US2267965A - Hydroxyalkyl glyoxalidines - Google Patents
Hydroxyalkyl glyoxalidines Download PDFInfo
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- US2267965A US2267965A US285081A US28508139A US2267965A US 2267965 A US2267965 A US 2267965A US 285081 A US285081 A US 285081A US 28508139 A US28508139 A US 28508139A US 2267965 A US2267965 A US 2267965A
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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
- C07D233/16—Radicals substituted by nitrogen atoms
Definitions
- This invention relates to the production of certain glyoxalidines, or dihydroimidazoles (imidazolines), to wit, those containing alkyl side chains and including at least one hydroxyalkyl side chain. More specifically, the invention comprises the condensation of fatty acid compounds having from 10 to carbon atoms in the molecule, or mixtures of these, with hydroxyalkyl alkylene polyamines to produce substituted glyoxalidines- While it is possible by this process to obtain the tetrasubstituted glyoxalidines, this invention is particularly concerned with the production of the 1,2-disubstituted and the 1,2,4 or
- the new compounds are characterized as being either high-boiling viscous liquids, or lowmelting, waxy solids and by being highly polar andstrongly basic. They are colloidally dispersible in cold water, giving rise to viscous solutions, and they are completely soluble in acids, such as dilute hydrochloric acid.
- the glyoxalidine compounds of this invention may be used for various purposes, and it has been found that they are especially valuable as emulsifying agents, detergents, wetting, softening and scouring agents, and for other uses where their properties of surface activity can be employed.
- the new substances, and their salts and soaps, when used as emulsifying agents, are particularly emicacious'for producing stable dispersions of mineral oils, or other oleaginous substances and water.
- the new substances are also valuable as softening and finishing agents for textiles, according to processes set forth in application Serial No. 276,122, filed May 27, 1939, by B. G. Wilkes and A. L. Wilson, and as assistants in dyeing textiles to improve the fastness and other qualities of the dyeing operation.
- the production of the substituted glyoxalidines of this invention may be accomplished by dehydrating fatty acid amides of various hydroxyalkyl alkylene polyamines and their substitution products, or, more generally stated, by heating, at temperatures between about 120C. and about 300 0., these amines with free fatty acids, fatty acid esters or amides under such conditions as to effect the splitting out of water in excess of 1.5 mols for each mol of free fatty acid and in excess of 0.5 mol for each mol of combined fatty acid involved.
- amines examples include hydroxyethyl ethylene diamine, hydroxyisopropyl propylene diamine, hydroxyethyl diethylene triamine hydroxyethyl triethylene tetramine, as well as similar hydroxyalkyl alkylene polyamines.
- the hydroxyalkyl alkylene polyamines of this invention are of the 1,2 series, that is, at least one amino group and one imino group are attached to adjacent carbon atoms.
- alkylene polyamine is also defined as including products containing more than one alkylene group.
- Fatty acid compounds that may be used in the production of the glyoxalidines may include the fatty acids themselves, such as lauric, oieic, linoleic, ricinoleic, stearic and palmitic acids, as well as their salts and esters.
- Other fatty acids and their salts and esters naturally occurring in such vegetable oils as olive, cocoanut, linseed and cottonseed oils, which have 10 to 20 carbon atoms in their molecule, may also be employed.
- the substituted glyoxalidines of this invention may be regarded as dehydration products of substituted ethylene diamines and fatty acids, or their salts and esters.
- the formation of the glyoxalidine or imidazoline ring from these substances may be considered as a two-step reaction involving, first, the formation of an amide and a molecule of water, and, second, the dehydration of this amide to yield a substituted glyoxalidine and a second molecule of water.
- a fatty acid such as oleic acid
- It represents an aliphatic radical con i compounds, are represented by the following gentaining from to 20 carbon'ratoms and being theresidue of a higher fatty acid; R1 represents hydrogen or a lower alkyl group; andRz represents an alkylene group, a lower alkyl substituted alkylene group, or ,a radical of the structure CHR1.CHR1 (NH.CHR1'.CHRI1) 12- where R1 remains hydrogen or a lower alkyl group and a: is an integer.
- liquids examples include benzene, xylene, toluene, diisopropyl ether, ethyl acetate. ethylene dichloride, and carbon tetrachloride. If a diluent is used in carrying out the reaction, lower temperatures and lower molar ratios of hydroxyalkyl alkylene polyamine may be used and high yields of the desired glyoxalidine obtained nevertheless. This characteristic is illustrated in Example V.
- the substituted glyoxalidines contain a reactive hydroxy group, it is possible to form esters of these compounds by the reaction of organic acids with the free alcoholic group. Be cause the glyoxalidine compounds are basic, it is possible to form salts or soaps of these compounds by their addition with various acidic substances. including both mineral and organic acids, such as hydrochloric, sulfuric, acetic, ethyl hexoic, and lauric acids. such salts or soaps the solubility of these compounds is enhanced.
