US969636A - Perfume. - Google Patents
Perfume. Download PDFInfo
- Publication number
- US969636A US969636A US54138510A US1910541385A US969636A US 969636 A US969636 A US 969636A US 54138510 A US54138510 A US 54138510A US 1910541385 A US1910541385 A US 1910541385A US 969636 A US969636 A US 969636A
- Authority
- US
- United States
- Prior art keywords
- ortho
- phthalic acid
- perfume
- esters
- ester
- 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 description 13
- 150000002148 esters Chemical class 0.000 description 17
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 17
- 239000000126 substance Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 5
- 239000000341 volatile oil Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- JHGWQSGWUPCKNT-UHFFFAOYSA-N 2-tert-butyl-4-methyl-1,3,5-trinitrobenzene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(C(C)(C)C)=C1[N+]([O-])=O JHGWQSGWUPCKNT-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000501754 Astronotus ocellatus Species 0.000 description 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 241000208152 Geranium Species 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- 244000179970 Monarda didyma Species 0.000 description 1
- 235000010672 Monarda didyma Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- -1 methyl-ethyl Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
Definitions
- This invention has for its objectthe provision of improved perfume bases and also has for its object the manufacture of new and improved perfumes by the use of such new and improved bases.
- the base or solvent for theodoriferous and other substances used should have the following properties :It should be, colorless, odorless, have a very low :t reezing point, be nonpoisonous, non-irritant to the skin and only slowly Volatile but must have good solvent properties.
- :It should be, colorless, odorless, have a very low :t reezing point, be nonpoisonous, non-irritant to the skin and only slowly Volatile but must have good solvent properties.
- alcohol is used as the base or solvent in the n1a ority of perfumes manufactured.
- R, and R represent any alkyl radical such as methyl, ethyl, propyl, butyl,
- esters of isophthalic and terephthalic acids of-the formulae and G' HACOOHMfl-A may also be used for this purpose but are at resent of no practical importance.
- the neutral esters of ortho-phthalic acid such as I employ are colorless,practically odorless,-have a low freezing point, are not readily inflammable, do not irritate the skin and are non-poisonous. They are miscible with alcohol, ether, chloroform and glycerin in all proportions. They are excellent solvents of the various essential oils, balsains, synthetic compounds such as artificial musk, cumarin and other substances used in the manufacture of perfumery an l while themselves possessing the properties of blending the various odoriferous mate- 'rialsin a satisfactory manner are comparatively stable and Without chemical action on the substances dissolved. On account of their-high boiling points ranging between 275 and 325 degrees, they volatilize very slowly but finally completely without leaving any stain on fabrics.
- the odoriferou's material and the base volatilize Very slowly, the -base serving to prevent the too rapidly volatilization of the perfume although slowly and completely volatile.
- hat I claim is 1.
- the combination comprising an ester of ortho-phthalic acid and essential oils.
- 1 2.
- the combination comprising a neutral ester of ortho-phthalic acid and essential 01 s.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Description
UNITED sTAa ns sic CLEMENS OSCAR KLEBER, OF CLIFTOJTfhIEW JERSEY.
Patented Sept. 6, lei-e.
PERFUME.
969,636. Specification of Letters Patent. No Drawing.-
To all whom it may concern:
Be it known that I, CLnarnNs Osman K'Lnisnn, a citizen of Germany, residing at the village of Clifton, in the county of Passaic and Stateof New Jersey, have invented certain new and useful Improvements in Perfumes; and I do hereby declare the followingto be a full, clear, and exact descrip tion 'of the invention, such as will enable others skilled in the artto which .it appertains to make and use the same.
This invention has for its objectthe provision of improved perfume bases and also has for its object the manufacture of new and improved perfumes by the use of such new and improved bases.
In the manufacture of perfume'ry, the base or solvent for theodoriferous and other substances used should have the following properties :It should be, colorless, odorless, have a very low :t reezing point, be nonpoisonous, non-irritant to the skin and only slowly Volatile but must have good solvent properties. At present, as the base or solvent in the n1a ority of perfumes manufactured, alcohol is used.
