DE2342432A1 - NEW HYDROXYALKYL COMPOUNDS AND THE PROCEDURE FOR THEIR PRODUCTION - Google Patents

Description

ΠΒΑ — GFIGY

ClBA-GElGY AG, CH-4002 Basel VwTiLJV ^ VJL-1VJ I

Case 3-8356 +

Dr. F. Zumstein.sen. - Dr. E. Assmann Dr.R.Koenigeberger - Dipl. Phys. R. Holzbauer

Dr. F. Zumstein jun. Patent attorneys

8 Munich 2, Brfiuhousttraß 4 / III

New hydroxyalkyl compounds and that Process for their manufacture

The present invention relates to new 1,3-bishydroxyalkyl-substituted ones Benzimidazolones and the corresponding benz-hydrogenated derivatives and a method for their production.

In the German Offenlegungssehrift (DT-OS) 1 95 ^ 503 is already the hydroxyalkylation of cyclic ureides, such as parabanic acid or barbituric acids and Ν, Ν-heteroeyeles with ureide structure., such as hydantoin or dihydrouracils described by the addition of alkylene oxides to these compounds. That way Hydroxyalkylation products obtained, however, have the disadvantage that, according to the process, they are insufficient Purity accumulate in order to be used for the production of high-quality plastics without being cleaned. So that they

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meet the requirements placed on them in terms of purity, they must be subjected to a cleaning process which, however, is complex and lossy in this case. The crystalline hydroxyalkylation products are predominantly low-melting substances that can only be obtained by repeated recrystallization in the ■ desired purity can be obtained. During vacuum distillation of the viscous hydroxyalkylation products In addition, signs of decomposition easily occur.

It has now been found that the addition of formaldehyde or certain alkylene oxides onto benzimidazolone or its benz-hydrogenated derivatives in very good yields 1,3-bis-hydroxyalkyl-substituted "compounds obtained which, surprisingly, can easily be brought to the purity required for the polycondensation can. So much for the new l, j5-bis-hydroxyalkyl compounds represent crystalline substances, they usually have a melting point of over 100 ° C and are easier to recrystallize. The viscous 1,3-bis-hydroxyalkyl compounds can also be distilled in a vacuum without decomposition.

Another advantage of the new 1,3-bis-hydroxyalkyl compounds lies in the fact that they look mostly lighter in comparison to the diols known from the DT-OS quoted polycondense with dicarboxylic acids and produce polyesters with better mechanical properties.

40981 0/1222

The present invention relates to new 1,3-bis (hydroxyalkyl) compounds of the formula I

HO-4CH4-CH - N N- CH-fCH4-OH (i) RR ₁ 0 ^, _R ,

■ 0
wherein X is a divalent radical of the formulas

means, R and R ¹ each independently represent a hydrogen atom, the methyl, ethyl or phenyl group, R ^ and R- * each. a hydrogen atom or R and R-. or, R, ¹ and R ^x together denote the trimethylene or tetramethylene radical and η denotes the number 0 or 1.

Preferably in formula IR and R 'each independently denote a hydrogen atom, the methyl or phenyl group, R, and R,' each denote a hydrogen atom or R and R, or R- ^,! and R ¹ .together the tetramethylene radical.

The new 1,3-bis (hydroxyalkyl) ~ compounds of the formula I are obtained by adding 1 mol of a compound of formula II

A09810 / 1222

i 1 (II)

H -

O
wherein X has the same meaning as in formula I, two

ßfol formaldehyde or 2 moles of alkylene oxide of the formulas

CH -— CH or CH CH (Ht)

Il-ti

R B ₁ - R ^ R ¹

wherein R, R ^r , R ₁ and R ^t _{1 have} the same meaning as in formula I * is added in the presence of a suitable catalyst. . -

The one used to prepare the new 1,3-bis (hydroxyalkyl) compounds of the formula I used compounds

of the formula II are benzimidazolone and tetrahydrobenzimidazolone and hexahydrobenzimidazolidone.

