Perfume compositions – Perfume compositions – Ring containing active ingredient
Reexamination Certificate
1999-07-23
2001-11-20
Warden, Jill (Department: 1721)
Perfume compositions
Perfume compositions
Ring containing active ingredient
C512S020000, C512S022000, C512S023000, C512S025000, C568S659000, C568S664000
Reexamination Certificate
active
06319889
ABSTRACT:
This invention relates to new chemical compounds useful as perfumes or as components of perfumes. More specifically it relates to ethers comprising a cycloalkyl moiety combined with either a phenylalkyl or a cyclohexylalkyl moiety.
There is a continuing search for materials having useful perfumery fragrance characteristics. These materials are sought either as replacements for naturally occurring compounds or as totally new scents or odour notes in their own right. For practicability reasons such materials should possess other favorable properties e.g. stability in applications and human and environmentally safety, all in addition to their useful odour notes.
It is the object of the present invention to provide a series of novel and practicable synthetic materials, being ethers comprising a cycloalkyl moiety combined with either a phenylalkyl or a cyclohexylalkyl moiety, and possessing very useful odours of the floral type. These novel ethers are represented by the generic formula I
wherein the cyclohexane moiety with the dotted circle represents either a cyclohexane ring or a benzene ring, n represents an integer with the value 1, 3, or 4, m represents an integer with the value 1 or 2, R
1
, R
2
, R
3
, R
4
and R
5
represent hydrogen or a lower alkyl group, and the total carbon number of R
1
, R
2
, R
3
, R
4
and R
5
combined is eight or less.
In the present context the term ‘lower alkyl’ indicates a straight or branched alkyl group of 1-6 carbon atoms.
It will be apparent that the novel ethers can exist in a variety of positional, stereoisomeric and enantiomeric forms and it is intended that these be included within the structural formulae.
According to a preferred embodiment n represents the value 1. More preferred is the situation wherein n and m both represent the value 1.
As indicated above the cyclohexane moiety with the dotted circle represents either a benzene ring or a saturated ring. In a preferred embodiment the cyclohexane moiety with the dotted circle is a benzene ring.
In the invention R
1
, R
2
, R
3
, R
4
and R
5
represent hydrogen or a lower alkyl, as defined herein. In a preferred embodiment R
1
, R
2
, R
3
, R
4
and R
5
, represent hydrogen. In an alternative embodiment R
1
and R
2
are each selected from hydrogen, methyl and ethyl, and R
3
, R
4
and R
5
are each selected from hydrogen and straight and branched alkyl groups comprising from 1 to 6 carbon atoms.
According to a specially preferred embodiment the compounds of the invention may be used in combination with a compound selected from the class of compounds having the structural formulae
wherein m represents an integer with the value 1 or 2 and R
2
, R
3
, R
4
and R
5
, represent hydrogen or a lower alkyl group,
and/or with a compound selected from the class of compounds having the structural formulae
wherein m represents an integer with the value 1 or 2 and R
2
, R
3
, R
4
and R
5
, represent hydrogen or a lower alkyl group, provided that the compounds of that mixture have the same definition for m, R
2
, R
3
, R
4
and R
5
.
Fragrance chemicals containing cycloalkyl, phenylalkyl or cyclohexylalkyl moieties are well known in perfumery. Many of them are subject of a monograph in “Perfume and Flavor Chemicals” by S. Arctander (published by the author, 1969). The major part of them belong to the chemical class of alcohols and the corresponding esters. One of the most widely used of all perfume chemicals is phenylethyl alcohol, mainly to impart a rosy odour effect. Also ethers of phenylethyl alcohol are known. Arctander describes respectively the methyl, ethyl, propyl, i-amyl, heptyl, benzyl, tetrahydropyranyl and vinyl ether of phenylethyl alcohol. C
3
and C
6
secondary alkyl and C
4
alkenyl ethers of phenylethyl alcohol are disclosed in the U.S. Pat. Nos. 4,328,206 and 4,357,319 and in European patent 49120. The 2-methyl-2-butenyl ether of phenylethyl alcohol is disclosed in French patent 2373276. Ethers of cyclohexyl alcohols and phenylethyl alcohols are described in the U.S. Pat. No. 4,306,096, 4,324,923, 4,335,008, 4,337,180, 4,343,791, 4,346,080, 4,350,733, 4,362,657, 4,371,715, 4,374,746 and in European patent 49120, Polyurethane foams containing ethers of cyclohexyl alcohols and phenylethyl alcohols are disclosed in U.S. Pat. 5,436,276 and British patent 2283750. Polymer compositions containing ethers of cyclohexyl alcohols and phenylethyl alcohols are disclosed in Canadian patent 2051469.
