US3745131A - Perfumery compositions - Google Patents
Perfumery compositions Download PDFInfo
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- US3745131A US3745131A US00808665A US3745131DA US3745131A US 3745131 A US3745131 A US 3745131A US 00808665 A US00808665 A US 00808665A US 3745131D A US3745131D A US 3745131DA US 3745131 A US3745131 A US 3745131A
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- US
- United States
- Prior art keywords
- longifolene
- perfumery
- composition
- hydroxymethyl
- derivatives
- Prior art date
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- 239000000203 mixture Substances 0.000 title abstract description 68
- ZPUKHRHPJKNORC-UHFFFAOYSA-N Longifolene Natural products CC1(C)CCCC2(C)C3CCC1(C3)C2=C ZPUKHRHPJKNORC-UHFFFAOYSA-N 0.000 abstract description 13
- PDSNLYSELAIEBU-UHFFFAOYSA-N Longifolene Chemical compound C1CCC(C)(C)C2C3CCC2C1(C)C3=C PDSNLYSELAIEBU-UHFFFAOYSA-N 0.000 abstract description 11
- 238000002156 mixing Methods 0.000 abstract description 7
- 239000000834 fixative Substances 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 230000002708 enhancing effect Effects 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 20
- 150000004192 longifolene derivatives Chemical class 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 239000012141 concentrate Substances 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 10
- 239000002304 perfume Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000001738 pogostemon cablin oil Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical class CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N KU0063794 Natural products CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 239000010627 cedar oil Substances 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- -1 hydroxymethyl compound Chemical class 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UAVFEMBKDRODDE-UHFFFAOYSA-N Vetiveryl acetate Chemical compound CC1CC(OC(C)=O)C=C(C)C2CC(=C(C)C)CC12 UAVFEMBKDRODDE-UHFFFAOYSA-N 0.000 description 3
- 229930002839 ionone Natural products 0.000 description 3
- 150000002499 ionone derivatives Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229940067107 phenylethyl alcohol Drugs 0.000 description 3
- 239000010671 sandalwood oil Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 239000010679 vetiver oil Substances 0.000 description 3
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 description 2
- NFAVNWJJYQAGNB-UHFFFAOYSA-N 2-methylundecanal Chemical compound CCCCCCCCCC(C)C=O NFAVNWJJYQAGNB-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000005792 Geraniol Substances 0.000 description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 238000010478 Prins reaction Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229940113087 geraniol Drugs 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- LQKRYVGRPXFFAV-UHFFFAOYSA-N Phenylmethylglycidic ester Chemical compound CCOC(=O)C1OC1(C)C1=CC=CC=C1 LQKRYVGRPXFFAV-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
Definitions
- composition according to claim 6 containing said longifolene derivative or derivatives in a concentration of from 0.1% to 20% by weight based on the total composition.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
W-HYDROXYMETHYL LONGIFOLENE AND/OR W-ACYLOXYMETHYL LONGIFOLENE WHEREIN THE ACYL GROUP HAS FROM 2 TO 4 CARBON ATOMS, PREFERABLY 2, MAY BE USED TO ADVANTAGE IN PERFUMERY COMPOSITIONS AS FIXATIVES, BLENDING AND ENHANCING AGENTS.
Description
nited States Patent 3,745,131 PERFUMERY COMPOSITIONS Anthony J. Curtis, Southsea, John F. Janes, Epping, Essex,
and Brian G. Jaggers, Romford, Essex, England, as-
signors to Bush Boake Allen Limited, London, England No Drawing. Filed Mar. 19, 1969, Ser. No. 808,665 Claims priority, application Great Britain, Mar. 21, 1968,
13,756/68; June 28, 1968, 31,033/68 Int. Cl. Cllb 9/00 U.S. Cl. 252-522 21 Claims ABSTRACT OF THE DISCLOSURE w-Hydroxymethyl longifolene and/or w-acyloxymethyl longifolenes wherein the acyl group has from 2 to 4 carbon atoms, preferably 2, may be used to advantage in perfumery compositions as fixatives, blending and enhancing agents.
