Leuco polymers as bluing agents in laundry care compositions

Patent metadata

Field	Value
Publication number	US-10351709-B2
Application number	US-201715800820-A
Country	US
Kind code	B2
Filing date	Nov 1, 2017
Priority date	Nov 1, 2016
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

A leuco polymer comprising a polyethylenimine and at least one leuco moiety covalently bound to the polyethylenimine, wherein the polyethylenimine comprises three or more amine nitrogen atoms and 1 mol. % or more of amine hydrogen atoms in the polyethylenimine are replaced with a moiety selected from the group consisting of 2-hydroxypropyl, 1-hydroxypropane-2-yl, and polyalkoxy groups. Methods of making the leuco polymer, laundry care compositions comprising the leuco polymer and methods of treating textiles with such laundry care compositions.

First claim

We claim:

1. A leuco polymer comprising a polyethylenimine and at least one leuco moiety covalently bound to the polyethylenimine, wherein the polyethylenimine comprises three or more amine nitrogen atoms and 20 mol. % or more of amine hydrogen atoms in the polyethylenimine are replaced with a moiety selected from the group consisting of 2-hydroxypropyl, 1-hydroxypropane-2-yl, and polyalkoxy groups,
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.

2. The leuco polymer of claim 1 , wherein the polyethylenimine comprises about 6 to about 1,000,000 amine nitrogen atoms.

3. The leuco polymer of claim 1 , wherein the polyethylenimine comprises about 15 to about 45 amine nitrogen atoms.

4. The leuco polymer of claim 1 , wherein about 20 mol. % to about 95 mol. % of amine hydrogen atoms in the polyethylenimine are replaced with 2-hydroxypropyl groups.

5. The leuco polymer of claim 4 , wherein about 57 mol. % to about 80 mol. % of amine hydrogen atoms in the polyethylenimine are replaced with 2-hydroxypropyl groups.

6. The leuco polymer of claim 1 , wherein the polyalkoxy group comprises alkoxy groups selected from the group consisting of ethoxy and propoxy.

7. The leuco polymer of claim 1 , wherein the polyalkoxy group comprises 3 or more repeating alkoxy groups.

8. The leuco polymer of claim 7 , wherein the polyalkoxy group comprises 3 to about 50 repeating alkoxy groups.

9. The leuco polymer 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 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 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 , —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(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.

10. The leuco polymer of claim 9 , wherein the leuco moiety is a moiety of Formula (I).

11. The leuco polymer of claim 10 , wherein two R o groups on different A, B and C rings combine to form a fused ring of five or more members.

12. The leuco polymer of claim 11 , wherein the fused ring is six or more members and two R o groups on different A, B and C rings combine to form an organic linker containing one or more heteroatoms.

13. The leuco polymer of claim 12 , wherein two R o on different A, B and C rings combine to form a heteroatom bridge selected from —O— and —S— to create a six member fused ring.

14. The leuco polymer of claim 10 , wherein either an R o and R m on the same ring or an R m and R p on the same ring combine to form a fused aliphatic ring or fused aromatic ring.

15. The leuco polymer of claim 10 , wherein all four of the R o and R m groups on at least one

Assignees

• Milliken & Co

Inventors

• Dey Sanjeev K
• Miracle Gregory S

Classifications

• D06P1/22

  using vat dyestuffs {including indigo} · CPC title

• C09B11/12

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

• C09B69/10

  Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds · CPC title

• C09B19/00

  Oxazine dyes · CPC title

• C08G75/00

  Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule · CPC title