US3412155A - Fatty branched amine dioxides - Google Patents

Fatty branched amine dioxides Download PDF

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US3412155A
US3412155A US487606A US48760665A US3412155A US 3412155 A US3412155 A US 3412155A US 487606 A US487606 A US 487606A US 48760665 A US48760665 A US 48760665A US 3412155 A US3412155 A US 3412155A
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dioxide
dioxides
fatty
amine
gms
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US487606A
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Jr Eugene J Miller
Mais Ago
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Armour Industrial Chemical Co
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Priority to GB42812/65A priority patent/GB1064188A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • C07C291/04—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds containing amino-oxide bonds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/75—Amino oxides

Definitions

  • This invention relates to novel derivatives of fatty acid and more particularly to a novel class of fatty amine dioxides which are particularly useful as detergents for dishwashin-g.
  • an object of this invention is to provide novel difunctional fatty compounds which are especially useful as detergents.
  • Another object is to provide a novel class of fatty amine dioxides.
  • Still another object is to provide novel methods for the manufacture of such fatty amine dioxides.
  • a further object is to provide a novel class of compounds which are good detergents especially in dishwashing machines.
  • the invention accordingly comprises the several steps and the relation of one or more of such steps with respect to each of the others, and the compound possessing the features, properties, and the relation of elements, which are exemplified in the following detailed disclosure, and the scope of the invention will be indicated in the claims.
  • a novel class of fatty amine dioxides may be prepared by oxidizing the fatty amine precursor with a strong oxidizing agent. For example, by reacting N,N,N,N-tetramethylaminomethylstearylamine with hydrogen peroxide, N,N,N,N-tetramethylaminomethylstearylamine dioxide is obtained. Or, by reacting ethoxylated aminomethylstearylamine with hydrogen peroxide, its dioxide will be obtained.
  • N,N,N,N-tetramethylaminomethylstearylamine dioxide A 250 ml., three neck flask, equipped with a magnetic stirrer, thermometer, addition funnel and reflux condenser is charged with N,N,N',N-tetramethylarninomethylstearylamine (17.2 gms., 0.0485 mole) and 15 gms. aqueous isopropanol. Hydrogen peroxide (8.2 gms., 45.5% aqueous, 0.11 mole) is added dropwise at 30-45 C. over a period of thirty-five minutes. The reaction mixture is stirred overnight at about 30 C. resulting in a colorless solution.
  • EXAMPLE II Ethoxylated aminomethylstearylamine dioxide
  • a 250 ml., three neck flask, equipped with a magnetic stirrer, thermometer, addition funnel and condenser is charged with 57.4 gms. (0.102 mole, 0.204 equivalent) of ethoxylated aminomethylstearylarnine (Neutralization Equivalent 282), 17.6 gms. of water and 30.5 gms. of isopropanol.
  • Hydrogen peroxide (16.9 gms., 0.244 mole, 49% active) is then added dropwise over a period of four hours at 3045 C.
  • the reaction mixture is then allowed to stir at room temperature for an additional 67 hours.
  • An amber solution will be obtained having the following analysis:
  • EXAMPLE III Ethoxylated aminostearylamine dioxide A 250 ml., three neck flask, equipped with a magnetic stirrer, thermometer, addition funnel and condenser is charged with 92.1 gms. (0.181 mole, 0.362 equivalent) of ethoxylated aminostearylamine (Neutralization Equivalent 254), 26.5 gms. of water and 49.1 gms. of isopropanol. Hydrogen peroxide (30.2 gms., 0.435 mole, 49% active) is then added dropwise over a period of four hours at 3045 C. The reaction mixture is then stirred at room temperature for an additional 70 hours. An amber solution will be obtained having the following analysis:
  • aminofatty amines that may be treated in accordance with the method of this invention, those falling within the following formula are operable:
  • aminoethylcaprylylamine aminoethylcaprylylamine, aminoethylcapyrylamine, aminoethyllaurylamine, aminoethylmyristylamine, aminoethylpalmitylamine, aminoethylstearylamine, aminoethylarachidylamine, aminoethylbehenylamine, aminoethyllignocerylamine or mixtures thereof such as derivable from natural fats and oils, such as tallow, soybean oil and coconut oil; the alkoxylated (ethoxylated and propoxylated) derivatives of aminocaprylylamine, aminocaprylamine, aminolaurylamine, aminoimyristylamine, aminopalrnitylamine, aminostearylamine, aminoarachidylamine, aminobehenylamine, aminolignocerylamine, aminolmethylcaprylylamine, aminomethylcaprylamine, aminomethyllaurylamine, aminomethylmyristylamine, aminomethylpalrnity
  • the strong oxidizing agent that is useful falls within a relatively wide scope of compounds. Among such are hydrogen peroxide, perbenzoic acid and Cards acid.
  • an alkoxylated amine When an alkoxylated amine is utilized, it may have been alkoxylated with from 4 to 200 moles of an alkylene oxide, such as ethylene oxide, or propylene oxide.
  • an alkylene oxide such as ethylene oxide, or propylene oxide.
  • fatty amine dioxides that may be formed by the method of this invention are those which fall within the following formula:
  • aminoethylcaprylamine dioxide aminoethyllaurylamine dioxide, aminoethylmyristylamine dioxide, aminoethylpalmitylamine dioxide, aminoethylstearylamine dioxide, aminoethylarachidylamine dioxide, aminoethylbehenylamine dioxide, aminoethyllignocerylamine dioxide or mixtures thereof such as derivable from natural fats and oils, such as tallow, soybean oil and coconut oil; and ethoxylated or propoxylated (4 to 200 moles) of aminocaprylylamine dioxide, aminocaprylamine dioxide, aminolaurylamine dioxide, aminomyristylarnine dioxde, aminopalmitylamine dioxide, aminostearylamine dioxide, aminoarachidylamine dioxide, aminobehenylamine dioxide, aminolignocerylamine dioxide, aminomethylcaprylylamine dioxide, aminomethylcaprylamine dioxide, aminomethyllaurylamine, dioxide, aminomethylmyristylamine dioxide, aminomethylpalrnity
  • the above compounds are useful as surfactants and especially as dishwashing detergents.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
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Description

