U.S. patent application number 09/834910 was filed with the patent office on 2002-01-24 for novel insoluble s-triazine derivatives, process for their preparation, compositions containing them and uses thereof.
Invention is credited to Lagrange, Alain, Leduc, Madeleine, Richard, Herve.
Application Number | 20020010179 09/834910 |
Document ID | / |
Family ID | 26233166 |
Filed Date | 2002-01-24 |
United States Patent
Application |
20020010179 |
Kind Code |
A1 |
Richard, Herve ; et
al. |
January 24, 2002 |
Novel insoluble S-triazine derivatives, process for their
preparation, compositions containing them and uses thereof
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 application of these
compounds in particular to protecting the skin and the hair against
ultraviolet radiation.
Inventors: |
Richard, Herve; (Villepinte,
FR) ; Leduc, Madeleine; (Paris, FR) ;
Lagrange, Alain; (Coupvray, FR) |
Correspondence
Address: |
BURNS, DOANE, SWECKER & MATHIS, L.L.P.
P.O. Box 1404
Alexandria
VA
22313-1404
US
|
Family ID: |
26233166 |
Appl. No.: |
09/834910 |
Filed: |
April 16, 2001 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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09834910 |
Apr 16, 2001 |
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09319111 |
Oct 4, 1999 |
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09319111 |
Oct 4, 1999 |
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PCT/FR97/01995 |
Nov 6, 1997 |
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Current U.S.
Class: |
514/245 ;
544/207 |
Current CPC
Class: |
C08K 5/34926 20130101;
A61Q 17/04 20130101; C07D 417/14 20130101; A61K 8/4966 20130101;
C07D 403/14 20130101; C03C 17/28 20130101 |
Class at
Publication: |
514/245 ;
544/207 |
International
Class: |
A61K 031/53; C07D
43/14 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 13, 1996 |
FR |
96/15368 |
Claims
1. Compound of formula (I) below: 8in which the symbols R.sub.1,
which may be identical or different, are radicals of formula (ii)
or (iii) below: 9R.sub.2 is a halogen, N(R.sub.4).sub.2, OR, or a
group R.sub.1, R.sub.3, which may be identical or different, are
linear or branched C.sub.1-C.sub.8 alkyl radicals, C.sub.1-C.sub.3
alkoxy radicals, it being understood that, in the latter case, two
adjacent groups R.sub.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.sub.3 or NH.sub.2, R.sub.4, which may
be identical or different, denote a hydrogen atom or a linear or
branched C.sub.1-C.sub.6 alkyl radical, it being possible for two
groups R.sub.4 together to form a ring of 4 or 5 carbon atoms, n is
0, 1, 2, 3 or 4, R.sub.5 is a hydrogen or a C.sub.1-C.sub.6 alkyl
radical.
2. Compound according to claim 1, characterized in that the
radicals R.sub.1, which may be identical or different, denote the
radicals of formula (II') or (III') below: 10in which the radicals
R.sub.3 have the same meaning as those in formulae (II) and (III)
of claim 1 and n' is 0, 1, 2 or 3.
3. Compound according to claim 1 or 2, characterized in that the
radicals R, and the radical R.sub.2 are identical.
4. Compound according to claim 3, characterized in that the said
radicals R.sub.1 and R.sub.2 denote a radical of formula (II').
5. Compound according to claim 4, characterized in that it is
chosen from the following compounds:
2,4,6-tris[(3'-benzotriazol-2-yl-2'-hydroxy-5'-m-
ethyl)phenylamino]-s-triazine and
2,4,6-tris[(3'-benzotriazol-2-yl-2'-hydr-
oxy-5'-tert-octyl)phenylamino]-s-triazine.
6. Process for preparing a compound of formula (I) as defined in
any one of claims 1 to 5, characterized in that it consists in
reacting a compound of formula (IV) below with the derivatives of
formulae R.sub.1H and R.sub.2H according to the reaction scheme
below: 11in which: R.sub.1 and R.sub.2 correspond to the
definitions of any one of claims 1 to 5, X represents a halogen, in
particular chlorine or bromine, m is 0 or 1.
7. Composition intended for protecting a material which is
sensitive to ultraviolet radiation, in particular to solar
radiation, characterized in that it comprises an effective amount
of at least one compound defined in any one of claims 1 to 5.
8. Composition according to claim 7, characterized in that the said
compound is in the form of particles.
9. Composition according to claim 8, characterized in that it is a
cosmetic composition intended for protecting the skin and/or the
hair.
