DE10028764A1 - Carbamate compound, useful as a fragrant additive for cleaning, washing and dishwashing agents, is prepared by reaction of free isocyanate group containing compound with fragrant alcohol - Google Patents

Abstract

A compound (I) is prepared by reaction of at least one free isocyanate group containing organic compound with a fragrant alcohol R<1>OH under conventional conditions to form carbamate groups -NHC(=O)-OR<1>. An Independent claim is included for a composition (II) containing the compound (I).

Description

The invention relates to urethane compounds which have organoleptically active scent alcohol hole release, a process for producing such urethane compounds as well the use of the same in cosmetic compositions, cleaning agents detergent, fabric softener, hand detergent and dishwashing detergent together settings for automatic dishwashers.

A basic method for the release of organoleptically active substances zen, z. B. from detergents, this is added directly to the application formulation Zen. The disadvantage of this method is the immediate release of the fragrance from the Formulation, which leads to a temporary fragrance effect and thus the storability of the wording is greatly reduced: attempts to encapsulate such sub Punching or injecting into cyclodextrins were found to be unsuccessful or due to the high raw material prices as uneconomical. The proved to be more advantageous Immobilization through chemical derivatization. So WO 95/04809 teaches slow cleavage of fragrance alcohol esters using lipases, which lasts a long time evokes the scent. In WO 97/30687 and EP 0816322 the connection to Sul is made fonates, sulfates and phosphates, whereby similar effects are achieved. More poss Opportunities for the targeted slow release of fragrance alcohols are betaine esters, as shown in EP 0799885, α-tertiary carbon esters in WO 98/07810, β-keto esters in WO 98/07813 or linear or cyclic acetals.

The present invention has for its object to new substance classes targeted release of fragrance alcohols over a longer period of time Semi note. According to the invention, the object is achieved by chemical bonding a fragrance alcohol component to an isocyanate to form a urethane.

In particular, the invention relates to a compound obtainable by reacting a organic compound containing at least one free isocyanate group a scented alcohol R'OH under normal conditions to form carbamate Groups -NHC (= O) -OR '.  

The organic compound containing free isocyanate groups is selected from the group consisting of mono-, di- and triisocyanates and polyurethane primer prepare.

In one embodiment, the invention thus relates to a compound of the formula

R [-NH-C (= O) -OR '] _n

where n = 1, 2 or 3 and R is derived from aliphatic, alicyclic or a aromatic mono-, di- or triisocyanates with 1 to 30 carbon atoms.

The aliphatic and alicyclic isocyanates preferably contain 1 to 18 and particularly preferably 6 to 12 carbon atoms. The aromatic isocyanates ent preferably hold at least 5, particularly preferably at least 6 and preferably at most 18 carbon atoms.

For n = 1, R is derived particularly preferably from monoisocyanates of group 1- Hexane isocyanate, 1-heptane isocyanate, 1-octane isocyanate, 1-non-isocyanate, 1-de isocyanate, 1-undecane isocyanate, 10-undecene-1-isocyanate, 1-dodecane isocyanate, 1-tridecane isocyanate, 1-tetradecane isocyanate, 1-pentadecane isocyanate, 1-hexad isocyanate, 1-heptadecan isocyanate, 1-octadecan isocyanate, 9-cis-octadecen-1- isocyanate, 9-trans-octadecene-1-isocyanate, 9-cis-octadecene-1,12-diisocyanate, all-cis- 9,12,15-octadecadiene-1-isocyanate, all-cis-9,12,15-octadecatriene-1-isocyanate, 1- Nonadecan isocyanate, 1-eicosan isocyanate, 9-cis-eicosen-1-isocyanate, 5,8,11,14-egg cosatetraen-1-isocyanate, 1-heneicosan isocyanate, 1-docosan isocyanate, 13-cis-Do cosen-1-isocyanate, 13-trans-docosen-1-isocyanate.

For n = 2, R is particularly preferably derived from diisocyanates from the group consisting of tolylene diisocyanate, bitoluylene diisocyanate, dianisidine diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, m-phenylene diisocyanate, m-xylylene diisocyanate, C ₁ -C ₆ alkylbenzene diisocyanate, 2,4-chlorobenzene diisocyanate, cyclohexylmethane diisocyanate, 3,3'-dimethoxydiphenylmethane-4,4'-diisocyanate, 1-nitrobenzene-2,4-diisocyanate, 1-alkoxybenzene-2,4-diisocyanate, ethylene diisocyanate, propylene diisocyanate, cyclohexylene-1,2-diisocyanate, 3, 3'-dichloro-4,4'-biphenylendii socyanate, diphenylene diisocyanate, 2-chlorotrimethylene diisocyanate, butylene-1,2-dii socyanate, ethylidene diisocyanate, diphenylmethane-4,4'diisocyanate, diphenylethanedii socyanate, 1,5-naphthalenediisocyanate, cyclohexophorone diisocyanate, and cyclohexane diisocyanate anat.

