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US 5,384,411 AGranted
Immobilization of PH-sensitive dyes to solid supports
AssigneeHewlett-Packard Company
InventorsKarla M. Robotti, Carl A. Myerholtz
Life of this patent
Estimating the term…
Abstract
Disclosed are pH dyes containing a suitable compatible substituent which permits binding of the dye to a solid support. Also disclosed are methods for synthesizing such dyes prior to their coupling to the solid supports.
Claims12
A compound represented by either formula I, II or III:
- ##STR16## wherein R is ##STR17## wherein p is an integer equal to zero or one;
- q is an integer equal to zero or one;
- R.sub.6 is hydrogen or an alkyl group of from 1 to about 6 carbon atoms;
- R.sub.7 is an alkylene group of from 1 to about 6 carbon atoms;
- Z is a reactive functionality selected from the group consisting of carboxylic acid groups, amine groups, hydroxyl groups, unsaturated aliphatic groups of 2 carbon atoms, and epoxides;
- and t is an integer equal to at least 1;
- each R.sub.1 is hydrogen;
- each Ar is independently a 4-hydroxyphenyl or 4-hydroxynapthyl group having from 0 to 3 compatible substituents selected from the group consisting of alkyl of from 1 to 6 carbon atoms, halo and nitro;
- and X is >C.dbd.O or >SO.sub.2.
6 more elements
A compound of the formula:
- ##STR18## wherein X, Y and Z are independently hydrogen or methyl or Y and Z are linked to form a second phenyl ring so as to form a naphthyl substituent.
A compound of the formula:
- ##STR19## wherein X and Z are independently selected from the group consisting of hydrogen, chloro, bromo, and alkyl of from 1 to 6 carbon atoms.
A process for the preparation of compounds of the formula VII:
- ##STR20## wherein R is ##STR21## wherein p is an integer equal to zero or one;
- q is an integer equal to zero or one;
- R.sub.6 is hydrogen or an alkyl group of from 1 to about 6 carbon atoms;
- R.sub.7 is an alkylene group of from 1 to about 6 carbon atoms;
- Z is a reactive functionality selected from the group consisting of carboxylic acid groups, amine groups, hydroxyl groups, unsaturated aliphatic groups of 2 carbon atoms, and epoxides;
- and t is an integer equal to at least 1;
- each R.sub.1 is hydrogen;
- each Ar is independently a 4-hydroxyphenyl or 4-hydroxynapthyl group having from 0 to 3 compatible substituents selected from the group consisting of alkyl of from 1 to 6 carbon atoms, halo and nitro;
- and X is either >C.dbd.O or >S(O).sub.2 ;
- which method comprises combining a compound of the formula VIII:
- ##STR22## with at least 2 molar equivalents of a phenol or 1-naphthol having from 0 to 3 compatible substituents selected from the group consisting of alkyl of from 1 to 6 carbon atoms, halo and nitro and with the proviso that there are no such substituents at the 4 position of the phenol and the 1-naphthol, at a temperature of from about 40.degree. C. to about 250.degree. C. in the presence of from about 5 to about 20 weight percent of a compound selected from the group consisting of ZnCl.sub.2, H.sub.2 SO.sub.4 and SnCl.sub.4 so as to form a compound of the formula IX:
- ##STR23## wherein Ar and R.sub.1 are as defined above and R.sub.5 is R or a group capable of being derivatized to R wherein R is as defined above;
- and when R.sub.5 is a group capable of being derivatized to R, said R.sub.5 group is derivatized under conditions sufficient to convert this group to ##STR24## wherein R.sub.6, R.sub.7, Z, p and q are as defined above.
10 more elements
A process for the preparation of compounds of the formula X or XI:
- ##STR25## wherein R is ##STR26## wherein p is an integer equal to zero or one;
- q is an integer equal to zero or one;
- R.sub.6 is hydrogen or an alkyl group of from 1 to about 6 carbon atoms;
- R.sub.7 is an alkylene group of from 1 to about 6 carbon atoms;
- Z is a reactive functionality selected from the group consisting of carboxylic acid groups, amine groups, hydroxyl groups, unsaturated aliphatic groups of 2 carbon atoms, and epoxides;
- and t is an integer equal to at least 1;
- each R.sub.1 is hydrogen;
- each Ar is independently a 4-hydroxyphenyl or 4-hydroxynapthyl group having from 0 to 3 compatible substituents selected from the group consisting of alkyl of from 1 to 6 carbon atoms, halo and nitro;
- and X is either >C.dbd.O or >S(O).sub.2 ;
- which method comprises combining a compound of either formula XII or XIII:
- ##STR27## with at least 2 molar equivalents of a phenol or 1-naphthol having from 0 to 3 compatible substituents selected from the group consisting of alkyl of from 1 to 6 carbon atoms, halo and nitro and with the proviso that there are no such substituents at the 4 position of the phenol and the 1-naphthol, at a temperature of from about 40.degree. C. to about 250.degree. C. in the presence of from about 5 to about 20 weight percent of a compound selected from the group consisting of ZnCl.sub.2, H.sub.2 SO.sub.4 and SnCl.sub.4 so as to form a compound of either the formula XIV or XV:
- ##STR28## wherein Ar and R.sub.1 are as defined above and R.sub.5 is R or a group capable of being derivatized to R wherein R is as defined above;
- and when R.sub.5 is a group capable of being derivatized to R, said R.sub.5 group is derivatized under conditions sufficient to convert this group to ##STR29## wherein R.sub.6, R.sub.7, Z, p and q are as defined above.
10 more elements
Dependencies are inferred from the claim text.