CA2044234A1

CA2044234A1 - Poly(oxyalkylene)aminoalkanol esters, ammonium compounds thereof, process for producing them, and their use in emulsifiers, detergents, disinfectants and preservatives

Info

Publication number: CA2044234A1
Application number: CA002044234A
Authority: CA
Inventors: Axel Euler; Hans-Jurgen Kohle; Hans-Georg Schiesser; Winfried Wehner; Joachim Weigand
Original assignee: Rewo Chemische Werke GmbH
Current assignee: Rewo Chemische Werke GmbH
Priority date: 1990-06-12
Filing date: 1991-06-10
Publication date: 1991-12-13
Also published as: DE4018750A1; EP0461419A1

Abstract

ABSTRACT

The invention relates to poly(oxyalkylene)-aminoalkanol esters, ammonium compounds thereof, a process for producing them, and their use in emulsifiers, detergents, disinfectants and preservatives based on compounds of the general formula where R5 may be a group, or -OH, or -O-R6, R6 may be an alkyl group having from 1 to 5 carbon atoms or a group, R1, R2, R9 and R10 may be, independently of one another, hydrogen, an alkyl group having from 1 to 5 carbon atoms, or a group, 2510:CHS2510 R11 may be a hydrocarbon group having from 6 to 21 carbon atoms which optionally is branched and optionally contains multiple bonds or hydroxyl groups, with the proviso that at least one of the groups R1, R2, R9 and R10 must be the group , R3, R4, R7 and R8 may be, independently of one another, H or CH3, R12 and R13 may be, independently of one another, H, CH3, -C2H5 or a benzyl group, and k and l are from 0 to 1, k + l is from 0 to 2, a + c is from 1 to 40, b is from 0 to 40, d + e + f + g is from 2 to 12, and y? is a mono- or polyvalent anion having a total of k + 1 negative charges.

2510:CHS2510

Description

204423~

The invention relates to poly(oxyalkylene)-aminoalkanolamine esters of the general formula r l3 (Rl2)1~ --¦
R -~o-C ~-C}~2~ CH3 C1~3 ~ -C ~-CH2-~0- C~-CH2~a-~0-C~2-C~2-)bR (1) R2 _ ( o -C ~ -Cl~z ) "--0 L R~ _ (~1 )Y

Y~r~ R5 nay ba a (R~3) R7 C~ 3_ 1 ~ ( C~2- CX-O ~ -R9 _(o-c~z-c ~ c ~ CH2-CI~-o-~g RD

group or -OH or -o-R6, R6 may be an alkyl group having from 1 to 5 carbon atoms, or a -C-R11 group, o and where R1, R2, R9 and R10 may be, independently of one another, hydrogen, an alkyl group having from 1 to 5 carbon atoms, and preferably CH3, or a C- R11 group, R11 may be a hydrocarbon group having from 6 to 21, and preferably from 7 to 17, carbon atoms which is optionally branched and optionally contains multiple bonds or hydroxyl groups, with the proviso that at least one of the groups R1, R2, R9 and R10 must be the group 2510:CHS2510 -C-Rll, and R3, R4, R7 and R8 may be, independently of one another, H or CH3, and R12 and R13 may be, independently of one another, H, CH3, C2Hs or a benzyl group, k and l are from 0 to 1, k + l is from 0 to 2, a + c is from 1 to 40, and preferably from 1 to 15, b is from 0 to 40, and preferably from 0 to 15, d + e + f + g is from 2 to 12, and y~ is a mono- or polyvalent anion, and preferably a lactate, methosulfate, sulfate or chloride with a total of k + 1 negative charges.
The invention also relates to a process for producing these compounds and their use in the production of emulsifiers, detergents and disinfectants.
The following amino compounds of formulas (2) and (3) may be used as starting compounds to produce the ester amines:

CIH3 l~3 H2~-CH-CH2-~PO~a-(EO)b-(P0)C-cH2- CH ~H2 (2) c~3 ~2N-C~-c~2-(Po)~ o)b-(~o)c-o R

