DE1912879A1 - Process for the preparation of polyether alcohols from 4,5-dihydroxy-1,3-dihydroxymethyl-2-imidazolidone compounds and use of the compounds for finishing textiles - Google Patents

Description

ΞΙί-ώΑΒΕΤΗ YOUNG, DR, VOLI t ^ f

: it! GfJC = :::!: i3 · SSEGESSTRAGSEÜC · TELEPHONE S4SOO?

GERHARD COLOEWEY

ESSE: INVENT / MONCKEN

UoZ ·: S 157 (Be / Vo)
POS-17 39S

SUMITOMO CIEMIOAI, ÖQMPÄFf, LSJD

Osaka, Japan

Process for the production of polyether alcohols from 4 »5-Di- *

from

Ho I4ärs 19β8 ₉ Japan, Kr, 16 919 / 6β April 26, 1968, Japan, Mr. 28 168/68

Pi © © te invention relates to methods for the preparation of l & lyätheralkohelen of 4 * 5

iasiaasolid, ^ compounds. The invention also relates to

© Iß procedures for the finishing of textiles und @ r

Rome

009815/1867

19128 * 9

their i? g? Eissla @ ?? ir> e?! $

giai is »

g ^ p possess & u

vtm hyäropMle »properties the disadvantages of a Yerscl ^ -tzirag when wearing v © ¹ « aa ^ aiis manufacturedii and a xmg & n & gBnüm Entfe ^ Kyieg \ ^? on Sehsrat ^ bein

3 · * as © defeat parts? 5i2 eliminating is of great importance were berttta Tt> rf

Remove the properties of textiles. »Es i © t

love «Bie shyly rush, like

Improvement * aear -ijesaititaa ^ iSsetiieK jsi ae properties 3aiie £ & af-c blaibs-u sol was in the USA Pateatselivlft J 049 44β fe ^ Tillen of hydropneumatic ~ iio ~ b @ n @ ^ * uh @ bi fflisoh Terspcanenen uj ^ op

from urea * formaldehyde and

satisfactory dirt removal

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old

Ea was found ^ & 3 fextiiioa lasersi cold

: i ^r f se ^£ i

eyntheti

sic sit ^ Ga

009815/1381

BATH ORIGINAL

which contain a group »which has an affinity for the hydrophobic synthetic fibers, eoarie a group that compensates for the disadvantages of ordinary hydrophobic synthetic fibers »without them excellent, the synthetic fibers peculiar property adversely affected. Such properties have been found to be possessed by certain polyether alcohols of 4,5-Dibydro: ^ - 1> 3-aihydro: cymethyl-2-: IJDQidazoliaon, which by Reacting certain alkyl ethers of this compound with a water-soluble polyalkylene glycol can be obtained can·

The process according to the invention for the preparation of polyether alcohols from 4 » 5-bihydroxy-1,3 ~ ßihydroxymethyl-2-imidazolid ^ .one compounds is characterized in that an alkyl-substituted 4,5-Mhydroxy-1,3-dihydroxymethyl-2-iraidazolidone general formula I.

R ¹ OCH ₉ -NN 1 I.

CH SH

I ₂ I

In ä & s &'t E ² , a ^r and H ^ denote hydrogen atoms or alkyl groups with 1 to 4 Ko ¥ Ienstoffatoaseis and at least one

''" τ-ζ A.lkylfp?« ppe with 1 to 4 carbon atoms

?> fj ω ο ι ς / ι ρ e- ^e ' ^:

1st, reacted with a water-soluble polyalkylene glycol with a molecular weight of 400 to 10,000 in a ratio of 1: 0.2

The invention also relates to the use of the products manufactured according to the invention for finishing textiles made from synthetic fibers or mixed fibers with cellulose. Basing methods for finishing textiles. Synthetic fibers or hishfibers made from synthetic fibers and Cellulosefaserη is characterized in that the textiles are impregnated with the polyether alcohols of 4-5-dihydroxy-1,3-dihydroxymethyl-2- imidazolid ^ one compounds in aqueous solution in the presence of an acidic catalyst, the solution up to a weight uptake of 0.5 to 10 Gevt.- ^c /> of the compound, based on the textiles, expressed and cures the fabric dried at a temperature up to 12O ⁰ C and then at a temperature from 130 to 170 ⁰ C.

