DE2533048A1 - Spiroketal antiburning cpd. for cosmetic compsns. - and pref. use in sun protective and sunburn preventing preparations - Google Patents

Abstract

Spiroketals are used as anti-burning agents in cosmetic compsns. The spiroketals have formula (I): In (I) R1 to R6 are each H, 1-8C alkyl or 1-4C hydroxy-alkyl; m is 0,1 or 2. Y is an alkylene group having formula: -(CR7R8)n-(CR=CR10)p-CR11R12-(CR13R4)q-CR15R16-CR17R18-(II). R7 to R18 ar H, 1-4C alkyl or halogen. n and p are 0 or 1; q is 0 to 9. R9 and R10, together with double bond, can form an o-phenylene group opt. substd. by alkyl, alkoxy or halogen. (I) may be incorporated to liquid, pasty or solid cosmetic compsns. Uses include skin- and shaving water; sticks and lotions against insect bites; shaving- and baby powders, creams or lotions. Pref. use is in sun-protective and anti-sunburn compsns., presents as aq. emulsions oils or pastes. (I) have good anti-burning activity, are non-toxic, do not irritate skin and are easily worked into cosmetic compsns. In an example 7-isopropyl-8,8-dimethyl-6,10-dioxaspiro 4,5 -decane, (I') was pred. by acid condensation of cyclopentanone, 2,2,4-trimethylpentane-1,3-diol and triethyl orthoformate. 5% (I') in vaseline inhibited UV. oedema of hairless mouse by 44% in 30 hrs.

Description

'' Anti-inflammatory agents for cosmetic preparations "the subject of Invention are anti-inflammatory agents for cosmetic preparations, in particular for Sun protection and sunburn control preparations based on spiroketals of cyclic ones Ketones.

It has been found that spiroketals of the general formula in which R1 - R6 independently represent a hydrogen atom, an alkyl radical with 1 to 8 carbon atoms or a hydroxyalkyl group with 1 to 4 carbon atoms, m for the numbers 0, 1 or 2 and y for an alkylene radical of the general formula in which R - R18 is a hydrogen atom, an alkyl radical having 7 1 to 4 carbon atoms or a halogen atom, n and p are the numbers O or 1 and q are the numbers O-9, the radicals R9 and R10 including the double bond being one o-phenylene radical optionally substituted by an alkyl, an alkoxy group or a halogen atom, are outstandingly suitable as anti-inflammatory agents for cosmetic preparations.

The products are of particular importance as anti-inflammatory Agents in sunscreen or sunburn control agents. When used in The anti-inflammatory agents according to the invention are agents for preventing sunburn Products preferably in combination with conventional ultraviolet filter substances used.

The production of those to be used according to the invention as anti-inflammatory agents Spiroketale can be made by methods known per se. So let yourself be Example from the corresponding cyclic ketones and diols by azeotropic water separation win, as shown in the monograph Organikum, organic-chemical basic internship, VEB-Verlag der Wissenschaften (1968), p. 379 is described. Another procedure consists in the condensation of the cyclic ketone with the diol with trimethyl orthoformate or triethyl orthoformate as described by S.R. Sandler and W. Karo in Organic Functional Group Preparation Vol. 12, III, Academic Press, New York, London (1972), pp. 2-70 is presented in detail.

As cyclic ketones, those to be used according to the invention for the production of Spiroketals can be used, for example, cyclobutanone, cyclopentanone, 2-methyl-, 3-methyl-, 2,3-dimethyl-, 3,4-dimethyl-, 2,5-dimethyl-, 2-ethyl-, 2-propylcyclopentanone, 2-cyclopentenone, 3-methyl-2-cyclopentenone, cyclohexanone, 2-methyl-, 3-methyl-, 4-methyl-, 2,6-dimethyl-, 2,4-dimethyl-, 4,4-dimethyl-, 2,2,6-trimethyl-, 2,4,6-trimethyl-, 2,4,4-trimethyl-, 3,3,5,5-tetramethyl-cyclohexanone, 2,3,4-cyclohexenone, 3-methyl-2-cyclohexen-1-one, 2,3,4-hydroxy-cyclohexanone, isophorone, 2-chloro-cyclohexanone, 4-tert. Butyl-cyclohexanone, Cycloheptanone, 2-cyclohepten-1-one, 2-methyl-cycloheptanone, cyclooctanone, 2-methyl-cyclooctanone, Cyclononanone, cyclodecanone, cycloundecanone, cyclododecanone should be mentioned.