2510:CMS2510 2~4234 CH

where Po is -(O-CH2-CH) and EO is -(O-CH2-CH2)-, a is 0 to 20, c is 0 to 20, and a, c, b and R6 have the meanings given above, R6 being more particularly an alkyl group having from 1 to 5 carbon atoms, and c being 0.
These products are produced commercially and are generally obtained by known processes by reacting polyoxyalkylene alcohols with ammonia under pressure.
Polyoxyalkylene alcohols are typically prepared by the addition of an alkylene oxide, especially propylene oxide, ethylene oxide or a mixture of the two, by a conventional method to a compound which contains one or more active hydrogen atoms, or by polymerization of alkylene oxides.
Illustrative of compounds containing one or more active hydrogen atoms are monohydric alcohols such as ethanol, isopropanol, butanol, lauryl alcohol, stearyl alcohol, and particularly methanol, or glycols such as ethylene glycol, propylene glycol, diethylene glycol, glycerol, trimethylolpropane, pentaerythritol, sorbitol, polyglycerol, and polyvinyl alcohols.
The polyoxyalkylene alcohols have molecular weights ranging from about 100 to 10,000, and preferably from about 150 to 5,000, and most preferably from about 150 to 2,000.
The further reaction to give amines is carried out typically by conventional methods through aminolysis of the free hydroxyl groups or their esters, particularly the sulfates. In the case of higher alcohols, the -OH
group is exchanged for the amino group by means of homogeneous catalysis, and especially of heterogeneous 2510:CMs2510 204423~

catalysis on solid catalysts. For this purpose, at least two methods in particular are available. One employs dehydrating catalysts, and the other, catalysts having hydrogenating/dehydrogenating action.
Alumina with up to about 20% of chromic oxide, stannous oxide, zinc oxide or ferric oxide is used as catalyst.
Alumina deposited on silica gel or activated charcoal is suitable for the conversion at atmospheric pressure of higher fatty alcohols to fatty amines, for example. (See British patent 384,714 and U. S. patents 2,017,051 and 2,078,922.) Acids of aluminum phosphate, or phosphoric acids, either as such or on supports such as silica gel or diatomaceous earth (U. S. patent 2,073,671), are frequently used in production at standard or elevated pressure (U.S. patent 2,043,965). The operating temperatures range from 200 to 600C, depending on the catalyst. The literature is replete with data on the effect of temperature and pressure, on an excess of ammonium, and on the necessary residence times. (See, for example, Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag, Stuttgart 1957, vol. II/1, p. 108 et seq.) In accordance with the invention, the following compounds are preferred:
Of formula (2), a + c = 2 - 6 (I) b = 0 or a + c = 2 - 3 (II) b = 6 - 9 2510:CMS2510 20~4234 and of formula (3), a + c = 6 - 10 ~III) b = 1 - 2 R6 = -CH3 The compounds of formulas (2) and t3) are then alkoxylated, and preferably ethoxylated or propoxylated, typically by conventional methods. The usual procedure is to react the amines in a pressurized reactor at between 120 and 160 C, optionally in the presence of basic, and more particularly alkaline, catalysts at from 1 to 4 bars with a quantity of alkylene oxide correspond-ing to the desired degree of alkoxylation, ethylene oxide and propylene oxide or mixtures thereof being preferred in accordance with the invention.
What is obtained are compounds of the general formulas H-tO-CH-CH2)d \ ~ CH2CH-O)f H
~-cH-c~2-A-c~2-c~-N (4 ~_(O-C~~c~{z)e -- (CH2CH~O)g~H

and CI~3 ~-(o-c~-cHz~a ~~

~-C~-CH2-A-O-R6 ( 5 H- ( O -C~-CH2 ~ e I

R~

2510:CMs2510 where A is ~(Po)a-(Eo)b-(po)c~ and where a, b and c, and R6, EO and PO, all have the same meaning as above and d + e + f ~ g = 2-12, and R3 R4 R7 and R8 = H
and, independently of each other, may be H or CH3.
Preferred compounds of formula (4) are compounds where d + e + f + g = 4-6, and (IV) R3, R4, R7 and R8 = H
and preferred compounds of formula (5) are compounds where d + e = 2-3 (V) R3 and R4 = H
The subsequent esterification of the compounds (4) or (5) with carbonic acids or derivatives thereof gives compounds of the general formulas R -(O-C~I-CH2~d \ I 1 3 ~CII2-CH-O)~--R9 N-CX-CH2--A-C~2- C~-N~ ( 6 ( C~2-C~-0 )g-Rl R2- ( O -CH-CE., ), 1 8 and 7 CH3 ( Rl-~O-Cx-c~2)~ \N_CH_c}I2-A-o-R

