US2703795A - Quaternary ammonium compounds - Google Patents

Quaternary ammonium compounds Download PDF

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US2703795A
US2703795A US377247A US37724753A US2703795A US 2703795 A US2703795 A US 2703795A US 377247 A US377247 A US 377247A US 37724753 A US37724753 A US 37724753A US 2703795 A US2703795 A US 2703795A
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rosin
acids
acid
reaction
quaternary ammonium
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US377247A
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Carpenter Joseph Emmett
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Wyeth Holdings LLC
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American Cyanamid Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • 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
    • 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
    • Y10S516/905—Agent composition per se for colloid system making or stabilizing, e.g. foaming, emulsifying, dispersing, or gelling
    • Y10S516/914—The agent contains organic compound containing nitrogen, except if present solely as NH4+
    • Y10S516/915—The compound contains -C[=O]NHH where substitution may be made for the hydrogen

Definitions

  • This invention relates to novel quaternary ammonium compounds and to a process of preparing the same.
  • novel quaternary ammonium compounds may be represented by the following general formula:
  • R1 represents a hydrocarbon radical of a fatty acid containing at least 8 carbon atoms
  • R2 represents a Joseph Emmett Carpenter, Greenwich, COIIIL, assignor to hydrocarbon radical of a rosin acid
  • R3 and R4 are members of the group consisting of methyl and ethyl radicals
  • n is an integer having the values of 2 to 10, inclusive
  • X is a member of the group consisting of chlorine, bromine and iodine.
  • the new compounds are surface active agents and are highly useful as cationic flotation agents, textile assistate temperature of from about 120 C. to 300 C. with t the elimination of water to produce the amide condensate of the formula:
  • this fatty amide condensate is reacted with -a rosin acid and'aii epiha-lohydrin.
  • the epoxyiringsof the epihalohydrin opens and forms an ester linkage with the rosin acid, while simultaneously the ghailide reacts to form a quaternary ammonium salt with the tertiary amine group in the fatty amide, condensate.
  • the reaction in the second stage is exothermic and takes place spontaneously at an initial temperature of about 75 C., the temperature thereafter rising, usually to a little over 100 C. It is advisable, however, in order to insure completion of this reaction, to hold the reaction rnixture at about 100 C. for several hours, or at higher temperatures for shorter periods of time. Temperatures up to about 200 C. can be used, although dangenof discoloration and decomposition begins at about this point.
  • a variety of higher fatty acids or derivatives may be employed for reaction with the dialkyldiaminc.
  • the carbon chain length in the fatty acid is preferably from 8 to 30 carbon atoms, and the hydrocarbon chain may be saturated or unsaturated.
  • Representative higher fatty acids that may be used are lauric, palrnitic, stearic, oleic, ricinoleic, capric, myristic and mixtures of such acids.
  • the esters of these acids, particularly the esters from methanol, ethanol, glycol and glycerol can be advantageously used instead of the free acids. In such cases, the
  • rosin acids which may be used in the present process include abietic acid and its isomers, including hydrogenated and disproportionated types as well as the naturally occurring varieties, such as gum and wood rosin.
  • tall oil as the source of both the fatty acids and the rosin acids.
  • tall oil as produced as a Ivy-Product from sulfate paper manufacture, is composed of a mixture of rosin acids, fatty acids (principally oleic acid and linoleic acid), lignin and unsaponifiable matter. Crude tall oil generally contains a relatively large proportion of rosin acids, frequently as much as 50% rosin acids.
