US2023769A - Fatty mixture capable of being emulsified - Google Patents
Fatty mixture capable of being emulsified Download PDFInfo
- Publication number
- US2023769A US2023769A US555142A US55514231A US2023769A US 2023769 A US2023769 A US 2023769A US 555142 A US555142 A US 555142A US 55514231 A US55514231 A US 55514231A US 2023769 A US2023769 A US 2023769A
- Authority
- US
- United States
- Prior art keywords
- emulsified
- water
- products
- unsaturated fatty
- esters
- 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
- 239000000203 mixture Substances 0.000 title description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 7
- 239000010698 whale oil Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- -1 alkali metal salt Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/08—Sulfation or sulfonation products of fats, oils, waxes, or higher fatty acids or esters thereof with monovalent alcohols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
- Y10S516/909—The agent contains organic compound containing sulfoxy*
Definitions
- Patented Dec. 10, 1935 FATTY IHIX'I'URE CAPABLE OF BEING EMULSIFIED Karl Ott, Leverkusen-on-tlie-Rhine, and Gustav Mauthe, Cologne-Holweide, Germany, assignors, by mesne assignments, to General Aniline Works, Inc., New York, N. Y.
- the present invention relates to a processof partially suli-lting unsaturated fatty acids and/or their esters or substances containing these fatty acids and/or esters thereof, and to the partially sulfited products thus obtainable.
- partially sulfitated products we mean the compounds which are obtainable by treating unsaturated fatty acids or their esters with an aqueous solution of sulfurous acid salts in an amount unsuflicient for the exhaustive sulfltation or by interrupting the sulfltation before exhaustive sulfltation has taken place while simultaneously reacting with oxidizing agents upon the unsaturated fatty acids or their esters with or without catalysts.
- This partial sulfltation can be achieved, for instance, by reacting upon one mol of an unsaturated fatty compound with less than a molecular quantity of a sulfltation agent, at elevated temperature, say at temperatures of between about and 100 C. for a prolonged time, say 10 to 30 hours and simultaneously passing oxygen or a gas containing oxygen, especially air, through the reaction mixture.
- a sulfltation agent for example, when the process is started with train oil one mol of a fatty acid group is used to about one third to two thirds of 9. mol of bisulfite.
- the process can also be carried out with molecular quantities or with an excess of the sulfltating agent, ut in this case the process is to be interrupte before the whole quantity of the sulfurous acid salts has reacted.
- the products obtainable by the processes described above are heterogeneous mixtures consisting apparently of some initial fatty acids and esters thereof and mainly of hydroxy-carboxylic acids !and their esters, polymerization products of the initial and the hydroxylated fatty acid substances and especially of sulfonic acids of all the said fatty acid materials.
- the new mixtures obtained according to the present invention are generally yellowish or brownish colored substances, possessing a valuable emulsifying capacity in weakly acid and alkaline reaction and are valuable stuf fing and reviving agents.
- valuable emulsions By stirring with hot water valuable emulsions are obtained the dispersing degree of which can be varied corresponding to the 5 use,-for instance, by a suitable proportion of sulfitating agents.
- Train oils which belong to the cheapest fats can be subjected best to the new process.
- These products can easily be brought intoa milky emulsion which is quickly o absorbed by the leather without further additions.
- the stufllng value is much higher than that of a train oil sulfonated in the usual manner. This property depends on the gentle treatment during the process which maintains the fatty 15 properties to a. high degree on one hand and the dispersing degree of the emulsions is particularly suitable for the stumng of leather on the other hand.
- ExampZe --100 parts of train 011 are mixed with 50-parts of an aqueous sodium blsulfite lye of 40 'B'. and then heated with air at to C. 25 while violently stirring until the solubility in water does no more increase. The duration depends on the kind of the apparatus, stirrer, the distributing degree of the air blown in.
- the reaction is mostly finished after 15 to 20 hours.
- a sample 80 of the oily product is then clearly soluble when diluted with water in a proportionof 1:1. After a further dilution with hot water a milky stable and weakly acid reacting emulsion is formed. Working up is not necessary.
- the reaction prodnot represents a valuable stufling agent for leather.
- parts of a neutralized, dyed chrome calf are in- 40 troduced into a drum containing 100 parts of water of 60 G. Then an emulsion of 3 parts of a sulfitated train oil prepared inaccordance with the example and 30 parts of water of 60 to 70 C. are entered through the hollow axis of the drum. 45 After about 30 to 45 minutes the fat has been completely absorbed. The skins are finished in the usual manner.
- unsaturated fatty acid cornpound as used in the appended claims we mean 50 to include unsaturated fatty acids per se and esters of such acids.
