# US 10,870,819 B2 · Leuco colorants as bluing agents in laundry care compositions

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,870,819 B2
- Document ID: US10870819B2
- Status: Granted
- Kind: B2
- Application number: 16/157,131
- Filed: 2018-10-11
- Published: 2019-04-18
- Granted: 2020-12-22
- Earliest claimed: 2017-10-12
- Assignees: The Procter & Gamble Company
- Applicants: The Procter & Gamble Company
- Inventors: Gregory Scot Miracle; Brian Joseph Loughnane; Samantha Jo Cost; Wesley A. Freund; Haihu Qin; Sanjeev Kumar Dey
- Web page: https://patentgrep.com/patent/US10870819B2

## CPC

- C11D 3/42: Brightening agents {; Blueing agents}
- C09B 11/12: without any OH group bound to an aryl nucleus
- C11D 3/0084: {Antioxidants; Free-radical scavengers}
- C11D 3/2034: {aromatic}
- C11D 3/30: Amines; Substituted amines {; Quaternized amines}
- C11D 3/40: Dyes {; Pigments}
- C11D 7/261: {Alcohols; Phenols}
- C11D 7/3209: {Amines or imines with one to four nitrogen atoms; Quaternized amines}
- C11D 7/3218: {Alkanolamines or alkanolimines}
- C11D 2111/12: Soft surfaces, e.g. textile
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

A laundry care composition including at least one laundry care ingredient, a leuco composition, from 0.05 wt % to 15 wt % of a primary amine compound and from 0.005 wt % to 5 wt % of an antioxidant.

## Claims

### Claim 1

A laundry care composition comprising: (a) at least one laundry care ingredient, (b) a leuco composition; (c) from 0.05 wt % to 15 wt % of a primary amine compound and (d) from 0.005 wt % to 5 wt % of an antioxidant, wherein the leuco composition is uncolored and undergoes color change only when contacted with a triggering agent, wherein the leuco composition comprises at least one unsubstituted phenyl ring.

### Claim 2 (depends on 1)

The laundry care composition of claim 1, wherein the antioxidant comprises at least one hindered phenol.

### Claim 3 (depends on 1)

The laundry care composition of claim 1, wherein the mole ratio of the primary amine to the antioxidant is less than 5,000:1.0.

### Claim 4 (depends on 3)

The laundry care composition of claim 3, wherein the primary amine has a molecular weight of less than 1000 g/mole.

### Claim 5 (depends on 1)

The laundry care composition of claim 1, wherein the leuco composition comprises a compound selected from the group consisting of a diarylmethane leuco, a triarylmethane leuco, an oxazine leuco, a thiazine leuco, a hydroquinone leuco, an arylaminophenol leuco and mixtures thereof.

### Claim 6 (depends on 5)

The laundry care composition of claim 5, wherein the leuco compound is selected from one or more compounds selected from the group consisting of:
(f) mixtures thereof;
wherein the ratio of Formula I-V to its oxidized form is at least 1:3; wherein each individual Ro, Rm and Rp group on each of rings A, B and C is independently selected from the group consisting of hydrogen, deuterium and R5; wherein each R5 is independently selected from the group consisting of halogens, nitro, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, —(CH2)n—O—R1, —C(O)R1, —C(O)OR1, —C(O)O−, —C(O)NR1R2, —OC(O)R1, —OC(O)OR1, —OC(O)NR1R2, —S(O)2R1, —S(O)2OR1, —S(O)2O−, —S(O)2NR1R2, —NR1C(O)R2, —NR1C(O)OR2, —NR1C(O)SR2, —NR1C(O)NR2R3, —NR1R2, —P(O)2R1, —P(O)(OR1)2, —P(O)(OR1)O−, and —P(O)(O−)2; wherein the index n is an integer from 0 to 4; wherein at least one of the Ro and Rm groups on at least one of the three rings A, B or C is hydrogen; each Rp is independently selected from hydrogen, —OR1 and —NR1R2;
wherein G is independently selected from the group consisting of hydrogen, deuterium, C1-C16 alkoxide, phenoxide, bisphenoxide, nitrite, nitrile, alkyl amine, imidazole, arylamine, polyalkylene oxide, halides, alkylsulfide, aryl sulfide, and phosphine oxide;
wherein R1, R2 and R3 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and R4; R4 is an organic group composed of one or more organic monomers with said monomer molecular weights ranging from 28 to 500;
wherein e and f are independently integers from 0 to 4;
wherein each R20 and R21 is independently selected from the group consisting of a halogen, a nitro group, alkyl groups, substituted alkyl groups, —NC(O)OR1, —NC(O)SR1, —OR1, and —NR1R2;
wherein each R25 is independently selected from the group consisting of a monosaccharide moiety, a disaccharide moiety, an oligosaccharide moiety, a polysaccharide moiety, —C(O)R1, —C(O)OR1, —C(O)NR1R2;
wherein each R22 and R23 is independently selected from the group consisting of hydrogen, an alkyl group, and substituted alkyl groups;
wherein R30 is positioned ortho or para to the bridging amine moiety and is selected from the group consisting of —OR38 and —NR36R37, wherein each R36 and R37 is independently selected from the group consisting of hydrogen, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an acyl group, R4, —C(O)OR1, —C(O)R1, and —C(O)NR1R2;
wherein R38 is selected from the group consisting of hydrogen, an acyl group, —C(O)OR1, —C(O)R1, and —C(O)NR1R2;
wherein g and h are independently integers from 0 to 4;
wherein each R31 and R32 is independently selected from the group consisting of an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an alkaryl, substituted alkaryl, —C(O)R1, —C(O)OR1, —C(O)O−, —C(O)NR1R2, —OC(O)R1, —OC(O)OR1, —OC(O)NR1R2, —S(O)2R1, —S(O)2OR1, —S(O)2O−, —S(O)2NR1R2, —NR1C(O)R2, —NR1C(O)OR2, —NR1C(O)SR2, —NR1C(O)NR2R3, —OR1, —NR1R2, —P(O)2R1, —P(O)(OR1)2, —P(O)(OR1)O−, and —P(O)(O−)2;
wherein —NR34R35 is positioned ortho or para to the bridging amine moiety and R34 and R35 are independently selected from the group consisting of hydrogen, an alkyl, a substituted alkyl, an aryl, a substituted aryl, an alkaryl, a substituted alkaryl, and R4;
wherein R33 is independently selected from the group consisting of hydrogen, —S(O)2R1, —C(O)N(H)R1; —C(O)OR1; and —C(O)R1; wherein when g is 2 to 4, any two adjacent R31 groups may combine to form a fused ring of five or more members wherein no more than two of the atoms in the fused ring may be nitrogen atoms;
wherein X40 is selected from the group consisting of an oxygen atom, a sulfur atom, and NR45; wherein R45 is independently selected from the group consisting of hydrogen, deuterium, an alkyl, a substituted alkyl, an aryl, a substituted aryl, an alkaryl, a substituted alkaryl, —S(O)2OH, —S(O)2O−, —C(O)OR1, —C(O)R1, and —C(O)NR1R2;
wherein R40 and R41 are independently selected from the group consisting of —(CH2)n—O—R1, —(CH2)n—NR1R2, wherein the index n is an integer from 0 to 4;
wherein j and k are independently integers from 0 to 3;
wherein R42 and R43 are independently selected from the group consisting of an alkyl, a substituted alkyl, an aryl, a substituted aryl, an alkaryl, a substituted alkaryl, —S(O)2R1, —C(O)NR1R2, —NC(O)OR1, —NC(O)SR1, —C(O)OR1, —C(O)R1, —OR1, —NR1R2;
wherein R44 is —C(O)R1, —C(O)NR1R2, and —C(O)OR1;
wherein any charge present in any of the compounds is balanced with a suitable independently selected internal or external counterion.

