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US 5,633,221 AGranted
Silicone containing imidazoline compositions
AssigneeMona Industries, Inc.
InventorsDennis L. Fost, Abe Berger
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AssigneeMona Industries, Inc.
InventorsDennis L. Fost, Abe Berger
Estimating the term…
A method is provided for preparing silicone-containing compositions represented by the formula: ##STR1## wherein: R is a organosilicone chain represented by the formula: ##STR2## wherein: R.sub.5, which can be the same or different, is selected from R.sub.6, at least one group of the --(CH.sub.2).sub.n1 --B.sub.n2 --(CH.sub.2).sub.n3 -- and mixtures thereof: R.sub.6 is selected from alkyl, aryl and olefin; R.sub.7 and R.sub.8, are selected from alkyl, aryl, polyoxyalkylene, alkaryl, aralkylene, and alkenyl; R.sub.1 is of the group consisting of hydrogen and lower alkyl; R.sub.2 is hydrogen or an alkylene hydrocarbon group; and R.sub.3 is selected from --OH, --NH.sub.2, --R.sub.9 CONH--R.sub.9 COO and --H, wherein R.sub.9 is alkyl having from 1 to 22 carbon atoms. Wherein an organosilicone fluid having at least one carboxyl-functional group is reacted with a substituted or unsubstituted alkyl ethylene diamine compound at an elevated temperature for a time necessary to react the carboxyl functional group and provide for the cyclization of the reaction product.
A method for readily preparing silicone-containing imidazoline compositions having effective surface active, substantively, corrosion inhibition and lubrication properties which comprises reacting an organosilicone fluid or composition having at least one terminal, lateral or combination of terminal and lateral carboxyl functional groups with at least a stoichiometric amount of an alkyl, hydroxyalkyl, and/or aminoalkyl ethylene diamine compound at an elevated temperature, for a time necessary to react the carboxyl functional group and provide for the cyclization of the reaction product.
Dependencies are inferred from the claim text.
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Containing silicones: nitrogen containing silicones
Containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate: containing nitrogen, e.g. amodimethicone,…
Preparations for care of the skin
Compounds having one or more O-Si linkage: compounds with one or more Si-O-Si sequences
Term ended 12 Sep 2014 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
The present invention relates to novel imidazoline compositions and, more particularly, to silicone containing imidazoline compositions and to methods for preparing the same.
The production and marketing of imidazolines and various derivatives thereof has been carried on for a number of years. Such compositions have been widely used as surface active agents, metal treating compounds and a variety of other applications. Imidazolines are commonly prepared by condensing, under conditions of heating and stirring, a long chain aliphatic monocarboxylic or fatty acid or a source thereof such as amides (or esters of such acids) with an alkyl, hydroxyalkyl and/or aminoalkyl ethylene diamine derivative, such as hydroxyethyl ethylene diamine.
Organosiloxane compositions including carboxylfunctional siloxane and other silicone compositions which exhibit excellent properties as surface active agents, lubricants and the like are also known and have been used commercially over the years. While a variety of imidazoline and polysiloxane compositions and derivatives thereof are known, to the best of our knowledge there has been no disclosure or suggestion of the novel silicone-containing imidazoline compositions and methods for preparing the same herein described.
The invention is further illustrated by the following examples which are not to be considered as limitative of its scope.
A Trimethylsilyl capped carboxypropyl containing silicone fluid obtained from Shin-Etsu under the trade designation X-22 371 is used in this example. The silicone fluid contains 8.01% carboxyl groups (number of grams of fluid/carboxyl group=561.79).
134.8 grams (0.24 equivalent weight) the silicone fluid and 31.5 grams of aminoethyl ethanolamine (0.3 mole) are charged to a reaction vessel and heated to about 150.degree. under nitrogen whereupon volatiles begin distilling off. The reaction mixture is heated for 3 hours over which time 14.5 ml of volatiles are collected which separates into 2 layers. The bottom layer of 4 ml is water. The alkali number of the reaction mixture at this time is 121.9 (theory 121.3).