Silicone compound, and a makeup containing this compound

Details Silicone compound, and a makeup containing this compound Silicone compound, and a makeup containing this compound

2002-05-02

2004-07-06

Barts, Samuel (Department: 1621)

Drug, bio-affecting and body treating compositions

Topical sun or radiation screening, or tanning preparations

C424S063000, C424S065000, C424S070100, C424S070120, C424S401000

Reexamination Certificate

active

06759031

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to a makeup containing a specific modified silicone obtained by an economical manufacturing method not requiring an esterification catalyst, having a high reaction rate and therefore leaving little unreacted material, and in particular to a makeup with good skin adhesion, good retention and excellent emulsion 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 blended oils.
Friction and water, etc., are external factors which impair makeup retention. To improve the 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 which increase water repellent properties.
Since they have the characteristic features of light feel, outstanding water-repellent properties and high safety, silicone oils such as dimethylpolysiloxane for example are being used profusely in makeup oils in recent years.
Although dimethylpolysiloxanes have excellent properties as oils for use in cosmetics, it cannot be said that significant improvements had been made regarding enhanced water repellency and adhesion to the skin when they were used in makeup.
In skin care products also, oils were desired with a light feel, water repellent properties and ease of use which would impart a feeling of adhesion to the skin.
In the prior art, resins such as rosin or rosin esters purified from well-known resins for example are occasionally used to improve the adhesion in cosmetics, but they have poor solubility in silicone oils and it was difficult to blend them with makeup using silicone as a foundation material.
For example, in U.S. Pat. Nos. 2,610,496 (Koho), 2,665,799 (Koho) and 2,750,748 (Koho), a makeup is disclosed using the silicone derivative of a hydrate of abietic acid which is contained in rosin to the extent of about 60%. The tetrahydroabietic acid-modified silicone in these patents is synthesized by:
1) a reaction between an alcohol-denatured silicone and tetrahydroabietic acid or tetrahydroabietic acid chloride, or
2) an addition reaction between an ester of tetrahydroabietic acid, an allylpolyoxyethylene alcohol and hydrogen polysiloxane, but the step for synthesizing tetrahydroabietic acid chloride, and the reactions between tetrahydroabietic acid and alcohol-denatured silicone or allylpolyoxyethylene alcohol are all reactions performed under acid conditions, and when resin acids are used containing a large amount of an unsaturated tricyclic diterpene carboxylic acid such as abietic acid, polymerization may occur giving an extreme coloration, and resulting in an alcohol insoluble substance. Therefore, when using this type of reaction, it was necessary to first perform a hydrogen addition reaction to give a saturated resin acid as described in the above patents. Further, when an acid catalyst was used, subsequent steps such as rinsing with water were necessary after the reaction, so the method of synthesis could not be described as economical. Therefore, a method was desired which could simply and cheaply synthesize abietic acid-modified silicones by direct reaction of rosin, which is an unsaturated tricyclic diterpene carboxylic acid, by a reaction not using an acid catalyst.
Problems which this Invention Attempts to Solve
It is therefore an object of this invention to provide a method of synthesizing a silicone compound more cheaply and economically than in the prior art by the heat addition reaction of an unsaturated or unsaturated carboxylic acid having 2-30 carbon atoms, and an alicyclic epoxy compound. The modified silicone obtained by this method does not give rise to alcohol insoluble substances, produces little coloration, and does not use an acid catalyst. Further, makeup which uses this modified silicone are extremely water repellent and have excellent adhesion, while at the same time, it is soluble in volatile oils such as octamethylcylotetrasiloxane and decamethylcyclopentasiloxane, and is therefore easy to use as a cosmetic oil. Moreover, such makeup has a lighter feel than makeup using prior art resins. When this silicone compound is used as an oil in emulsion systems, it has excellent miscibility with oils used in ordinary cosmetics such as silicone oils, ester oils and triglycerides.
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
SiO
(4-a-b)/2
(in the formula, R
1
is at least one substituent group having 1-30 carbon atoms chosen from alkyl, aryl, aralkyl, fluorine-substituted alkyl or organopolysiloxanylsilyl, R
2
is a carboxylate residue represented by the following general formula (2),
R
3
is a saturated or unsaturated hydrocarbon group having 2-30 carbon atoms, a is 1.0-2.5, and b is 0.001-1.5.
Another object of this invention is the above-mentioned silicone compound wherein R
3
is a tricyclic diterpene carboxylic acid. Yet 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 (3)
(in the formula, R
4
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, c is 1-5, and d is 0-500).
Another object of this invention is a makeup containing 0.1-99.5 weight % of the aforesaid silicone compound and 0.5-99.9 weight % of oil, and skin care products, hairdressing products, antiperspirant, makeup products, and ultraviolet defense products which partly contain this makeup material. It may also be in the form of a liquid, emulsion, cream, solid, paste, gel, powder, laminate, mousse or spray.
Yet another object of this invention is a method to synthesize any of the aforesaid silicone compounds by synthesizing an alicyclic epoxy-modified silicone by an addition reaction of a main chain siloxane such as an organohydrogenpolysiloxane to a vinyl alicyclic epoxide, and reacting these with a saturated or unsaturated carboxylic acid.
Embodiments
The silicone compound a) of this invention may be represented by the general formula (1).
R
1
a
R
2
b
SiO
(4-a-b)/2
In the formula, a is 1.0-2.5 but preferably 1.2-2.3, and b is 0.001-1.5 but preferably 0.05-1.0. R
1
is at least one substituent group having 1-30 carbon atoms, chosen from alky, aryl, aralkyl, fluorine-substituted alkyl or organopolysiloxanylsilyl alkyl.
R
1
may be an alkyl group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl; a cycloalkyl group such as cyclopentyl or cyclohexyl; an aryl group such as phenyl or tolyl; an aralkyl group such as benzyl or phenetyl; an alcohol residue such as olioxy or alioxy; a fluorinated alkyl group such as trifluoropropyl or heptadecafluorodecyl, and organopolysiloxanylsilyl alkyl represented by the following general formula (3).
It is preferable that at least about 80% of R
1
are methyl groups. Moreover, it is preferable that at least part of R
1
is the organopolysiloxanylsilyl alkyl group represented by the above-mentioned general formula (3). In the above formula (3), R
4
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, and c is 1-5. In particular, when synthesizing this substituent from the reaction of a vinyl group and a SiH group, c is 2, and d is 0-500 but preferably 1-100.
When d is larger than 500, problems such as poor reactivity of the main chain may a

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