US2815339A - Reaction products of primary fatty amines and ketose sugars - Google Patents
Reaction products of primary fatty amines and ketose sugars Download PDFInfo
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- US2815339A US2815339A US322812A US32281252A US2815339A US 2815339 A US2815339 A US 2815339A US 322812 A US322812 A US 322812A US 32281252 A US32281252 A US 32281252A US 2815339 A US2815339 A US 2815339A
- Authority
- US
- United States
- Prior art keywords
- fatty
- ketose
- carbon atoms
- amino groups
- anon
- Prior art date
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- Expired - Lifetime
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- 150000001412 amines Chemical class 0.000 title claims description 37
- 235000000346 sugar Nutrition 0.000 title claims description 21
- 208000007976 Ketosis Diseases 0.000 title claims description 20
- 239000007795 chemical reaction product Substances 0.000 title claims description 18
- -1 ketose sugars Chemical class 0.000 title claims description 12
- 150000002584 ketoses Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 101000597928 Homo sapiens Numb-like protein Proteins 0.000 claims 1
- 102100036986 Numb-like protein Human genes 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 description 19
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 229930091371 Fructose Natural products 0.000 description 7
- 239000005715 Fructose Substances 0.000 description 7
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 6
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- HSNZZMHEPUFJNZ-UISOVIGQSA-N (3s,4r,5r,6s)-1,3,4,5,6,7-hexahydroxyheptan-2-one Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO HSNZZMHEPUFJNZ-UISOVIGQSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LKDRXBCSQODPBY-JDJSBBGDSA-N D-allulose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@H]1O LKDRXBCSQODPBY-JDJSBBGDSA-N 0.000 description 1
- HSNZZMHEPUFJNZ-QMTIVRBISA-N D-keto-manno-heptulose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)CO HSNZZMHEPUFJNZ-QMTIVRBISA-N 0.000 description 1
- HSNZZMHEPUFJNZ-UHFFFAOYSA-N L-galacto-2-Heptulose Natural products OCC(O)C(O)C(O)C(O)C(=O)CO HSNZZMHEPUFJNZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BJHIKXHVCXFQLS-PQLUHFTBSA-N keto-D-tagatose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-PQLUHFTBSA-N 0.000 description 1
- 150000002566 ketoheptoses Chemical class 0.000 description 1
- 150000002574 ketohexoses Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002581 ketopentoses Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
Definitions
- the present invention relates to new compounds obtained by the reaction of fatty amines with ketose sugars and to the process of producing these compounds. These compounds contain a minimum of two fatty amino groups per molecule and may contain a number of fatty amino groups equivalent to the number of carbon atoms in the ketose sugar. The compounds vary in their properties with the number of fatty amine groups.
- the lower members of the group can be used directly as surface active agents or may be converted into other surface active agents by suitable reactions, such as sulfation, hydrogenation and the like.
- the compounds containing larger numbers of fatty amino groups may be used to waterproof textiles, either by direct deposition on the fabric or by reaction with formaldehyde and subsequent insolubilization on the cloth.
- the invention is applicable to ketopentoses, ketohexoses and ketoheptoses.
- Suitable sugars which may be used in the present invention include fructose, sorbose, tagatose, psicose, xyloketose, riboketose, sedoheptose, mannoketoheptose, perseulose and glucoheptulose.
- the fatty amines which may be used include the primary amines, either saturated or unsaturated, containing from 8-22 carbon atoms. These may be single, isolated amines, or may be mixed amines derived from the fatty acids of a fat or oil, or from any selected group of such fatty acids.
- Room temperature is satisfactory for the introduction of two fatty amino groups into the sugar molecule.
- the time required depends upon the temperature used and the product desired. For example, from lO-20 hours are suflicient at room temperature to introduce 2 fatty amino groups. To introduce 3 or 4 fatty amino groups requires more drastic conditions. To introduce 6 fatty amino groups into fructose, for example, may require from 4-6 hours at 70 C.