United States Patent 3,412,155 FATTY BRANCHED AMINE DIOXIDES Eugene J. Miller, Jr., Wheaton, and Ago Mais, La
Grange Park, Ill., assignors, by mesne assignments,
to Armour Industrial Chemical Company, a corporation of Delaware No Drawing. Continuation-impart of application Ser. No. 402,921, Oct. 9, 1964. This application Sept. 15, 1965, Ser. No. 487,606
7 Claims. (Cl. 260-583) ABSTRACT OF THE DISCLOSURE Fatty branched amine dioxides made by oxidizing the fatty diamine precursor with a strong oxidizing agent such as H 0 These are useful as detergents.
This application is a continuation-in-part application of Ser. No. 402,921 filed Oct. 9, 1964, now abandoned.
This invention relates to novel derivatives of fatty acid and more particularly to a novel class of fatty amine dioxides which are particularly useful as detergents for dishwashin-g.
Roe and Swern of the U.S. Department of Agriculture, in the Journal of the American Oil Chemists Society periodical, volume 37, pages 661 to 668 (1960) report that unsaturated fatty acids may be carboxylated with carbon monoxide. The monoxide adds to the double bond to create a long chain fatty acid with two or more reactive groups therein. With two or more reactive groups, the fatty compound not only has good hydrophobic characteristics, but also has high potency as a detergent with the proper reactive groups in place of the carboxy group. Unfortunately, no further work was apparently done by Roe and Swern or others along this line.
Accordingly, an object of this invention is to provide novel difunctional fatty compounds which are especially useful as detergents.
Another object is to provide a novel class of fatty amine dioxides.
Still another object is to provide novel methods for the manufacture of such fatty amine dioxides.
A further object is to provide a novel class of compounds which are good detergents especially in dishwashing machines.
Other objects of the invention will in part be obvious and will in part appear hereinafter.
The invention accordingly comprises the several steps and the relation of one or more of such steps with respect to each of the others, and the compound possessing the features, properties, and the relation of elements, which are exemplified in the following detailed disclosure, and the scope of the invention will be indicated in the claims.
It has now been found that a novel class of fatty amine dioxides may be prepared by oxidizing the fatty amine precursor with a strong oxidizing agent. For example, by reacting N,N,N,N-tetramethylaminomethylstearylamine with hydrogen peroxide, N,N,N,N-tetramethylaminomethylstearylamine dioxide is obtained. Or, by reacting ethoxylated aminomethylstearylamine with hydrogen peroxide, its dioxide will be obtained.
Reference is now made to the following examples which illustrate the synthesis of a particular fatty amine dioxide:
EXAMPLE I N,N,N,N-tetramethylaminomethylstearylamine dioxide A 250 ml., three neck flask, equipped with a magnetic stirrer, thermometer, addition funnel and reflux condenser is charged with N,N,N',N-tetramethylarninomethylstearylamine (17.2 gms., 0.0485 mole) and 15 gms. aqueous isopropanol. Hydrogen peroxide (8.2 gms., 45.5% aqueous, 0.11 mole) is added dropwise at 30-45 C. over a period of thirty-five minutes. The reaction mixture is stirred overnight at about 30 C. resulting in a colorless solution.
Analysis.Amine oxide, 43.6%; free amine, 2%; free peroxide, 3.26%.