- a process for preparing mixtures capable of being emulsified in water which comprises heating a starting material containing an unsaturated compound selected from the group consisting of unsaturated fatty acids and their esters, as such, with an aqueous solution of about a molecular quantity of a sulfurous acid salt at a temperature between about C. and about 100 C. while simultaneously causing an oxidizing agent to react upon the starting material, the treatment being continued until the solubility of the reaction products in water no longer increases, whereby the starting material is partially sulfitated and converted into a product which forms a stable emulsion with water.
- yellowish to brownish mixtures consisting essentially of partially sulfitated unsaturated fatty acid compounds, said mixtures. being capable of being emulsified in water to form stable weakly acid to alkaline emulsions and adapted for use as stufiing and reviving agents, 5 said products being obtainable by heating a starting material containing an unsaturated fatty acid compound, as such, with an aqueous solution of about a molecular quantity of a sulfurous acid salt at a temperature between about 50 C. and 10 about 100 C. while simultaneously causing an oxidizing agent to react upon the starting material, the treatment being continued until the solubility of the reaction products in water no longer increases. l5 8.
- a yellowish to brownish mixture consisting essentially of partially sulfitated train oil, said mixture being capable of being emulsified in water to form a stable weakly acid to alkaline emulsion and adapted for use as 20 a stufiing and reviving agent, said mixture being obtainable by sulfitating one molecular proportion of train oil with about A; to mols of an aqueous solution of a sulfurous acid salt at from about to about C. while simultaneously 25 causing an oxidizing agent to react upon the starting material, the treatment being continued until the solubility of the reaction products in water no longer increases.
Description
Patented Dec. 10, 1935 FATTY IHIX'I'URE CAPABLE OF BEING EMULSIFIED Karl Ott, Leverkusen-on-tlie-Rhine, and Gustav Mauthe, Cologne-Holweide, Germany, assignors, by mesne assignments, to General Aniline Works, Inc., New York, N. Y.
No Drawing. Application August 4, 1931, Serial No. 555,142. In GermanyS eptember 18,1930
8 Claims. (Cl.8712) The present invention relates to a processof partially suli-lting unsaturated fatty acids and/or their esters or substances containing these fatty acids and/or esters thereof, and to the partially sulfited products thus obtainable.
By partially sulfitated products we mean the compounds which are obtainable by treating unsaturated fatty acids or their esters with an aqueous solution of sulfurous acid salts in an amount unsuflicient for the exhaustive sulfltation or by interrupting the sulfltation before exhaustive sulfltation has taken place while simultaneously reacting with oxidizing agents upon the unsaturated fatty acids or their esters with or without catalysts.
These products areobtainable by treating. an unsaturated fatty acid or an ester thereof with an aqueous solution of less than a molecular quantity of a sulfurous acid salt, such as sodium sulfite and sodium bisulfite and simultaneously causing oxidizing agents to take part in the reaction with. or without catalysts. As catalysts especially heavy metal compounds are used, for instance, the siccatives generally employed in the drying of oils, such as lead-naphthenate and the soaps of cobalt, manganese or zinc. This partial sulfltation can be achieved, for instance, by reacting upon one mol of an unsaturated fatty compound with less than a molecular quantity of a sulfltation agent, at elevated temperature, say at temperatures of between about and 100 C. for a prolonged time, say 10 to 30 hours and simultaneously passing oxygen or a gas containing oxygen, especially air, through the reaction mixture. For example, when the process is started with train oil one mol of a fatty acid group is used to about one third to two thirds of 9. mol of bisulfite.
It is to be understood that the process can also be carried out with molecular quantities or with an excess of the sulfltating agent, ut in this case the process is to be interrupte before the whole quantity of the sulfurous acid salts has reacted.
The products obtainable by the processes described above are heterogeneous mixtures consisting apparently of some initial fatty acids and esters thereof and mainly of hydroxy-carboxylic acids !and their esters, polymerization products of the initial and the hydroxylated fatty acid substances and especially of sulfonic acids of all the said fatty acid materials. I
The new mixtures obtained according to the present invention are generally yellowish or brownish colored substances, possessing a valuable emulsifying capacity in weakly acid and alkaline reaction and are valuable stuf fing and reviving agents. By stirring with hot water valuable emulsions are obtained the dispersing degree of which can be varied corresponding to the 5 use,-for instance, by a suitable proportion of sulfitating agents. Train oils which belong to the cheapest fats can be subjected best to the new process. These products can easily be brought intoa milky emulsion which is quickly o absorbed by the leather without further additions. The stufllng value is much higher than that of a train oil sulfonated in the usual manner. This property depends on the gentle treatment during the process which maintains the fatty 15 properties to a. high degree on one hand and the dispersing degree of the emulsions is particularly suitable for the stumng of leather on the other hand.
The following example serves to illustrate our an invention but without limiting it thereto. The parts are by weight.
