GB772223A - Improvements in imidazolinepropionates in the forms of metal salts, acid addition salts, and free acids, and preparation thereof - Google Patents

Improvements in imidazolinepropionates in the forms of metal salts, acid addition salts, and free acids, and preparation thereof

Info

Publication number
GB772223A
GB772223A GB29671/55A GB2967155A GB772223A GB 772223 A GB772223 A GB 772223A GB 29671/55 A GB29671/55 A GB 29671/55A GB 2967155 A GB2967155 A GB 2967155A GB 772223 A GB772223 A GB 772223A
Authority
GB
United Kingdom
Prior art keywords
imidazoline
methyl
hydrolysed
imidazolines
hydrogen
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
GB29671/55A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB772223A publication Critical patent/GB772223A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

The invention comprises imidazolines of the formula <FORM:0772223/IV(b)/1> where R is a hydrocarbon radical, R1 is hydrogen or methyl and M is hydrogen or an equivalent of a metal, and their addition salts with strong inorganic acids. These are made by reacting the corresponding 1-unsubstituted imidazolines with b -propiolactone, acrylonitrile or an alkyl acrylate, and in the latter cases hydrolysing the product to the free acid with aqueous alkali. Suitable temperatures are 75-150 DEG C. in the case of the ester and 100-175 DEG C. for the lactone. The radical R is preferably an aliphatic group of 9-17 carbon atoms, and may be the residue of, e.g., tall oil acids which comprise a mixture of long-chain alkyl and rosin residues. Examples show the reactions of (1) 2-heptadecyl-imidazoline and methyl acrylate, and product hydrolysed; (2) heptadecyl-4-methyl-imidazoline and methyl acrylate (hydrolysed); (3) 2-undecyl-imidazoline and methyl acrylate (hydrolysed), propiolactone, and acrylonitrile (hydrolysed); (4) 2-undecyl-4-methyl-imidazoline and methyl acrylate (hydrolysed); (5) 2-nonyl-imidazoline and methyl or ethyl acrylate (hydrolysed); (6) 2-heptadecenyl-imidazoline and methyl or butyl acrylate (hydrolysed); (7) 2-(tall oil residue)-imidazoline and methyl acrylate (hydrolysed). The products may be obtained as sodium salts, free zwitter ions or hydrochlorides. 2-Substituted-imidazolines of the formula <FORM:0772223/IV(b)/2> are made by condensing 1 : 2-alkylene diamines with carboxylic acids or their salts or halides. Examples are given of the preparation of 2-undecyl-imidazoline, 2-nonyl-imidazoline, 2-heptadecenyl-imidazoline, 2-(tall oil residue)-imidazoline and 2-undecyl-4-methyl-imidazoline. The acid RCOOH may also be octyl-, nonyl- or dodecyl-benzoic acid.ALSO:Imidazolines of the formula <FORM:0772223/III/1> where R is a hydrocarbon radical, R1 is hydrogen or methyl and M is hydrogen or an equivalent of a metal, and their addition salts with strong inorganic acids, are surface-active cleansing agents effective in acid and alkaline solution. They may be mixed with alkaline builders e.g. sodium carbonate or metasilicate, and/or with anion-active soaps and detergents. The resulting compositions may be used in the form of bars powders, pastes or solutions. Suitable imidazolines are mentioned.ALSO:Bactericidal compositions comprise quaternary ammonium salts and imidazolines of the formula <FORM:0772223/VI/1> where R is a hydrocarbon radical, R1 is hydrogen or methyl and M is hydrogen or an equivalent of a metal, or their addition salts with strong inorganic acids. The ratio of quaternary salt to imidazoline may be 1:1 to 5:1 by weight. A typical composition is octylphenoxyethoxyethyl - dimethyl-benzyl-ammonium chloride and the sodium salt of 2 - undecyl - 1 - (b - carboxyethyl) - imidazoline. Other quaternary salts that may be used are dodecyl-trimethyl-ammonium chloride, dodecyl-dimethyl-benzyl-ammonium chloride, cetyl-pyridinium bromide and dodecylbenzyl-trimethyl-ammonium chloride. Other suitable imidazolines are mentioned.
GB29671/55A 1954-10-26 1955-10-18 Improvements in imidazolinepropionates in the forms of metal salts, acid addition salts, and free acids, and preparation thereof Expired GB772223A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US772223XA 1954-10-26 1954-10-26

Publications (1)

Publication Number Publication Date
GB772223A true GB772223A (en) 1957-04-10

Family

ID=22136778

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29671/55A Expired GB772223A (en) 1954-10-26 1955-10-18 Improvements in imidazolinepropionates in the forms of metal salts, acid addition salts, and free acids, and preparation thereof

Country Status (1)

Country Link
GB (1) GB772223A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3231582A (en) * 1965-02-04 1966-01-25 Hans S Mannheimer Imidazolinium derivatives
US3231581A (en) * 1966-01-25 Imidazglinium derivatives
US3231580A (en) * 1961-06-30 1966-01-25 Hans S Mannheimer Substituted imidazolines

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3231581A (en) * 1966-01-25 Imidazglinium derivatives
US3231580A (en) * 1961-06-30 1966-01-25 Hans S Mannheimer Substituted imidazolines
US3231582A (en) * 1965-02-04 1966-01-25 Hans S Mannheimer Imidazolinium derivatives

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