This invention relates to perfumery compositions of the type Where a number of odoriferous materials, of synthetic or natural origin, are admixed to fonm a compounded perfumery concentrate.
Such concentrates may find use as such or after dilution, but more usually they are added in small proportions to other materials, such as to space sprays or to soap, detergent, cosmetic or deodorant compositions, or to substrates such as talc, fabrics, fibres or paper products, in order to provide them with agreeable olfactory properties. Thus such concentrates (as well as the aforesaid perfumed materials) are products of commerce and the perfumery concentrates may comprise a simple or complex mixture of individual perfumery compounds.
It is known that the sesquiterpene longifolene is obtained as a by-product in the refining of Indian oil of turpentine. It may also be obtained from other pine extracts. It has the structure (I). It has been proposed by Nagai et a1. (Chemical Abstracts 56, 1295 if (1962)) and by Nayak, Santhanakrishnan and Sukh Dev (Tetrahedron, 19, 2281-2292 (1963)) to react longifolene with formaldehyde in the presence of acetic acid according to the Prins reaction and thereby prepare 'w-acetoxymethyl longifolene (II) and therefrom w-hydroxymethyl longifolene (III). These authors do not, however, suggest that these compounds are other than chemical curiosities without commercial value.
CH-CHzOH longifolene w-acetoxymethyl w-hydroxymethyl longifolene longifolene (II) (III) We have now found that w-hydroxymethyl longifolene (III) and the lower w-acyloxymethyl longifolene derivatives, such as w-acetoxymethyl longifolene (II) are valuable ingredients of compounded perfumery concentrates and materials perfumed therewith. Firstly this is because in such concentrates and perfumed materials these compounds have the most surprising effect that this incorporation in some way makes the basic note of the perfume last longer, that is the compounds appear to have some fixative effect on the other more volatile perfumery ingredients of the composition and such other ingredients appear to be lost less rapidly from the composition. Secondly, these longifolene derivatives have the effect of blending together the individual oduors of the of the other perfumery ingredients of the composition resulting in the composition as a whole having a more harmonious perfume note and therefore a more im- "ice mediate impact on the connoisseur without the need to allow the composition to mature. This is an effect which we have not hitherto noted among perfumery chemicals. Thirdly, the presence of the longifolene derivative in some way enhances the top note quality of the composition causing the top note produced by some other ingredient to be more dominant in the overall composition.
Accordingly, the present invention provides a compounded perfumery composition which comprises an admixture of perfumery compounds including w-hydroxymethyl longifolene and/or an w-acyloxymethyl longifolene wherein the acyl group has from 2 to 4 carbon atoms.
These longifolene derivatives may be made by the process previously described or by other modifications of the Prins reaction. One particularly good method involves heating longifolene with a slight molar excess of paraformaldehyde in glacial acetic acid as solvent. A little of a strong protonising agent, such as sulphuric acid, zinc chloride or boron trifiuoride, may conveniently be added as catalyst. After removal of some of the excess acetic acid by distillation, the w-acetoxymethyl longifolene product may be isolated and purified by treatment with water to remove the remainder of the acid followed by extraction with a suitable solvent before final purifiaction by fractional distillation under vacuum. The w-hydroxymethyl longifolene may be made from the acetoxy derivative by hydrolysis with an alkali, particularly with potassium hydroxide in an aqueous ethanol solvent. It may be obtained as a solid by crystallisation from light petroleum. If desired some other acyloxymethyllongifolene derivatives may be made instead of the acetoxy derivative by use of the appropriate acid instead of acetic acid and the hydroxymethyl compound prepared therefrom by similar saponification.
The propionoxy-, butyroxyand iso-butyroxy-methyl longifolene derivatives have not hitherto been described and as new chemical compounds accordingly constitute a further aspect of the present invention.