For n = 3, R is derived particularly preferably from the triisocyanates of the group Triphenylmethane triisocyanate, diphenylmethane triisocyanate, butane-1,2,2-triisocyanate, Trimethylolpropane tolylene diisocyanate trimer, 2,4,4'-diphenyl ether triisocyanate, poly methylene polyphenyl isocyanate.

The buttocks which can be used according to the invention and form the polyurethane backbone R. lyurethanes have a free isocyanate group content of 0.1 to 20% by weight. %, preferably 0.1 to 15% by weight, particularly preferably 0.1 to 10% by weight, based on the polyurethane backbone. The determination of the salary of Free isocyanate groups in polyurethanes are known to the person skilled in the art. This can e.g. on Gerhard W. Becker (ed.), Kunststoff-Handbuch, volume 7: "Polyurethane" (published by Günter Oertel), 3rd edition, Munich 1993 become. The polyurethanes also preferably have an average molecular weight weight of 500 to 30,000, preferably 500 to 20,000, particularly preferably 500 up to 10,000.

The polyurethane backbone can be known in the art ren (see Gerhard W. Becker [ed.], Kunststoff-Handbuch, Volume 7: "Polyurethane" [ed. by Günter Oertel], 3rd edition, Munich 1993, or Ullmann's Encyclopedia of Industrial Chemistry, Verlag Chemie, 1992, Volume 21, "Polyurethane") by Um Settlement of polyisocyanates with polyols are formed. To the polyisocyanates can be referred to the above di- and triisocyanates.  

The polyurethane backbone can also contain ionic functional groups wear, such as the (COO -) - or protonated with the formation of ami no These ionic groups can be reacted with the isocyanates speaking functional groups carrying polyols.

The polyurethane backbones are preferably produced by reaction of the Polyisocyanates with polyols selected from the group consisting of Ethylene glycol, propylene glycol, butylene glycol, and neopentyl glycol, pentanediol-1,5,3- Methylpentanediol-1,5, bisphenol A, 1,2- or 1,4-cyclohexanediol, caprolactone diol (Reaction product of caprolactone and ethylene glycol), hydroxyalkylated bisphe nole, trimethylolpropane, trimethylolethane, pentaerythritol, 1,6-hexanediol, heptane diol-1,7, octanediol-1,8, butanediol-1,4, 2-methyloctanediol-1,8, nonanediol-1,9, decane diol-1,10, cyclohexanedimethylol, di-, tri- and tetraethylene glycol, di-, tri- and Tetrapropylene glycol, polyethylene and polypropylene glycols with a medium mo molecular weight from 150 to 15,000, trimethylolethane, trimethylolpropane and pentae rythritol. The polyols mentioned can also be used either individually or in any amount mixture are used with each other. For the formation of ionic groups in the Polyurethane backbone can dihydroxy the reaction to a suitable extent carboxylic acids containing up to 24 carbon atoms or diethanolamine, Trietha nolamine or dimethylethanolamine can be added. Preferred dihydroxy car bonic acids are 2,2-di (hydroxymethyl) acetic acid, 2,2,2- Tri (hydroxymethyl) acetic acid, 2,2-di (hydroxymethyl) propionic acid, 2,2- Di (hydroxymethyl) butanoic acid, 2,2-di (hydroxymethyl) pentanoic acid.