As diols, those to be used according to the invention for the production of the Spiroketals can be used, for example, ethylene glycol, 1,2-, 1,3-propylene glycol, 1,2-, 1,3-, 1,4-, 2,3-butylene glycol, 2-methyl-2,3-butylene glycol, Pinacol, hexane-1,2-, 1,3-, 1,4-, 2,4-diol, pentane-1,2-, 1,3-, 1,4-, 2,4-diol, 2, 3-methylpentane-2,4-diol, 2,2-dimethyl-, 2,2-diethyl-pentane-2,4-diol, 2,2-dimethyl-, 2,2-diethyl-, 2-ethyl-2-methyl-, 2-methyl-2-propyl-, 2-ethyl-2-butyl-, 2-hydroxymethyl-2-methyl-propane-1,3-diol, Glycerine, 2,2,4-trimethyl-pentane-1,3-diol, 2-methyl-, 2-ethyl-, 2,2-dimethyl-hexane-1,3-diol, List octane-1,2-diol, decane-1,2-diol.

Compounds to be used according to the invention are, for example 7-isopropyl-8,8-dimethyl-6,10-dioxa-spiro [4.5] -decane, 2,3,7-trimethyl-1,4-dioxa-spiroL4,4 -nonane, 2,8,8-trimethyl-7-isopropyl-6,10-dioxa-spiro [4,5] -decane, 1,4-dioxa-spiro [4,5] -decane, 2-methyl-1,4-dioxa-spiro [4,5] -decane, 2,3-dimethyl-1,4-dioxa-spiro [4,5] -decane, 2,4-dimethyl-1,5- dioxa-spiro [5,5] -undecane, 2-isopropyl-3,3-dietyl-1,5-dioxa-spiro, 51-undecane, 3,3-dimethyl-1,5-dioxa-spiro [5,5] -undecane, 2,3,6-trimethyl-1,4-dioxa-spiro [4,5] -decane, 1-isopropyl-3,3,7-trimethyl-1,5-dioxa-spiro [5,5] -undecane, 2,3,7-trimethyl-1,4-dioxa-spiro [4,5] -decane 2-isopropyl-3,3,8-trimethyl-1,5-dioxa-spiro [5,5] -undecane, 2,3,9-trimethyl-1,4-dioxa-spiro [4,5] -decane, 2-isopropyl-3,3,9-trimethyl-1,5-dioxa-spiro [5,5] -undecan, 2,6,10-trimethyl-1,4-dioxa-spiro [4,5] -decane, 2-isopropyl-3,3,7, ll-tetramethyl-1,5-dioxa-spiro [5,5] - undecan, 2,3,7,7,9-pentamethyl-1,4-dioxaspiro [4,5] decane, 2,4,8,8,10-pentamethyl-1,5-dioxaspiro [5,5] undecan, 2-isopropyl-3,3,8,8,10-pentamethyl-1,5-dioxa-spiro [5,5] undecane, 8-tert-butyl-1 , 4-dioxaspiro [4,5-decane, 2-methyl-8-tert-butyl-1,4-dioxaspiro [4,5] -decane, 2,3-dimethyl-8-tert.

butyl-1,4-dioxa-spiro [4,50-decane, 2,4-dimethyl-9-tert-butyl-1,5-dioxa-spiro [5,5] -undecane, 2,3,4-trimethyl-9-tert-butyl-1,5-dioxa-spiro [5,5] -undecane, 2,2,4-trimethyl-9-tert-butyl-1,5- dioxa-spiro [5,5] -undecane, 2-isopropyl-3,3-dimethyl-9-tert-butyl-1,5-dioxaspiro [5,5] -undecane, 3,3-dimethyl-9-tert.

