US3389145A - Fatty oxazoline surfactants and a process for their preparation - Google Patents

Fatty oxazoline surfactants and a process for their preparation Download PDF

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US3389145A
US3389145A US504991A US50499165A US3389145A US 3389145 A US3389145 A US 3389145A US 504991 A US504991 A US 504991A US 50499165 A US50499165 A US 50499165A US 3389145 A US3389145 A US 3389145A
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • 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
    • Y10S516/06—Protein or carboxylic compound containing

Definitions

  • the preferred oil and water soluble surface active compounds have the following general formula:
  • R represents a hydrocarbon group containing from 7 to 21 carbon atoms
  • R R and R are short chain hydrocarbon groups containing 1 to 6 carbon atoms
  • X represents oxygen taking the form of an ether
  • alkali metal salts of these fatty complexes are water soluble and are versatile adjuncts in such diverse fields as cosmetic and shampoo preparations, industrial and household cleaners, detergent and scouring agents for processing textiles, emulsifiers and corrosion inhibitors.
  • fatty oxazoline nitrogen carboxylic acids are soluble in polar and non-polar solvents, and may be neutralized with amines to form oil soluble salts. Both the carboxylic acids and their amine salts are excellent film forming compounds, exhibiting outstanding corrosion inhibiting properties.
  • coconut fatty acid, oleic fatty acid, tall oil fatty acid, stearic acid or sebacic acid are combined starting at 300 F. and increasing up to 450 F. with amino hydroxy compounds which contain at least one primary amino group and two or more hydroxy groups as set forth below:
  • the acrylic compounds should desirably have one unsaturated double bond in the aliphatic chain and contain from one to four carbon atoms, and they have terminal CN or COOH groups.
  • a three-neck flask is utilized with a condenser connected to one neck, an agitator connected through the other neck and a funnel or thermometer is connected in the third neck.
  • the acrylic compound is dropped for about one hour, followed by heating for about one and one-half to three hours at 180 to 230 F. with the final processing and elevated temperature treatment taking place at 15 to 18 inches vacuum.
  • reaction product is treated with equimolar proportions of caustic soda in 25% concentration and at temperature of about 200 F. for about one and one-half to three hours.
  • the R group is desirably derived from oleic acid, tall oil fatty acid or coconut fatty acid and less desirably from sebacic acid.
  • They are surprisingly effective as detergents, emulsifiers and corrosion inhibitors in very small concentrations. They may be used in shampoos, in soaps, in emulsion polymerization, as oven cleaners, as industrial cleaners, in electroplating, in cosmetics, for textile scouring, dyeing and lubrication, in sanitizers, in paints, and in leather treating.
  • the high molecular weight fatty oxazolines are formed by the reaction of carboxylic acids, esters, acid chlorides and acid anhydrides containing 8 to 32 carbon atoms in the molecule with alkylol amines as monoethanolamine, diethanolamine, 2- amino-2-methyl-1.3-pr0panediol and tris (hydroxymethyl aminometh ane.
  • EXAMPLE II The long chain oxazolines are manufactured from 1,2- hydroxyamine by acylation and cyclodehydration.
  • the contents was heated with agitation to C. and held at this temperature until one mol (18 milliliters) of water was obtained in the moisture trap.
  • the temperature was then raised to 200 C. and maintained at this temperature, until another mol (18 milliliters) of water was obtained in the moisture trap at which time the cyclodehydration step was complete and the liquid oxazoline analyzed 92% 2-oleyl-4-methyl-4-hydroxymethyl oxazol-
  • the moisture trap was removed and the flask rearranged for reflux, and cooled to 50 C. Five milliliters of a 25% sodium methylate solution were added as a catalyst for the addition reaction and then one mol of methyl acrylate was added slowly through a dropping funnel and the mixture stirred at 50-70 C. for two hours.
  • the temperature employed in carrying out the reaction for the amide formation is 150 C. to 180 C. after which the temperature is increased to 215 C. for the cyclodehydration process to form the oxazoline ring.