1~. --(o--c~-cx2)~
l4 2510:C~IS2510 204~234 here a, b, c, d, e, f and g, R3, R4 R7 R8 and R6 A have the same meaning as above and R1, R2, R9 and R10 are, independently of one another, hydrogen, an alkyl group having from 1 to 5 carbon atoms, or a -C-R11 group, R11 being a hydrocarbon group, optionally branched, and optionally containing multiple bonds or hydroxyl groups, having from 6 to 21, and preferably from 7 to 17, carbon atoms, with the proviso that at least one of the groups Rl, R2, R9 and R10 must be a -C-R11 group.

15 Fatty acids which are suitable for esterification or transesterification are the monobasic synthetic fatty acids known and commonly used in this field, and especially the fatty acids based on natural plant and animal oils having from 6 to 22, and more particularly from 8 to 18, carbon atoms, such as those derived from coconut oil, palm oil, tallow, and castor oil. These may be used as glycerides, as esters with short-chain alcohols, or as free acids.
Their esterification or transesterification is carried out by the known method.
The alkanolamines are thus reacted at from 160 to 240C with a quantity of fatty acid or fatty acid ester corresponding to the desired degree of esterification, optionally in the presence of a catalyst, and the water of reaction or the alcohol is continuously distilled off, a vacuum being applied if necessary to complete the reaction.
Preferred compounds of formula (6) are substances where 2510:CMs2510 2~44234 R1, R , R , R , = 2 x H
2 X -C-R11 (VI) o R11 being C17H35, and preferred compounds of formula (7), are where R1 = H
R2 = C-R11 (VII) R11 being C17H35.
The quaternization or the preparation of the salts of the compounds of formulas (6) and (7) typically are carried out by methods known in this field and yields the inventive ester amine quaternary ammonium or ester amine salts of the general formula (1), where R12 and R13 have the meanings indicated, k and 1 are greater than zero, and k + 1 preferably has values between 0.5 and 2.
As a general rule, the salts are prepared by adding the acids, optionally as aqueous or alcoholic solutions, in a quantity corresponding to the desired degree of salt formation at 20-80C with vigorous stirring, and optionally with cooling, in portions to the poly(oxyalkylene)alkanolamine esters introduced as initial charge. The quaternization is carried out by one of the generally known methods, the poly(oxyalkylene)-alkanolamine esters being heated to 40-80C, optionally with the concurrent use of a solvent, and reacted in portions with the quaternizing agent in a quantity corre-sponding to the desired degree of quaternization.

2510:C~IS2510 Suitable anions which are preferred thus are:

o o Il 11 CH--O --S --O~ CE~3CHz --O --S --O . HCOO . CH3COO
O o C~ 3 --C~ --C OO ~ , O ~C~ 2COO ~ , ~ OO C --C ~ --C ~ --C O O ~
OH OH OH OH

OOC --CH--CH2 --COO . OOCCH2 --C--CH2 --COO , C6H5C
0~ COo OOC --(CIIz~n --COO , Cl, Br, J, 5o42, PO93 and ~O3, here n = O - 10.

Particularly preferred anions in accordance with the 2 0 invention are the anions o Cl-, S042-, C~9 --O --S --O~ and~r C~{3 --C~ --COO-O OK

Several anions may be present adjacent to one another.
The inventive compounds of the general formulas (6) and (7) may be used as components in the production of polyesters, polyester amides, polyurethanes or polyepoxies, which find use as flexible coatings, molded articles, sealing compounds and fiber-reinforced composite materials.

2510:CMS2510 20~4234 They are also of advantaqe in the formulation of emulsifiers for use in agriculture, metalworking, and to some extent in cosmetics.
The inventive compounds of the general formula (1) with k + 1 > 0 find use especially as antimicrobial agents. They are suitable for use as preservatives or disinfectants for all kinds of commercial products used in crop protection, agriculture and cosmetics.
They further lend themselves to the preservation of glues, surface coatings or paints based on organic vehicles. They can also be used as wood preservatives.
By combining the compounds of the general formula (1) with surface-active substances, washing and cleaning agents having antibacterial action are obtained which can be used as antimicrobial textile finishes.
The analytical methods used in the examples which follow are those commonly employed in this field.
1 Total amine value and tertiary amine value .

