Triarylmethane leuco compounds and compositions comprising the same

A triarylmethane leuco compound of Formula (C)

• 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;
• R103 is selected from the group consisting of hydrogen, —OR120, and —NR120R121;
• R108 and R113 are independently selected from the group consisting of —OR122 and —NR122R123;
• each R120, R121, R122 and R123 is independently selected from the group consisting of alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and alkyleneoxy;
• R101, R102, R104, R105, R106, R107, R109, R110, R111, R112, R114, and R115 are independently selected from the group consisting of hydrogen, deuterium, halogens, nitro, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, —C(O)R1, —C(O)OR1, —C(O)O−, —C(O)NR1R2, —OC(O)R1, —OC(O)OR1, —OC(O)NR1R2, —S(O)2R1, —S(O)2OR1, —S(O)2O−, —S(O)2NR1R2, —NR1C(O)R2, —NR1C(O)OR2, —NR1C(O)SR2, —NR1C(O)NR2R3, —OR1, —NR1R2, —P(O)2R1, —P(O)(OR1)2, —P(O)(OR1)O−, and —P(O)(O−)2;
• R1, R2 and R3 are independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, alkaryl, substituted alkaryl, and R4;
• R4 is an organic group composed of one or more organic monomers with said monomer molecular weights ranging from 28 to 500;
• provided (1) at least one of R106 and R110 is different from R111 and R115 or at least one of R107 and R109 is different from R112 and R114;
• (2) if R103 is —OR120 and R108 and R113 are each —OR122, then at least one of R106 and R110 is different from R101 and R105 or at least one of R107 and R109 are different from R102 and R104;
• and (3) if R103 is —NR120R121 and R108 and R113 are each —NR122R123, then at least one of R106 and R110 is different from R101 and R105 or at least one of R107 and R109 are different from R102 and R104.

A composition comprising a plurality of triarylmethane leuco molecules, wherein:

• (i) each triarylmethane leuco molecule comprises a first aryl moiety, a second aryl moiety, and a third aryl moiety, the first aryl moiety comprising a first alkyleneoxy moiety bonded thereto, and the second aryl moiety comprising a second alkyleneoxy moiety bonded thereto;
• (ii) the first alkyleneoxy moiety comprising at least one alkyleneoxy repeating unit selected from the group consisting of ethylene oxide, propylene oxide, and butylene oxide;
• (iii) the second alkyleneoxy moiety comprising at least one alkyleneoxy repeating unit selected from the group consisting of ethylene oxide, propylene oxide, and butylene oxide;
• and
• (iv) about 5 mol. % or more of the triarylmethane leuco molecules present in the composition comprise a first alkyleneoxy moiety that does not contain at least one of the alkyleneoxy repeating units present in the second alkyleneoxy moiety.

A method of making a triarylmethane leuco compound comprising the steps of:

• (a) providing an aromatic aldehyde compound;
• (b) providing a first oxyalkylenated aryl compound;
• (c) providing a second oxyalkylenated aryl compound, wherein the second oxyalkylenated aryl compound is different from the first oxyalkylenated aryl compound;
• (d) providing an acidic catalyst;
• and
• (e) reacting the aromatic aldehyde compound, the first oxyalkylenated compound, and the second oxyalkylenated compound in a condensation reaction in the presence of the acidic catalyst to produce the triarylmethane leuco compound.