Leuco polymers as bluing agents in laundry care compositions

Patent metadata

Field	Value
Publication number	US-10385294-B2
Application number	US-201715800109-A
Country	US
Kind code	B2
Filing date	Nov 1, 2017
Priority date	Nov 1, 2016
Publication date	Aug 20, 2019
Grant date	Aug 20, 2019

Abstract

A laundry care composition including (i) from 2 to 70 wt % of a surfactant; and (ii) from 0.0001 to 20.0 wt % of a leuco polymer including an alkoxylated polyethyleneimine covalently bound to a leuco moiety. At least a first portion of nitrogen atoms of the alkoxylated polyethyleneimine have covalently bound thereto a leuco moiety. At least a second portion of nitrogen atoms of the alkoxylated polyethyleneimine have covalently bound thereto a moiety selected from the group consisting of oxyalkylene moieties, polyoxyalkylene moieties, and mixtures thereof; and at least a third portion of nitrogen atoms of the alkoxylated polyethyleneimine have covalently bound thereto a moiety selected from the group consisting of an alkylene chain, an alkylene chain having covalently bound thereto a phenyl or naphthyl group, and mixtures thereof. Methods of making the leuco polymer and methods of treating textiles with such laundry care compositions.

First claim

We claim:

1. A laundry care composition comprising:
(i) from 2 to 70 wt % of a surfactant; and
(ii) from 0.0001 to 20.0 wt % of a leuco polymer comprising an alkoxylated polyethyleneimine covalently bound to a leuco moiety, wherein at least a first portion of nitrogen atoms of the alkoxylated polyethyleneimine have covalently bound thereto a leuco moiety; at least a second portion of nitrogen atoms of the alkoxylated polyethyleneimine have covalently bound thereto a moiety selected from the group consisting of oxyalkylene moieties, polyoxyalkylene moieties, and mixtures thereof; and at least a third portion of nitrogen atoms of the alkoxylated polyethyleneimine have covalently bound thereto a moiety selected from the group consisting of an alkylene chain, an alkylene chain having covalently bound thereto a phenyl or naphthyl group, and mixtures thereof.

2. A laundry care composition according to claim 1 , wherein the polyethyleneimine has from 6 to 100 nitrogen atoms.

3. A laundry care composition according to claim 2 , wherein the polyethyleneimine has from 12 to 40 nitrogen atoms.

4. A laundry care composition according to claim 1 , wherein the alkylene chain has a pendent alkyl group covalently bound to the polyethyleneimine by the reaction of an amine of the polyethyleneimine with dialkyl sulfates, alcohols, alkyl halides, olefins, and carbonyl compounds.

5. A laundry care composition according to claim 1 , wherein the alkylene chain has a pendent phenyl group formed by the addition of an amine of the polyethyleneimine to styrene oxide or alpha-methyl styrene oxide.

6. A laundry care composition according to claim 1 , wherein the leuco moiety is covalently bound to the nitrogen atom of the alkoxylated polyethyleneimine by reacting the alkoxylated polyethyleneimine with a compound comprising a leuco moiety and an electrophilic moiety, wherein the electrophilic moiety of the compound is selected from the group consisting of sulfooxyethylsulfonyl moieties, vinylsulfonyl moieties, halotriazinyl moieties, quaternary ammoniumtriazinyl moieties, halopyrimidinyl moieties, halopyridazinyl moieties, haloquinoxalinyl moieties, halophthalazinyl moieties, bromoacrlyamidyl moieties, and benzothiazolyl moieties.

7. A laundry care composition according to claim 6 , 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) below

wherein the ratio of Formula I-V 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, —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 at least one of the R o and R m groups on at least one of the three rings A, B or C is hydrogen; each R p is independently selected from hydrogen, —OR 1 and —NR 1 R 2 ;
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 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 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 , 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, —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 , —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 —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 R4;
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 1 ; 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 —OR 1 and —NR 1 R 2 ;
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 , —NR 1 R 2 ;
wherein R 44 is —C(O)R 1 , —C(O)NR 1 R 2 , and —C(O)R 1 ;
wherein any charge present in any of the compounds is balanced with a suitable independently selected internal or external counterion.

8. A laundry care composition according to claim 7 , wherein the leuco moiety is a moiety of Formula (I).

9. A laundry care composition according to claim 8 , wherein two Ro groups on different A, B and C rings combine to form a fused ring of five or more members.

10. A laundry care composition according to claim 9 , wherein the fused ring is

Assignees

• Procter & Gamble

Inventors

• Miracle Gregory Scot
• Qin Haihu
• Dey Sanjeev Kumar

Classifications

• C09B69/109

  containing other specific dyes · CPC title

• C11D3/40

  Dyes {; Pigments} · CPC title

• C11D3/42 Primary

  Brightening agents {; Blueing agents} · CPC title

• C11D3/26

  containing nitrogen {(C11D3/162, C11D3/164, C11D3/166, C11D3/168 take precedence)} · CPC title

• C11D1/00

  Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent · CPC title