The total amine value gives the number of milligrams of potassium hydroxide equivalent to the total amine basicity of 1 gram of the amino compound (mg KOH/g). The tertiary amine value gives the number of milligrams of potassium hydroxide equivalent to the tertiary amine basicity of 1 gram of the amino compound.
The values are determined by A.O.C.S. Official Nethod Tf 2a - 64.
2. Sa~onification value The saponification value is a measure of the free and combined acids in fats and commercial fatty acids. It gives the number of milligrams of potassium hydroxide required for the complete saponification of 1 gram of fat or commercial fatty acid.

2510:CMS2510 204~234 The values are determined by the unit methods of Deutsche Gesellschaft fur Fettchemie (DGF) (German Society for Fat Chemistry), DGF C-V3.

3. Hydroxyl value The hydroxy value is used to determine the hydroxyl-group content and gives the number of milligrams of potassium hydroxide required to neutralize the acetic acid consumed by 1 gram of fat in acetylation (mg KOHtg).
The values are determined by DGF unit method C-V17a.

4. Acid value The acid value is a measure of the free-acid content of a fat or of commercial fatty acids and gives the milligrams of potassium hydroxide required to neutralize 1 gram of substance.
The values are determined by DGF unit method C-V4.

5. Content of cation-active substance. Cat S03 This method is used to determine the content of cation-active substances. Cation-active substances here are short- and long-chained compounds containing primary, secondary and tertiary amino groups or ammonium groups.
The content is expressed as S03 per 100 g of the substance being tested.
The content is determined by two-phase titration in conformity with IS0 standards 2871-1 and 2871-2 (1988 edition).

2sl0~ s2510 EXAMPLES
(I) Preparation of hYdroxYlamines of the qeneral formulas ~4) and (5) Example 1 912 g (2 mols) of an amine of the general formula ~2) with a + c = 6.6 b = 0 was mixed in an autoclave at 145-160 C in portions with 352 g (8 mols) of ethylene oxide so that the pressure was maintained at between 1 and 3 bars. After the amount of ethylene oxide added had been reacted, 1,264 g of a clear liquid of the general formula (4), with a + c = 6.6 b = 0 a + e + f + d = 4 and R3, R4, R7 R8 = H
was obtained.
This compound had a total amine value of 179 mg KOH/g, a tertiary amine value of 175 mg KOHlg, and a hydroxyl value of 348 mg KOH/g.

Exam~le 2 912 g (2 mols) of an amine of the general formula ~2) with a + c = 6.6 b = 0 was alkylated in an autoclave at 145-160 C in portions with 352 g (8 mols) of ethylene oxide so that the pressure was maintained at between 1 and 3 bars. After the ethylene oxide added had been reacted, 0.2 g of KOH
was added to the reaction mixture, and then another 352 g (8 mols) of ethylene oxide was added as described above 2510:CM52510 and reacted. 1,616 g of a clear liquid of the general formula (4), with a + c = 6.6 b = 0 5d + e + f + g = 8 and R3, R4, R7 R8 = H
was obtained.
The analytical values of this compound were:
Total amine value: 141 mg KOH/g Tertiary amine value: 141 mg KOH/g Hydroxyl value: 296 mg KOH/g - Example 3 237 g (1 mol) of an amine of the general formula (2), with a + c = 2.8 b = 0, was alkylated as described in Example 1 with 176 g (4 mols) of ethylene oxide. 413 g of a clear liquid of the general formula (4), with a + c = 2.8 b = 0 d + e + f + g = 4 and R3, R4, R7 R8 = H
was obtained.
This compound had the following analytical values:
Total amine value: 275 mg KOH/g Tertiary amine value: 268 mg KOH/g Hydroxyl value: 567 mg KOH/g 2510:1:Ms2510 Example 4 237 g (1 mol) of an amine of the general formula (2), with a + c = 2.8 b = 0 was alkylated as described in Example 1 with 352 g (8 mols) of ethylene oxide. 589 g of a clear liquid of the general formula (4), with a + c = 2.8 b = o d + e + f + g = 8 and R3, R4, R7 R3 = H
was obtained.
This compound had the following analytical values:
Total amine value: 197 mg KOH/g Tertiary amine value: 197 mg KOH/g Hydroxyl value: 439 mg KOH/g Example 5 615 g (1 mol) of the amine of the general formula (2), with a + c = 2.5 b = 9, was alkylated with 176 g (4 mols) of ethylene oxide, as described in Example 1. 791 g of a clear liquid of the general formula (4), with a + c = 2.5 b = 9 d + e + f + g = 4 and R3, R4, R7, R8 = H, was obtained.
This compound had the following analytical values:

