NL193247C - Phosphorus-containing betaine derivatives. - Google Patents

Description

1 193247

Phosphorus-containing betaine derivatives

The invention relates to phosphorus-containing beta-derivatives.

Such betaine derivatives are known from British Pat. No. 1,388,879. More particularly, this British patent relates to phosphorus compounds of the formula H- (0 ©) P (0) -0-CH (R1) -C (R2) (R3) -CH2-N®R4R5R6 wherein R1, R2 and R3 is a hydrogen atom or an alkyl group with preferably 1-4 carbon atoms, R4 is a hydrogen atom, an alkyl group with 1-12 carbon atoms, an alkenyl group with 2-12 carbon atoms, or a group of the formula - (C 1 H 2 nO) 2 H, R 5 a hydrogen atom, an aliphatic hydrocarbon group of 10 1-20 carbon atoms or a group of the formula - (Cn h 2 ") zh and R6 an aliphatic hydrocarbon group of 1-20 carbon atoms, an aralkyl or cycloalkyl group, a group of the formula - (C "H2n) 2H or a group of the formula R7C0NHCnH2n-, wherein R7 represents an alkyl group of 1-20 carbon atoms or an alkenyl group of 2-20 carbon atoms, n is 2 or 3, and when R4 and / or R5 and / or R6 represent a group of the formula - (CnH2n) zH, the sum of the values z is 1-50 or R5 or R6 form a ring together with the nitrogen atom and R4 has the above meaning.

The betaine compounds according to the above-mentioned British Patent Specification 1,388,879 are valuable intermediates in the preparation of, inter alia, pesticides and textile auxiliaries (see page 2 lines 59-66). Compounds according to this British patent, especially when at least one of the symbols R4, R5 or R6 represents an alkyl or alkenyl group with at least 8 carbon atoms (see page 2, lines 73-78), have surfactant properties and are useful, for example, as emulsifiers for oil in water emulsions, but also have a strong extraction affinity for zinc in the well-known liquid-liquid extraction processes.

U.S. Patent 3,950,417 relates to betaine compounds of the formula R5 - {- CO-N (R4) - (CH2) m-} nN (R2) (R3) -Y-R1 wherein R, the group COO 'or -CH (OH) -CH 2 SO 3 -, R 2 a lower alkyl group, R 3 a lower alkyl group, R 4 a hydrogen atom or a lower alkyl group, R 5 a large alkyl group Y a lower alkylene group, preferably methylene, m an integer from 2 to 7 and n represent an integer of 0 or 1.

These amidosulfobetain compounds known from this US patent have good foaming capacity, good foaming stability and low eye irritation.

French Patent 2,224,445 relates to ethoxylated quaternary ammonium mono- and diphosphates and sulfates, which however do not contain a second nitrogen amide group, are antistatic and have good surfactant properties, are stable and have low skin and eye irritation.

The object of the invention is to develop new phosphorus-containing betaine derivatives, which have a remarkable combination of properties of foaming, viscosity provision, wetting, cleaning, as well as detergent, antistatic and emulsifying properties and are therefore useful for industrial applications, for which surfactants of very good quality are required. The connections are also extremely stable.

New phosphobetain compounds for industrial use have been found, which are represented by the formula 1 and the formula 4 of the formula sheet, in which AO represents ©, OM or -OYR®, represents BO © or OM ', X © represents an anion, z O or the number 1 or 2 denotes 50, with the proviso that only either A or BO © may represent and z has a value necessary to provide charge equilibrium, Y an alkylene group, which may be interrupted by at most 3 oxygen atoms , which has at most 12 carbon atoms, which alkylene chain may be substituted by one or more alkyl, alkoxy, hydroxyl or hydroxyalkyl groups, with the proviso that in formula 4 the alkylene group Y is substituted by one or 55 more alkoxy, hydroxyl or hydroxyalkyl groups are substituted, M and M ', which are the same or different, each (a) a hydrogen atom, (b) an organic radical from the group of alkyl or hydroxyalkyl with up to 6 carbon atoms, polyh ydroxyaikyl with up to 16 carbon atoms 193247 2 atoms, glyceryl, cycloalkyl with up to 6 carbon atoms or aryl or arylalkyl with up to 10 carbon atoms or (c) represent a salt residue of the alkali metals, alkaline earth metals or mono-, di-triethanolamine it being understood that if either M or M 'represents an organic residue (b), the other residue M or M' must be a hydrogen atom (a) or a salt residue (c), and 5 R is a residue derived from an amidoamine reactant with formula 2 represents, in which formula 2 R 1 represents an alkyl, alkenyl, alkoxy or hydroxyalkyl group each having 5-22 carbon atoms or an aryl or alkaryl group having up to 20 carbon atoms, R2 means a hydrogen atom, an alkyl, hydroxyalkyl or alkenyl group each having up to 6 carbon atoms, a cycloalkyl group having up to 6 carbon atoms or a polyoxyalkylene group having up to 10 carbon atoms, R 3 and R 4, which may or may not be the same, each an alkyl hydro xyalkyl or carboxyalkyl group with up to 6 carbon atoms in each of the alkyl radicals or a polyoxyalkylene group with up to 10 carbon atoms indicate whether R3 and R4 together with the nitrogen atom to which they are attached indicate a nitrogen-containing heterocyclic radical, wherein the residues Y and Y 'respectively is bonded to a ring atom of the nitrogen-containing heterocyclic moiety other than the nitrogen atom of the R moiety, and n denotes an integer 2-12, or R is a nitrogen-containing heterocyclic compound of formula 3, wherein ZN, S is O, o is an integer from 0 to 3, 20 p is an integer from 1 to 3, with the proviso that the sum of o + p is 3 to 4, and R 1 is an alkyl- , an alkenyl, an alkoxy, or a hydroxyalkyl of 5 to 22 carbon atoms or an aryl or aikaryl group of up to 20 carbon atoms and is attached to a carbon atom of the ring, and R6 is an alkyl group of 2 to 6 carbon atoms a e can be substituted or non-terminal carbon atom by a hydroxyl group.

The term "" polyoxyalkylene group "" as used in the above definition of R2, R3 and R4 may denote a radical of the formula (Rs-O-R5) m wherein R5 and R5 "are alkyl groups of 1-4 carbon atoms and m an integer such that the group contains at most 10 carbon atoms.