- the reaction is preferably carried out in the presence of an aqueous solvent such as a mixture of water and a lower aliphatic alcohol.
- an aqueous solvent such as a mixture of water and a lower aliphatic alcohol.
- Alcohols such as methyl, ethyl, propyl, isopropyl and the like are suited for this purpose.
- Example 2 A solution of 26.9 parts of octadecylamine and 18 parts of fructose in a mixture of two volumes of isopropyl alcohol and one volume of water was allowed to stand at room temperature for two days. The mixture was filtered, giving a crude product. After two recrystallizations from alcohol and ethyl acetate, it melted with decomposition at 1052-106 C. Analysis showed that it had been formed by the reaction of two mols of amine for each mol of sugar.
- Example 3 A solution of 26.9 parts of octadecylamine and 2.70 parts of sorbose in a mixture of 4 volumes of isopropyl alcohol and 1 volume of water was heated to 60-70 once on each of 26 days, then allowed to cool. It was filtered and the product was recrystallized from alcohol, M. P. 63.56S C. Analysis showed that between 4 and 5 mols of amine had reacted with each mol of sugar.
- Example 5 A mixture of 3 parts of the reaction product of Example 4 and 3 parts of octadecylamine in benzene was heated at 80 C. for 6 hours, cooled and filtered. Evaporation of the filtrate, followed by recrystallization of the residue from alcohol, gave a product, M. P. 67- 69.5 C. Analysis showed that it had been formed by reaction of 5 mols of amine with 1 of sugar.
- Example 6 Four parts of the reaction product of Example 4 and 4 parts of octadecylamine were dissolved in isopropyl alcohol. The mixture was heated two hours at 80 C., cooled and filtered. Recrystallization from a methanolisopropyl alcohol mixture gave a product, M. P. 65- 67 C. Analysis showed that between 5 and 6 mols of amine had reacted for each mol of sugar.
- a ketose sugar-fatty amine reaction product the ketose sugar containing from 5-7 carbon atoms, the fatty amine containing from 12-18 carbon atoms and the reaction product containing a number of fatty amino groups varying from 2 to the number of carbon atoms in the ketone sugar.
- a fructose-fatty amine reaction product the fatty amine containing from 12-18 carbon atoms and the reaction product containing from 2-6 fatty amino groups.
- a sorbose-fatty amine reaction product the fatty amine containing from 12-18 carbon atoms and the reaction product containing from 2-6 fatty amino groups.
- ketose-fatty amine reaction products which comprises reacting a ketose containing from 5-7 carbon atoms with a fatty amine containing from 12-18 carbon atoms in the range of to C. in the presence of at least 2 mols of amine per mol of ketose.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent C) REACTION PRODUCTS F PRllVIARY FATTY AMINES AND KETOSE SUGARS John G. Erickson, Minneapolis, Minn., assignor to General Mills, Inc., a corporation of Delaware N 0 Drawing. Application November 26, 1952, Serial No. 322,812
6 Claims. (Cl. 260-211) The present invention relates to new compounds obtained by the reaction of fatty amines with ketose sugars and to the process of producing these compounds. These compounds contain a minimum of two fatty amino groups per molecule and may contain a number of fatty amino groups equivalent to the number of carbon atoms in the ketose sugar. The compounds vary in their properties with the number of fatty amine groups. The lower members of the group (those containing 2 or 3 fatty amino groups per molecule) can be used directly as surface active agents or may be converted into other surface active agents by suitable reactions, such as sulfation, hydrogenation and the like. The compounds containing larger numbers of fatty amino groups may be used to waterproof textiles, either by direct deposition on the fabric or by reaction with formaldehyde and subsequent insolubilization on the cloth.
It is, therefore, an object of the present invention to provide novel reaction products of fatty amines and ketose sugars in which the compounds contain at least two fatty amino groups per molecule.
It is another object of the present invention to provide a process of producing such compounds.
