CA1163275A - Quaternary alkylamino-di-alkylcarboxylic acid di- esters, process for their manufacture and their use - Google Patents
Quaternary alkylamino-di-alkylcarboxylic acid di- esters, process for their manufacture and their useInfo
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- CA1163275A CA1163275A CA000355190A CA355190A CA1163275A CA 1163275 A CA1163275 A CA 1163275A CA 000355190 A CA000355190 A CA 000355190A CA 355190 A CA355190 A CA 355190A CA 1163275 A CA1163275 A CA 1163275A
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- 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
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
Quaternary alkylamino-di-alkylcarboxylic acid di-esters of the formula (1)
Quaternary alkylamino-di-alkylcarboxylic acid di-esters of the formula (1)
Description
i ~1 63~7~
Subject of the invention are quaternary alkylamino-di-alkylcarboxylic acid di-esters of the formula 1 1\ ~ ~(CH2)m-co-(o-cH2-cH) -O-R5 xe (1) R2 (CH2)n-CO-(O-CH2-CH)p-O-R6 wherein Rl and R2 are alkyl or hydroxyalkyl wlth from 1 to 4 C-atoms or benzyl, R3 and R4 are hydrogen or methyl, R5 and R6 are alkyl or alkenyl w.ith from 8 to 24 C-atoms, m and n are numbers from 1 to 4, o and p are numbers from 0 to 10 and X is a halogen, methosulfate, ethosulfate or alkylphosphate anion.
Preferred compounds of formula 1 are those, wherein Rl and R2 are alkyl or hydroxyalkyl with 1 or 2 C-atoms, R3 and R4 are hydrogen/ R5 and R6 are alkyl or alkenyl with from 16 to 22 C-atoms, X is Cle, Bre or CH3SO4e, m and n are 1 or 2 and o and p are numbers from 0 to 5.
Especially preferred are those compounds of formula 1, wherein Rl and R2 are methyl, R3 and R4 are hydrogen, R5 and R6 are C16-C22-alkyl, X is Cl , m and n are 1 and p and o are numbers from 0 to 2.
These compounds are manufactured by first reacting a compound of the formula 2 Rl\
R ~ ~2) with a compound of the formula 3 X~(cH2)m-co-(o-cH2-cH)o~O~R5 (3) f~.
~ ~ 6 3 .~
wherein X ~eans halogen. Thereby a compound of the formula R1\
N-(CH2) -CO-(oCH2C~H)o 5 is obtained, which subsequently is reacted further with a compound of the formula ~
X-(CH2)n-CO-lOcH2lcH)p OR6 The a~ine of the formula 2 could initially be reac-ted also with the halogenocarboxylic acid ester of the formula 4 and afterwards with the halogenocarboxylic acid ester of the formula 3. If the symbols m and n, o and p t R3 and R4 and R5 and R6 are identical, the compounds of the formulae 3 and 4 are also identical and the amine 2 will at first be reacted with half of the necessary amount of halogenocarboxylic acid ester and subsequently in the second stage with the other half.
In the first stage this reaction is carried out in an inert solvent, such as benzene, toluene, xylene or a paraf-fin hydrocarbon or their mixtures, at temperatures of about -20C to about 100C. The reaction vessel is first charged with the dialkylamine of the formula 2 in the solvent and intensively cooled. Subsequently, the halogenocarboxylic acid ester of the formula 3 is added and the temperature is slowly increased, whereby a possible excess of unreacted dialkylamine escapes For taking up the literated hydro-gen hallde an appropriate excess of the dialkylamine is used and the resulting ammonium salt is separated by filtration.
From this salt the dialkylamine can be regenerated and used a~ain. After distillation of the inert solvent the diaikyl-aminoalkane carbo~ylic acid ester is obtained with a puri-ty of more than 95 %. In the case of the dimethylaminoacetic acid esterr.the product can also be purified by high vacuum aistillation .
The dialkylaminoalkane carboxylic acid esters are sub-sequently dissolved in an alcohol or preferably dispersed in 3~75 water and reacted again with a halogenoalkane carboxylic acid ester of the formula 3 or 4, at temperatures below 100C, preferably at temperatures from 40 - 80C. The reaction, however, can also be performed without any sol-vent. ~fter distillation of water or the solvent, the purecompounds of the formula 1 are obtained. According to a preferred embodiment the reaction is carried out in an aqueous dispersion, whereby about 20 % of aqueous disper-sion of the compounds 1 are obtained which, after further dilution with water, can directly be used as fabric softe-ners.
