, (CH2)xO(CH2)z, (CH2)xNR(CH2)z or (CH2)xS(CH2)z, wherein x is 1 to 6, z is 1 to 6, and w is 2 to 6;
- and wherein Ar is optionally further substituted with alkyl(s) and/or halogen(s), wherein said Ar is directly attached to the carbon black.
An elastomeric composition obtained by mixing at least one elastomer and a carbon black product having an organic group attached to the carbon black, wherein said carbon black product is obtained by a process comprising the step of reacting at least one diazonium salt with a carbon black in a protic reaction medium, wherein said aromatic group is a group of the formula AyAr, in which:
- Ar is an aromatic or heteroaromatic radical;
- y is an integer from 1 to the total number of —CH radicals present in the aromatic radical;
- and
- A, which can be the same or different when y is greater than 1, is independently a substituent on the aromatic radical selected from:
- a functional group selected from the group consisting of a branched or unbranched C1-C20 substituted alkyl, branched or unbranched C3-C20 unsubstituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted alkylaryl, and unsubstituted or substituted arylalkyl;
- a functional group selected from the group consisting of OR, COR, COOR, OCOR, a carboxylate salt, CN, NR2, SO3H, a sulfonate salt, OSO3H, OSO3— salts, NR(COR), CONR2, NO2, OPO3H2, a monobasic or dibasic phosphate salt, PO3H2, a monobasic or dibasic phosphonate salt, N═NR, N2+X−, NR3+X−, PR3+X−, SkR, SO2NRR′, SSO3H, a SSO3− salt, SNQ, SO2NQ, CO2NQ, S—(1,4-piperazinediyl)—SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl), SOR, and SO2R;
- and
- a linear, branched, aromatic, or cyclic hydrocarbon radical, substituted with one or more of said functional groups and/or halogen(s);
- wherein R and R′, which can be the same or different, are hydrogen;
- branched or unbranched C1-C20 unsubstituted or substituted alkyl, alkenyl, or alkynyl;
- unsubstituted or substituted aryl;
- unsubstituted or substituted heteroaryl;
- unsubstituted or substituted alkylaryl;
- or unsubstituted or substituted arylalkyl;
- k is an integer from 1 to 8;
- X− is a halide or an anion derived from a mineral or organic acid;
- and Q is (CH2)w, (CH2)xO(CH2)z, (CH2)xNR(CH2)z or (CH2)xS(CH2)z, wherein x is 1 to 6, z is 1 to 6, and w is 2 to 6;
- and wherein Ar is optionally further substituted with alkyl(s) and/or halogen(s), wherein said Ar is directly attached to the carbon black.
An elastomeric composition obtained by mixing at least one elastomer and a carbon black product, wherein said carbon black product is comprised of a carbon black and at least one organic group having an organic group attached to the carbon black, wherein said carbon black product is organic group attached to the carbon black, wherein the organic group is an aromatic group of the formula AyAr, wherein:
- Ar is an aromatic or heteroaromatic radical;
- y is an integer from 1 to the total number of —CH radicals present in the aromatic radical;
- and
- A, which can be the same or different when y is greater than 1, is independently a substituent on the aromatic radical selected from:
- a functional group selected from the group consisting of a branched or unbranched C1-C20 substituted alkyl, branched or unbranched C3-C20 unsubstituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted heteroaryl, unsubstituted or substituted alkylaryl, and unsubstituted or substituted arylalkyl;
- a functional group selected from the group consisting of OR, COR, COOR, OCOR, a carboxylate salt, CN, NR2, SO3H, a sulfonate salt, OSO3H, OSO3— salts, NR(COR), CONR2, NO2, OPO3H2, a monobasic or dibasic phosphate salt, PO3H2, a monobasic or dibasic phosphonate salt, N═NR, N2+X−, NR3+X−, PR3+X−, SkR, SO2NRR′, SSO3H, a SSO3− salt, SNQ, SO2NQ, CO2NQ, S—(1,4-piperazinediyl)—SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl), SOR, and SO2R;
- and
- a linear, branched, aromatic, or cyclic hydrocarbon radical, substituted with one or more of said functional groups and/or halogen(s);
- wherein R and R′, which can be the same or different, are hydrogen;
- branched or unbranched C1-C20 unsubstituted or substituted alkyl, alkenyl, or alkynyl;
- unsubstituted or substituted aryl;
- unsubstituted or substituted heteroaryl;
- unsubstituted or substituted alkylaryl;
- or unsubstituted or substituted arylalkyl;
- k is an integer from 1 to 8;
- X− is a halide or an anion derived from a mineral or organic acid;
- and Q is (CH2)w, (CH2)xO(CH2)z, (CH2)xNR(CH2)z or (CH2)xS(CH2)z, wherein x is 1 to 6, z is 1 to 6, and w is 2 to 6;
- and wherein Ar is optionally further substituted with alkyl(s) and/or halogen(s).