Compounds that correspond to formula III are ethylene oxide, propylene oxide, butylene oxide, styrene oxide, Cyelohexene oxide and cyolopentene oxide.

It is preferred to store compounds of the formula II formaldehyde, ethylene oxide, propylene oxide, styrene oxide or Cyelohexene oxide.

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The addition of the formaldehyde to the two NH groups of the compounds of the formula II can occur in the presence carried out by acidic, alkaline or neutral catalysts and also without catalysts , whereby there is a slight molar excess per equivalent NH group of the compounds of the formula II used in formaldehyde. The addition reaction is preferably carried out in a weakly alkaline or weakly acidic reaction medium carried out, the addition reaction already starting at room temperature and the reaction temperature can be increased up to 100 C.

The addition of an alkylene oxide of the formula III to the two NH groups of the formula II can be carried out in the presence can be carried out by both alkaline and neutral catalysts. This addition reaction also runs without it Catalysts. The reaction temperature for this addition reaction is generally between 50 and 180 ° C.

: Both addition reactions can also be carried out under pressure, that is to say in an autoclave. The addition reaction is preferably carried out in an organic solvent, such as dimethylformamide, toluene or dioxane or halogenated hydrocarbons.

Lewis acids, such as, for example, are particularly suitable as acidic catalysts for the addition reaction

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AlCl ,,, SbCl, -, SnClu, FeCl, ZnCl, BF- and their complexes with organic. Links.

As alkaline action catalysts are especially suitable tertiary amines such as triethylamine, tri-n-propylamine, benzyldimethylamine, N, N'-dimethyl aniline and triethanolamine; quaternary ammonium bases such as benzyltrimethylammonium hydroxide; quaternary ammonium salts such as tetramethylammonium chloride, tetraethylammonium chloride, benzyltrimethylammonium chloride, benzyltrimethylammonium acetate, methyltriethylammonium chloride; also ion exchange resins with tertiary or quaternary amino groups; also trialkylhydrazonium salts, such as trimethylhydrazonium iodide. The reaction may talysatoren 'also by adding other suitable Ka, for example, borax or alkali metal hydroxides, such as sodium hydroxide, and in particular by the acting neutral alkali metal halides such as lithium chloride, potassium chloride, sodium chloride, and fluoride -bfoinid accelerated v / ground.

The 1,3-bis-hydroxyalkyl-substituted according to the invention Hexahydrobenzimidazolidones can also be selected from the appropriately substituted benzimidazolone or tetrahydro benzimidazolone derivatives by catalytic hydrogenation are obtained, viobei this hydrogenation is carried out in a known manner both without pressure and under pressure can.

4 0-9 8 1.0 / 1 222

The 1, jJ-bis-hydroxyalkyl compounds according to the invention are partly high-rise crystalline, partly viscous Represent products which, according to the process, are already very pure. If an even higher degree of purity is required the crystalline products can advantageously be recrystallized in water. Leave the viscous products See distillation free of decomposition by vacuum distillation.

The 1,3-bis-hydroxyalkyl compounds according to the invention can be converted into polyesters by reaction with, for example, polycarboxylic acids, their alkyl esters or halides or by reaction with polyisocyanates in polyurethanes with very valuable mechanical properties be convicted.

Example 1: 1,3-bis (2 ^t -hydroxyethyl) benzimidazolone

To a solution of 402 g (J ₃ O mole) benzimidazolone and 3 g of lithium chloride in 1200 g of dimethylformamide at a temperature of l40 ^C to l48 ° C (Badtemperätur: l45 ° to 150 ⁰ C) within 110 minutes, a solution of 269 , 4 g (6.12 mol) of ethylene oxide in 3OO g of dimethylformamide were added dropwise. After a further 4-0 minutes of reaction time at 140 ° C to 145 ° C, the reaction is complete. The reaction mixture is concentrated to dryness in a rotary evaporator at 20 torr and the residue obtained is

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Post-dried at 90 C below 20 Torr. This gives 645 g (96.8% of theory) of a yellow powder with a Schmolz point of 145 ° to 158 ⁰ C.

