US2659731A - Cakbocyclic monocarboxyijc acid - Google Patents

Cakbocyclic monocarboxyijc acid Download PDF

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US2659731A
US2659731A US2659731DA US2659731A US 2659731 A US2659731 A US 2659731A US 2659731D A US2659731D A US 2659731DA US 2659731 A US2659731 A US 2659731A
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glyoxalidine
hydroxyethyl
heptadecenyl
foam
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    • 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
    • C07D233/14—Radicals substituted by oxygen atoms
    • 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
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/07—Organic amine, amide, or n-base containing

Definitions

  • This invention relates to new compounds, more particularly to compounds having the general formula where X is the negative radical of a carbocyclic monocarboxy acid, R is a higher aliphatic hydrocarbon radical containing at least 11, preferably 1'7 carbon atoms in an acyclic chain, R is hydrogen or a lower aliphatic group containing not more than 6 carbon atoms, Y i hydrogen or a lower aliphatic group containing not more than 6 carbon atoms, and Z is hydrogen or a lower alkyl group containing not more than six carbon atoms.
  • These compounds may also be described generally as carbocyclic monocarboxy acid salts of glyoxalidines.
  • carbocyclic monocarboxy acid salts of glyoxalidines are viscous liquids or soft greases which are characterized by being soluble or dispersible in water. They are easily prepared by mixing the carbocyclic carboxy acid with the glyoxalidine in equimolecular proportions in the cold or by warming the two together at temperatures up to 100 degrees C. for to 15 minutes.
  • benzoic acid 4-chlorobenzoic acid, 2,4-dichlorobenzoic acid, salicylic acid, cinnamic acid, 3,5- dinitrobenzoic acid, 2-nitrobenzoic acid, 3-nitrobenzoic acid, ortho cresotinic acid, anthranilic acid, phenylacetic acid, Z-chlorobenzoic acid, 4-chlorobenz0ic acid, phenoxyacetic, 2,4-dichlorophenoxyacetic acid, 2,4,5-trichlorophenoxyacetic acid, pentachlorophenoxyacetic acid, naphthenic acids and 2,4-dichlorobenzoic acid.
  • glyoxalidines that may be reacted with any of the foregoing acids in preparing these salts are: l-(2-aminoethyD-2 -heptadecenyl glyoxalidine, 1-(2 -hydroxyethyl)-2- heptadecenyl glyoxalidine, 4-methyl-2-heptadecenyl glyoxalidine, 1 [2 -(2 aminoethyl) aminoethyl] -2-heptadecenyl glyoxalidine, 1-( 2- aminoethyD-2-undecyl glyoxalidine, 1-(2-hydroxyethyD-2-undecyl glyoxalidine, 4-methy1- 2-undecyl glyoxalidine, 1 -[2 -(2 aminoethyl) aminoethyl] 2 undecyl glyoxalidine, 1 (2 aminoe
  • the naphthenic acid which has been designated 235 XX Socony Vacuum is a fully refined naphthenic acid having a neutralization equivalent of 235.
  • the solubility test of the glyoxalidine salt in water was conducted by adding one drop of the salt to 10 ml. of Water and agitating and observing the resulting solution.
  • the solubility of the glyoxalidine salt in oil was determined by addin one drop of the salt to 10 ml. of an aromatic oil such as the catalytically cracked product marketed by Shell Oil Company under the trade name of Shells medium aromatic oil with a boiling range of 430 degrees F. to 620 degrees F. and a flash point of 225 degrees F. (Cleveland open cup).
  • an aromatic oil such as the catalytically cracked product marketed by Shell Oil Company under the trade name of Shells medium aromatic oil with a boiling range of 430 degrees F. to 620 degrees F. and a flash point of 225 degrees F. (Cleveland open cup).
  • glyoxalidine salts have shown themselves to be very excellent emulsifying agents for aromatic oils in water. Emulsifying tests were conducted as follows: One half gram of the slyoxalidine salt was dissolved in grams of the Shell medium aromatic oil described above. To this 450 m1. of water was added with agitation. The stability of the resulting emulsion was judged by the amount of time required for the oil to start to come out of solution. In some cases no separation of oil occurred, but a cream layer of emulsion rich in oil was noticed to float to the top. The time was noted when this separation could be noticed.
  • the salts of this invention are outstanding emulsifying agents. Whereas relatively large amounts (over 5% and up to 25%) of the other emulsifying agents such as, polyoxyalkylene esters and ethers, petroleum sulphonates, alkyl aryl sulphonates, alkyl sulphates are required to emulsify Shell medium aromatic oil in water,
  • glyoxalidine salts of this invention are required to give emulsions stable for long periods.
  • Example II Ten grams of Chlordane was dissolved in 89 grams of kerosene and 1 gram of the glyoxalidine Very stable emulsions of insecticides such as Chlordane, DDT, and Methoxychlor can be made using these glyoxalidine salts.
  • Example III Five (5) grams of DDT was dissolved in 93 grams of Shell medium aromatic oil and 2 grams of the l-(z-hydroxyethyl)-2-heptadecenyl glyoxalidine benzoate described above was added. Ten milliliters of the above oil was mixed with 90 m1. of water. The resulting emulsion was stable about fifteen minutes. Under the same conditions 4 grams of the stearate salt of the same glyoxalidine gave an emulsion that was stable about 6 minutes.
  • glyoxalidine salts In addition to their ability to emulsify oils in water these glyoxalidine salts show other very interesting properties. Dilute (1%) aqueous solutions are extremely viscous such as in the case of the 2,4-dichlorophenoxyacetic acid, salicyclic acid, anthranilic acid, 2,4-dichlorobenzoic acid, orthochlorobenzoic acid, para-chlorobenzoic acid, and cinnamic acid salts of 1-(2-hydroxyethyl) -2-heptadecenyl glyoxalidine. Where emulsifying agents and thickening agents are needed in the same composition these compounds are very useful.
  • the substituted glyoxalidines themselves have the ability to thicken water olutions but the herein described carbocyclic carboxy acid salts are markedly superior in this respect.
  • carbocyclic monocarboxy acid as used herein is intended to cover any monocarboxylic acid containing a carbocyclic ring.
  • the carboxy group may be linked directly to a carbon atom of the carbocyclic ring or may be connected to a side alkyl or alkylene group.
  • a compound having the following general formula where X is the negative radical of a carbocyclic monocarboxy acid from the group consisting of monoand di-carbocyclic acids in which the carbocyclic structure is from the group consisting of 5-membered and G-membered carbon rings, R is a higher aliphatic hydrocarbon radical containing at least 11 carbon atoms, R and Y are from the group consisting of hydrogen and lower aliphatic groups containing not more than 6 carbon atoms and Z is from the group consisting of hydrogen and lower alkyl groups containing not more than 6 carbon atoms.
  • Carbocyclic monocarboxy acid addition salts of 2-heptadecenyl glyoxalidines from the group consisting of the monoand dicarbocyclic monocarboxylic acid addition salts of 2-heptaclecenyl glyoxalidines wherein the carbocyclic structures consist of fi-membered rings.