The alkylated 4 »5 ~ dihydroxy ~ 1,3-dihydroxymethyl-2-imidazolid_one compound used as starting material in the production process according to the invention is known per se and is obtained by reacting urea» formaldehyde, glyoxal and a lower aliphatic alcohol with 1 to 4 carbon atoms in the presence or Absence of a solvent produced. The lower alcohol used has the general formula E ¹ OH, R ² OH, R ^ OH or R ⁴ OH, with methanol being preferred for economic and technical reasons * Be

009815/1867

as can
only one type of alcohol or / 2 to 4 types of alcohol can be used in the Gemisoh · Examples of solvents in this reaction are water, the alcohol used as the reaction component or a mixture of these solvents.

The compound used as the starting material is preferably prepared according to the following methods:

a) by reacting urea, GIyOXaI ₁ formaldehyde and a lower aliphatic alcohol with 1 to 4 carbon atoms in one stage, or

b) by reacting 4 »5 ~ dihydroxy ~ 2-imidazolidone, which has also been obtained from urea by reacting with glyoxal, with a lower aliphatic alcohol having 1 to 4 carbon atoms and then reacting the product obtained with formaldehyde, or

c) by reacting 4 »5 ~ 3> ihydroxy = ~ 2-imidazolidone, which has been obtained by reacting urea with glyoxal» with formaldehyde and then reacting the product obtained with a lower aliphatic alcohol having 1 to 4 carbon atoms »or

d) by reacting 4,5-dihydroxy-2-imidazolidone through Reacting urea with glyoxal has been obtained with formaldehyde and a lower aliphatic alcohol with 1 to 4 carbon atoms in one stage or

e) by reacting H, N ^e -Bi8-hydroxymetbylharaetoff or

009815/1867

ca Q we

a condensate of this compound obtained by reacting urea bit formaldehyde with glyoxal and then reacting the compound obtained with a lower aliphatic alcohol having 1 to 4 carbon atoms, or.

f) by reacting Ν, Ν'-bis-hydroxymethylurea or a condensate of this compound obtained by reacting urea with formaldehyde with a lower aliphatic alcohol having 1 to 4 carbon atoms and then reacting the product obtained with glyoxal, or

g) by reacting an alkylated N, N * ~ bis-hydroxymethyl ~> ureas or a condensate of this compound, which by reacting urea, formaldehyde and a lower aliphatic alcohol with 1 to 4 carbon atoms in a stage has been obtained, with glyoxal, or

h) by reacting urea, glyoxal and formaldehyde in one step and then reacting the product obtained with a lower aliphatic alcohol with 1 to 4 Carbon atoms, or

i) by reacting the product obtained by one of processes a) to h) with a lower aliphatic alcohol old 1 to 4 carbon atoms.

The water-soluble polyallylene glycols used in the process according to the invention are in particular polyethylene glycol,

009815/1867

Polypropylene glycol or a copolymer of ethylene glycol and propylene glycol.

The process is carried out in the presence of an acid. Examples of useful acids Bind p-toluenesulfonic acid, toluene ~ 2,4 ~ _f äiGUlfonsäure sulfuric acid, nitric acid, hydrochloric acid and phosphoric acid. It does not necessarily need a solvent for implementation used zn. For economic reasons, however, the use of Yfeseer as a solvent can be advantageous. The translation temperature is between 20 and 100 ° Ö.

The polyether alcohols of 4,5-dihydroxy-1,3-hydroxymethyl-2 "-iinida2olid. ^ One compounds prepared according to the invention are in water Ib'such. An aqueous solution of these compounds can be used to impregnate textiles

Textiles that can be finished according to the invention are hydrophobic synthetic textiles, preferably polyester textiles and textiles made from mixed fibers of hydrophobic synthetic fibers and cellulose fibers ^

According to the invention, the textiles are impregnated in water Solution carried out. The concentration of the compounds in the aqueous solution is 0.1 to 20 wt .-? S, preferably 1 to 10 wt .- ^ ·

009815/186?

