USRE21530E - Acid substituted hydroxy alkylr- - Google Patents
Acid substituted hydroxy alkylr- Download PDFInfo
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- USRE21530E USRE21530E US21530DE USRE21530E US RE21530 E USRE21530 E US RE21530E US 21530D E US21530D E US 21530DE US RE21530 E USRE21530 E US RE21530E
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- United States
- Prior art keywords
- acid
- hydroxy
- condensation products
- alkylolamines
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 title description 18
- 239000002253 acid Substances 0.000 title description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000007859 condensation product Substances 0.000 description 25
- 235000014113 dietary fatty acids Nutrition 0.000 description 25
- 229930195729 fatty acid Natural products 0.000 description 25
- 239000000194 fatty acid Substances 0.000 description 25
- 150000004665 fatty acids Chemical class 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 14
- 239000002270 dispersing agent Substances 0.000 description 12
- -1 hydroxy alkylamines Chemical class 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 235000021355 Stearic acid Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 6
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 6
- 239000008117 stearic acid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- 239000005639 Lauric acid Substances 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002169 ethanolamines Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 238000009738 saturating Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- VVLAIYIMMFWRFW-UHFFFAOYSA-N 2-hydroxyethylazanium;acetate Chemical compound CC(O)=O.NCCO VVLAIYIMMFWRFW-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101100408384 Danio rerio piwil2 gene Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- UPCXAARSWVHVLY-UHFFFAOYSA-N tris(2-hydroxyethyl)azanium;acetate Chemical compound CC(O)=O.OCCN(CCO)CCO UPCXAARSWVHVLY-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 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
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/175—Amines; Quaternary ammonium compounds containing COOH-groups; Esters or salts thereof
-
- 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
-
- 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
- C09K23/16—Amines or polyamines
Definitions
- My invention relates to a new class of chemical compouncb and to a process for preparing such compoimds.
- the chief object of the invention is the production of new chemical compounds or reactirm mixtures comprising condensation products containing such novel chemical compounds.
- hydroxy alkylamines or alblolamines may be condensed with higher molecular weight organic acid substances or acylating compounds such as the free acids, esters of such acids such as the monoglycerides, or halides of such acids, or any other derivative thereof which will condense with the ivdroxy alkylamine or alkylolamine to split out water or acids so as to bring about a union of the two molecules.
- acylating compounds such as the free acids, esters of such acids such as the monoglycerides, or halides of such acids, or any other derivative thereof which will condense with the ivdroxy alkylamine or alkylolamine to split out water or acids so as to bring about a union of the two molecules.
- amides and ester-amidw may and usually do form, in certain cases, in predominating amounts.
- condensation products will form by the union of the monoethanolamine or the like with the higher molecular weight 'organic acid or derivative thereof with the splitting out of either water or an acid.
- the resulting condensation products are, in general, basic and form salts with any chemicals having acidic groups as, for example, hydrochloric acid, acetic acid and the like.
- condensation products of my invention are sharply distinguishable in chemical structure from and have many radically different properties than the salts or soaps resulting from the interaction of hydroxy alkylamines with higher fatty acids or the like.
- the two compounds combine, forming an addition product.
- reaction temperature which is sufiicientl'y high to split out water or an acid as a result of the union of the molecules of hydroxy alkylamine and higher molecular weight organic acid substance or acylating compound.
- free acid is employed in the condensation reaction, in which case water splits out
- a temperature of at least about degrees C. should be utilized.
- One molof monoethanolamine is condensed with one mol of stearlc acid at 150 degrees c, t 175 degrees C. for two to four hours, while stirring.
- One moi of diethanolamine is condensed withonemoloilaurlcacidat 150degreesC.to l'liidegreescJortwotoiourhoin-s.
- the hydroxy aikylamines or alkylolamines whichmay be employed in the condensation reaction include. in addition to those mentioned in the various examples, primary, secondary and tertiary hydroxy alkylamines or. alkylolamines such as the propanoiamines, butanolamines, ethanol hutanolamines, diethanol butanolamines; alkyl derivatives of hydroxy alkylamines or alkylolamines, that is. hydro alkylamines wherein hydrogen attached to nitrogen is replaced byalkyl such as ethyl, methyl, butyl and the like; as
- emulsifying and dispersing agents as preeipitants, as wetting agents and the like.
- they may be employed in dispersions or emulsions containing water and water-immiscible materials such as oils.