10. Composition according to claim 8 or 9, characterized in
that-the average size of the said particles is less than 20
.mu.m.
11. Composition according to any one of claims 7 to 10,
characterized in that it contains from 0.1 to 15% by weight,
relative to the total weight of the composition, of the said
compound.
12. Composition according to claim 7 or 8, characterized in that it
is a varnish intended for protecting an organic and/or mineral
glass or a plastic.
13. Use of at least one compound defined in any one of claims 1 to
5, in, or for the manufacture of, compositions intended for
protecting materials which are sensitive to ultraviolet radiation,
in particular to solar radiation.
14. Use according to claim 13, characterized in that the said
compositions are cosmetic compositions for protecting the skin
and/or the hair against ultraviolet radiation, in particular
against solar radiation.
15. Use according to claim 13, characterized in that the said
compositions are varnishes for protecting organic and/or mineral
glasses or plastics against ultraviolet radiation, in particular
against solar radiation.
16. Process for protecting a material which is sensitive to
ultraviolet and/or solar radiation, characterized in that it
consists in applying to, or incorporating into, the said sensitive
material an effective amount of a compound as defined in any one of
claims 1 to 5 or of a composition defined in any one of claims 7 to
12.
17. Process according to claim 16, characterized in that it
consists in applying an effective amount of a composition defined
in any one of claims 9 to 11 to the skin and/or the hair.
18. Process according to claim 16, characterized in that it
consists in incorporating an effective amount of the said compound
or of the said composition into a plastic.
19. Process according to claim 16, characterized in that it
consists in applying an effective amount of the said compound or of
the said composition to the surface of a mineral or organic
glass.
20. Composition of material protected according to the process of
claim 18 or 19.
Description
[0001] 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.
[0002] 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).
[0003] 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.
[0004] 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 V-A
radiation.
[0005] 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.
[0006] 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.
[0007] 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.
[0008] This discovery forms the basis of the invention.
[0009] Thus, according to the present invention, novel compounds
are now proposed corresponding to formula (I) below: 1
[0010] in which the symbols R.sub.1, which may be identical or is
different, are radicals of formula (II) or (III) below: 2 3
[0011] R.sub.2 is a halogen, N(R.sub.4).sub.2, OR.sub.5 or a group
R.sub.1,
[0012] R.sub.3, which may be identical or different, are linear or
branched C.sub.1-C.sub.8 alkyl radicals, C.sub.1-C.sub.3 alkoxy
radicals, it being understood that, in the latter case, two
adjacent groups R.sub.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.sub.3 or NH.sub.2,
[0013] R.sub.4, which may be identical or different, denote a
hydrogen atom or a linear or branched C.sub.1-C.sub.6 alkyl
radical, it being possible for two groups R.sub.4 together to form
a ring of 4 or 5 carbon atoms,
[0014] n is 0, 1, 2, 3 or 4,
[0015] R.sub.5 is a hydrogen or a C.sub.1-C.sub.6 alkyl
radical.
[0016] In a preferred embodiment of the invention, the radicals
R.sub.1, which may be identical or different, denote the radicals
of formula (II') or (III') below: 4
[0017] in which the radicals R.sub.3 have the same meaning as those
of formulae (II) and (III) and n' is 0, 1, 2 or 3.
[0018] In one preferred embodiment of the invention, the two
radicals R.sub.1 and the radical R.sub.2 are identical. Also
preferably, the two radicals R.sub.1 and the radical R.sub.2 are
identical and denote a radical of formula (II').
[0019] 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.
[0020] 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.
[0021] 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.
[0022] 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.
[0023] 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.sub.1H and R.sub.2H according to the
reaction scheme below: 5
[0024] in which:
[0025] R.sub.1 and R.sub.2 correspond to the definitions given for
formula (I) above,
[0026] X represents a halogen, in particular chlorine or
bromine,
[0027] m is 0 or 1.
[0028] The compounds R.sub.1H 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).
[0029] Thus, as aminobenzotriazole derivatives, mention may be made
of:
[0030] 2-(2-hydroxy-5-aminophenyl)-5-methoxybenzotriazole described
in document EP 221,630,
[0031] 2-(2-hydroxy-4-aminophenyl)benzotriazole,
2-(2-hydroxyphenyl)-5-ami- nobenzotriazole and
2-(2-hydroxy-5-methylphenyl)-5-aminobenzotriazole described in
documents U.S. Pat. No. 3,159,646 and GB 1,346,764,
[0032] 2-(2-hydroxy-5-aminophenyl)benzotriazole described in the
document J. Belusa et al., Chem. Zvesti,
[0033] 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)),
[0034] 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.