The rest R 'is derived from a fragrant alcohol R'OH, which is selected from the Group consisting of amyl alcohol, 2-hexyl alcohol, hexyl alcohol, heptyl alcohol, Octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, lauryl alcohol, myristical alcohol, 3-methyl-but-2-en-1-ol, 3-methyl-1-pentanol, cis-3-hexenol, cis-4-hexenol, 3,5,5-trimethylhexanol, 3,4,5,6,6-pentamethylheptan-2-ol, citronellol, geraniol, oct- 1-en-3-ol, 2,5,7-trimethyl octan-3-ol, 2-cis-3,7-dimethyl-2,6-octadien-1-ol, 6-ethyl-3- methyl-5-octen-1-ol, 3,7-dimethyl-oct-3,6-dienol, 3,7-dimethyloctanol, 7-methoxy 3,7-dimethyl-octan-2-ol, cis-6-nonenol, 5-ethyl-2-nonanol, 6,8-dimethyl-2-nonanol,  2,2,8-trimethyl-7 (8) -nonen-3-ol, nona-2,6-dien-1-ol, 4-methyl-3-decen-5-ol, 5-dec- 9-en-1-ol, benzyl alcohol, 2-methyl-undecanol, 10-undecen-1-ol, 1-phenylethanol, 2-phenylethanol, 2-methyl-3-phenyl-3-propenol, 2-phenylpropanol, 3-phenylpro panol, 4-phenyl-2-butanol, 2-methyl-5-phenylpentanol, 2-methyl-4-phenylpentanol, 3- Methyl 5-phenylpentanol, 2- (2-methylphenyl) ethanol, 4- (1-methylethyl) benzyl methanol, 4- (4-hydroxyphenyl) butan-2-one, 2-phenoxyethanol, 4- (1-methylethyl) -2- hydroxy-1-methylbenzene, 2-methoxy-4-methylphenol, 4-methylphenol, anise alcohol, p-toluyl alcohol, cinnamon alcohol, vanillin, ethyl vanillin, eugenol, isoeugenol, thymol, Anethole, decahydro-2-naphthalenol, borneol, cedrenol, farnesol, fenchyl alcohol, Menthol, 3,7,11-trimethyl-2,6,10-dodecatrien-1-ol, α-ionol, tetrahydroionol, 2- (1,1- Dimethylethyl) cyclohexanol, 3- (1,1-dimethylethyl) cyclohexanol, 4- (1,1-dimethyl ethyl) -cyclohexanol, 4-isopropyl cyclohexanol, 6,6-dimethyl-bicyclo [3.3.1] hept-2-en- 2-ethanol, 6,6-dimethyl-bicyclo [3.1.1] hept-2-en-methanol p-menth-8-en-3-ol; 3,3,3,5- Trimethylcyclohexanol, 2,4,6-trimethyl-3-cyclohexenylmethanol, 4- (1-methyl ethyl) cyclohexylmethanol, 4- (1,1-dimethylethyl) cyclohexanol, 2- (1,1-dimethylethyl) - cyclohexanol, 2,2,6-trimethyl-α-propyl cyclohexane propanol, 5- (2,2,3-trimethyl-3-. cyclopentenyl) -3-methylpentan-2-ol, 3-methyl-5- (2,2,3-trimethylcyclopent-3- enyl) pent-4-en-2-ol, 2-ethyl-4- (2,2,3-trimethylcyclopentyl-3-enyl) but-2-en-1-ol, 4- (5,5,6-trimethylbicyclo [2.2.1hept] -2-yl) cyclohexanol, 2- (2-methylpropyl) -4-hydroxy-4- methyl tetrahydropyran, 2-cyclohexylpropanol, 2- (1,1-dimethylethyl) -4-methyl cyclohexanol, 1- (2-tert-butyl-cyclohexyloxy) -2-butanol, 1- (4-isopropyl-cyclohexyl) - ethanol.

The invention also relates to a method for producing the above Scented alcohol urethanes by reacting at least one free isocyanate Group containing organic compound with a scented alcohol under R'OH usual conditions for the formation of a urethane in bulk or solution.

Such reactions, the setting and the determination of NCO contents are known to the person skilled in the art from the prior art (cf. Gerhard W. Becker [Ed.], Kunststoff-Handbuch, Volume 7: "Polyurethane" [ed. by Günter Oertel], 3.  Edition, Munich 1993, pages 11-21, 76-103 or Ullmann's Encyclopedia of Industrial Chemistry, Verlag Chemie, 1992, Volume 21, "Polyurethane".).

Regarding the isocyanates or basic polyurethane to be used according to the invention setup is referred to the above explanations.

Another object of the invention is the use of the invention Compounds in paints, adhesives, plastics, such as foils, as well as in cosmetics compositions such as deodorants, shampoos, creams, lotions, be ointments, ointments, powders and aerosols, hand and machine detergent compositions tongues and fabric softener compositions, detergents and cleaning agents, as well as in detergents and fabric softeners. The compounds of the invention the compositions mentioned in each case in effective amounts preferably 0.1 to 10 wt .-% based on the total amount of the composition tongue, added. With the compounds according to the invention are after application Fragrance release periods of up to four weeks can be achieved. The following examples serve to explain the invention.

