Pre-dyes, pre-dye compositions, and methods of developing a color

• US 5,837,429 A
• Filed: 06/05/1996
• Issued: 11/17/1998
• Est. Priority Date: 06/05/1995
• Status: Expired due to Fees

• Current Assignee: Kimberly-Clark Worldwide Incorporated (Kimberly-Clark Corporation)
• Original Assignee: Kimberly-Clark Worldwide Incorporated (Kimberly-Clark Corporation)
• Inventors: MacDonald, John Gavin, Nohr, Ronald Sinclair
• Primary Examiner(s): McPherson, John A.
• Application Number:
  US08/659,497
• Time in Patent Office: 895 Days
• Field of Search: 430/332, 430/338, 430/340, 430/343, 430/346, 503/200, 503/224, 552/114
• US Class Current: 430/343
• CPC Class Codes: C09B 67/0077 Preparations with possibly reduced vat, sulfur or indigo dyes
• CPC Class Codes: G03C 1/732 Leuco dyes

Abstract

One embodiment of the present invention is a method and composition comprising a novel pre-dye molecule that is colorless and stable to ordinary light. The pre-dye molecule is capable of forming a color when exposed to certain wavelengths of electromagnetic radiation. A second embodiment of the present invention is a method of converting a conventional leuco dye to a colored composition by exposing the leuco dye admixed with a radiation transorber to certain wavelengths of electromagnetic radiation.

Claims

1. A pre-dye composition comprising a dye covalently bound to a radiation transorber adapted so that the pre-dye is colorless and will form a color when irradiated with radiation, the radiation transorber comprising a wavelength-selective sensitizer covalently bonded to a reactive species-generating photoreactor, wherein said composition further comprises a molecular includant covalently bonded to the radiation transorber.

2. The pre-dye composition claim 1, wherein the dye is an aminotriarylmethane dye.

3. The pre-dye composition of claim 1, wherein the photoreactor is 1- 4-(2-hydroxyethoxy)phenyl!-2-hydroxy-2-methyl-propan-1-one having the following formula ##STR36## or 1-hydroxycyclohexane phenyl ketone having the following formula ##STR37##

4. The pre-dye composition of claim 1, wherein the wavelength-selective sensitizer is phthaloylglycine having the following formula ##STR38## or 4-(4-Hydroxy phenyl) butan-2-one having the following formula ##STR39##

5. The pre-dye composition of claim 1, wherein the radiation transorber is 2-(p-(2-methyllactoyl)phenoxy)ethyl 1,3-dioxo-2-isoindoline-acetate having the formula ##STR40## phthaloylglycyl-cyclohexylphenyl ketone ester having the formula ##STR41## 4-(4-oxyphenyl)-2-butanone-1-(4-(2-oxyethoxy)phenyl)-2-hydroxy-2-methyl-propan-1-one (or 2-hydroxy-2-methyl-4'"'"'-(2-(p-(3-oxobutyl)phenoxy)ethoxy)-propiophenone) having the formula ##STR42## 4-(4-oxyphenyl)-2-butanonecyclohexyl-phenyl ketone (or 4-(p-((4-benzoylcyclohexyl)oxy)phenyl)-2-butanone) having the formula ##STR43##

6. A method of developing a color comprising:

providing a composition comprising a pre-dye, wherein the pre-dye comprises a dye covalently bound to a radiation transorber which is covalently bonded to a molecular includant, and wherein the pre-dye is colorless and will form a color when irradiated with radiation, the radiation transorber comprising a wavelength-selective sensitizer covalently bonded to a reactive species-generating photoreactor; and

irradiating the composition with radiation at a wavelength and dosage level sufficient to irreversibly mutate the colorant.