- Quaternary ammonium compounds may also be formed by warming the substituted glyoxalidines with the appropriate reagents, such..as diethyl sulfate, dimethyl sulfate, benzyl chloride and the like. These compounds are usually viscous liquids to wax-like bodies, characterized by their nearly neutral reaction and by their ready solubility in water. These quaternary compounds are perhaps less useful as emulsifying agents and as textile fin- By the formation of,
- R, R1, and R2 are as indicated in the above formula
- Y represents an organic or inorganic radical
- R3 is hydrogen, or an alkyl or aralkyl group.
- Example I One mol of beta-hydroxyethyl ethylene diamine was mixed with 0.5 mol of commercial oleic acid and heated under reflux for 5 hours until a final temperature of about 270 C. was reached. About 2 mols of water per mol of oleic acid were distilled off during this period. Excess hydroxyethyl ethylene diamine was then removed, and the product, 1-hydroxyethyl-2-heptadecenyl glyoxalidine, was purified by vacuum distillation. This substance was found to be a straw-colored, heavy, viscous liquid, with a specific gravity of 0.935 at 20/20 C. and a boiling point from about 230 to 240 C. at an absolute pressure of 1 mm. of mercury.
- This glyoxalidine is particularly useful for dispersing mineral oils in water and in producing water scourable mineral oils for use as textile lubricants.
- Example II One and one-half mols of hydroxyethyl ethylene diamine were mixed with one mol of stearic acid and heated, in the presence of xylene, under reflux for 8 hours at a temperature of from C. to C. About 1.5 mols of water per mol of stearic acid were distilled oil! as a constant boiling mixture with the xylene during this period. Excess amine and xylene were then removed, and the product, 1-hydroxyethyl-2-heptadecyl glyoxalidine, was purified by vacuum distillation. This substance was a light-colored solid, insoluble in water, melting at 45 to 55 C.,
- This product is es- I pecially valuable as a softening and finishing agent for regenerated cellulose fabrics, cotton, and similar fibrous materials and as an assistant in dyeing textiles to improve the fastness and substantivity. It is also useful where surface.
- lameness v 3 agent It is also very useful as adetergent being 1 molar quantities of the reactants used in each unaffected in its action by hard water, or by dilute salt water or even by acid solutio
- adetergent being 1 molar quantities of the reactants used in each unaffected in its action by hard water, or by dilute salt water or even by acid solutio
- Two mols of hydroxyethyl ethylene cliamine were mixed with one mol of cocoanut fatty acids and heated for 3 hours at a temperature of from 170 C. to 270 C. During this period 1.8 mols of water were distilled off. Excess amine was removed and the product, l-hydroxyethyl-2-undecyl glyoxalidine, was purified by vacuum distillation.
- This compound may be prepared by reacting propylene diamine, having the structure H:C.CH.CH:.NH:
- Example V No. l norylene No. 2 xylene present present Hy ethyl ethylene dinmine My pm" 104 104 Oleio acid -.do--.. 282 282 xylene do.-.. None 91 Time oi reactio 5 Final temperature. ...C 310 205 Water removed .parts.
- alkylene hydrocarbon group is of the group consisting of an alkylene hydrocarbon group, a lower alkyl substituted alkylene hydrocarbon group, and a radical of the structure CHR1.CH R1 (NH.CHR1.CHR1) 1- where a: is an integer.
- l-hydroxyethyl-Z- heptadecenyl glyoxaldine being characterized as a viscous liquid, completely soluble in dilute hydrochloric acid, and boiling from about 230 to 8.
- Process for making substituted glyoxalidines which comprises heating a mixture containing a free hydroxyalkyl alkylene poiyamine of the 1, 2 series and at least one of group consisting of free fatty acids containing from 10 to 20 carbon atoms, amides of said acids, and esters of said acids, at temperatures between about*120 and about 300 C., and removing water continuously from said mixture during said heating, the temperature and the duration of said heating being so correlated as to cause the splitting out of. water in excess of 1.5 mols for each mol of free fatty acid and in excess of 0.5 moi for each moi of combined fatty acid involved.
- the temperature and the duration of said heating being so correlated as to cause the splitting out of water in excess of 1.5 mole for each moi of fatty acid involved.
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Description
Patented Dec. 30, 1941 2,267,965 nrpnoxraurrr. GLYOXALIDINES Alexander L. Wilson, Sharpsburg, Carbide and Carbon Chemicals corporation of New York No Drawing. Application Pa., assignor to Corporation, a
July 18, 1939,"
Serial No. 285,081
9 Claims.
This application is a continuation-in-part of my-copending application Serial No. 191,191, flied February 18, 1938.