2510:C~IS2510 Total amine value: 144 mg KOH/g Tertiary amine value: 142 mg KOH/g . Hydroxyl value: 291 mg KOH/g Exam~le 6 550 g (1 mol) of an amine of the general formula (3), with a = 7.7 b = 1 R6 = CH3, was alkylated with 132 g (3 mols) of ethylene oxide, as described in Example 1. 682 g of a clear liquid of the general formula (5), with a = 77 b = 1 R6 = CH3 d + e = 3 and R3 R4 = H
was obtained.
This compound had the followig analytical values:
Total amine value: 84 mg KOH/g Tertiary amine value: 84 mg KOH/g Hydroxyl value: 180 mg KOH/g Exam~le 7 912 g (2 mols) of an amine of the general formula ~2), with a + c = 6.6 b = 0, was alkoxylated with 464 g (8 mols) of propylene oxide.
1,376 g of a clear liquid of the general formula (4), with 2510:CMS2510 a + c = 6.6 b = 0 d + e + f + g = 4 R3, R4, R7, Rs = CH3 Thecompound had the following analytical values:
Total amine value: 163 mg KOH/g Tertiary amine value: 162 mg KOH/g Hydroxyl value: 323 mg KOH/g (II) Pre~aration of ester amines of the qeneral formulas (6) and (7) Exam~le 8 625 g (1 mol) of the amine ethoxylate from Example 1 was mixed with 570 g (2 mols) of tallow methyl ester (C17H3SCOOCH3), 1.5 g of solid, powdered NaOH and 3 g of sodium hypophosphite and, under a nitrogen atmosphere, stirred and heated to 180 C. The methanol forming during the reaction was distilled off. After approximately 90% of the theoretical amount of methanol had been removed, a vacuum of about 20 mbars was applied and the transesterification completed. After approximately 7 hours, 1,135 g of a yellow liquid of the general formula (6) with a + c = 6.6 b = 0 d + e + f + g = 4 R3, R4, R7 R3 = H
R1, R2, R9, R10 = 2 X H, 2 X -C-C17H35 O
This compound had the following analytical values:
Total amine value: 98 mg KOH/g Tertiary amine value: 97 mg KOH/g 2510:CMs2510 204~23~

Hydroxyl value: 93 mg KOH/g Saponification value: 106 mg KOH/g Exam~le 9 625 g (1 mol) of the amine ethoxylate from Example 1 was transesterified with 855 g t3 mols) of tallow methyl ester, 2 g of NaOH and 4 g of sodium hypophosphite, as described in Example 8. 1,390 g of a yellow liquid of the general formula (6) with a + c = 6.6 b = o d + e + f + g = 4 R3, R4, R7 R3 = H
Rl, R2, R9, R10 = 1 X H, 3 X -C-Cl7H35 o was obtained.
This compound had the following analytical values:
Total amine value: 78 mg KOH/g Tertiary amine value: 74 mg XOH/g Hydroxyl value: 57 mg KOH/g Saponification value: 117 mg KOH/g Exam~le 10 799 g (1 mol) of the amine ethoxylate from Example 2 was transesterified with 570 g (2 mols) of tallow methyl ester, 2 g of NaOH and 4 g of sodium hypophosphite, as described in Example 8. 1,311 g of a 0 . yellow liquid of the general formula (6) with a + c = 6.6 b = 0 d + e + f + g = 8 2510:CHs2510 20~4234 R3, R4, R7 R8 = H
Rl, R2, R9, Rl0 = 2 X H, 2 X -C-Cl7H35 was obtained.
This compound had the following analytical values:
Total amine value: 89 mg KOH/g Tertiary amine value: 88 mg KOH/g Hydroxyl value: 88 mg KOH/g Saponification value: 82 mg KOH/g Example 11 775 g (1 mol) of the amine ethoxylate from Example 5 was transesterified with S70 g (2 mols) of tallow methyl ester, 1.5 g of NaOH and 3 g of scdium hypophosphite, as described in Example 8. 1,285 g of a yellow liquid of the general formula (6) with a + c = 2.5 b = 9 d + e + f + g = 4 R3, R4, R7 Rs = H
R1, R2, R9, R10 = 2 X H, 2 X -C~C17H3s O
This compound had the following analytical values:
Total amine value: 86 mg KOH/g Tertiary amine value: 85 mg KOH/g Hydroxyl value: 86 mg KOH/g Saponification value: 91 mg KOH/g Example 12 407 g (1 mol) of the amine ethoxylate from Example 3 was transesterified with 570 g (2 mols) of 2510:CMS2510 20~423~

