# US 8,785,362 B2 · Triazine derivative dye transfer inhibitors, washing products containing the same and uses therefor > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,785,362 B2 - Document ID: US8785362B2 - Status: Granted - Kind: B2 - Application number: 13/430,769 - Filed: 2012-03-27 - Published: 2012-08-02 - Granted: 2014-07-22 - Earliest claimed: 2005-08-19 - Assignees: Henkel AG & Co. KGaA - Applicants: Josef Penninger; Birgit Glüsen - Inventors: Josef Penninger; Birgit Glüsen - Web page: https://patentgrep.com/patent/US8785362B2 ## CPC - C11D 3/349: {additionally containing nitrogen atoms, e.g. nitro, nitroso, amino, imino, nitrilo, nitrile groups containing compounds or their derivatives or thio urea} - C11D 3/0021: {Dye-stain or dye-transfer inhibiting compositions} - C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL ## Abstract Washing products comprising a dye transfer inhibitor selected from triazine derivatives of the general formulae T(NH—Ar(SO3Na)a)bHalc (I), X(NH-T(NH—Ar(SO3Na)a)eHalf)2 (II), X(NH-T(NH—Ar(SO3Na)d—NH-T(NH—Ar(SO3Na)a)Hal)Hal)7 (III) and combinations thereof, wherein T represents a 1,3,5-triazinyl; each Ar independently represents a naphthalene or benzene; X represents a divalent hydrocarbyl selected from linear or branched C1-20 hydrocarbon groups optionally including one or more —N(H)— carbon chain interruptions, stilbene and biphenyl groups which may optionally be mono- or poly-SO3Na-substituted; each Hal independently represents a halogen selected chlorine, bromine, and iodine; each of a and d independently represents 1, 2 or 3; b and c each represent 1 or 2 such that b+c=3; e represents 1 or 2 and f represents 0 or 1 such that e+f=2; and wherein the triazinyl substituents are located at the 2, 4 and 6 positions of the 1,3,5-triazinyl. ## Claims ### Claim 1 A washing product comprising a surfactant and a dye transfer inhibitor selected from the group consisting of triazine derivatives of the general formulae I, II, III and combinations thereof: T(NH—Ar(SO3Na)a)bHalc (I) X(NH-T(NH—Ar(SO3Na)a)eHalf)2 (II) X(NH-T(NH—Ar(SO3Na)d—NH-T(NH—Ar(SO3Na)a)Hal)Hal)2 (III) wherein the product comprises at least one triazine derivative of the general formulae II, wherein T represents a 1,3,5-triazinyl residue; each Ar independently represents a naphthalene or benzene moiety; X represents a divalent hydrocarbyl moiety selected from the group consisting of linear or branched C1-20 hydrocarbon groups which optionally may include one or more —N(H)— carbon chain interruptions, stilbene groups and biphenyl groups which optionally may be mono- or poly-SO3Na-substituted; each Hal independently represents a halogen selected from the group consisting of chlorine, bromine, and iodine; each of a and d independently represents 1, 2 or 3; b and c each represent 1 or 2 such that b+c=3; e represents 1 or 2 and f represents 0 or 1 such that e+f=2; and wherein the triazinyl residue substituents are located at the 2, 4 and 6 positions of the 1,3,5-triazinyl residue; and wherein the triazine derivative of the general formula II is prepared by a process comprising reacting two equivalents of a triazine derivative of the general formula I with one equivalent of an amino compound selected from the group consisting of C1-20 diaminoalkanes, diaminostilbenes, diaminobiphenyls, and mixtures thereof; wherein the amino compound comprises a diaminoalkane selected from the group consisting of oligo-ethyleneimines and poly-ethyleneimines of the general formula NH2—CH2CH2—(NH—CH2CH2—)nNH2, wherein n represents a number of 1 to 9. ### Claim 2 (depends on 1) The washing product of claim 1, wherein X represents a linear or branched C2-12 hydrocarbon group. ### Claim 3 (depends on 1) The washing product of claim 1, wherein the dye transfer inhibitor comprises a triazine derivative of the general formula I prepared by a process comprising reacting a 2,4,6-trihalo-1,3,5-triazine with 1 or 2 equivalents of an aminoaryl compound selected from the group consisting of 2-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid, 4-aminobenzenesulfonic acid, 2-amino-1,3-benzenedisulfonic acid, 4-amino-1,3-benzenedisulfonic acid, 2-amino-1,3,5-benzenetrisulfonic acid, 2-amino-1-naphthalenesulfonic acid, 2-amino-1,5-naphthalenedisulfonic acid, 7-amino-1,6-naphthalenedisulfonic acid, 7-amino-1,3,6-naphthalenetrisulfonic acid, and mixtures thereof, wherein the sulfonic acid groups are present in salt form. ### Claim 4 (depends on 1) The washing product of claim 1, wherein n of the general formula NH2—CH2CH2—(NH—CH2CH2—)nNH2 represents a number of 2 to 5. ### Claim 5 (depends on 1) The washing product of claim 1, wherein the amino compound comprises a sulfonic acid salt substituted diaminostilbene, a sulfonic acid salt substituted diaminobiphenyl, or mixtures thereof. ### Claim 6 (depends on 1) The washing product of claim 1, wherein the dye transfer inhibitor comprises a triazine derivative of the general formula III prepared by a process comprising reacting an amino compound selected from the group consisting of diaminostilbenes, diaminobiphenyls, and mixtures thereof with 2 equivalents of a 2,4,6-trihalo-1,3,5-triazine to form an intermediate, reacting the intermediate with a diaminoaryl compound to form a second intermediate, reacting the second intermediate with 2 equivalents of a second 2,4,6-trihalo-1,3,5-triazine to form a third intermediate, and reacting the third intermediate with 2 equivalents of an aminoaryl compound. ### Claim 7 (depends on 1) The washing product of claim 1, wherein the dye transfer inhibitor is present in an amount of 0.1 to 2 wt. %. ### Claim 8 (depends on 3) The washing product according to claim 3, wherein the dye transfer inhibitor is present in an amount of 0.1 to 2 wt. %. ### Claim 9 (depends on 6) The washing product according to claim 6, wherein the dye transfer inhibitor is present in an amount of 0.1 to 2 wt. %. ### Claim 10 (depends on 1) The washing product of claim 1, wherein the dye transfer inhibitor is present in an amount of 0.2 to 1 wt. %. ### Claim 11 (depends on 1) The washing product of claim 1, further comprising one or more polymers selected from the group consisting of vinylpyrrolidones, vinylimidazoles, vinylpyridine N-oxides, and copolymers thereof. ### Claim 12 (depends on 1) A method comprising: (a) providing a dyed textile to be washed; and (b) contacting the dyed textile with the washing product of claim 1 in an aqueous solution. ### Claim 13 (depends on 12) The method of claim 12, wherein the aqueous solution further comprises one or more surfactants. ### Claim 14 (depends on 1) The washing product of claim 1, wherein b=2 and c=1.