Examples

• 1. 154 g of geraniol are placed in .70 g of methyl ethyl ketone and 84 g of HDI (Hexamethyl diisocyanate) was added dropwise at 100 ° C. in the course of 10 minutes. The The reaction is stopped after the NCO content has dropped below a value of 0.1% by weight drops. The solvents are removed and the residue is removed Methyl ethyl ketone recrystallized.
• 2. 154 g of citronellol are placed in 70 g of methyl ethyl ketone and 84 g of HDI within added dropwise at 100 ° C. for 10 minutes. The reaction is stopped after the NCO content drops below a value of 0.1% by weight. The solvents who removed and the residue recrystallized from methyl ethyl ketone.  
• 3. 156 g of menthol are placed in 70 g of methyl ethyl ketone and 84 g of HDI within added dropwise at 100 ° C. for 10 minutes. The reaction is stopped after the NCO content drops below a value of 0.1% by weight. The solvents who the removed and the residue recrystallized from ethanol.
• 4. 154 g of geraniol are placed in 100 g of methyl ethyl ketone and 211 g of lauryl isocy Anat added dropwise at 90 ° C within 20 minutes. Termination of the reaction takes place after the NCO content drops below a value of 0.1 wt .-%. The Lö solvents are removed and the residue is recrystallized from ethanol.
• 5. 154 g of geraniol are placed in 150 g of methyl ethyl ketone and 295 g of stearyl isocy Anat added dropwise at 90 ° C within 20 minutes. Termination of the reaction takes place after the NCO content drops below a value of 0.1 wt .-%. The Lö solvents are removed and the residue is recrystallized from ethanol.
• 6. 154 g of geraniol are placed in 100 g of methyl ethyl ketone and 295 g of oleyl isocya added dropwise at 90 ° C. within 20 minutes. The reaction was aborted follows after the NCO content drops below a value of 0.1% by weight. The Lö solvents are removed and the residue is recrystallized from ethanol.
• 7. 600 g of PEG 12000 are placed in 600 g of methyl ethyl ketone and slowly added 17 g HDI added at 80 ° C. As soon as the isocyanate content drops to 0.35 NCO wt. has fallen, 16 g of geraniol are added and 2 hours at the same temperature temperature stirred. The solvents are then removed and the back was recrystallized from ethanol.
• 8. 300 g of PEG 6000 are placed in 600 g of methyl ethyl ketone and slowly with 17 g HDI offset at 80 ° C. As soon as the isocyanate content fell to 0.66 NCO% by weight len, 16 g of geraniol are added and 2 hours at the same temperature rature stirred. The solvents are then removed and the residue recrystallized from ethanol.  
• 9. 200 g of PEG 4000 are placed in 600 g of methyl ethyl ketone and slowly with 17 g HDI offset at 80 ° C. As soon as the isocyanate content fell to 0.97 NCO% by weight len, 16 g of geraniol are added and 2 hours at the same temperature rature stirred. The solvents are then removed and the residue recrystallized from ethanol.
• 10. 5.25 g of diethanolamine are placed in 50 g of methyl ethyl ketone and slowly added 17 g HDI added at 80 ° C. As soon as the isocyanate content to 9.52 NCO wt .-% ge 16 g of geraniol are added and 2 hours at the same temperature rature stirred. The solvents are then removed and the residue recrystallized from ethanol.
• 11. 7.5 g of triethanolamine are placed in 150 g of methyl ethyl ketone and slowly added 25 g HDI added at 80 ° C. As soon as the isocyanate content to 8.64 NCO wt .-% ge 24 g of geraniol are added and 2 hours at the same temperature rature stirred. The solvents are then removed and the residue recrystallized from ethanol.
• 12. 7 g of dimethylolpropanoic acid are placed in 150 g of methyl ethyl ketone and long mixed with 17 g HDI at 80 ° C. As soon as the isocyanate content to 8.94 NCO 16% geraniol are added and 2 hours with the same cher temperature stirred. The solvents are then removed and the residue recrystallized from ethanol.

Examples of use

• 1. The initially odorless substance mentioned in synthesis example 1 is converted into a Dishwasher formula incorporated and in a commercially available dishwasher (Bosch S 712) tested. After the end of the rinse there is a pleasant geraniol scent found, which is still noticeable after 30 minutes.  
• 2. Shampoo formulations were produced in accordance with Table 1 below:
  Strands of hair (2 g) were pre-cleaned with an aqueous surfactant solution and then rinsed thoroughly.
  Then 1 g of the formulations of Examples A and B per gram of hair were applied to the hair tresses and also thoroughly rinsed out. After drying the locks of hair under air-conditioned conditions, oil was examined and assessed factorially.