Accordingly, the invention also provides longifolene derivatives of the general formula 5 on-cmocon where R is an alkyl group having two or three carbon atoms.
The w-hydroxymethyl longifolene and the abovedescribed acyl derivatives thereof have been found to be useful fixatives for a wide variety of common perfumery compounds in that in some way unknown they retard the loss thereof by volatilisation. This effect appears to be particularly marked in conjunction with Patchouli oil and with Vetivertype perfumery compounds, e.g. with Vetiveryl acetate, Vetiver oil, Cedar wood oil and, especially, Sandalwood oil. It is also manifested with ionone and/ or methylionone compounds and'with perfumery lactones,
particularly with 'y-nonalactone as well as with citronellyl esters, geraniol and phenyl ethyl alcohol.
Moreover, it has been found that when the w-hydroxymethyl longifolens or an acyl derivative thereof is used in association with a perfumery aldehyde, a more pronounced perfumery effect is obtained with the n-alkanals and methyl-n-alkanals having from 7 to 12 atoms; the effect with methyl nonyl acetadehyde is particularly noteworthy.
In use for the aforesaid purposes, the aforesaid longi- I folene derivatives will normally comprise from 0.1 to 10%, or even up to 20% by weight based on the total weight of perfumery ingredients in the compounded perfumery concentrate, but they are preferably employed in 37% of the concentrate on this basis. Moreover, the invention envisages the sale of a blend of an w-acyloxymethyl longifolene as specified with w-hydroxymethyl longifolene and/or with at least one other compound useful as an odoriferous ingredient of a compounded perfumery concentrate for use in the preparation of a more complex perfumery concentrate or perfumed material. The longifolene derivative(s) will normally comprise at least 50% by weight of such blends.
The compounded perfumery concentrates of the invention find use in a wide variety of perfumed materials. For example, the concentrates may find particular use in the formulation of coutourier-type perfumes, cologne or toilet waters, space sprays or they can be blended in soap, detergent or deodorant compositions including bath salts, shampoos, or in cosmetic preparations, such as face creams, talcum powders, body lotions, sun cream preparations and in male toilet products such as shave lotions and creams. The compositions can also be used to perfume substrates such as talc, fibres, fabric and paper products.
The following two preparations illustrate the production of the longifolene derivatives for use in the compounded perfumery concentrates of the invention, illustrative of which are those formulations set out in Examples 1-3.
PREPARATION I w-Acetoxy-methyl longifolene Longifolene (1,020 g.) and acetic acid (2,000 ml.) were placed with para-formaldehyde (365 g.) in a 5 litre flask and the mixture was refluxed at 110 C. for 20 hours. Excess acetic acid was distilled off and the crude acetate mixture washed with water (500 ml.), twice with a solution of sodium bicarbonate (500 ml.) and once with water (500 ml.). The resulting oil was dried over anhydrous sodium sulphate and distilled under reduced pressure to give the desired compound (about 500 g.) which could be purified by further distillation.
The novel compounds of the invention may be made by an analogous procedure employing in place of acetic acid, the appropriate propionic or butyric acid.
PREPARATION II w-Hydroxy-methyl longifolene Potassium hydroxide (168 g.) was dissolved in water (168 g.) and methyl alcohol (1,000 ml.). Approx. 350 grns. of the crude distilled w-acetoxymethyl longifolene obtained as in Preparation I was slowly added to the cold alkali solution and the mixture allowed to stand, overnight. The mixture was diluted with water and extracted with light petroleum (B.P. 100-120 C.). The combined extracts were filtered and the solution cooled to 50 C. The solid w-hydroxymethyl longifolene (approx. 195 g.) which then precipitated was then quickly filtered ofi.
EXAMPLE I Perfume with woody base Constituents of perfumery composition: Parts by weight Cedar wood oil (American) 400 Methyl ionone 100 Patchouli oil (Seychelles) 400 Vetiver oil (Bourbon) 100 Such a composition gives the odour effect of a mixture of the individual ingredients with the note of the cedar wood oil predominating. After application to a substrate the notes of different constituents predominate at different times.