The impregnation of the textiles is carried out in the presence of acidic kata analyzers carried out. The catalysts can be organic Acids, inorganic acids, or salts of a strong acid and a weak base, as are customary for the Resin finishing of textiles can be used. Examples of usable catalysts are zinc nitrate »magnesium chloride, Diammonium hydrogen phosphate, ammonium chloride, mineral acid salts of 2-amino ~ 2 ~ methylpropanol and ethanolamine, oxalic acid or maleic acid. Zinc nitrate or magnesium chloride are preferred catalysts. The catalyst can be in an amount from 1 to 100% by weight, preferably 5 to 50% by weight to the polyether alcohol compound.

The impregnation is carried out at room temperature.

Customary auxiliaries can be used in the impregnation solution used to finish the textiles. Examples of such auxiliaries are methylolurea, dimethylolethyleneurea, dimethyloluron, dimethyloltriazone, dimethylolglyoxal mono-ureid, dimethylolpropyleneurea or an alkylation product of these compounds. The use of one of these auxiliaries or of two different auxiliaries at the same time gives an excellent effect with regard to the durability of the treatment on the textiles. The quantitative ratio of the auxiliary to the polyether alcohol compound can be 20 wt .- ^ or more.

009815/1867

. " q -

You impregnated textiles are used to remove excess Solution squeezed out until the desired intake is reached the polyether alcohol compound has taken place. According to the invention the squeezing should be regulated to the extent that the intake the compound 0.5 to 10 wt, ~ £, based on the Textiles.

The impregnated textiles are then dried and hardened. If Palis is desired, drying and hardening can take place at the same time. The drying is at a temperature of 12O ⁰ C or lower, and requires about 1 to 10 mn. The dried textiles are then hardened. The hardening is carried out at a temperature of 130 to 170 ^° C. and usually requires about 30 seconds to 5 minutes. The polyether alcohol compounds are hardened to insoluble substances.

The textiles finished according to the invention have improved hydrophilic properties, resistance to renewed soiling and dirt-releasing properties due to the polyalkylene glycol chains in the molecule of the finishing agent. The imidazolidone ring of the compounds has a great affinity for hydrophobic synthetic fibers, such as polyester fibers, and, because of their reactivity with cellulose fibers, results in a finish of excellent durability. If there are many hydroxymethyl groups in the polyether alcohol compounds, textiles treated with them can

009815/1867

get improved crease resistance »

The invention is illustrated in more detail by the following examples.

example 1

* It has 4 "5-dimethoxy-2-imidassolidon that obtained by methylation of 4> 5 ~ dihydroxy-2-imidazolidone" orden had _t to 1.3 ~ dihydroxymethyl "4" nethyloliert 5-dimethoxymethyl-2-imidazolldon. 1.2 g of p-ioluenesulfonic acid were added to a mixture of 62 g of this compound and 180 g of polyethylene glycol with a molecular weight of 600, and the mixture was 40 KLn. ^{heated to 60 °} C. under reduced pressure of about 50 mm Hg · 14.5 g of methanol distilled off from the mixture, corresponding to 75 # of the theoretical amount · The product obtained was immediately diluted with water and neutralized with 5N sodium hydroxide solution in water. 450 g of a 50% strength aqueous solution were obtained.

The resulting solution was slightly yellow in color and transparent and viscous.

Example 2 2.5 Hol 37 # pormaldehyde solution, 1.0 Hol 40 tfige

009815/1867

Glyoxal solution, 1.0 mol of urea and 5 mol of isopropanol reacted with one another and 1,3-dihydroxymethyl-4 »5-dihydro:! Ey-2-imida & olidon with 1 * 7 mol of isopropoxy groups, substituted with xaopropyl groups, was obtained. 57 g of this were obtained compound with 300 g of molten polyethylene glycol with a molecular weight of 2,000 mixed "ZUÄHeaMioaeetmieeli was added 0.5 ml of concentrated hydrochloric acid and the reaction mixtures with stirring for 1 hour at 6O ⁰ C heated · to the resulting solution were added 50 ml of water and then 1.2 ml of a 5N Sodium hydroxide solution added for neutralization. The solution was heated under reduced pressure until 50 ml of distillate separated out. The isopropanol in the distillate was 10 g corresponding to 56 <fi of the theoretical amount. The product obtained represented a compound in which Imidazo! idinone rings were attached to both ends of the polyethylene glycol.