Table 1

The formulation of Example B containing geraniol-HDI was treated Hair gave a long-lasting fragrance impression.

• 1. To check a possible improvement in the fragrance of detergent formulations gene by fragrance alcohol carbamates according to the invention were the following recipes 1 and 2 given in Table 1. The two re recipes differ only in the use of HDI geraniol.

Table 1

The following experimental design was used to measure a possible fragrance enhancement:
Items to be washed: terry towels, tea towels, prewashed with a fragrance-free formula, additional 3.5 kg of laundry;
Washing machine Miele W 918; Washing temperature: 60 ° C
Use of 75 g each of recipe 1 or 2.
Result: A smell of the wet and dry laundry by a total of 15 test subjects resulted in a more intense and pleasant scent impression on both wet and dry test laundry when using recipe 2.

Claims (29)

1. Compound obtainable by reacting at least one free isocya nat group-containing organic compound with a scented alcohol under R'OH usual conditions for the formation of carbamate groups -NHC (= O) -OR '. 2. Compound according to claim 1, characterized in that the free isocy organic compound containing anate groups is selected from the group consisting of mono-, di- and triisocyanates and polyurethane frameworks. 3. A compound according to claim 1 or 2 of the formula
R [-NH-C (= O) -OR '] _n
where n = 1, 2 or 3 and R is derived from aliphatic, alicyclic or aromatic mono-, di- or triisocyanates having 1 to 30 carbon atoms. 4. A compound according to claim 3, characterized in that the mono-, di- and triisocyanates are selected from the group consisting of 1-hexanisocyanate, 1-heptane isocyanate, 1-octane isocyanate, 1-nonanisocyanate, 1-decane isocyanate, 1-undecane isocyanate , 10-undecene-1-isocyanate, 1-dodecane isocyanate, 1-tridecane isocyanate, 1-tetradecane isocyanate, 1-pentadecane isocyanate, 1-hexadecane isocyanate, 1-heptadecane isocyanate, 1-octadecane isocyanate, 9-cis-octadecene-1 isocyanate, 9- trans-octadecene-1-isocyanate, 9-cis-octadecene-1,12-diisocyanate; all-cis-9,12,15-octa decadiene-1-isocyanate, all-cis-9,12,15-octadecatriene-1-isocyanate, 1-nonadecaniso cyanate, 1-eicosan isocyanate, 9-cis-eicosen-1- Isocyanate, 5,8,11,14-eicosatetraen-1-isocyanate, 1-heneicosan isocyanate, 1-docosariisocyanate, 13-cis-docosen-1-isocyanate, 13-trans-docosen-1-isocyanate, hydrogenated MDI ( H ₁₂ MDI, a cycloaliphatic compound), 1-methyl-2,4-diisocyanato-cyclohexane, 1,6-diisocyanato-2,2,4-tri methylhexane, 1,6-diisocyanato-2,4,4-trimethylhexane, 1-isocyanatomethyl-3-isocyanate-1,5,5-trimethyl-cyclohexane (isophorone diisocyanate = IPDI), butane-1,4-diisocyanate, hexamethylene diisocyanate (HDI), dicyclohexylmethane diisocyanate, cyclohexane-1,4-diisocyanate, ethylene diisocyanate, Trimethylhexamethylene diisocyanate, 1,4-diiso cyanatobutane, 1,12-diisocyanatododecane and dimer fatty acid diisocyanate, tetra methylene, hexamethylene, undecane, dodecamethylene, 2,2,4-trimethylhexane, 1,3-cyclohexane, 1, 4-cyclohexane, 4,4-dicyclohexylmethane and lysine ester diisocyanate, phenyl isoc yanate, 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, xylylene diisocyanate (XDI), tetramethylxylylene diisocyanate (TMXDI), 4,4'-diphenyldimethylmethane diisocyanate, di- and tetraalkyldiphenylmethane diisocyanate, 4,4'-dibenzene -Phenylene diisocyanate, 1,4-phenylene diisocyanate, the isomers of tolylene diisocyanate (TDI), the technical isomer mixture of 2,4- and 2,6-tolylene diisocyanate, 1,4-tetramethylxylene diisocyanate. 