Silicone reactive/fluorescent silane dye compositions

• US 4,746,751 A
• Filed: 05/07/1987
• Issued: 05/24/1988
• Est. Priority Date: 05/07/1987
• Status: Expired due to Fees

• Current Assignee: Baxter Travenol Laboratories Incorporated
• Original Assignee: Baxter Travenol Laboratories Incorporated
• Inventors: Oviatt, Henry W. Jr., Reich, Cary J.
• Primary Examiner(s): NOT, DEFINED
• Assistant Examiner(s): Rodriguez, Isabelle
• Application Number:
  US07/047,690
• Time in Patent Office: 383 Days
• Field of Search: 556/435, 556/413, 556/442
• US Class Current: 556/456
• CPC Class Codes: C07F 7/0805 comprising only Si, C or H atoms
• CPC Class Codes: C07F 7/1804 Compounds having Si-O-C linkages Si-O-acyl linkages C07F7/1896
• CPC Class Codes: C08K 5/54 Silicon-containing compounds C08K5/0091 takes precedence
• CPC Class Codes: C08L 83/04 Polysiloxanes
• CPC Class Codes: C09B 69/008 Dyes containing a substituent, which contains a silicium atom

Abstract

The preparation of particular fluorescent silane dye compositions is disclosed. These silane dye compositions have particular utility as reactants in the preparation of silicone polymeric fluorescent dyes which can be ideally used as chemical indicators in biological sensors.

Claims

1. A silane dye composition having the formula ##STR14## wherein Q is a fluorescent dye group;

Z is a C_1-30 hydrocarbon radical;

R is a hydrogen atom or a C_1-12 hydrocarbon radical; and

G is a functional group capable of reacting with a silicone polymer functional group.

2. The composition of claim 1 wherein G is an unsaturated organic functional group selected from the class of vinyl, alkyl, methallyl, or butenyl radicals.

3. The composition of claim 1 wherein Q is a fluorescent dye selected from the group of polynuclear aromatic dyes composed of pyrene, perylene, benzopyrlene and derivatives thereof.

4. The dye composition of claim 1 wherein G is a radical of the formula ##STR15## where R is a hydrogen atom or a C_1-12 hydrocarbon radical;

n is a whole number of from 1 to 50; and

V₁, V₂ and V₃ are independently a silicone polymer reactive substituent.

5. The composition of claim 4 wherein the V₁, V₂ and V₃ silicone polymer reactive groups are selected from the class of radicals consisting of alkoxy, acyloxy or amine groups.

6. The composition of claim 1 comprising methyl(pyrenyl)dimethylvinyl silane.

7. The composition of claim 5 comprising methyl(pyrenyl)dimethylethyl(triethylsiloxy)silane.

8. A method of preparing a dye-silane composition comprising reacting a substituted polynuclear aromatic hydrocarbon based fluorescent dye of the formula:

space="preserve" listing-type="equation">Q-Z-M

wherein Q is a polynuclear aromatic fluorescent dye moiety, Z is a C_1-30 hydrocarbon radical, and M is a silane reactive substituent selected from the group consisting of halogen, hydroxyl, carboxyl, amine, and amide groups;

with an unsaturated organo functional silane having the formula;

##STR16## wherein X is selected from the group of hydrogen, hydroxyl, and halogen radicals;

R is a hydrogen atom or a C_1-12 hydrocarbon radical and A is an alkenyl group to form the dye silane of the formula ##STR17##

9. The process of claim 8 wherein the resulting unsaturated organo silane dye is further reacted with a hydride functional silane of the formula:

##STR18## in an addition reaction with the unsaturated A group to form ##STR19## wherein n is a whole number from 1 to 50 and V₁ V₂ and V₃ are independently a silicone polymer reactive substituent selected from the class consisting of alkoxy, acyloxy and amine radicals.

10. The process of claim 8 wherein the alkenyl group A is selected from the group consisting of vinyl, allyl, methallyl, and butenyl radicals.

11. The process of claim 8 wherein the product formed is methyl(pyrenyl)dimethylvinyl silane.

12. The process of claim 9 wherein the product formed is methyl(pyrenyl)dimethylethyl(triethylsiloxy)silane.