US3884841A - 2-n-butyl 4,4,6-trimethyl-1,3 dioxane perfume - Google Patents
2-n-butyl 4,4,6-trimethyl-1,3 dioxane perfume Download PDFInfo
- Publication number
- US3884841A US3884841A US456317A US45631774A US3884841A US 3884841 A US3884841 A US 3884841A US 456317 A US456317 A US 456317A US 45631774 A US45631774 A US 45631774A US 3884841 A US3884841 A US 3884841A
- Authority
- US
- United States
- Prior art keywords
- weight
- parts
- trimethyl
- butyl
- perfume
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000002304 perfume Substances 0.000 title abstract description 16
- QUBNQDBPPTZYJL-UHFFFAOYSA-N 2-butyl-4,4,6-trimethyl-1,3-dioxane Chemical compound CCCCC1OC(C)CC(C)(C)O1 QUBNQDBPPTZYJL-UHFFFAOYSA-N 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- 241000195940 Bryophyta Species 0.000 description 2
- 244000178870 Lavandula angustifolia Species 0.000 description 2
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- -1 cyclic acetal Chemical class 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000001102 lavandula vera Substances 0.000 description 2
- 235000018219 lavender Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000011929 mousse Nutrition 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 description 1
- NFRFQWLJPHVZRK-UHFFFAOYSA-N 4,4,6-trimethyl-1,3-dioxane Chemical compound CC1CC(C)(C)OCO1 NFRFQWLJPHVZRK-UHFFFAOYSA-N 0.000 description 1
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Benzoesaeure-n-hexylester Natural products CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 235000002548 Cistus Nutrition 0.000 description 1
- 241000984090 Cistus Species 0.000 description 1
- 235000005241 Cistus ladanifer Nutrition 0.000 description 1
- 240000008772 Cistus ladanifer Species 0.000 description 1
- 240000007311 Commiphora myrrha Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 235000018958 Gardenia augusta Nutrition 0.000 description 1
- 239000004869 Labdanum Substances 0.000 description 1
- 244000147568 Laurus nobilis Species 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 241000219492 Quercus Species 0.000 description 1
- 241001128140 Reseda Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 244000284012 Vetiveria zizanioides Species 0.000 description 1
- 235000007769 Vetiveria zizanioides Nutrition 0.000 description 1
- 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 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 235000001053 badasse Nutrition 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000001299 ferula galbaniflua resinoid Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 244000056931 lavandin Species 0.000 description 1
- 235000009606 lavandin Nutrition 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000012437 perfumed product Substances 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Images
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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Definitions
- flavour Green "floral, peppermintlike
- Dependent on the type of composition the dosage 25 2j:n-Butyl-4.4.6-trimethyl-l.3- 160 parts by weight loxane may he between about 5 and about 15% by weight.
- mgthylpmhalme 103 parts by weight a matter of fact in a perfumed product the final concen- 1000 Pans by weight tration will lie much lower.
- 2-n-Butyl-4.4.6-trimethyl-1.3-dioxane may be prepared in the following way:
- the evaporation residue is fractionated in a distillation apparatus with a 40 cm Vigreus-head, at which is obtained: 4 g fore-runnings, boiling point up to 81C/l mm Hg and 170 g 2-n-butyl-4.4 .6-trimethyl-l .3- dioxane boiling point 8l-82C/1 mm Hg; u 1,4295.
- a perfume composition comprising from 5 to 16% of 2-n-butyl-4,4,6-trimethyl-1,3-dioxane in a perfume carrier.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Detergent Compositions (AREA)
Abstract
A process for the preparation of perfume compositions as well as perfumed articles.
Description
United States Patent Maessen et al.
[ 51 May 20, 1975 2-N-BUTYL 4,4,6-TRIMETHYL-l,3 DlOXANE PERFUME lnventors: Jan Th. M. F. Maessen; David DeRijke, both of Naarden, Netherlands Naarden International, N.V., Naarden-Bussum, Netherlands Filed: Mar. 29, 1974 Appl. No.: 456,317
Assignee:
Foreign Application Priority Data Apr. 18, 1973 Netherlands 7305487 U.S. Cl. 252/522 Int. Cl Cllb 7/00 Field of Search 252/5 22 [56] References Cited FOREIGN PATENTS OR APPLICATIONS 981,285 l/l965 United Kingdom 252/522 Primary Examiner-Veronica OKeefe Attorney, Agent, or Firm-Stevens, Davis, Miller & Mosher [57] ABSTRACT 1 Claim, 2 Drawing Figures 1 Z-n-BUTYL 4,4,6-TRIMETHYL-1,3 DIOXANE PERFUME 2-n-butyl-4.4.6-trimethyl*l.3-dioxane is the cyclic acetal derived from n-pentanal and 2-methylpentanediol-2.4. According to the literature (S.Arctander, Perq fume and Flavor Chemicals, Montelair, 1969) the following cyclic acetals of the general formula 2 are known as possible perfume of this diol:
It is clear that the abovementioned patent gives no positive expectation as to the perfume properties of 1.3-dioxanes having geminal methyl groups. In spite of that the applicants have prepared a series of pompounds of the general formula 2 and have them judged as to flavour and other usefulness in perfume composi R Description the flavour I Literature CH CH=CH- Floral green, almost herbaceous Arctander,
green, odor possibly to be used Monograph in perfume compositions as a 745.