  • the oxazoline was cooled to 50 C. and 2 mols of methyl acrylate or acrylonitrile containing 0.1% NaOCH was added over a period of one hour. The temperature was then slowly raised to 100 C. and held there until tests showed all the methyl acrylate or acrylonitrile had reacted to form the bis(methoxypropionitrile) or equivalent derivative.
  • methyl acrylate or acrylonitrile adducts of these long chain oxazoline nitrogen compounds are oil soluble surfactants. They are dispersible in water, lowering the surface tension of water to 30 dynes/centimeters at 0.1 concentration.
  • the compounds are completely soluble in alcohols, ketones, ethers, and aromatic and aliphatic hydrocarbons. They act as good corrosion inhibitors, filming compounds, dewatering agents and show selective fungicidal and biocidal activity, either by themselves or in the form of the acetate of hydrochloride salt.
  • the water soluble alkali propionates of these long chain oxazoline nitrogen compounds have been found to be detergents in the wet processing of textiles and leather, excellent wetting and emulsifying agents, dyeing assistants, and finishing compounds.
  • alkanoic acids of these long chain oxazoline nitrogen compounds may be combined with amines to form both oil and water soluble emulsifiers with corrosion inhibiting properties.
  • EXAMPLE VII An excellent scouring and softening agent for textiles was prepared by reacting methyl stearate with trishydroxymethyl amino methane at ISO-200 C. to form the oxazoline derivative which was then reacted with two moles of ethyl acrylate (one mole for each available hydroxy group of the above oxazoline).
  • the fatty dimethoxyethylpropionate oxazoline was saponified with two moles of NaOH dissolved in water to form a white paste containing 20% active matter.
  • a 1% solution of the above paste imparted a soft hand to nylon, Acrilan, a trademark for an acrylic fiber, cellulose acetate and other synthetic fibers.
  • the chemical structure can be described as 2-heptadecyl-4,4-bis (methoxy sodium propionate)-2-oxazoline,
  • the iii-oxazoline formed was a yellow oil, soluble in alcohols, ketones and hydrocarbons. It was cooled to 60 C. and two moles of methyl acrylate were slowly added, the mixture was then raised to 90 C. and held at this temperature for three hours. The infrared spectrum of the resulting adduct showed a steep ether peak and almost the complete absence of the original hydroxy groups.
  • the sodium salt was obtained by pouring this product into two liters of water containing two moles of NaOH and stirred for one hour at C. until the pH dropped to 9.0 and the final product was soluble in water.
  • the amine salts of this compound may be prepared by substituting low molecular weight alkyl amines, alkylol amines and ether amines (di-butyl amine, tripropylamine, monoethanolamine and morpholine) in place of the NaOH in the saponification step.
  • the amine salts of this derivative are soluble in alcohols, ethers, ketones, hydrocarbons such as kerosene and aromatic solvents such as toluene. They are excellent emulsifiers and exhibit outstanding filming properties as corrosion inhibitors.
  • R being a fatty acid radical selected from a group consisting of coconut fatty acid, oleic acid, tall oil fatty acid, stearic acid and sebacic acid.
  • M is selected from the group consisting of hydrogen and alkali metal and a low molecular weight amine selected from the group consisting of di-butyl amine, tripropylamine, monoethanolamine and morpholine.
  • NICHOLAS S. RIZZO Primary Examiner.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

United States Patent "ice 3,380,145 FATTY OXAZOLLNE SURFACTANTS AND A PRGCESS FQR THEIR PREPARATION Jacob Katz, 1224 Mention Road, Providence, Rd. 02904 No Drawing. Filed Oct. 24, 1965, Ser. No. 504,991 9 Claims. (Cl. 260-307) The present application relates to novel surfactants, and it particularly relates to a high molecular weight fatty oxazoline surfactant having high effectiveness in a wide variety of acidities and alkalinities.
