Insoluble s-triazine derivatives and their use as UV filters

Details Insoluble s-triazine derivatives and their use as UV filters Insoluble s-triazine derivatives and their use as UV filters

2001-04-16

2002-03-26

Dodson, Shelley A. (Department: 1624)

Drug, bio-affecting and body treating compositions

Topical sun or radiation screening, or tanning preparations

C424S060000, C424S400000, C424S401000, C514S241000

Reexamination Certificate

active

06361764

ABSTRACT:

The present invention relates to novel insoluble s-triazine derivatives bearing benzotriazole and/or benzothiazole groups, to a process for their preparation and to their uses in particulate form as UV screening agents, in particular in the cosmetic field.
The present invention also relates to the use of these novel compounds for protecting the skin and/or the hair against ultraviolet radiation, or for protecting any other material which is sensitive to UV (mineral or organic glasses, plastics or the like).
It is known that light radiation with wavelengths of between 280 nm and 400 nm permit tanning of the human epidermis and that rays with wavelengths of between 280 nm and 320 nm, known as UV-B, cause skin burns and erythema which can be harmful to the development of a natural tan. For these reasons, as well as for aesthetic reasons, there is a constant demand for means for controlling this natural tanning in order thus to control the colour of the skin; this UV-B radiation should thus be screened out.
It is also known that UV-A rays, with wavelengths of between 320 nm and 400 nm, which cause tanning of the skin, are capable of inducing degradation thereof, in particular in the case of sensitive skin or of skin continually exposed to solar radiation. In particular, UV-A rays cause a loss of skin elasticity and the appearance of wrinkles, leading to premature ageing. They promote the triggering of the erythemal reaction or amplify this reaction in certain individuals and can even be the cause of phototoxic or photoallergic reactions. Thus, for aesthetic and cosmetic reasons such as the conservation of the skin's natural elasticity, for example, more and more people wish to control the effect of UV-A rays on their skin. It is thus desirable also to screen out UV-A radiation.
A large number of compounds have already been proposed as sunscreens, essentially in the form of soluble organic screening agents or of insoluble inorganic compounds. These screening agents must be able to absorb or block out the harmful rays of the sun while remaining harmless for the user.
In this respect, and in order to limit any risks of allergy on the skin caused by the organic screening agents on account of their solubility, inorganic pigments such as zinc oxide or titanium oxide are increasingly used to screen out UV rays. However, these inorganic pigments have the drawback of being sensitive to solar radiation (phenomenon known as photo-bluing). Moreover, for equivalent amounts, these inorganic pigments are less effective in protecting against UV than the abovementioned organic screening agents.
After considerable-research conducted in the field of photoprotection mentioned above, the Applicant has now discovered novel non-mineral insoluble UV screening agents which are capable of absorbing both in the UV-A range and in the UV-B-range, and which have the advantage of cumulating both the property of diffusion, since they are solid organic pigments, and the property of absorption.
This discovery forms the basis of the invention.
Thus, according to the present invention, novel compounds are now proposed corresponding to formula (I) below:
in which the symbols R
1
, which may be identical or different, are radicals of formula (II) or (III) below:
R
2
is a halogen, N(R
4
)
2
, OR
5
or a group R
1
,
R
3
, which may be identical or different, are linear or branched C
1
-C
8
alkyl radicals, C
1
-C
3
alkoxy radicals, it being understood that, in the latter case, two adjacent groups R
3
on the same aromatic ring can together form an alkylidenedioxy group in which the alkylidene group contains 1 or 2 carbon atoms, OH, NHCOCH
3
or NH
2
,
R
4
, which may be identical or different, denote a hydrogen atom or a linear or branched C
1
-C
6
alkyl. radical, it being possible for two groups R
4
together to form a ring of 4 or 5 carbon atoms,
n is 0, 1, 2, 3 or 4,
R
5
is a hydrogen or a C
1
-C
6
alkyl radical.
In a preferred embodiment of the invention, the radicals R