The addition of 50 parts of w-hydroxymethyl longifolene had the effect of blending together the mixture and at the same time accentuated the Warm woody note of the Patchouli oil. This character was maintained throughout an extended dry out period.
On the other hand when 50 parts of w-acetoxymethyl longifolene was used instead, it blended the mixture similarly, but resulted in the typical root-like character of the Vetiver Oil as well as the note of the Patchouli Oil being accentuated. Again the total odour characteristics were maintained through an extended dry out period.
EXAMPLE III Perfume of sophisticated aldehyde base Constituents of perfumery composition: Parts by weight Undecylenic aldehyde 20 'y-Nonalactone 10 Methyl nonyl acetaldehyde 10 Hydroxycitronellal 50 Methyl ionone Pacthouli Oil (Seychelles) 50 Sandalwood Oil (East Indian) Vetiveryl acetate 500 It was found that the addition of 50 parts of either w-hydroxymethyl longifolene or w-acetoxymethyl longifolene caused a blending together of the various aldehydic notes which was otherwise achieved only after several months maturation of the composition. This effect was maintained throughout an extended dry out period as also was the overall character of the perfume.
EXAMPLE -III Perfume of simple floral (rose) type Constituents of perfumery composition: Parts by weight 10% solution of undecylenic aldehyde in phenyl ethyl alcohol 5 10% solution of ethylmethylphenyl glycidate Addition of '50 parts of either w-hydroxymethyl longifolene or w-acetoxymethyl longifolene had the effect of blending the above mixture into a composition with a smooth note of roses. At the same time its light fruity top note was accentuated. The fixative effect of the longifolene derivatives caused the composition to maintain its overall character over a long dry out period, whereas when the derivative was omitted the perfumery effect desired from the composition was lost after a short period of exposure on a substrate.
We claim:
1. A compounded erfumery composition containing at least one perfumery ingredient, and in addition to said perfumery ingredient, containing 0.1% to 50% by weight based on the total composition of at least one longifolene derivatives selected from the group consisting of w-hydroxymethyl longifolene and w-acyloxymethyl longifolenes wherein the acyl group has from 2 to 4 carbon atoms whereby said longifolene derivative has a fixing, blending and enhancing elfect on said perfumery composition.
2. A composition according to claim 1 which comprises at least one longifolene derivative selected from the group consisting of w-hydroxymethyl longifolene, and W-acetoxymethyl longifolene.
3. A composition according to claim 1 containing said longifolene derivative or derivatives in a concentration of from 0.1% to 20% by weight based on the total composition.
4. A composition according to claim 3 containing said longifolene derivative or derivatives in a concentration of from 0.1 to percent by weight based on the total composition.
5. A composition according to claim 4 containing said longifolene derivative or derivatives in a concentration of from 3 to 7 percent by weight based on the total composition.
6. A compounded perfumery composition containing an effective amount of at least one perfumery material selected fro-m the group consisting of Patchouli oil, Vetivertype perfumery compounds, ionone perfume compounds, methylionone perfume compounds, n-alkanal and methyl n-alkanal perfume compounds having from 7 to 12 carbon atoms, and perfumery lactones, and containing 0.1% to 50% by weight based on said compounded perfumery composition of at least one longifolene derivative selected from the group consisting of w-hydroxymethyl longifolene and w-acyloxymethyl longifolenes wherein the acyl group has from 2 to 4 carbon atoms whereby said longifolene derivative has a fixative effect on said perfumery composition.
7. A composition according to claim 6 containing said longifolene derivative or derivatives in a concentration of from 0.1% to 20% by weight based on the total composition.
8. A composition according to claim 7 containing said longifolene derivative or derivatives in a concentration of from 0.1 to 10 percent by weight based on the total composition.
