Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2001-02-02
2004-04-06
Barts, Samuel (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C556S446000, C424S401000, C424S065000, C424S063000, C424S060000, C424S070120, C523S209000, C523S213000, C523S216000, C514S772300
Reexamination Certificate
active
06717003
ABSTRACT:
A novel silicone compound, a powder surface-treated with this compound, and a makeup containing this powder.
FIELD OF THE INVENTION
This invention relates to a powder which is surface-treated by a novel silicone compound, and to a makeup containing this powder. In particular, it relates to a silicone compound which has good compatibility with oils such as ester oils and triglycerides or silicone oils, and to a makeup with a smooth feel, excellent dispersibility and excellent emulsification stability.
BACKGROUND OF THE INVENTION
In general, male secretions such as sweat, tears and sebum, lead to messy makeup, and sebum secreted from the skin becomes mixed with the oil in which the makeup is blended. This is a major reason why too much wetting of the powder in the makeup leads to messy makeup. To reduce the oil in makeup remaining on the skin, it has been attempted to use volatile oils, such as octamethylcylotetrasiloxane and decamethylcyclopentasiloxane, as part of the oils blended therein.
Friction and water, etc., are external factors which impair makeup retention. To improve poor makeup retention which occurs due to water-soluble substances, such as sweat and tears, loss of water-soluble components and sebum, etc., in the skin is prevented, and the protective effect of the skin is maintained, by blending with silicone oils to increase water repellent properties.
For example, since they have the characteristic features of light feel, outstanding water-repellent properties and high safety, silicone oils such as dimethylpolysiloxane are being used profusely in makeup oils in recent years.
Pigments such as red ocher and titanium oxide, etc. and powders such as mica and sericite are widely used in makeup or antiperspirant such as lipstick, lip balm, nail varnish, nail coat, foundation, mascara or eyeliner, and in order to impart sufficient water repellent properties and sufficient safety to these materials, it is common to perform a surface treatment by metallic soap, alumina, silica, phosphating, etc.
For example, in U.S. Pat. No. 2,719,303, a method is disclosed of carrying out surface treatment with 12-60 weight parts of methyl hydrogen polysiloxane to 100 weight parts of powder. In Provisional Publication No. 7-196946, a surface treatment method is disclosed using a straight chain single-terminated alkoxy denatured silicone. These powder treatments with silicone are generally known in the art, but enhanced miscibility with ordinary oils, enhanced miscibility with fluorinated oils, enhanced miscibility with silicone oils or improved stability of emulsions in these composite systems, was desired.
Means for Solving the Problems
The main object of this invention is a silicone compound represented by the general formula (1):
R
1
a
R
2
b
R
3
c
SiO
(4-a-b-c)/2
(in the formula, R
1
is at least one organic group having 1-30 carbon atoms chosen from alkyl, aryl, aralkyl, fluorine-substituted alkyl or organopolysiloxanylsilyl, R
2
is a reactive substituent group chosen from hydrogen, hydroxy or alkoxy having 1-6 carbon atoms, or a reactive substituent group in which at least one of carbon, oxygen and silicon are bonded to these reactive substituent groups, R
3
is a carboxylate residue represented by the following general formula (2):
R
4
CO
2
—Q—
R
4
is a saturated or unsaturated hydrocarbon group having 2-30 carbon atoms, Q is a bivalent hydrocarbon group which may also contain a hetero atom, a is 1.0-2.5. b is 0.001-1.5, and c is 0.001-1.5.
Another object of this invention is the above-mentioned silicone compound wherein R
3
is a carboxylate residue represented by the general formula (3):
(in the formula, R
4
is a saturated or unsaturated hydrocarbon group having 2-30 carbon atoms).
Another object of this invention is the above-mentioned silicone compound wherein R
4
is a resin acid residue of a tricyclic diterpene carboxylic acid.
Another object of this invention is the above-mentioned silicone compound wherein at least part of R
1
is represented by the following general formula (4):
in the formula, R
5
may respectively be identical or different, and is at least one substituent group having 1-30 carbon atoms chosen from alkyl, aryl, aralkyl, fluorine-substituted alkyl or hydroxyl, d is 1-5, and e is 0-500).
Another object of this invention is a method of manufacturing the above-mentioned silicone compound comprising the synthesis of an alicyclic epoxy-modified silicone by an addition reaction of a main chain siloxane which is an organohydrogen polysiloxane to a vinyl alicyclic epoxide, and the reaction of a saturated or unsaturated carboxylic acid therewith.
REFERENCES:
patent: 3502769 (1970-03-01), Nobukazu
patent: 4336246 (1982-06-01), Leon-Pekarek
patent: 4801445 (1989-01-01), Fukui et al.
patent: 5505937 (1996-04-01), Castrogiovanni et al.
patent: 5911974 (1999-06-01), Brieva et al.
patent: 2124081 (1984-02-01), None
Nakanishi Tetsuo
Ono Ichiro
Shimizu Toru
Barts Samuel
Millen White Zelano & Branigan P.C.
Shin-Etsu Chemical Co. , Ltd.
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