- the condensation products have valuable properties also in the dye industry where, for example, they may be employed to disperse vat dyestuflsinaqueousmedimaswellasforthe production of -modered dye products as disclosed in Patent No. 2,022,678.
- condensation product it' will be imderstcod to cover a re action product between an acid or acylating compound and an alkylolamine wherein wateror a'ci'd orthe likeissplit outasaresult of theunion oi the molecules of acid or acylatlng compound and alkyloiamine: similarly, the term “condensing” is employed to cover aprocess wherein water polmd and alkylolamine.
- acylating compound is intended to coversuchcompmmdsas free higher fatty acids, acyl halidescthereoi and other compounds whichreactwith alkylolaminestointroduce an acyl radical thereinto.
- An ester-amide oi a-hydroxy-alkyi amine and a vegetal fatty acid. 8. A neutralized ester-amide of a hydroxyaliwl amine andahigherfattyacid.
- Theprocess for the manufacture ofdis- 10 The process for the manufacture of dispersing agents which comprises condensing a trihydroxy-alkyl amine with a higher aliphatic acylating compound.
- Dispersing agents comprising a condensation product of a di-hydroxy-alkyl amine and a higher aliphatic acylating compound.
- Dispersing agents comprising an ester of a tri-hydroxy-alkyl amine with a higher aliphatic acylating compound.
- Dispersing agents comprising a condensation product of a hydroxy-ethyl amine and a higher fatty acylating compound.
- Dispersing agents comprising an amide of an alkylolamine containing a primary hydroxy group and a higher aliphatic acylating compound.
- a neutralized ester of a hydroxy-alkyl amine having at least two hydroxy groups and a higher aliphatic acylating compound is provided.
- Dispersing agents comprising an ester of a hydroxy-alkyl amine having at least two hydroxy groups and a higher fatty acid.
- Dispersing agents comprising higher fatty acid amides of monoethanolamine.
- Condensation products in accordance with claim 31 wherein the higher fatty acid is a member selected from the group consisting of stearic acid, oleic acid, and lauric acid.
- Condensation products in accordance with claim 35 wherein the higher fatty acids are selected from the group consisting of stearic acid, oleic acid, and lauric acid.
- a higher fatty acid amide of a hydroflallgvl amine containing a primary hydrcxy group is provided.
Description
Reissued Aug. 13, 1940 ACID ZILI I L mm AMINES AND PROCESS OI ROXY ALKYL- MAKING SAME Wolf Chicago, 111..
Ninol, Ina, (hicago, Ill. Illinois I Y alignmto a corporation of No. 2,173,058, dated Sopol'llillll tember 12, 19, Seth! No. 271,711, May
1939. Serial No. 3303'" Claims.
My invention relates to a new class of chemical compouncb and to a process for preparing such compoimds.
The chief object of the invention is the production of new chemical compounds or reactirm mixtures comprising condensation products containing such novel chemical compounds.
I have discovered that hydroxy alkylamines or alblolamines may be condensed with higher molecular weight organic acid substances or acylating compounds such as the free acids, esters of such acids such as the monoglycerides, or halides of such acids, or any other derivative thereof which will condense with the ivdroxy alkylamine or alkylolamine to split out water or acids so as to bring about a union of the two molecules. In the case of tertiary hydroxy alkylamines such as triethanolamine, for example, only esters are formed. In those cases where a non-tertiary go alkylolamine as, by way of illustration, a monohydroxy alhlolamine, such as monoethanolamine, is condensed with a higher fatty acid, as shown for example in Examples 1, 2 and 9, amides and ester-amidw may and usually do form, in certain cases, in predominating amounts.
Thus, for example, more specifically, I have found that when monoethanolamine or any hydroxy almlamine is condensed with a vegetal fatty acid or a higher molecular weight organic acid, preferably a fatty acid such as stearic acid, oleic acid, linoleic'acid, or a higher molecular weight fatty acid halide or monoglyceride or any ester 01' ajhigher fatty acid with a polyhydroxy 'alcohol, or higher molecular weight organic sulpho-chlorides or sulphonic acid derivatives of higher molecular weight organic compounds or any other reactive group, condensation products will form by the union of the monoethanolamine or the like with the higher molecular weight 'organic acid or derivative thereof with the splitting out of either water or an acid. The resulting condensation products are, in general, basic and form salts with any chemicals having acidic groups as, for example, hydrochloric acid, acetic acid and the like.