Description

Patented Nov. 17, 1953 CARBOCYCLIC MONOCARBOXYLIC ACID SALTS OF GLYOXALIDINES George W. Luvisi, Chicago, 111., assignor to National Aluminate Corporation, Chicago, 111., a corporation of Delaware No Drawing. Application September 26, 1950, Serial No. 186,929
9 Claims.
1 This invention relates to new compounds, more particularly to compounds having the general formula where X is the negative radical of a carbocyclic monocarboxy acid, R is a higher aliphatic hydrocarbon radical containing at least 11, preferably 1'7 carbon atoms in an acyclic chain, R is hydrogen or a lower aliphatic group containing not more than 6 carbon atoms, Y i hydrogen or a lower aliphatic group containing not more than 6 carbon atoms, and Z is hydrogen or a lower alkyl group containing not more than six carbon atoms. These compounds may also be described generally as carbocyclic monocarboxy acid salts of glyoxalidines.
These carbocyclic monocarboxy acid salts of glyoxalidines are viscous liquids or soft greases which are characterized by being soluble or dispersible in water. They are easily prepared by mixing the carbocyclic carboxy acid with the glyoxalidine in equimolecular proportions in the cold or by warming the two together at temperatures up to 100 degrees C. for to 15 minutes.
As examples of carboxy acids that may be used to prepare these salts there may be mentioned:
benzoic acid, 4-chlorobenzoic acid, 2,4-dichlorobenzoic acid, salicylic acid, cinnamic acid, 3,5- dinitrobenzoic acid, 2-nitrobenzoic acid, 3-nitrobenzoic acid, ortho cresotinic acid, anthranilic acid, phenylacetic acid, Z-chlorobenzoic acid, 4-chlorobenz0ic acid, phenoxyacetic, 2,4-dichlorophenoxyacetic acid, 2,4,5-trichlorophenoxyacetic acid, pentachlorophenoxyacetic acid, naphthenic acids and 2,4-dichlorobenzoic acid.
Examples of glyoxalidines that may be reacted with any of the foregoing acids in preparing these salts are: l-(2-aminoethyD-2 -heptadecenyl glyoxalidine, 1-(2 -hydroxyethyl)-2- heptadecenyl glyoxalidine, 4-methyl-2-heptadecenyl glyoxalidine, 1 [2 -(2 aminoethyl) aminoethyl] -2-heptadecenyl glyoxalidine, 1-( 2- aminoethyD-2-undecyl glyoxalidine, 1-(2-hydroxyethyD-2-undecyl glyoxalidine, 4-methy1- 2-undecyl glyoxalidine, 1 -[2 -(2 aminoethyl) aminoethyl] 2 undecyl glyoxalidine, 1 (2 aminoethyl)-2-tridecyl glyoxalidine, 1-(2-hydroxyethyD-2-tridecyl glyoxalidine, 4-methyl-2- tridecyl glyoxalidine, 1-[2-(2-aminoethyll-ami- 2 noethyll-Z-tridecyl glyoxalidine, 1-(2-aminoethyl) -2-pentadecyl glyoxalidine, 1-(2-hydroxyethyl) -2-pentadecyl glyoxalidine, 4-methyl-2- pentadecyl glyoxalidine and 1-[2-(2-aminoethyl) -aminoethyll 2-pentadecyl glyoxalidine.
The following is a table containing some of the properties of some of the glyoxalidine salts that have been prepared in accordance with the invention.
The naphthenic acid which has been designated 235 XX Socony Vacuum is a fully refined naphthenic acid having a neutralization equivalent of 235.
The solubility test of the glyoxalidine salt in water was conducted by adding one drop of the salt to 10 ml. of Water and agitating and observing the resulting solution.
The solubility of the glyoxalidine salt in oil was determined by addin one drop of the salt to 10 ml. of an aromatic oil such as the catalytically cracked product marketed by Shell Oil Company under the trade name of Shells medium aromatic oil with a boiling range of 430 degrees F. to 620 degrees F. and a flash point of 225 degrees F. (Cleveland open cup).
