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
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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.
Claims135
A carbon black product having an organic group attached to the carbon black, prepared 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 A.sub.y ArNH.sub.2, in which:
- 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, NR.sub.2, SO.sub.3 H, a sulfonate salt, OSO.sub.3 H, OSO.sub.3 -- salts, NR(COR), CONR.sub.2, NO.sub.2, OPO.sub.3 H.sub.2, a monobasic or dibasic phosphate salt, PO.sub.3 H.sub.2, a monobasic or dibasic phosphonate salt, N.dbd.NR, N.sub.2.sup.+ X.sup.-, NR.sub.3.sup.+ X.sup.-, PR.sub.3.sup.+ X.sup.-, S.sub.k R, SO.sub.2 NRR', SO.sub.2 SR, SNRR', SSO.sub.3 H, a SSO.sub.3.sup.- salt, SNQ, SO.sub.2 NQ, CO.sub.2 NQ, S-(1,4-piperazinediyl)-SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl), SOR, and SO.sub.2 R;
- a linear, branched, aromatic, or cyclic hydrocarbon radical substituted with one or more of said functional groups;
- and
- an unsubstituted cyclic hydrocarbon radical;
- where R and R', which can be the same or different, are hydrogen;
- branched or unbranched C.sub.1 -C.sub.20 unsubstituted or substituted alkyl, alkenyl, or alkynyl;
- unsubstituted or substituted aryl;
- unsubstituted or substituted heteroaryl;
- unsubstituted or substituted alkylaryl;
- or unsubstituted or substituted arylalkyl;
- 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 (CH.sub.2).sub.w, (CH.sub.2).sub.x O(CH.sub.2).sub.z, (CH.sub.2).sub.x NR(CH.sub.2).sub.z, or (CH.sub.2).sub.x S(CH.sub.2).sub.z, where x is 1 to 6, z is 1 to 6, and w is 2 to 6.
A carbon black product comprising a carbon black and at least one attached organic group having a) an aromatic group and b) an acidic group having a pKa of less than 11, or a salt of an acidic group having a pKa of less than 11, or a mixture of an acidic group having a pKa of less than 11 and a salt of an acidic group having a pKa of less than 11, wherein at least one aromatic group of the organic group is directly attached to the carbon black.
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.
A carbon black product comprising a carbon black and at least one attached organic group having a) a C.sub.1 -C.sub.12 alkyl group and b) an acidic group having a pKa of less than 11, or a salt of an acidic group having a pKa of less than 11, or a mixture of an acidic group having a pKa of less than 11 and a salt of an acidic group having a pKa of less than 11, wherein the C.sub.1 -C.sub.12 alkyl group of the organic group is directly attached to the carbon black.
A carbon black product comprising a carbon black and at least one organic group Ar(CH.sub.2).sub.q S.sub.k (CH.sub.2).sub.r Ar' attached to the carbon black, wherein Ar and Ar' may be the same or different and are chosen from the group consisting of arylene and heteroarylene;
- 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 carbon black product comprising a carbon black and at least one organic group Ar(CH.sub.2).sub.q S.sub.k (CH.sub.2).sub.r Ar' 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 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 paper product comprising paper pulp and a carbon black product having at least one organic group attached to the carbon black wherein the organic group is substituted with an ionic or an ionizable group.
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(CH.sub.2).sub.q S.sub.k (CH.sub.2).sub.r Ar' attached to the carbon black, wherein Ar and Ar', which may be the same or different, are substituted or unsubstituted arylene and 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(CH.sub.2).sub.q S.sub.k (CH.sub.2).sub.r Ar' 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 carbon black product comprising a carbon black and at least one organic group ArNH.sub.2 attached to the carbon black, wherein Ar is a substituted or unsubstituted arylene.
A carbon black product comprising a carbon black and at least one organic group ArQAr'NH.sub.2, wherein Ar and Ar', which may be the same or different, are substituted or unsubstituted arylene, and Q is CH.sub.2 or SO.sub.2.
A carbon black product having an aromatic group attached to the carbon black, prepared 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 A.sub.y Ar, 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 a branched or unbranched C.sub.1 -C.sub.20 substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl;
- unsubstituted or substituted aryl;
- unsubstituted or substituted heteroaryl;
- unsubstituted or substituted alkylaryl;
- unsubstituted or substituted arylalkyl, arylene, heteroarylene, or alkylarylene;
- a functional group selected from the group consisting of OR, COR, COOR, OCOR, a carboxylate salt, CN, NR.sub.2, SO.sub.3 H, a sulfonate salt, OSO.sub.3 H, OSO.sub.3.sup.- salts, NR(COR), CONR.sub.2, NO.sub.2, OPO.sub.3 H.sub.2, a monobasic or dibasic phosphate salt, PO.sub.3 H.sub.2, a monobasic or dibasic phosphonate salt, N.dbd.NR, N.sub.2.sup.+ X.sup.-, NR.sub.3.sup.+ X.sup.-, PR.sub.3.sup.+ X.sup.-, S.sub.k R, SO.sub.2 NRR', SO.sub.2 SR, SNRR', SSO.sub.3 H, a SSO.sub.3.sup.- salt, SNQ, SO.sub.2 NQ, CO.sub.2 NQ, S-(1,4-piperazinediyl)-SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl), SOR, and SO.sub.2 R;
- and
- a linear, branched, aromatic, or cyclic hydrocarbon radical substituted with one or more of said functional groups;
- an unsubstituted cyclic hydrocarbon radical
- where R and R', which can be the same or different, are hydrogen;
- branched or unbranched C.sub.1 -C.sub.20 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.sup.- 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 (CH.sub.2).sub.w, (CH.sub.2).sub.x O(CH.sub.2).sub.z, (CH.sub.2).sub.x NR(CH.sub.2).sub.z, or (CH.sub.2).sub.x S(CH.sub.2).sub.z, where x is 1 to 6, z is 1 to 6, and w is 2 to 6.