5. A compound according to claim 2, characterized in that the polyu rethane backbone contains 0.1 to 20 wt .-% free isocyanate groups. 6. A compound according to claim 2, characterized in that the polyu rethane backbone has an average molecular weight of 500 to 30,000. 7. A compound according to any one of claims 1 to 6, characterized in that the organic compound containing free isocyanate groups carries an ionic group which is selected from -COO ^- and protonated amines with cation formation. 8. Connection according to any one of claims 1 to 7, characterized in net that the fragrant alcohol R'OH is selected from the group consisting of A methyl alcohol, 2-hexyl alcohol, hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, Decyl alcohol, undecyl alcohol, lauryl alcohol, myristic alcohol, 3-methyl-but-2-en-1-ol, 3-methyl-1-pentanol, cis-3-hexenol, cis-4-hexenol, 3,5,5-trimethylhexanol, 3,4,5,6,6-pentamethylheptan-2-ol, citronellol, geraniol, oct-1-en-3-ol, 2,5,7-tri methyloctan-3-ol, 2-cis-3,7-dimethyl-2,6-octadien-1-ol, 6-ethyl-3-methyl-5-octen-1- ol, 3,7-dimethyl-oct-3,6-dienol, 3,7-dimethyloctanol, 7-methoxy-3,7-dimethyl-octane 2-ol, cis-6-nonenol, 5-ethyl-2-nonanol, 6,8-dimethyl-2-nonanol, 2,2,8-trimethyl-7 (8) - nonen-3-ol, nona-2,6-dien-1-ol, 4-methyl-3-decen-5-ol, 5-dec-9-en-1-ol, benzyl alcohol,  2-methyl-undecanol, 10-undecen-1-ol, 1-phenylethanol, 2-phenylethanol, 2- Methyl-3-phenyl-3-propenol, 2-phenylpropanol, 3-phenylpropanol, 4-phenyl-2-bu tanol, 2-methyl-5-phenylpentanol, 2-methyl-4-phenylpentanol, 3-methyl-5-phenyl pentanol, 2- (2-methylphenyl) ethanol, 4- (1-methylethyl) benzylmethanol, 4- (4-hydro xyphenyl) butan-2-one, 2-phenoxyethanol, 4- (1-methylethyl) -2-hydroxy-1-methylben zole, 2-methoxy-4-methylphenol, 4-methylphenol, anise alcohol, p-toluyl alcohol, cinnamon alcohol, vanillin, ethylvanillin, eugenol, isoeugenol, thymol, anethole, decahydro-2 naphthalenol, borneol, cedrenol, farnesol, fenchyl alcohol, menthol, 3,7,11-tri methyl-2,6,10-dodecatrien-1-ol, α-ionol, tetrahydroionol, 2- (1,1-dimethylethyl) -cyc lohexanol, 3- (1,1-dimethylethyl) cyclohexanol, 4- (1,1-dimethylethyl) cyclohexanol, 4-isopropyl cyclohexanol, 6,6-dimethyl-bicyclo [3.3.1] hept-2-en-2-ethanol, 6,6-di methyl-bicyclo [3.1.1] hept-2-en-methanol, p-menth-8-en-3-ol, 3,3,5-trimethylcyclo hexanol, 2,4,6-trimethyl-3-cyclohexenylmethanol, 4- (1-methylethyl) cyclo-hexyl methanol, 4- (1,1-dimethylethyl) cyclohexanol, 2- (1,1-dimethylethyl) cyclohexanol, 2,2,6-trimethyl-α-propylcyclohexane propanol, 5- (2,2,3-trimethyl-3-cyclopentenyl) -3- methylpentan-2-ol, 3-methyl-5- (2,2,3-trimethylcyclopent-3-enyl) pent-4-en-2-ol, 2- Ethyl 4- (2,2,3-trimethylcyclopentyl-3-enyl) but-2-en-1-ol, 4- (5,5,6-trimethylbi cyclo [2.2.1] hept-2-yl) cyclohexanol, 2- (2-methylpropyl) -4-hydroxy-4-methyl-tetra hydropyran, 2-cyclohexylpropanol, 2- (1,1-dimethylethyl) -4-methylcyclohexanol, 1- (2-tert-Butyl-cyclohexyloxy) -2-butanol, 1- (4-isopropyl-cyclohexyl) ethanol. 9. A method of making the compound according to any of the claims 1 to 8 contain by reaction of at least one free isocyanate group tendency organic compound with a scent alcohol R'OH under usual conditions conditions for the formation of a urethane in substance or solution. 10. The method according to claim 9, characterized in that the free isocya organic compound containing nat groups is selected from the group consisting of mono-, di- and triisocyanates and polyurethane frameworks. 11. The method according to claim 9 or 10 for the preparation of a compound of the formula

