Orthoformic acid esters as pro-fragrances

Patent metadata

Field	Value
Publication number	US-9981937-B2
Application number	US-201515539338-A
Country	US
Kind code	B2
Filing date	Dec 8, 2015
Priority date	Dec 17, 2014
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

The disclosure relates to special orthoformic acid esters of formula (I), as defined herein, which can be used as thermally labile and acid-labile fragrance storage substances. The disclosure further relates to detergents and cleaning agents, cosmetic agents and air freshening products containing such orthoformic acid esters, as well as to a method for lastingly fragrancing surfaces.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
R 1 and R 2 are each independently of one another selected from the group of:
a linear, aliphatic, olefinic or open-chain organic residue having 2 to 20 carbon atoms and 0 to 10 heteroatoms selected from N, O, S and Si;
a branched or cyclic organic residue having 3 to 20 carbon atoms and 0 to 10 heteroatoms selected from N, O, S and Si; and
an aromatic or heteroaromatic organic residue having 4 to 20 carbon atoms and 0 to 10 heteroatoms selected from N, O, S and Si,
wherein R 2 is a residue derived from a fragrance alkene.

2. The compound according to claim 1 , wherein R 1 and R 2 are independently selected from the group of:
substituted or unsubstituted, linear or branched alkyl, alkenyl or alkynyl having up to 20 carbon atoms;
substituted or unsubstituted, linear or branched heteroalkyl, heteroalkenyl or heteroalkynyl having up to 20 carbon atoms, and 1 to 6 heteroatoms selected from O, S and N;
substituted or unsubstituted aryl having up to 20 carbon atoms;
substituted or unsubstituted heteroaryl having up to 20 carbon atoms, and 1 to 6 heteroatoms selected from O, S and N;
cycloalkyl or cycloalkenyl having up to 20 carbon atoms; and
heterocycloalkyl or heterocycloalkenyl having up to 20 carbon atoms, and 1 to 6 heteroatoms selected from O, S and N.

3. The compound according to claim 1 , wherein R 1 is
a. a residue of formula —C(O)—R 3 , —CH 2 —C(O)—R 3 , -aryl, -heteroaryl, —CH 2 -aryl or —CH 2 -heteroaryl, wherein R 3 is selected from the group of:
hydrogen, substituted or unsubstituted, linear or branched alkyl, alkenyl or alkynyl having up to 20 carbon atoms,
substituted or unsubstituted, linear or branched heteroalkyl, heteroalkenyl or heteroalkynyl having up to 20 carbon atoms, and 1 to 6 heteroatoms selected from O, S and N,
substituted or unsubstituted aryl having up to 20 carbon atoms,
substituted or unsubstituted heteroaryl having up to 20 carbon atoms, and 1 to 6 heteroatoms selected from O, S and N, and
cycloalkyl or cycloalkenyl having up to 20 carbon atoms, and heterocycloalkyl or heterocycloalkenyl having up to 20 carbon atoms, and 1 to 6 heteroatoms selected from O, S and N;

b. a residue of formula —C(O)—R 3 , wherein R 3 is a substituted or unsubstituted, linear or branched alkyl having up to 5 carbon atoms; or
c. a substituted or unsubstituted, linear or branched alkyl having 1 to 5 carbon atoms.

4. The compound according to claim 1 , wherein R 2
a. is an organic residue having 4 to 10 carbon atoms; and/or
b. comprises at least one heteroatoms selected from N, O, S, Si, F, Cl and Br; and/or
c. comprises at least one cyclic group; and/or
d. comprises at least one carbonyl group (—C(═O)—; and/or is a residue of formula C 1-10 -alkyl-O—(CH 2 ) p —C(O)O—(CH 2 ) q —, wherein p and q independently are 0 or an integer from 1 to 6.

