US2593413A - Fatty ackd-alkoxypolyglycol ali - Google Patents

Fatty ackd-alkoxypolyglycol ali Download PDF

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US2593413A
US2593413A US2593413DA US2593413A US 2593413 A US2593413 A US 2593413A US 2593413D A US2593413D A US 2593413DA US 2593413 A US2593413 A US 2593413A
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alkoxypolyglycol
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molecular weight
fatty acid
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/19—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a saturated carbon skeleton containing rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
    • B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
    • B01F23/40—Mixing liquids with liquids; Emulsifying
    • B01F23/41—Emulsifying
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
    • Y10S516/914—The agent contains organic compound containing nitrogen, except if present solely as NH4+
    • Y10S516/915—The compound contains -C[=O]NHH where substitution may be made for the hydrogen
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
    • Y10S516/914—The agent contains organic compound containing nitrogen, except if present solely as NH4+
    • Y10S516/916—The compound contains repeating -OCnH2n-, i.e. repeating unsubstituted oxyalkylene

Definitions

  • the present invention relates to surface active agents and process for manufacturing the same; and it particularly relates to such agents having particular utility as wetting agents, detergents and emulsifying agents in the textile assistant field.
  • a high molecular weight fatty acid having 8 to 24 carbon atoms is combined at a temperature belowr135 C. and desirably between 100 C.-130 0., first with an alkoxypolyglycol at 100 C.-120 0., and then the combination of fatty acid and alkoxypolyglycol is combined with a primary or a secondary aliphatic amine, preferably either a water soluble alkanolamine or a water soluble polyalkylene polyamine
  • the second step is desirably carried out at atemperature of 10 to 150 C. higher than the temperature employed in the first step, as for example 115 to 130 C.
  • the resulting product is a highly complex mixture of alkoxypolyglycol esters and amino esters. This'complex may be neutralized or acidified, if
  • lower aliphatic acids such as formic, acetic or lactic.
  • the complex may also be treated with alkylafting agents, such as diethyl or dimethyl sulfate 2 pound of each class is necessary for the manufacture of the products described herein.
  • alkylafting agents such as diethyl or dimethyl sulfate 2 pound of each class is necessary for the manufacture of the products described herein.
  • Class 1.--F'atty acids having from 8 to 24 carbon atoms.
  • the saturated fatty acids" C10 to C1; (namely, capric, lauric, myristic, palmitic and stearic) are preferred, but other fatty acids including unsaturated and hydroxylated types may be used.
  • Mixed fatty acids obtained from splitting natural oils and fats, such as coconut oil and palm kernel oil, may also be employed.
  • Mono and diethanolamine Mono and dipropanolamine Z-methyl, Z-amino, l-propanol; Aminoethylethanolamine Triethylene tetramine; and Tetraethylene pentamine.
  • a fatty acid (one mol) and an alkoxypolyglycol to mol) are heated together with an acid catalyst, such as butyl naphthalene sulfonic acid at a temperature of C. to C. for one-half to two hours, or until such time that all the alkoxypolyglycol has been reacted.
  • an acid catalyst such as butyl naphthalene sulfonic acid
  • an aliphatic amine to 1 mols is added slowly with agitation and the temperature is increased to the range of 120 to C.
  • the mixture is then held at this temperature for two to four hours, or until such time as the free fatty acid content of the mixture is from 10% to 20%.
  • the mixture usually becomes alkaline due to the addition of the amine.
  • the addition of a small amount of caustic soda or other alkali is desirable at the start to insure the neutralization of the acid catalyst used in the first step and to impart a definite degree of alkalinity in the second step.
  • a higher proportion of the alkoxypolyglycol is used in the first step, a lower proportion of the amine may be used in the second step and vice versa.
  • Emm-ple 1 200 parts (1 mol) of lauric acid and 175 parts mol) of a methoxy polyethylene glycol having an average molecular weight of 350 are heated in the presence of an alkylated aromatic sulfonic acid (one to two parts by weight) at 110 to 120 C. for about one hour or until the alkoxypolyglycol has been completely reacted. Then the temperature is raised to 120 to 130 C.
  • the resulting composition when cooled to room temperature, consists of an amber viscous liquid which is useful as a wetting agent and detergent in textile wet processing operations.
  • Palmitic acid 258 parts (approx. 1 mol) Methoxy polyethylene glycol having an average molecular weight of 750, 200 parts (approx. of a mol)
  • Second step Second step:
  • a process of making a surface active agent which comprises successively combining a high molecular weight fatty acid having 10 to 18 carbon atoms with an alkoxypolyglycol and with an aliphatic saturated amine selected from the group consisting of primary and secondary water-soluble aliphatic amines at a temperature under 135 .C.
  • a process of making a surface active agent which comprises successively combining a high molecular weight fatty acid having 10 to 18 carbon atoms with an alkoxypolyglycol at a temperature in the range of C. to C. and with an aliphatic saturated amine selected from the group consisting ofprimary and secondary watersoluble aliphatic amines at a higher temperature in the range of 120 C. to C.
  • a process of making a surface active agent which comprises successively combining a high molecular weight fatty acid having 10 to 18 carbon atoms with an alkoxylpolyglycol having a molecular weight of 200 to 1,000 and with an aliphatic saturated amine selected from the group consisting of primary and secondary water-rsolus ble aliphatic amines.
  • a process of making a surface active agent which comprises successively combining one .mol of a high molecular weight fatty acid havinglO to 18 carbon atoms with a; to /2 mol ofan alkoxypolyglycol and then with to 1% molsof an aliphatic saturated amine selected from the group consisting of primary and secondary watersoluble aliphatic amines.
  • a process of making a surface activeagent which comprises successively combining a high molecular weight fatty acid having 10 to 18 carbon atoms with an alkoxypolyglycol at 110 C. to 120 C. for /2 to 2 hours and then with an aliephatic saturated amine selected from the group consisting of primary and secondary water-soluble aliphatic amines at 120 C. to 130 C. for '2 to 4 hours.
  • a process of making a surface active agent which comprises successively combining a high molecular weight fatty acid having 10 to 18 car'- bon atoms with an alkoxypolyglycol and then with an ethanolamine selected from the group consisting of mon-ethanolamine and di-ethanolamine.
  • a process of making a surface active agent which comprises successively combining a high molecular weight fatty acid having 10 to 18 carbon atoms with a m-ethoxy polyethylene glycol and then with a polyalkylenepolyamine.
  • An emulsifying and wetting agent and detergent consisting of the complex reaction products of a combination of a high molecular weight fatty acid having 10 to 18 carbon atoms, an alkoxypolyglycol and an aliphatic saturated amine selected from the group consisting of primary and secondary water-soluble aliphatic amines.
  • An emulsifying and wetting agent. and de-'- tergent consisting of the complex reaction prod ucts of a combination of a high molecular Weight fatty acid having 10 to 18 carbon atoms and .a
  • a process of preparing surface active agents which comprises heating about 1 mol of a fatty acid having '8 to 24 carbon atoms with mol of an alkoxypolyethy lene glycol having a molecular weight ofabjout 200 to 1000 at 110 C. to 120 C. for about one hour and then reacting the combination with about 1.1 mol of an alkanolamine at 115 C. to 130 C. for about two hours.