9. A composition according to claim 8 containing said longifolene derivative or derivatives in a concentration of from 3 to 7 percent by weight based on the total composition.
10. A composition according to claim 8 wherein said perfumery material is Vetiveryl acetate.
11. A composition according to claim 8 wherein perfumery material is Vetiveryl oil.
12. A composition according to claim 8 wherein perfumery material is Patchouli oil.
13. A composition according to claim 8 wherein erfumery material is Cedar wood oil.
14. A composition according to claim 8 wherein perfumery material is Sandalwood oil.
15. A composition according to claim 8 wherein perfumery material is ionone.
16. A composition according to claim 8 wherein perfumery material is methylionone.
17. A composition according to claim 8 wherein perfumery material is 'y-nonalactone.
18. A composition according to claim 8 wherein perfumery material is citronellyl esters.
19. A composition according to claim 8 wherein perfumery material is geraniol.
20. A composition according to claim 8 wherein perfumery material is phenyl ethyl alcohol.
21. A composition according to claim 8 wherein perfumery material is methyl nonyl acetaldehyde.
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References Cited Chem. Abst. Subject Index, vol. 5665 (1962-1966), p. 131233.
SAM ROSEN, Primary Examiner
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1375668 | 1968-03-21 | ||
| GB3103368 | 1968-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3745131A true US3745131A (en) | 1973-07-10 |
Family
ID=26249981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00808665A Expired - Lifetime US3745131A (en) | 1968-03-21 | 1969-03-19 | Perfumery compositions |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3745131A (en) |
| CH (1) | CH512580A (en) |
| DE (1) | DE1913691A1 (en) |
| FR (1) | FR2004426A1 (en) |
| NL (1) | NL6904363A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3839233A (en) * | 1970-05-14 | 1974-10-01 | Int Flavors & Fragrances Inc | Perfume compositions |
| US4100110A (en) * | 1974-08-09 | 1978-07-11 | Bush Boake Allen Limited | Isolongifolene Prins reaction compounds in perfumery |
| US9399078B2 (en) | 2009-12-17 | 2016-07-26 | The Procter & Gamble Company | Unscented and low scented malodor control compositions and methods thereof |
| US11110196B2 (en) | 2013-08-01 | 2021-09-07 | The Procter & Gamble Company | Articles comprising malodor reduction compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2281100A1 (en) * | 1974-08-12 | 1976-03-05 | Bush Boake Allen Ltd | Perfume agents prepd. by reacting isolongifolene with aldehydes - using a Prins reaction catalyst |
-
1969
- 1969-03-18 DE DE19691913691 patent/DE1913691A1/en active Pending
- 1969-03-19 US US00808665A patent/US3745131A/en not_active Expired - Lifetime
- 1969-03-20 CH CH421769A patent/CH512580A/en not_active IP Right Cessation
- 1969-03-20 FR FR6908218A patent/FR2004426A1/fr not_active Withdrawn
- 1969-03-21 NL NL6904363A patent/NL6904363A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3839233A (en) * | 1970-05-14 | 1974-10-01 | Int Flavors & Fragrances Inc | Perfume compositions |
| US4100110A (en) * | 1974-08-09 | 1978-07-11 | Bush Boake Allen Limited | Isolongifolene Prins reaction compounds in perfumery |
| US9399078B2 (en) | 2009-12-17 | 2016-07-26 | The Procter & Gamble Company | Unscented and low scented malodor control compositions and methods thereof |
| US9642927B2 (en) | 2009-12-17 | 2017-05-09 | The Procter & Gamble Company | Unscented and low scented malodor control compositions and methods thereof |
| US11110196B2 (en) | 2013-08-01 | 2021-09-07 | The Procter & Gamble Company | Articles comprising malodor reduction compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1913691A1 (en) | 1969-11-06 |
| CH512580A (en) | 1971-09-15 |
| NL6904363A (en) | 1969-09-23 |
| FR2004426A1 (en) | 1969-11-21 |
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