R [-NH-C (= O) -OR '] _n
where n = 1, 2 or 3 and R is derived from aliphatic, alicyclic or aromatic mono-, di- or triisocyanates having 1 to 30 carbon atoms. 12. The method according to claim 11, characterized in that the mono-, di- and triisocyanates are selected from the group consisting of 1-hexane isocyanate, 1-heptane isocyanate, 1-octane isocyanate, 1-non-isocyanate, 1-decane isocyanate, 1-undecane isocyanate , 10-undecene-1-isocyanate, 1-dodecane isocyanate, 1-tridecane isocyanate, 1-tetradecane isocyanate, 1-pentadecane isocyanate, 1-hexadecane isocyanate, 1-heptadecane isocyanate, 1-octadecane isocyanate, 9-cis-octadecene 1-isocyanate, 9- trans-octadecene-1-isocyanate, 9-cis-octadecene-1,12-diisocyanate, all-cis-9,12,15-octa-decadiene-1-isocyanate, all-cis-9, 12,15-octadecatriene- 1-isocyanate, 1-nonadecaniso cyanate, 1-eicosan isocyanate, 9-cis-eicosen-1-isocyanate, 5, 8, 11, 14-eicosatetraen-1-isocyanate, 1-heneicosan isocyanate, 1-docosan isocyanate, 13-cis-docosen -1-isocyanate, 13-trans-docosen-1-isocyanate, hydrogenated MDI (H ₁₂ MDI, a cycloaliphatic compound), 1-methyl-2,4-diisocyanato-cyclohexane, 1,6-diisocyanato-2,2, 4-tri methylhexane, 1,6-diisocyanato-2,4,4-trimethylhex an, 1-isocyanatomethyl-3-isocyanate-1,5,5-trimethyl-cyclohexane (isophorone diisocyanate = IPDI), butane-1,4-diisocyanate, hexamethylene diisocyanate (HDI), dicyclohexylmethane diisocyanate, cyclohexane-1,4-diisocyanate, Ethylene diisocyanate, trimethylhexamethylene diisocyanate, 1,4-diisocyanate anobutane, 1,12-diisocyanatododecane and dimer fatty acid diisocyanate, tetra methylene, hexamethylene, undecane, dodecamethylene, 2,2,4-trimethylhexane, 1,3-cyclohexane, 1,4-cyclohexane, 4,4-dicyclohexylmethane and lysine ester diisocyanate, phenyl isocyanate, 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, xylylene diisocyanate (XDI), tetramethylxylylene diisocyanate (TMXDI), 4,4'-diphe nyldimethylmethane diisocyanate, di- and tetraalkyldiphenylmethane diisocyanate, 4,4'-dibenzyl diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, the isomers of tolylene diisocyanate (TDI), the technical isomer mixture of 2,4- and 2,6- Tolylene diisocyanate, 1,4-tetramethylxylene diisocyanate. 13. The method according to claim 10, characterized in that the polyu rethane backbone contains 0.1 to 30 wt .-% free isocyanate groups. 14. The method according to claim 10, characterized in that the polyu rethane backbone has an average molecular weight of 500 to 30,000. 15. The method according to any one of claims 9 to 14, characterized in that the organic compound containing free isocyanate groups carries an ionic group which is selected from -COO ^- and protonated amines with cation formation. 16. The method according to any one of claims 9 to 15, characterized in net that the fragrant alcohol R'OH is selected from the group consisting of A methyl alcohol, 2-hexyl alcohol, hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, Decyl alcohol, undecyl alcohol, lauryl alcohol, myristic alcohol, 3-methyl-but-2-en-1-ol, 3-methyl-1-pentanol, cis-3-hexenol, cis-4-hexenol, 3,5,5-trimethylhexanol, 3,4,5,6,6-pentamethylheptan-2-ol, citronellol, geraniol, oct-1-en-3-ol, 2,5,7-tri methyloctan-3-ol, 2-cis-3,7-dimethyl-2,6-octadien-1-ol, 6-ethyl-3-methyl-5-octen-1- ol, 3,7-dimethyl-oct-3,6-dienol, 3,7-dimethyloctanol, 7-methoxy-3,7-dimethyl-octane 2-ol, cis-6-nonenol, 5-ethyl-2-nonanol, 6,8-dimethyl-2-nonanol, 2,2,8-trimethyl-7 (8) - nonen-3-ol, nona-2,6-dien-1-ol, 4-methyl-3-decen-5-ol, 5-dec-9-en-1-ol, benzylal alcohol, 2-methyl-undecanol, 10-undecen-1-ol, 1-phenylethanol, 2-phenylethanol, 2- Methyl 3-phenyl-3-propenol, 2-phenylpropanol, 3-phenylpropanol, 4-phenyl-2-buta nol, 2-methyl-5-phenylpentanol, 2-methyl-4-phenylpentanol, 