This invention relates to the production of certain glyoxalidines, or dihydroimidazoles (imidazolines), to wit, those containing alkyl side chains and including at least one hydroxyalkyl side chain. More specifically, the invention comprises the condensation of fatty acid compounds having from 10 to carbon atoms in the molecule, or mixtures of these, with hydroxyalkyl alkylene polyamines to produce substituted glyoxalidines- While it is possible by this process to obtain the tetrasubstituted glyoxalidines, this invention is particularly concerned with the production of the 1,2-disubstituted and the 1,2,4 or
1,2,5-trisubstituted glyoxalidines in which at least one substituent group is a hydroxyalkyl radical.
The new compounds are characterized as being either high-boiling viscous liquids, or lowmelting, waxy solids and by being highly polar andstrongly basic. They are colloidally dispersible in cold water, giving rise to viscous solutions, and they are completely soluble in acids, such as dilute hydrochloric acid. The glyoxalidine compounds of this invention may be used for various purposes, and it has been found that they are especially valuable as emulsifying agents, detergents, wetting, softening and scouring agents, and for other uses where their properties of surface activity can be employed. The new substances, and their salts and soaps, when used as emulsifying agents, are particularly emicacious'for producing stable dispersions of mineral oils, or other oleaginous substances and water. The new substances are also valuable as softening and finishing agents for textiles, according to processes set forth in application Serial No. 276,122, filed May 27, 1939, by B. G. Wilkes and A. L. Wilson, and as assistants in dyeing textiles to improve the fastness and other qualities of the dyeing operation.
The production of the substituted glyoxalidines of this invention may be accomplished by dehydrating fatty acid amides of various hydroxyalkyl alkylene polyamines and their substitution products, or, more generally stated, by heating, at temperatures between about 120C. and about 300 0., these amines with free fatty acids, fatty acid esters or amides under such conditions as to effect the splitting out of water in excess of 1.5 mols for each mol of free fatty acid and in excess of 0.5 mol for each mol of combined fatty acid involved. Examples of amines that may be employed in the practice of this invention are hydroxyethyl ethylene diamine, hydroxyisopropyl propylene diamine, hydroxyethyl diethylene triamine hydroxyethyl triethylene tetramine, as well as similar hydroxyalkyl alkylene polyamines. The hydroxyalkyl alkylene polyamines of this invention are of the 1,2 series, that is, at least one amino group and one imino group are attached to adjacent carbon atoms. The term alkylene polyamine" is also defined as including products containing more than one alkylene group. Fatty acid compounds that may be used in the production of the glyoxalidines may include the fatty acids themselves, such as lauric, oieic, linoleic, ricinoleic, stearic and palmitic acids, as well as their salts and esters. Other fatty acids and their salts and esters naturally occurring in such vegetable oils as olive, cocoanut, linseed and cottonseed oils, which have 10 to 20 carbon atoms in their molecule, may also be employed.
The substituted glyoxalidines of this invention may be regarded as dehydration products of substituted ethylene diamines and fatty acids, or their salts and esters. The formation of the glyoxalidine or imidazoline ring from these substances may be considered as a two-step reaction involving, first, the formation of an amide and a molecule of water, and, second, the dehydration of this amide to yield a substituted glyoxalidine and a second molecule of water. Thus, when a fatty acid, such as oleic acid, is employed, two molecules of water ,will be formed per molecule of the starting acid. This reaction is illustrated by the following scheme:
from
wherein It represents an aliphatic radical con i compounds, are represented by the following gentaining from to 20 carbon'ratoms and being theresidue of a higher fatty acid; R1 represents hydrogen or a lower alkyl group; andRz represents an alkylene group, a lower alkyl substituted alkylene group, or ,a radical of the structure CHR1.CHR1 (NH.CHR1'.CHRI1) 12- where R1 remains hydrogen or a lower alkyl group and a: is an integer.
In comparison with the amino alkyl substituted glyoxalidines, disclosed in my copending application Serial No, 191,191, the hydroxyalkyl substituted glyoxalidines of this application are obtained somewhat more readily and with considerably less tendency towards the formation of polyamides or other high-boiling condensation products. Another point of distinction is that,
in preparing the former compounds, it is desirable to use a fairly high molar ratio of alkylene polyamine to fatty acidto insure a high yield of glyoxalidine whereas, in making the latter substances, a satisfactory yield of pure glyoxalidine results when operating with equal molecular quantities of hydroxyalkyl alkylene polyamine and fatty acid. 7
It is true, nevertheless, that the employment ofhigher molar ratios of hydroxyalkyl alkylene polyamine to fatty acid will promote a .higher yield of the desired hydroxyalkyl substituted glyoxalidine but such practice is not required for the success of the reaction. Other factors which act to increase the yield of the hydroxyalkyl substituted glyoxalidines are higher rates of heating attendant with the use of temperatures in the upper portion of the range indicated to be suitable and an increased rate of removal of the water liberated in the condensation. Such an increase may be effected by distilling the water from the reaction vessel as a constant boiling mixture with a volatile water-immiscible diluent. Examples of such liquids are benzene, xylene, toluene, diisopropyl ether, ethyl acetate. ethylene dichloride, and carbon tetrachloride. If a diluent is used in carrying out the reaction, lower temperatures and lower molar ratios of hydroxyalkyl alkylene polyamine may be used and high yields of the desired glyoxalidine obtained nevertheless. This characteristic is illustrated in Example V.