EXAMPLE II Ethoxylated aminomethylstearylamine dioxide A 250 ml., three neck flask, equipped with a magnetic stirrer, thermometer, addition funnel and condenser is charged with 57.4 gms. (0.102 mole, 0.204 equivalent) of ethoxylated aminomethylstearylarnine (Neutralization Equivalent 282), 17.6 gms. of water and 30.5 gms. of isopropanol. Hydrogen peroxide (16.9 gms., 0.244 mole, 49% active) is then added dropwise over a period of four hours at 3045 C. The reaction mixture is then allowed to stir at room temperature for an additional 67 hours. An amber solution will be obtained having the following analysis:
Analysis.-Amine oxide, 48.5%; free amine, nil; free peroxide, 0.36%.
EXAMPLE III Ethoxylated aminostearylamine dioxide A 250 ml., three neck flask, equipped with a magnetic stirrer, thermometer, addition funnel and condenser is charged with 92.1 gms. (0.181 mole, 0.362 equivalent) of ethoxylated aminostearylamine (Neutralization Equivalent 254), 26.5 gms. of water and 49.1 gms. of isopropanol. Hydrogen peroxide (30.2 gms., 0.435 mole, 49% active) is then added dropwise over a period of four hours at 3045 C. The reaction mixture is then stirred at room temperature for an additional 70 hours. An amber solution will be obtained having the following analysis:
Analysis-Amine oxide, 50.7%; free amine, nil; free peroxide, 0.11%.
Among the aminofatty amines that may be treated in accordance with the method of this invention, those falling within the following formula are operable:
and mixtures thereof A=H--, CH a, b, c, and d=1 to 50 x+y=6 to 22 2:0 to 2.
Among specific compounds falling within the above formula are the N,N,N,N'-tetrarnethyl derivatives of ammocaprylylamine, aminocaprylamine, aminolaurylamine, amiuomyristylamine, aminopalmitylaimine, aminostearylamine, aminoarachidylamine, aminobehenylamine, aminolignocerylamine, aminomethylcaprylylamine, aminomethylcaprylamine, aminomethyllaurylamine, aminomethylmyristylamine, aminomethylpalrnitylarnine, aminomethylstearylamine, aminomethylarachidylamine, aminomethylbehenylamine, aminomethyllignocerylamine,
aminoethylcaprylylamine, aminoethylcapyrylamine, aminoethyllaurylamine, aminoethylmyristylamine, aminoethylpalmitylamine, aminoethylstearylamine, aminoethylarachidylamine, aminoethylbehenylamine, aminoethyllignocerylamine or mixtures thereof such as derivable from natural fats and oils, such as tallow, soybean oil and coconut oil; the alkoxylated (ethoxylated and propoxylated) derivatives of aminocaprylylamine, aminocaprylamine, aminolaurylamine, aminoimyristylamine, aminopalrnitylamine, aminostearylamine, aminoarachidylamine, aminobehenylamine, aminolignocerylamine, aminolmethylcaprylylamine, aminomethylcaprylamine, aminomethyllaurylamine, aminomethylmyristylamine, aminomethylpalrnitylamine, aminomethylstearylamine, aminomethylarachidylamine, aminornethylbehenylamine, aminomethyllignocerylamine, aminoethylcaprylylamine, aminoethylcaprylamine, aminoethyllaurylamine, aminothylmyristylamine, aminoethylpalmitylamine, aminoethylstearylamine, aminoethylarachidylamine, aminoethylbehenylamine, aminoethylignocerylamine or mixtures thereof such as derivable from natural fats and oils, such as tallow, soybean oil and coconut oil.
The strong oxidizing agent that is useful, falls within a relatively wide scope of compounds. Among such are hydrogen peroxide, perbenzoic acid and Cards acid.
Usually between 2.0 to 20.0 molar equivalent percent in excess of the fatty amine utilized is used, and the preferred excess amount is 5.0 molar equivalent percent.
When an alkoxylated amine is utilized, it may have been alkoxylated with from 4 to 200 moles of an alkylene oxide, such as ethylene oxide, or propylene oxide.
The fatty amine dioxides that may be formed by the method of this invention are those which fall within the following formula:
and mixtures thereof A=H-, CH a, b, c, and d=1 to 50 x+y=6 to 22 2:0 to 2 Among compounds which fall within the above formula are the N,N,N',N'-tetrame'thyl derivatives of aminocaprylylamine dioxide, aminocaprylamine dioxide, aminolaurylamine dioxide, aminomyristylamine dioxide, aminopalmitylamine dioxide, aminostearylamine dioxide, aminoarachidylamine dioxide, aminobehenylamine dioxide, aminolignocerylamine dioxide, a'minomethylcaprylylamine dioxide, aminomethylcaprylarrfine dioxide, aminomethyllaurylamine dioxide, aminomethylmyristylamine dioxide, aminornethylpalmitylamine dioxide, aminomethylstearylamine dioxide, aminomethylarachidylamine dioxide, aminomethylbehenylamine dioxide, aminomethyllignocerylamine dioxide, aminoethylcaprylylamine dioxide,
4 aminoethylcaprylamine dioxide, aminoethyllaurylamine dioxide, aminoethylmyristylamine dioxide, aminoethylpalmitylamine dioxide, aminoethylstearylamine dioxide, aminoethylarachidylamine dioxide, aminoethylbehenylamine dioxide, aminoethyllignocerylamine dioxide or mixtures thereof such as derivable from natural fats and oils, such as tallow, soybean oil and coconut oil; and ethoxylated or propoxylated (4 to 200 moles) of aminocaprylylamine dioxide, aminocaprylamine dioxide, aminolaurylamine dioxide, aminomyristylarnine dioxde, aminopalmitylamine dioxide, aminostearylamine dioxide, aminoarachidylamine dioxide, aminobehenylamine dioxide, aminolignocerylamine dioxide, aminomethylcaprylylamine dioxide, aminomethylcaprylamine dioxide, aminomethyllaurylamine, dioxide, aminomethylmyristylamine dioxide, aminomethylpalrnitylamine dioxide, aminomethylstearylamine dioxide, aminomethylarachidylamine dioxide, aminomethylbehenylamine dioxide, aminomethyllignocerylamine dioxide, aminoethylcaprylylamine dioxide, aminoethylcaprylamine dioxide, aminoethyllaurylamine dioxide, aminoethylmyristylamine dioxide, aminoethylpalmitylamine dioxide, aminoethylstearylamine dioxide, aminoethylarachidylamine dioxide, aminoethylbehenylamine dioxide, aminoethyllignooerylamine dioxide or mixtures thereof such as derivable from natural fats and oils, such as tallow, soybean oil and coconut oil.
The above compounds are useful as surfactants and especially as dishwashing detergents.
It will thus be seen that the objects set forth above, among those made apparent from the preceding description, are efficiently attained and, since certain changes may be made in carrying out the above method and in the compounds set forth without departing from the scope of the invention, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.
It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention, which, as a matter of language, might be said to fall therebetween.
Now that the invention has been described, what is claimed as new and desired to be secured by Letters Patent is:
1. The fatty amine dioxide falling within the following formula:
and mixtures thereof A=H, CH
a, b, c, and d=1 to 50 x+y=6 to 22 z= to 2 2. N,N,N',N'-tetramethy1aminomethylstearylamine dioxide.
3. N,N,N,N'-tetramethylaminoundecylamine dioxide.
4. A mixture of N,N,N',N'-tetramethylamino1methylfattyamine dioxides the fatty constituent being derived from the natural fats and oils.
5. A mixture of N,N,N',N-tetramethylaminomethylfattyamine dioxides the fatty constituent being derived from tallow.
6. The alkoxylated aminomethylstearylamine dioxides falling within the following formula:
7. The alkoxylated aminostearylamine dioxides falling within the following formula:
A ,(HCHaOhH CH (OH;) ,-oH*(cH,),,-N o
(CHCHl0)bH A A it. H(0H CH( J).1N(( JHCH O)dH 8 where A=H-, GH a, b, c, d=1 to x+y=6 to 22 References Cited UNITED STATES PATENTS OTHER REFERENCES Jerchel et al.: Chemical Abstracts, vol. 48, page 1246e-h (1954).
CHARLES B. PARKER, Primary Examiner.
R. L. RAYMOND, Assistant Examiner.
US487606A 1964-10-09 1965-09-15 Fatty branched amine dioxides Expired - Lifetime US3412155A (en)