Another possibility for manufacturing the compounds of formula 1 consists in first reacting 1 mol of a mono-alkylamine of the formula 5 R1 ~ NH2 (5) with 2 mols of a halogenoalkane carboxylic acid ester of the formula 3 or 4 and quaternizing the reaction product with a compound of the formula R2_Y or (R20)2S02 ~ in which Y means halogen. The reaction of the monoalkylamine with the halogenoalkane carboxylic esters is carried out under the same conditions as in the first stage of the above described process. For neutralizing the resulting hydrogen halide in this case a second amine is used, such as triethylamine or pyridine, and the resulting amine salt is separated by filtration, too. This reaction can also be carried out with a mixture of two different halo-genoalkane carboxylic acid esters of the formulae 3 and 4 or with 2 mols of only one of these compounds. The sub-sequent quaternization is carried out as above described 35 at about 40 - 100~C in an alcohol, but preferably in wa-ter with an alkyl halide or with a dlalkyl sulfate, which serves to introduc2 the radical R2 when the mDnoalkylam~e 5 already contains the radical R1. Vice versa, a monoalkyl-amine 5 which already contains the radical R2 can, of course, i ~ 6327~
- 5 - ~lo~ 79/~ 168 be used as staxtiny material ancl during the final quaterni-zation the radical R1 is then introduced. The quaterniza-tion can also be carried out wit:hout any solvent.
The~-halogenoalkane carboxylic acid esters of the formulae 3 and 4 used as starting materials, can be oh~
tained by known methods by reacting an acid of the for-mula X-(CH2)m-COOH or X-(CH2)n-cOOH
or the corresponding acid chloride with an oxalkylated alcohol of the formula H(OCH2CH)o-OR5 or H(ocH2cH)p-oR6 R R
Suitable alcohols are branched or unbranched, satura-ted or unsaturated alcohols with from 8 to 24 C-atoms, for example dodecyl, myristyl, cetyl, oleyl or preferably stearyl and behenyl alcohol or mixtures of those alcohols.
Because of economic reasons, mixtures of alcohols, ob-tained from natural fats on the basis of coco nut oil or tallow or in the form of distillation fractions of synthetic alcohols (Ziegler- or oxoalcohols) are preferred. Before the reaction with the halogeno carboxylic acid derivative, the alcohol is oxalkylated in known manner with propylene oxide or preferably with ethylene oxide.
The compounds of formula 1 according to the inven-tion can be used as fabric softeners and are added, after washing the textile material, into the last cleansing bath in the form of aqueous dispersions with a content of active substance from 1 to 15 % by weight, preferahly 4 to 10 ~ by weight of the compounds of formula 1. Subse-quently, the textile material is dried. These fabric sof-teners can also contain`othe~ substances and auxiliariesas generally used in fabric softeners. Such su~stances are, for example, cationic or non-lonic surface-active substances~
electrolytes, neutralizing agents, organic complexing agents, optical brighteners or dissolving intermediaries, as well as dyestuffs and perfumes. The products are used for an additional influencing of the fabric feel or of other pro-perties of the treated textiles or for adjusting the vis-cosity, the pH regulation or for improving the stability at low temperatures of the solutions.
The compounds according to the invention provide an agreable and smooth feel to any textile materials, especially those of natural or regenerated cellulose, wool, cellulose acetate, triacetate, polyamide, polyacrylo-nitrile, polyester, polypropylene. Of special advantage is the use as aftertreatment agent for friction cloth and lingerie.
The advantage of these compounds consists in that they are obtained in the form of aqueous dispersions, which, after further dilution, can directly be used, whilst the dialkyldimethylammonium salts, commonly used in practice for this purpose, in the preferred commercial form of a concentrated solution contain a combustible alcohol. There-fore, because of the low point of ignition these products fall within the regulations for dangerous working materials for transportation, storage and processing. Such a limita-tion does not exist for the compounds of the present inven-~ tion.
