USRE21530E - Acid substituted hydroxy alkylr- - Google Patents

Acid substituted hydroxy alkylr- Download PDF

Info

Publication number
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
Authority
US
United States
Prior art keywords
acid
hydroxy
condensation products
alkylolamines
group
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
Application number
Publication date
Application granted granted Critical
Publication of USRE21530E publication Critical patent/USRE21530E/en
Expired legal-status Critical Current

Links

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.
US21530D Acid substituted hydroxy alkylr- Expired USRE21530E (en)

Publications (1)

Publication Number Publication Date
USRE21530E true USRE21530E (en) 1940-08-13

Family

ID=2087357

Family Applications (1)

Application Number Title Priority Date Filing Date
US21530D Expired USRE21530E (en) Acid substituted hydroxy alkylr-

Country Status (1)

Country Link
US (1) USRE21530E (en)

Cited By (17)

* Cited by examiner, † Cited by third party
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

Cited By (18)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
USRE21530E (en) Acid substituted hydroxy alkylr-
US2340881A (en) Composition for lubricating and softening textile fibers
US2425392A (en) Diamide textile lubricants
US2176896A (en) Quaternary ammonium derivatives of amides
US2368208A (en) Chemical compounds and method of preparing same
US2173058A (en) Acid substituted hydroxy alkylamines and process of making same
JPS5857348A (en) Bisamides, manufacture and use
US2464094A (en) Process for the amidation of esters
US2096749A (en) Derivatives of alkylolamine condensation products
US2260384A (en) Hydroxy-alkyl amine condensation products
US2372797A (en) Condensation products
US2132388A (en) Aliphatic acid diamide of long chain aliphatic diamines and process of making the same
US2328021A (en) Derivatives of amines
US2290881A (en) Halogeno-carboxylic amides
US2329619A (en) mu-substituted oxazolines, mu-substituted pentoxazolines, and methods for their preparation
US2386445A (en) Composition of matter
US2190133A (en) Quaternary ammonium derivatives of alcohol amine compounds
US2304830A (en) Amides of heterocyclic carboxylic acids
US4302354A (en) Mixtures of vicinal aminoalkanols, process of preparation, and their application as corrosion inhibitors
US2486249A (en) Acylamino-nu-substituted amides
US2383859A (en) Capillary active agents
US2277016A (en) Preparation of organic compounds
US2324712A (en) Dialkyl esters of n-substituted aspartic acid and method of preparing the same
US2343071A (en) Amino fatty acid derivatives and their manufacture
CA1259630A (en) Alkanolamine salts of alkenyl succinic acid dialkyl semiamide corrosion inhibitors