Particularly preferred subgroups of the compounds of general formula 1 can be represented by formulas 5, 6 and 7.

The compounds of the general formula 7 are bis-phosphobetaines, which contain two amine residues. In the compounds of formulas 6 and 7, the presence of an anion (X®) is required for the charge equilibrium. This Xe moiety can be an added anion, such as a hydroxyl group or a halide, sulfate, phosphate or negatively charged (anion) moiety, which is provided by a solvent or a reaction component, as used in the synthesis of compounds of formulas 6 and 7. For example, X® may be the halide residue ("Hal"), which is released in the reactions further described below.

The phosphobetane compounds of formula 1 of the invention may be prepared from the corresponding phosphate esters and amine reaction components as indicated in the reaction scheme of Figure 1, wherein R represents an amine reaction component of formula 8 or nitrogen heterocyclic compound of formula 3, the symbols used have the above meaning.

More specifically, the relative groups of phosphobetane compounds of the invention as corresponding to formulas 5, 6 and 7 can be synthesized by a number of methods, as indicated in more detail below with reference to the respective reaction schemes.

45

Method A (amine + phosphate ester halide) - as indicated in the reaction scheme of Figure 2, wherein Hal represents a halogen atom or one of the other radicals as defined above; or indicated by the reaction scheme of Figure 3, wherein the moieties have the above meanings 50; or according to the reaction scheme of figure 4, wherein the residues have the above meaning. According to another method (B) for preparing certain phosphobetane compounds according to the invention, use is made of a conversion between the amine reaction component (R) and a certain cyclic hydroxypropylene group-containing phosphate ester component of the formula 13 and 55, respectively, as indicated in the reaction scheme of figure 5 and 6, respectively, in which the reactants have the above-mentioned meaning, it being understood that the anion X® can be provided by the halide (Hal) group, which is split off from the reactant (in the case X® = Hal) or 3 193247 may be from another source as explained. The designations "HO (C3H5)" or "(C3H5OH)", as indicated, refer to a hydroxypropylene function, where the cyclic oxa residue is bonded to one of the three carbon atoms and the cyclic oxa residue is further bonded to only one of the three carbon atoms, preferably in the 3- or 2-position of the propyl group.

The phosphitine compounds of the invention can be prepared from the corresponding phosphite esters and amine reaction components, as indicated in the reaction scheme of Figure 7, wherein R denotes an amine reaction component of Formula 8 or Formula 3, wherein the symbols have the above-mentioned meaning.

The reactants required for the reaction can be prepared in the following manner: 10

Preparation of "R" reaction components used as intermediate.

The amine reaction component "R" suitable for all syntheses is generally prepared by reacting an aminoalkyl-substituted tertiary amine with an acid to obtain the amidoamine function. Also, an aminoalkyl-substituted secondary amine can be reacted with an acid, followed by further treatment of the reaction product with an epoxyalkane. Finally, if the radical R has a nitrogen-containing heterocyclic structure, for example the imidazolyl structure, this intermediate can be prepared according to known techniques, such as for example described in U.S. Pat. No. 2,267,965.

When the reaction according to the reaction scheme of figure 8 is used, the non-cyclic reaction components "R" are obtained, while on the basis of the reaction according to the reaction equation of figure 9, the preparation of a typical cyclic amine reaction component "R" (an imidazolyl- reaction component), wherein R 1 has the above meaning and R 7 represents an alkyl group of 2-6 carbon atoms, which may be substituted by a hydroxyl group (at the terminal or non-terminal carbon atom). This cyclic reactant can be prepared as described in U.S. Patent 2,267,965.

Preparation of intermediate phosphate ester reactants.

The intermediate phosphate ester reactants obtained according to the reaction equations of Figure 1, Figure 2 and Figure 3 can also be prepared by conversions, as illustrated by the reaction equations of Figure 10, Figure 11 and Figure 12 .

For certain reactants of formula 9, i.e. the reactants wherein M represents a hydrogen atom or an alkali or alkaline earth metal cation, the synthesis of the intermediate can be performed according to the reaction scheme of Figure 13 or Figure 14, wherein M "is an alkali metal or alkaline earth metal cation (for example, a sodium, potassium, magnesium or calcium cation).

The conversions according to the reaction equation of Figure 13 and Figure 14, respectively, are carried out in two stages. The first stage takes place under anhydrous conditions to obtain a chlorine phosphate. This material is then diluted to 40% with water and one molar equivalent of M "OH, for example sodium hydroxide.

The phosphate ester reaction components required as intermediates for the above-mentioned Method B can be prepared according to the reaction schemes of Figures 15 and 16, respectively.

It should be noted that the reactions according to the reaction schemes of Figures 15 and 16 use similar reactants as those used in the conversions described above according to the reaction schemes of Figures 11 and 12 (although limited to the hydroxypropyl definition), but that different cyclic products be obtained. The different products are the result of a different pH adjustment, i.e., while the conversion according to the reaction scheme of Figure 11 is carried out at a pH of 4-5, the conversion according to the reaction scheme of Figure 15 is carried out at a pH of 9.5-10.5, whereby a cyclic product is obtained. This cyclic product may also contain some vicinal epoxy material, so the formula 13 is to be understood to include not only one or more of the isomers resulting from a bond of the oxa oxygen atom to one of the hydroxypropylene carbon atoms (to form a 5- or 6-ring), but also substances of the formula 16. By working at a higher pH, for example a pH of 10.5 or more, the formation of the vicinal epoxy-containing material would be favored.

55 Preparation of phosphite ester reactants used as intermediate.

The preparation of the intermediate phosphite ester reaction component is carried out according to the reaction scheme of Figure 17.

193247 4

When carrying out the conversions according to the reaction schemes of Fig. 1 to Fig. 4, which ultimately lead to the phosphobetain compound according to the invention and the reaction according to the reaction scheme of Fig. 17, which finally leads to the phosphitone compound according to the invention, the intermediate amine reactant (R) reacted with the phosphate ester reactants or phosphite ester reactant required as intermediate 5, which conversions are generally carried out in an aqueous system at a temperature of 80-100 ° C. The phosphobetaine or phosphitain product will finally have a pH of 6-8 at a concentration of 10%, depending on the specific nature of the product, i.e. the nature of the amine reaction component used.

