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.
Claims59
A carbon black product having an organic group attached to the carbon black, 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′, 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, 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).
A carbon black product, having an aromatic group attached to the carbon black, 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′, 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, 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).
A carbon black product comprising 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 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, OPO2H2, 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, 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).
A carbon black product comprising 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.
A carbon black product comprising a carbon black and at least one organic group ArOH attached to the carbon black, wherein Ar is arylene or heteroarylene.
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′ are arylene, k is an integer from 1 to 8, and q and r are 0.
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′ are heteroarylene, k is an integer from 1 to 8, and q and r are 0.
A process for preparing a carbon black product having an organic group attached to the carbon black comprising the step of:
- reacting at least one diazonium salt with a carbon black in a protic reaction medium,
- wherein the diazonium salt is generated in situ from the primary amine H2NArSkArNH2 wherein Ar is benzothiazolylene and k is 2.
A carbon black product having attached to the carbon black an aliphatic group, which is substituted by a functional group selected from the group consisting of OR, COR, COOR, OCOR, COOLi, COONa, COOK, COO−NR4+, halogen, NR2, SO3H, sulfonate salts, OSO3H, OSO3−salts, NR(COR), CONR2, NO2, PO3H2 phosphonate salts, phosphate salts, NR3+X−, PR3+X−, SkR, SSO3H, SSO3− salts, SO2NRR′ SO2SR, SNRR′, SNQ, SO2NQ, CO2NQ, S-(1,4-piperazinediyl)-SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl), SOR and SO2R;
- wherein R and R′, which are 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)x, wherein x is 1 to 6, z is 1 to 6 and w is 2 to 6.
A carbon black product having attached to the carbon black a cyclic group selected from cyclic organic groups, alicyclic hydrocarbon groups and heterocyclic hydrocarbon groups, which is substituted by a functional group selected from the group consisting of R, OR, COR, COOR, OCOR, carboxylate salts, halogen, CN, NR2, SO3H, sulfonate salts, OSO3H, OSO3− salts, NR(COR), CONR2, NO2, PO3H2, phosphonate salts, phosphate salts, N═NR, NR3+X−, PR3+X−, SkR, SSO3H, SSO3− salts, SO2NRR′, SO2SR, SNRR′, SNQ, SO2NQ, CO2NQ, S-(1,4-piperazinediyl)-SR, 2-(1,3-dithianyl), 2-(1,2-dithiolanyl), SOR and SO2R;
- wherein R and R′, which are 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.
Dependencies are inferred from the claim text.