Since the substituted glyoxalidines contain a reactive hydroxy group, it is possible to form esters of these compounds by the reaction of organic acids with the free alcoholic group. Be cause the glyoxalidine compounds are basic, it is possible to form salts or soaps of these compounds by their addition with various acidic substances. including both mineral and organic acids, such as hydrochloric, sulfuric, acetic, ethyl hexoic, and lauric acids. such salts or soaps the solubility of these compounds is enhanced. Quaternary ammonium compounds may also be formed by warming the substituted glyoxalidines with the appropriate reagents, such..as diethyl sulfate, dimethyl sulfate, benzyl chloride and the like. These compounds are usually viscous liquids to wax-like bodies, characterized by their nearly neutral reaction and by their ready solubility in water. These quaternary compounds are perhaps less useful as emulsifying agents and as textile fin- By the formation of,
ishing agents than the substituted glyoxalidines themselves but they possess exceptional qualities as wetting and flotation agents.
The salts, as well as the quaternary ammonium eral structure:
in which R, R1, and R2 are as indicated in the above formula; Y represents an organic or inorganic radical, and R3 is hydrogen, or an alkyl or aralkyl group. The distinction between the salts and the quaternary ammonium compounds is that, in the former, R: is usually hydrogen whereas, in the latter, R3 is usually an alkyl or aralkyl group and Y is generally an inorganic radical.
The following examples will serve to illustrate the invention:
Example I One mol of beta-hydroxyethyl ethylene diamine was mixed with 0.5 mol of commercial oleic acid and heated under reflux for 5 hours until a final temperature of about 270 C. was reached. About 2 mols of water per mol of oleic acid were distilled off during this period. Excess hydroxyethyl ethylene diamine was then removed, and the product, 1-hydroxyethyl-2-heptadecenyl glyoxalidine, was purified by vacuum distillation. This substance was found to be a straw-colored, heavy, viscous liquid, with a specific gravity of 0.935 at 20/20 C. and a boiling point from about 230 to 240 C. at an absolute pressure of 1 mm. of mercury. It was miscible with water at 10 C. to yield viscous solutions and it was completely soluble in dilute hydrochloric and acetic acids. This glyoxalidine is particularly useful for dispersing mineral oils in water and in producing water scourable mineral oils for use as textile lubricants.
Example II One and one-half mols of hydroxyethyl ethylene diamine were mixed with one mol of stearic acid and heated, in the presence of xylene, under reflux for 8 hours at a temperature of from C. to C. About 1.5 mols of water per mol of stearic acid were distilled oil! as a constant boiling mixture with the xylene during this period. Excess amine and xylene were then removed, and the product, 1-hydroxyethyl-2-heptadecyl glyoxalidine, was purified by vacuum distillation. This substance was a light-colored solid, insoluble in water, melting at 45 to 55 C.,
and boiling at 240 to 250 C. atan absolute pressure of 1 mm. of mercury. This product is es- I pecially valuable as a softening and finishing agent for regenerated cellulose fabrics, cotton, and similar fibrous materials and as an assistant in dyeing textiles to improve the fastness and substantivity. It is also useful where surface.
a water-soluble wax-like solid and is valuable as 75 an emulsifying agent and as a textile finishing.
lameness v 3 agent. It is also very useful as adetergent being 1 molar quantities of the reactants used in each unaffected in its action by hard water, or by dilute salt water or even by acid solutio Example III Two mols of hydroxyethyl ethylene cliamine were mixed with one mol of cocoanut fatty acids and heated for 3 hours at a temperature of from 170 C. to 270 C. During this period 1.8 mols of water were distilled off. Excess amine was removed and the product, l-hydroxyethyl-2-undecyl glyoxalidine, was purified by vacuum distillation. This substance was a straw-colored semi-crystalline solid with a melting point of 35 to 40 C., a specific gravity of 0.950 at 20/20 Example IV One mol of oleic acid was heated with two mols of N-beta-hydroxypropyl propylene diamine, believed to consist of the structure H2N.CH. CH:.N.CH2. $11. OH
H: H CH:
and its isomers, for 5 hours at a temperature of from 170 to 273 C. During-this period nearly 2 mols of water were removed by distillation. The excess amine was then removed and the product, l-hyclroxyisopropyl 2 heptadecenyll-methyl glyoxalidine, was purified by vacuum distillation. The pure substance was a light-colored liquid having a specific gravity of 0.920 at 20/20 C. and a boiling point of 225 to 235 C. at an absolute pressure of 1 mm. of mercury. The glyoxalidine was slightly soluble in water and completely soluble in dilute acid solutions. These solutions showed typical surface active properties, such as foaming and emulsifying action.
