Leuco compounds and compositions comprising the same

Patent metadata

Field	Value
Publication number	US-10717951-B2
Application number	US-201816157129-A
Country	US
Kind code	B2
Filing date	Oct 11, 2018
Priority date	Oct 12, 2017
Publication date	Jul 21, 2020
Grant date	Jul 21, 2020

Abstract

A laundry care composition including (a) at least one laundry care ingredient and (b) a leuco compound including an antioxidant moiety covalently bonded to a leuco moiety. A method of treating a textile comprises 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 laundry care composition comprising: (a) at least one laundry care ingredient and (b) a leuco compound comprising at least one antioxidant moiety covalently bound to at least one leuco moiety, provided, when the leuco moiety is a triphenylmethane leuco moiety, the leuco moiety comprises a pendant group covalently bound to an phenyl moiety of the triphenylmethane leuco moiety, wherein the pendant group 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 any two of R 1 , R 2 and R 3 attached to the same heteroatom can combine to form a ring of five or more members optionally comprising one or more additional heteroatoms selected from the group consisting of —O—, —NR 15 —, and —S—; and wherein R 1 , R 2 , R 3 , and R 15 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and R 4 ; and R 4 is an organic group composed of one or more organic monomers with said monomer molecular weights ranging from 28 to 500, wherein the antioxidant moiety is a moiety of Formula (L) or Formula (LI)

wherein R 51 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, and substituted alkaryl.

2. The laundry care composition of claim 1 , wherein the leuco moiety is selected from the group consisting of diarylmethane leuco moieties, triarylmethane leuco moieties, oxazine moieties, thiazine moieties, hydroquinone moieties, and arylaminophenol moieties.

3. The laundry care composition of claim 1 , wherein the leuco moiety is a univalent or polyvalent moiety derived by removal of one or more hydrogen atoms from a structure of Formula (I), (II), (III), (IV), or (V),

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 , —OR 1 , —NR 1 R 2 , —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 any two of R 1 , R 2 and R 3 attached to the same heteroatom can combine to form a ring of five or more members optionally comprising one or more additional heteroatoms selected from the group consisting of —O—, —NR 15 —, and —S—;
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 , R 3 , and R 15 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and R 4 ; R 4 is a 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 R 20 and R 21 is independently selected from the group consisting of a halogen, a nitro group, alkyl groups, substituted alkyl groups, —NC(O)OR 1 , —NC(O)SR 1 , —OR 1 , and —NR 1 R 2 ;
wherein each R 25 is independently selected from the group consisting of a monosaccharide moiety, a disaccharide moiety, an oligosaccharide moiety, a polysaccharide moiety, —C(O)R 1 , —C(O)OR 1 , —C(O)NR 1 R 2 ;
wherein each R 22 and R 23 is independently selected from the group consisting of hydrogen, an alkyl group, and substituted alkyl groups;
wherein R 30 is positioned ortho or para to the bridging amine moiety and is selected from the group consisting of —OR 38 and —NR 36 R 37 , wherein each R 36 and R 37 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, R 4 —C(O)OR 1 , —C(O)R 1 , and —C(O)NR 1 R 2 ;
wherein R 38 is selected from the group consisting of hydrogen, an acyl group, —C(O)OR 1 , —C(O)R 1 , and —C(O)NR 1 R 2 ;
wherein g and h are independently integers from 0 to 4;
wherein each R 31 and R 32 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, —(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 —NR 34 R 35 is positioned ortho or para to the bridging amine moiety and R 34 and R 35 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 R 4 ;
wherein R 33 is independently selected from the group consisting of hydrogen, —S(O) 2 R 1 , —C(O)N(H)R 1 ; —C(O)OR 1 ; and —C(O)R; wherein when g is 2 to 4, any two adjacent R 31 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 X 40 is selected from the group consisting of an oxygen atom, a sulfur atom, and NR 45 ; wherein R 45 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) 2 OH, —S(O) 2 O—, —C(O)OR 1 , —C(O)R 1 , and —C(O)NR 1 R 2 ;
wherein R 40 and R 41 are independently selected from the group consisting of —(CH 2 ) n —O—R 1 , —(CH 2 )—NR 1 R 2 , wherein the index n is an integer from 0 to 4;
wherein j and k are independently integers from 0 to 3;
wherein R 42 and R 43 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) 2 R 1 , —C(O)NR 1 R 2 , —NC(O)OR 1 , —NC(O)SR 1 , —C(O)OR 1 , —C(O)R 1 , —OR 1 , —NR 1 R 2 ;
wherein R 44 is —C(O)R 1 , —C(O)NR 1 R 2 , and —C(O)OR 1 ;
wherein any charge present in any of the compounds is balanced with a suitable independently selected internal or external counterion.

4. The laundry care composition of claim 3 , wherein the leuco moiety is a univalent or polyvalent moiety derived by removal of one or more hydrogen atoms from a structure of Formula (I).

5. The laundry care composition of claim 3 , wherein G is selected from the group consisting of hydrogen, deuterium, and mixtures there

Assignees

• Procter & Gamble

Inventors

• Miracle Gregory Scot
• Dey Sanjeev Kumar
• Qin Haihu
• Valenti Dominick Joseph

Classifications

• C11D3/0084

  Antioxidants; Free-radical scavengers · CPC title

• C11D7/261

  Alcohols; Phenols · CPC title

• C11D3/40

  Dyes {; Pigments} · CPC title

• C11D3/2034

  aromatic · CPC title

• C09B11/12

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