  • the quantity of dialkyldi'am-ine employed in the first step of the reaction is' chemically equivalent to the quantity of fatty acids in the-reaction mixture and, consequently, no difficulty is encountered in reacting substantially :all of the fatty acids while leaving substantially all of the rosin acids unreacted in the first .step,
  • rosin acidsof tall oil are isomers of abietic acid which have been formed in the heat treatment during the wood cooking process, and which are relatively inert.
  • anepihalohydrin whichis a very reactive chemical, to combine with the fatty amide condensate and with the rosin acids of tall oil in the second stage of reaction, it has been found that complete reaction of the rosin acids takes place very easily.
  • ester linkage once it has been formed by reaction of the rosin acids with the epihalohydrin, displays the same inertness and stability characteristics of the original. rosin acids. For this reason, hydrolysis of the ester linkage does not occur readily, and in applications where resistance to hydrolysis is of importance, the products of the present invention are about equally as stable as cationic surface active agents obtained from fatty acids and employing only amide linkages.
  • epihalohydrins which can be utilized to form the quaternary ammonium compounds of the present invention are epichlorohydrin, epibromohydrin, epiiodohydrin.
  • the products of this invention are also very suitable starting materials for the preparation of a large class of surface active agents in which the hydroxy group formed by the opening of the epoxy ring is reacted with other epoxy compounds, particularly ethylene oxide and propylfractionating column leading to a amine were reacted as in Example 1.
  • Example I 313.0 parts (1 eq.) of crude tall oil, (Saponification No. 179.3, Acid No. 166.0, Rosin Acid No. 89.4, corresponding to a content of 0.499 equivalent of rosin acids) and 54.0 parts (0.529 mol) of 3-dimethylam1nopropylamine were mixed and heated in a flask equipped with a distillation condenser. Distillation began at a pot temperature of 165 C., and the reaction was stopped after 30 minutes at a pot temperature of 207 C., at which point distillation of water was complete.
  • the fatty and rosin acids of hydrogenated tall oil show the same dilference in reactivity towardB-dirnethylammopropylamine as those of ordinary tall 011. Hydrogenated tall oil can be substituted for ordinary tall 011 with equal success.
  • Example 2 289.6 parts (1 eq.) of distilled tall oil (Saponification No. 193.7, Acid No. 188.0, Rosin Acid No. 55.0, corresponding to a content of 0.284 equivalent of rosin acids), and 73.0 parts (0.716 mol) of 3-dimethylaminopropyl-
  • the distillation began at 175 C. and the reaction was completed after 45 minutes at a final pot temperature of 250 C.
  • the intermediate amide product was found by potentiqmetrlc titration to contain 0.696 eq. of basic amino mtrogeg (0.340 eq.) of technical benzyl chloride were added in separate steps with cooling in between. The mixture was thereafter held at 135-147 C. for 1 hour to msurecompletion of the reaction.
  • the final product was a reddish solid on cooling, and dispersed in hot water giving a foamy solution.
  • Example 3 214.7 parts (1 eq.) of coconut oil (Saponification No. 261.3) and 116.2 parts (1 mol) of Z-diethylaminoethylamine are heated together under reflux ceased to take place, the final temperature being in excess of 230 C.
  • the 3-acylarnidoethyldiethylamine so produced is cooled and 302.0 parts (1 mol) of abietic acid are added, together with 134 parts tertiary butyl alcohol to serve as a solvent.
  • R1 represents a hydrocarbon radical of a fatty acid containing at least 8 carbon atoms
  • R2 represents a hydrocarbon radical of a rosin acid
  • R3 and R4 are members of the group consisting of methyl and ethyl radicals
  • n is an integer having the values of 2 to 10, inclusive
  • X is a member of the group consisting of chlorine, bromine and iodine, which comprises reacting a dialkyldiamine of the formula:
  • dialkyldiamine is S-dimethylaminopropylamine.