This compound may be prepared by reacting propylene diamine, having the structure H:C.CH.CH:.NH:
NHg, with propylene oxide, H;CHCCH2 Four isomers are possible dep ending on the amino group hydroxyalkylated and on w ether the propylene oxide adds in its alpha or beta position to the amino group.
Example V No. l norylene No. 2 xylene present present Hy ethyl ethylene dinmine My pm" 104 104 Oleio acid -.do--.. 282 282 xylene do.-.. None 91 Time oi reactio 5 Final temperature. ...C 310 205 Water removed .parts. 27' 7 Appearance of final product Dark sludge Lighthclslar Solubility in water Not miscible M igdllaat -Peroent glyoxalidine by distillation at220 M280 C.and2mm per cent 41 81 From this example, it is apparent that carrying out the reaction in the presence of a waterimmiscible liquid diluent is more than a convenient expedient for removal of the water of dehydration. Decidedly superior results have been obtained by this procedure.
I claim:
1. As surface active agents, substituted glyoxalidines of the formula B-C CHI-R1 HoR,1 I -tH.R. in which R is an aliphatic radical containing from 10 to 20 carbon atoms; R1 is of the group consisting of hydrogen and lower alkyl; and R:
til
is of the group consisting of an alkylene hydrocarbon group, a lower alkyl substituted alkylene hydrocarbon group, and a radical of the structure CHR1.CH R1 (NH.CHR1.CHR1) 1- where a: is an integer.
2. As surface active agents, substituted glyoxalidines of the formula in which R is an aliphatic radical containing from 10 to 20 carbon atoms; R1 is of the group consisting of hydrogen and methyl; and R2 is an alkylene hydrocarbon group, a lower alkyl substituted alkylene hydrocarbon group, or a radical of the structure CHR1.CHR1 (NH.CHR1.CHR1) z:-
where a: is an integer.
3. As surface active agents, salts of the glyoxalidines defined in claim 1.
4. As surface active agents, quaternary ammonium compounds of the glyoxalidines defined in claim 1.
5. As a surface active agent, l-hydroxyethyl-Z- heptadecenyl glyoxaldine, being characterized as a viscous liquid, completely soluble in dilute hydrochloric acid, and boiling from about 230 to 8. Process for making substituted glyoxalidines which comprises heating a mixture containing a free hydroxyalkyl alkylene poiyamine of the 1, 2 series and at least one of group consisting of free fatty acids containing from 10 to 20 carbon atoms, amides of said acids, and esters of said acids, at temperatures between about*120 and about 300 C., and removing water continuously from said mixture during said heating, the temperature and the duration of said heating being so correlated as to cause the splitting out of. water in excess of 1.5 mols for each mol of free fatty acid and in excess of 0.5 moi for each moi of combined fatty acid involved.
with said diluent during said heating, the temperature and the duration of said heating being so correlated as to cause the splitting out of water in excess of 1.5 mole for each moi of fatty acid involved.
ALEXANDER L. WILSON.