3-methyl-5-phenylpen tanol, 2- (2-methylphenyl) ethanol, 4- (1-methylethyl) benzylmethanol, 4- (4-hydro xyphenyl) butan-2-one, 2-phenoxyethanol, 4- (1-methylethyl) -2-hydroxy-1-methylben zol, 2-methoxy-4-methylphenol, 4-methylphenol, anise alcohol, p-toluyl alcohol, cinnamon alcohol, vanillin, ethylvanillin, eugenol, isoeugenol, thymol, anethole, decahydro-2 naphthalenol, borneol, cedrenol, farnesol, fenchyl alcohol, menthol, 3,7,11- Trimethyl-2,6,10-dodecatrien-1-ol, α-ionol, tetrahydroionol, 2- (1,1-dimethylethyl) - cyclohexanol, 3- (1,1-dimethylethyl) cyclohexanol, 4- (1,1-dimethylethyl) -  cyclohexanol, 4-isopropyl cyclohexanol, 6,6-dimethyl-bicyclo [3.3.1] hept-2-en-2- ethanol, 6,6-dimethyl-bicyclo [3.1.1] hept-2-en-methanolp-menth-8-en-3-ol, 3,3,5-tri methylcyclohexanol, 2,4,6-trimethyl-3-cyclohexenylmethanol, 4- (1-methyl ethyl) cyclohexylmethanol, 4- (1,1-dimethylethyl) cyclohexanol, 2- (1,1-dimethylethyl) - cyclohexanol, 2,2,6-trimethyl-α-propyl cyclohexane propanol, 5- (2,2,3-trimethyl-3- cyclopentenyl) -3-methylpentan-2-ol, 3-methyl-5- (2,2,3-trimethylcyclopent-3- enyl) pent-4-en-2-ol, 2-ethyl-4- (2,2,3-trimethylcyclopentyl-3-enyl) but-2-en-1-ol, 4- (5,5,6-trimethylbicyclo [2.2.1] hept-2-yl) cyclohexanol, 2- (2-methylpropyi) -4-hydroxy- 4-methyl-tetrahydropyran, 2-cyclohexylpropanol, 2- (1,1-dimethylethyl) -4-methyl cyclohexanol, 1- (2-tert-butyl-cyclohexyloxy) -2-butanol, 1- (4-isopropyl-cyclohexyl) - ethanol. 17. Use of the compound as defined in any of claims 1 to 8 as an odor-forming additive to compositions selected from Paints, plastics, adhesives, cosmetics, cleaning agents, detergents, Hand dishwashing detergents, dishwashing detergents for automatic dishwashers and fabric softeners. 18. Use according to claim 17, characterized in that the additive 0.1 to 10 wt .-%, based on the composition. 19. A composition comprising the compound as in any of the claims sayings 1 to 8 defined. 20. Cosmetic composition according to claim 19, characterized in net that they 0.1 to 10 wt .-% of at least one of the compounds as in any nem of claims 1 to 8 defined, based on the total composition, contains. 21. Cosmetic composition according to claims 19 or 20, characterized ge indicates that it is selected from creams, shampoos, soaps, ointments, pu the, aerosols, deodorants.   22. Detergent composition according to claim 19, characterized records that it 0.1 to 10 wt .-% of at least one of the compounds as in ir defined according to one of claims 1 to 8, based on the total composition tongue, contains. 23. Detergent composition according to claim 19, characterized in net that they 0.1 to 10 wt .-% of at least one of the compounds as in any nem of claims 1 to 8 defined, based on the total composition, contains. 24. Hand detergent composition according to claim 19, characterized records that it 0.1 to 10 wt .-% of at least one of the compounds as in ir defined according to one of claims 1 to 8, based on the total composition tongue, contains. 25. Dishwashing detergent composition for automatic dishwashers according to claim 19, characterized in that they contain 0.1 to 10 wt .-% of at least one of the verbin endings as defined in any of claims 1 to 8 based on the Ge velvet composition, contains. 26. Fabric softener composition according to claim 19, characterized in that that they contain 0.1 to 10% by weight of at least one of the compounds as in any of claims 1 to 8, based on the total composition. 27. The adhesive composition of claim 19 comprising the compound as defined in any of claims 1 to 8. 28. A plastic composition according to claim 19 comprising the compound as defined in any of claims 1 to 8.   29. A coating composition according to claim 19 comprising the compound as in any of claims 1 to 8.