The crude product can be purified by recrystallization in water in a ratio of 1: 2; you get the Pure substance in 76.9% yield; The product melts at 161.2 ° 'to 16.4 ° C.

Elemental analysis:

found: calculated:

59.56 % c 59.45 % c

6., 42 % H 6.55 % H

12.59 % N 12.60 % N

Das'protonenmagnetisehe resonance spectrum (H-NMR) is with compatible with the following structure:

HO - CH ₂ - CH ₂ - \\ - CH ₂ - CH ₂ - OH

Example 2: 1 ^ -Bis- (2'-hydroxy-n-propyl) -benzimidazolone

To 67.0 g (0.5 mol) of benzimidazoles »!, 15Ο ml of dimethylformamide and 1.0 g of calcium chloride are within 135 minutes at a temperature of 1 ^ 0 ° -l40 ° C (bath temperature: 150-162 C) 6l.0 g of propylene oxide were added dropwise.

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After 35 minutes, 10 g of activated charcoal are added to the reaction product and, after a further 13 minutes, it is filtered while hot. The clear brown filtrate is concentrated in a rotary evaporator at 90 C under water-jet vacuum and then dried at 9O ⁰ C and 10 ~ Torr to constant weight.

This gives 12 V7 g (99 ^ 6 % of theory) of a gray-brown, crystalline crude product / which is purified by recrystallization in water; its melting point is then 1 ^ 9 ° to 152 ° C.

Elemental analysis:. i

found : calculated :

; 62.20 % c 62.38 % c

j 7.07 % H 7.25 ^ H;

; 11.26 $ N li, 19 % N

The H-NMR spectrum is consistent with the following structure:

H-.C \ 7 CH-,

3 | > = <j 3

HO-CH-CH-N N-CH ₀ -CH-OH

² Y ²

Example 3: 1. » 3-bis- (2 ^! -Hydroxy-2'-phenylethyl) -benzimida-20 ion.

335 g (2.5 mol) benzimidazolones-601 g (5.0 mol) of styrene, 5 g Lithiumehlorid and 1000 ml of dimethylformamide at 120 ⁰ C to 163 ⁰ C (bath temperature: l40 ° C) for re-

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brought action, whereby the reaction device reacts exothermically. The reaction is complete after 2 hours and 1 hour and 30 minutes and the reaction product is concentrated in a rotary evaporator at 120 ° C./20 Torr. It is then dried to constant weight at 10 Torr. 921 ^ 8 g (98.5 % of theory) of a light, brown product are obtained. The H-NMR spectrum is agreed with the following structure

HO-CH- CH ^ - N N - CH ^ - CH - OH

w O

Example 4: \ ₃ 3-bis- (2'-hydroxyäthy1) -tetrahydrobenziraidazolon

69.1 g (0.5 mol) of tetrahydrobenzimidazolonj K6 _S J> g (1.05 mol) of ethylene oxide, 0.5 g of lithium chloride and 250 ml of dimethylformamide for 5 hours at 121 ° C to 128 ° C in an autoclave Brought reaction. The clear, brown reaction product is concentrated in a rotary evaporator at 100 ° C. under a water jet vacuum and then ^{dried to constant weight at 100 °} C. and 10 Torr. 123 g (99 ^ 9 ° of theory) of a brown, crystalline crude product are obtained, which is purified by recrystallization in isopropanol. Melting point άβε pure product: 152 ^ - 155.4 ⁰ C.

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Elemental analysis:

found : calculated :.

58.55 % C 58.39 % C 8.10 & H 8.02 % H

12.22 % N 12.38 % N The H-NMR spectrum is compatible with the following structure:

HO - CH ₀ - CH ₀ - N. N - CH ₀ - CH ₀ - OH ά. . c. C.