butyl-1,5-dioxa-spiro [5,5] -undecane, 2,3-dimethyl-1,4-dioxaspiro {4,6] -undecane, 2-isopropyl-3,3-dimethyl-1,5-dioxa-spiro [5,6] -undecane, 1,4-dioxa-spiro [4,7] -dodecane, 2,3-dimethyl-1,4-dioxa-spiro E4, 71-dodecane, 2-isopropyl-3,3-dimethyl-1,5-dioxaspiro [5,7] -tridecane, 2-methyl-1,4-dioxa-spiro [4, 11] -hexadecane, 2,3-dimethyl-1,4-dioxa-spiro [4,11] -hexadecane, 2-isopropyl-3,3-dimethyl-1,5-dioxaspiro [5.11] -heptadecane, 2-isopropyl-3,3-dimethyl-7-chloro-1,5-dioxaspiro [5.5 ] -undecane, 2-methyl-6,7-benzo-1,4-dioxa-spirot4,5] -decane, 2-isopropyl-3,3-dimethyl-6,7-benzo-1,5-dioxa-spiro [5.5 ] -undecane, 2,8-Dimethyl-6,7-benzo-1,4-dioxa-spiro [4,5] -decane, 6-methoxy-1-tetralone-1,2-propylene ketal represent.

The compounds to be used according to the invention are colorless to slightly yellowish, crystalline or liquid substances that are characterized by good anti-inflammatory effect with good physiological tolerance, in particular good skin tolerance, excel and work well into cosmetic basics permit.

When used in sunscreens that help prevent sunburn serve, the Spiroketals to be used according to the invention are preferably used in combination used with conventional ultraviolet filter substances, such as ethyl p-aminobenzoate, propyl ester, butyl ester, isobutyl ester, monoglycerol ester, ethyl p-dimethylaminobenzoate, -amyl ester, p-Diethylaminobenzoic acid ethyl ester, amyl ester, salicylic acid menthyl ester, homomenthyl ester, -ethylene glycol ester, -glycerol ester, -2-ethylhexyl ester, -tert.butylester, -bornylester, -phenyl ester, triethanolammonium salt of salicylic acid, anthranilic acid menthyl ester, -bornyl ester, p-methoxycinnamic acid 3-ethoxyethyl ester, -2-ethylhexyl ester, p-acetamidocinnamic acid isopropyl ester, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxy-benzophenone, 4-phenylbenzophenone, 2-hydroxy-4-methoxy-benzophenone-5-sulfonic acid, 4-phenylbenzophenone-2-carboxylic acid isooctyl ester, 7-ethylamino-4-methylcoumarin, 7, 8-dihydroxycoumarin, 6, 7-dihydroxycoumarin, 7-hydroxycoumarin, 4-methyl-7-hydroxycuarine, 2-phenyl-benzimidazole-5-sulfonic acid, sodium 3,4-dimethoxyphenyl glyoxylate, Butylbenzalacetone, benzalacetophenone, 3-benz-lidene-D, L-camphor, 3- (p-methylbenzylidene) -D, L-camphor and urocanic acid.

When used as anti-inflammatory substances, the inventive Spiroketals incorporated into liquid, pasty or solid cosmetic preparations such as aqueous solutions, aqueous suspensions, emulsions, solutions in organic solvents, oils, ointments, creams, pens or powders. The preparations can serve a wide variety of purposes, such as general skin waters with anti-inflammatory Effect, aftershave, water, pens or lotions against insect bites, shaving powder, Baby powders, creams or lotions, especially as aqueous, emulsion-like, oily or pasty sunscreen or sunburn control agents.

When used as anti-inflammatory substances, the Spiroketals according to the invention in amounts of 0.01 to 10 percent by weight, preferably 0.5 to 5 percent by weight, based on the total formulation of the cosmetic agent, used. Are the Spiroketals according to the invention in sunscreens in combination with If UV filter substances are used, the amount of UV filter substances is 1 to 10 percent by weight, preferably 2 to 6 percent by weight, based on the total Sunscreen.

The following examples are intended to illustrate the subject matter of the invention in greater detail explain without, however, restricting it to this.

EXAMPLES First of all, the production of the to be used according to the invention should be Spiroketals are described.

A) 7-Isopropyl-8,8-dimethyl-6,10-dioxa-spiro [4,5] -decane A mixture from 16.8 g (0.2 mol) of cyclopentanone, 29.2 g (0.2 mol) of 2,2,4-trimethylpentane-1,3-diol, 29.6 g (0.2 mol) of triethyl orthoformate and 0.1 g of p-toluenesulfonic acid was left to stand overnight. The volatile constituents were then distilled off (Bath temperature 1000C), the residue taken up in ether, the solution with soda solution washed and dried over sodium sulfate.