B e i s ρ i e 1 3

A mixture of 42 g of 1,3-3) iniethoxyraethyl-4f 5-dihydroxy-2-imidazolidone obtained by reacting N, K ⁽ -Bi8 (methoxymethyl) urea with glyoxal, and 10 g of water and 400 g of one molten copolymers of polyethylene glycol and 80 $ 20? ° polypropylene glycol having a molecular weight of 10 000 was added 0.5 ml of 70 ^ sulfuric acid and the resultant solution heated for 1 hour at 80 ⁰ C. After the reaction, the neutralized reaction mixture was

009815/1867

from a solvent mixture made from Diiaopropylftfaer and Waeeer cleaned. The elemental analysis of the product obtained showed that 1.7 inidasolid ^ one rings were bound to one molecule of the polyalkylene glycols.

At 8 ρ ie 1 4

Bas used in Example 3 1,3-dimethoxymethyl «4» 5-di »imidaeolidon hydroxy-2 ~ methanol was treated with excess la and a methylated 1.3 ~ £ ihydroxyinethyl ~ 4 ₉ 5-dihydroxy <-2 ~ imidazolidone with a degree of methylation of 3 t * get 5 There are 45 "5 g of the methylated compound with 320 g einee copolymers of 30 polyethylene" glycol and polypropylene glycol having a $ 50 Holekulargewioht of 800 gemäO example 3 implemented. Bb distilled from 18 g of methanol, corresponding to 80 f * of the theoretical amount · The resulting product was a viscous solution that was "vermisohbar with what.

Example 5

Eb Barnstoff were a 40 #ige GlyoxallSsung and 37 Jlige formaldehyde solution in a molar ratio 1,0x1,0: 2.5 x mixed Bas resulting mixture was hot 3 hours a pH from 7.0 to 7 Vert "5 to 6O ⁰ O heated and then the reaction product obtained to a solids content of

009815/1867

9G. # drained and narrowed. To the obtained compound was 10.0 Hol sugefUgt methanol and the obtained mixture at a pH of 2.0 Fourth for 1 hour at 3O vice etat ⁰ O and obtain a condensate of urea, glyoxal, and methanol with a Fonnaldehyd Methylierungsgraci 1.5 50 g of an 80% aqueous solution of this condensate were mixed with 300 g of polyethylene glycol with a molecular weight of 1,500. To the resulting mixture was added 0.5 ml of 70 #ige sulfuric acid and reacted for 1 hour at 70 ⁰ O. The conversion ratio was determined from the methanol formed to be approximately 80 % .

B e is ρ ie I 6

A mixture of 4 »5» dihydroxy-2-imidazolicon, 37-unit form aldehydic * solution and methanol in the ratio 1.0: 2.5 * 5.0 Refluxed for 90 minutes at pH 5.2 and a condensate with a Vert CH, 0- / N «0.55 obtained ·

were .

was implemented according to Beieplel 5, but / instead of the condensate 41 g of a 95% aqueous solution of the condensate was used. A product with a degree of etherification of 73 % was obtained.

009815/1867

Example 7

A 50 #igo aqueous solution of the reaction products obtained according to Examples 1, 2 and 3 was prepared. In each 100 ml of an impregnation solution made of water and 15 g of this 50.5% resin solution as well as 4 »5 g of a 30% aqueous solution of magnesium chloride, a filter made of Tetoron and cotton in a proportion of 65:35 was immersed and expressed with the help of a deficiency until the uptake of compound 7% by weight, based on the search, was. Thereafter, the cloth was dried for 2 Hinuten at 80 ⁰ C and cured for 3 Hinuten at 16O ⁰ C. The cloth was washed once and three times in a structural washing machine and the resistance to soiling of the treated surface was tested in each case. The crease resistance of the cloth obtained was also measured. The results are shown in Table Z below. As the results show, the treated Tuoh had clearly discernible beneficial durability and resistance to marine soil and improved wrinkle resistance.