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| US285081A US2267965A (en) | 1939-07-18 | 1939-07-18 | Hydroxyalkyl glyoxalidines |
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| US2416552A (en) * | 1940-05-29 | 1947-02-25 | Richards Chemical Works Inc | Conversion of alkylolamides into oxazolines |
| US2418077A (en) * | 1943-08-13 | 1947-03-25 | Monsanto Chemicals | 1, 2-disubstituted-4, 5-dihydroimidazoles |
| US2450534A (en) * | 1945-08-04 | 1948-10-05 | Huber Corp J M | Emulsion printing inks |
| US2496641A (en) * | 1946-11-12 | 1950-02-07 | Nopco Chem Co | Fat liquoring and alum tanning |
| US2496640A (en) * | 1944-05-18 | 1950-02-07 | Nopco Chem Co | Fat liquoring and alum tanning |
| US2508415A (en) * | 1946-02-13 | 1950-05-23 | Monsanto Chemicals | Method of making 4, 5-dihydroimidazoles |
| US2509260A (en) * | 1946-04-19 | 1950-05-30 | Us Vanadium Corp | Method of filtration |
| US2528378A (en) * | 1947-09-20 | 1950-10-31 | John J Mccabe Jr | Metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates and process for preparation of same |
| US2659731A (en) * | 1953-11-17 | Cakbocyclic monocarboxyijc acid | ||
| US2662857A (en) * | 1948-03-26 | 1953-12-15 | Pennsylvania Salt Mfg Co | Pickling bath agent |
| US2669546A (en) * | 1949-12-23 | 1954-02-16 | Alrose Chemical Company | Detergents containing imidazoline lactates |
| US2781357A (en) * | 1954-12-03 | 1957-02-12 | John J Mccabe Jr | Imidazoline derivatives and process |
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| US2901430A (en) * | 1953-11-06 | 1959-08-25 | Gen Aniline & Film Corp | Corrosion inhibition |
| US2953535A (en) * | 1957-09-11 | 1960-09-20 | Borden Co | Resin binder compositions |
| US2987514A (en) * | 1958-03-03 | 1961-06-06 | Petrolite Corp | Polyesters |
| US2987521A (en) * | 1958-03-03 | 1961-06-06 | Petrolite Corp | Polymeric partial esters of hydrocarbon-diimidazolinylalkanols and dicarboxylic acids |
| US3047425A (en) * | 1959-07-16 | 1962-07-31 | Monsanto Chemicals | Method for producing flame and soil resistant acrylic polymer fibers containing carpet fabric |
| US3138610A (en) * | 1961-03-10 | 1964-06-23 | Gen Aniline & Film Corp | Substituted imidazolines |
| US3216957A (en) * | 1962-08-14 | 1965-11-09 | Union Carbide Corp | Antistatic thermoplastic vinyl resin compositions comprising oxyalkylated imidazolines |
| US3231494A (en) * | 1961-08-22 | 1966-01-25 | Exxon Research Engineering Co | Rust preventive prepared from sodium nitrite and the reaction product of fatty acid and imidazoline |
| US3251853A (en) * | 1962-02-02 | 1966-05-17 | Lubrizol Corp | Oil-soluble acylated amine |
| US3313825A (en) * | 1961-07-25 | 1967-04-11 | Geigy Chem Corp | Certain imidazoline salts |
| US3317556A (en) * | 1962-06-22 | 1967-05-02 | Nopco Chem Co | Amphoteric alpha-sulfo-imidazolines |
| US3468904A (en) * | 1965-10-24 | 1969-09-23 | Hodag Chem Corp | Production of light-colored fattyderived amino-containing compounds |
| US4095941A (en) * | 1974-10-04 | 1978-06-20 | Hoechst Aktiengesellschaft | Fiber preparation agents to produce a marked separating capability |
| US4117231A (en) * | 1975-07-22 | 1978-09-26 | The Miranol Chemical Company, Inc. | Nitrogenous condensation products |
| EP0002943A1 (en) * | 1977-12-22 | 1979-07-11 | Albright & Wilson Limited | Process for the manufacture of imidazolines |
| US4189593A (en) * | 1978-05-01 | 1980-02-19 | Baker Thomas G | Process for making imidazolines |
| US4233451A (en) * | 1976-05-20 | 1980-11-11 | The Procter & Gamble Company | Process for making imidazolinium salts |
| US4954635A (en) * | 1989-09-06 | 1990-09-04 | The Procter & Gamble Company | Process for preparing quaternized imidazoline fabric conditioning compounds |
| US4968443A (en) * | 1988-07-22 | 1990-11-06 | Colgate-Palmolive Company | Antistatic laundry detergent composition and processes therefor |
| US5024677A (en) * | 1990-06-11 | 1991-06-18 | Nalco Chemical Company | Corrosion inhibitor for alcohol and gasohol fuels |
| US5334329A (en) * | 1988-10-07 | 1994-08-02 | The Lubrizol Corporation | Lubricant and functional fluid compositions exhibiting improved demulsibility |
| US5334639A (en) * | 1992-01-30 | 1994-08-02 | Ppg Industries, Inc. | Starch oil sizing composition and glass fibers treated therewith |