The invention is applicable to ketopentoses, ketohexoses and ketoheptoses. Suitable sugars which may be used in the present invention include fructose, sorbose, tagatose, psicose, xyloketose, riboketose, sedoheptose, mannoketoheptose, perseulose and glucoheptulose. By means of the present invention it is possible to introduce a fatty amino group onto each carbon atom of the ketose sugar.
The fatty amines which may be used include the primary amines, either saturated or unsaturated, containing from 8-22 carbon atoms. These may be single, isolated amines, or may be mixed amines derived from the fatty acids of a fat or oil, or from any selected group of such fatty acids.
In preparing these products it is desirable to use an excess of amine over the theoretical quantity of amine required to introduce the desired number of fatty amino groups into the sugar. The introduction of two fatty groups into the molecule may be attained even without the employment of an excess of amine. For example, octadecylamine and fructose in equimolar quantities yield the dioctadecylamino fructose compound merely upon allowing the mixture to stand at room temperature for 24 hours. However, even in this instance it is preferred to use a ratio of at least 2 mols of amine to 1 of sugar. Where it is desired to introduce higher numbers of fatty amine groups, it is preferred to use still higher ratios of amine to sugar; for example, as high as 8 to 10 mols of amine per mol of sugar where it is desired to introduce 5 or 6 fatty amino groups.
Room temperature is satisfactory for the introduction of two fatty amino groups into the sugar molecule. In order to obtain more highly substituted products it is preferred to heat the reactants together at temperatures within the range of 30-100 C. Temperatures in excess Patented Dec. 3, 1957 of C. tend toward excessive decomposition. The preferred temperature range is 50-80 C. The time required depends upon the temperature used and the product desired. For example, from lO-20 hours are suflicient at room temperature to introduce 2 fatty amino groups. To introduce 3 or 4 fatty amino groups requires more drastic conditions. To introduce 6 fatty amino groups into fructose, for example, may require from 4-6 hours at 70 C.
The reaction is preferably carried out in the presence of an aqueous solvent such as a mixture of water and a lower aliphatic alcohol. Alcohols such as methyl, ethyl, propyl, isopropyl and the like are suited for this purpose.
There are numerous possibilities for the structure of these compounds and for the course which the reaction takes. The following reactions indicate the courses which the reaction may take and the products which may be obtained.
anion anion ano CH=YNR i=0 (|J=NR OHNHR CHNHR anon RNH: anon anon RNH, anon anon anon anon V anon anon anon anon anon CHZOH OHzOH CHzOH 0112011 OHZNHR anmnn OHZNHR CIEHNHR anNnR CHNHR a=o RNH: G=NR CHNHR n A} non anon =0 anon anon anon angon anzon anion anion anion anzon (IJHNHR anNnR anNnR a=o RNn. C=NR CHNHR I anon anon =0 anon anon anon anion CHzOH anion These reactions may continue until all oxygen in the sugar has been replaced by nitrogen. Obviously, a large number of different compounds is possible. Not only the straight-chain forms shown above can be formed, but also others such as:
OH OH CHzOH CHzNHR CHNHR CIHENHR CHNHR OHNHR HrNHR JHNHR CHNHR JHNHR and CHNHR C IHNHR i=0 CHNHR CH=NR (IJHZOH CH=NR Besides these straight-chain forms, one can get their cyclized forms. Some of these are:
RNHCH CH2 CH RNHCH RNHC H RNHJJH RNBI IH O, RNHC I'H O, RNEK JH 0, etc. RNHC JH RNHCH RNHCH HC- RNHC HOC I HzOH H2015 JHzOH Example 1 A solution of 5.4 parts 'of fructose and 11.1 parts of dodecylamine in a mixture of equal volumes of water and isopropyl alcohol was allowed to stand at room temperature for days. 'It was then filtered and the reaction product was recrystallized from a low-boiling paraflin hydrocarbon. The pure product melts with decomposition at 103.5-104.5 C. Analysis showed that it had been formed by the reaction of 2 mols of dodecylamine with 1 mol of fructose.