6 ■ ■

Example 5 * 1, ^ BIs- (2'-hydroxy-η-propyl) -tetrahydrobenzimidazolone

A mixture of 276.4 g (2.0 mol) of tetrahydrobenzimidazolone, 244 g (4.2 mol) of propylene oxide, 2 g of lithium chloride and 500 ml of dimethylformamide is reacted analogously to Example 4-. Working up is carried out according to Example 4 and 492 g (96 * 7 % of theory) of a brown, clear, highly viscous product are obtained. The H-NMR spectrum agrees with the following structure:

HO - CH - CH - N N - CH - CH - OH

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"ψ- ■ ■

Example 6 : 1,3-bis (2'-hydroxy-2'-phenyl-ethyl) -tetrahydrobenzimidazolone

27 * 6 g_ (0.2 mol) tetrahydrobenzimidazolone, 48.1 g (0.4 mol) styrene oxide, 0.3 lithium chloride and 80 ml dimethylformamide are 4 1/2 hours at 135 ° C to 156 ° C internal temperature (outside ent temperature: 166 C) brought to reaction. The cloudy solution is filtered and concentrated in a rotary evaporator, the clear Piltrat at 130 ⁰ C in a water jet vacuum. Then dry at 130 ° C and 10 ~ Torr until the weight is constant. 71.4 g (94.3 % of theory) of a brown, solid product are obtained, the H-NMR spectrum of which is compatible with the following structure:

HO-CH-CH-NN-CH _p -CH-OH

a ο

Example 7 ? 1,3-BiE- (2'-hydroxyethyl) -hexahydrobenzimidazolidone

a) In a 200 ml autoclave with magnetic stirrer 28.0 g (0.2 mol) of hexahydrobenzimidazolidone, 19.4 g (0.44 mol) of ethylene oxide, 0.2. g lithium chloride and 80 ml of dimethylformamide are added. The autoclave is

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• Y, -. ■

closed and the mixture is stirred for 5 hours at 120 ^° C., a pressure of 6 atü (atmospheric pressure) being established. After cooling, it is filtered, the brown solution is concentrated and then dried at 100 ° C./0.3 torr to constant weight. 4'2 g of a clear, highly viscous crude product (92.1 % of theory) are obtained. ', -'.

The crude product can be distilled for purification, the main fraction being obtained as a clear, light yellow, viscous oil ^{at 182-18; 5 o C / i), 2 Torr} existing solvent mixture) gives an RF value (retention factor) of 0.1, which corresponds to a sample of the compound produced in example 7 b),

Elemental analysis: '- Found : Calculated :

57.78 % C 57.87 % C 8.88 ^ H 8.83 $ H

b) - 45.2 g (0.2 mol) l,> bis (2 ^t -hydroxyethyl) -tetrahydrobenzimidazolidone (prepared according to Example K) and 5 g of Raney nickel in .200 ml of absolute ethyl alcohol are 12 hours at 120 ⁰ C and 140 atm. Hydrogenated. Man fil-

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the reaction mixture triturates and the filtrate is concentrated in a rotary evaporator at 9 ° C and a water jet vacuum. At 90 C and 10 torr until constant weight ,, and to obtain 43, 9 g (9 ^, 3 fo of theory) of a "gray greenish, viscous, cloudy product ,; which can be purified by vacuum distillation (K _n r = 213 ° -2l6 ° C).

p u, 0

Booty: 89.6 % of theory.

