Leuco polymers as bluing agents in laundry care compositions

Patent metadata

Field	Value
Publication number	US-10647854-B2
Application number	US-201715800734-A
Country	US
Kind code	B2
Filing date	Nov 1, 2017
Priority date	Nov 1, 2016
Publication date	May 12, 2020
Grant date	May 12, 2020

Abstract

A method of obtaining a leuco polymer, the method comprising the step of reacting a reactive leuco compound with a polymer to form the leuco polymer. The reactive leuco compound comprises at least one leuco moiety and at least one nucleophilic group. The polymer comprises at least one group capable of reacting with said nucleophilic group. The said leuco moiety has a maximum molar extinction coefficient at a wavelength in the range 400 to 750 nm of less than 1000 M −1 cm −1 . Laundry care compositions comprising the leuco polymer and methods of treating textiles with such laundry care compositions.

First claim

We claim:

1. A method of obtaining a leuco polymer, the method comprising the step of reacting a compound with a polymer to form the leuco polymer, wherein the compound comprises at least one leuco moiety and at least one nucleophilic group, wherein the polymer comprises at least one group capable of reacting with said nucleophilic group, wherein said leuco moiety has a maximum molar extinction coefficient at a wavelength in the range 400 to 750 nm of less than 1000 M −1 cm −1 , and wherein the leuco polymer contains 0.1 to 30 mol. % leuco moieties.

2. The method of claim 1 , wherein the nucleophilic group is selected from the group consisting of a primary amine, a secondary amine, a hydroxyl, an eneamine, a carbanion, and a sulfhydryl group.

3. The method of claim 1 , wherein the group capable of reacting with the nucleophilic group is selected from the group consisting of isocyanate; oxazolone, epoxide, ester, α, β-unsaturated carbonyls, α, β-unsaturated sulfonyls, halotriazines, halosilane, aldehyde, ketone, sulfonyl halide, carboxylic acid halide, and anhydride, carboxylic acid, and alkyl halide.

4. The method of claim 3 , wherein the group capable of reacting with said nucleophilic group is selected from the group consisting of epoxide, carboxylic acid, carboxylic acid ester, carboxylic acid halide, and carboxylic acid anhydride.

5. The method of claim 4 , wherein the group capable of reacting with said nucleophilic group is selected from the group consisting of epoxide and carboxylic acid anhydride.

6. The method of claim 2 , the nucleophilic group in said compound is selected from the group consisting of primary amine group, secondary amine group, or a hydroxyl group.

7. The method of claim 1 , wherein the polymer is obtained by polymerization of maleic anhydride, itaconic anhydride or

and a comonomer of the form:

wherein R 7 and R 8 are organic groups independently selected from: H; C 1 -C 8 alkyl; OC 1 -C 8 alkyl; C(O)OH; CO 2 C 1 -C 18 alkyl; CO 2 C 1 -C 4 N(C 1 -C 4 alkyl) 2 ; —C(O)N(C 1 -C 18 alkyl) 2 ; —C(O)N(C 1 -C 18 alkyl)H; —C(O)NH 2 ; heteroaromatic; phenyl; benzyl; polyether; pyrrolidone; imidazole; cyano; Cl and F.

8. The method of claim 7 , wherein R 7 is selected from H and CH 3 and R 8 is selected from —OMe and -OEt.

9. The method 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.

10. The method of claim 9 , 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), (Ill), (IV), or (V) . . .

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, 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 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 35 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 , —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 —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 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 , —OR 1 , —NR 1 R 2 ;
wherein R 44 is —C

Assignees

• Milliken & Co

Inventors

• Dey Sanjeev K
• Qin Haihu
• Miracle Gregory S

Classifications

• C11D3/3769

  (Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines · CPC title

• C11D3/42

  Brightening agents {; Blueing agents} · CPC title

• C08F222/08

  with vinyl aromatic monomers · CPC title

• C09B69/101

  containing an anthracene dye · CPC title

• C09B69/109 Primary

  containing other specific dyes · CPC title