The condensation products of my invention are sharply distinguishable in chemical structure from and have many radically different properties than the salts or soaps resulting from the interaction of hydroxy alkylamines with higher fatty acids or the like. In the case of the formation of the salts or soaps of the hydroxy alkylamines with higher fatty acids or the like, the two compounds combine, forming an addition product. on the other hand, my condensation Application for reissue April 18, 1940,
products result from a union of the hydroxy alkylamine with the higher fatty acid or the like whereby water or an acid, as stated, splits out.
It will be seen, therefore, that in the production of the condensation products of my invention a reaction temperature must be employed which is sufiicientl'y high to split out water or an acid as a result of the union of the molecules of hydroxy alkylamine and higher molecular weight organic acid substance or acylating compound. Where the free acid is employed in the condensation reaction, in which case water splits out, it will be seen that a temperature of at least about degrees C. should be utilized. However, for appreciable speed of reaction, it is advisable to employ more elevated temperatures and, as a general rule, a temperature range of degrem C. to degrees C. will serve in most cases. It,
will be understood, of course, that temperature. somewhat lower than the preferred range may be employed as well as higher temperatures but in no case, obviously, will the temperature be suiiiciently high to cause decomposition of the reacting ingredients or the resulting product. The length of time for carrying out the reaction will likewise vary but, within the preferred temperature operating range, a few hours will usually sufllce, excellent results being obtained in most cases by carrying out the reaction for from two to four hours.
For the benefit of those skilled in the art, I give hereinafter a number of representative examples which are by no means exhaustive .but which I deem suflicient to teach those skilled in the art the manner in which my invention may be practiced:
1. One molof monoethanolamine is condensed with one mol of stearlc acid at 150 degrees c, t 175 degrees C. for two to four hours, while stirring.
2. One mol of monoethanolamine acetate is condensed with one mol of stearic acid at 150 degrees C. to 175 degrees C. for two to four hours, while stirring.
3. One mol of triethanolamine is condensed with one mol of linoleic acid at 150 degrees C. to 1'75 degrees C. for two to four hours, while stirring.
4. One mol of triethanolamine acetate is condensed with one mol of linoleic acid at 150 degrees C. to 1'15 degrees C. for two to four hours, while stirring.
5. One mol .of benzoyl chloride is condensed with one mol of methyl diethanolamine at 150 (worrisome. forahoutthneor whilestirring Onemolo molhftriethanolamin ati'lfidegreesc. for ourhourawhilestin'ing.
7.Cmemo1ofabieticacidiscondensedwith molofbutyldiethanolamlne at1li0 degrea C. tol'liidegrees C. forthreetofour hours, while I 8. Twomolsofahighermolecmar weight fatty acldchloridesuchasstearicacidchlorideare 9. Twomolsofahighermolecuiarweightfatty acid,suchasstcarlcacid.arecondensedwithone moi-of monoethanolamine at iiiodegrees C. to 1'15 degrees C. fortwotofourhours, with stirring.
10. One mol of triethandamine is condensed.
withonemoiofuearicacidat 150de'greesC.to 175 degrees C. fortwoto fourhours, withstirring. 11. One moi of palmitic acid is condensed with onemolottriethanolamineatiwdegreescto 175 degrees C. for two to fo'urhours, with stir- 12. One moi of lauric acid is condensed with 'onemoioi'trlethanolamineatahout 175 degrees C. for two to four hours, with stirring.
13.0nemoiofstearicacidiscondensedwith onemoiofasecondaryhydronalkylaminesuch asdlethanolamineatlwdegreesatoi'lidegrees C.-iortwotofourhours.
14. One moi of triethanolamine is condensed with onemoloi oleicaeidatabout i'lfid'egrees Gloriourhours.
-15. One mol of monoethanoiamine is condcnsed with one moi oflauric acid at about 175' degreescforfourhours. 18.0nemo1 of monoethanolamineiscondensedwithonemoioioleicacidatlfiildegrees qtoi'mdegreeaafortwotofourhours.