Example 2 A solution of 26.9 parts of octadecylamine and 18 parts of fructose in a mixture of two volumes of isopropyl alcohol and one volume of water was allowed to stand at room temperature for two days. The mixture was filtered, giving a crude product. After two recrystallizations from alcohol and ethyl acetate, it melted with decomposition at 1052-106 C. Analysis showed that it had been formed by the reaction of two mols of amine for each mol of sugar.
Example 3 A solution of 26.9 parts of octadecylamine and 2.70 parts of sorbose in a mixture of 4 volumes of isopropyl alcohol and 1 volume of water was heated to 60-70 once on each of 26 days, then allowed to cool. It was filtered and the product was recrystallized from alcohol, M. P. 63.56S C. Analysis showed that between 4 and 5 mols of amine had reacted with each mol of sugar.
Example 5 A mixture of 3 parts of the reaction product of Example 4 and 3 parts of octadecylamine in benzene was heated at 80 C. for 6 hours, cooled and filtered. Evaporation of the filtrate, followed by recrystallization of the residue from alcohol, gave a product, M. P. 67- 69.5 C. Analysis showed that it had been formed by reaction of 5 mols of amine with 1 of sugar.
Example 6 Four parts of the reaction product of Example 4 and 4 parts of octadecylamine were dissolved in isopropyl alcohol. The mixture was heated two hours at 80 C., cooled and filtered. Recrystallization from a methanolisopropyl alcohol mixture gave a product, M. P. 65- 67 C. Analysis showed that between 5 and 6 mols of amine had reacted for each mol of sugar.
Other ketone sugars containing 5-7 carbon atoms may be substituted for the sugars disclosed in the examples with similar results.
I claim as my invention:
1. A ketose sugar-fatty amine reaction product, the ketose sugar containing from 5-7 carbon atoms, the fatty amine containing from 12-18 carbon atoms and the reaction product containing a number of fatty amino groups varying from 2 to the number of carbon atoms in the ketone sugar.
2. A fructose-fatty amine reaction product, the fatty amine containing from 12-18 carbon atoms and the reaction product containing from 2-6 fatty amino groups.
3. A sorbose-fatty amine reaction product, the fatty amine containing from 12-18 carbon atoms and the reaction product containing from 2-6 fatty amino groups.
4. Process of preparing ketose-fatty amine reaction products containing at least 2 fatty amino groups which comprises reacting a ketose containing from S-7 carbon atoms with a fatty amine containing from 12-18 carbon atoms, the fatty amine being employed in excess of the theoretical quantity required for the introduction of the desired number of fatty amino groups, at a temperature within the range of 40 to 100 C.
5. Process of producing ketose-fatty amine reaction products which comprises reacting a ketose containing from 5-7 carbon atoms with a fatty amine containing from 12-18 carbon atoms in the range of to C. in the presence of at least 2 mols of amine per mol of ketose.
6. Process of producing ketose-fatty amine reaction products which comprises reacting a ketose containing from 5-7 carbon atoms with a fatty amine containing from 12-18 carbon atoms, the fatty amine being employed in a molar ratio at least 3 times that of the ketose at a temperature within the approximate range of 50- References Cited in the file of this patent UNITED STATES PATENTS 2,016,962 Flint et al. Oct. 8, 1935 2,016,956 Calcott et al. Oct. 8, 1935 2,181,929 Werntz Dec. 5, 1939 FOREIGN PATENTS 519,381 Great Britain Mar. 26, 1940 OTHER REFERENCES Votocek et al.: Collection Trav. Chim. Tckecoslovaquie, vol. 6 (1934), pp. 77-96. (Pages 93-5 relied upon.) (Copy in the Bureau of Geological Survey Library.)
Mitts et al.: J. A. C. S., 66, 483 (1944).
Mitts et al.: J. A. C. 8., vol. 66, PP. 483-6 (1944).
Erickson: J. A. C. 8., vol. 77, page 2840 (1955).