The following examples illustrate the invention:
Example 1:
410 parts by weight of a chloroacetic acid ester, manufactured from chloroacetyl chloride and a Ziegler al-cohol of the chain distribution of 60 % C20-alkyl and 40 ~
C22-alkyl are dissolved in 500 parts by weight of toluene and at 20C they are dropped to a solution of 220 parts by weight of dimethylamine in 250 parts by weight of toluene.
Stirring is continued for 5 hours at room temperature and subsequently for 3 hours at 70C. After cooling the preci-pitated dimethylamine hydrochloride is filtered off with suction and the - solvent is expelled in vacuo.
420 parts by weight of a yellowish oil are obtained. At 70C, 430 parts by weight of a chloroacetic acid ester, ~ ~ ~3 L ' 7 5 manufactured froM chloroacetyl chloride and a Ziegler alcohol of the chain distribution of 65 % C16-alkyl and 35 ~ C18-alkyl which before had been reacted with 2 mols ethylenc oxide, are added. While thoroughly stirring the mixture is poured into 3, 400 parts by weight of distilled water of 70C and stirring is continued for 15 hours at this temperature. After ~his time, no free amine can be observed. The chloride content is more than 9S % of the expected value. A 20 % white, stable, pourable disper-sion of a compound of the formula C~3 ~ /CH2-C--R5 Cl~3 CH3 CH2-C0-(0C~l2cH2)2 R6 R5 C20/C22 ~lkyl~ R6 = c16/C18-~lkyl is obtained. The pure compound can be obtained by distil- 0 lation of the water.
Example 2:
According to the process described in example 1, 340 parts by weight of a chloroacetic acid ester from a Ziegler alcohol with 65 ~ oE C16-alkyl and 35 ~ of C18-5 alkyl are reacted in 400 parts by weight of benzene with 220 parts by weight of dimethylamine in 250 parts by weigllt of benzene.
There are obtained 350 parts by weight of the corres-ponding dimethylaminoacetic acid ester which can be distilled at 150-170C at a pressure of 0.05 mbar. The product is reacted to a quaternary product with 340 parts of the C16(C18-chloracetic acid ester used before under the conditions indicated in example 1. A stable aqueous dis-persion of the compound of the formula C~J3 ~ C1I2-C0-OR5 ~ N\ Cl C~13 C~l~-C0-OR6 55 R6 = ~16/C1~-Alky]
is obtained.
By dis~illation of water, this compound can be ob-tained in pure form.
10Example 3:
Analoguously to example 2, 495 parts by weight of achloroaceticacid ester from an alcohol with 60 % C20-alkyl and 40 % C22-alkyl, whose alcohol component before had been reacted with 2 mols of ethylene oxide, 365 parts of diethylamine and again 495 parts of the same chloroacetic acid ester are reacted. The solvent used in the first reac-tion step is toluene, in the second water.
20 3 2 \ ~ / C~12C-(C~2C~12)~-0P~5 Cl~
C~3 2 \ C~2cO-(OC~l2C~)2 OR6 R5 = R6 = C20/
The isolation of the com~ound is ~erformed as indi-cated in example 2.
Exam~le 4:
340 parts by weight of a chloroacetic acid ester, produced from a native, hydrogenated tallow fatty alcohol of the chain distribution of 65 % C18-alkyl and 35 % of C16-alkyl, are reacted analogously to example 1 in 700 parts by weight of toluene with 220 parts by weiqht of dimethyl-amine in 250 parts of toluene. As q~terni~ation components there are used 385 parts by weight of chloroacetic acid ester of the same tallow fatty alco~ol which before, however, ~ ~ 63275 had been reacted with 1 mol of ethylene oxide. The qua-ternization is carried out in such an amount of water that a 20 ~ dispersion of the compound of the formula CH3 ~ CH2COOR5 Cl~
C1~3 \ Cl-l2Co-oc~l2cTl2 6 is obtained. The isolation of this compound is also per-formed by distillation of the water.