Description

2,703,795 QUATERNARY AMMONIUM coMroUNns American Cyanamid Company, New York, N. Y., a corporation of Maine No Drawing. Application August 2851953, Serial No. 377,247
4 Claims. (Cl. 260--97.5)
This invention relates to novel quaternary ammonium compounds and to a process of preparing the same.
The novel quaternary ammonium compounds may be represented by the following general formula:
wherein R1 represents a hydrocarbon radical of a fatty acid containing at least 8 carbon atoms, R2 represents a Joseph Emmett Carpenter, Greenwich, COIIIL, assignor to hydrocarbon radical of a rosin acid, R3 and R4 are members of the group consisting of methyl and ethyl radicals, n is an integer having the values of 2 to 10, inclusive, and X is a member of the group consisting of chlorine, bromine and iodine.
The new compounds are surface active agents and are highly useful as cationic flotation agents, textile assistate temperature of from about 120 C. to 300 C. with t the elimination of water to produce the amide condensate of the formula:
Ru RF-O O--NHC1.l':izn-N in which n, R1, R3 and R4 have the significance noted above. I I
In the second stage, this fatty amide condensate is reacted with -a rosin acid and'aii epiha-lohydrin. The epoxyiringsof the epihalohydrin opens and forms an ester linkage with the rosin acid, while simultaneously the ghailide reacts to form a quaternary ammonium salt with the tertiary amine group in the fatty amide, condensate. The reaction in the second stage is exothermic and takes place spontaneously at an initial temperature of about 75 C., the temperature thereafter rising, usually to a little over 100 C. It is advisable, however, in order to insure completion of this reaction, to hold the reaction rnixture at about 100 C. for several hours, or at higher temperatures for shorter periods of time. Temperatures up to about 200 C. can be used, although dangenof discoloration and decomposition begins at about this point.
A variety of higher fatty acids or derivatives may be employed for reaction with the dialkyldiaminc. The carbon chain length in the fatty acid is preferably from 8 to 30 carbon atoms, and the hydrocarbon chain may be saturated or unsaturated. Representative higher fatty acids that may be used are lauric, palrnitic, stearic, oleic, ricinoleic, capric, myristic and mixtures of such acids. The esters of these acids, particularly the esters from methanol, ethanol, glycol and glycerol can be advantageously used instead of the free acids. In such cases, the
respective alcohols will be liberated in the first-stage reaction with the diamine and will be removed from the reaction mixture or not depending on the r volatility. Consequently, mixtures of fatty acids and their glycerides .inbefore described.
2,703,795 Patented Mar. 8, 1955 such as those found in naturally occurring animal, vegetable and marine oils such as coconut oil, palm oil, cottonseed oil, linseed oil, soya bean oil, olive oil, peanut oil, fish oils, and fractions from the refining of these oils may be advantageously used.
The rosin acids which may be used in the present process include abietic acid and its isomers, including hydrogenated and disproportionated types as well as the naturally occurring varieties, such as gum and wood rosin.
In a preferred embodiment of the present invention, I prefer to use tall oil as the source of both the fatty acids and the rosin acids. As is known, tall oil, as produced as a Ivy-Product from sulfate paper manufacture, is composed of a mixture of rosin acids, fatty acids (principally oleic acid and linoleic acid), lignin and unsaponifiable matter. Crude tall oil generally contains a relatively large proportion of rosin acids, frequently as much as 50% rosin acids. Depending upon the extent of purification, it is possible to obtain various purified fractions of tall oil where the rosin content may run as low as 10% When tall oil is to be used as the source material of both fattyacids and rosin acids, I may use any grade of tall oil,
that is, crude, distilled or hydrogenated, provided that in those cases in which the mol per cent of rosin acids exceeds that of the fatty acids, it will usually be advantageous to provide enough additional fatty acid so that the proportion of fatty acid in the initial reaction mixture is equal to or exceeds that of the rosin acids.
When tall oil is used as a source of fatty acids as well as rosin acids, it is apparent that opportunity will be provided in the first stage of the reaction for the rosin acids as well as the fatty acids to react with the primary amino group of the diamine. It might be supposed that some rosin acids will be consumed in this reaction so that the composition of the final product will differ from that here- I have found, however, that such is not the case because the rosin acids are very much less reactive toward amines than are the fatty acids and, therefore, the latter will be consumed first. Moreover, in the usual andpreferred practice of this invention, the quantity of dialkyldi'am-ine employed in the first step of the reaction is' chemically equivalent to the quantity of fatty acids in the-reaction mixture and, consequently, no difficulty is encountered in reacting substantially :all of the fatty acids while leaving substantially all of the rosin acids unreacted in the first .step,
than ,would be expected from the corresponding reactions employing ,abietic acid and most commercial forms of rosin. The most plausible explanation appears to be that the rosin acidsof tall oil are isomers of abietic acid which have been formed in the heat treatment during the wood cooking process, and which are relatively inert. However, 'by the use of anepihalohydrin, whichis a very reactive chemical, to combine with the fatty amide condensate and with the rosin acids of tall oil in the second stage of reaction, it has been found that complete reaction of the rosin acids takes place very easily.