7. The method of claim 6, wherein the dye is an aminotriarylmethane dye.

8. The method of claim 6, wherein the photoreactor is 1- 4-(2-hydroxyethoxy)phenyl!-2-hydroxy-2-methyl-propan-1-one having the following formula ##STR44## or 1-hydroxycyclohexane phenyl ketone having the following formula ##STR45##

9. The method of claim 6, wherein the wavelength-selective sensitizer is phthaloylglycine having the following formula ##STR46## or 4-(4-Hydroxy phenyl) butan-2-one having the following formula ##STR47##

10. The method of claim 6, wherein the radiation transorber is 2-(p-(2-methyllactoyl)phenoxy)ethyl 1,3-dioxo-2-isoindoline-acetate having the formula ##STR48## phthaloylglycyl-cyclohexylphenyl ketone ester having the formula ##STR49## 4-(4-oxyphenyl)-2-butanone-1-(4-(2-oxyethoxy)phenyl)-2-hydroxy-2-methyl-propan-1-one (or 2-hydroxy-2-methyl-4'"'"'-(2-(p-(3-oxobutyl)phenoxy)ethoxy)-propiophenone) having the formula ##STR50## or 4-(4-oxyphenyl)-2-butanonecyclohexyl-phenyl ketone (or 4-(p-((4-benzoylcyclohexyl)oxy)phenyl)-2-butanone) having the formula ##STR51##

11. A mutable dye composition comprising a leuco dye admixed with a radiation transorber and a molecular includant, wherein the radiation transorber comprises a wavelength-selective sensitizer covalently bonded to a reactive species-generating photoreactor, and wherein the radiation transorber is covalently bonded to the molecular includant.

12. The mutable dye composition of claim 11, wherein the dye is a leuco aminotriarylmethane dye.

13. The mutable dye composition of claim 11, wherein the photoreactor is 1- 4-(2-hydroxyethoxy)phenyl!-2-hydroxy-2-methyl-propan-1-one having the following formula ##STR52## or 1-hydroxycyclohexane phenyl ketone having the following formula ##STR53##

14. The mutable dye composition of claim 11, wherein the wavelength-selective sensitizer is phthaloylglycine having the following formula ##STR54## or 4-(4-Hydroxy phenyl) butan-2-one having the following formula ##STR55##

15. The mutable dye composition of claim 11, wherein the radiation transorber is 2-(p-(2-methyllactoyl)phenoxy)ethyl 1,3-dioxo-2-isoindoline-acetate having the formula ##STR56## phthaloylglycyl-cyclohexylphenyl ketone ester having the formula ##STR57## 4-(4-oxyphenyl)-2-butanone-1-(4-(2-oxyethoxy)phenyl)-2-hydroxy-2-methyl-propan-1-one (or 2-hydroxy-2-methyl-4'"'"'-(2-(p-(3-oxobutyl)phenoxy)ethoxy)-propiophenone) having the formula ##STR58## 4-(4-oxyphenyl)-2-butanonecyclohexyl-phenyl ketone (or 4-(p-((4-benzoylcyclohexyl)oxy)phenyl)-2-butanone) having the formula ##STR59##

16. A method of developing a color comprising:

providing a composition comprising a leuco dye admixed with a radiation transorber covalently bonded to a molecular includant, wherein the radiation transorber comprises a wavelength-selective sensitizer covalently bonded to a reactive species-generating photoreactor; and

irradiating the composition with radiation at a wavelength and dosage level sufficient to irreversibly mutate the leuco dye.

17. The method of claim 16, wherein the dye is a leuco aminotriarylmethane dye.

18. The method of claim 16, wherein the photoreactor is 1- 4-(2-hydroxyethoxy)phenyl!-2-hydroxy-2-methyl-propan-1-one having the following formula ##STR60## or 1-hydroxycyclohexane phenyl ketone having the following formula ##STR61##

19. The method of claim 16, wherein the wavelength-selective sensitizer is phthaloylglycine having the following formula ##STR62## or 4-(4-Hydroxy phenyl) butan-2-one having the following formula ##STR63##

20. The method of claim 16, wherein the radiation transorber is 2-(p-(2-methyllactoyl)phenoxy)ethyl 1,3-dioxo-2-isoindoline-acetate having the formula ##STR64## phthaloylglycyl-cyclohexylphenyl ketone ester having the formula ##STR65## 4-(4-oxyphenyl)-2-butanone-1-(4-(2-oxyethoxy)phenyl)-2-hydroxy-2-methyl-propan-1-one (or 2-hydroxy-2-methyl-4'"'"'-(2-(p-(3-oxobutyl)phenoxy)ethoxy)-propiophenone) having the formula ##STR66## or 4-(4-oxyphenyl)-2-butanonecyclohexyl-phenyl ketone (or 4-(p-((4-benzoylcyclohexyl)oxy)phenyl)-2-butanone) having the formula ##STR67##

21. A pre-dye having the formula ##STR68## wherein X represents a radiation transorber, and wherein R represents a hydrogen, an alkyl group or an aryl group.