ExampZe:--100 parts of train 011 are mixed with 50-parts of an aqueous sodium blsulfite lye of 40 'B'. and then heated with air at to C. 25 while violently stirring until the solubility in water does no more increase. The duration depends on the kind of the apparatus, stirrer, the distributing degree of the air blown in. The reaction is mostly finished after 15 to 20 hours. A sample 80 of the oily product is then clearly soluble when diluted with water in a proportionof 1:1. After a further dilution with hot water a milky stable and weakly acid reacting emulsion is formed. Working up is not necessary. The reaction prodnot represents a valuable stufling agent for leather.
The following illustrates a use of the product produced according to the above example: parts of a neutralized, dyed chrome calf are in- 40 troduced into a drum containing 100 parts of water of 60 G. Then an emulsion of 3 parts of a sulfitated train oil prepared inaccordance with the example and 30 parts of water of 60 to 70 C. are entered through the hollow axis of the drum. 45 After about 30 to 45 minutes the fat has been completely absorbed. The skins are finished in the usual manner.
By the expression unsaturated fatty acid cornpound as used in the appended claims we mean 50 to include unsaturated fatty acids per se and esters of such acids.
We claim:
1. The process for preparing mixtures capable of being emulsified in water comprising partially $5 sulfitating one molecular proportion of train oil with about ,4; to mols of aqueous sodium bisulflte of '40 B. at from about 60 to about 80 C. with simultaneous oxidation with air.
2. A process for preparing mixtures capable of being emulsified in water, which comprises heating a starting material containing an unsaturated compound selected from the group consisting of unsaturated fatty acids and their esters, as such, with an aqueous solution of about a molecular quantity of a sulfurous acid salt at a temperature between about C. and about 100 C. while simultaneously causing an oxidizing agent to react upon the starting material, the treatment being continued until the solubility of the reaction products in water no longer increases, whereby the starting material is partially sulfitated and converted into a product which forms a stable emulsion with water.
3. Process as defined in claim 2, in which the sulfurous acid salt is an alkali metal salt of suliurous acid.
4. Process as defined in claim 2, in which the oxidizing agent is an oxygen-containing gas.
5. Process as defined in claim 2, in which from one-third to less than one molecular quantity of the sulfurous acid salt is reacted with the unsaturated compound.
6. Process as defined in claim 2, in which the partial sulfitation is effected in the presence of a catalyst.
7. As new products, yellowish to brownish mixtures consisting essentially of partially sulfitated unsaturated fatty acid compounds, said mixtures. being capable of being emulsified in water to form stable weakly acid to alkaline emulsions and adapted for use as stufiing and reviving agents, 5 said products being obtainable by heating a starting material containing an unsaturated fatty acid compound, as such, with an aqueous solution of about a molecular quantity of a sulfurous acid salt at a temperature between about 50 C. and 10 about 100 C. while simultaneously causing an oxidizing agent to react upon the starting material, the treatment being continued until the solubility of the reaction products in water no longer increases. l5 8. As a new product, a yellowish to brownish mixture consisting essentially of partially sulfitated train oil, said mixture being capable of being emulsified in water to form a stable weakly acid to alkaline emulsion and adapted for use as 20 a stufiing and reviving agent, said mixture being obtainable by sulfitating one molecular proportion of train oil with about A; to mols of an aqueous solution of a sulfurous acid salt at from about to about C. while simultaneously 25 causing an oxidizing agent to react upon the starting material, the treatment being continued until the solubility of the reaction products in water no longer increases.
KARL O'I'I. GUSTAV
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2023769X | 1930-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2023769A true US2023769A (en) | 1935-12-10 |
Family
ID=7978494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US555142A Expired - Lifetime US2023769A (en) | 1930-09-18 | 1931-08-04 | Fatty mixture capable of being emulsified |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2023769A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3101238A (en) * | 1960-06-11 | 1963-08-20 | Bohme Fettchemie Gmbh | Fat liquoring with reaction product of epoxidized esters and polybasic inorganic acids |
| US3424770A (en) * | 1964-02-19 | 1969-01-28 | Henkel & Cie Gmbh | Process for the addition of bisulfite to compounds containing double bonds |
| US5536445A (en) * | 1984-03-21 | 1996-07-16 | Zeneca Limted | Surfactant and dispersible or emulsifiable compositions employing surfactant |
-
1931
- 1931-08-04 US US555142A patent/US2023769A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3101238A (en) * | 1960-06-11 | 1963-08-20 | Bohme Fettchemie Gmbh | Fat liquoring with reaction product of epoxidized esters and polybasic inorganic acids |
| US3424770A (en) * | 1964-02-19 | 1969-01-28 | Henkel & Cie Gmbh | Process for the addition of bisulfite to compounds containing double bonds |
| US5536445A (en) * | 1984-03-21 | 1996-07-16 | Zeneca Limted | Surfactant and dispersible or emulsifiable compositions employing surfactant |
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