modifier in modern. floral fragrance types of perfume Sweet-green, warm-earthy odor, id. CH2 reseda. To be used in combinat- Monograph ion with Oak-moss, Vetiver, 2485 Lavender and Rose materials warm floral with a fruity id. 2 2 note. As a fixative in Monogr'ph fruity-floral bases 2582.
such as Jasmin.
In addition to these descriptions in the literature (British Pat. No. 981,285) the following compounds of the general formula 2 are indicated, as being not suittions and perfumed articles by a panel of experienced perfumers. Their judgement has been summarized in the following table;
Description of the flavour Green, "floral, peppermintlike,
not interesting,
Green, herbaceous, fruity, not interesting.
soup-ggree'rslike not usuable Lavender, mint, bayleaflike, very interesting.
fatty, not int ere sting.
weak, little characteristic, not interesting.
weak, metallic, unuseful' Continued No. R Description of the flavour ..l.:- T i Y I p 8 li-- very weak rosellke, not useful.
-CH -OH weak, spicy, not lnterestlng The compounds 3 and 9 from the above tabel were Continued known already from the cited literature (S.Arctander) Camphor Chinese 2130 parts Ey wei l: as possibly interesting, but they appear not to be able figmjj i 508 5:2: by ifiifihi to stand the explicit evaluation by experienced perfu- Cedarwood oil Virginia 40 parts by weight mors. Surprisingly it appears, however, that compound 2121 5 522: ii; No.4,2-n-butyl-4,4.6-trimethyl-1.3-dioxane, in spite of 20 Liguvert" parts by weight the negative expectation aroused by the British patent Methylnonylfacemldehyde 3 Pans by welght Opoponax oil 1 parts by weight cited, to possess very attractive perfume properties. Tetrahydmlinalool 2 pans by weight Applied in perfume compositions 2-n-butyl-4.4.6- Cistus Oil 2 Parts y wqght Laurel noble oil 2 parts by weight trimethyl-l.3-dioxane gives a fresh, vegetable note to Myrrhe oil 2 pans by weight it. Dependent on the type of composition the dosage 25 2j:n-Butyl-4.4.6-trimethyl-l.3- 160 parts by weight loxane may he between about 5 and about 15% by weight. As mgthylpmhalme 103 parts by weight a matter of fact in a perfumed product the final concen- 1000 Pans by weight tration will lie much lower.
2-n-Butyl-4.4.6-trimethyl-1.3-dioxane may be prepared in the following way:
Into an 1 liter reaction receiver, provided with a agitator, Vigreux head having a tray trap and thermometer, are brought:
118 g (1 mol) of 2-methyl pentane diol-2.4.
86 g (1 mol) n-pentanal and 250 g of methylene chloride.
0,05 g p-toluene sulfonic acid is then added at about C under stirring. Subsequently in about 3 hours 18 g of water are removed by azeotropic distillation at a flask temperature of 57C. The contents of the flask are cooled and, after transfer into a separating funnel, washed with 100 g soda solution (5%) and thereafter with 100 g of water. Thereafter the organic solution is distilled under decreased pressure mm Hg) to a bottom temperature of 70C. There are obtained:
200 g of methylene chloride back and 180 g of evaporation residue.
The evaporation residue is fractionated in a distillation apparatus with a 40 cm Vigreus-head, at which is obtained: 4 g fore-runnings, boiling point up to 81C/l mm Hg and 170 g 2-n-butyl-4.4 .6-trimethyl-l .3- dioxane boiling point 8l-82C/1 mm Hg; u 1,4295.
The invention can be illustrated with the following examples:
Absolue Mousse de Chene Coumarine Musk R l Olibanum-resinoid 5 parts by weight 5 parts by weight 10 parts by weight 40 parts by weight (Liguvert a perfume base of Naarden lntemational) EXAMPLE II Perfume composition Lavender-Fougere for soap.