These glyoxalidine salts have shown themselves to be very excellent emulsifying agents for aromatic oils in water. Emulsifying tests were conducted as follows: One half gram of the slyoxalidine salt was dissolved in grams of the Shell medium aromatic oil described above. To this 450 m1. of water was added with agitation. The stability of the resulting emulsion Was judged by the amount of time required for the oil to start to come out of solution. In some cases no separation of oil occurred, but a cream layer of emulsion rich in oil was noticed to float to the top. The time was noted when this separation could be noticed. The various salts of 2- heptadecenyl-4-methyl glyoxalidine and 1-[2- (2 aminoethyl) aminoethyl] 2 heptadecenyl glyoxalidineszgere tested at 2% concentration in the oil. Control tests using aliphatic carboxylic acid salts of glyoxalidines such as the acetic acid and oleic acid salts of l-(2-hydroxyethyl)- Z-heptadecenyl glyoxalidine were inefiective in forming emulsions of this oil even when used at the concentration of 5% in the aromatic oil.
The salts of this invention are outstanding emulsifying agents. Whereas relatively large amounts (over 5% and up to 25%) of the other emulsifying agents such as, polyoxyalkylene esters and ethers, petroleum sulphonates, alkyl aryl sulphonates, alkyl sulphates are required to emulsify Shell medium aromatic oil in water,
1% or even less of the glyoxalidine salts of this invention are required to give emulsions stable for long periods.
decenyl glyoxalidine salicylate gave an emulsion which was stable for one hour when mixed with 900 ml. of water. When 5.0 grams of the Solubility Reactants Weight Description Solubility in water in aroratio matic oil 1 (2 hydroxyethyl) 2 e heptadec- 3. 5
enyl glyoxalidine. Homogeneous viscous liquid Cloudy solution; very viscous; Soluble. 2,4-diclilorophenoxy acetic acid 2. 2 foams copiously. 1 (2 hydroxyethyl) 2 heptadec- 3. 5
enyl glyoxalidine. .-do Slightly cloudy; foams copi- Do. Salicylic acid 1. 38 ously; very viscous. 1 (2 hydroxyethyl) 2 heptadec- 3. 5
cnyl glyoxalidine do Clear solution; foams copi- Do. Benzoic acid l. 22 ously; viscous. 2 heptadceenyl 4 3. 2
dine. Homogeneous brown viscous liquid. Milky solution; fairly heavy Do. 2,4-diehlorophenoxy acetic acid 2. 2 foam. ifgffig ggfi glyoxan g }Homogeneous yellow viscous liquid. Clear gelatinous solution; Do. 1 2 2 aminoethyl) am oethylla. as heavy 2-lieptadeccnyl-glyoxalidine. Homogeneous amber viscous liquid. Clear solution; very heavy Insoluble. 2,4-dichloroplienoxy acetic acid 2. 2 foam. 1 ggg i igfig g 93 Homogeneous deep yellow viscous Clear gelatinous solution; Do. salicylic acid L 38 liquid. very heavy foam. figggg g ff glyoxahdme' Clear brown viscous liquid Disperses in water; some Soluble.
081]". ll ggfig gfigi gg 4'methy1 oxandme' 3 Clear amber viscous liquid Turbid solution; fairly heavy Insoluble. l-[2-(2-aminoethyl)-aminoethyl1-2- 3.93 foam heptadecenyl glyoxalidinc. Cloudy amber tally-like liquid Clear solution; very heavy Do. 2,i-dichloro-phenoxyacetic acid 4. 4 foam. l-[2-aminoethyl)-arninocthyl]-2-hepta- 3. 93
dccenyl glyoxalidine. i Clear s lution; extremely D0. Salicylic acid 2. 76 heavy foam. l-(2-hydroxyethyl)-2-heptadccenyl 3.
glyoxalid e. Viscous liquid Clear solution; some foam Soluble. Phcnylacetic acid 1. 36 l-(2-hydroxyethyl)-2-heptadecenyl 3. 5
glyoxalidine. Resinous-like paste Hazy solution; some foani Do. Beta hydroxy naphthoic acid 1. 88 l-(2-hydroxyethyl)-2-heptadecenyl 3. 5
