| PATENT NUMBER | This data is not available for free |
| PATENT GRANT DATE | January 3, 1995 |
| PATENT TITLE |
Fluorescent monomer and polymer |
| PATENT ABSTRACT | 3-Hydroxy-2-methylene-3-(1-naphthyl)propionic acid, methyl ester and fluorescent water soluble polymers prepared therefrom |
| PATENT INVENTORS | This data is not available for free |
| PATENT ASSIGNEE | This data is not available for free |
| PATENT FILE DATE | November 4, 1993 |
| PATENT REFERENCES CITED |
R. M. Lawrence and P. Perlmutter, Chemistry Letters No. 2, pp. 305-308, 1992. DABCO-Catalyzed Coupling of Aldehydes with Activated Double Bonds, Hoffman et al, J. Org. Chem., 1985, pp. 3849-3859. |
| PATENT CLAIMS |
We claim: 1. A water soluble polymer from the group consisting of acrylic acid, acrylamide and mixtures thereof, which contains from 0.1-2.0 mole % of 3-Hydroxy-2-methylene-3-(1-naphthyl)propionic acid, methyl ester said water soluble vinyl polymer having been prepared by vinyl addition polymerization. 2. The water soluble vinyl polymer of claim 1 where the water soluble vinyl monomer is acrylic acid. 3. The water soluble vinyl polymer of claim 1 where the water soluble vinyl monomer is acrylamide |
| PATENT DESCRIPTION |
INTRODUCTION Polymers tagged with pendant fluorescent groups are generally easily monitored, even when present at low concentrations. Highly fluorescent molecules, that is, molecules which have a fluorescent quantum efficiency, or fluorescent quantum yield, within the range of from about 0.1 to about 1.0 and a light absorbance molar extinction coefficient of at least 1,000 are typically detectable at concentration ranges of parts per million ("ppm") to parts per billion ("ppb") or even less. The incorporation of such a highly fluorescent species into a polymer in the amount of one weight percent (based on polymer actives) will permit the detection of such polymer at polymer concentration levels down to 0.1 ppm or less, provided the fluorescent quantum yield and the light absorbance molar extinction coefficient of the fluorescent tagging agent are not significantly adversely affected by its attachment to the polymer. There are several methods for tagging water soluble polymers. Such methods are described in U.S. Pat. Nos. 5,128,419 and 5,043,406. The disclosures of these patents are incorporated herein by reference. A preferred method for incorporating fluorescent moieties into water soluble polymers is by copolymerization of an appropriate water soluble vinyl monomer with a vinyl compound possessing fluorescent properties. Illustrative of such a procedure is disclosed in U.S. Pat. No. 5,043,406. In this patent, a fluorescent monomer is copolymerized in small amounts with acrylic acid, acrylamide or copolymers thereof to provide tagged water soluble polymers. The major drawback to this method of tagging water solubility is the availability of easily prepared fluorescent vinyl monomers. If such a monomer were available, it would be possible to inexpensively and simply prepare tagged water soluble polymers. THE INVENTION The invention provides to the art the new fluorescent vinyl monomer, 3-Hydroxy-2-methylene-3-(1-naphthyl)propionic acid, methyl ester. The invention also relates to the incorporation of 3-Hydroxy-2-methylene-3-(1-naphthyl)propionic acid, methyl ester into acrylic acid, acrylamide and copolymers of these two monomers. The amount of 3-Hydroxy-2-methylene-3-(1-naphthyl)propionic acid, methyl ester incorporated into such polymers may be within the range of 0.1-2.0 mole percent. PREPARATION OF 3-Hydroxy-2-methylene-3-(1-naphthyl)propionic acid, methyl ester The reaction of activated bonds with aldehydes using 1,4-diazabicyclo [2,2,2] octane, DABCO, was reported by Hoffmann and Rabe, J. Org. Chem., 1985, 50, 3849-3859. This article is incorporated herein by reference. 3-Hydroxy-2-methylene-3-(1-naphthyl)propionic acid, methyl ester is readily prepared by the reaction of 1-naphthaldehyde with a lower acrylate ester such as methylacrylate. Other acrylate esters such as ethylacrylate and the like may be used. The amount of acrylate ester should be in molar excess, 0.5-2 moles, in relation to the 1-naphthaldehyde. The reaction is conducted using a catalyst soluble in the acrylate ester. A preferred catalyst is DABCO. Minor amounts of the catalyst eg. 0.05 to about 3% usually produces good yields. The reaction is preferably conducted at about room temperature eg. 24 degrees C plus or minus 5 degrees. The use of elevated temperatures is not desirable since it increases unwanted side reactions. Since room temperature is used the reaction requires from about 8 hours up to several days or more to produce substantial yields of 3-Hydroxy-2-methylene-3-(1-naphthyl)propionic acid, methyl ester. |
| PATENT EXAMPLES | available on request |
| PATENT PHOTOCOPY | available on request |
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