After distilling off the ether, the mixture was under reduced pressure fractionally distilled. There were 27.3 g (65% of theory) of 7-isopropyl-8,8-dimethyl-6,10-dioxaspiro [4.5] decane with a boiling point of 10900 / 5.5 Torr and a refractive index n20: 1.4570.

The following Spiroketals were produced in an analogous manner.

B1) 2,3,7-trimethyl-1,4-dioxaspiro [4,4] -nonane bp 370C / 1 torr; n20: 1.4380 B2) 2,8,8-trimethyl-7-isopropyl-6,10-dioxa-spiro [4,5] -decane bp 10100 / 3.2 torr; n20: 1.4543 C1) 1,4-dioxa-spiro [4.5] decane bp 480C / 2.3 torr; n20 : 1.4582 C2) 2-methyl-1,4-dioxa-spiro [4.5] decane bp 520C / 2.6 torr; n20: 1> 4515 C3) 2,3-dimethyl-1,4-dioxa-spiro [4.5] decane bp 360C / 0.1 torr; C4) 2,4-dimethyl-1,5-dioxaspiro [5,5] undecane Bp 1060C / 15 torr; n20: 1.4586 C2) 2-isopropyl-3,3-dimethyl-1,5-dioxa-spiro [5,5] undecane Bp 108 ° C / 3.5 torr; n20: 1.4657 C6) 3,3-dimethyl-1,5-dioxa-spiro [5,5] -undecane Bp 680C / 1.3 Torr; n20: 1.4631 D1) 2,3,6-trimethyl-1,5-dioxa-spiro [4,5] -decane Bp 64 ° C / 2.3 Torr; n20: 1.4527 D2) 2-isopropyl-3,3,7-trimethyl-1,5-dioxa-spiro [5,5] -undecane Bp 111-115 ° C // 2.6 torr; n20: 1.4665 E1) 2,3,7-trimethyl-1,5-dioxa-spiro [4,5] -decane Bp 83 ° C / 2.7 torr; n20: 1.4475 E2) 2-isopropyl-3,3,8-trimethyl-1,5-dioxa-spiro [5,5] -undecane Bp 1170C / 3.5 torr; n20: 1.4627 F1) 2,3,8-trimethyl-1,4-dioxa-spiro [4,5] -decane Bp 56-59 ° C / 1.5 torr; n20: 1,4485 F2) 2-isopropyl-3,3,9-trimethyl-1,5-dioxa-spiro [5.5] -undecane bp 129 ° C / 3.2 torr; n20: 1.4615 G1) 2,6,10-trimethyl-1,4-dioxa-spiro [4,5] -decane Bp 720r / 5.6 torr; n20: 1.4553 G2) 2-isopropyl-3,3,7,11-tetramethyl-1,5-dioxa-spiro [5,5] undecane Bp 1470C / 3.5 torr; n20: 46.75 H1) 2,3,7,7,9-pentamethyl-1,4-dioxa-spiro [4.5] decane Bp 37-38 ° C / 0.01 torr; n20: 1.4470 H2) 2,4,8,8,10-pentamethyl-1,5-dioxa-spiro [5,5] -undecane Bp 54-560C / 0.01 Torr; n20: 1.4537 H3) 2-isopropyl-3,3,8,8,10-pentamethyl-1,5-dioxa-spiro [5,5] -undecane Bp 76-78 ° C / 0.05 torr; n20: 1.4632 I1) 8-tert-butyl-1,4-dioxa-spiro [4.5] decane Bp 99 ° C / 3.5 torr; n20: 1.4663 I2) 2-methyl-8-tert-butyl-1,4-dioxa-spiro [4.5] decane Bp 940C / 3.2 Torr; n20: 1.4600 I3) 2,3-dimethyl-8-tert-butyl-1,4-dioxa-spiro [4.5] decane Bp 960C / 1.5 Torr; n20: 1.4603 I4) 2,4-dimethyl-9-tert-butyl-1,5-dioxa-spiro [5,5] -undecane Bp 940C / 1.0 Torr; 2,3,4-Trimethyl-9-tert-butyl-1,5-dioxa-spiro [5,5] -decane bp. 960C / 1.4 Torr; n20: 1.4612 (16) 2,2,4-trimethyl-9-tert-butyl-1,5-dioxa-spiro [5,5] -undecane Bp 98 ° C / 0.5 torr; n20: 1.4600 I7) 2-isopropyl-3,3-dimethyl-9-tert-butyl-1,5-dioxa-spiro [5,5] -undecane Bp 1470C / 3.5 torr; M.p. 27-33 ° C, n20: 1.4675 I8) 3,3-Dimethyl-9-tert-butyl-1,5-dioxa-spiro [5,5] -undecane M.p. 76-77 ° C 19) 2,3-dimethyl-1,4-dioxa-spiro [4,6] -undecane bp 860 ° C / 4.0 torr; n20: 1.4591 I10) 2-isopropyl-3,3-dimethyl-1,5-dioxa-spiro [5,6] -undecane bp 1160C / 2.3 torr; n20: 1.4711 K1) 1,4-dioxa-spiro [4.7] -dodecane bp 880C / 6.0 torr; n20: 1.4770 K2) 2,3-dimethyl-1,4-dioxa-spiro [4.7] -dodecane bp 750C / 0.8 torr n20: 1.4683 K3) 2-isopropyl-3,3-dimethyl-1,5-dioxa-spiro [5.7] -tridecane bp 141 ° C / 2.2 torr; n20: 1.4768 L1) 2-methyl-1,4-dioxa-spiro [4.11] -hexadecane bp 990C / 0.005 torr; Melting point 40-43 ° C L2) 2,3-dimethyl-1,4-dioxa-spiroC4,11) -hexadecane bp. 1200C / 0.05 torr; L3) 2-isopropyl-3,3-dimethyl-1,5-dioxa-spiro [5,11] -heptadecane Bp 187 ° C / 3.5 Torr; n20: 1.4868 M) 2-isopropyl-3,3-dimethyl-7-chloro-1,5-dioxa-spiro [5.5] undecane Bp 142 ° C / 1.7 torr; n20: 1.4838 N1) 2-methyl-6,7-benzo-1,4-dioxa-spiro [4.5] decane Bp 95 ° C / 0.3 Torr, n20: 1.5358 N2) 2-isopropyl-3,3-dimethyl-6,7-benzo-1,5-dioxa-spiro [5,5] undecane Bp 15400 / 2.1 torr; M.p. 52-660C O) 2,8-dimethyl-6,7-benzo-1,4-dioxa-spiro [4,5] -decane Bp 133 ° C / 4.0 Torr; n20: 1.5318 P) 6-methoxy-1-tetralone-1,2-propylene-ketal bp. 1460C / 0.9 torr.

