Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – Specific organic component
Reexamination Certificate
2000-06-20
2001-10-16
Hardee, John (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
Specific organic component
C510S493000, C562S074000, C568S033000
Reexamination Certificate
active
06303562
ABSTRACT:
BACKGROUND OF THE INVENTION
Surfactants are amphiphilic compounds comprising a polar or ionic head group and a hydrophobic tail. Anionic surfactants have important commercial applications as wetting agents, detergents, oil additives and enhanced oil recovery agents. Anionic sulfonate surfactants are a commercially important class of detergents. Surfactants used in enhanced oil recovery processes also typically have sulfonate or sulfate polar head groups due to the aqueous solubility of such compounds in the presence of hard cations often present in such environments, such as Mg
2+
and Ca
2+
. Such surfactants include alkylsulfonates, alkylarylsulfonates and petroleum sulfonates. More recently, the development of surfactant-based enhanced oil recovery methods has slowed dramatically, due, in part, to high surfactant costs. As a result, the development of low-cost surfactants derived from waste products, such as lignin, has been an active area of research in the petroleum industry.
Aromatic sulfonates, such as toluene sulfonate and cumene sulfonate, find application as hydrotropes, substances that increase the aqueous solubility of a material which otherwise has only limited aqueous solubility. Current research in the area of hydrotropes is focused on the development of materials having multifunctional properties.
Environmental concerns in regard to biodegradability and toxicity, as well as a desire for multifunctional compositions has driven research directed toward the development of new surfactants for detergents and other applications. There is, thus, a need for new, inexpensive starting materials for the preparation of surfactants, particularly surfactants which are suitable for use in an enhanced oil recovery process.
SUMMARY OF THE INVENTION
In one embodiment, the present invention relates to a composition which consists essentially of a 2-(2-hydroxyphenyl)benzenesulfinic acid or 2-(2-hydroxyphenyl) benzenesulfonic acid which is independently substituted at one or more ring positions by a substituted or unsubstituted linear, branched or cyclic C
1
-C
24
-alkyl, aryl or alkylaryl group. The substituted 2-(
2
-hydroxyphenyl)benzenesullinic acid or 2-(2-hydroxyphenyl) benzenesulfonic acid can also be present in the composition as a salt with one or more cations, as the corresponding sultine or sultone, or as a combination of two or more of the acid, salt and the sultine or sultone. The invention also includes a solution which consists essentially of a solvent and one of these substituted 2-(2-hydroxyphenyl) benzenesulfinic acid, 2-(2-hydroxyphenyl)benzenesulfonic acid, salts, sultines or sultones, or a combination thereof, dissolved therein.
In another embodiment, the invention relates to a 2-(2-hydroxyphenyl) benzenesulfinic acid or 2-(2-hydroxyphenyl)benzenesulfonic acid which is independently substituted at one or more ring positions by a linear, branched or cyclic, substituted or unsubstituted C
6
-C
24
-alkyl group and the remaining ring positions are independently unsubstituted or substituted by a linear or branched substituted or unsubstituted C
1
-C
5
-alkyl group. The compound can also exist as a salt with a cation or as the corresponding sultine or sultone.
In a further embodiment, the invention relates to compositions which consist essentially of two or more compounds selected from among 2-(2-hydroxyphenylbenzenesulfinic acid, substituted 2-(2-hydroxyphenyl)benzenesulfinic acids, 2-(2-hydroxyphenyl)benzenesulfonic acid and substituted 2-(2-hydroxyphenyl) benzenesulfonic acids, salts thereof, and sultines and sultones corresponding thereto. Suitable substituents can be present at one or more positions on either aromatic ring of the biphenyl nucleus, and include straight chain, branched or cyclic, substituted or unsubstituted C
1
-C
24
-alkyl groups, substituted and unsubstituted aryl groups, substituted and unsubstituted arylalkyl groups.
The present invention also provides a solution which consists essentially of a solvent and two or more compounds dissolved therein selected from among 2-(2-hydroxyphenylbenzenesulfinic acid, substituted 2-(
2
-hydroxyphenyl)benzenesulfinic acids, 2-(2-hydroxyphenyl)benzenesulfonic acids and substituted 2-(2-hydroxyphenyl) benzenesulfonic acids, salts thereof and sultines and sultones corresponding thereto, as described above.
In yet another embodiment, the invention relates to a method of alkylating substituted or unsubstituted 2-(2-hydroxyphenyl)benzenesulfinic acid or substituted or unsubstituted 2-(2-hydroxyphenyl)benzenesulfonic acid. The method comprises the step of reacting a substituted or unsubstituted 2-(2-hydroxyphenyl)benzenesulfinic acid or substituted or unsubstituted 2-(2-hydroxyphenyl)benzenesulfonic acid, with an alkene or substituted alkene under conditions suitable for alkylation of one or more ring positions of the 2-(2-hydroxyphenyl)benzenesulfinic acid or 2-(2-hydroxyphenyl) benzenesulfonic acid, thereby alkylating one or more ring positions of the 2-(2-hydroxyphenyl)benzenesulfinic acid or 2-(2-hydroxyphenyl)benzenesulfonic acid.
The present compositions can be used as hydrotropes and are also of use as, or as starting materials for, surfactants, and as starting materials for the synthesis of other useful chemicals such as, polymers and resins, solvents, adhesives and biocides.
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Lange Elaine A.
Lin Qun
Enchira Biotechnology Corporation
Hamilton Brook Smith & Reynolds P.C.
Hardee John
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