Example 5:
680 parts by weight of chloroacetic acid ester from an alcohol with 60 % of C20-alkyl and 40 % of C22-alkyl, whose alcohol component had been reacted with 2 mols of ethylene oxide in 1250 parts by weight of toluene, are dropped to a solution of 31 parts by weight of methylamine and 20~ parts by weight of triethylamine in 250 parts by weight of toluene at 20C. Stirring is continued for 1 hour at 20C and subsequently 7 hours at 60C, the pro-duct is filtered at 40C to separate the precipitated triethylamine hydr~chloride and the solvent is e~pelled in the vacuo. There are obtained 720 parts of crude methyl-iminodiacetic acid diester which is dispersed in 3,400 partsby weight of water of 50C while vigorously stirring.
126 parts of dimethyl sulfate are dropped into the pro-duct. The temperature of 70C should not be exceeded.
A 20 ~ stab]~ dispersion of the quaternary compound of the 30 formula CH3 ~ CH2-CO-(Oc~2c~l2)2-oR5 N C~130S03 C~13 Cll2-CO-(OCH2C~I2)2 OR6 R5 ~ ~6 = C20/C22-Alkyl ~ ~ ~3275 is obtained. The pure compound is also obtained by distil-lation of the water.
Subject of the invention are quaternary alkylamino-di-alkylcarboxylic acid di-esters of the formula 1 1\ ~ ~(CH2)m-co-(o-cH2-cH) -O-R5 xe (1) R2 (CH2)n-CO-(O-CH2-CH)p-O-R6 wherein Rl and R2 are alkyl or hydroxyalkyl wlth from 1 to 4 C-atoms or benzyl, R3 and R4 are hydrogen or methyl, R5 and R6 are alkyl or alkenyl w.ith from 8 to 24 C-atoms, m and n are numbers from 1 to 4, o and p are numbers from 0 to 10 and X is a halogen, methosulfate, ethosulfate or alkylphosphate anion.
Preferred compounds of formula 1 are those, wherein Rl and R2 are alkyl or hydroxyalkyl with 1 or 2 C-atoms, R3 and R4 are hydrogen/ R5 and R6 are alkyl or alkenyl with from 16 to 22 C-atoms, X is Cle, Bre or CH3SO4e, m and n are 1 or 2 and o and p are numbers from 0 to 5.
Especially preferred are those compounds of formula 1, wherein Rl and R2 are methyl, R3 and R4 are hydrogen, R5 and R6 are C16-C22-alkyl, X is Cl , m and n are 1 and p and o are numbers from 0 to 2.
These compounds are manufactured by first reacting a compound of the formula 2 Rl\
R ~ ~2) with a compound of the formula 3 X~(cH2)m-co-(o-cH2-cH)o~O~R5 (3) f~.
~ ~ 6 3 .~
wherein X ~eans halogen. Thereby a compound of the formula R1\
N-(CH2) -CO-(oCH2C~H)o 5 is obtained, which subsequently is reacted further with a compound of the formula ~
X-(CH2)n-CO-lOcH2lcH)p OR6 The a~ine of the formula 2 could initially be reac-ted also with the halogenocarboxylic acid ester of the formula 4 and afterwards with the halogenocarboxylic acid ester of the formula 3. If the symbols m and n, o and p t R3 and R4 and R5 and R6 are identical, the compounds of the formulae 3 and 4 are also identical and the amine 2 will at first be reacted with half of the necessary amount of halogenocarboxylic acid ester and subsequently in the second stage with the other half.
In the first stage this reaction is carried out in an inert solvent, such as benzene, toluene, xylene or a paraf-fin hydrocarbon or their mixtures, at temperatures of about -20C to about 100C. The reaction vessel is first charged with the dialkylamine of the formula 2 in the solvent and intensively cooled. Subsequently, the halogenocarboxylic acid ester of the formula 3 is added and the temperature is slowly increased, whereby a possible excess of unreacted dialkylamine escapes For taking up the literated hydro-gen hallde an appropriate excess of the dialkylamine is used and the resulting ammonium salt is separated by filtration.
From this salt the dialkylamine can be regenerated and used a~ain. After distillation of the inert solvent the diaikyl-aminoalkane carbo~ylic acid ester is obtained with a puri-ty of more than 95 %. In the case of the dimethylaminoacetic acid esterr.the product can also be purified by high vacuum aistillation .