A carbon black product having an aromatic group attached to the carbon black, prepared 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 A.sub.y Ar, 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, CN, NR.sub.2, SO.sub.3 H, a sulfonate salt, OSO.sub.3 H, OSO.sub.3.sup.- salts, NR(COR), CONR.sub.2, NO.sub.2, OPO.sub.3 H.sub.2, a monobasic or dibasic phosphate salt, PO.sub.3 H.sub.2, a monobasic or dibasic phosphonate salt, N.dbd.NR, N.sub.2.sup.+ X.sup.-, NR.sub.3.sup.+ X.sup.-, PR.sub.3.sup.+ X.sup.-, S.sub.k R, SO.sub.2 NRR', SO.sub.2 SR, SNRR', SSO.sub.3 H, a SSO.sub.3 -- salt, SNQ, SO.sub.2 NQ, CO.sub.2 NQ, S-(1,4-piperazinediyl)-SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl), SOR, and SO.sub.2 R;
- and
- a linear, branched, aromatic, or cyclic hydrocarbon radical 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 C.sub.1 -C.sub.20 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.sup.- 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 (CH.sub.2).sub.w, (CH.sub.2).sub.x O(CH.sub.2).sub.z, (CH.sub.2).sub.x NR(CH.sub.2).sub.z, or (CH.sub.2).sub.x S(CH.sub.2).sub.z, where x is 1 to 6, z is 1 to 6, and w is 2 to 6.
A process for coloring paper, comprising combining paper pulp with a carbon black having attached at least one organic group.
A paper product comprising paper pulp and a carbon black product having attached at least one organic group.
A paper product comprising paper pulp and a carbon black product having attached at least one organic group, wherein the organic group comprises a C.sub.1 -C.sub.12 alkyl group or an aromatic group.
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 A.sub.y Ar, 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, CN, NR.sub.2, SO.sub.3 H, a sulfonate salt, OSO.sub.3 H, OSO.sub.3.sup.- salts, NR(COR), CONR.sub.2, NO.sub.2, OPO.sub.3 H.sub.2, a monobasic or dibasic phosphate salt, PO.sub.3 H.sub.2, a monobasic or dibasic phosphonate salt, N.dbd.NR, N.sub.2.sup.+ X.sup.-, NR.sub.3.sup.+ X.sup.-, PR.sub.3.sup.+ X.sup.-, S.sub.k R, SO.sub.2 NRR', SO.sub.2 SR, SNRR', SSO.sub.3 H, a SSO.sub.3.sup.- salt, SNQ, SO.sub.2 NQ, CO.sub.2 NQ, S-(1,4-piperazinediyl)-SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl), SOR, and SO.sub.2 R;
- a linear, branched, aromatic, or cyclic hydrocarbon radical substituted with one or more of said functional groups;
- and
- an unsubstituted cyclic hydrocarbon radical;
- where R and R', which can be the same or different, are hydrogen;
- branched or unbranched C.sub.1 -C.sub.20 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.sup.- 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 (CH.sub.2).sub.w, (CH.sub.2).sub.x O(CH.sub.2).sub.z, (CH.sub.2).sub.x NR(CH.sub.2).sub.z, or (CH.sub.2).sub.x S(CH.sub.2).sub.z, where x is 1 to 6, z is 1 to 6, and w is 2 to 6.
A rubber composition prepared by a 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 A.sub.y Ar, 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, CN, NR.sub.2, SO.sub.3 H, a sulfonate salt, OSO.sub.3 H, OSO.sub.3 -- salts, NR(COR), CONR.sub.2, NO.sub.2, OPO.sub.3 H.sub.2, a monobasic or dibasic phosphate salt, PO.sub.3 H.sub.2, a monobasic or dibasic phosphonate salt, N.dbd.NR, N.sub.2.sup.+ X.sup.-, NR.sub.3.sup.+ X.sup.-, PR.sub.3.sup.+ X.sup.-, S.sub.k R, SO.sub.2 NRR', SO.sub.2 SR, SNRR', SSO.sub.3 H, a SSO.sub.3.sup.- salt, SNQ, SO.sub.2 NQ, CO.sub.2 NQ, S-(1,4-piperazinediyl)-SR, 2-(1,3-dithianyl), 2-(1,3-dithiolanyl), SOR, and SO.sub.2 R;
- a linear, branched, aromatic, or cyclic hydrocarbon radical substituted with one or more of said functional groups;
- and
- an unsubstituted cyclic hydrocarbon radical;
- where R and R', which can be the same or different, are hydrogen;
- branched or unbranched C.sub.1 -C.sub.20 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.sup.- 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 (CH.sub.2).sub.w, (CH.sub.2).sub.x O(CH.sub.2).sub.z, (CH.sub.2).sub.x NR(CH.sub.2).sub.z, or (CH.sub.2).sub.x S(CH.sub.2).sub.z, where x is 1 to 6, z is 1 to 6, and w is 2 to 6.
A process for coloring plastic, comprising combining a plastic with a carbon black having attached at least one organic group, wherein said organic group comprises an aromatic group or a C.sub.1 -C.sub.12 alkyl group directly attached to the carbon black.
A plastic product comprising a plastic and a carbon black product having attached at least one organic group, wherein said organic group encompasses an aromatic group or C.sub.1 -C.sub.12 alkyl group directly attached to said carbon black.
A plastic product comprising a plastic and a carbon black product having attached at least one organic group, wherein the organic group comprises a C.sub.1 -C.sub.12 alkyl group or an aromatic group, and further comprising an ionic or ionizable group.
Dependencies are inferred from the claim text.