[0035] 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.
[0036] The above reactions can optionally be carried out in the
presence of a solvent (toluene, xylene or acetone/water).
[0037] Among the compounds in accordance with the invention,
mention may be made more particularly of:
[0038]
2,4,6-tris[(3'-benzotriazol-2-yl-2'-hydroxy-5'-methyl)phenylamino]--
s-triazine,
[0039]
2,4,6-tris[(3'-benzotriazol-2-yl-2'-hydroxy-5'-tert-octyl)phenylami-
no]-s-triazine.
[0040] 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 particular, dry-grinding or grinding in a
solvent medium, screening, atomization, micronization or spraying.
They can then be used as pigments for the antisun protection of
human skin and the hair. They can also be used as agents for
protecting against light in the plastics industry, in the glass
industry (packaging, optical glasses, in particular for spectacles)
and the like.
[0041] A subject of the present invention is also a composition
intended for protecting a material which is sensitive to
ultraviolet radiation, in particular to solar radiation, comprising
an effective amount of at least one compound of formula (I).
[0042] More particularly, when the sensitive material to be
protected is the skin and/or the hair, this composition is in the
form of a cosmetic composition comprising, in a cosmetically
acceptable support, an effective amount of at least one compound of
formula (I).
[0043] Preferably, the compounds according to the invention are
used, in the cosmetic compositions in accordance with the
invention, in particulate form, the average size of the particles
being less than 20 .mu.m.
[0044] The compound(s) of formula (I) can be present in the
cosmetic composition according to the invention in proportions of
between 0.1 and 20% by weight, relative to the total weight of the
composition, preferably between 0.1 and 15%.
[0045] The cosmetic composition of the invention can be used as a
composition for protecting the human epidermis or the hair or as an
antisun composition.
[0046] Needless to say, the compositions according to the invention
can contain one or more additional hydrophilic or lipophilic
sunscreens which are active in the UVA and/or UVB range
(absorbers), other than those of the present invention. These
additional screening agents can be chosen in particular from
cinnamic derivatives, salicylic derivatives, camphor derivatives,
triazine derivatives other than the compounds in accordance with
the present invention, benzophenone derivatives, dibenzoylmethane
derivatives, .beta., .beta.-diphenylacrylate derivatives,
p-aminobenzoic acid derivatives, and the screening polymers and
screening silicones described in patent application WO-93/04665.
Other examples of organic screening agents are given in patent
application EP-A-0,487,404.
[0047] The compositions according to the invention can also contain
agents for artificially tanning and/or browning the skin
(self-tanning agents), such as, for example, dihydroxyacetone
(DHA).
[0048] The compositions according to the invention can also contain
pigments or alternatively nanopigments (average size of the primary
particles: generally between 5 nm and 100 nm, preferably between 10
nm and 50 nm), of coated or uncoated metal oxides, such as, for
example, nanopigments of titanium oxide (amorphous or crystallized
in rutile and/or anatase form), of iron oxide, of zinc oxide, of
zirconium oxide or of cerium oxide, which are all UV
photoprotective agents that are well known per se. Conventional
coating agents are, moreover, alumina and/or aluminium stearate.
Such coated or uncoated metal oxide nanopigments are described in
particular in patent applications EP-A-0,518,772 and
EP-A-0,518,773.
[0049] The compositions according to the invention can also
comprise conventional cosmetic adjuvants chosen in particular from
fatty substances, organic solvents, ionic or nonionic thickeners,
softeners, antioxidants, opacifiers, stabilizers, emollients,
silicones, .alpha.-hydroxy acids, antifoaming agents, moisturizers,
vitamins, fragrances, preserving agents, surfactants, fillers,
sequestering agents, polymers, propellants, basifying or acidifying
agents, dyes or any other ingredient usually used in cosmetics, in
particular for manufacturing antisun compositions in emulsion
form.
[0050] The fatty substances can consist of an oil or a wax or
mixtures thereof, and they also comprise fatty acids, fatty
alcohols and fatty acid esters. The oils can be chosen from animal,
plant, mineral or synthetic oils and in particular from liquid
petroleum jelly, liquid paraffin, volatile or non-volatile silicone
oils, isoparaffins, poly-.alpha.-olefins, fluoro oils and perfluoro
oils. Similarly, the waxes can be chosen from animal, fossil,
plant, mineral or synthetic waxes which are known per se.