The novel ethers of the invention can be prepared by methods known in the art for analogous compounds. Overviews may be found in, inter alia, J. March, Advanced Organic Chemistry Reactions, Mechanisms, and Structure, 4
th
edition, J. Wiley & Sons, New York, 1992, Appendix C, Ethers, pp. 1285-1286, and R.C. Larock, Comprehensive Organic Transformations, A Guide to Functional Group Preparations, VCH Publishers, Inc., New York, 1998, Ethers, pp. 439-473. Of the many general methods known for ether formation, the preferred method for each compound may be different and will depend on considerations of economics, availability of starting materials, by-product formation, technical feasibility, safety, organoleptic grade produced, and the like, which parameters, circumstances and conditions may be subject to change over time, location, facility etc.
Generally preferred chemical methods in this context are dehydration of alcohols, addition of alcohols to alkenes and reaction between alkoxides and alkyl halides known to the art as Williamson synthesis. For the ethers of the invention the first two of these methods are especially preferred in terms of practicability and economics, i.e. the possibilities to avoid the use of solvents additional chemicals and waste streams, accessibility and economics of starting materials, simplicity of procedures, work up, purification, equipment, reaction conditions and the ease to arrive at organoleptically acceptable end products. It will be apparent that dehydration of two different alcohols may lead to three theoretically possible ethers, being the result of the combination of two identical alcohols and two different alcohols. Also, in the acid catalyzed addition of alcohols to alkenes, the dehydration of the alcohol involved can be a serious side reaction leading to the symmetrical ether from two identical alcohol molecules as a by-product. In the above referred to patent literature similar methods are described for ethers with a cyclohexyl and phenylethyl moiety. In the East German patent 289262 the two step preparation of mixed phenylethyl ethers from alcohols and phenyloxirane is disclosed. Ruthenium complex catalyzed addition of phenylethyl alcohol to alkenes is disclosed in J. Organomet. Chem (1995), 489 (1-2), 83-91.
The novel ethers of the invention exhibit a variety of useful odour nuances with natural green/ stemmy, leafy-floral and a honey-sweet character, reminiscent of hyacinth and sweet pea, unexpectedly out performing the ethers with phenylethyl moieties known to the art in terms of natural floralness, radiance and odour substantivity, which makes them specially suitable to be applied in fabric care, functional care and personal care consumer products. They can be used as fragrances per se or as components of a fragrance composition.
The invention is also directed to a “fragrance composition” or perfume composition comprising at least one compound according to the invention, preferably in combination with other olfactory active ingredients.
The term “fragrance composition” is used to denote a mixture of compounds including, for example, natural oils, synthetic oils, alcohols, aldehydes, ketone, esters, lactone, ethers, hydrocarbons, nitriles and other classes of chemical compounds which are admixed so that the combined odours of the individual components produce a pleasant or desired fragrance. Such fragrance compositions or the novel compounds of the invention alone can be used in conjunction with carriers, vehicles or solvents containing also as needed, dispersants, emulsifiers, surface-active agents, aerosols propellants odour release influencing
Johan van Manen Anton Pieter
Lenselink Willem
Cole Monique T.
Hoffmann & Baron , LLP
PFW Aroma Chemicals B.V.
Warden Jill
LandOfFree
Chemical compounds and perfume composition does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Chemical compounds and perfume composition, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chemical compounds and perfume composition will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2613135