| US5393335A (en) * | 1993-04-23 | 1995-02-28 | Ppg Industries, Inc. | Starch-oil sizing for glass fibers |
| US5393379A (en) * | 1990-12-05 | 1995-02-28 | Ppg Industries, Inc. | Wet laid fiberous thermoplastic material and aqueous dispersion for producing same |
| US5466528A (en) * | 1992-08-21 | 1995-11-14 | Ppg Industries, Inc. | Chemically treated glass type substrates with vinyl polymer compatibility |
| US5747431A (en) * | 1994-01-12 | 1998-05-05 | Diversey Lever Inc. | Lubricant compositions |
| WO2001025214A1 (en) * | 1999-10-01 | 2001-04-12 | Hercules Incorporated | Method of producing low-odor imidazolines, imidazolines produced thereby and paper and paper products containing the same |
| EP1130012A2 (en) * | 2000-02-29 | 2001-09-05 | VaMa FarmaCosmetica S.r.l. | A process for the preparation of amphoglycinates from vegetable oils and butters and the use thereof |
| US6372918B1 (en) * | 1999-07-02 | 2002-04-16 | Clariant Gmbh | Compound for inhibiting corrosion |
| US20030056431A1 (en) * | 2001-09-14 | 2003-03-27 | Schwab Scott D. | Deposit control additives for direct injection gasoline engines |
| WO2007039488A1 (en) * | 2005-09-23 | 2007-04-12 | Basf Se | Hydroxyalkyl-substituted aminoalkylamides of fatty acids as friction modifying agents |
| WO2014178737A1 (en) | 2013-05-02 | 2014-11-06 | Instytut Nafty I Gazu - Panstwowy Instytut Badawczy | Corrosion inhibitor for protection of crude oil extraction equipment, crude oil pipelines, and crude oil tanks as well as the method of its production |
| WO2014178738A1 (en) | 2013-05-02 | 2014-11-06 | Instytut Nafty I Gazu - Panstwowy Instytut Badawczy | Water-soluble corrosion inhibitor for protection of lifting casings and natural gas pipelines as well as the method of its production. |
| WO2023222400A1 (en) | 2022-05-17 | 2023-11-23 | Evonik Operations Gmbh | Production of polyurethane foam |
-
1939
- 1939-07-18 US US285081A patent/US2267965A/en not_active Expired - Lifetime
Cited By (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2659731A (en) * | 1953-11-17 | Cakbocyclic monocarboxyijc acid | ||
| US2416552A (en) * | 1940-05-29 | 1947-02-25 | Richards Chemical Works Inc | Conversion of alkylolamides into oxazolines |
| US2418077A (en) * | 1943-08-13 | 1947-03-25 | Monsanto Chemicals | 1, 2-disubstituted-4, 5-dihydroimidazoles |
| US2496640A (en) * | 1944-05-18 | 1950-02-07 | Nopco Chem Co | Fat liquoring and alum tanning |
| US2450534A (en) * | 1945-08-04 | 1948-10-05 | Huber Corp J M | Emulsion printing inks |
| US2508415A (en) * | 1946-02-13 | 1950-05-23 | Monsanto Chemicals | Method of making 4, 5-dihydroimidazoles |
| US2509260A (en) * | 1946-04-19 | 1950-05-30 | Us Vanadium Corp | Method of filtration |
| US2496641A (en) * | 1946-11-12 | 1950-02-07 | Nopco Chem Co | Fat liquoring and alum tanning |
| US2528378A (en) * | 1947-09-20 | 1950-10-31 | John J Mccabe Jr | Metal salts of substituted quaternary hydroxy cycloimidinic acid metal alcoholates and process for preparation of same |
| US2662857A (en) * | 1948-03-26 | 1953-12-15 | Pennsylvania Salt Mfg Co | Pickling bath agent |
| US2669546A (en) * | 1949-12-23 | 1954-02-16 | Alrose Chemical Company | Detergents containing imidazoline lactates |
| US2901430A (en) * | 1953-11-06 | 1959-08-25 | Gen Aniline & Film Corp | Corrosion inhibition |
| US2781357A (en) * | 1954-12-03 | 1957-02-12 | John J Mccabe Jr | Imidazoline derivatives and process |
| US2874074A (en) * | 1956-05-08 | 1959-02-17 | Nat Aluminate Corp | 1, 2-substituted imidazolinium salt and treatment of cellulosic fibrous materials therewith |
| US2875210A (en) * | 1956-05-17 | 1959-02-24 | Nat Aluminate Corp | Chemical compositions |
| US2953535A (en) * | 1957-09-11 | 1960-09-20 | Borden Co | Resin binder compositions |
| US2987514A (en) * | 1958-03-03 | 1961-06-06 | Petrolite Corp | Polyesters |
| US2987521A (en) * | 1958-03-03 | 1961-06-06 | Petrolite Corp | Polymeric partial esters of hydrocarbon-diimidazolinylalkanols and dicarboxylic acids |
| US3047425A (en) * | 1959-07-16 | 1962-07-31 | Monsanto Chemicals | Method for producing flame and soil resistant acrylic polymer fibers containing carpet fabric |
| US3138610A (en) * | 1961-03-10 | 1964-06-23 | Gen Aniline & Film Corp | Substituted imidazolines |