glyoxalidine. Viscous liquid Hazy solution; some foam; Do. Ortho cresotinic acid 1. 52 slightly viscous. l-(2-hydroxyethyl)-2-heptadecenyl 3. 5
glyoxalidine. Tan opaque viscous liquid Hazy solution; some foam S l i g h t 1y 2,4,5-trichloro-phenoxyacetic acid 2. 55 azy sol-(2-hydroxyethyl)-2-heptadecenyl 3. 5 lution.
glyoxalidine. Brown clear viscous liquid Milky solution; fair amount Clear solu- Pentacblorophenoxy-acetic acid 3. 23 of foam; slightly viscous. 0nl-(2-hydroi yethyl)-2-heptadecenyl 3. 5
glyoxalidine. Resinous paste Clear solution; lots of foam; Soluble. Anthranilic acid 1. 37 very viscous. 1-(2-hydroxyethyl)-2-heptadecenyl 3. 5
glyoxalidine. Viscous oil Clear solution; fair amount of Do. ;2,4 dlchlorobenzoic acid 1. 91 foam; extremely viscous. l-(2-hydroxyethyl)-2-heptadecenyl 3. 5
glyoxalidincs. Res ious-like paste Clear solution; some foam Insoluble. Para aminophenyl acetic acid l. 51 l-(2-hydroxyethyl)-2-heptadecenyl 3. 5
glyoxalidine. Res ous Solid Slightly soluble; lots of foam D0. Gallic acid 1.7 l-(2-hydroxyethyl) -2-hep ta deccnyl glyoxalidine 3. 5 Homogeneous viscous liquid Clear solution; slightly vis- Soluble. 3,5-dinitrobenzoic acid 2. 12 cons; lots of foam. l-(2-hydroxyethyl) -2-hep tadecenyl glyoxalidine 3. 5 Viscous Oil Hazy solution; quite viscous; Do. 2,5-dichlorosalicylic acid 2.07 lots of foam. l-(z-hydroxyethyl) -2-heptadecenyl glyoxalidine 3. 5 -d0 Clear solution; viscous; some Do. Ortho chlorobenzoic acid 1. 57 foam. l-(Z-hydroxyethyl) -2-hepta decenyl glyoxalidine 3. 5 Waxy pas e Hazy solution; viscous; some Do. Para chlorobenzoic acid 1. 57 foam. l-(2hydroxyethyl) -2-hep tadecenyl glyoxalidine 3. 5 Taffy-like viscous oil Clear solution; lots of foam- Disperses Para-hydroxyphenyl glycine 1. 67 in l-(2-hydroxyethyl) -2-heptadecenyl alid' 3. 5 oft grease Hazy solution; very viscous; Soluble.
1. 48 little foam. l-(2-hydroxyethyl) glyoxalidine 3. 5 Wax-like solid Clear solution; lots of foam.. Disperses Hippuric acid 1. 79 in oi l-(2-liydrpxyethyl) ggmfig iaa'z g' i' 2 5 V cous O l Hazy solution; quite a bit of Soluble. 2 1y ii i'i' "'iii'i'i ""121 g5 foam.
epta 9 y g yoxa 1 Light brown viscous liquid..- Clear solution; extremely vis- Do Cinnamic acid 43 cons; some {0mm glyoxalidine stearate salt was used the emulsion broke in 10 minutes. One gram of the 1-(2-hydroxyethyl) -2-heptadeceny1 glyoxalidine cinnamate salt substituted for the salicylate salt gave an emulsion that was stable for 72 minutes. The acetate salt even with up to 5 grams gave an emulsion that was stable for less than 2 minutes.
Example II Ten grams of Chlordane was dissolved in 89 grams of kerosene and 1 gram of the glyoxalidine Very stable emulsions of insecticides such as Chlordane, DDT, and Methoxychlor can be made using these glyoxalidine salts.
The emulsifying properties of these new compounds will be further illustrated by the following examples.
Earample I Twenty (20) grams of Methoxychlor dissolved in 79.5 grams of Shell medium aromatic oil containing 0.5 gram of 1-(2-hydroxyethyl) -2-hepta- 75 salicylate salt described above was added. When 10 ml. of this mixture was added to 90 ml. of water, the resulting emulsion was stable about 19 minutes. When prepared with 1 gram of the stearate salt of the same glyoxalidine the Chlordane emulsion broke in minutes. Four (4) grams of the stearate salt gave an emulsion that was stable about 11 minutes.