Elemental analysis:

found : calculated :

57.95 # C 57,? 7 fo C

9.07 % H 8.83 ^ H

12.03 ^ N 12.27 % N

The H-NMR spectrum has the following structural formula in line:

HO - CH ₂ - CH ₂ -N N- CH ₂ - CH ₃ - OH

Example 8: 1,3-bis (hydroxymethyl) tetrahydrobenzimidazolone

A mixture of 552.1 g (4.0 moles) of tetrahydrobenzimidazolone and 68l, 8 g of 37 tiger, aqueous formaldehyde (8.4 mol) are adjusted to pH 8 with 1 η sodium hydroxide solution and reacted at 59 ° -72 ° C. ! laugh is 10 minutes

4 0 9810/1222 BAD ORIGINAL "

• -ιί-

almost everything is dissolved, and 100 ml of water are added, the reaction temperature being kept at 75 ° C. The reaction is over after 4 hours. The reaction product is cooled and the substance which has crystallized out is then isolated by filtration. It is dried at 60 ° C./20 torr and ββγ g (84.1 % of theory) of a crystalline, brownish compound with a melting point of 155 ° -155 ° C. is obtained. Further amounts of the desired product can be isolated from the mother liquor.

Elemental analysis:

found : - ' calculated :

54.57 % C - 54.55 % C

7.15 % H 7.12 fan

14.28 fo N ₁ -. 14.13 % N

The new diol therefore corresponds to the following formula:

HO - CH ₂ - NN - CH ₂ - OH

11 0

Example 9 ^: 1,3-bis (hydroxymethyl]) benzimidazolone

. 40 g (0.3 mol) of benzimidazolone, 0.5 g of borax and 63 g of 30% aqueous formaldehyde solution (0.63 mol) are adjusted to pH 8 with 1 η NaOH and slowly heated. After 7, 16, 44 and 54 minutes, 10 ml of water are added each time

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country so that the Inn en temper a door increased within 44 minutes 9O ⁰ C. The reaction mixture is allowed to react for a further 15 minutes at this temperature, a dark brown, clear solution being formed. It is then cooled and the product which has crystallized out is filtered and washed in water. The crystals are dried at 8o ° C / 2O Torr and obtained 56.4 g (96.7 $ of theory) of brownish crystals having a melting point of 157.4 ° C ^o -l6l "

Elemental analysis: found: calculated:

C 55.75g C

N 14.4 $ N The H-NMR spectrum is compatible with the following structure:

HO-GH ₀ -IT JT-CH ₀ -OH

² \ σ / ²

Ii
0

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Example 10: lj3-bis- (2-hydroxy-n-t) utyl) - ben2iiniida.2! Oli5n-

Mixture of 53 ^ a ^ S C ^ Ä> l) Benzimidazolon., 12, T g MtMimtehlorid and 2 liier mmethylformamide is in aea? Glass apparatus with stirring, heated to 130 ° C., that is, ionized) of 2 strains of 634.5 S (8 ^ 8 mol) of 1,2-buta3.o3d.ö are added dropwise under rings The reaction lasts for another 6 hours at 150-153 ° ^C. After cooling, the reaction solution is made neutral by means of 5% sulfuric acid against solid indicator paper, and the filtrate is completely concentrated on the rotary evaporator. The residue is then dried at 120 ° C./0.5 torr until the weight is constant. 1188.6 g of crude product are obtained in the form of a dark, brittle resin (theory = 1112.0 g). ''.

For purification, the product can be recrystallized from acetone (ratio of substance: solvent = 1.2: 1). A colorless, fine powder is obtained which melts at 10 7.3 ° C. (Mettler FP 51 1 ° C./min). The proton magnetic resonance spectrum is consistent with the structure below. The thin-layer chromatogram shows that the substance is free of impurities (mobile phase: solvent mixture of cyclohexane, acetic acid ^{ethylates, and acetic acid in a ratio of 30:} 50-20), the RF value of the substance is 0.75

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found;

H N

US -

calculated;

7.97 ^ H ^ N

Example 11: 1,3-bis (2'-hydroxycyclohexyl) benzimidazolone

Analogously to Example 10, 201.2 g (1.5 mol) of benzimidazolone and 3 g of lithium chloride are stirred in 1.2 liters of dimethylformamide at 130.degree. ~ $ Κ ± g of 95 # cyelohexene oxide (3 * 3 mol) are added dropwise over the course of 2 hours. ^{The mixture is then stirred at 150 °} C. for a further 5 hours. Work-up is carried out as described in Example 10. 477.8 g of the crude adduct (96.4% of theory) are obtained. For purification, the product is ground and suspended in 3 liters V / water at 30.degree. The proton magnetic resonance spectrum shows that the desired product has been created.