[0051] Among the organic solvents, mention may be made of lower
alcohols and polyols.
[0052] The thickeners can be chosen in particular from crosslinked
polyacrylic acids and modified or unmodified guar and cellulose
gums such as hydroxypropyl guar gum, methylhydroxyethylcellulose,
hydroxypropylmethylcellulose or hydroxyethylcellulose.
[0053] Needless to say, a person skilled in the art will take care
to select the optional additional compound(s) mentioned above
and/or the amounts thereof such that the advantageous properties
intrinsically associated with the compound in accordance with the
invention are not, or are not substantially, adversely affected by
the addition(s) envisaged.
[0054] When the composition according to the invention is used for
protecting the human epidermis against UV rays, or as an antisun
composition, it can be in the form of a suspension or a dispersion
in solvents or fatty substances, in the form of a nonionic vesicle
dispersion or alternatively in the form of an emulsion, preferably
of oil-in-water type, such as a cream or a milk, in the form of an
ointment, a gel, a cream-gel, a solid tube, a stick, an aerosol
mousse or a spray.
[0055] When the composition according to the invention is used for
protecting the hair, it can be in the form of a shampoo, a lotion,
a gel, an emulsion, a nonionic vesicle dispersion or a lacquer for
the hair and can constitute, for example, a rinse-out composition,
to be applied before or after shampooing, before or after dyeing or
bleaching, before, during or after permanent-waving or
straightening the hair, a styling or treating lotion or gel, a
blow-drying or hairsetting lotion or gel, or a composition for
permanent-waving, straightening, dyeing or bleaching the hair.
[0056] The compositions of the invention can be prepared according
to the techniques which are well known to those skilled in the art,
in particular those intended for the preparation of emulsions of
oil-in-water or water-in-oil type.
[0057] When the sensitive material to be protected is an organic
and/or mineral glass or a plastic, the compositions according to
the invention can be in the form of a varnish which is applied to
the said sensitive material in order to protect it against
ultraviolet radiation.
[0058] A subject of the present invention is also the use of at
least one compound of formula (I) in, or for the manufacture of,
compositions intended for protecting materials which are sensitive
to ultraviolet radiation, in particular to solar radiation.
[0059] In particular, a subject of the invention is the use of at
least one compound of formula (I) in, or for the manufacture of,
cosmetic compositions for protecting the skin and/or the hair
against ultraviolet radiation, in particular solar radiation.
[0060] A subject of the present invention is also the use of at
least one compound of formula (I) in, or for the manufacture of,
varnishes intended to protect organic and/or mineral glasses or
plastics against ultraviolet radiation, in particular solar
radiation.
[0061] The compounds of the invention can also be incorporated
directly into plastics, or into other materials which are sensitive
to ultraviolet radiation, in order to protect these materials
against the said radiation.
[0062] A subject of the present invention is thus also a process
for protecting a material which is sensitive to ultraviolet and/or
solar radiation against the said radiation, this process consisting
in applying to, or incorporating into, the said sensitive material
an effective amount of a compound of formula (I) or of a
composition containing at least one compound of formula (I).
[0063] In particular, the process according to the invention can
consist in applying an effective amount of a cosmetic composition
as defined above to the skin and/or the hair.
[0064] In another embodiment of the invention, the process
according to the invention consists in incorporating into a plastic
an effective amount of a compound of formula (I) or of a
composition containing at least one compound of formula (I) in
order to protect the said plastic against ultraviolet radiation, in
particular against solar radiation.
[0065] Thus, one subject of the invention is a plastic composition
protected by such a process.
[0066] In another embodiment of the invention, the process
according to the invention consists in applying an effective amount
of the said compound or of the said composition to the surface of a
mineral or organic glass.
[0067] Thus, lastly, a final subject of the invention is a
glassware composition protected by this process.
[0068] Concrete, but in no way limiting, examples illustrating the
invention will now be given.
EXAMPLE 1
[0069] Preparation of
2.4,6-tris[(3'-benzotriazol-2-yl-2'-hydroxy-5'-methy-
l)phenylamino]-s-triazine: 6
[0070] A mixture of
2-(2-hydroxy-3-amino-5-methylphenyl)benzotriazole (1.2 g,
5.times.10.sup.-3 mol) and cyanuric chloride (0.276 g,
1.5.times.10.sup.-1 mol) in 50 ml of xylene is refluxed for 12
hours under nitrogen. A precipitate forms, which is filtered off,
rinsed with xylene and-dried under vacuum. The derivative is thus
obtained (1 g, yield 83%), with the following characteristics:
[0071] pale yellow powder
[0072] m.p.>270.degree. C.