It is another advantage of this invention that the ester linkage, once it has been formed by reaction of the rosin acids with the epihalohydrin, displays the same inertness and stability characteristics of the original. rosin acids. For this reason, hydrolysis of the ester linkage does not occur readily, and in applications where resistance to hydrolysis is of importance, the products of the present invention are about equally as stable as cationic surface active agents obtained from fatty acids and employing only amide linkages.
Among the epihalohydrins which can be utilized to form the quaternary ammonium compounds of the present invention are epichlorohydrin, epibromohydrin, epiiodohydrin.
The products of this invention are also very suitable starting materials for the preparation of a large class of surface active agents in which the hydroxy group formed by the opening of the epoxy ring is reacted with other epoxy compounds, particularly ethylene oxide and propylfractionating column leading to a amine were reacted as in Example 1.
and 0.342 eq. of uncombined carboxylic acids. parts (0.356 eq.) of epichlorohydrin and 44.1 parts conjunction with the following specific examples in which the parts are by weight unless otherwise specified.
Example I 313.0 parts (1 eq.) of crude tall oil, (Saponification No. 179.3, Acid No. 166.0, Rosin Acid No. 89.4, corresponding to a content of 0.499 equivalent of rosin acids) and 54.0 parts (0.529 mol) of 3-dimethylam1nopropylamine were mixed and heated in a flask equipped with a distillation condenser. Distillation began at a pot temperature of 165 C., and the reaction was stopped after 30 minutes at a pot temperature of 207 C., at which point distillation of water was complete. Potentiometric titration of a sample of the amide intermediate with standard alcoholic HCl showed a basic amine content of 0.546 equivalent, nearly all of which was dirnethylamino nitrogen with only a very minor amount of primary amino nitrogen. Rotentiometric' titration of another sample with standard KOH in methanol showed a tree carboxylic acid content of 0.512 equivalent. 50.0 parts (0.530 eq.) of epichlorohydrin were added to the amide intermediate at 56 C., a
spontaneous reaction taking the temperature to 127 C.
in 8 minutes, but without causing refluxing of epichlorohydrin. The mixture was then heated at 154 160 for 1 hour, and on cooling produced a dark, sticky SOlld which dispersed in hot water, making a foamy solution.
.The fatty and rosin acids of hydrogenated tall oil show the same dilference in reactivity towardB-dirnethylammopropylamine as those of ordinary tall 011. Hydrogenated tall oil can be substituted for ordinary tall 011 with equal success.
. Example 2 289.6 parts (1 eq.) of distilled tall oil (Saponification No. 193.7, Acid No. 188.0, Rosin Acid No. 55.0, corresponding to a content of 0.284 equivalent of rosin acids), and 73.0 parts (0.716 mol) of 3-dimethylaminopropyl- The distillation began at 175 C. and the reaction was completed after 45 minutes at a final pot temperature of 250 C. The intermediate amide product was found by potentiqmetrlc titration to contain 0.696 eq. of basic amino mtrogeg (0.340 eq.) of technical benzyl chloride were added in separate steps with cooling in between. The mixture was thereafter held at 135-147 C. for 1 hour to msurecompletion of the reaction. The final product was a reddish solid on cooling, and dispersed in hot water giving a foamy solution. i
"Thisexample illustrates a situation very common in "practice in cases where the proportion of rosin acids in 'the tall oil employed is less than that of the fatty acids. Instead of adding more rosin acid, the proportion of epihalohydrin can be adjusted to the quantity of unre- -acted rosin acids present after the initial reaction, and there results a mixture consisting of the product of this example together with the surplus fatty amide condensate. While in some cases it is satisfactory to leave the surplus fatty amide condensate as it is, it will generally be preferred to convert it also to a quaternary ammonium salt, by reaction with benzyl chloride as shown, or with additional epihalohydrin or with any of the various other quaternizmg agents known to the art. The order of addition of the epihalohydrin and the other quaternizing agents is ordinarily immaterial, and they may also be added simultaneously.
Example 3 214.7 parts (1 eq.) of coconut oil (Saponification No. 261.3) and 116.2 parts (1 mol) of Z-diethylaminoethylamine are heated together under reflux ceased to take place, the final temperature being in excess of 230 C. The 3-acylarnidoethyldiethylamine so produced is cooled and 302.0 parts (1 mol) of abietic acid are added, together with 134 parts tertiary butyl alcohol to serve as a solvent. After the abietic acid has been dissolved by warming and again cooling to about 50 C., 137.0 parts (1 mol) of epibromohydrin is added, and following the temperature rise from spontaneous reaction, the mixture is heated to the reflux temperature of the tertiary butyl alcohol for several hours. The final prod uct has properties similar to the products of Examples 1 and 2.
I claim:
1. The process of preparing a quaternary ammonium compound of the following general formula:
until refluxing has wherein R1 represents a hydrocarbon radical of a fatty acid containing at least 8 carbon atoms, R2 represents a hydrocarbon radical of a rosin acid, R3 and R4 are members of the group consisting of methyl and ethyl radicals, n is an integer having the values of 2 to 10, inclusive, and X is a member of the group consisting of chlorine, bromine and iodine, which comprises reacting a dialkyldiamine of the formula:
/Ra HaN-C nHIn N with a fatty acid at a temperature of from about C. to 300 C. and then reacting the amide condensate so formed with a rosin acid and an epihalohydrin at a temperature not appreciably greater than 200 C.
2. The process according to claim 1 in which the fatty acid and rosin acid are derived from tall oil.
3. The process according to claim 2 in which the dialkyldiamine is S-dimethylaminopropylamine.
4. The process according to claim 2 in which the epihalohydrin is epichlorohydrin.
References Cited in the file of this patent UNITED STATES PATENTS 2,540,678 Kelley Feb. 6, 1951 2,636,028 Sommer et a1. Apr. 21, 1953 2,640,822 Harman et al- June 2, 1953

