Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Reexamination Certificate
1999-05-10
2002-04-02
Carr, Deborah D. (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
51, 51, C554S229000, C424S059000, C424S060000, C424S064000, C424S073000
Reexamination Certificate
active
06365629
ABSTRACT:
The present invention is directed to fatty acid acid esters of monohydric aromatic alcohols and their use as “dry” emollients and their solvency characteristics for active ultra-violet absorbers and dispersibility and anti-agglomeration properties for inorganic sunblocks with resultant increase in SPF values of cosmetic formulations.
BACKGROUND OF THE INVENTION
Over the years, numerous esters have been commercially prepared from fatty alcohols and fatty acids ranging in chain lengths from C
1
to C
50
and have been successfully used as emollients, solubilizers, clarifying agents, pearlescing agents, dispersants, sunscreens, coupling agents, emulsifying agents, viscosity building agents, opacifying agents, conditioning agents, defoliants, anti-irritants, tackifiers, detackifiers, spreading agents, blooming agents, slip additives, glossifying agents, spreading agents, melting point depressants, etc. Generally speaking, esters have been prepared by direct esterification between an alcohol and an acid using either an acid or basic catalyst; esters have also been prepared by transesterification between two esters or by transesterification under either basic or acid catalysis of oils with various alcohols to produce the resultant ester.
Esters have been derived from purely naturally occurring raw materials such as triglycerides of coconut, sunflower, safflower, soybean, babbasu, rapeseed, canola, mink, tallow, lard oil, apricots, etc. Esters have also been derived and used in the cosmetic, toiletry as well as the personal care area from purely derived synthetic sources such as Isopropanol, Butanol, 2-Ethylhexanol, Isodecanol, Isononyl Alcohol, Tridecanol, Isocetyl Alcohol, Isostearyl Alcohol, Octadecanol, C
20
+Alcohols and may be linear, isomeric or branched in character and have been monohydric. Esters have also been produced and used on a commercial basis in the cosmetic, toiletry and personal care industries based on diols, triols, tetraols and various polyols such as sugars and sorbitols reacted with acids ranging in chain lengths from C
1
through C
50
. Similarly, esters have been produced from dimer, trimer, tetra as well as Polycarboxylic Acids with alcohols ranging from C
1
to C
50
. Esters have also been prepared from Alkoxylated Alcohols and Alkoxylated Acids to yield emulsifiers with various degrees of water and oil insolubility/solubility commonly referred to as HLB.
Similarly, esters from alfa as well as beta-hydroxyacids have been prepared and used primarily as defoliating agents for the skin and conditioning agents for the hair. Lauryl Lactate, for example has been found to serve as a vehicle for transporting active drugs through the skin.
Esters of Salicylic Acid have been used as sunscreens and also have been used as sunscreen synergists as well as defoliants for the skin. Esters have also been prepared from derivatives of Cinnamyl derivatives, i.e, Octylmethoxy Cinnamate and 2-Ethyl Hexanol ester of p-Dimethylamino Benzoic Acid for use as sunscreen to effectively aborb UV light.
Esters, derived from Benzoic Acid, have been prepared and commercially used in the cosmetic, toiletry and personal care industry. Typical examples here are the well-known C
12
-C
15
ester of Benzoic Acid as well as the Benzoic Acid ester of Glycereth-7. Esters have also been used in the cosmetic, toiletry and personal care areas as preservatives such as methyl, propyl and butyl esters of p-amino Benzoic Acid and solutions of these esters and Phenoxyethanol and similar solvents.
Esters derived from pentaerithritol are also used in the cosmetic, toiletry and personal care areas. These esters are tetra-functional and are known for their lubricity characteristics inasmuch as they can be defined structurally as simulating “ball-bearings”. In essence, they tend to be circular rather than linear as are most esters.
Linear esters tend to exhibit characteristics of “slip and slide”. Esters of lactic acid are known for the spreading properties. Esters derived from unsaturated or partially unsaturated isoalcohols or isoacids tend to exhibit liquidity at ambient temperatures making them easy to work with in actual production circumstances.