These new phosphobetaines and phosphitains are good surfactants and unexpectedly exhibit good foam volume and excellent foam stability compared to the commercially available amphoteric and zwitterionic surfactants (cocoamido-propylbetalne / sultain) ).

One method of demonstrating these properties is based on an adaptation of the well-known Ross-Miles foam test principle ("Oil and Soap" 18, 99-102 (1941)) in the following manner:

Cosmetic grade anhydrous lanolin is mixed with dioxane (technical grade) in a ratio of 2.5 g lanolin per 100 g dioxane. The lanolin is first mixed with 25 cm 3 of dioxane. This mixture is heated on a steam bath to a temperature of 45 ° C to dissolve the lanolin in the dioxane. The rest of the dioxane is then added and mixed. This lanolin-dioxane solution, which is stored in an amber-colored bottle, must be prepared fresh on the day of the tests.

The preparation to be tested is diluted by adding 376 cm 3 of distilled water to 4 g of the preparation, followed by addition of 20 cm 3 of the above-described lanolin-dioxane solution while mixing. When the lanolin-dioxane solution is added to the aqueous solution of the preparation, heat is released and care must be taken to set the temperature of this solution to 24-25 ° C. These starting solutions should therefore both be adjusted to a temperature of 23 ° C before mixing. The lanolin-diozan solution should be cooled gradually to avoid precipitation of the lanolin. In this way a finished solution with a temperature of 24-25 ° C will be obtained.

The finished solution of the composition to be tested, water, dioxane and lanolin, as described above, is then introduced into a modified Ross-Miles foam column in the usual manner. All tests are performed in duplicate, taking the average of the two results. The foam stability is determined by measuring the foam height decay after 2 minutes, expressed as a percentage of the initial height.

Typical examples of foam values obtained using the above procedure for an alkylamidophosphobetaine, an alkylamidobetaine and an alkylamidosultaine are set forth below.

Example No. Foam Volume, Decay,%, After 40 ml 2 Minutes Sodium Salt of Laurin Myristin VII 250 4.0 Amidopropyl-2-Hydroxypropyl Phosphobetaine (Formula 37) 45 Disodium Salt of Cocamidopropyl-2 VI 240 10 Hydroxypropyl Phosphobetaine (Formula 37) Disodium Salt of cocamido- XXV 210 19 propylphosphobetaTne (formula 60) cocamido-propyl betaine (comparison) - 225 31.0 50 cocamido-propyl sultaine (comparison) - 200 60.0

As can be seen from the above results, the phosphobetaines of the invention exhibit excellent foam volume and foam stability, while the stability of the betain and sultain 55 is considerably less.

In another series of tests, further examples of the phosphobetaine and phosphitain compounds of the invention were investigated in a "cylinder shake test" to evaluate the 5 193247 foam properties.

Test solutions containing 0.1 wt% of the surfactant to be tested in water having a hardness of 100 ppm (molar ratio of calcium to magnesium of 3: 2) were used in this test and in stoppered cylinders with a capacity of 100 ml, which had been cleaned in such a way that the water ran down the walls thereof as a unitary film.

Each cylinder filled with a test solution was shaken in a standardized manner 20 times, after which the net foam volumes were observed first one minute and then again 5 minutes after shaking. The tests were performed in triplicate. The results were as follows: Laurine / myristine type Example No. 1 minute 5 minutes lauric myrstine amidobetaine (comparison - 67 60 king) sodium lauryl sulfate (comparison) - 85 74 15 monosodium salt of lauric myristin II 88 78 amidopropyl -2-hydroxypropylphosphobetaine (formula 35) disodium salt of laurin myristin VII 85 78 amidopropyl 2-hydroxypropyl phosphobetaine 20 (formula 37) laurin myristin amidopropyl 2 XII 86 78 (hydroxypropyl) glyceryl phosphobetaine (formula 42) disodium salt of laurin-myristin-XXXIII 87 73 25 amidopropyl-carboxymethyl-2-hydroxyethyl-phosphobetaine (formula 65) N-cocamidoethyl-N-hydroxyethyl-glycine - 76 67 (comparison) laurine-myristine-amido-2-XLIV 88 76 30 hydroxypropyl phosphitain (formula 78)

Coco type Example No. 1 minute 5 minutes 35 cocobetaine (comparison) - 65 56 coamidobetaine (comparison) - 70 63 monosodium salt of cocamido-2 I 79 74 hydroxypropyl phosphobetaine (formula 35) cocamidoglyceryl-2 XI 71 74 40 hydroxypropyl phosphobetaine (formula 41) monosodium salt for coco-XIX 83 78 imidazolinyl phosphobetaine (formula 48) disodium salt of coco XXVI 80 75 imidazolinyl phosphobetaine (formula 62) 45 bis (coco-imidazoyl) phosphobetaine XXXIV 75 69 (formula 66) cocamido-2-hydroxypropyl phosphitaine formula 78) 50

In addition, the compounds of the invention have the potential to cause surprisingly low ocular irritation compared to commercially available amphoteric and zwitterionic surfactants. The test used is the modified Draize test (J.H. Draize et al., Toilet Goods Assn. No. 17, May, 1952, No. 1 Proc. Sci. Sect .; Chem. Abstr. 46, 8774 g (1952).

According to this method, a 0.1 ml sample of a neutral solution of the test compound is added to one eye of an albino rabbit while the other eye acts as a control. Six rabbits are used for each compound.

193247 6

Observations were made after 1.24, 48, 72 and 96 hours and 7 days after the initial installation, while second and third installations were made after the observation at 24 and 48 hours. Results can range from virtually no change or only minor irritation in the rabbit's eye appearance after 7 days to severe irritation and / or complete corneal opacity. Eye lesions are graded on a numerical scale for the cornea, iris, and conjunctiva, with a higher number indicating stronger eye irritation, which are added to a total numerical value for each determination for six rabbits, including the mean. The mean value is an indication of the potential irritation of the preparation to be tested. Based on the average number value, a descriptive irritation rating can be given, eg none, minor, moderate, severe, etc.