The dialkylaminoalkane carboxylic acid esters are sub-sequently dissolved in an alcohol or preferably dispersed in 3~75 water and reacted again with a halogenoalkane carboxylic acid ester of the formula 3 or 4, at temperatures below 100C, preferably at temperatures from 40 - 80C. The reaction, however, can also be performed without any sol-vent. ~fter distillation of water or the solvent, the purecompounds of the formula 1 are obtained. According to a preferred embodiment the reaction is carried out in an aqueous dispersion, whereby about 20 % of aqueous disper-sion of the compounds 1 are obtained which, after further dilution with water, can directly be used as fabric softe-ners.
Another possibility for manufacturing the compounds of formula 1 consists in first reacting 1 mol of a mono-alkylamine of the formula 5 R1 ~ NH2 (5) with 2 mols of a halogenoalkane carboxylic acid ester of the formula 3 or 4 and quaternizing the reaction product with a compound of the formula R2_Y or (R20)2S02 ~ in which Y means halogen. The reaction of the monoalkylamine with the halogenoalkane carboxylic esters is carried out under the same conditions as in the first stage of the above described process. For neutralizing the resulting hydrogen halide in this case a second amine is used, such as triethylamine or pyridine, and the resulting amine salt is separated by filtration, too. This reaction can also be carried out with a mixture of two different halo-genoalkane carboxylic acid esters of the formulae 3 and 4 or with 2 mols of only one of these compounds. The sub-sequent quaternization is carried out as above described 35 at about 40 - 100~C in an alcohol, but preferably in wa-ter with an alkyl halide or with a dlalkyl sulfate, which serves to introduc2 the radical R2 when the mDnoalkylam~e 5 already contains the radical R1. Vice versa, a monoalkyl-amine 5 which already contains the radical R2 can, of course, i ~ 6327~
- 5 - ~lo~ 79/~ 168 be used as staxtiny material ancl during the final quaterni-zation the radical R1 is then introduced. The quaterniza-tion can also be carried out wit:hout any solvent.
The~-halogenoalkane carboxylic acid esters of the formulae 3 and 4 used as starting materials, can be oh~
tained by known methods by reacting an acid of the for-mula X-(CH2)m-COOH or X-(CH2)n-cOOH
or the corresponding acid chloride with an oxalkylated alcohol of the formula H(OCH2CH)o-OR5 or H(ocH2cH)p-oR6 R R
Suitable alcohols are branched or unbranched, satura-ted or unsaturated alcohols with from 8 to 24 C-atoms, for example dodecyl, myristyl, cetyl, oleyl or preferably stearyl and behenyl alcohol or mixtures of those alcohols.
Because of economic reasons, mixtures of alcohols, ob-tained from natural fats on the basis of coco nut oil or tallow or in the form of distillation fractions of synthetic alcohols (Ziegler- or oxoalcohols) are preferred. Before the reaction with the halogeno carboxylic acid derivative, the alcohol is oxalkylated in known manner with propylene oxide or preferably with ethylene oxide.
The compounds of formula 1 according to the inven-tion can be used as fabric softeners and are added, after washing the textile material, into the last cleansing bath in the form of aqueous dispersions with a content of active substance from 1 to 15 % by weight, preferahly 4 to 10 ~ by weight of the compounds of formula 1. Subse-quently, the textile material is dried. These fabric sof-teners can also contain`othe~ substances and auxiliariesas generally used in fabric softeners. Such su~stances are, for example, cationic or non-lonic surface-active substances~
electrolytes, neutralizing agents, organic complexing agents, optical brighteners or dissolving intermediaries, as well as dyestuffs and perfumes. The products are used for an additional influencing of the fabric feel or of other pro-perties of the treated textiles or for adjusting the vis-cosity, the pH regulation or for improving the stability at low temperatures of the solutions.
The compounds according to the invention provide an agreable and smooth feel to any textile materials, especially those of natural or regenerated cellulose, wool, cellulose acetate, triacetate, polyamide, polyacrylo-nitrile, polyester, polypropylene. Of special advantage is the use as aftertreatment agent for friction cloth and lingerie.
The advantage of these compounds consists in that they are obtained in the form of aqueous dispersions, which, after further dilution, can directly be used, whilst the dialkyldimethylammonium salts, commonly used in practice for this purpose, in the preferred commercial form of a concentrated solution contain a combustible alcohol. There-fore, because of the low point of ignition these products fall within the regulations for dangerous working materials for transportation, storage and processing. Such a limita-tion does not exist for the compounds of the present inven-~ tion.