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Example 12: 1,3-bis (hydroxymethyl) hexahydrobenzimidazolidone

A mixture of 164.6 g (1.17 moles) of hexahydrobenzimi-. dazolon and, 200 g 37 ^ iger, aqueous formaldehyde solution is stirred at room temperature by adding 3.2 ml of In MaOH the pH of the solution is brought to 8.0; an exothermic reaction begins. The temperature of the mixture increases without any heating from the outside to 4l C and the initial suspension turns into a clear solution. After the exotherm has subsided, the solution is heated to complete the reaction at 80 ° C. for a further 2 hours. The solution is then complete at 50 ° C. under a water jet vacuum constricted. The remaining oil crystallizes out after standing for a short time. The crystals were in ether / Suspended tetrahydrofuran (1: 0.8), then filtered off and dried. 169.2 g (72 * 3 $ of theory) of the are obtained desired product in the form of a pale yellowish colored powder, which at 93.4 ° C (Mettler FP 51; 2 ° C / min) melts.

For further purification, it was recrystallized from acetone. 130.0 g (55 * 5 # of theory) are obtained more glossy, more colorless to yellowish, prismatic crystals that melt at 100-102 ° C. The proton magnetic resonance spectrum is consistent with the structure below. The elemental analysis shows:

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found; calculated:

$ 54.3 C $ 53.98 C.

$ 8.0 H $ 8.06 H

$ 13.8 N $ 13

HO-CH ₀ -N IT-CH-OH
² \ / 2

Il

. 0

Application example '

A mixture of 56.6 g (0.25 mol) of the ^{1,3-bis (2 l} -hydroxyethyl) -tetrahydro'benzimidazolons obtained according to Example 4 and 48.6 g (0.25 mol). Dimethyl terephthalate is in the presence of 1 weight percent tetraisopropyl titanate

transesterified and polycondensed according to the following program in a laboratory glass apparatus:

2 hours at 150 ° C under a nitrogen atmosphere, 2 hours at 240 ° C / 30 Torr and

4 hours at 255 ° C / 0.2 Torr.

The product thus obtained is converted from chloroform / ether by reprecipitation cleaned. 73.8 g (82.8% of theory) of an almost colorless polyester are obtained, which according to DSC analysis (Differential Scanning Calorimeter) a glass transition temperature of 107 ° C.

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Comparative example

For comparison, dimethyl terephthalate and 1,3 "bis (2 ^f -hydroxyethyl) -5,5-dimethy! Hydantoin are mixed in a molar ratio of 1: 1, mixed with 1 percent by weight of tetraisopropyl titanate and transesterified under a nitrogen atmosphere at 180-210 ° C. for 2 hours, 80 mole percent ethylene glycol is added to this.After all the volatile constituents have been distilled off, polycondensation is carried out for 4 hours at 280 ° C./0.8 Torr.

It can be seen that with the diol according to the invention on simple way polyester with better color and higher glass transition temperature can be obtained than with the known diol, which has a very similar structure in terms of formula.

Example II

0.1 mol of terephthaloyl chloride and 0.1 mol of the 1,3-bis (2'-hydroxyethyl) benzimidazolone obtained in Example 1 together with 200 ml ο-dichlorobenzene in added to a round-bottom flask equipped with a stirrer, reflux condenser and nitrogen inlet. After introducing nitrogen 0.9 g of triethylamine and 0.02 g of magnesium shavings added as a catalyst and the reaction mixture under

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Stir and slowly heat to boiling under a nitrogen atmosphere. After 24 hours there is evolution of hydrogen chloride completed. After cooling the reaction mixture this becomes 1.5 liters of methanol were slowly added with vigorous stirring. The precipitating polymer is filtered off with pure Washed methanol and dried in vacuo at 120 C. The resulting polyester has the following properties:

Relative viscosity: 1.34

Glass transition temperature: 'I30 C Softening point: 178 ⁰ C

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Claims (20)

Claims 1. \ New 1,3-bis (hydroxyalkyl) compounds of the formula X HO-fCH4 ~ CH ~ N NOH4H4O RR ₁ ° R ₁ 'R · 0 where X is a divalent radical of the formulas means, R and R ^1, independently of one another, each represent a hydrogen atom, the methyl, ethyl or phenyl group, R and R, 'each a hydrogen atom or R' and R-, or R-. 'and R' together denote the trimethylene or tetramethylene radical and η denotes the number 0 or 1. 2. 1,3-bis (hydroxyalkyl) compounds according to claim 1, in which in the formula R and 'R' each independently represent a hydrogen atom, the methyl or phenyl group, R ¹ and R 1. each a hydrogen or R and R ₁ or R ¹ , and R * together denote the tetramethylene radical and X and η have the meaning given in claim 1. 409810/1222 3 l, 3-bis (2 ^t -hydroxyethyl) benzimidazolone. 4. l _i 3-bis (2 ^l -hydroxy - n-propyl) benzimidazolone. 5 l, 3-Bi ^s - (2 ^t -hydroxy-2 ^t -phenylethyl) -benziraidazolone. 6. l, 3 ~ ^bis (2 ^l -hydroxyethyl) -tetrahydrobenzimidazolone. 7 · 1,3 ~ bis ~ (2'-hydroxy-n-propyl) -tetrahydrobenzimidazolone. 8. 1,3-bis- (2'-hydroxy-2 ^! -Phenylethyl) -tetrahydrobenzimidazolone. 9. 1,3-Bi ^s ~ (2'-hydroxyethyl) -hexahydrobenzimidazolidone. 10. 1,3 "BiS (hydroxymethyl) tetrahydrobenzimidazolone. 11. 1,3-Bi ^s ~ (hydroxymethyl) benzimidazolone. 12. 1,3-bis (2'-hydroxy-n-butyl) benzimidazolone. 13. 1,3-Bi ^ß - (2'-hydroxycyclohexyl) -benzimida zolon. \H. l _> 3-Bi ^s ~ (hydroxymethyl) -hexahydrobenzimidazolidone. 15 Process for the production of new 1,3-bis (hydroxyalkyl) Compounds of the formula I. X -N N-CH-f CH ^ -OH (l) RR \ O
where X is a divalent radical of the formulas 409810/1222 means, R and R * independently of one another each represent a hydrogen atom, the methyl, ethyl or phenyl group, R, and R-. ' each a hydrogen atom or R. and R, or R 'and R 'together denote the trimethylene or tetramethylene radical and η denotes the number 0 or 1, characterized in that 1 mol of a compound of the formula II X HH 'HH. (II) - Π 0 wherein X has the same meaning as in formula I, two moles of formaldehyde or 2 moles of alkylene oxide of the formulas CH CH or - CH CH (III) Il "II- RR ₁ . R ₁ 'R ¹ wherein R, R ¹ , R ₁ and R ₁ 'have the same meaning as in formula I, is added in the presence of a catalyst. 16. The method according to claim 15 *, characterized in that that the alkylene oxide of the formula III used is ethylene oxide, propylene oxide, cyclohexene oxide or styrene oxide. · 17. The method according to claim 15 *, characterized in that that 1,2-butene oxide is used as the alkylene oxide. 409810/1222 18. The method according to claim I5, characterized in that lithium chloride is used as the catalyst. 19. The method according to claim 15, characterized in, that the formaldehyde is added between room temperature and 100 C. 20. The method according to claim 15 * characterized in that the addition of the alkylene oxide between 50 and
l80 ° C. PO 3.33 (Sta) Sta / Ge
May 3, 1973 409810/1222