22. The pre-dye of claim 21, wherein the radiation transorber comprises a wavelength-selective sensitizer covalently bonded to a reactive species-generating photoreactor and the photoreactor is 1- 4-(2-hydroxyethoxy)phenyl!-2-hydroxy-2-methyl-propan-1-one having the following formula ##STR69## or 1-hydroxycyclohexane phenyl ketone having the following formula ##STR70##

23. The pre-dye of claim 21, wherein the radiation transorber comprises a wavelength-selective sensitizer covalently bonded to a reactive species-generating photoreactor and the wavelength-selective sensitizer is phthaloylglycine having the following formula ##STR71## or 4-(4-Hydroxy phenyl) butan-2-one having the following formula ##STR72##

24. The pre-dye of claim 21, wherein the radiation transorber is 2-(p-(2-methyllactoyl)phenoxy)ethyl 1,3-dioxo-2-isoindoline-acetate having the formula ##STR73## phthaloylglycyl-cyclohexylphenyl ketone ester having the formula ##STR74## 4-(4-oxyphenyl)-2-butanone-1-(4-(2-oxyethoxy)phenyl)-2-hydroxy-2-methyl-propan-1-one (or 2-hydroxy-2-methyl-4'"'"'-(2-(p-(3-oxobutyl)phenoxy)ethoxy)-propiophenone) having the formula ##STR75## or 4-(4-oxyphenyl)-2-butanonecyclohexyl-phenyl ketone (or 4-(p-((4-benzoylcyclohexyl)oxy)phenyl)-2-butanone) having the formula ##STR76##

25. A method of developing a color comprising:

providing a pre-dye which is colorless and forms a color when irradiated with radiation; and

irradiating the pre-dye with radiation at a wavelength and dosage level sufficient to irreversibly mutate the pre-dye;

wherein the pre-dye has the formula ##STR77## wherein X represents a radiation transorber, and wherein R represents a hydrogen, an alkyl group or an aryl group.

26. The method of claim 25, wherein the radiation transorber comprises a wavelength-selective sensitizer covalently bonded to a reactive species-generating photoreactor and the photoreactor is 1- 4-(2-hydroxyethoxy)phenyl!-2-hydroxy-2-methyl-propan-1-one having the following formula ##STR78## or 1-hydroxycyclohexane phenyl ketone having the following formula ##STR79##

27. The method of claim 25, wherein the radiation transorber comprises a wavelength-selective sensitizer covalently bonded to a reactive species-generating photoreactor and the wavelength-selective sensitizer is phthaloylglycine having the following formula ##STR80## or 4-(4-Hydroxy phenyl) butan-2-one having the following formula ##STR81##

28. The method of claim 25, wherein the radiation transorber is 2-(p-(2-methyllactoyl)phenoxy)ethyl 1,3-dioxo-2-isoindoline-acetate having the formula ##STR82## phthaloylglycyl-cyclohexylphenyl ketone ester having the formula ##STR83## 4-(4-oxyphenyl)-2-butanone-1-(4-(2-oxyethoxy)phenyl)-2-hydroxy-2-methyl-propan-1-one (or 2-hydroxy-2-methyl-4'"'"'-(2-(p-(3-oxobutyl)phenoxy)ethoxy)-propiophenone) having the formula ##STR84## or 4-(4-oxyphenyl)-2-butanonecyclohexyl-phenyl ketone (or 4-(p-((4-benzoylcyclohexyl)oxy)phenyl)-2-butanone) having the formula ##STR85##