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Application Number Priority Date Filing Date Title
CA785805A CA785805A (en) 1964-10-09 Derivatives of fatty acids
US487606A US3412155A (en) 1964-10-09 1965-09-15 Fatty branched amine dioxides
FR34093A FR1449388A (en) 1964-10-09 1965-10-07 New fatty acid derivatives and process for their preparation
GB42812/65A GB1064188A (en) 1964-10-09 1965-10-08 Fatty amine dioxides

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US40292164A 1964-10-09 1964-10-09
US487606A US3412155A (en) 1964-10-09 1965-09-15 Fatty branched amine dioxides

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531526A (en) * 1966-12-21 1970-09-29 Procter & Gamble Diamine dioxide detergent compounds
US3975443A (en) * 1972-06-06 1976-08-17 Allen & Hanburys Limited 1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine
US4548744A (en) * 1983-07-22 1985-10-22 Connor Daniel S Ethoxylated amine oxides having clay soil removal/anti-redeposition properties useful in detergent compositions
US5844029A (en) * 1995-09-25 1998-12-01 General Electric Company Polymer compositions containing hydrocarbon amine oxide and hydrocarbon amine oxide stabilizer compositions
US5866718A (en) * 1997-03-20 1999-02-02 General Electric Company Synthesis of tertiary amine oxides

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3145735A1 (en) * 1981-11-19 1983-05-26 Hoechst Ag, 6230 Frankfurt TRIAMINE TRIOXIDES, METHOD FOR THE PRODUCTION THEREOF AND CLEANING AGENTS CONTAINING THEM

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3197509A (en) * 1961-12-21 1965-07-27 Procter & Gamble Diamine dioxide compounds
US3202714A (en) * 1961-12-04 1965-08-24 Procter & Gamble Oxy containing tertiary amine oxides
US3270060A (en) * 1963-04-22 1966-08-30 Millmaster Ouyx Corp Amine oxides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3202714A (en) * 1961-12-04 1965-08-24 Procter & Gamble Oxy containing tertiary amine oxides
US3197509A (en) * 1961-12-21 1965-07-27 Procter & Gamble Diamine dioxide compounds
US3270060A (en) * 1963-04-22 1966-08-30 Millmaster Ouyx Corp Amine oxides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3531526A (en) * 1966-12-21 1970-09-29 Procter & Gamble Diamine dioxide detergent compounds
US3975443A (en) * 1972-06-06 1976-08-17 Allen & Hanburys Limited 1-(3,4-dichlorobenzamidomethyl)-cyclohexyldimethylamine
US4548744A (en) * 1983-07-22 1985-10-22 Connor Daniel S Ethoxylated amine oxides having clay soil removal/anti-redeposition properties useful in detergent compositions
US5844029A (en) * 1995-09-25 1998-12-01 General Electric Company Polymer compositions containing hydrocarbon amine oxide and hydrocarbon amine oxide stabilizer compositions
US5880191A (en) * 1995-09-25 1999-03-09 General Electric Company Polymer compositions containing hydrocarbon amine oxides and hydrocarbon amine oxide stabilizer compositions
US5866718A (en) * 1997-03-20 1999-02-02 General Electric Company Synthesis of tertiary amine oxides
US5955633A (en) * 1997-03-20 1999-09-21 General Electric Company Synthesis of tertiary amine oxides

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GB1064188A (en) 1967-04-05
CA785805A (en) 1968-05-21

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