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1. WO2020112948 - COMPOSITIONS ET PROCÉDÉS POUR LA CONJUGAISON D'UN COLORANT PHÉNOLIQUE À UN SUBSTRAT

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Claims

What is claimed is:

1. A modified pH indicator compound comprising a functional group capable of reacting with an aromatic, hydroxyl, amino or carboxyl group to form a covalent bond.

2. The modified pH indicator compound of claim 1, which is a modified phenolic dye.

3. The modified pH indicator compound of claim 2, wherein the indicator compound is a modified sulfonephthalein dye.

4. The modified pH indicator compound of claim 3, wherein the modified sulfonephthalein dye is selected from the group consisting of modified phenol red, modified cresol red, modified m-cresol purple, modified xylenol blue, modified thymol blue, modified chlorophenol red, modified bromophenol blue, modified bromocresol purple, modified bromocresol green, modified bromothymol blue, modified xylenol orange, and modified methylthymol blue.

5. The modified pH indicator compound of claim 4, selected from the group consisting of modified phenol red, modified cresol red, modified m-cresol purple, modified xylenol blue, modified thymol blue, modified chlorophenol red, and modified xylenol orange.

6. The modified pH indicator compound of any one of claims 1 to 5, having a

hydroxymethyl, carboxy-linker- or NH2-linker- group.

7. The modified pH indicator compound of claim 6, wherein the linker is a straight chain or branched C1-C6-alkylene.

8. The modified pH indicator compound of claim 6, wherein the linker is a straight chain or branched C3-C6-alkylene.

9. The modified pH indicator of claim 8, having a 2-aminoethyl group or a 3-carboxy-n-propyl group.

10. The modified pH indicator compound of claim 1 represented by Formula I


wherein R1, R2 and R3 for each compound are set forth in Table 2,

Table 2


.

11. The modified indicator compound of claim 1 represented by Formula (II),

where the combinations of R1, R2 and R3 are as set forth in the table below,

and one of R4 and R5 is hydrogen and the other is NH2-linker or HOOC-linker-;

wherein the linker is a bivalent chemical moiety.

12. The modified pH indicator compound of claim 11, wherein the linker is a straight chain or branched C1-C6-alkylene.

13. The modified pH indicator compound of claim 11, wherein one of R4 and R5 is hydrogen and the other is 2-aminoethyl or 3-carboxy-n-propyl.

14. The modified pH indicator compound of claim 11 represented by one of Formulas (IIa) and (IIb),

15. The modified pH indicator compound of claim 1, wherein said compound is fluorescent.

16. The pH indicator compound of claim 15 having the structure


wherein M+ is a cation.

17. A method of producing a composition comprising a pH modified indicator compound covalently attached to a substrate, comprising reacting a substrate having aromatic groups, hydroxyl groups, amino groups, carboxyl groups or a combination thereof, with a modified pH indicator compound of any one of claims 1 to 16.

18. The method of claim 17, wherein the substrate is a polymer.

19. The method of claim 18, wherein the polymer is hydroxylated.

20. The method of claim 19, wherein the polymer is selected from cellulose, cellulose derivatives, polyvinyl alcohol, derivatives of polyvinyl alcohol, polyallyl alcohol and derivatives of polyallyl alcohol.

21. The method of claim 18, wherein the polymer comprises aromatic groups.

22. The method of claim 21, wherein the polymer is polyethylene terephthalate or polystyrene.

23. A method of producing a substrate having on its surface a polymerized or oligomerized pH indicator compound, comprising the step of polymerizing or oligomerizing a pH indicator compound in the presence of the substrate.

24. The method of claim 23, wherein the pH indicator compound is polymerized or oligomerized by reaction with formaldehyde.

25. The method of claim 24, wherein the pH indicator compound is a sulfonepthalein dye.

26. The method of claim 25, wherein the sulfonephthalein dye is selected from the group consisting of phenol red, cresol red, m-cresol purple, xylenol blue, thymol blue, chlorophenol red, bromophenol blue, bromocresol purple, bromocresol green, bromothymol blue, xylenol orange, and methylthymol blue.

27. The method of claim 26, wherein the sulfonephthalein dye is selected from the group consisting of phenol red, cresol red, m-cresol purple, xylenol blue, thymol blue, chlorophenol red, and xylenol orange.

28. A composition comprising a modified pH indicator compound covalently attached to a substrate, said composition being produced by the method of any one of claims 17-27.

29. A device comprising the composition of claim 28 and an automated reader or a reflectance spectrophotometer.

30. The device of claim 29, wherein the automated reader comprises an RBG detector.

31. A method of monitoring the pH of a recreational water source, comprising contacting the water with the device of claim 29 or 30 and monitoring the pH of the water.