Typical examples of results for a betaine, sultaine and a phosphobetaine according to the invention, when subjected to the above test protocol, are as follows:

Potential eye irritation 15 -

Compound 1 hour 24 48 72 96 7 Irritation hours hours hours hours days value dinatisum salt of 7.7 0.3 1.3 1.0 0.0 0.0 low 20 laurine-myristine-amidopropyl-2-hydroxypropylphospho-betaine ( formula 37) cocamidopropyl- 11.7 4.2 9.3 13.2 11.2 5.8 severe betaine (comparison) cocamidopropylsul- 15.0 8.5 15.6 25.0 - - severe taine (comparison) bis (coco 10.5 4.7 5.0 3.3 3.7 0.7 minor imidazoline) phospho-30 betaine (formula 66) cocamidoglycerylphos-9.2 5.0 4.3 9.0 5.7 0.7 low phobetaine (formula 41) 35

All tests were performed at a concentration of 3% (w / w).

In support of the above test results, a further series of tests was conducted in the manner described above, using only one guinea pig per compound, yielding the following results: 40 -----------

Example Day Irritation No. 1 2 3 4 7 45 - disodium salt of VII 7 0 1 1 0 very lauric low myristine adidopropyl-2-hydrorypropyl-50 phosphobetaine (formula 37) glyceryl "CA-35" XV 4 0 0 0 0 very low 7 193 247

Example Day Irritation No. 5 __ 1 2 3 4 7 disodium salt of XXXIII 2 2 0 0 0 very lauric low myristin carboxyphosphobetaine (formula 65)

Comparison "Amphoteric 20" * - 21 15 7 5 0 moderate (comparison) cocobetaine - 23 26 19 17 25 severe (comparison) cocamidobetaine - 21 19 14 9 6 severe 20 (comparison) sodium lauryl sulfate - 18 16 16 16 10 severe (comparison) "CA-35" ** - 26 21 21 16 0 severe * N-cocamidoethyl-N-hydroxyethylglycine.

25 ** 2-undecyl-1-hydroxyethyl-propionic imidazoline.

As is readily apparent, the phosphobetams of the invention exhibit only minor ocular irritation, while the betain and sultain are severely irritating.

The preparation of specific compounds of the invention is illustrated by the specific examples below. For simplicity, the specific intermediate phosphate ester reactants (prepared according to the above reaction schemes of Figures 10 to 16) and the specific intermediate phosphate ester reactant (prepared according to the reaction scheme of Figure 17) which were used in these examples are first described. used in combination with certain tertiary amine (= 3 ° N) reactants specifically mentioned in each of the examples.

Phosphate ester reactants used as intermediate.

Reaction component "A" - of formula 17, prepared according to the reaction scheme of figure 10 (example 1) Reaction component "B" - of formula 18, prepared according to example 2 40 Reaction component "C" - of formula 19 and / or 20, prepared according to example 3

Reaction component "D" - of formula 21 (80) prepared according to the reaction scheme of figure 12 (example 4)

Reaction component "E" - with formula 22 and / or 23, prepared according to the reaction schemes of figure 14 and figure 15 (example 5) 45 Reaction component "F" - with formulas 24 and 25 (example 6)

Reaction component "G" - with formulas 26 and 27 (example 7)

Reaction component "H" - with formulas 28, 29.30 and 31 (example 8)

Reaction component "T" - with formulas 32 and 33 (example 9). 50 Intermediate phosphite ester reaction component.

Reaction component "J" - with formula 34 (example 10)

Example /

20.5 parts of Reaction component "A" and 60.0 parts of water were placed in a reaction vessel and stirred well. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 19.5 parts of 55 molten 3-cocoamidopropyl-dimethylamine were slowly added. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 3-4 hours. Over this period, 97% conversion was terminated, as determined by inorganic chloride and tertiary 193247 amine analysis.

The product consisted of an aqueous solution of a new compound of formula 35, wherein R 1 represents an alkyl group of 7-17 carbon atoms.

Example II

20.8 parts of Reaction component "A" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. 19.2 parts of a 70/30 mixture of lauramidopropyl-dimethylamine and myristamidopropyl-dimethylamine were slowly added to the solution thus obtained with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 3-4 hours. At the end of this period, a conversion degree of 97% was reached, as determined by the analysis of inorganic chloride and tertiary amine.

The product was an aqueous solution of a new product of formula 35, wherein R 1 represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

15

Example III

23.9 parts of Reaction component "A" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. To the solution thus obtained, 16.1 parts of caprylamidopropyl-dimethylamine were slowly added with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 3-4 hours. Over this period, a conversion rate of 97% was reached, as determined by the analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 35, wherein R 1 represents an alkyl group with 7 carbon atoms.

25

Example IV

18.5 parts of Reaction component "A" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of about 50 ° C. 21.5 parts of 3-oleamidopropyl-dimethylamine were slowly added to the solution thus obtained, with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 3-4 hours. After this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 35, wherein R 1 represents an alkyl group with 17 carbon atoms.

35

Example V

23.6 parts of Reaction component "A" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of about 50 ° C. 16.4 parts of a 70/30 mixture of 3-lauramidopropyl-diethylamine 40 and 3-myristamidopropyl-diethylamine were slowly added to the solution thus obtained with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 3-4 hours. After this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of the formula 36, wherein R1 45 represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

Example VI

22.4 parts of Reagent "C" and 60.0 parts of water were introduced into a reaction vessel with good stirring.

50 Heat was supplied to a temperature of about 50 ° C. 17.6 parts of 3-cocamidopropyl-dimethylamine were slowly added to the solution thus obtained, with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 3-4 hours. Over this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

55 The product consisted of an aqueous solution of a new product of the formula 37, wherein R 1 represents an alkyl group of 7-17 carbon atoms.

9 193247

Example VII

25.7 parts of Reagent component "C" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. 14.3 parts of a 70/30 mixture of lauramidopropyl-dimethylamine and 5-myristamidopropyl-dimethylamine were slowly added to the solution thus obtained, with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 3-4 hours. Over this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 37 wherein R 1 represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

Example VIII

20.8 parts of Reaction component "C" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of about 50 ° C. To the solution obtained in this way, 19.2 parts of a 70/30 mixture of 3-lauramidopropyl-diethylamine and 3-myristamidopropyl-diethylamine were slowly added with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 3-4 hours. After this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of the formula 38, wherein R1 represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

Example IX

26.8 parts of Reaction component "B" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. To the solution thus obtained, 13.2 parts of 3-caproamidopropyl-dimethylamine were slowly added with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 3-4 hours. Over this period, a conversion rate of 98% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 39, wherein R represents an alkyl group with 5 carbon atoms.