5. The compound according to claim 1 , wherein R 1 is a fragrance alcohol, and wherein the fragrance alkene of R 2 and the fragrance alcohol of R 1 are selected from the group consisting of acetovanillone, allyl amyl glycolate, allyl isoamyl glycolate, alpha-amyl cinnamyl alcohol, anisyl alcohol, benzoin, benzyl alcohol, benzyl salicylate, 1-butanol, butyl lactate, 2-t-butyl-5-methylphenol, 2-t-butyl-6-methylphenol, carvacrol, carveol, 4-carvomenthenol, cedrol, cetyl alcohol, cinnamic alcohol, citronellol, o-cresol, m-cresol, p-cresol, crotyl alcohol, decahydro-2-naphthol, 1-decanol, 1-decen-3-ol, 9-decen-1-ol, diethyl malate, diethyl tartrate, dihydrocarveol, dihydromyrcenol, 2,6-dii sopropylphenol, dimethicone copolyol, 2,6-dimethoxyphenol, 1,1-dimethoxy-3,7-dimethyloctan-7-ol, 2,6-dimethyl-4-heptanol, 2,6-dimethylheptan-2-ol, 6,8-dimethyl-2-nonanol, 3,7-dimethyl-2,6-octadien-1-ol, 3,7-dimethyl-1,6-octadien-3-ol, 3,7-dimethyl-1-octanol, 3,7-dimethyl-3-octanol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-7-octen-1-ol, dimetol, 2-ethylfenchol, 4-ethylguaiacol, 2-ethyl-1-hexanol, ethyl 2-hydroxybenzoate, ethyl 3-hydroxybutyrate, 3-ethyl-2-hydroxy-2-cyclopenten-1-one, ethyl 2-hydroxycaproate, ethyl 3-hydroxyhexanoate, ethyl lactate, ethyl maltol, p-ethylphenol, ethyl salicylate, eugenol, farnesol, fenchyl alcohol, geraniol, glucose pentaacetate, glycerol, glyceryl monostearate, guaiacol, 1-heptanol, 2-heptanol, 3-heptanol, cis-4-heptenol, cis-3-heptenol, n-hexanol, 2-hexanol, 3-hexanol, cis-2-hexenol, cis-3-hexenol, trans-3-hexenol, 4-hexenol, cis-3-hexenyl hydrocinnamyl alcohol, 2-hydroxybenzoate, 2-hydroxyacetophenone, 4-hydroxybenzyl alcohol, 3-hydroxy-2-butanone, hydroxycitronellal, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone, 2-hydroxy-3-methyl-2-cyclopenten-1-one, 4-(p-hydroxyphenyl)-2-butanone, 2-hydroxy-3,5,5-trimethyl-2-cyclohexenone, delta-isoascorbic acid, isoborneol, isoeugenol, isophytol, isopropyl alcohol, p-isopropyl benzyl alcohol, 4-isopropylcyclohexanol, 3-isopropylphenol, 4-isopropylphenol, 2-isopropylphenol, isopulegol, lauryl alcohol, linalool, maltol, menthol, 4-methoxybenzyl alcohol, 2-methoxy-4-methylphenol, 2-methoxy-4-propylphenol, 2-methoxy-4-vinylphenol, α-methylbenzyl alcohol, 2-methylbutanol, 3-methyl-2-butanol, 3-methyl-2-buten-1-ol, 2-methyl-3-buten-2-ol, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, 4-methyl-2,6-dimethoxyphenol, methyl N-3,7-dimethyl-7-hydroxyoctylideneanthranilate, methyl 3-hydroxyhexanoate, 6-methyl-5-hepten-2-ol, 2-methylpentanol, 3-methyl-3-pentanol, 2-methyl-4-phenylbutan-2-ol, 2-methyl-3-phenylpropan-2-ol, methyl salicylate, 3-methyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-2-vinyl-5-(1-hydroxy-1-methylethyl)-3,4-dihydrofuran, myrtenol, neohesperidin dihydrochalcone, neomenthol, nerol, nerolidol, trans-2-cis-6-nonadienol, 1,3-nonanediol acetate, nonadyl, 2-nonanol, cis-6-nonen-1-ol, trans-2-nonen-1-ol, nonyl alcohol, 1-octanol, 2-octanol, 3-octanol, cis-3-octen-1-ol, cis-2-octen-1-ol, trans-2-octen-1-ol, cis-6-octen-1-ol, cis-octen-1-ol, 1-octen-3-ol, oleyl alcohol, patchouli alcohol, 3-pentanol, n-pentanol, 2-pentanol, 1-penten-1-ol, cis-2-penten-1-ol, perillyl alcohol, 2-phenoxyethanol arabinogalactan, beta-phenethyl alcohol, phenethyl salicylate, phenol, phenylacetaldehyde glyceryl acetal, 3-phenyl-1-pentanol, 5-phenyl-1-pentanol, 1-phenyl-1-pentanol, 1-phenyl-2-pentanol, 1-phenyl-3-methyl-1-pentanol, phytol, pinacol, polyalkylene glycol, Polysorbate 20, , Polysorbate 60, Polysorbate 80, , prenol, n-propanol, propenyl guaethol, propylene glycol, 2-propylphenol, 4-propylphenol, resorcinol, retinol, salicylaldehyde, sorbitan monostearate, sorbitol, stearyl alcohol, syringaldehyde, α-terpineol, tetrahydrogeraniol, tetrahydrolinalool, tetrahydromyrcenol, thymol, triethyl citrate, 1,2,6-trihydroxyhexane, p-alpha, alpha-trimethylbenzyl alcohol, 2-(5,5,6-trimethylbicyclo[2.2.1]hept-2-yl)cyclohexanol, 5-(2,2,3-trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol, 3,7,11-trimethyl-2,6,10-dodecatrien-1-ol, 3,7,11-trimethyl-1,6,10-dodecatrien-3-ol, 3,5,5-trimethyl-1-hexanol, 10-undecen-1-ol, undecyl alcohol, vanillin, o-vanillin, vanillyl butyl ether, 4-vinylphenol, 2,5-xylenol, 2,6-xylenol, 3,5-xylenol, 2,4-xylenol, xylose, 5-(2-methylpropyl)-1-methyl-1-cyclohexene, 1-methylidene-3-(2-methylpropyl)cyclohexane, and myrcene.

6. The compound according to claim 1 , wherein the compound is a compound of formula (II)

7. A detergent or cleaning agent comprising at least one compound of formula (I)

wherein
R 1 and R 2 are each independ

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Kropf Christian
• Gerke Thomas
• Huchel Ursula
• Mueller Thomas J J
• Papadopoulos Julian

Classifications

• C07C69/74

  Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring · CPC title

• C07C69/003

  Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom · CPC title

• C07D317/34 Primary

  Oxygen atoms · CPC title

• C11B9/0076

  the hetero rings containing less than six atoms · CPC title