Polymerization method by dielectric heating of unsaturated...

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...

Reexamination Certificate

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C522S186000, C522S188000

Reexamination Certificate

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06656980

ABSTRACT:

Process of polymerization by dielectric heating of unsaturated fatty acids, esters of unsaturated fatty acids, unsaturated hydrocarbons, or unsaturated derivatives of these products.
This invention relates to a process of polymerization of unsaturated fatty acids, esters of unsaturated fatty acids, unsaturated hydrocarbons or esters of unsaturated hydrocarbons, or unsaturated derivatives of these products by dielectric heating, as well as to the polymers obtained and uses of these polymers, that is, heating at microwave frequencies or radio frequencies.
Compounds obtained by polymerization of fatty acids or of esters of unsaturated fatty acids are well known. The polymers obtained on the basis of unsaturated vegetable oil, in particular, may be cited. Polymerization processes make use of double bonds of fatty acids or, after initial treatment (isomerization), conjugate bonds.
Current processes for preparation of these polymers such as blown oils or stand oils are characterized by use of heat (thermal polymerization) in the presence of catalysts (homogenous or heterogenous). Use of catalysts such as oxygen or anthraquinone makes it possible to obtain polymers of high viscosity but ones which are highly reactive after their preparation, a feature of interest only for areas of application such as paints in which the product is required to dry (reticulation phenomenon).
In areas such as lubrication, cosmetics, or pharmacology, on the other hand, there is a demand rather for polymers stable under external restraints (oxygen, water, etc). The restraint of eliminating traces of catalysts is sometimes added in cosmetics and in pharmacology.
Polymers have been developed on the basis of this fact: they are prepared on the basis of triglycerides at least one fatty acid of which comprises at least one unsaturated compound (conjugate or not), preferably without a catalyst and in an atmosphere devoid of oxygen. These developments use processes such as heating belts, gilotherms [heat transfer fluids], or resistors, which processes take much time, something which generally prevents obtaining polymers exhibiting high viscosities; they are also costly because of the investment amounts required.
The invention makes it possible to reduce these major disadvantages. Use of microwaves or radio frequencies yields dual benefits; on the one hand the microwave or high-frequency energy interacts immediately at the molecular level, and on the other less energy is required (it is the molecules themselves which, when polarized by the electric fields of the microwaves or radio frequencies, convert electromagnetic energy to heat).
The applicant has found, as a first feature of the invention, that polymerization of unsaturated fatty acids, of unsaturated hydrocarbons, of unsaturated derivatives of these products, or of a mixture of them by dielectric heating, that is, by means of microwaves or radio frequencies, preferably microwaves, makes it possible to obtain high-viscosity products with more favorable reaction periods.
Hence the invention relates to the general process of polymerization of unsaturated fatty acids, unsaturated fatty acid esters, unsaturated hydrocarbons, and similar products, by dielectric heating, that is, by means of microwave frequencies or radio frequencies, preferably microwaves.
Use of microwave energy in industry is already known, but in a different field and to cope with different problems, especially in the area of epoxy resins and the like.
Microwaves or radio frequencies have not been described for polymerization of products of the kind described above, and of squalene in particular.
Nor has a description been given of the possibility of replacement of use of squalane in cosmetics by a polymer of squalene obtained at lower cost by the process claimed for the invention.
The gain in time and energy combined with lower investment cost permits the assertion that the dielectric heating process is faster and more cost effective.
This invention may be applied for polymerization of unsaturated fatty acids, esters of unsaturated fatty acids, unsaturated hydrocarbons, plant oils, animal oils and fats, and their unsaturated derivatives. These products may be used in raw or refined form, optionally after undergoing preliminary treatment.
The reaction may involve a single reagent or a mixture of reagents in varying proportions.
Polymerization is carried out by subjecting the reagent or reagents to dielectric heating, that is, heating at frequencies ranging from around 30 Ghz to around 3 MHz. Microwave frequencies, which are preferred, range from around 30 GHz to around 300 MHz, preferably 2.45 Ghz (authorized frequency with 2-percent tolerance) or 915 MHz (authorized frequency with 1.4-percent tolerance). The radio frequencies range from around 300 MHz to around 3 MHz, preferably 13.56 MHz (authorized frequency with 0.05-percent tolerance) or 27.12 MHz (authorized frequency with 0.6-percent tolerance).
The reaction temperatures range from 200 to 400° C., by preference 230 to 350° C., with a temperature rise of three to 60 minutes, by preference three to 20 minutes, over a total reaction period of 15 minutes to 15 hours, preferably 15 to 360 minutes, by preference 15 to 120 minutes, with or without catalyst, preferably without catalyst, under constant agitation, in an inert atmosphere or not, depending on the result desired.
The polymerization reagents for this invention may be chosen from among animal and plant oils and fats and from among the polyterpenes some of which are derived from the oils and fats in question.
Sperm whale oil, dolphin oil, whale oil, seal oil, sardine oil, herring oil, shark oil, cod liver oil, neat's-foot oil and fats of beef, pork, horse, and sheep (tallow) may be cited as oils or fats of animal origin.
As oils of plant origin one may mention, among others, rapeseed oil, sunflower oil, peanut oil, olive oil, walnut oil, corn oil, soya oil, flaxseed oil, hemp oil, grapeseed oil, coconut oil, palm oil, cottonseed oil, babassu oil, jojoba oil, sesame oil, castor oil, dehydrated castor oil, hazelnut oil, wheat germ oil, borage oil, primrose oil, tall oil.
Use may also be made of the components of animal or plant oils such as scalene extracted from the nonsaponifiable components of plant oils (olive oil, peanut oil, rapeseed oil, corn germ oil, cottonseed oil, flaxseed oil, rice bran oil) or contained in large amounts in shark oil.
As unsaturated fatty acids use may be made, singly or in mixture, as nonrestrictive examples, of one or more of monounsaturated fatty acids such as oleic acid, palmitoleic acid, myristic acid, petroselenic acid, erucic acid, etc; one or more of polyunsaturated fatty acids such as linoleic acid, alpha-linoleic and gamma-linoleic acids, arachidonic acid; one or more of acids comprising conjugate dienes or conjugate trienes such as licanic acid or the isomers of linoleic or linolenic acids; one or more of the acids comprising one or more hydroxyl groups such as ricinoleic acid.
As esters of unsaturated fatty acids use may be made, singly or in mixture, as nonrestrictive examples, of one or more of the esters obtained by esterification between a monoalcohol and/or a polyol (singly or in mixture), and at least one unsaturated fatty acid. As nonrestrictive examples of monoalcohol mention may be made of methanol, ethanol, or butanol; as nonrestrictive examples of polyols, glycerol, sorbitol, neopentylglycol, trimethylpropane, pentaerythritol, glycol, ethylene glycol, polyethylene glycol. Waxes and phospholipids may also be used as fatty acid esters.
As unsaturated hydrocarbons use may be made, singly or in mixture, as nonrestrictive examples, of one or more of the terpenic hydrocarbons, oxygenated or not, that is, one or more isoprene polymer, one or more isobutene polymer, styrene, ethylene, butadiene, isoprene, propene, or one or more of the copolymers of these alkenes.
Unsaturated derivatives of these compounds may be obtained, for example, by activation of residual unsaturated compounds by any method known to the expert, such as hy

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