Example X.

26.2 parts of Reaction component "B" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. 13.8 parts of a 70/30 mixture of 3-lauramidopropyl-diethylamine and 3-myristamidopropyl-diethylamine were slowly added to the solution thus obtained with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 3-4 hours. In the course of this period, a conversion rate of 98% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 40, wherein R represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

45 Example XI

20.4 parts of Reaction component "D" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. To the solution thus obtained, 19.6 parts of molten 3-cocamidopropyl-dimethylamine was slowly added with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 3-4 hours. Over this period, a conversion rate of 98% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of the formula 41, wherein R represents an alkyl group of 7-17 carbon atoms.

55 Example XII

26.4 parts of Reaction component "D" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was applied at a temperature of 50 ° C. To the solution thus obtained, 193247 were slowly added 13.6 parts of a 70/30 mixture of 3-lauramidopropyl-diethylamine and 3-myristamidopropyl-diethylamine with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 3-4 hours. Over this period, a conversion rate of 98% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 42, in which R represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

Example XIII

14.4 parts of Reaction component "E" and 60.0 parts of water were placed in a reaction vessel with good stirring. Heat was added to a temperature of 50 ° C. Then, with good stirring, 25.6 parts of molten 3-cocamidopropyl were added. dimethylamine added Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 3-4 hours During this period, a conversion rate of 98% was reached, such as by analysis of anorga 15-chloride and tertiary amine were determined.

The product consisted of an aqueous solution of a new product of the formula 43, wherein R represents an alkyl group of 7-17 carbon atoms.

Example XIV

15.3 parts of Reaction component "E" and 60.0 parts of water were placed in a reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. To the solution thus obtained, 24.7 parts of a 70/30 mixture of 3-lauramidopropyl-dimethylamine and 3-myristamidopropyl-dimethylamine were slowly added with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 3-4 hours. In the course of this period, a conversion rate of 98% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 43, wherein R represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

Example XV

20.7 parts of Reaction component "B" and 60.0 parts of soft water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 19.30 parts of 2-undecyl-1- (ethyloxyethylcarboxylic acid) imidazoline were added while heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours . The conversion was complete when the inorganic chloride content reached 97% of theory.

The product consisted of an aqueous solution of a new product of the formula 44, wherein R represents an alkyl group with 11 carbon atoms.

40 Example XVI

27.9 parts of Reaction component "E" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was added to a temperature of 50 [deg.] C. In the solution thus obtained, 12.1 parts were slowly added with good stirring. 3-Caproamidopropyl-diethylamine was added, heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 3-4 hours, during which time a conversion rate of 98% as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 45, wherein R represents an alkyl group with 5 carbon atoms.

50 Example XVII

21.7 parts of Reaction component "C" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. To the solution thus obtained, 18.3 parts of a 70/30 mixture of lauramidoethyl-2,6-dimethylmorpholine and myristamidoethyl-2,6-dimethylmorpholine were slowly added with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 3-4 hours. Over this period, the conversion rate reached 98%, as determined by analysis of inorganic chloride and tertiary amine.

11 193247

The product consisted of an aqueous solution of a new product of the formula 46, wherein R represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

Example XVIII

26.7 parts of Reaction component "C" and 60.0 parts of water were introduced into a reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. To the solution thus obtained, 13.3 parts of 3-benzamidopropyl-dimethylamine were slowly added with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 3-4 hours. Over this period, a conversion rate of 98% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 47, wherein R 1 represents a phenyl group.

Example XIX

22.88 parts of Reagent "A" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was added to a temperature of 50 ° C. With good stirring, 17.12 parts of 1-hydroxyethyl-2- alkyl-2-imidazoline with 7-17 carbon atoms added in the alkyl group Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 4 hours. of 97%, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 48, wherein R represents an alkyl group of 7-17 carbon atoms.

Example XX

19.72 parts of Reagent "F" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then 20.28 parts of 3-cocamidopropyl-dimethylamine were added with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was completed when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of the formula 49 and 50, in which R represents an alkyl group of 7-17 carbon atoms.

Example XXI

20.69 parts of Reaction component "F" and 60.0 parts of water were introduced into a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 19.31 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline of 7-17 carbon atoms were added in the alkyl group. The heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached 40 theoretical and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of formula 51 and 52, wherein R represents an alkyl group of 7-17 carbon atoms.

Example XXII

45 20.72 parts of Reaction component "G" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then 19.28 parts of 3-cocamidopropyl-dimethylamine were added with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of formulas 53 and 54, in which R represents an alkyl group of 7-17 carbon atoms.

Example XXIII

55 21.70 parts of Reaction component "<3" and € 0.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 18.30 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline of 7-17 carbon atoms were added in the alkyl group. Heating 193247 12 was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of formulas 55 and 56, wherein 5 R represents an alkyl group of 7-17 carbon atoms.

Example XXIV

20.30 parts of Reagent "H" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Subsequently, 19.70 parts of 3-cocamidopropyl-dimethylamine were added with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of formulas 39, 57, 58 and 59, where R represents an alkyl group of 7-17 carbon atoms.

Example XXV

20.90 parts of Reagent Ί ”and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 19.10 parts of 3-cocamidopropyl-dimethylamine were added. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of formulas 60 and 61, in which 25 R represents an alkyl group of 7-17 carbon atoms.

Example XXVI

20.2 parts of Reagent "C" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 19.8 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline with 17 carbon atoms were added in the alkyl group. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. Over this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of the formula 62 wherein R represents an alkyl group with 17 carbon atoms.

Example XXVII

22.4 parts of Reagent "C" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 40 17.6 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline of 11 carbon atoms were added in the alkyl group. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. Over this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of the formula 63, wherein R 45 represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

Example XXVIII

26.9 parts of Reagent "C" and 60.0 parts of water were introduced into a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 50 13.1 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline with 7 carbon atoms were added in the alkyl group. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. Over this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of the formula 63, wherein R represents a 55 alkyl group with 7 carbon atoms.