### Claim 7 (depends on 6)

The laundry care composition of claim 6, wherein the leuco compound is a compound of formula I.

### Claim 8 (depends on 7)

The laundry care composition of claim 7, wherein two Ro groups on different A, B and C rings combine to form a fused ring of five or more members.

### Claim 9 (depends on 8)

The laundry care composition of claim 8, wherein the fused ring is six or more members and two Ro groups on different A, B and C rings combine to form an organic linker containing one or more heteroatoms.

### Claim 10 (depends on 8)

The laundry care composition of claim 8, wherein all of the Ro and Rm groups on all three rings A, B or C are hydrogen.

### Claim 11 (depends on 10)

The laundry care composition of claim 10, wherein each Rp is an independently selected —NR1R2 group.

### Claim 12 (depends on 6)

The laundry care composition of claim 6, wherein the organic group may be substituted with one or more additional leuco colorant moieties conforming to the structure of Formula I.

### Claim 13 (depends on 6)

The laundry care composition of claim 6, wherein R4 is selected from the group consisting of alkyleneoxy, oxoalkyleneoxy, oxoalkyleneamine, epichlorohydrin, quaternized epichlorohydrin, alkyleneamine, hydroxyalkylene, acyloxyalkylene, carboxyalkylene, carboalkoxyalkylene, and sugar.

### Claim 14 (depends on 6)

The laundry care composition of claim 6, wherein the suitable independently selected external counterions are selected from the group consisting of Na, K, Mg, Ca, iminium, ammonium, phosphonium, fluoride, chloride, bromide, iodide, perchlorate, hydrogen sulfate, sulfate, aminosulfate, nitrate, dihydrogen phosphate, hydrogen phosphate, phosphate, bicarbonate, carbonate, methosulfate, ethosulfate, cyanate, thiocyanate, tetrachiorozincate, borate, tetrafluoroborate, acetate, chloroacetate, cyanoacetate, hydroxyacetate, aminoacetate, methylaminoacetate, di- and tri-chloroacetate, 2-chloro-propionate, 2-hydroxypropionate, glycolate, thioglycolate, thioacetate, phenoxyacetate, trimethylacetate, valerate, palmitate, acrylate, oxalate, malonate, crotonate, succinate, citrate, methylene-bis-thioglycolate, ethylene-bis-iminoacetate, nitrilotriacetate, fumarate, maleate, benzoate, methylbenzoate, chlorobenzoate, dichlorobenzoate, hydroxybenzoate, aminobenzoate, phthalate, terephthalate, indolylacetate, chlorobenzenesulfonate, benzenesulfonate, toluenesulfonate, biphenyl-sulfonate and chlorotoluenesulfonate.

### Claim 15 (depends on 1)

The laundry care composition of claim 1, wherein the laundry care ingredient is selected from the group consisting of surfactants, builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, enzyme stabilizers, catalytic materials, bleach activators, polymeric dispersing agents, clay soil removal agents, anti-redeposition agents, brighteners, suds suppressors, dyes, perfume, perfume delivery systems, structurants, fabric softeners, carriers, hydrotropes, processing aids, pigments, antioxidants and mixtures thereof.

### Claim 16 (depends on 1)

A method for treating textile articles comprising the steps of: (a) providing the laundry care composition of claim 1; (b) adding the laundry care composition to a liquid medium; (c) placing textile articles in the liquid medium; (d) optionally, rinsing the textile; and (e) drying the textile articles.