The following are intended to highlight the anti-inflammatory properties of the compounds to be used according to the invention and their suitability for cosmetic Show preparations, in particular sunscreen or sunburn control agents.

In the investigations listed below, those according to the invention Spiroketals to be used have been tested for their anti-inflammatory properties. An exploratory study of its toxicity was previously carried out in order for the further examinations to be able to determine the test dosages.

As a test to assess the suitability of the connections the rat paw test was used to inhibit the inflammation caused by sunburn used as described by F. Kemper in the journal "Arzneimittelforschung" 10 (1960), P. 777 is described. To generate the edema, the test animals were given 0.1 ml 6% dextran solution in the right hind paw approx. 5 mm deep between the second and third toe injected. Only the dextran solution was administered during the control animals the test animals received the various 30 minutes before their injection Test substances injected in the amount given in the table or administered orally. The volume of the paws was compared to that of F. Kemper and G. Amelin in the "Journal for the Entire Experimental Medicine" 131 (1959), Page 407 described in more detail electrical volume measuring device determined. The measurements were made 30 minutes before injections of the dextran solution, i.e., at the time of administration the test substances to the test animals and 30 minutes after the injection of the dextran solution.

For comparison, the left untreated paw was always named Measured times. From the values for the swelling in animals exposed to the test substance had been treated and untreated animals 30 minutes after the dextran injection the degree of inhibition of the edema was calculated as a percentage of the swelling which occurred in animals that had not received the test substance.