13 193247

Example XXIX

21.4 parts of Reaction component "B" and 60.0 parts of water were introduced into a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, under good stirring, 18.6 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline having 17 carbon atoms in the alkyl group were added. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. Over this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 64, wherein R represents an alkyl group with 17 carbon atoms.

10

Example XXX

23.6 parts of Reaction component "B" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 16.4 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline (of which the alkyl group contained 70% 11 carbon atoms and 30% 13 carbon atoms) were added. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. Over this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of the formula 64, in which R represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

Example XXXI

25.4 parts of Reaction component "B" and 60.0 parts of water were introduced into a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. 14.6 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline having 11 carbon atoms in the alkyl group were then added with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. Over this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 64, wherein R represents a alkyl group with 11 carbon atoms.

Example XXXII

29.4 parts of Reaction component "B" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then 10.6 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline of 5 carbon atoms in the alkyl group were added with good stirring. Heating was continued for 4 hours. After this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of formula 64, wherein R represents an alkyl group with 5 carbon atoms.

40

Example XXXIII

18.04 parts of Reagent "C" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was added to a temperature of 50 ° C. Then, with good stirring, 21.96 parts of N-alkylamidoethyl-N- Hydroxyethyl glycine (the alkyl group of which contained 70% 11 carbon atoms and 45 contained 30% 13 carbon atoms) Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of formula 65, in which R 50 represents 70% lauryl groups and 30% myristyl groups.

Example XXXIV

22.0 parts of Reaction component "D" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 55 18.0 parts of 1-hydroxyethyl-2-alkyl-2-imidazoiine with 17 carbon atoms were added in the alkyl group. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. At the end of this period, a conversion rate of 97% 193247 14 was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of the formula 66, wherein R represents an alkyl group with 17 carbon atoms.

5 Example XXXV

22.2 parts of Reaction component "D" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 15.8 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline (the alkyl group of which contained 70% 11 carbon atoms and 30% 13 carbon atoms) were added. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. After this period, a conversion rate of 97% was reached, as determined by analysis of inorganic chloride and tertiary amine.

The product consisted of an aqueous solution of a new product of the formula 66, wherein R represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

15

Example XXXVI

22.61 parts of Reagent "H" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 17.39 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline of 7-17 carbon atoms were added in the alkyl group. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of the formula 67, 68, 69 and 70, in which R represents an alkyl group of 7-17 carbon atoms.

25

Example XXXVII

21.87 parts of Reagent Ί ”and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 18.13 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline of 7-17 carbon atoms were added in the alkyl group. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of formulas 71 and 72, wherein R represents an alkyl group of 7-17 carbon atoms.

35

Example XXXVIII

20.53 parts of Reaction component "G" and 60.0 parts of water were introduced into a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then 19.47 parts of 3-lauramidopropyl-diethylamine were added with good stirring. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of formulas 73 and 74, in which R represents an alkyl group with 11 carbon atoms.

45

Example XXXIX

18.29 parts of Reagent "C" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 21.71 parts of N-alkylethyl-N-hydroxyethyl-glycine (wherein the alkyl group is a lauryl group) were added. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of the formula 65, wherein R represents an alkyl group with 11 carbon atoms.

15 193247

Example XL

17.48 parts of Reagent "C" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 22.52 parts of N-alkylethyl-N-hydroxyethyl glydne (whose alkyl group contained 7-17 carbon atoms) were added. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of the formula 65, wherein R represents an alkyl group with 7-17 carbon atoms.

Example XLI

18.73 parts of Reaction component "B" and 60.0 parts of water were placed in a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 21.27 parts of N-alkylethyl-N-hydroxyethyl-glycine (in which the alkyl group was a lauryl group) were added. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of formula 75, wherein R represents an alkyl group with 11 carbon atoms.

Example XLII

12.60 parts of Reaction component "D" and 60.0 parts of water were introduced into a suitable reaction vessel with good stirring. Heat was supplied to a temperature of 50 ° C. Then, with good stirring, 27.31 parts of N-alkylethyl-N-hydroxyethyl-glycine (whose alkyl group was a lauryl group) were added. Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for another 4 hours. The conversion was complete when the inorganic chloride content reached the theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of the formula 76, wherein R represents an alkyl group with 11 carbon atoms.

Example XLIII

In a suitable reaction vessel, 15.73 parts of Reagent "A" and 60.0 parts of water were charged with good stirring. Heat was added to a temperature of 50 ° C. Then, with good stirring, 24.27 parts of N-alkylamidoethyl-N- were added. hydroxyethyl glycine (the alkyl group of which was a myristyl group) was added Heating was continued to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for an additional 4 hours The reaction was completed when the inorganic chloride content theoretical value and the residual amount of 3 ° N was negligible.

The product consisted of an aqueous solution of a new product of formula 77, wherein R represents an alkyl group with 13 carbon atoms.

Example XLIV

60.00 parts of soft water were placed in a suitable reaction vessel, after which 20.06 parts of 45 Reagent component "J" were added with good stirring. Heat was added to a temperature of 40-45 ° C, after which 19.94 parts of a 70/30 mixture of 3-lauramidopropyl-dimethylamine and 3-myristamidopropyl-dimethylamine were added with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 4-5 hours. The conversion was complete when the theoretical inorganic chloride content was reached and the residual amount of tertiary nitrogen was negligible.

The product consisted of an aqueous solution of the product of formula 78, wherein R represents 70% an alkyl group with 11 carbon atoms and 30% an alkyl group with 13 carbon atoms.

Example XLV

55.00 parts of soft water were placed in a suitable reaction vessel, after which 20.82 parts of Reaction component "A" were added with good stirring. Heat was supplied to a temperature of 45-50 ° C. Then, under stirring underwear, 19.18 parts of 3-lauramidopropyl-dimethylamine were added. Heating 193247 16 was continued to a temperature of 90-95 ° C, which temperature was maintained for 4-5 hours. The conversion was complete when the theoretical inorganic chloride content had developed and the residual amount of tertiary amine was negligible.

The product consisted of an aqueous solution of the product of formula 78, wherein R represents a 5 alkyl group with 11 carbon atoms (Example 23 of EP-B 13713 with a priority of November 30, 1978).