tallow methyl ester, 1.1 g of NaOH and 2.3 g of sodium hypophosphite, as described in Example 8. 916 g of a yellow liquid of the general formula (6) with 5a + c = 2.8 b = 0 d + e + f + g = 4 R3, R4, R7 R3 = H
R1, R2, R9, Rl0 = 2 X H, 2 X -C-C17H35 was obtained.
This compound had the following analytical values:
Total amine value: 121 mg XO~/g Tertiary amine value: 121 mg KOH/g Hydroxyl value: 118 mg ROH/g Saponification value: 127 mg KOH/g Example 13 625 g (1 mol) of the amine ethoxylate from Example 1 was mixed with 539 g (2 mols) tallow fatty acid and 1.2 g of hypcphosphoric acid under a nitrogen atmosphere with stirring and heated to 18Q C. The water forming during the reaction was distilled off. After an acid value of about 10 had been obtained, a vacuum of about 20 mbars was applied and the reaction was continued until the acid value was less than 2. 1,129 g of a clear liquid of the general formula (6) with a + c = 6.6 b = 0 d + e + f + g = 4 2510:CHS2510 R3, R4, R7 R3 = H
R1, R2, R9, R10 = 2 X H, 2 X -C~C17H3s was obtained.
This compound had the following analytical values:
Total amine value: 93 mg KOH/g Tertiary amine value: 93 mg KOH/g Hydroxyl value: 95 mg KOH/g Saponification value: 98 mg KOH/g Acid value: 1.3 mg KOH/g Example 14 1,669 g ((2.5 mols) of the amino alcohol from Example 6 was transesterified with 1,059 g (3.75 mols) of tallow methyl ester, 2.8 g of NaOH and 5.8 g of sodium hypophosphite, as described in Example 8. 2,626 g of a clear yellow liquid of the general formula (7) with a = 7.7 b = 1 R6 = CH3 d + e = 4 R3 R4 = H
R1, R2, = 0.5 X H, 1.5 X -C-C17H35 was obtained.
This compound had the following analytical values:
Total amine value: 55 mg KOH/g Tertiary amine value: 55 mg KOH/g Hydroxyl value: 41 mg KOH/g Saponification value: 76 mg KOH/g 2510:CHS2510 Example 15 625 g (l mol) of the amine ethoxylate from Example 1 was reacted with 1,140 g (4 mols) of tallow methyl ester, 2 g NaOH and 3 g of sodium hypophosphite, as described in Example 8. 1,642 g of a yellow liquid of the general formula (6) with a + c = 6.6 b = 0 d + e + f + g = 4 R3, R4, R7 R8 = H
R1, R2, R9, R10 = 4 X -C-Cl7H35 was obtained.
The reaction product had the following analytical values:
Total amine value: 68 mg XOH/g Tertiary amine value: 68 mg KOH/g Hydroxyl value: 1.5 mg KOH/g Saponification value: 139 mg KOH/g Exam~le 16 625 g (1 mol) of the amine ethoxylate from Example 1 was reacted with 285 g (1 mol) of tallow methyl ester, 1.5 g of NaOH and 3.0 g of sodium hypophosphite, as described in Example 8. 882 g of a yellow liquid of the general formula (6) with a + c = 2 - 6 b = 0 d + e + f + g = 4 R3, R4, R7, R8 = H
R1, R2, R9, R10 = 3 X H; 1 X -C-C17H35 O