It is among the objects of the present invention to provide a highly elfective detergent which will maintain a high fine bubble foam over long periods of time in textile processing, without deterioration or loss of effective foam properties and without decreasing the volume of the foam regardless of the change in pH, Whether it become strongly acid or become strongly alkaline, regardless of the salts that may be present or the pH of the bath in t which the foam is being produced, and which will have unusually high corrosive inhibiting properties and which may be widely utilized in metal processing such as electroplating, radiator liquids, and coolants for metal working processes.
The preferred oil and water soluble surface active compounds have the following general formula:
o-o m where R represents a hydrocarbon group containing from 7 to 21 carbon atoms, R R and R are short chain hydrocarbon groups containing 1 to 6 carbon atoms, and X represents oxygen taking the form of an ether.
The alkali metal salts of these fatty complexes are water soluble and are versatile adjuncts in such diverse fields as cosmetic and shampoo preparations, industrial and household cleaners, detergent and scouring agents for processing textiles, emulsifiers and corrosion inhibitors.
These compounds are anionic in basic solution and cationic in acid solution; and in the range of pH 5.0 to 9.0, they exhibit both cationic and anionic properties, being truly amphoteric.
As fatty oxazoline nitrogen carboxylic acids, they are soluble in polar and non-polar solvents, and may be neutralized with amines to form oil soluble salts. Both the carboxylic acids and their amine salts are excellent film forming compounds, exhibiting outstanding corrosion inhibiting properties.
They are effective as petroleum additives, detergents, asphalt wetting and anti-stripping agents and biocidal agents.
To give the chemical equations which are involved in making the above compounds, coconut fatty acid, oleic fatty acid, tall oil fatty acid, stearic acid or sebacic acid are combined starting at 300 F. and increasing up to 450 F. with amino hydroxy compounds which contain at least one primary amino group and two or more hydroxy groups as set forth below:
2-amino-2-methyl-1.3propanediol 2-amino-2-ethyl-1.3-propanediol tris (hydroxymethyl)aminomethane The reaction between the fatty acid and the amine compound is represented as follows.
3,389,145 Patented June 18, 1968 in which -R is an alkyl group having 8 to 22 carbon atoms and the amine is 2-amino-2-methy-l-1.3-propanediol.
Then to one mol of these oxazoline compounds is added in dropwise fashion one mol of an acrylic compound, such as methyl acrylonitrile or methyl acrylate at a temperature of to 150 F.
The acrylic compounds should desirably have one unsaturated double bond in the aliphatic chain and contain from one to four carbon atoms, and they have terminal CN or COOH groups.
They also have methyl, ethyl or propyl groups either as terminal groups or as side chains.
Desirably, a three-neck flask is utilized with a condenser connected to one neck, an agitator connected through the other neck and a funnel or thermometer is connected in the third neck.
The acrylic compound is dropped for about one hour, followed by heating for about one and one-half to three hours at 180 to 230 F. with the final processing and elevated temperature treatment taking place at 15 to 18 inches vacuum.
After this combination, with the acrylic compounds, has been completed, the reaction product is treated with equimolar proportions of caustic soda in 25% concentration and at temperature of about 200 F. for about one and one-half to three hours.
In these compounds, the R group is desirably derived from oleic acid, tall oil fatty acid or coconut fatty acid and less desirably from sebacic acid.
They are surprisingly effective as detergents, emulsifiers and corrosion inhibitors in very small concentrations. They may be used in shampoos, in soaps, in emulsion polymerization, as oven cleaners, as industrial cleaners, in electroplating, in cosmetics, for textile scouring, dyeing and lubrication, in sanitizers, in paints, and in leather treating.
The high molecular weight fatty oxazolines are formed by the reaction of carboxylic acids, esters, acid chlorides and acid anhydrides containing 8 to 32 carbon atoms in the molecule with alkylol amines as monoethanolamine, diethanolamine, 2- amino-2-methyl-1.3-pr0panediol and tris (hydroxymethyl aminometh ane.
EXAMPLE II The long chain oxazolines are manufactured from 1,2- hydroxyamine by acylation and cyclodehydration.