17. One moi of diethanolamine is condensed withonemoloilaurlcacidat 150degreesC.to l'liidegreescJortwotoiourhoin-s.
Itisclearthatthehydroxyalkylaminuandthe higherfattyacidsorthelikemaybecondensed in varying molai proportions Thus, for example, one moi of the hydron alblamine. such as. trlethanolamine. may be condensed with one,-
twoorthreemolsothigheri'attyacidorthelike. The hydroxy aikylamines or alkylolamines whichmay be employed in the condensation reaction include. in addition to those mentioned in the various examples, primary, secondary and tertiary hydroxy alkylamines or. alkylolamines such as the propanoiamines, butanolamines, ethanol hutanolamines, diethanol butanolamines; alkyl derivatives of hydroxy alkylamines or alkylolamines, that is. hydro alkylamines wherein hydrogen attached to nitrogen is replaced byalkyl such as ethyl, methyl, butyl and the like; as
well as mixtures of: these and other hydronQalmaasnmuenmmm bensoyl chloride, stearic acid chloride, and like. Of particular usefulness are the molecular-weight fattyacidswhicharederi fromoilsandfatsoi'animalandvegetableoriain andwhichmaybedenotedasvegetalfattyauds. It will be understood. ofcourse, that mixtures oftheseaswellasotherhiaherorsanic acidsor pounds may be employed and that such condensed with either substantially pure hydrow alkylamines or mixtures thereof such as Wmay be found, for example, in commercial prod- The condensation products of my invention iunction. among other things, as emulsifying and dispersing agents, as preeipitants, as wetting agents and the like. Thus, for example, they may be employed in dispersions or emulsions containing water and water-immiscible materials such as oils. The condensation products have valuable properties also in the dye industry where, for example, they may be employed to disperse vat dyestuflsinaqueousmedimaswellasforthe production of -modiiled dye products as disclosed in Patent No. 2,022,678.
Wherever the term "condensation product is employed, it' will be imderstcod to cover a re action product between an acid or acylating compound and an alkylolamine wherein wateror a'ci'd orthe likeissplit outasaresult of theunion oi the molecules of acid or acylatlng compound and alkyloiamine: similarly, the term "condensing" is employed to cover aprocess wherein water polmd and alkylolamine. i
The term "acylating compound", as used herein, is intended to coversuchcompmmdsas free higher fatty acids, acyl halidescthereoi and other compounds whichreactwith alkylolaminestointroduce an acyl radical thereinto.
The present application is a continuation-inpart of my earlier application, Serial No. 478.235. flied August 18, 1930.
WhatIcla-imasnewanddeslreto protecthy Reissue Letters Patent of the United States is:
1. A chemical compound in the form of an ester comprising triethanolamine in which one -H of the "OE" groups is substituted by a hither organic acid substances or acylating com- I. acidortheiikeissplitoutasa'resultofthe. unionofthemoleculesofacidoracylating com- 6. An ester-amide ofa hydrm-alkyl amine and a higher aliphatic acyiating compoimd.
'1. An ester-amide oi a-hydroxy-alkyi amine and a vegetal fatty acid. 8. A neutralized ester-amide of a hydroxyaliwl amine andahigherfattyacid.
9.Theprocess for the manufacture ofdis- 10. The process for the manufacture of dispersing agents which comprises condensing a trihydroxy-alkyl amine with a higher aliphatic acylating compound.
11. Dispersing agents comprising a condensation product of a di-hydroxy-alkyl amine and a higher aliphatic acylating compound.
12. Dispersing agents comprising an ester of a tri-hydroxy-alkyl amine with a higher aliphatic acylating compound.
13. Dispersing agents comprising a condensation product of a hydroxy-ethyl amine and a higher fatty acylating compound.
14. An ester of an aliphatic hydroxy-ethyl mono-amine with a vegetal fatty acid.
15. An ester of a tri-hydron-ethyl amine with a vegetal fatty acid.
16. Condensation products of higher fatty acids with a member selected from the group consisting of mono-ethanolamine, diethanolamine, triethanolamine and mixtures thereof.
17. Dispersing agents comprising an amide of an alkylolamine containing a primary hydroxy group and a higher aliphatic acylating compound.
18. The process for the manufacture of dispersing agents which comprises condensing a higher fatty acylating compound with a hydroiwalkyl amine containing hydrogen directly attached to nitrogen and containing a primary hydroxy group.
19. The process for the manufacture of dispersing agents which comprises condensing a hydroxy-alkyl amine containing hydrogen directly attached to nitrogen and a primary hydroxy group with a higher aliphatic acylating compound in a quantity insufficient for saturating both hvdroxy and amino groups present in the molecule of the hydroxy-alkyl amine emp oyed- 20. The process for the manufacture of dispersing agents which comprises condensing a hydroxy-alkyl amine containing hydrogen directly attached to nitrogen with a higher aliphatic acylating compound in a quantity suiiicient i'or saturating hydroxyl and amino groups present in the molecule of the hydroxy-alkyl amine employed.