Example III Five (5) grams of DDT was dissolved in 93 grams of Shell medium aromatic oil and 2 grams of the l-(z-hydroxyethyl)-2-heptadecenyl glyoxalidine benzoate described above was added. Ten milliliters of the above oil was mixed with 90 m1. of water. The resulting emulsion was stable about fifteen minutes. Under the same conditions 4 grams of the stearate salt of the same glyoxalidine gave an emulsion that was stable about 6 minutes.
In addition to their ability to emulsify oils in water these glyoxalidine salts show other very interesting properties. Dilute (1%) aqueous solutions are extremely viscous such as in the case of the 2,4-dichlorophenoxyacetic acid, salicyclic acid, anthranilic acid, 2,4-dichlorobenzoic acid, orthochlorobenzoic acid, para-chlorobenzoic acid, and cinnamic acid salts of 1-(2-hydroxyethyl) -2-heptadecenyl glyoxalidine. Where emulsifying agents and thickening agents are needed in the same composition these compounds are very useful. The substituted glyoxalidines themselves have the ability to thicken water olutions but the herein described carbocyclic carboxy acid salts are markedly superior in this respect.
The term carbocyclic monocarboxy acid as used herein is intended to cover any monocarboxylic acid containing a carbocyclic ring. The carboxy group may be linked directly to a carbon atom of the carbocyclic ring or may be connected to a side alkyl or alkylene group.
The invention is hereby claimed as follows:
1. A compound having the following general formula Where X is the negative radical of a carbocyclic monocarboxy acid from the group consisting of monoand di-carbocyclic acids in which the carbocyclic structure is from the group consisting of 5-membered and G-membered carbon rings, R is a higher aliphatic hydrocarbon radical containing at least 11 carbon atoms, R and Y are from the group consisting of hydrogen and lower aliphatic groups containing not more than 6 carbon atoms and Z is from the group consisting of hydrogen and lower alkyl groups containing not more than 6 carbon atoms.
2. Carbocyclic monocarboxy acid addition salts of 2-heptadecenyl glyoxalidines from the group consisting of the monoand dicarbocyclic monocarboxylic acid addition salts of 2-heptaclecenyl glyoxalidines wherein the carbocyclic structures consist of fi-membered rings.
3. The 2,4-dichlorophenoxyacetic acid addition salt of 1-(2-hydroxyethyl)-2-heptacleceny1 glyoxalidine.
4. The salicyclic acid addition salt of 1-(2-hydroxyethyl) -2-heptadecenyl glyoxalidine.
5. The cinnamic acid salt of l-(2-hydroxyethyl) -2-heptadecenyl glyoxalidine.
6. The benzoic acid salt of 1-(2-hydroxyethyl) -2-heptadecenyl glyoxalidine.
7. The anthranilic acid salt of 1-(2-hydroxyethyl) -2-heptadecenyl glyoxalidine.
8. The carbocyclic monocarboxy acid addition salts of glyoxalidines substituted in the 2 position with a higher aliphatic acyclic hydrocarbon group containing 11 to 17 carbon atoms wherein the monocarboxy acid salt-forming group is derived from an acid from the group consisting of 2,4-dichlorophenoxyacetic acid, salicylic acid, 2,4-dichlorobenzoic acid, 3,5-dinitrobenzoic acid, 4-chlorobenzoic acid and cinnamic acid.
9. The carbocyclic monocarboxy acid addition salts of 2-heptadecenyl glyoxalidines wherein the monocarboxy salt-forming group is derived from an acid from the group consisting of 2,4- dichlorophenoxyacetic acid, salicylic acid, 2,4- dichlorobenzoic acid, 3,5-dinitrobenzoic acid, 4- chlorobenzoic acid and cinnamic acid.
GEORGE W. LUVISI.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,267,965 Wilson Dec. 30, 1941 2,268,273 Wilkes Dec. 30, 1941 2,374,354 Kaplan Apr. 24, 1945