Into a two-liter three-neck flask equipped with moisture trap, condenser, stirrer and thermometer was charged 282 grams of oleic acid and grams (1.1 mol) of Z-amino- Z-rnethyl-1.3-propanediol.
The contents was heated with agitation to C. and held at this temperature until one mol (18 milliliters) of water was obtained in the moisture trap. The temperature was then raised to 200 C. and maintained at this temperature, until another mol (18 milliliters) of water was obtained in the moisture trap at which time the cyclodehydration step was complete and the liquid oxazoline analyzed 92% 2-oleyl-4-methyl-4-hydroxymethyl oxazol- The moisture trap was removed and the flask rearranged for reflux, and cooled to 50 C. Five milliliters of a 25% sodium methylate solution were added as a catalyst for the addition reaction and then one mol of methyl acrylate was added slowly through a dropping funnel and the mixture stirred at 50-70 C. for two hours.
Upon completion of the reaction, at which time analysis showed less than l% residual methylacrylate, the 2- oleyl-4-methyl-4-methoxy methyl propionate oxazoline was a brown liquid, soluble in both polar and non-polar solvents.
200 grams of sodium hydroxide was then added to the contents of the flask over a period of one hour with stirring and then the temperature raised to 95 C. for two hours when test samples showed the saponification to be complete. The resulting 2-oleyl or heptadecenyllmethyl-4-methoxy sodium propionate oxazoline solution was then diluted to 33 active matter.
EXAMPLE III.-SUBSTITUTED OXAZOLINES In making 2-undecyl-4.4'-bis(methoxysodium propionate)2-oxazoline, the equipment necessary to prepare this derivative is the same as described in the previous examle. P Lauric acid and tris(hydroxymethyl) amino methane are reacted in equimolar quantities.
The temperature employed in carrying out the reaction for the amide formation is 150 C. to 180 C. after which the temperature is increased to 215 C. for the cyclodehydration process to form the oxazoline ring.
The oxazoline was cooled to 50 C. and 2 mols of methyl acrylate or acrylonitrile containing 0.1% NaOCH was added over a period of one hour. The temperature was then slowly raised to 100 C. and held there until tests showed all the methyl acrylate or acrylonitrile had reacted to form the bis(methoxypropionitrile) or equivalent derivative.
Two mols of caustic soda (50% aqueous solution were then added and the reaction product saponified to the carboxylic acid-sodium salt.
The methyl acrylate or acrylonitrile adducts of these long chain oxazoline nitrogen compounds are oil soluble surfactants. They are dispersible in water, lowering the surface tension of water to 30 dynes/centimeters at 0.1 concentration.
The compounds are completely soluble in alcohols, ketones, ethers, and aromatic and aliphatic hydrocarbons. They act as good corrosion inhibitors, filming compounds, dewatering agents and show selective fungicidal and biocidal activity, either by themselves or in the form of the acetate of hydrochloride salt.
- The water soluble alkali propionates of these long chain oxazoline nitrogen compounds have been found to be detergents in the wet processing of textiles and leather, excellent wetting and emulsifying agents, dyeing assistants, and finishing compounds.
As petroleum additives, they serve as corrosion inhibitors for aqueous salt and acid solutions, filming compounds on metals, dewatering agents, in the mining industry as flotation agents, frothing compounds and selective mineral wetting agents.
In the pharmaceutical industry, these compounds offer combined detergency with germicidal properties.
The alkanoic acids of these long chain oxazoline nitrogen compounds may be combined with amines to form both oil and water soluble emulsifiers with corrosion inhibiting properties.
EXAMPLE IV CH3 N-(lE-CHr-O-CQILCOOH; NaO H n aaC radium compound O-GH: methyl alcohol 4 EXAMPLE v General Formula N-C-MN Where a fatty acid group having 8 to 22 carbon atoms and where M or N or both are a CH X (CH COONa grouping and the remaining M or N is hydrogen or an alkyl having 1 to 6 carbon atoms.