Description

Patented Apr. 22, 1952 FATTY ACID-ALKOXYPOLYGLYCOL ALL. PHATIO AMINE COMBINATIONS USEFUL AS TEXTILE SURFACE AGENTS Alton A. Cook, Glen Ridge, and Ira Sapers, New- Y ark, N. J., assignors to Arkansas Company, 1110.,
Newark, N. J a corporation of New York No Drawing. Application December 20, 1949, Serial No. 134,150
Claims.
The present invention relates to surface active agents and process for manufacturing the same; and it particularly relates to such agents having particular utility as wetting agents, detergents and emulsifying agents in the textile assistant field.
i It is among the objects of the present invention to provide a novel procedure and novel combinations by such procedure'which at low cost will give a high yield of unusually eiiective detergent, wetting and emulsifying agents particularly useful in the textile field, but also useful in the leather, metal working and other allied fields.
Still further objects and advantages will appear in the more detailed description set forth below, it being understood, however, that this more detailed description is given by way of illustration and explanation only, and not by way of limitation, since various changes may be made therein bythose skilled in the art without departing from the scope and spirit of the present invention.
In the preferred procedure, a high molecular weight fatty acid having 8 to 24 carbon atoms is combined at a temperature belowr135 C. and desirably between 100 C.-130 0., first with an alkoxypolyglycol at 100 C.-120 0., and then the combination of fatty acid and alkoxypolyglycol is combined with a primary or a secondary aliphatic amine, preferably either a water soluble alkanolamine or a water soluble polyalkylene polyamine The second step is desirably carried out at atemperature of 10 to 150 C. higher than the temperature employed in the first step, as for example 115 to 130 C.
The resulting product is a highly complex mixture of alkoxypolyglycol esters and amino esters. This'complex may be neutralized or acidified, if
desired, with lower aliphatic acids, such as formic, acetic or lactic.
l ,The complex may also be treated with alkylafting agents, such as diethyl or dimethyl sulfate 2 pound of each class is necessary for the manufacture of the products described herein.
Class 1.--F'atty acids having from 8 to 24 carbon atoms. The saturated fatty acids" C10 to C1; (namely, capric, lauric, myristic, palmitic and stearic) are preferred, but other fatty acids including unsaturated and hydroxylated types may be used. Mixed fatty acids obtained from splitting natural oils and fats, such as coconut oil and palm kernel oil, may also be employed.
' Class 2.--Water-soluble aliphatic saturated alkoxypolyglycols having over four carbon atoms, one hydroxy "group and a molecular weight of 200 to 1,000 The alkoxy group may have from one to four carbon atoms. 1
Examples:
Mono and diethanolamine Mono and dipropanolamine Z-methyl, Z-amino, l-propanol; Aminoethylethanolamine Triethylene tetramine; and Tetraethylene pentamine.
aver- In the preferred procedure for producing surface active agents, in the first step a fatty acid (one mol) and an alkoxypolyglycol to mol) are heated together with an acid catalyst, such as butyl naphthalene sulfonic acid at a temperature of C. to C. for one-half to two hours, or until such time that all the alkoxypolyglycol has been reacted.
In the second step, an aliphatic amine to 1 mols) is added slowly with agitation and the temperature is increased to the range of 120 to C. The mixture is then held at this temperature for two to four hours, or until such time as the free fatty acid content of the mixture is from 10% to 20%. During this step, the mixture usually becomes alkaline due to the addition of the amine. In some cases, the addition of a small amount of caustic soda or other alkali is desirable at the start to insure the neutralization of the acid catalyst used in the first step and to impart a definite degree of alkalinity in the second step. In general, if a higher proportion of the alkoxypolyglycol is used in the first step, a lower proportion of the amine may be used in the second step and vice versa.
To give some typical examples of the preferred combinations and procedure involving the reaction of the fatty acid and the alkoxypolyglycol in the first step followed by further reacting this product with a water soluble aliphatic saturated primary and secondary amine (all parts being by weight) Emm-ple 1 200 parts (1 mol) of lauric acid and 175 parts mol) of a methoxy polyethylene glycol having an average molecular weight of 350 are heated in the presence of an alkylated aromatic sulfonic acid (one to two parts by weight) at 110 to 120 C. for about one hour or until the alkoxypolyglycol has been completely reacted. Then the temperature is raised to 120 to 130 C. and 115 parts (1.1 mols) of diethanolamine are added slowly and the temperature maintained for about two hours or until the free fatty acid is reduced to about 10%. The resulting composition, when cooled to room temperature, consists of an amber viscous liquid which is useful as a wetting agent and detergent in textile wet processing operations.