Example XLVI

60.00 parts of soft water were placed in a suitable reaction vessel, after which 24.45 parts of Reaction component "A" were added with good stirring. Heat was added to a temperature of 45-50 ° C, after which 15.55 parts of 3-capramidopropyl-dimethylamine were added with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 4-5 hours. The conversion was complete when the theoretical inorganic chloride content developed and the residual amount of tertiary amine became negligible.

The product consisted of an aqueous solution of the product of formula 78, wherein R represents an alkyl group with 5 carbon atoms (Example 25 of EP-B 13713 with a priority right of November 30, 1978).

Example XLVII

60.00 parts of soft water were placed in a suitable reaction vessel, after which 18.13 parts of Reaction component "A" were added with good stirring. Heat was supplied to a temperature of 45-50 ° C, after which 21.87 parts of 3-oleamidepropyl-dimethylamine were added with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 4-5 hours. The conversion was complete when the theoretical inorganic chloride content had developed and the residual amount of tertiary amine was negligible.

The product consisted of an aqueous solution of the material of formula 78, wherein R represents an alkyl group with 17 carbon atoms.

Example XLVIII

60.00 parts of soft water were placed in a suitable reaction vessel, after which 20.66 parts of Reaction component "A" were added with good stirring. Heat was supplied to a temperature of 45-50 ° C, after which 19.34 parts of 1-hydroxyethyl-2-alkyl-2-imidazoline of 7-17 carbon atoms in the alkyl group were added with good stirring. Heating was continued to a temperature of 90-95 ° C, which temperature was maintained for 4-5 hours. The conversion was complete when the theoretical inorganic chloride content had developed and the residual amount of tertiary amine had become negligible.

The product consisted of an aqueous solution of the material of formula 79, wherein R represents an alkyl group of 7-17 carbon atoms (compare Example 12 of EP-B 13713 with a priority right of November 30, 1978).

40

Example XUX

60.00 parts of soft water were added to a suitable reaction vessel, with 19.68 parts of Reaction component "J" being added with good stirring. Heat was supplied to a temperature of 40-50 ° C, after which 20.32 parts of 3-cocamidopropyl-dimethylamine were added. With good stirring, the reaction mixture was heated to a temperature of 90-95 ° C and kept at this temperature for 4-5 hours. The conversion was complete when the theoretical inorganic chloride content had developed and the residual amount of tertiary nitrogen had become negligible.

The product consisted of an aqueous solution of the material of formula 78, wherein R represents an alkyl group of 7-17 carbon atoms (Example 9 of EP-B 13713 with a priority 50 of November 30, 1978).

Example 1 Reaction component "A"

60.00 parts of deionized water were added to a suitable reaction vessel, with 22.58 55 parts of NaH 2 PO 4 and 0.70 parts of NaOH being added with good stirring. The mixture was stirred well until a solution was obtained. 17.42 parts of epichlorohydrin were then added with good stirring. The reaction vessel was closed, after which an excess pressure of 0.35 kg / cma was applied with nitrogen. The 17 193247 reaction mixture was heated to a temperature of 80-85 ° C and held at this temperature for 2 hours after the mixture became clear (about 3 hours in total). The conversion was complete when the theoretical reduction of the acid number was reached. The inorganic chloride content will be less than 0.50%.

The product consisted of an aqueous solution of a new product of the formula 17.

Example 2 Reaction component "B"

60.00 parts of deionized water were added to a suitable reaction vessel, with 17.37 parts of Na 2 HPO 4 being added. The mixture was mixed well until a solution was obtained. Then 22.63 parts of epichlorohydrin were added with good stirring. The reaction vessel was closed and placed under an overpressure of 0.35 kg / cm 2 with nitrogen. Subsequently, heat was added to a temperature of 80-85 ° C, after which the heated mixture was kept at this temperature for an additional 2 hours, after the mixture had become clear (about 3 hours in total). The conversion was completed when the theoretical chloride content was reached and the theoretical reduction of the acid number was effected.

The product consisted of an aqueous solution of a new product of the formula 18.

Example 3 20 Reaction component "C"

60.00 parts of deionized water were added to a suitable reaction vessel, with 17.37 parts of Na 2 HPO 4 being added. The mixture was mixed well until a solution was obtained. Then 22.63 parts of epichlorohydrin were added with good stirring. The reaction vessel was closed and placed under an overpressure of 0.35 kg / cm 2 with nitrogen. Heat was then added to a temperature of 80-85 ° C, after which the heated mixture was kept at this temperature for an additional 2 hours, after the mixture had cleared (a total of about 3 hours). The conversion was completed when the theoretical reduction of the acid number and the theoretical inorganic chloride content were reached. The product consisted of an aqueous solution of a new product of formulas 19 and 20.

30 Example 4

Reaction component "D"

60.00 parts of deionized water were added to a suitable reaction vessel, with 17.09 parts of NaH 2 PO 4 and 0.70 parts of NaOH being added. The mixture was mixed well until a solution was obtained. Then, with good stirring, 22.91 parts of epichlorohydrin were added. The reaction vessel was closed and placed under an overpressure of 0.35 kg / cm 2 with nitrogen. Then heat was added to a temperature of 80-85 ° C, after which the heated mixture was kept at this temperature for an additional 3 hours, after the mixture had become clear (about 5 hours in total). The conversion was completed until the acid number and theoretical amount had decreased. The inorganic chloride content will be less than 0.5%.

40 The product consisted of an aqueous solution of a new product of the formula 80.

Example 5 Reaction component "E"

To 51.21 parts of polyphosphoric acid was slowly added 48.79 parts of 2-chloroethanol with good stirring. The mixture was slowly heated to a temperature of 90-95 ° C and held at this temperature for about 2 hours. The conversion was complete when the theoretical reduction of the acid number was reached. Then, 35.67 parts of the product obtained in this way were mixed with 55.14 parts of deionized water. 8.32 parts of NaOH were then added slowly. The conversion was complete when the theoretical acid number was reached.

50 The product consisted of an aqueous solution of a new product of the formula 22 and / or 23.

Example 6 Reaction component "F"

66.17 parts of 1-chloropropanol-2 were slowly added to 33.83 parts of polyphosphoric acid with good stirring.