21. An ester of a hydroxy-alkyl amine having at least two hydroxy groups and a higher aliphatic acylating compoimd.
22. A neutralized ester of a hydroxy-alkyl amine having at least two hydroxy groups and a higher aliphatic acylating compound.
23. Dispersing agents comprising an ester of a hydroxy-alkyl amine having at least two hydroxy groups and a higher fatty acid.
24. Condensation products of higher fatty acids with alnlolamines containing hydrogen directly connected to nitrogen and at least one primary hydroxy group.
25. Condensation products of higher aliphatic acids and alkylolamines-containing at least one Cal-140K group and wherein hydrogen directly attached to the nitrogen otthe alkylolamines is replaced by aikyl.
. Condensation products of higher aliphatic acids and alkylolamines containing at least one CaHsOHI group and wherein hydrogen directly attached to the nitrogen of the alkylolamines is replaced by methyl. I
27. Condensation products of higher fatty acids and alkylolamines containing at least one CzH'AOH group and wherein hydrogen directly attached to the nitrogen of the alkylolamines is replaced by alhl.
28. Condensation products of higher fatty acids and alkylolamines containing at least one Cal-140E group and wherein hydrogen directly attached to the nitrogen of the alkylolamines is replaced by methyl.
29. The process for the manufacture of dispersing agents which comprises condensing a higher aliphatic acylating compound with a hydroxy-alkyl amine containing both a primary amino and a primary hydroxy group.
30. A condensation product of a higher aliphatic acylating compound with a hydroxyalkyl amine containing hydrogen directly attached to nitrogen and a primary hydroxy group.
31. Dispersing agents comprising higher fatty acid amides of monoethanolamine.
32. Condensation products in accordance with claim 31 wherein the higher fatty acid is a member selected from the group consisting of stearic acid, oleic acid, and lauric acid.
33. Condensation products of diethanolamine with a higher fatty acid selected from the group consisting of stearic acid, oleic acid, and lauric acid.
34. Condensation products of higher fatty acids and hydroxy-alkyl amines containing at least one ChHrOH group.
35. Condensation products of alkylolamines having at least two hydroxy groups with higher fatty acids.
36. Condensation products of alkylolamines containing hydrogen directly attached to nitrogen with higher fatty aclds selected from the group consisting of stearic acid, oleic acid, and lauric acid. Y
37. Condensation products in accordance with claim 35 wherein the higher fatty acids are selected from the group consisting of stearic acid, oleic acid, and lauric acid.
38. Condensation products of higher molecular weight aliphatic acylating compounds with alkylolamines containing a primary hydroxy group and wherein said primary hydroxy group of the alkylolamines is directly attached to a carbon atom other than a carbon atom to which nitrogen of the alkylolamines is directly attached and wherein alkyl is directly attached to nitrogen of theallgvlolamines.
39. Condensation products of higher molecular weight fatty acid acylating compounds with ethanolamines containing a primary hydroxy group and wherein said primary hydroxy group of the ethanolamines is directly attached to a carbon atom other than a carbon atom to which nitrogen of the ethanolamines is directly attached and wherein methyl is directly attached to nitrogen of the ethanolamines.