Claims (1)

1. THE PROCESS OF PREPARING A QUATERNARY AMMONIUM COMPOUND OF THE FOLLOWING GENERAL FORMULA: WHEREIN R1 REPRESENTS A HYDROCARBON RADICAL OF A FATTY ACID CONTAINING AT LEAST 8 CARBON ATOMS, R2 REPRESENTS A HYDROCARBON RADICAL OF A ROSIN ACID, R3 AND R4 ARE MEMBERS OF THE GROUP CONSISTING OF METHYL AND ETHYL RADICALS, N IS AN INTEGER HAVING THE VALUES OF 2 TO 10, INCLUSIVE AND X IS A MEMBER OF THE GROUP CONSISTING OF CHLORINE, BROMINE AND IODINE, WHICH COMPRISES REACTING A DIALKYLDIAMINE OF THE FORMULA:
US377247A 1953-08-28 1953-08-28 Quaternary ammonium compounds Expired - Lifetime US2703795A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2992994A (en) * 1954-07-20 1961-07-18 Ciba Ltd Detergent composition for the hair
US4405514A (en) * 1983-03-08 1983-09-20 The United States Of America As Represented By The Secretary Of Agriculture Preparation of esters of resin acids, resins, rosins, and derivatives thereof
US4994199A (en) * 1990-04-16 1991-02-19 Olin Corporation Antimicrobial composition containing quaternary aliphatic amine polyglycidol adducts

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2540678A (en) * 1946-12-06 1951-02-06 Nopco Chem Co Fatty acid alkylolamine condensation and products
US2636028A (en) * 1950-03-24 1953-04-21 Shell Dev Organic acid-polyamine adducts
US2640822A (en) * 1953-06-02 Acxljlted

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2640822A (en) * 1953-06-02 Acxljlted
US2540678A (en) * 1946-12-06 1951-02-06 Nopco Chem Co Fatty acid alkylolamine condensation and products
US2636028A (en) * 1950-03-24 1953-04-21 Shell Dev Organic acid-polyamine adducts

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2992994A (en) * 1954-07-20 1961-07-18 Ciba Ltd Detergent composition for the hair
US4405514A (en) * 1983-03-08 1983-09-20 The United States Of America As Represented By The Secretary Of Agriculture Preparation of esters of resin acids, resins, rosins, and derivatives thereof
US4994199A (en) * 1990-04-16 1991-02-19 Olin Corporation Antimicrobial composition containing quaternary aliphatic amine polyglycidol adducts

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