As a further rat paw test, that of 0.H. Winter in the J. of pharmac. and experiment. Therap. Vol. 141 (1963) page 369 described so-called Amputation methodology used. In this procedure, the test animals become three Hours after the injection of the inflammatory substance killed and the paw weights are determined. In these studies it is used as an inflammatory product Carrageenin used. Inhibition of the development of the edema of the rat paw through the test substance administered orally one hour before the inflammation was triggered is used as an indicator of the effect and is expressed as a percentage.

Based on general experience, the results of the rat paw tests as a basis for evaluating a compound as a sunburn control agent to serve.

A UV test was also carried out on hairless mice, which was also carried out a statement about the usefulness of the substances as sunburn control agents allowed. The hairless mice were backed with a UV lamp from a distance of 60 cm Irradiated for 30 minutes, causing skin inflammation. Both The test substances were administered to test animals through the interperitoneal route Injection or per os following the irradiation, while the control animals received no follow-up treatment.

The dosage of the test substances was the same as in the rat paw test. The degree of edema formation was determined by measuring the thickness of the skin folds after 30 hours certainly. From the comparison of the change in skin fold thickness due to radiation in treated test animals with changes in the thickness of the skin folds in animals, which were irradiated but not treated, the degree of the percentage Inhibition of the erythema determined, which is given in the table below.

The UV erythema test was carried out on guinea pigs as a further test. For this purpose, the backs of the test animals are sheared and treated with freed from hair with a depilatory cream. The test animals are then 8 minutes irradiated and following the irradiation on the marked test fields with treated with the test solutions or ointments. The second application takes place after 30 minutes, the third and subsequent treatments follow every 60 minutes. After 6 Hours from the irradiation, the animals are washed, dried and visually assessed. The evaluation is repeated the next morning and from both evaluations of the Average calculated for each substance. They are considered to be irradiated and untreated Control points selected the two radiation spots directly behind the ears. Whose Redness intensity is set equal to 0. Disappearance of redness the treated areas are marked with plus points up to +4 (no more stain recognizable) and Intensification of the redness rated with minus points up to -4 (blistering}. The sum of the evaluations from both evaluations, set in relation to the number of animals times 4 as the maximum achievable (= 100%), gives the percentage inhibition value of the substance. The inhibition values determined in this way are shown in the table below under the "UV erythema in guinea pigs" section.

In the - as described above - carried out examinations the values listed in the table below were determined for the individual substances.

Table 1 Anti-inflammatory properties and orientational toxicity Test sub-orienting rat paw test UV edema UV erythema punch toxicity LD50 Haarlsoe mouse guinea pig (g / kg) carrageenin edema dextran edema 5% in vase 5% line in tincture Dose dose inhibition (%) inhibition (%) po inhibition po inhibition and 30 h (mg / kg) (%) (mg / kg) (%) A> 1.0 1000 66 1000 27 44 33 B> 1.0 1000 14 1000 13 16 - B2> 1.0 1000 66 1000 28 59 44 C1> 1.0 1000 16 1000 12 31 29 C2 1.0 1000 35 500 23 49 33 C3> 1.0 1000 16 1000 12 13 44 C4> 1.0 1000 30 1000 18 9 29 C5> 1.0 1000 41 1000 18 33 29 C6> 1.0 1000 24 1000 25 9 - D1> 1.0 1000 14 1000 30 36 - D2> 1.0 1000 45 1000 16 65 57 E1> 1.0 1000 27 1000 17 37 - E2> 1.0 1000 41 1000 29 43 34 F2> 1.0 1000 20 1000 29 15 30 Table 1 (continued) Anti-inflammatory properties and orientational toxicity Test sub-orienting rat paw test UV edema UV erythema punch toxicity LD50 Haarlsoe mouse guinea pig (g / kg) carrageenin edema dextran edema 5% in vase 5% line in tincture Dose dose inhibition (%) inhibition (%) po inhibition po inhibition and 30 h (mg / kg) (%) (mg / kg) (%) H1> 1.0 1000 35 1000 12 - 32 H2> 1.0 1000 10 - - - 39 H3> 1.0 1000 10 - - - 40 I1> 1.0 1000 67 500 38 38 30 500 48 I2> 1.0 1000 50 500 24 26 34 500 44 I3> 1.0 1000 56 500 38 24 37 500 52 I4> 1.0 1000 38 500 32 - - I5> 1.0 1000 59 500 21 19 31 I6> 1.0 1000 20 - - 18 - I8> 1.0 - - - - 31 33 I9> 1.0 1000 19 500 34 49 30 I10> 1.0 1000 19 500 15 22 34 K2> 1.0 1000 33 500 13 11 30 K3> 1.0 1000 14 1000 20 17 47 L1> 1.0 - - 500 21 - 39 L2> 1.0 1000 60 500 20 36 34 L3> 1.0 1000 23 1000 26 20 - under table @@@ @@ @@ Some examples of cosmetic preparations containing substances according to the invention are listed below.