1
, which may be identical or different, denote the radicals of formula (II′) or (III′) below:
in which the radicals R
3
have the same meaning as those of formulae (II) and (III) and n′ is 0, 1, 2 or 3.
In one preferred embodiment of the invention, the two radicals R
1
and the radical R
2
are identical. Also preferably, the two radicals R
1
and the radical R
2
are identical and denote a radical of formula (II′).
These novel insoluble s-triazine compounds can be used as sunscreens for human skin and the hair, and also as agents for protecting against light in the plastics industry.
The derivatives of the invention are insoluble compounds capable of simultaneously absorbing in the UV-A range and in the UV-B range. The radicals of formulae (II) and (III) are screening units which generally absorb UV-A radiation; the novel insoluble compounds in accordance with the present invention, substituted with these radicals, have the unexpected and surprising advantage of absorbing both in the UV-A range and in the UV-B range.
Moreover, besides their screening and dispersing properties, these novel derivatives have good chemical and photochemical stability. On account of their insolubility, they present little risk of penetration into the epidermis. These compounds are thus all indicated for the preparation of compositions intended for the antisun protection of the skin and the hair.
For the purposes of the present invention, the expression insoluble or substantially insoluble compounds means compounds whose solubility in water is less than 0.1% by weight, whose solubility in liquid petroleum jelly is less than 1% by weight and, lastly, whose solubility in a mixture of triglyceride esters such as “Miglyol 812” sold by the company Dynamit Nobel is less than 2%, also by weight.
A subject of the present invention is also a process for preparing the compounds of formula (I) defined above, which consists in reacting a compound of formula (IV) below with the derivatives of formulae R
1
H and R
2
H according to the reaction scheme below:
in which:
R
1
and R
2
correspond to the definitions given for formula (I) above,
X represents a halogen, in particular chlorine or bromine,
m is 0 or 1.
The compounds R
1
H can be prepared according to known methods as described in patents DE 2,128,005, EP 221,630, FR 1,324,897 or in the article by T. Konstantinova et al., Polymer Degradation and Stability, 43, 187 (1994).
Thus, as aminobenzotriazole derivatives, mention may be made of:
2-(2-hydroxy-5-aminophenyl)-5-methoxybenzotriazole described in document EP 221,630,
2-(2-hydroxy-4-aminophenyl)benzotriazole, 2-(2-hydroxyphenyl)-5-aminobenzotriazole and 2-(2-hydroxy-5-methylphenyl)-5-aminobenzotriazole described in documents U.S. Pat. No. 3,159,646 and GB 1,346,764,
2-(2-hydroxy-5-aminophenyl)benzotriazole described in the document J. Belusa et al., Chem. Zvesti,
2-(2-hydroxy-5-aminophenyl)-5-chlorobenzotriazole and 2-(2-hydroxy-4-aminophenyl)-5-chlorobenzotriazole described in the document H. S. Freeman et al., Dyes and Pigments, 20, 171 (1992)),
2-(2-hydroxy-3-amino-5-methylphenyl)benzotriazole, 2-(2-hydroxy-3-amino-5-tert-butylphenyl)benzotriazole and 2-(2-hydroxy-3-amino-5-tert-octylphenyl)benzotriazole, which can be prepared according to methods described in documents DE 2,128,005 and GB 1,346,764.
As aminobenzothiazole derivative, mention may be made, for example, of 2-(para-aminophenyl)-6-methylbenzothiazole described in document U.S. Pat. No. 2,334,348.
The above reactions can optionally be carried out in the presence of a solvent (toluene, xylene or acetone/water).
Among the compounds in accordance with the invention, mention may be made more particularly of:
2,4,6-tris[(3′-benzotriazol-2-yl-2′-hydroxy-5′-methyl)phenylamino]-s-triazine,
2,4,6-tris[(3′-benzotriazol-2-yl-2′-hydroxy-5′-tert-octyl)phenylamino]-s-triazine.
These novel insoluble or substantially insoluble s-triazine derivatives can be brought into a suitable particulate form by any ad-hoc means such as, in particul

Affiliated with

Also associated with

Rating

Insoluble s-triazine derivatives and their use as UV filters does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Insoluble s-triazine derivatives and their use as UV filters, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Insoluble s-triazine derivatives and their use as UV filters will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2857934