DE1492403A1 - UV light protection agents for cosmetic purposes - Google Patents

Description

Ii. K β rc: < 2b Kärz "« 965

Aktiengeselschaf t

Darmstadt 1492403

UV light protectants for cosmetic purposes

There-! Invention relates to a group of chemical compounds ,, the 'Λβ may UV absorbers be used,

It was found that compounds of the formula 1

wherein

_R 2 R ¹ H or SO ₃ H and

^R { ^{2 5}

^{up to r5} hydrogen or alkyl with _K 4 __ / \ _ _co -J. S ^^ Jt ' * ^{up to 12 Ö} - ^At o = »en, preferential

^R v {

y wise methyl,

mean »where the heete R"' ^j and R ⁵ or the radicals R ⁵ and R ⁴

with formation of an alkylene chain can be linked with 3 or 4 carbon atoms,

and / or their salts, preferably their sodium, potassium, mono-, bi- or triethanolammoniuEsalae, have excellent UV absorption (low permeability) in the UV range of about 290-320 wp ^ overdosing of UV rays in this The area is responsible for the burn symptoms of human chewing, known as "sunburn"

The following table shows, for example, the permeability of a 2-strength solution of 2- (2,4-dimethylbenzoyl) -ben ofuran in Methanul at a visual thickness of 0.005 ma depending on indicated by the wavelength:

8 Q 9 8 4 9/1 3 7 O

New © documents W>'- V ab ». 2 νγ. t sentence 3 de> change *** · »· *« · ^α "

U92403

Wavelength in on # Permeability 260 63 270 49 280 34 290 23 295 19th 500 16 305 13th 310 12th 3 ^ 5 14th 320 18th 330 47 340 74 360 96

As you can see, the minimum permeability is 310 inu in the skin-damaging area, while the tanning rays in the area above 330 χψ are not absorbed and can take full effect. The other compounds of the formula I show similar permeability values.

The invention accordingly relates to absorbing UV rays Agents for cosmetic purposes, characterized by a content of compounds of the formula I and / or their salsa in addition to the usual ones Additives and / or carriers.

The advantages of the new means over the already known ones In addition to their selective absorption, light protection agents lie in particular in their good chemical stability and their low toxicity, high light and weather resistance as well Odorlessness.

Compared to those currently on the market as street fliters Links; of which as top products p ~ methoxy ~ 8imt8 acid ethoxyethyl ester and p-dimethylamino-lienoate acid methyl ester " bsw. -glycerol esters are called, the m

909849/1370

BATH

the new substances contained agents particularly by aue _P that they contain no Estergruppen and oomit even under difficult conditions no decomposition ιVerseifung) subject to this stability of the new means guarantees a constant? effectiveness

The basic substances in which B - H is based on the agents according to the invention are soluble in mineral or vegetable oils and fats, e.g. in liquid paraffin or saturated fatty acid triglycerides. They are particularly soluble in paraffin and vegetable oils 2- (2 _: 4-D3alkyl * -benzoylj-benzofurane * especially dao2 ~ i2,4-Pimethylbenzoyl3-benzofurane _f, which is therefore particularly well suited for use as a radiation filter in coanetic! Preparations a sO fonsäuregruppe contain, as well as their salts, preferably IBt sodium, potassium, Monoäthanolammonium-i Diäthanolaffimunium- and Trläthanolammoniumsalze are, readily water-soluble _s so that it is possible to use compounds of formula I or mixtures thereof for any and all cosmetic preparations .

So you can by adding suitable ointment or cream bases greasy or non-greasy light protection albums or by mixing with suitable solvents, if necessary with the addition of Emulsifiers, liquid light skin preparations ,: Such Solutions or emulsions can also be used as aerosols along with a propellant are used,

Compounds of the following are particularly advantageous proven general formula:

wherein

R ⁶ H or SO ₅ H,

K ⁷ and R ^{8 are} H or CH ₅ ,

as well as their salts, if necessary, their sodium, potassium, koao = - ₉ bi- or friäthaaaolaiaffloiiiumsalzet

9098.9 / 1370 ^

U92403

In detail, all compounds suitable for Bonders Cut are the called the following:

2-benzoyl-benzofuran; 2- (2,4'-dimethylbenzoyl) -tenzofuran, bp-195 1/2 mm. 2- (4-methylbeiizoyl) benzofuran; 2 ~ (4-isopr:> pylbenzoyl) -benzofuranj F, 105-107 ⁰ J 2- (tetrahydronaphthoyl-2) - 'oonzofuran, P. 58-60 °; 2- (4-tert-butylbenzoyl) -benzofurans F, 122-124 °; 2- (3,4-dimethylbenzoyl-benzofuran, P. 101-103 °; 2- (2,3,5-trimethylbenaoyl) -benzofuran, b.p. 260-265 ° / 12 mm j 2- (2-Iaopropyl-5 -methyll3enzoyl) -benaofuran, b.p. 280-290 ° / 2O mm, as well as the sulfonic acids derived therefrom, especially 2-benzoyl-benzofuran-x-sulfonic acid (the sulfonic acid group is probably in the 5-3 division of the berizofuran system) and their salts ( Natriumaalz, P.> 300 °).

The compounds are mostly »new. The compounds with R * -B bind accessible in a manner known per se by reacting benzofurancarboxylic acid-2-chloride and benzene or * alkylbenzenes, such as toluene, o-, m- or p-xylene, Cumene, p-cymene, tert-butylbenzene, indane or tetralin, in the presence of aluminum chloride. £ j) "Ghlor'2,4 ~ dimethylacetophenone, 6> ^{i-bromo-2,4-dimethy} acetophenone!

The corresponding sulfonic acids (H = SO ₅ H) can be obtained by sulfonating the benzoylbenzofurans with sulfuric acid at room temperature; ale can be prepared conventionally .lurch reaction with a base such as sodium or potassium hydroxide, sodium or potassium mono-, di- or triethanolamine _'t be converted into the desired salts "

The smock according to the invention can also contain one or more other UV absorbers such as. Bo 2 ~ phenylbenzimidazole «5-sulfonic acid sodium salt * 3 _t 4 - dimethylphenylglyoxylic acid hatriue ~ aals, 4-rienylbenzophenone, 4 ~ phenylbenzophenone-2'-carboxy aooctyl ester,

D ^J 'e Zalxlen in the following leispielf π are Gewichteteili.

809849/1370 " ⁵ ^

BATH

U9240-3

Example 1: light protection oil

2- (2,4-dimethyl likewiseyl) benzofuran Paraffin, liquid, DAB 6 isopropyl myristate

Additives (preservatives, perfume, nut extract, coloring, etc.)

2 50 48 as required

Example 2: light protection cream

2- (2,4-dimethylbenzoyl) benzofuran Additives ad 3 Cream base 3-layer (system oil in water Example 3: Aqueous solution 97 or water in oil) 2 ~ Benzoylbenzofuran-x-sulfonic acid- Sodium salt upon need Sorbitol Glycerin 3 Ethanol water 3 Additives 3 20, ' 100 according to Badarf

Example 4: Aerosol

Mixture according to Example 1 mixture of trichlorofluoromethane and Dichlorodifluoromethaii (70:30) (propellant gas)

Example 5: sun protection cream

2- (2,4-dimethylbenzoyl) benzofuran 2- (Phenyl-benzimidazole-5-sulfonic acid ~

Triethanolamine salt 50% cream base (system oil / water or

'Water / oil) additives

9098 49 / 137.0

80 20

2 3

95

upon need

Claims (1)

ratantonngrüche 1ο UV rays absorbiureude means for cosmetic purposes, characterized by a content of one or more compounds of the formula I. wherein. R to R hydrogen or alkyl R ¹ KL or SCUB and // —Vv (Ι ί J— ^{r1 with} * * ^{is 12} C-atoms R ν) 00 ^ Kq - ^ "^^ preferably methyl, rS / mean, where also the remainders - ¹ R and R "^ or the radicals R ⁷ and R ^ to form an alkylene chain of 3 or 4 C-atoms connected with each other * could be, and / or optionally their salts, preferably their Ifatrium », potassium, mono-, di- or triethanol monium salts, in addition to the usual additives and / or carriers. Agent according to Claim 1, characterized by a content of 2-benzoyl-benzofuran, salts of 2-benzoyl-benzofuran-x-sulfonic acid and / or 2- (2,4-dimethylbenzoyl) benzofuran _e 3e means according to claim 1 or 2, characterized by one additional content of one or more other UV absorbers BAD ORJGiNAL 909849 / 137Q Neue UnteratjOH ι * «·. δ ' ^Α ^ - * ^ur