In the process of producing the above identified surfactants, the following are the important steps:
(a) Slow addition of the acrylate (b) The use of methyl acrylate (c) The temperature range from 140 to 212 F. or 60 C. to 100 C.
l d) The finishing operation at higher temperature to) The stripping of any excess if) The production of 98% yield.
As additional examples:
EXAMPLE VII An excellent scouring and softening agent for textiles was prepared by reacting methyl stearate with trishydroxymethyl amino methane at ISO-200 C. to form the oxazoline derivative which was then reacted with two moles of ethyl acrylate (one mole for each available hydroxy group of the above oxazoline). The fatty dimethoxyethylpropionate oxazoline was saponified with two moles of NaOH dissolved in water to form a white paste containing 20% active matter.
A 1% solution of the above paste imparted a soft hand to nylon, Acrilan, a trademark for an acrylic fiber, cellulose acetate and other synthetic fibers. The chemical structure can be described as 2-heptadecyl-4,4-bis (methoxy sodium propionate)-2-oxazoline,
EXAMPLE VIII One mole of dimer acids (mol. wt. 560) was reacted with two moles of aminoethyl propanediol at ISO-200 C. under 20 inches of vacuum.
The iii-oxazoline formed was a yellow oil, soluble in alcohols, ketones and hydrocarbons. It was cooled to 60 C. and two moles of methyl acrylate were slowly added, the mixture was then raised to 90 C. and held at this temperature for three hours. The infrared spectrum of the resulting adduct showed a steep ether peak and almost the complete absence of the original hydroxy groups.
The sodium salt was obtained by pouring this product into two liters of water containing two moles of NaOH and stirred for one hour at C. until the pH dropped to 9.0 and the final product was soluble in water.
The amine salts of this compound may be prepared by substituting low molecular weight alkyl amines, alkylol amines and ether amines (di-butyl amine, tripropylamine, monoethanolamine and morpholine) in place of the NaOH in the saponification step.
The amine salts of this derivative are soluble in alcohols, ethers, ketones, hydrocarbons such as kerosene and aromatic solvents such as toluene. They are excellent emulsifiers and exhibit outstanding filming properties as corrosion inhibitors.
l-Iaving now particularly described and ascertained the nature of the invention, and in what manner the same is to be performed, what is claimed is:
1. A fatty oxazoline surfactant having the formula O-CH; in which R is selected from the group consisting of alkyl and alkenyl having 11 to 18 carbon atoms and R R and R are alkyl groups having 1 to 6 carbon atoms and X is a linkage consisting of an oxygen atom and Y is selected from the group consisting of hydrogen, alkali metal and a group of amines consisting of di-butyl amine, tripropylamine, monoethanolamine and morpholine.
2. The surfactant of claim 1, R being a fatty acid radical selected from a group consisting of coconut fatty acid, oleic acid, tall oil fatty acid, stearic acid and sebacic acid.
3. The surfactant of claim 1, consisting of O-GH: in which R is selected from a group consisting of alkyl and alkenyl having 11 to 18 carbon atoms, and M is selected from the group consisting of hydrogen, alkali metal and a low molecular weight amine selected from the group consisting of di-butyl amine, tripropylamine, monoethanolamine and morpholine.
where M is selected from the group consisting of hydrogen and alkali metal and a low molecular weight amine selected from the group consisting of di-butyl amine, tripropylamine, monoethanolamine and morpholine.
7. The disodium salt of 4,4-bis(carboxyethyloxymethyl)-2-undecyl-2-oxazoline.
8. The disodium salt of 4,4-bis(carboxyethyloxymethyl)2-heptadecyl-2-oxazoline.
9. The process of making a surfactant in which a fatty acid having 7 to 21 carbon atoms is reacted with an amino compound selected from the group consisting of 2-amino-2-methyl-l-propanol, 2-amino-2-methyl-1.3-propanediol, 2-amino-2-ethyl-1.3-propanediol, tris(hydroxymethyl aminomethane and 2-amino-1-butanol and in which 1 mol of said amino compound is combined with 1 to 2 mols of the fatty acid, first by heating under a low vacuum of 15 to 20 inches for about 1 /2 to 3 hours at 350 F. and then continuing at 450 F. under a high vacuum of 25 to 29 inches for 5 to 8 hours, and then adding drop by drop to the reaction mixture 1 mol of an acrylic compound selected from the group consisting of methyl acrylate, ethyl acrylate and acrylonitrile at a temperature of to F., said dropwise addition continuing for about 1 hour, then following by heating for about 1 /2 to 3 hours at to 230 F. and increasing the vacuum to 15 to 18 inches and then treating the reaction mixture with caustic alkali.