1 Elemental analysis for C.sub.42H.sub.33N.sub.15O.sub.3: theory:
C: 63.39 H: 4.18 N: 26.40 found: C: 64.09 H: 4.25 N: 26.12
[0073] This
2,4,6-tris[(3'-benzotriazol-2-yl-2'-hydroxy-5'-methyl)phenylam-
ino]-s-triazine was screened at 50 .mu.m through a screen of
stainless steel-gauze stainless steel assembly. Next, it was
dispersed in white petroleum jelly sold under the trade name "Codex
236" by the company Sarega at the melting point of the petroleum
jelly and in a proportion of 5 g of screened
2,4,6-tris[(3'-benzotriazol-2-yl-2'-hydroxy-5'-methyl)
phenylamino]-s-triazine per 100 g of petroleum jelly. This mixture
was then treated with ultrasound in order to ensure homogeneous
dispersion. A film 10 .mu.m thick was analysed.
[0074] The solid UV absorption spectrum was obtained using a
Shimadzu UV 2101 PC spectrophotometer and is represented in FIG. 1
+L.
[0075] It is clearly seen in this figure that the
2,4,6-tris[(3'-benzotria-
zol-2-yl-2'-hydroxy-5'-methyl)-phenylamino]-s-triazine absorbs
throughout the UV radiation range (280-400 nm).
EXAMPLE 2
[0076] Preparation of
2,4,6-tris[(3'-benzotriazol-2-yl-2'-hydroxy-5'-tert--
octyl)phenylamino]-s-triazine: 7
[0077] 2-(2-hydroxy-3-amino-5-tert-octylphenyl)benzotriazole (3.38
g, 0.01 mol) in 50 ml of xylene is introduced into a fully equipped
round-bottomed flask. Cyanuric chloride (0.553 g, 3.times.10.sup.-3
mol) is introduced portionwise over 30 minutes at room temperature,
under a stream of nitrogen, and the mixture is heated to 60.degree.
C. The mixture is left at this temperature for 1 hour and is then
refluxed for 3 hours 30 minutes. The clear mixture is cooled to
about 60.degree. C.; 60 ml of ethanol are added thereto and the
precipitate obtained is filtered off and washed with ethanol and
then with water. The derivative (3.3 g, 100% yield) is thus
obtained, with the following characteristics:
[0078] pale yellow powder
[0079] m.p.>270.degree. C.
[0080] UV (CHCl.sub.3).lambda..sub.max=326 nm,
.epsilon..sub.max=68,600
[0081] UV: (in solid form): see FIG. 2 (absorption spectrum)
2 Elemental analysis for C.sub.63H.sub.75N.sub.15O.sub.3: theory:
C: 69.40 H: 6.93 N: 19.27 found: C: 69.39 H: 6.96 N: 18.95
[0082] The solid UV absorption spectrum of this
2,4,6-tris[(3,-benzotriazo-
l-2-yl-2'-hydroxy-5'-tert-octyl)phenylamino]-s-triazine was
measured according to the same procedure as in Example 1. This
spectrum is represented in FIG. 2 +L. It is also clearly seen in
this FIG. 2 that the
2,4,6-tris[(31-benzotriazol-2-yl-2'-hydroxy-5'-tert-octyl)phenylamino]-s--
triazine absorbs throughout the UV radiation range (280-400
nm).
EXAMPLE 3
[0083] A concrete example of a cosmetic composition in the form of
an oil-in-water emulsion is given below (the amounts are expressed
as a % by weight relative to the total weight of the
composition):
3 mixture of cetylstearyl alcohol and of 7% cetylstearyl alcohol
oxyethylenated with 33 mol of ethylene oxide, sold under the trade
name "Sinnovax AO" by Henkel non-self-emulsifying mixture of 2%
glyceryl mono- and distearate cetyl alcohol 1.5% silicone oil 1.5%
diisopropyl adipate 15% derivative of Example 1 5% glycerol 20%
fragrance, preserving agents qs water qsp 100%
[0084] This composition was prepared in the following way: after
preparing the emulsion, the screening agent was dispersed at about
40.degree. C. The cream obtained was then homogenized with a
triple-roller machine.
[0085] This composition absorbs throughout the UV radiation
range.
* * * * *