.In-the following examples, the proportions are given below and the procedure in all .cases is similar to that described above:
Example 2 Eirst...step: Myristic acid, 228 parts (1 mol).
Methoxy polyethylene glycolhaving an average molecular Weight of 550, 185 parts (approx. of a mol) Second step:
Aminoethylethanolamine, '10 parts of a mol) Example 3 First step:
Coconut fatty acids, 210 parts (approx. one
mol)
Ethoxy polyethylene glycol having an average molecular weight of 560. 280 parts /2 of a mol) Second step:
Diethanolamine, 35 parts /3 of a mol) Monoethanclamine, 61 parts ('l-mo'l) Example 4 First step:
Capric acid, 172 parts (1 mol) Propoxy polyethylene glycol having an average molecular weight of 380, 195 parts /2 of 2. mol) Second step:
Triethylene tetramine, '73 parts of a mol) Example First step:
Palmitic acid, 258 parts (approx. 1 mol) Methoxy polyethylene glycol having an average molecular weight of 750, 200 parts (approx. of a mol) Second step:
Die'thanolamine, 150 parts (approx. 1.4 mols) Sincecertainchanges may be made in the above textile assistants and process for manufacturing the same and differentembodiments of the inveniii tion could be made without departing from the scope thereof, it is intended that all matter contained in the above .description shall be interpreted as illustrative and not in a limiting sense.
Having now particularly described and acertained the nature of the invention, and in what manner the same is to be performed, what is claimed is:
1. A process of making a surface active agent which comprises successively combining a high molecular weight fatty acid having 10 to 18 carbon atoms with an alkoxypolyglycol and with an aliphatic saturated amine selected from the group consisting of primary and secondary water-soluble aliphatic amines at a temperature under 135 .C.
2. .A process of making a surface active agent which comprises successively combining a high molecular weight fatty acid having 10 to 18 carbon atoms with an alkoxypolyglycol at a temperature in the range of C. to C. and with an aliphatic saturated amine selected from the group consisting ofprimary and secondary watersoluble aliphatic amines at a higher temperature in the range of 120 C. to C.
3. A process of making a surface active agent which comprises successively combining a high molecular weight fatty acid having 10 to 18 carbon atoms with an alkoxylpolyglycol having a molecular weight of 200 to 1,000 and with an aliphatic saturated amine selected from the group consisting of primary and secondary water-rsolus ble aliphatic amines.
4. A process of making a surface active agent which comprises successively combining one .mol of a high molecular weight fatty acid havinglO to 18 carbon atoms with a; to /2 mol ofan alkoxypolyglycol and then with to 1% molsof an aliphatic saturated amine selected from the group consisting of primary and secondary watersoluble aliphatic amines.
5. A process of making a surface activeagent which comprises successively combining a high molecular weight fatty acid having 10 to 18 carbon atoms with an alkoxypolyglycol at 110 C. to 120 C. for /2 to 2 hours and then with an aliephatic saturated amine selected from the group consisting of primary and secondary water-soluble aliphatic amines at 120 C. to 130 C. for '2 to 4 hours.
6. A process of making a surface active agent which comprises successively combining a high molecular weight fatty acid having 10 to 18 car'- bon atoms with an alkoxypolyglycol and then with an ethanolamine selected from the group consisting of mon-ethanolamine and di-ethanolamine.
7. A process of making a surface active agent which comprises successively combining a high molecular weight fatty acid having 10 to 18 carbon atoms with a m-ethoxy polyethylene glycol and then with a polyalkylenepolyamine.
8. An emulsifying and wetting agent and detergent consisting of the complex reaction products of a combination of a high molecular weight fatty acid having 10 to 18 carbon atoms, an alkoxypolyglycol and an aliphatic saturated amine selected from the group consisting of primary and secondary water-soluble aliphatic amines. v
,9. An emulsifying and wetting agent. and de-'- tergent consisting of the complex reaction prod ucts of a combination of a high molecular Weight fatty acid having 10 to 18 carbon atoms and .a
methoxy polyethylene glycol with an aliphatic saturated amine selected from the group consisting of primary and secondary water-soluble aliphatic amines. v
10. A process of preparing surface active agents which comprises heating about 1 mol of a fatty acid having '8 to 24 carbon atoms with mol of an alkoxypolyethy lene glycol having a molecular weight ofabjout 200 to 1000 at 110 C. to 120 C. for about one hour and then reacting the combination with about 1.1 mol of an alkanolamine at 115 C. to 130 C. for about two hours.
" ALTON A. COOK.
IRA SAPERS.
8 REFERENCES CITED UNITED STATES PATENTS Name Date Cook et a1 Dec. 20, 1949

