Leuco polymers as bluing agents in laundry care compositions

Abstract

A leuco polymer includes a leuco monomer and an alkene. The leuco polymer has a molecular weight of at least 500 and is obtainable by polymerization of the leuco monomer and one or more alkene co-monomers. The leuco monomer consists of an alkene covalently bound to a leuco moiety and the leuco monomer has a molar extinction coefficient at a wavelength in the range 400 to 750 nm of less than 1000 M−1cm−1. The alkene monomer(s) have a molar extinction coefficient at a wavelength in the range 400 to 750 nm that is less than 100 M−1cm−1. Methods of making the leuco polymer, laundry care compositions comprising the leuco polymer and methods of treating textiles with such laundry care compositions.

We claim: 
     
         1 . A leuco polymer comprising a leuco monomer and an alkene, wherein the leuco polymer has a molecular weight of at least 500 and is obtainable by polymerization of the leuco monomer and one or more alkene co-monomers, wherein the leuco monomer consists of an alkene covalently bound to a leuco moiety and the leuco monomer has a maximum molar extinction coefficient at a wavelength in the range 400 to 750 nm of less than 1000 M −1 cm −1 , wherein the alkene co-monomer(s) have a maximum molar extinction coefficient at a wavelength in the range 400 to 750 nm that is less than 100 M −1 cm −1 . 
     
     
         2 . The leuco polymer 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 leuco polymer of  claim 1 , wherein the leuco monomer is of the form: 
       
         
           
           
               
               
           
         
         wherein Y is an organic bridging group covalently connecting a leuco moiety to the alkene moiety of the leuco monomer and R 1  is selected from the group consisting H, unsubstituted or substituted alkyl, unsubstituted or substituted aryl, benzyl, halogen, ester, acid amide, and cyano. 
       
     
     
         4 . The leuco polymer of  claim 1 , wherein the organic bridging group is selected from: —CON(R 4 )—, —CO 2 —, —N(R 4 )—, —O—, —S—, —SO 2 —, —SO 2 N(R 4 )—, —N(COR 4 )—, and —N(SO 2 R 4 )—; wherein R 4  is selected from the group consisting of H, phenyl, benzyl and unsubstituted or substituted C 1 -C 6  branched or linear alkyl wherein the substituent of said linear or branched alkyl is located between two carbons of said alkyl and is selected from the group consisting of —O—, —S—, —SO 2 —, —CO 2 —, and an amine. 
     
     
         5 . The leuco polymer of  claim 4 , wherein the organic bridging group is —CON(R 4 )—. 
     
     
         6 . The leuco polymer of  claim 5 , wherein R 4  is selected from H and methyl. 
     
     
         7 . The leuco polymer of  claim 3 , wherein the Y group is bound directly to a carbon atom of an aromatic ring of the leuco moiety. 
     
     
         8 . The leuco polymer of  claim 3 , wherein R 1  is selected from H, methyl, ethyl, propyl, CO 2 C 1-4  branched and linear alkyl chains, phenyl, benzyl, CN, Cl, and F. 
     
     
         9 . The leuco polymer of  claim 3 , wherein R 1  is selected from H and methyl. 
     
     
         10 . The leuco polymer of  claim 4 , wherein the leuco monomer is selected from the group consisting of:
 (i) a leuco moiety wherein one —NR 4 H of the leuco moiety is converted to —NR 4 —C(O)—CH═CH 2  or —NR 4 —C(O)—C(Me)═CH 2 , wherein R 4 is as defined above; or   (ii) a leuco moiety wherein one —OH of the leuco moiety is converted to —O—C(O)—CH═CH 2  or —O—C(O)—C(Me)═CH 2 .   
     
     
         11 . The leuco polymer of  claim 10 , wherein the leuco monomer is: 
       
         
           
           
               
               
           
         
         wherein the leuco moiety carries at least one sulphonate. 
       
     
     
         12 . The leuco polymer of  claim 10 , wherein the leuco monomer is: 
       
         
           
           
               
               
           
         
         wherein the leuco moiety carries at least one sulphonate. 
       
     
     
         13 . The leuco polymer of  claim 1 , wherein the co-monomer is selected from: 
       
         
           
           
               
               
           
         
         wherein R 2  and R 3  are independently selected from H, C 1 -C 8  branched, cyclic and linear alkyl chains, C(O)OH, CO 2 C 1-18  branched and linear alkyl chains, —C(O)N(C 1-18 ) 2 , —C(O)N(C 1-18 )H, —C(O)NH 2 , and heteroaromatic, phenyl, benzyl, polyether, cyano, Cl and F. 
       
     
     
         14 . The leuco polymer of  claim 13 , wherein R 2  and R 3  of the co-monomer is further substituted by groups selected from charged and uncharged organic, the further groups having a total molecular weight of less than 400. 
     
     
         15 . The leuco polymer of  claim 2 , 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. 
       
     
     
         16 . The leuco polymer of  claim 15 , wherein the leuco moiety is a univalent or polyvalent moiety derived by removal of one or more hydrogen atoms from a compound conforming to a structure of Formula (I), (II), or (IV). 
     
     
         17 . The leuco polymer of  claim 15 , wherein the leuco moiety is a moiety of Formula (I). 
     
     
         18 . The leuco polymer of  claim 16 , wherein two R o  groups on different A, B and C rings combine to form a fused ring of five or more members. 
     
     
         19 . The leuco polymer of  claim 18 , 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. 
     
     
         20 . The leuco polymer of  claim 19 , wherein two R o  on different A, B and C rings combine to form a heteroatom bridge selected from —0—and —S—to create a six member fused ring. 
     
     
         21 . The leuco polymer of  claim 17 , 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. 
     
     
         22 . The leuco polymer of  claim 17 , wherein all four of the R o  and R m  groups on at least one of the three rings A, B or C are hydrogen. 
     
     
         23 . The leuco polymer of  claim 22 , wherein all of the R o  and R m  groups on all three rings A, B or C are hydrogen. 
     
     
         24 . The leuco polymer of  claim 17 , wherein all three R p  are —NR 1 R 2 . 
     
     
         25 . The leuco polymer of  claim 1 , wherein the leuco polymer further comprises a covalently bound chromophore moiety, wherein the chromophore moiety is selected from the group consisting of diarylmethane moieties, triarylmethane moieties, oxazine moieties, thiazine moieties, anthraquinone moieties, and indoaniline moieties.