Absolue Labdanum dEspagne 5 Galbanum resinoid 5 parts by weight Coumarine l5 parts by weight Perpetual crist. 25 parts by weight Absolue Mousse de Chefie 20 parts by we ght- Hexylbenzoate 50 parts by we ght Benzylsalicylate 50 parts by weight Lavender oil 230 parts by weight Bergamot oil 150 parts by weight Petitgrain oil parts by weight Rosemary oil Spanish 50 parts by weight Geranium oil 50 parts by weight Vetiveryl acetate 50 parts by weight Patchouli oil 40 parts by weight Lavandin concrete 15 parts by weight Tetrahydrolinalool 10 parts by weight Eugenol 5 parts by weight 2-n-butyl-4.4.6-trimethyl-l.3- parts by weight dioxane 1000 parts by weight parts by weight The perfume compositions prepared according to the invention may be applied in a great variety of perfumed materials. Thus they may be applied e.g. in soaps, detergents, shampoos, toilet waters or in cosmetic preparations, such as shave lotions, sun creams, face creams and tallow powders.
We claim:
1. A perfume composition comprising from 5 to 16% of 2-n-butyl-4,4,6-trimethyl-1,3-dioxane in a perfume carrier.
Claims (1)
1. A PERFUME COMPOSITION COMPRISING FROM 5 TO 16% OF 2-N-BUTYL-4,4,6-TRIMETHYL-1,3-DIOXANE IN A PERFUME CARRIER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7305487.A NL166187C (en) | 1973-04-18 | 1973-04-18 | PROCESS FOR PREPARING PERFUME COMPOSITIONS BY MIXING A 2-SUBSTITUTED 4,4,6-TRIMETHYL-1,3-DIOXAN WITH AT LEAST ANY OTHER PERFUME AND PERFUMED ARTICLES. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3884841A true US3884841A (en) | 1975-05-20 |
Family
ID=19818679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US456317A Expired - Lifetime US3884841A (en) | 1973-04-18 | 1974-03-29 | 2-n-butyl 4,4,6-trimethyl-1,3 dioxane perfume |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3884841A (en) |
| JP (1) | JPS505541A (en) |
| BE (1) | BE812847A (en) |
| CH (1) | CH601470A5 (en) |
| DE (1) | DE2415922C3 (en) |
| FR (1) | FR2226187B1 (en) |
| GB (1) | GB1465320A (en) |
| IT (1) | IT1050471B (en) |
| NL (1) | NL166187C (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966647A (en) * | 1974-03-18 | 1976-06-29 | Lever Brothers Company | Perfume compositions containing monoalkyl-para-dioxanes |
| US4124541A (en) * | 1976-06-28 | 1978-11-07 | Henkel Kommanditgesellschaft Auf Aktien | Dioxa bicyclo dodecane and -hexadecane perfume compositions |
| US4146506A (en) * | 1976-10-23 | 1979-03-27 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Perfume compositions with 4-isopropyl-5,5-dimethyl-1,3-dioxane |
| US4198323A (en) * | 1977-07-29 | 1980-04-15 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | 2,2,5-Trimethyl-5-phenyl-1,3-dioxane and perfume compositions containing it |
| US4211674A (en) * | 1978-04-10 | 1980-07-08 | Polak's Frutal Works B.V. | Cyclic acetals and ketals and their use in perfume compositions |
| US4372880A (en) * | 1980-04-25 | 1983-02-08 | Henkel Kommanditgesellschaft Auf Aktien | Use of substituted 2-(1-methylbutyl)-1,3-dioxanes as perfuming agents |
| EP1316553A1 (en) * | 2001-11-30 | 2003-06-04 | Celanese Chemicals Europe GmbH | Fragrances based on cyclic acetals |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5939890A (en) * | 1982-08-26 | 1984-03-05 | Neos Co Ltd | Phenyl-substituted 2-(1-alkenyl)-4-isopropyl-5,5-dimethyl-1, 3-dioxane derivative |
| CN104066828B (en) * | 2012-01-18 | 2017-06-06 | 宝洁公司 | Perfume systems |
| CA2908686A1 (en) * | 2013-04-24 | 2014-10-30 | The Procter & Gamble Company | Perfume systems |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB981285A (en) * | 1962-09-04 | 1965-01-20 | Unilever Ltd | Alkylated 1,3-dioxanes and their use as perfumes |
-
1973
- 1973-04-18 NL NL7305487.A patent/NL166187C/en not_active IP Right Cessation
-
1974
- 1974-03-26 BE BE142464A patent/BE812847A/en not_active IP Right Cessation
- 1974-03-29 DE DE2415922A patent/DE2415922C3/en not_active Expired
- 1974-03-29 US US456317A patent/US3884841A/en not_active Expired - Lifetime
- 1974-04-05 GB GB1527274A patent/GB1465320A/en not_active Expired
- 1974-04-16 IT IT68215/74A patent/IT1050471B/en active
- 1974-04-16 JP JP49041789A patent/JPS505541A/ja active Pending