Claims (1)

1. A PROCESS OF MAKING A SURFACE ACTIVE AGENT WHICH COMPRISES SUCCESSIVELY COMBINING A HIGH MOLECULAR WEIGHT FATTY ACID HAVING 10 TO 18 CARBON ATOMS WITH AN ALKOXYPOLGLYCOL AND WITH AN ALIPHATIC SATURATED AMINE SELECTED FROM THE GROUP CONSISTING OF PRIMARY AND SECONDARY WATER-SOLUBLE ALIPHATIC AMINES AT A TEMPERATURE UNDER 135*C.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4085126A (en) * 1976-09-17 1978-04-18 Ashland Oil, Inc. Fatty alkanolamide detergent compositions
US4092253A (en) * 1975-09-04 1978-05-30 Hoechst Aktiengesellschaft Fabric softeners
US4129506A (en) * 1975-09-04 1978-12-12 Hoechst Aktiengesellschaft Fabric softeners
US4634450A (en) * 1983-07-06 1987-01-06 Bergvik Kemi Ab Coal-water dispersion

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2491478A (en) * 1947-05-12 1949-12-20 Arkansas Company Inc Polyalcohol-fatty acid-aliphatic amine combinations useful as textile assistants andprocess of producing the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2491478A (en) * 1947-05-12 1949-12-20 Arkansas Company Inc Polyalcohol-fatty acid-aliphatic amine combinations useful as textile assistants andprocess of producing the same

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4092253A (en) * 1975-09-04 1978-05-30 Hoechst Aktiengesellschaft Fabric softeners
US4129506A (en) * 1975-09-04 1978-12-12 Hoechst Aktiengesellschaft Fabric softeners
US4085126A (en) * 1976-09-17 1978-04-18 Ashland Oil, Inc. Fatty alkanolamide detergent compositions
US4634450A (en) * 1983-07-06 1987-01-06 Bergvik Kemi Ab Coal-water dispersion

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