It is apparent that not many substances respond to all of the above tests but I believe I have discovered a series of compounds which are suitable for this inafter described.
I have found by experiment that the esters of orthophthalic acid of the general formula coon, \cooa,
purpose as here- 1n which R, and R represent any alkyl radical such as methyl, ethyl, propyl, butyl,
.amyl, etc, or their isomers fulfil the above tests. It is of course, understood, that in stead of esters of ortho-phthalie' acid of the in which the same alkyl radical is resent in both 'carboxyl' groups are equa lysatisfznctory. In practice I have. found that as Application filed February 1, 1910, Serial ll'o. 541,3 85.
examples of such solvents or bases which are satisfactory, ell-ethyl esters of orth0- phthalic acid oooo n,
\COOC,H methyl-ethyl esters of ortho-phthalic acid C()OCH 6 \oooo,u, and dianethyl esters of ortho-phthalic acid /C()OCH \oooon,
but it will be apparent from the constitution of phthalic acid that a large number of esters of phthalic acid may beemployed for this purpose. The esters of isophthalic and terephthalic acids of-the formulae and G' HACOOHMfl-A) may also be used for this purpose but are at resent of no practical importance.
The neutral esters of ortho-phthalic acid such as I employ are colorless,practically odorless,-have a low freezing point, are not readily inflammable, do not irritate the skin and are non-poisonous. They are miscible with alcohol, ether, chloroform and glycerin in all proportions. They are excellent solvents of the various essential oils, balsains, synthetic compounds such as artificial musk, cumarin and other substances used in the manufacture of perfumery an l while themselves possessing the properties of blending the various odoriferous mate- 'rialsin a satisfactory manner are comparatively stable and Without chemical action on the substances dissolved. On account of their-high boiling points ranging between 275 and 325 degrees, they volatilize very slowly but finally completely without leaving any stain on fabrics.
As an example of a. perfume made with esters of orth'o hthalic acid, I take 95 parts of the di-n1ethy ester of ortho-phthalic acld and dissolve in same one part each of the following substances, oil of bergamot, oil of geranium, ionone, linalol and-tincture of musk, the whole comprising lOOparts. This combination will make a very strong pe ifume and it is evident that the foregoing formula represents only a single illustration of a perfume made with an ester of orthonphthalic acid as I do not Wish to be limited to'the'use of any specific erfumery substances or any specific proportion of same in the solution of the ester or esters of orthophthalic acid.
When used as perfume bases, the odoriferou's material and the base volatilize Very slowly, the -base serving to prevent the too rapidly volatilization of the perfume although slowly and completely volatile.
hat I claim is 1. The combination comprising an ester of ortho-phthalic acid and essential oils. 1 2. The combination comprising a neutral ester of ortho-phthalic acid and essential 01 s.
3. The combination of an ester of ortho; phthalic acid, essential oils and synthetic perfumes.
4. The combination of a neutral ester of ortho-phthalic acid, essential oils and synthetic perfumes.
5. The combination comprising an ester of ortho-phthalic acid and perfumery oils soluble therein.
(3. The combination comprising an ester of ortho-phthalic acid and odoi'iferous slightly olatile erfumery substances soluble therein.
In testimony whereof I atfix my signature in presence of two witnesses.
CLEMENS OSCAR KLEBER. lVitnesscs WALTER K11 SARA D. BOFFARD.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54138510A US969636A (en) | 1910-02-01 | 1910-02-01 | Perfume. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54138510A US969636A (en) | 1910-02-01 | 1910-02-01 | Perfume. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US969636A true US969636A (en) | 1910-09-06 |
Family
ID=3038026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US54138510A Expired - Lifetime US969636A (en) | 1910-02-01 | 1910-02-01 | Perfume. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US969636A (en) |
-
1910
- 1910-02-01 US US54138510A patent/US969636A/en not_active Expired - Lifetime
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