Leuco colorants and compositions

Patent metadata

Field	Value
Publication number	US-10717874-B2
Application number	US-201816157917-A
Country	US
Kind code	B2
Filing date	Oct 11, 2018
Priority date	Dec 8, 2017
Publication date	Jul 21, 2020
Grant date	Jul 21, 2020

Abstract

A leuco composition comprises at least one leuco compound, the leuco compound comprising a leuco moiety and a polyalkyleneoxy moiety covalently bound to the leuco moiety. The polyalkyleneoxy moiety comprises at least one ethylene oxide group and at least one propylene oxide group. A laundry care composition comprises (a) at least one laundry care ingredient and (b) a leuco composition as described above. A method of treating a textile includes the steps of (a) providing such a laundry care composition; (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.

First claim

We claim:

1. A leuco composition comprising at least one leuco compound, the leuco compound comprising a leuco moiety and an alkyleneoxy moiety covalently bound to the leuco moiety, wherein the alkyleneoxy moiety comprises at least one ethylene oxide group and at least one propylene oxide group, wherein the leuco compound has the structure of Formula (CI)

wherein the ratio of Formula (CI) to its oxidized form is at least 1:3; wherein each individual R o , R m and R p group on each of rings A, B and C is independently selected from the group consisting of hydrogen, deuterium and R 5 ; wherein each R 5 is independently selected from the group consisting of halogens, nitro, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, —(CH 2 ) n —O—R 1 , —(CH 2 ) n —NR 1 R 2 , —C(O)R 1 , —C(O)OR 1 , —C(O)O − , —C(O)NR 1 R 2 , —OC(O)R 1 , —OC(O)OR 1 , —OC(O)NR 1 R 2 , —S(O) 2 R 1 , —S(O) 2 OR 1 , —S(O) 2 O − , —S(O) 2 NR 1 R 2 , —NR 1 C(O)R 2 , —NR 1 C(O)OR 2 , —NR 1 C(O)SR 2 , —NR 1 C(O)NR 2 R 3 , —P(O) 2 R 1 , —P(O)(OR 1 ) 2 , —P(O)(OR 1 )O − , and —P(O)(O − ) 2 ; wherein the index n is an integer from 0 to 4;
wherein G is independently selected from the group consisting of hydrogen, deuterium, C 1 -C 16 alkoxide, phenoxide, bisphenoxide, nitrite, nitrile, alkyl amine, imidazole, arylamine, polyalkylene oxide, halides, alkylsulfide, aryl sulfide, and phosphine oxide;
wherein R 1 , R 2 and R 3 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and an alkyleneoxy moiety;
wherein any charge present in the compound is balanced with a suitable independently selected internal or external counterion; and
wherein the leuco compound has a maximum molar extinction coefficient at a wavelength in the range of 400 to 750 nm of less than 1,000 M −1 cm −1 .

2. The leuco composition of claim 1 , wherein the alkyleneoxy moiety comprises from 1 to about 20 ethylene oxide groups and from 1 to about 20 propylene oxide groups.

3. The leuco composition of claim 1 , wherein the alkyleneoxy moiety is covalently bound to the leuco moiety through a nitrogen atom, the nitrogen atom and the alkyleneoxy moiety together having the structure —NR 1 (C 2 H 4 O) n (C 3 H 6 O) q H, where n and q are independently selected from integers from 1 to 5, and R 1 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and alkyleneoxy moieties.

4. The leuco composition of claim 1 , wherein the leuco compound comprises two alkyleneoxy moieties, each alkyleneoxy moiety being covalently bound to the leuco moiety through a nitrogen atom, the nitrogen atom and the alkyleneoxy moieties together having the structure

where n, q, r, and s are independently selected from integers from 0 to 5, the sum of n and r is from 2 to 10, and the sum of q and s is from 2 to 10.

5. The leuco composition of claim 4 , wherein the sum of n and r is from 2 to 5, and the sum of q and s is from 2 to 5.

6. The leuco composition of claim 1 , wherein G is hydrogen.

7. The leuco composition of claim 1 , wherein the leuco composition further comprises a solvent selected from the group consisting of water, ethylene glycol, propylene glycol, glycerin, poly(ethylene glycol), poly(propylene glycol), copolymers of ethylene oxide and propylene oxide and mixtures thereof.

8. The leuco composition of claim 1 , wherein the leuco compound is present in the composition in an amount of about 10 wt. % or more.

9. The leuco composition of claim 1 , wherein the leuco composition further comprises an antioxidant compound.

10. The leuco composition of claim 9 , wherein the antioxidant compound is selected from the group consisting of hindered phenols, diaryl amines, benzofuranones and mixture thereof.

11. The leuco composition of claim 10 , wherein the leuco composition comprises about 0.01 to about 20 wt. % of a hindered phenol.

12. A leuco composition obtained from the following steps: (i) providing one molar equivalent of an aromatic aldehyde, (ii) providing approximately two molar equivalents of an aryl coupler or mixture of aryl couplers wherein at least one aryl coupler comprises a covalently bound oxyalkylene or polyoxyalkylene moiety, wherein the oxyalkylene or polyoxyalkylene moiety comprises at least one ethylene oxide group and at least one propylene oxide group, (iii) combining said aromatic aldehyde and aryl coupler(s) in a suitable reaction vessel, (iv) adding between 0.01 and 0.5 equivalents of urea, (v) adding muriatic acid to achieve a pH of between about 0 and 3, (vi) heating the mixture between 60° C. to 120° C. for between 2 hours to 12 hours, (vii) adjusting the pH to at least about 7, and (viii) separating at least a portion of the salts formed upon neutralization from the liquid product; wherein said leuco composition comprises at least one leuco compound, the leuco compound comprising a leuco moiety and a alkyleneoxy moiety covalently bound to the leuco moiety, wherein the alkyleneoxy moiety comprises at least one ethylene oxide group and at least one propylene oxide group, and wherein the leuco compound has a maximum molar extinction coefficient at a wavelength in the range of 400 to 750 nm of less than 1,000 M −1 cm −1 .

13. The leuco composition of claim 12 wherein the leuco compound has the formula (CVII)

wherein each index c is independently 0, 1 or 2, preferably each c is 1; each R 4 is independently selected from the group consisting of H, Me, Et, ((CH 2 CH 2 O) a (C 3 H 6 O) b )H, and mixtures thereof; each index b is independently an integer from 0-25 and wherein the sum of all the independently selected a integers in the leuco colorant is no more than 100 and the sum of all the independently selected b integers in the leuco colorant is at least 1 and no more than 50.

14. The leuco composition of claim 13 wherein the leuco compound has the formula (CVIII)

wherein R 8 is H or CH 3 and each index b is independently on average about 1 to 2.

Assignees

• Milliken & Co

Inventors

• Qin Haihu
• Dey Sanjeev K
• Freund Wesley A
• Petrea Randy D
• Miracle Gregory S

Classifications

• C09B11/12 Primary

  without any OH group bound to an aryl nucleus · CPC title

• C09B69/00

  Dyes not provided for by a single group of this subclass · CPC title

• C11D3/40

  Dyes {; Pigments} · CPC title

• C09B11/06

  Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus {and their ethers or esters} · CPC title

• C09B9/00

  Esters or ester-salts of leuco compounds of vat dyestuffs · CPC title