Esters have been prepared from ethoxylated alcohols and acids, linear or isomeric, and have been found to function as excellent emulsifiers. By varying the degree of ethoxylation of either the alcohol or acid and the ultimate esterification of the terminal hydroxyl group, it is possible to achieve a wide spread of HLB values. Esters prepared from propoxylated alcohols or acids have been found to “yield” emolliency; however, such emollients tend to be quite heavy with “drag”.
Esters, therefore, serve many different aspects in the cosmetic, toiletry and personal care areas and find use in numerous applications. Esters produced from Dimer Acids or Dimer Alcohols are primarily known for their anti-irritating characteristics when employed in a formulation. However, they tend to be quite “heavy”.
Esters prepared from Adipic Acid, Azaleic Acid, Dodecanedioic Acid, Sebacic Acid and Maleic Acid tend to yield esters with good low temperature characteristics. However, most of these esters are quite “heavy” with the exception of Diisopropyl Adipate because of the use of di-alcoholic groups of isopropanol yields a “light” ester and has found use in deodorants and bath products. Further, being based on rather low cost raw materials, i.e., Adipic Acid and Isopropanol, it is more than reasonably priced for large use commodity products sold in the cosmetic, toiletry and personal care market. In essence, esters can be prepared from mono-, di-, tri-, tetra- or poly-functional acids of alcohols and can serve many useful purposes in the cosmetic, toiletry and personal care areas as defined below:
Emolliency
Emulsification
Conditioning
Defoliation
Blooming Agent
Clarification
Dispersion
Coupling
Solubilization
Freeze Point Depressant
Spreading Agent
Gloss Enhancing
Tackifying
De-tackifying
Slip Additive
Anti-irritant
Solvent for Sunscreens/Other Active Ingredients
Insect Repellents
Vehicles for Inorganic Sunscreens
Esters have been used to replace naturally occurring oils and waxes; i.e., Spermacetic wax and sperm oil have been successfully used for years via esters such as Cetyl Myristate, Cetyl Palmitate and mixed cetyl esters, thereby saving the whale. Synthetics such as octyldodecyl erucate have successfuly replaced jojoba oil, which has been known to vacillate in price due to changes in weather.
Of all of the esters elucidated above, none have been derived from aromatic alcohols such as benzyl or phenoxyethanol in the cosmetic, toiletry and personal care areas.
Esters derived from benzyl alcohol, and phenoxyethanol have been used in large volumes in the perfume industry, more specifically, acid derivatives of twelve carbon atoms (C
12
) or less; inasmuch as, such molecules exhibit sufficient vapor pressure to exert sufficient volatility to “evaporate” and exert the effect of a perfume. Listed below is a compendium of various benzyl, phenoxyethyl and anisyl alcohol derivatives that have been and currently are being used as “fragrance intermediates” finding use in a variety of fragrance products and masking agents in numerous industries:
Benzyl Acetate
Powerful, but thin, sweet, fresh floral
note. Also used in flavors.
Benzyl Benzoate
Faint, sweet balsamic odor used widely in
fixatives.
Benzyl Caproate
Sweet, fruit slightly green odor. Used in
immitation pineapple and apricot flavors.
Benzyl Laurate
Very faint, fatty odor. Used primarily as
a fixative in perfumes.
Benzyl Myristate
Diluent for fatty aldehyde in fragrances.
Benzyl Pelargonate
Faint, fresh balsamic odor. Used as a
fixative.
Benzyl Propionate
Fruity, sweet odor. Used in flavor.
Benzyl Valerate
Powerful, fruity and somewhat musky. Used
in fragrances.
Phenoxyethyl
Sweet floral odor of good tenacity.
Acetate
Phenoxyethyl-
Sweet-fruity, rosy-floral, slightly honey-
iso-Butyrate
like odor of excellent tenacity.
Phenoxyethyl
Warm, rosy-fruity, slightly earthy.
Propionate
Herbaceous odor of good tenacity.
Phenoxyethyl-
Jordan Jebidiah
Kenney Madeline
Payumo Rustico
Zofchak Albert
Alto, Inc.
Carr Deborah D.
Coleman H.
Sapone W. J.
Sudol R. N.
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