The following examples illustrate the invention:
Example 1:
410 parts by weight of a chloroacetic acid ester, manufactured from chloroacetyl chloride and a Ziegler al-cohol of the chain distribution of 60 % C20-alkyl and 40 ~
C22-alkyl are dissolved in 500 parts by weight of toluene and at 20C they are dropped to a solution of 220 parts by weight of dimethylamine in 250 parts by weight of toluene.
Stirring is continued for 5 hours at room temperature and subsequently for 3 hours at 70C. After cooling the preci-pitated dimethylamine hydrochloride is filtered off with suction and the - solvent is expelled in vacuo.
420 parts by weight of a yellowish oil are obtained. At 70C, 430 parts by weight of a chloroacetic acid ester, ~ ~ ~3 L ' 7 5 manufactured froM chloroacetyl chloride and a Ziegler alcohol of the chain distribution of 65 % C16-alkyl and 35 ~ C18-alkyl which before had been reacted with 2 mols ethylenc oxide, are added. While thoroughly stirring the mixture is poured into 3, 400 parts by weight of distilled water of 70C and stirring is continued for 15 hours at this temperature. After ~his time, no free amine can be observed. The chloride content is more than 9S % of the expected value. A 20 % white, stable, pourable disper-sion of a compound of the formula C~3 ~ /CH2-C--R5 Cl~3 CH3 CH2-C0-(0C~l2cH2)2 R6 R5 C20/C22 ~lkyl~ R6 = c16/C18-~lkyl is obtained. The pure compound can be obtained by distil- 0 lation of the water.
Example 2:
According to the process described in example 1, 340 parts by weight of a chloroacetic acid ester from a Ziegler alcohol with 65 ~ oE C16-alkyl and 35 ~ of C18-5 alkyl are reacted in 400 parts by weight of benzene with 220 parts by weight of dimethylamine in 250 parts by weigllt of benzene.
There are obtained 350 parts by weight of the corres-ponding dimethylaminoacetic acid ester which can be distilled at 150-170C at a pressure of 0.05 mbar. The product is reacted to a quaternary product with 340 parts of the C16(C18-chloracetic acid ester used before under the conditions indicated in example 1. A stable aqueous dis-persion of the compound of the formula C~J3 ~ C1I2-C0-OR5 ~ N\ Cl C~13 C~l~-C0-OR6 55 R6 = ~16/C1~-Alky]
is obtained.
By dis~illation of water, this compound can be ob-tained in pure form.
10Example 3:
Analoguously to example 2, 495 parts by weight of achloroaceticacid ester from an alcohol with 60 % C20-alkyl and 40 % C22-alkyl, whose alcohol component before had been reacted with 2 mols of ethylene oxide, 365 parts of diethylamine and again 495 parts of the same chloroacetic acid ester are reacted. The solvent used in the first reac-tion step is toluene, in the second water.
20 3 2 \ ~ / C~12C-(C~2C~12)~-0P~5 Cl~
C~3 2 \ C~2cO-(OC~l2C~)2 OR6 R5 = R6 = C20/
The isolation of the com~ound is ~erformed as indi-cated in example 2.
Exam~le 4:
340 parts by weight of a chloroacetic acid ester, produced from a native, hydrogenated tallow fatty alcohol of the chain distribution of 65 % C18-alkyl and 35 % of C16-alkyl, are reacted analogously to example 1 in 700 parts by weight of toluene with 220 parts by weiqht of dimethyl-amine in 250 parts of toluene. As q~terni~ation components there are used 385 parts by weight of chloroacetic acid ester of the same tallow fatty alco~ol which before, however, ~ ~ 63275 had been reacted with 1 mol of ethylene oxide. The qua-ternization is carried out in such an amount of water that a 20 ~ dispersion of the compound of the formula CH3 ~ CH2COOR5 Cl~
C1~3 \ Cl-l2Co-oc~l2cTl2 6 is obtained. The isolation of this compound is also per-formed by distillation of the water.