| US3313825A (en) * | 1961-07-25 | 1967-04-11 | Geigy Chem Corp | Certain imidazoline salts |
| US3231494A (en) * | 1961-08-22 | 1966-01-25 | Exxon Research Engineering Co | Rust preventive prepared from sodium nitrite and the reaction product of fatty acid and imidazoline |
| US3251853A (en) * | 1962-02-02 | 1966-05-17 | Lubrizol Corp | Oil-soluble acylated amine |
| US3317556A (en) * | 1962-06-22 | 1967-05-02 | Nopco Chem Co | Amphoteric alpha-sulfo-imidazolines |
| US3216957A (en) * | 1962-08-14 | 1965-11-09 | Union Carbide Corp | Antistatic thermoplastic vinyl resin compositions comprising oxyalkylated imidazolines |
| US3468904A (en) * | 1965-10-24 | 1969-09-23 | Hodag Chem Corp | Production of light-colored fattyderived amino-containing compounds |
| US4095941A (en) * | 1974-10-04 | 1978-06-20 | Hoechst Aktiengesellschaft | Fiber preparation agents to produce a marked separating capability |
| US4117231A (en) * | 1975-07-22 | 1978-09-26 | The Miranol Chemical Company, Inc. | Nitrogenous condensation products |
| US4233451A (en) * | 1976-05-20 | 1980-11-11 | The Procter & Gamble Company | Process for making imidazolinium salts |
| EP0002943A1 (en) * | 1977-12-22 | 1979-07-11 | Albright & Wilson Limited | Process for the manufacture of imidazolines |
| US4212983A (en) * | 1977-12-22 | 1980-07-15 | Albright & Wilson Limited | Manufacture of imidazoline compounds |
| US4189593A (en) * | 1978-05-01 | 1980-02-19 | Baker Thomas G | Process for making imidazolines |
| US4968443A (en) * | 1988-07-22 | 1990-11-06 | Colgate-Palmolive Company | Antistatic laundry detergent composition and processes therefor |
| US5334329A (en) * | 1988-10-07 | 1994-08-02 | The Lubrizol Corporation | Lubricant and functional fluid compositions exhibiting improved demulsibility |
| US4954635A (en) * | 1989-09-06 | 1990-09-04 | The Procter & Gamble Company | Process for preparing quaternized imidazoline fabric conditioning compounds |
| US5024677A (en) * | 1990-06-11 | 1991-06-18 | Nalco Chemical Company | Corrosion inhibitor for alcohol and gasohol fuels |
| US5393379A (en) * | 1990-12-05 | 1995-02-28 | Ppg Industries, Inc. | Wet laid fiberous thermoplastic material and aqueous dispersion for producing same |
| US5334639A (en) * | 1992-01-30 | 1994-08-02 | Ppg Industries, Inc. | Starch oil sizing composition and glass fibers treated therewith |
| US5466528A (en) * | 1992-08-21 | 1995-11-14 | Ppg Industries, Inc. | Chemically treated glass type substrates with vinyl polymer compatibility |
| US5393335A (en) * | 1993-04-23 | 1995-02-28 | Ppg Industries, Inc. | Starch-oil sizing for glass fibers |
| US5747431A (en) * | 1994-01-12 | 1998-05-05 | Diversey Lever Inc. | Lubricant compositions |
| US6372918B1 (en) * | 1999-07-02 | 2002-04-16 | Clariant Gmbh | Compound for inhibiting corrosion |
| WO2001025214A1 (en) * | 1999-10-01 | 2001-04-12 | Hercules Incorporated | Method of producing low-odor imidazolines, imidazolines produced thereby and paper and paper products containing the same |
| EP1130012A2 (en) * | 2000-02-29 | 2001-09-05 | VaMa FarmaCosmetica S.r.l. | A process for the preparation of amphoglycinates from vegetable oils and butters and the use thereof |
| EP1130012A3 (en) * | 2000-02-29 | 2003-10-15 | VaMa FarmaCosmetica S.r.l. | A process for the preparation of amphoglycinates from vegetable oils and butters and the use thereof |
| US20030056431A1 (en) * | 2001-09-14 | 2003-03-27 | Schwab Scott D. | Deposit control additives for direct injection gasoline engines |
| WO2007039488A1 (en) * | 2005-09-23 | 2007-04-12 | Basf Se | Hydroxyalkyl-substituted aminoalkylamides of fatty acids as friction modifying agents |
| WO2014178737A1 (en) | 2013-05-02 | 2014-11-06 | Instytut Nafty I Gazu - Panstwowy Instytut Badawczy | Corrosion inhibitor for protection of crude oil extraction equipment, crude oil pipelines, and crude oil tanks as well as the method of its production |
| WO2014178738A1 (en) | 2013-05-02 | 2014-11-06 | Instytut Nafty I Gazu - Panstwowy Instytut Badawczy | Water-soluble corrosion inhibitor for protection of lifting casings and natural gas pipelines as well as the method of its production. |
| WO2023222400A1 (en) | 2022-05-17 | 2023-11-23 | Evonik Operations Gmbh | Production of polyurethane foam |
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