2510:c~s2510 was obtained.
The reaction product had the following analytical values:
Total amine value: 128 mg KOH/g Tertiary amine value: 128 mg KOH/g Hydroxyl value: 64 mg KOH/g Saponification value: 191 mg KOH/g (II) PreParation of quaternarv ammonium compounds or of amine salts Exam~le 17 1,149 g (1 mol) of the ester from Example 8 was mixed at 60 C with 252 g (2 mols) of dimethyl sulfate in portions, with stirring, so that the temperature of the reaction mixture could be maintained at between 6C and 70 C. 1,397 g of a yellow liquid of the general formula (1) with a + c = 6.6 b = 0 d + e + f + g = 4 R3, R4, R7 R8 = H
Rl R2, R9, R10 = 2 X H, 2 X -!IC-Cl7H35 O
R13 = -CH3 o Il y~ = 2 x ~ -OS-OCH3 o was obtained.
This compound had the following analytical 3S values:
Cat SO3 acidic: 9.6 g SO3/100 g Total amine value: 2.3 mg KOH/g 2510:CM52510 Example 18 1,149 g (1 mol) of the ester from Example 8 was neutralized at 60O c with 200 g (2 mols) of a 90~ aqueous solution of lactic acid with stirring. 1,349 g of a clear yellow liquid of the general formula (1) with a + c = 6.6 b = o d + e + f + g = 4 R3, R4, R7 R3 = H
R1, R2, R9, R10 = 2 X H, 2 X -C-C17H35 Rl2, R = H
y~ = 2 X CH3 - CH - COO~
ll OH
was obtained.

This compound had the following analytical values:
Cat SO3 acidic: 10.0 g SO3/100 g pH (5% isopropane/water 1:1): 5.2 Exam~le 19 1,149 g (1 mol) of the ester from Example 8 was mixed at 60 C with 126 g (1 mol) of dimethyl sulfate in portions, with stirring, so that the temperature of the reaction mixture could be maintained at between 60 and 70 C. Then 100 g (1 mol) of a 90% aqueous solution of lactic acid was added for neutralization of the mixture.
1,373 g of a clear yellow liquid of the general formula (l) with a - c = 6.6 b = 0 d + e + f + g = 4 2510:~1s2510 204~23~

R3, R4, R7 R8 = H
R1, R2, R9, R10 = 2 X H, 2 X -C-C17H35 5R12, R13 = 1 x H , 1 x CH3 y~ = 1 x ~ -OS-OCH3, 1 x CH3-CH-COO-was obtained.
This compound had the following analytical value:
15Cat SO3 acidic: 10.1 g SO3/100 g Exam~le 20 1,305 g (1 mol) of the ester from Example 11 was quaternized with 252 g (2 mols) of dimethyl sulfate, 20as described in Example 17. 1,557 g of a clear yellow liquid of the general formula (1) with a + c = 2.5 b = 9 d + e + f + g = 4 25R3, R4, R7 R8 = H
Rl, R2, R9, R10 = 2 x H, 2 x -C-Cl7H35 R12 Rl3 = -CH3 o y~ = 2 x ~ -OS-OCH3 O

was obtained.
This compound had the following analytical values:

2510:CY52510 204423~

Cat SO3 acidic: 9.0 g S03tl00 g Total amine value: 2.2 mg KOH/g Exam~le 21 679 g (0.65 mol) of the ester from Example 14 was quaternized with 41 g (0.325 mol) of dimethyl sulfate, as described in Example 19, and the reaction mixture was then neutralized with 37 g of 90% lactic acid. 7S7 g of a clear yellow liquid of the general formula (1) with a + c = 7.7 b = 1 R6 = -CH3 d + e = 4 R3, R4 = H
R1, R2 = 0-5 x H, 1.5 x -C-C17H35 o R12 = 0-5 x CH3, 0.5 x -H

y = 0.5 x -OS-OCH3 , 0.5 x CH3-CH-COO-o OH

was obtained.
This compound had the following analytical value:
Cat SO3 acidic: 6.4 g SO3/100 g Example 22 1,149 g (1 mol~ of the ester from Example 8 was mixed at 60 C in portions, with vigorous stirring, with 196 g (2 mols) of a 36% aqueous HCl solution.