An elastomeric composition obtained by mixing at least one elastomer and a carbon black product, wherein said carbon black product is comprised of a carbon black and at least one organic group attached to the carbon black, wherein the organic group is an aromatic group of the formula AyAr, wherein:
- Ar is an aromatic radical selected from the group consisting of phenyl, naphthyl anthryl, phenanthryl, biphenyl, and pyridyl;
- y is an integer from 1 to the total number of —CH radicals present in the aromatic radical;
- and
- A, which can be the same or different when y is greater than 1, is independently a substituent on the aromatic radical selected from:
- a functional group selected from the group consisting of OR, COR, COOR, OCOR, COOLi, COONa, COOK, COO−NR4+, CN, NR2, SO3H, SO3Li, SO3Na, SO3K, SO3−NR4+, NR(COR), CONR2, NO2, PO3H2, PO3HNa, PO3Na2, N═NR, N2+X−, NR3+X−, PR3+X−, SkR, SOR, and SO2R;
- and
- a linear, branched, aromatic, or cyclic hydrocarbon radical, substituted with one or more of said functional groups;
- wherein R and R′, which can be the same or different, are hydrogen;
- branched or unbranched C1-C20 unsubstituted or substituted alkyl, alkenyl, or alkynyl;
- unsubstituted or substituted aryl;
- unsubstituted or substituted heteroaryl;
- unsubstituted or substituted alkylaryl;
- or unsubstituted or substituted arylalkyl;
- k is an integer from 1 to 8;
- X− is a halide or an anion derived from a mineral or organic acid.
An elastomeric composition obtained by mixing at least one elastomer and a carbon black product, wherein said carbon black product is comprised of a carbon black and at least one organic group attached to the carbon black, wherein the organic group is an aromatic group of the formula AyAr, wherein:
- Ar is an aromatic radical selected from the group consisting of phenyl, benzothiazolyl, and benzothiadiazolyl;
- y is an integer from 1 to the total number of —CH radicals present in the aromatic radical;
- and
- A, which can be the same or different when y is greater than 1, is independently a substituent on the aromatic radical selected from:
- a functional group selected from the group consisting of SkR, SSO3H, SO2NRR′, SO2SR, SNRR′, SNQ, SO2NQ, CO2NQ, S—(1,4-piperazinediyl)—SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl);
- and
- a linear, branched, aromatic, or cyclic hydrocarbon radical, substituted with one or more of said functional groups;
- wherein R and R′, which can be the same or different, are hydrogen;
- branched or unbranched C1-C20 unsubstituted or substituted alkyl, alkenyl, or alkynyl;
- unsubstituted or substituted aryl;
- unsubstituted or substituted heteroaryl;
- unsubstituted or substituted alkylaryl;
- or unsubstituted or substituted arylalkyl;
- k is an integer from 1 to 8;
- and Q is (CH2)w, (CH2)xO(CH2)z, (CH2)xNR(CH2)z or (CH2)xS(CH2)z, wherein X is 1 to 6, z is 1 to 6, and w is 2 to 6.
An elastomeric composition obtained by mixing at least one elastomer and a carbon black product, wherein said carbon black product is comprised of a carbon black and at least one organic group having a) an aromatic group and b) a cationic group, wherein at least one aromatic group of the organic group is attached to the carbon black and wherein the organic group is a N-substituted pyridinium group.
An elastomeric composition obtained by mixing at least one elastomer and a carbon black product, wherein said carbon black product is comprised of a carbon black and at least one organic group ArOH attached to the carbon black, wherein Ar is arylene or heteroarylene.
An elastomeric composition obtained by mixing at least one elastomer and a carbon black product, wherein said carbon black product is comprised of a carbon black and at least one organic group Ar(CH2)qSk(CH2)rAr′ attached to the carbon black, wherein Ar and Ar′ are arylene or heteroarylene, k is an integer from 1 to 8, and q and r are 0.
Dependencies are inferred from the claim text.