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2773879A (en) * 1952-04-02 1956-12-11 Nat Aluminate Corp Glyoxalidine salts of long chain dicarboxylic acids
US2824059A (en) * 1954-02-08 1958-02-18 Nat Aluminate Corp Corrosion inhibitor composition and method of preventing corrosion
US3186912A (en) * 1959-08-03 1965-06-01 Robert L Beamer Cosmetic emulsion
US3313825A (en) * 1961-07-25 1967-04-11 Geigy Chem Corp Certain imidazoline salts
US5151220A (en) * 1990-08-07 1992-09-29 Nalco Chemical Company Chemical abatement of carbonate cracking

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2268273A (en) * 1939-05-27 1941-12-30 Carbide & Carbon Chem Corp Textile finishing
US2267965A (en) * 1939-07-18 1941-12-30 Carbide & Carbon Chem Corp Hydroxyalkyl glyoxalidines
US2374354A (en) * 1942-01-13 1945-04-24 Richards Chemical Works Imidazolines

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2268273A (en) * 1939-05-27 1941-12-30 Carbide & Carbon Chem Corp Textile finishing
US2267965A (en) * 1939-07-18 1941-12-30 Carbide & Carbon Chem Corp Hydroxyalkyl glyoxalidines
US2374354A (en) * 1942-01-13 1945-04-24 Richards Chemical Works Imidazolines

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2773879A (en) * 1952-04-02 1956-12-11 Nat Aluminate Corp Glyoxalidine salts of long chain dicarboxylic acids
US2824059A (en) * 1954-02-08 1958-02-18 Nat Aluminate Corp Corrosion inhibitor composition and method of preventing corrosion
US3186912A (en) * 1959-08-03 1965-06-01 Robert L Beamer Cosmetic emulsion
US3313825A (en) * 1961-07-25 1967-04-11 Geigy Chem Corp Certain imidazoline salts
US5151220A (en) * 1990-08-07 1992-09-29 Nalco Chemical Company Chemical abatement of carbonate cracking

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