Example 5:
680 parts by weight of chloroacetic acid ester from an alcohol with 60 % of C20-alkyl and 40 % of C22-alkyl, whose alcohol component had been reacted with 2 mols of ethylene oxide in 1250 parts by weight of toluene, are dropped to a solution of 31 parts by weight of methylamine and 20~ parts by weight of triethylamine in 250 parts by weight of toluene at 20C. Stirring is continued for 1 hour at 20C and subsequently 7 hours at 60C, the pro-duct is filtered at 40C to separate the precipitated triethylamine hydr~chloride and the solvent is e~pelled in the vacuo. There are obtained 720 parts of crude methyl-iminodiacetic acid diester which is dispersed in 3,400 partsby weight of water of 50C while vigorously stirring.
126 parts of dimethyl sulfate are dropped into the pro-duct. The temperature of 70C should not be exceeded.
A 20 ~ stab]~ dispersion of the quaternary compound of the 30 formula CH3 ~ CH2-CO-(Oc~2c~l2)2-oR5 N C~130S03 C~13 Cll2-CO-(OCH2C~I2)2 OR6 R5 ~ ~6 = C20/C22-Alkyl ~ ~ ~3275 is obtained. The pure compound is also obtained by distil-lation of the water.
Claims (5)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Quaternary alkylamino-di-alkylcarboxylic acid-diesters of the formula 1 (1) wherein R1 and R2 are alkyl or hydroxyalkyl with from 1 - 4 C-atoms or benzyl, R3 and R4 are hydrogen or methyl, R5 and R6 are alkyl or alkenyl with from 8 to 24 C-atoms, m and n are numbers from 1 to 4, o and p are numbers from 0 to 10 and X is a halogen, methosulfate, ethosulfate, or alkylphosphate anion.
2. Compounds of formula 1 according to claim 1, wherein R1 and R2 are alkyl or hydroxyalkyl with 1 or 2 C-atoms, R3 and R4 are hydrogen, R5 and R6 are alkyl or alkenyl with from 16 to 22 C-atoms, X is Cl-, Br- or CH3SO4-, m and n are 1 or 2, and o and p are numbers from 0 to 5.
3. Compounds of formula 1, according to claim 1, wherein R1 and R2 are methyl, R3 and R4 are hydrogen, R5 and R6 are C10-C22-alkyl, X is C1-, m and n are 1, and p and o are numbers from 0 to 2.
4. A process for the manufacture of quaternary esters of formula 1 as defined in claim 1, which comprises (a) reacting a compound of formula (2) with a compound of the formula (3) and subsequently reacting the product with a compound of formula (4) wherein X in formulae 3 and 4 represents halogen; or (b) for the preparation of compounds of formula 1 wherein X
is halogen, methosulfate or ethosulfate, reacting 1 mol of a compound of the formula with 2 mols of a compound of the formula or and subsequently quaternating the reaction product with a compound of the formula R2-Y, wherein Y is halogen to produce a compound of formula 1, or with dimethylsulfate or diethylsulfate to produce a compound of formula 1 wherein X is methosulfate or ethosulfate.
is halogen, methosulfate or ethosulfate, reacting 1 mol of a compound of the formula with 2 mols of a compound of the formula or and subsequently quaternating the reaction product with a compound of the formula R2-Y, wherein Y is halogen to produce a compound of formula 1, or with dimethylsulfate or diethylsulfate to produce a compound of formula 1 wherein X is methosulfate or ethosulfate.