1.) To produce a sun protection oil, 20 g of 2,8,8-trimethyl-7-isopropyl-6, 10-dioxaspiror4,51-decane 30 g of menthyl salicylate in 100 g of paraffin oil under warming suspended, and then at about 250C with the following other ingredients 300 g vegetable oil containing lecithin 400 g olive oil 100 g isopropyl myristinate 100 g Purcellin oil mixed intimately 2.) For the production of a sunburn powder 40 g of 2-methyl-1,4-dioxa-spiro [4,11J-hexadecane in a powder mixer intensively with 400 g rice starch 400 g colloidal clay 100 g lycopodium 100 g talc in homogeneous Distribution brought.

3.) Be used to make an anti-inflammatory aftershave 30 g of 2-isopropyl-3,3,7-trimethyl 1,5-dioxa-spiro-undecane together with a solution of 5 g citric acid 30 g glycerine in 100 g hammamelis water with a perfumed, 80% alcoholic preparation combined to a total of 1000 g.

4.) 40 g of glycerol monostearate are used to produce a sun protection cream 160 g beeswax 420 g mineral oil 50 g ceresin 50 g of an absorption base based on of cholesterol, beeswax, stearyl alcohol and petrolatum 30 g of 2-isopropyl-3,3,8,8,10-pentamethyl-1,5-dioxaspiro L5,53-undecane 40 g benzyl salicylate melted together at 650C. In this warm Mixture becomes a mixture of 247 g of water heated to the same temperature 13 g of borax 2 g of p-oxybenzoic acid methyl ester incorporated with vigorous stirring, and the cream obtained is stirred further until it has reached room temperature.

5.) To produce a sun protection emulsion, an approx. 80 ° C heated mixture of 20 g glycerol monostearate 70 g stearic acid 30th g oleic acid 20 g cetyl alcohol 40 g 2-isopropyl-3,3-dimethyl-1,5-dioxaspirol, 73-tridecane 40 g phenyl salicylate with vigorous stirring a mixture of 800 g water 10 g glycerine and given 9 g of triethanolamine. The lotion obtained is then stirred while cold.

The above emulsion can also be used with the use of a propellant gas Pack in a ratio of 80 parts lotion: 20 parts propellant in aerosol form.

Instead of the Spiroketals used in the aforementioned recipes The other Spiroketals listed above can also be used with equal success be used.

Claims (5)

Pat ent claims Use of spiroketals of the general formula in which R1 - R6 independently represent a hydrogen atom, an alkyl radical with 1 to 8 carbon atoms or a hydroxyalkyl group with 1 to 4 carbon atoms, m for the numbers 0, 1 or 2 and y for an alkylene radical of the general formula in which R7-R18 is a hydrogen atom, an alkyl radical with 1 to 4 carbon atoms or a halogen atom, n and p denote the numbers 0 or 1 and q denote the numbers O-9, the radicals Rg and R10, including the double bond, optionally denoting one can form o-phenylene radical substituted by an alkyl, an alkoxy group or a halogen atom, are used as anti-inflammatory agents in cosmetic preparations. 2) Use of spiroketals according to claim 1 as anti-inflammatory agents in sunscreen or sunburn control agents. 3) Use of Spiroketalen according to claim 1 and 2 in an amount from 0.01 to 10 percent by weight, preferably 0.5 to 5 percent by weight, based on the entire preparation. 4) Use of spiroketals according to claims 1-3 as anti-inflammatory agents in sunscreens in combination with common UV filter substances. 5) Use of Spiroketalen according to claim 4, wherein the amount of UV filter substance 1 to 10 percent by weight, preferably 2 to 6 percent by weight, based on the total sunscreen product.