References Cited UNITED STATES PATENTS 2,967,173 1/1961 Fang 260340.2
NICHOLAS S. RIZZO, Primary Examiner.
ALEX MAZEL, Examiner.
R. I. GALLAGHER, Assistant Examiner.

Claims (3)

1. A FATTY OXAZOLINE SURFACTANT HAVING THE FORMULA
5. A SURFACTANT CONSISTING OF
9. THE PROCESS OF MAKING A SURFACTANT IN WHICH A FATTY ACID HAVING 7 TO 21 CARBON ATOMS IS REACTED WITH AN AMINO COMPOUND SELECTED FROM THE GROUP CONSISTING OF 2-AMINO-2-METHYL-1-PROPANOL, 2-AMINO-2-METHYL-1.3-PROPANEDIOL, 2-AMINO-2-ETHYL-1.3-PROPANEDIOL, TRIS(HYDROXYMETHYL AMINOMETHANE AND 2-AMINO-1-BUTANOL AND IN WHICH 1 MOL OF SAID AMINO COMPOUND IS COMBINED WITH 1 TO 2 MOLS OF THE FATTY ACID, FIRST BY HEATING UNDER A LOW VACUUM OF 15 TO 20 INCHES FOR ABOUT 1 1/2 TO 3 HOURS AT 350*F. AND THEN CONTINUING AT 450*F. UNDER A HIGH VACUUM OF 25 TO 29 INCHES FOR 5 TO 8 HOURS, AND THEN ADDING DROP BY DROP TO THE REACTION MIXTURE 1 MOL OF AN ACRYLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF METHYL ACRYLATE, ETHYL ACRYLATE AND ACRYLONITRIL AT A TEMPERATURE OF 100 TO 150*F., SAID DROPWISE ADDITION CONTINUING FOR ABOUT 1 HOUR, THEN FOLLOWING BY HEATING FOR ABOUT 1 1/2 TO 3 HOURS AT 180* TO 230*F. AND INCREASING THE VACUUM TO 15 TO 18 INCHES AND THEN TREATING THE REACTION MIXTURE WITH CAUSTIC ALKALI.
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3483009A (en) * 1968-08-09 1969-12-09 Sherwin Williams Co Universal color base for coating compositions
US3509260A (en) * 1966-09-06 1970-04-28 Commercial Solvents Corp Composition and method for combatting fungi
US3533971A (en) * 1967-02-02 1970-10-13 Pan American Tung Research & D Polymer forming composition and electrodeposition thereof
US3967015A (en) * 1972-10-10 1976-06-29 Commercial Solvents Corporation Process for dyeing glass textiles
US4479888A (en) * 1979-08-10 1984-10-30 Agip Petroli S.P.A. Dispersing additives for lubricants, and the method for their preparation
US5336439A (en) * 1987-12-23 1994-08-09 The Lubrizol Corporation Salt compositions and concentrates for use in explosive emulsions
WO2001092237A1 (en) * 2000-06-01 2001-12-06 Unichema Chemie Bv Oxaline esterquats and their use as softeners and bactericides
US20050031956A1 (en) * 2001-12-14 2005-02-10 Ernest Ndzebet Oxazoline surfactant anode additive for alkaline electrochemical cells
US20070048575A1 (en) * 2005-08-30 2007-03-01 Rovcal, Inc. Electrochemical cells containing spun mercury-amalgamated zinc particles having improved physical characteristics
US20070048576A1 (en) * 2005-08-30 2007-03-01 Rovcal, Inc. Electrochemical cells containing spun mercury-amalgamated zinc particles having improved physical characteristics
US20070122709A1 (en) * 2005-11-30 2007-05-31 Rovcal, Inc. Ionically conductive clay additive for use in electrochemical cells
US20070122699A1 (en) * 2005-11-30 2007-05-31 Rovcal, Inc. Electrochemical cells having improved gelling agents
US20110070487A1 (en) * 2005-11-14 2011-03-24 Rovcal, Inc. Novel metal air cathode manganese oxide contained in octahedral molecular sieve