40. A higher fatty acid amide of a hydroflallgvl amine containing a primary hydrcxy group.
Publications (1)
Publication Number | Publication Date |
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USRE21530E true USRE21530E (en) | 1940-08-13 |
Family
ID=2087357
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US21530D Expired USRE21530E (en) | Acid substituted hydroxy alkylr- |
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US (1) | USRE21530E (en) |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2440349A (en) * | 1944-11-14 | 1948-04-27 | Us Agriculture | Process for preparing an alkylolamide of a trihydroxystearic acid |
US2545357A (en) * | 1946-06-04 | 1951-03-13 | American Cyanamid Co | Detergent composition and method of preparing same |
US2586496A (en) * | 1947-03-08 | 1952-02-19 | Swift & Co | Detergent composition and process of preparing same |
US2605270A (en) * | 1949-06-21 | 1952-07-29 | Swern Daniel | Amides of 9, 10-dihydroxystearic acid |
US2608562A (en) * | 1949-06-07 | 1952-08-26 | Edward T Roe | Method of producing amides |
US2665188A (en) * | 1951-01-03 | 1954-01-05 | Gen Aniline & Film Corp | Stabilization of the viscosities of vat dye pastes |
US2683088A (en) * | 1952-06-10 | 1954-07-06 | American Cyanamid Co | Soft bibulous sheet |
US2683089A (en) * | 1952-06-10 | 1954-07-06 | American Cyanamid Co | Bibulous sheet |
US2703798A (en) * | 1950-05-25 | 1955-03-08 | Commercial Solvents Corp | Detergents from nu-monoalkyl-glucamines |
US2744888A (en) * | 1950-08-04 | 1956-05-08 | American Cyanamid Co | Ethenoxy n-monoethanolamides of tall oil |
US2913417A (en) * | 1959-11-17 | Detergent composition | ||
US3091521A (en) * | 1960-05-03 | 1963-05-28 | Standard Oil Co | Gasoline composition |
US3113104A (en) * | 1959-11-25 | 1963-12-03 | Frederick C Bersworth | Method and composition for control of fish odors and odors of proteinaceous origin |
DE2728237A1 (en) * | 1977-06-23 | 1979-01-18 | Henkel Kgaa | DISPERSING PIGMENTS |
US4867911A (en) | 1987-07-13 | 1989-09-19 | Pennzoil Products Company | Surface treating water-in-oil emulsion composition and method |
US4891073A (en) | 1987-07-13 | 1990-01-02 | Pennzoil Products Company | Method of treating surface with water-in-oil emulsion composition |
US5023283A (en) * | 1986-12-24 | 1991-06-11 | Ciba-Geigy Corporation | N,N-bis(acyloxyethyl)hydroxylamine derivatives |
-
0
- US US21530D patent/USRE21530E/en not_active Expired
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2913417A (en) * | 1959-11-17 | Detergent composition | ||
US2440349A (en) * | 1944-11-14 | 1948-04-27 | Us Agriculture | Process for preparing an alkylolamide of a trihydroxystearic acid |
US2545357A (en) * | 1946-06-04 | 1951-03-13 | American Cyanamid Co | Detergent composition and method of preparing same |
US2586496A (en) * | 1947-03-08 | 1952-02-19 | Swift & Co | Detergent composition and process of preparing same |
US2608562A (en) * | 1949-06-07 | 1952-08-26 | Edward T Roe | Method of producing amides |
US2605270A (en) * | 1949-06-21 | 1952-07-29 | Swern Daniel | Amides of 9, 10-dihydroxystearic acid |
US2703798A (en) * | 1950-05-25 | 1955-03-08 | Commercial Solvents Corp | Detergents from nu-monoalkyl-glucamines |
US2744888A (en) * | 1950-08-04 | 1956-05-08 | American Cyanamid Co | Ethenoxy n-monoethanolamides of tall oil |
US2665188A (en) * | 1951-01-03 | 1954-01-05 | Gen Aniline & Film Corp | Stabilization of the viscosities of vat dye pastes |
US2683089A (en) * | 1952-06-10 | 1954-07-06 | American Cyanamid Co | Bibulous sheet |
US2683088A (en) * | 1952-06-10 | 1954-07-06 | American Cyanamid Co | Soft bibulous sheet |
US3113104A (en) * | 1959-11-25 | 1963-12-03 | Frederick C Bersworth | Method and composition for control of fish odors and odors of proteinaceous origin |
US3091521A (en) * | 1960-05-03 | 1963-05-28 | Standard Oil Co | Gasoline composition |
DE2728237A1 (en) * | 1977-06-23 | 1979-01-18 | Henkel Kgaa | DISPERSING PIGMENTS |
US4165239A (en) | 1977-06-23 | 1979-08-21 | Henkel Kommanditgesellschaft Auf Aktien | Process for dispersing pigments and fillers using carboxylic acid esters of tertiary alkylolamines |
US5023283A (en) * | 1986-12-24 | 1991-06-11 | Ciba-Geigy Corporation | N,N-bis(acyloxyethyl)hydroxylamine derivatives |
US4867911A (en) | 1987-07-13 | 1989-09-19 | Pennzoil Products Company | Surface treating water-in-oil emulsion composition and method |
US4891073A (en) | 1987-07-13 | 1990-01-02 | Pennzoil Products Company | Method of treating surface with water-in-oil emulsion composition |
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