55 It was heated slowly to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for about 2 hours. The conversion was complete when the theoretical reduction of the acid number was reached. Then 34.90 parts of it was obtained in this way

Claims (4)

193247 18 product mixed with 60.00 parts soft water. Then 5.10 parts of NaOH were slowly added. The conversion was complete when the theoretical reduction of the acid number was reached. The product consisted of an aqueous solution of a new product of formulas 24 and 25. EXAMPLE 7 Reaction component "G" At 30.40 parts of polyphosphoric acid, slowly stirred with good stirring 69.60 parts of 2- [2- (2-chloroethoxyethoxy) ethanol] added. Then it was slowly heated to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for about 2 hours. The conversion was complete when the theoretical reduction of the acid number was reached. Then, 35.36 parts of the product obtained in this way were mixed with 60.00 parts of soft water. After this, 4.64 parts of NaOH were added slowly. The conversion was complete when the theoretical reduction of the acid number was reached. The product consisted of an aqueous solution of a new product of formulas 26 and 27. Example 8 Reaction component "H" To 31.91 parts of polyphosphoric acid was slowly added 68.09 parts of 3-chloro-1,2-propanediol with good stirring. . The mixture was slowly heated to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for about 2 hours. The conversion was complete when the theoretical reduction of the acid number was reached. Then, 35.17 parts of the product obtained in this way were mixed with 60.00 parts of soft water. After this, 4.83 parts of NaOH was slowly added. The conversion was complete when the theoretical reduction of the acid number was reached. The product consisted of an aqueous solution of a new product of formulas 28, 29, 30 and 31. Example 9 Reaction component Ί ”To 33.83 parts of polyphosphuric acid, underwear was slowly stirred 66.17 parts of 1-chloro-3-hydroxypropane were added . The mixture was slowly heated to a temperature of 90-95 ° C, after which the heated mixture was kept at this temperature for about 2 hours. The conversion was complete when the theoretical reduction of the acid number was reached. Then, 35.44 parts of the product obtained in this way were mixed with 60.00 parts of soft water. After this, 4.56 parts of NaOH were slowly added. The conversion was complete when the theoretical reduction of the acid number was reached. The product consisted of an aqueous solution of a new product of formulas 32 and 33. Example 10 Reaction component "J" To 60.00 parts of soft water in a suitable reaction vessel was added slowly with good stirring 21.17 parts of NaH2 PO3. Heat was supplied to a temperature of 40-50 ° C. Then 18.83 parts of epichlorohydrin were added with good stirring. The reaction vessel was closed and placed under an overpressure of 0.35 kg / cm 2 with nitrogen. The reaction mixture was heated to a temperature of 90-95 ° C and kept at this temperature for 3-4 hours. The conversion was complete when the theoretical reduction of the acid number was reached. The product consisted of an aqueous solution of a new reactant of the formula 34. 45 Phosphorus-containing betaine derivatives for industrial use, characterized by the formula 1 and 50 respectively, the formula 4, wherein AO®, OM or -OYR® represents BO® or OM ', X® represents an anion, z O or the number 1 or 2, 55 with the proviso that only either A or BO® can represent and z has a value necessary to provide charge equilibrium, Y an alkylene group, which can be interrupted by at most 3 oxygen atoms, with at most 12 19 193 247 indicates carbon atoms, which alkylene chain may be substituted by one or more alkyl, alkoxy, hydroxyl or hydroxyalkyl groups, with the proviso that in formula 4 the alkylene group Y is by one or more alkoxy, hydroxyl or hydroxyalkyl groups substituted, M and M ', which are the same or different, each (a) a hydrogen atom, (b) an organic radical from the group of 5 alkyl or hydroxyalkyl with up to 6 carbon atoms, polyhydroxyalkyl with up to 10 carbon atoms, glyceryl, cycloalkyl of up to 6 carbon atoms or aryl or aryialkyl of up to 10 carbon atoms or (c) a salt residue of the alkali metals, alkaline earth metals or mono-, di-triethanolamine, provided that either M or M ' an organic radical (b), the other radical M and M ', respectively, must be a hydrogen atom (a) or a salt radical (c), and R represents a radical of the formula 2 derived from an amidoamine reactant, in which formula 2 R 1 means an alkyl, alkenyl, alkoxy or hydroxyalkyl group each having 5-22 carbon atoms or an aryl or alkaryl group having not more than 20 carbon atoms, R2 means a hydrogen atom, an alkyl, hydroxyalkyl or alkenyl group having not more than 6 carbon atoms, 15 means a cycloalkyl group with at most 6 carbon atoms or a polyoxyalkylene group with at most 10 carbon atoms, R3 and R4, which may or may not be the same, each have an alkyl hydroxyalkyl or carboxyalkyl group having at least up to 6 carbon atoms in each of the alkyl radicals or a polyoxyalkylene group with up to 10 carbon atoms indicate whether R3 and R4, together with the nitrogen atom to which they are attached, indicate a nitrogen-containing heterocyclic radical, wherein the residues Y and Y 'represent another ring atom of the nitrogen-containing heterocyclic radical is then bonded to the nitrogen atom of the R radical, and n indicates an integer with a value of 2-12, or R is a nitrogen-containing heterocyclic compound of the formula 3, wherein ZN, S or O, 25 an integer from 0 to 3, p is an integer from 1 to 3, with the proviso that the sum of o + p is 3 to 4, and R is an alkyl, an alkenyl, an alkoxy or a hydroxyalkyl of 5 to 22 carbon atoms or an aryl or an alkaryl group of up to 20 carbon atoms and is attached to a carbon atom of the ring, and 30 Re is an alkyl group of 2 to 6 carbon atoms having a terminal or a non-end dental carbon atom can be substituted by a hydroxyl group. A compound according to claim 1, characterized by the formula 1, wherein A denotes OM, B denotes 0Θ, z is O and R, Y and M have the meaning as claimed in claim 1. A compound according to claim 1, characterized by the formula 1, wherein A indicates OM, B indicates OM1, z is O and R, Y, M and X have the meaning as defined in claim 1. A compound according to claim 1, characterized by the formula 1, wherein A is -O-Y-R®, B is O®, z is 1 and R, Y and X have the meaning as defined in claim 1. Hereby 14 sheets drawing