Claims (2)
1.A KETOSE SUGAR-FATTY AMINE REACTION PRODUCT, THE KETOSE SUGER CONTAINING FROM 5-7 CARBON ATOMS, THE FATTY AMINE CONTAINING FROM 12-18 CARBON ATOMS AND THE REACTION PRODUCT CONTAINING A NUMBR OF FATTY AMINO GROUPS VARYING FROM 2 TO THE NUMBER OF CARBON ATOMS IN THEEKETONE SUGAR.
4. PROCESS OF PREPARING KETOSE-FATTY AMINE REACTION PRODUCTS CONTAINING AT LEAST 2 FATTY AMINO GROUPS WHICH COMPRISES REACTING A KETOSE CONTAINING FROM 5-7 CARBON ATOMS WITH A FATTY AMINE CONTAINING FROM 12-18 CARBON ATOMS WITH FATTY AMINE BEING EMPLOYED IN EXCESS OF THE THEORETICAL QUANTITY REQUIRED FOR THE INTRODUCTION OF THE DESIRED NUMBER OF GATTY AMINO GROUPS, AT A TEMPERATURE WITHIN THE RANGE IF 40 TO 100* C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US322812A US2815339A (en) | 1952-11-26 | 1952-11-26 | Reaction products of primary fatty amines and ketose sugars |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US322812A US2815339A (en) | 1952-11-26 | 1952-11-26 | Reaction products of primary fatty amines and ketose sugars |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2815339A true US2815339A (en) | 1957-12-03 |
Family
ID=23256537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US322812A Expired - Lifetime US2815339A (en) | 1952-11-26 | 1952-11-26 | Reaction products of primary fatty amines and ketose sugars |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2815339A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2918462A (en) * | 1956-01-20 | 1959-12-22 | Ciba Pharm Prod Inc | Process for the preparation of amino-aldehydes |
| US4021539A (en) * | 1974-01-29 | 1977-05-03 | Henkel & Cie G.M.B.H. | Skin treating cosmetic compositions containing N-polyhydroxyalkyl-amines |
| FR2523150A1 (en) * | 1982-03-11 | 1983-09-16 | Cirta Ct Int Rech Tech Appliqu | SURFACTANTS AND PROCESS FOR THE PREPARATION OF SUCH AGENTS |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2016962A (en) * | 1932-09-27 | 1935-10-08 | Du Pont | Process for producing glucamines and related products |
| US2016956A (en) * | 1932-11-04 | 1935-10-08 | Du Pont | Amino derivatives and process of preparing them |
| US2181929A (en) * | 1937-09-21 | 1939-12-05 | Du Pont | Maltosamine and process for preparing it |
| GB519381A (en) * | 1937-09-21 | 1940-03-26 | Du Pont | Manufacture of maltosamines |
-
1952
- 1952-11-26 US US322812A patent/US2815339A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2016962A (en) * | 1932-09-27 | 1935-10-08 | Du Pont | Process for producing glucamines and related products |
| US2016956A (en) * | 1932-11-04 | 1935-10-08 | Du Pont | Amino derivatives and process of preparing them |
| US2181929A (en) * | 1937-09-21 | 1939-12-05 | Du Pont | Maltosamine and process for preparing it |
| GB519381A (en) * | 1937-09-21 | 1940-03-26 | Du Pont | Manufacture of maltosamines |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2918462A (en) * | 1956-01-20 | 1959-12-22 | Ciba Pharm Prod Inc | Process for the preparation of amino-aldehydes |
| US4021539A (en) * | 1974-01-29 | 1977-05-03 | Henkel & Cie G.M.B.H. | Skin treating cosmetic compositions containing N-polyhydroxyalkyl-amines |
| FR2523150A1 (en) * | 1982-03-11 | 1983-09-16 | Cirta Ct Int Rech Tech Appliqu | SURFACTANTS AND PROCESS FOR THE PREPARATION OF SUCH AGENTS |
| WO1983003252A1 (en) * | 1982-03-11 | 1983-09-29 | Michel, Jean-Pierre | Surfactants and preparation method thereof |
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