JP2015511239A (en) * 2012-02-17 2015-04-16 エピテック グループ エッセ．エッレ．エッレ． Compositions and methods for modulating amidases specific for N-acylethanolamines used in the treatment of inflammatory diseases

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2967173A (en) * 1956-03-22 1961-01-03 Du Pont Polymerizable esters of acrylic and methacrylic acid and polymers thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2967173A (en) * 1956-03-22 1961-01-03 Du Pont Polymerizable esters of acrylic and methacrylic acid and polymers thereof

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3509260A (en) * 1966-09-06 1970-04-28 Commercial Solvents Corp Composition and method for combatting fungi
US3533971A (en) * 1967-02-02 1970-10-13 Pan American Tung Research & D Polymer forming composition and electrodeposition thereof
US3483009A (en) * 1968-08-09 1969-12-09 Sherwin Williams Co Universal color base for coating compositions
US3967015A (en) * 1972-10-10 1976-06-29 Commercial Solvents Corporation Process for dyeing glass textiles
US4479888A (en) * 1979-08-10 1984-10-30 Agip Petroli S.P.A. Dispersing additives for lubricants, and the method for their preparation
US5336439A (en) * 1987-12-23 1994-08-09 The Lubrizol Corporation Salt compositions and concentrates for use in explosive emulsions
US5407500A (en) * 1987-12-23 1995-04-18 The Lubrizol Corporation Salt compositions and explosives using same
WO2001092237A1 (en) * 2000-06-01 2001-12-06 Unichema Chemie Bv Oxaline esterquats and their use as softeners and bactericides
US20050031956A1 (en) * 2001-12-14 2005-02-10 Ernest Ndzebet Oxazoline surfactant anode additive for alkaline electrochemical cells
US6927000B2 (en) 2001-12-14 2005-08-09 Rayovac Corporation Oxazoline surfactant anode additive for alkaline electrochemical cells
US20070048575A1 (en) * 2005-08-30 2007-03-01 Rovcal, Inc. Electrochemical cells containing spun mercury-amalgamated zinc particles having improved physical characteristics
US20070048576A1 (en) * 2005-08-30 2007-03-01 Rovcal, Inc. Electrochemical cells containing spun mercury-amalgamated zinc particles having improved physical characteristics
US20110070487A1 (en) * 2005-11-14 2011-03-24 Rovcal, Inc. Novel metal air cathode manganese oxide contained in octahedral molecular sieve
US9136540B2 (en) 2005-11-14 2015-09-15 Spectrum Brands, Inc. Metal air cathode manganese oxide contained in octahedral molecular sieve
US20070122709A1 (en) * 2005-11-30 2007-05-31 Rovcal, Inc. Ionically conductive clay additive for use in electrochemical cells
US20070122699A1 (en) * 2005-11-30 2007-05-31 Rovcal, Inc. Electrochemical cells having improved gelling agents
US7563537B2 (en) 2005-11-30 2009-07-21 Rovcal, Inc. Ionically conductive clay additive for use in electrochemical cells
EP2424016A1 (en) 2010-08-30 2012-02-29 Rovcal, Inc. Metal air cathode comprising manganese oxide contained in octahedral molecular sieve and Mn2O3
JP2015511239A (en) * 2012-02-17 2015-04-16 エピテック グループ エッセ．エッレ．エッレ． Compositions and methods for modulating amidases specific for N-acylethanolamines used in the treatment of inflammatory diseases

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