2510:CIIS2510 1,345 g of a pale-yellow liquid of the general formula (1) with a + c = 6.6 b = 0 d + e + f + g = 4 R3, R4, R7 R8 = H
R1, R2, R9, R10 = 2 x H, 2 x -C-C17H35 R12, R13 = H
y~ = 2 x Cl was obtained.
This compound had the following analytical ~alues:
Cat SO3 acidic: 10.3 g SO3/100 g pH (5% isopropanol/water 1:1): 4.2 2510:CMS2510

Claims

1. A compound of the general formula (1) where R5 is a group, or -OH, or -O-R6, R6 is an alkyl group having from 1 to 5 carbon atoms, or a group, and where R1, R2, R9 and R10 are, independently of one another, hydrogen, an alkyl group having from 1 to 5 carbon atoms, or a group, R11 is a hydrocarbon group having from 11 to 21 carbon atoms which is optionally branched and optionally contains multiple bonds or hydroxyl groups, with the proviso that at least one of the groups R1, R2, R9 and R10 must be the group ;

2510:CMS2510 R3, R4, R7 and R8 are, independently of one another, H or CH3, R12 and R13 are, independently of one another, H, CH3, -C2H5 or a benzyl group; and k and l are from 0 to 1, k + l is from 0 to 2, a + c is from 1 to 40, b is from 0 to 40, d + e + f + g is from 2 to 12, and y- is a mono- or polyvalent anion having a total of k + 1 negative charges.

2. A compound as defined in claim 1, wherein k + 1 is 0.

3. A compound as defined in claim 1, wherein R12 and R13 are, independently of one another, H or CH3, and k + 1 is from 0.5 to 2.

4. A compound as defined in claim 1, wherein R5 is the group 2510:CMS2510

5. A compound as defined in claim 1, wherein R5 is an -O-R6 group, and R6 is an alkyl group having from 1 to 5 carbon atoms.

6. A compound as defined in claim 1, wherein at least one of the groups R1, R2, R9 and R10 is the group , and R11 is an alkyl group or an alkylene group having from 7 to 17 carbon atoms.

7. A compound as defined in claim 1, wherein R12 and R13 are, independently of one another, CH3 or H, k + 1 is from 0.5 to 2, and d + e + f + g is from 4 to 8;
R3, R4, R7 and R8 are H; and from 1 to 3 of the groups R1, R2, R9 and R10 have the meaning .

8. A compound as defined in claim 1, wherein a + c is from 1 to 15 and b is from 0 to 15.

9. A process for producing a compound as defined in claim 1, comprising reacting, in a first step, compounds of the general formula (2) (3) or both where PO is and EO is -(O-CH2-CH2), a is from 0 to 20 and c is from 0 to 20, and a + c is from 1 to 40, b is from 0 to 40 and R6 is an alkyl group having from 1 to 5 carbon atoms or a group, R" is a hydrocarbon grop having from 11 to 21 carbon atoms which is optionally branched and optionally contains multiple bonds or hydroxyl groups, at from 120 to 160° C with a quantity of an alkylene oxide corresponding to the desired degree of alkoxylation in a pressurized reactor at from 1 to 4 bars, optionally using solvents, and optionally in the presence of catalysts, and forming compounds of the general formula (4) (5) 2510:CMS2510 or both where A is -(PO)a-(EO)b-(PO)C, which are then reacted with a quantity of fatty acid or fatty-acid derivative corresponding to the desired degree of esterification, at from 160 to 200° C, optionally in the presence of a catalyst, and continuously distilling off the water of reaction forming, or the alcohol, optionally at a pressure of less than 1 bar, and forming compounds of the general formula (6) (7) or both which are then optionally converted in portions by the use of a quaternizing agent, an acid, or both, optionally with the concurrent use of solvents, at from 20 to 80° C, in a quantity corresponding to the desired quaternization (salt) degree, to form compounds of the general formula (1), with k + 1 > 0.

2510:CMS2510

10. A component in the manufacture of an emulsifier, a detergent, a disinfectant or a preservative comprising a compound as defined in claim 1.

2510:CMS2510