5. Method for softening fabrics which comprises contacting said fabrics with an aqueous dispersion of a compound of formula 1 as defined in claim 1, and thereafter drying said fabric.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792926772 DE2926772A1 (en) | 1979-07-03 | 1979-07-03 | QUATERNAERE ALKYLAMINO-DI-ALKYLCARBONÄSURE-DI-ESTER, METHOD FOR THE PRODUCTION AND USE THEREOF |
| DEP2926772.9 | 1979-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1163275A true CA1163275A (en) | 1984-03-06 |
Family
ID=6074773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000355190A Expired CA1163275A (en) | 1979-07-03 | 1980-07-02 | Quaternary alkylamino-di-alkylcarboxylic acid di- esters, process for their manufacture and their use |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0021431B1 (en) |
| JP (1) | JPS5610153A (en) |
| AR (1) | AR221425A1 (en) |
| AT (1) | ATE3971T1 (en) |
| BR (1) | BR8004135A (en) |
| CA (1) | CA1163275A (en) |
| DE (2) | DE2926772A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5476597A (en) * | 1993-09-10 | 1995-12-19 | Kao Corporation | Liquid softener composition, novel quaternary ammonium salt, and process for the preparation of said salt |
| US5916863A (en) * | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
| US5919750A (en) * | 1997-07-24 | 1999-07-06 | Akzo Nobel Nv | Fabric softener composition |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2188653A (en) * | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
| SE9001862D0 (en) * | 1990-05-23 | 1990-05-23 | Berol Nobel Ab | NEW NUCLEAR CONTAINING SOCIETIES, PROCEDURES FOR THEIR PREPARATION AND USE OF SOCIETIES |
| JPH08501074A (en) * | 1992-06-10 | 1996-02-06 | ザ、プロクター、エンド、ギャンブル、カンパニー | Stable biodegradable fabric softening compounds and compositions |
| ES2107118T3 (en) * | 1994-08-29 | 1997-11-16 | Akzo Nobel Nv | PROCEDURE FOR THE PREPARATION OF QUATERNARY DIESTERS. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1950643A1 (en) * | 1969-10-08 | 1971-04-15 | Manzke Oswald Dr Dipl Chem | Quaternary ammonium betaine ester derivs - for body care and cosmetic products |
| DE2741340A1 (en) * | 1976-09-24 | 1978-03-30 | Sandoz Ag | POLYAETHERS CONTAINING QUATERIAL AMINOGRAPHS AND THE PROCESS FOR THEIR MANUFACTURING |
| DE2805239A1 (en) * | 1978-02-08 | 1979-08-09 | Sandoz Ag | Polyetherester(s) contg. quaternary amino gps. - for use as dyeing aids with cationic dyes |
-
1979
- 1979-07-03 DE DE19792926772 patent/DE2926772A1/en not_active Withdrawn
-
1980
- 1980-06-26 EP EP80103619A patent/EP0021431B1/en not_active Expired
- 1980-06-26 DE DE8080103619T patent/DE3063964D1/en not_active Expired
- 1980-06-26 AT AT80103619T patent/ATE3971T1/en not_active IP Right Cessation
- 1980-07-01 AR AR281606A patent/AR221425A1/en active
- 1980-07-02 CA CA000355190A patent/CA1163275A/en not_active Expired
- 1980-07-02 JP JP8929280A patent/JPS5610153A/en active Pending
- 1980-07-03 BR BR8004135A patent/BR8004135A/en unknown
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5476597A (en) * | 1993-09-10 | 1995-12-19 | Kao Corporation | Liquid softener composition, novel quaternary ammonium salt, and process for the preparation of said salt |
| US5580481A (en) * | 1993-09-10 | 1996-12-03 | Kao Corporation | Aqueous fabric softener composition, novel quaternary ammonium salt, and process for the preparation of said salt |
| US5916863A (en) * | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
| US6004913A (en) * | 1996-05-03 | 1999-12-21 | Akzo Nobel N.V. | High di(alkyl fatty ester) quaternary ammonium compound in esteramine from triethanolamine |
| US6037315A (en) * | 1996-05-03 | 2000-03-14 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions |
| US6323167B1 (en) | 1996-05-03 | 2001-11-27 | Akzo Nobel N.V. | High di(alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions |
| US6770608B2 (en) | 1996-05-03 | 2004-08-03 | Akzo Nobel N.V. | High di(alkyl fatty ester) amines and quaternary ammonium compounds derived therefrom |
| US5919750A (en) * | 1997-07-24 | 1999-07-06 | Akzo Nobel Nv | Fabric softener composition |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0021431B1 (en) | 1983-06-29 |
| EP0021431A3 (en) | 1981-10-21 |
| DE2926772A1 (en) | 1981-01-15 |
| EP0021431A2 (en) | 1981-01-07 |
| ATE3971T1 (en) | 1983-07-15 |
| DE3063964D1 (en) | 1983-08-04 |
| BR8004135A (en) | 1981-01-21 |
| AR221425A1 (en) | 1981-01-30 |
| JPS5610153A (en) | 1981-02-02 |
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