- 1974-04-16 FR FR7413186A patent/FR2226187B1/fr not_active Expired
- 1974-04-18 CH CH539274A patent/CH601470A5/xx not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB981285A (en) * | 1962-09-04 | 1965-01-20 | Unilever Ltd | Alkylated 1,3-dioxanes and their use as perfumes |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966647A (en) * | 1974-03-18 | 1976-06-29 | Lever Brothers Company | Perfume compositions containing monoalkyl-para-dioxanes |
| US4124541A (en) * | 1976-06-28 | 1978-11-07 | Henkel Kommanditgesellschaft Auf Aktien | Dioxa bicyclo dodecane and -hexadecane perfume compositions |
| US4146506A (en) * | 1976-10-23 | 1979-03-27 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Perfume compositions with 4-isopropyl-5,5-dimethyl-1,3-dioxane |
| US4198323A (en) * | 1977-07-29 | 1980-04-15 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | 2,2,5-Trimethyl-5-phenyl-1,3-dioxane and perfume compositions containing it |
| US4211674A (en) * | 1978-04-10 | 1980-07-08 | Polak's Frutal Works B.V. | Cyclic acetals and ketals and their use in perfume compositions |
| US4372880A (en) * | 1980-04-25 | 1983-02-08 | Henkel Kommanditgesellschaft Auf Aktien | Use of substituted 2-(1-methylbutyl)-1,3-dioxanes as perfuming agents |
| EP1316553A1 (en) * | 2001-11-30 | 2003-06-04 | Celanese Chemicals Europe GmbH | Fragrances based on cyclic acetals |
| EP1481974A1 (en) * | 2001-11-30 | 2004-12-01 | Celanese Chemicals Europe GmbH | Fragrances based on cyclic acetals |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1465320A (en) | 1977-02-23 |
| FR2226187B1 (en) | 1978-01-20 |
| NL166187C (en) | 1981-07-15 |
| NL7305487A (en) | 1974-10-22 |
| DE2415922A1 (en) | 1974-11-07 |
| DE2415922C3 (en) | 1978-06-08 |
| BE812847A (en) | 1974-09-26 |
| FR2226187A1 (en) | 1974-11-15 |
| NL166187B (en) | 1981-02-16 |
| IT1050471B (en) | 1981-03-10 |
| DE2415922B2 (en) | 1977-10-20 |
| JPS505541A (en) | 1975-01-21 |
| CH601470A5 (en) | 1978-07-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4033993A (en) | Cycloalkyl carbonates | |
| US3884841A (en) | 2-n-butyl 4,4,6-trimethyl-1,3 dioxane perfume | |
| EP2177598A1 (en) | Isomers of bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, ethyl ester and their use in perfume compositions | |
| CA2798047C (en) | Compounds with a woody note | |
| US20090163403A1 (en) | Novel Dioxaspiro Compounds and Their Use in Perfume Compositions | |
| EP0746552B1 (en) | Tetrahydrofurans and tetrahydropyrans | |
| US3948814A (en) | Acetaldehyde ethyl linalyl acetal perfume compositions | |
| US4190561A (en) | Esters of cyclohexene, odoriferous compositions containing said esters and process for the preparation thereof | |
| US4372880A (en) | Use of substituted 2-(1-methylbutyl)-1,3-dioxanes as perfuming agents | |
| US3660311A (en) | Novel fragrance methods and compositions | |
| US4302363A (en) | Perfume compositions containing 4(5)-acetyl-7,7,9(7,9,9)-trimethylbicyclo[4.]non-1-ene | |
| EP0276998B1 (en) | Perfumery materials | |
| US3647880A (en) | Novel fragrance materials and processes | |
| US7943559B2 (en) | Cyclopropanated macrocyclic ketones and lactones | |
| RU2562973C2 (en) | Novel bicyclic dioxanes, production and use thereof as aromatic compounds | |
| US10723971B2 (en) | Acetals of 1-(3,3-dimethylcyclohex-1-enyl) ethanone, method for the production thereof and use of same in perfumery | |
| US4124541A (en) | Dioxa bicyclo dodecane and -hexadecane perfume compositions | |
| US5175143A (en) | Perfumery materials | |
| US8178485B2 (en) | Hexahydro ethanochromenes and related compounds and their use in fragrance compositions | |
| US4317942A (en) | Odoriferous 2-alkoxyethyl-cycloalkyl-ethers | |
| US3915901A (en) | 2,6,10-Trimethyl-10-hydroxy-dodeca-2,6,11-trien-al as a perfuming agent | |
| EP1925607A1 (en) | Substituted hydrogenated naphthalene derivatives and their use in fragrance formulations | |
| EP1690848B1 (en) | Substituted 3-decene-5-one/ol derivatives | |
| US4404127A (en) | Perfume compositions and perfumed materials and articles, containing phenyl-tetrahydrofurans as a fragrance | |
| EP2977365B1 (en) | Novel cyclohexanols and their use in perfume composition |