009815/1867

^ - ^^
test 3815/1867 Impregnated cloth
^ \. untreated
deltes
cloth Cloth after
ST pre
script
impräg
ned Cloth with
product
from Bei
game 1
impregnated Cloth with
product
from Bei
game 2
impregnated Cloth with
product
from Bei
game 3
impräg
ned Ro 83.0 82.5 83.5 83.5 83.5 O
O Ysrschmut-
212BgS-
strength Reflection Rs 1
value
Re 3 63.0
65.0 63.0
63.0 78.0
'77.5 79.5
78.0 80.0
79.0 Degree of he j) _B ι
neuten
Dirt waste -q _b 3
fermentation, % 24.0
21.7 23.7
23.7 6.0
7.2 4.8
6.0 3.0
5.4 Crease resistance
(K «* t · + weft) 276 311 309 307 298

The ST-Vornchft refers to the use of 1.3 bydroxymethyl- "4,5 - aihydro: xy ~ 2" -imidazolidone instead of the invention manufactured urasal products

Resilience resistance was measured as follows;

Ea was an artificial soil containing Ö'3 from a mixture of 12.5% by weight? " Stearic acid, 12.5 wt .- '* oleic acid, 12.5 wt ₀ -JL hydrogenated coconut oil, 12.5 parts by weight * J $ ö olive oil, 5 parts by weight Cetyl iS "alcohol, 21.5 parts by weight # Solid paraffin, 5 * 0% by weight of choleaterin and 15.0% by weight of carbon black.

An artificial dirt was feeter w auβ a mixture of 55 wt .- ^ clay 17 G _e. · ^ Silicic anhydride, 0.5 part by weight 55 of ferric oxide, 17 parts by weight 5 'enent · Portland, 8, 75% by weight of heptane and 1.75% by weight of carbon black.

The artificial oily dirt was mixed with the solid dirt in a weight ratio of 3: 1. Three parts of this mixture and 7 parts of a nonionic detergent were dispersed in water and an aqueous dispersion with a concentration of 0.25 ^C A was prepared. The impregnated cloth was dirty, printed and dried 20 minutes at 40 ⁰ G using a Vereuchsgeräts "launder-o-meter" with the dispersion. The reflectance value at 550 became rough

009815/1867

: 5s impregnate ΐό-η i'iicha with the help of a spectrophotometer ge

The degree of the emitted screen deposition was calculated according to the formula

Ro - Rs 1 (or Rs 3)

Ds 1 {or Do 3) = - - "~~ T - ^ ™ ~ i χ 100

Ko

beötgets, where

Ro -ν reflection: of the impregnated! Cloth before soiling,

Ra «reflection of the impregnated cloth after soiling and

Rs 1 and Rs 3 * reflection values of the impregnated viewfinder »which were washed once or three times and then soiled.

The wrinkle resistance was determined according to the Monsanto method

JIS L-1041 C measured »where the recovery sw angle of chain and

Must be specified in degrees

009815/1867

Example 8

It was an impregnation bath of 100 ml from 8 g of the according to Bei «
3pial 2 manufactured product, 15 g of a 50 # aqueous
Solution of 4, S-Dihyflrostf-1,3-aihydro3cyH} 9thyl-2 <-iraidazolldon
and 4.5 g of a 30% aqueous solution of magnesium chloride with the addition of water. A cloth made of Tetoron and cotton in a proportion of 65:35 was immersed in the impregnation bath and expressed with the aid of a mangle until the absorption of product was 7.5% by weight. ~ ^, based on the cloth, was fraudulent. The cloth was 2 min. At 80 ⁰ O dried, and 3 min. At 160 ⁰ C
hardened, flexural strength against renewed pollution and the
The stiffness of the impregnated cloth was measured. The results are shown in Table IX.

IX

^^ ■ ^ - ^, ^^^^ Iiaprägniertee Tu oh
Examination ^^ ¹ *** ^ «^^^^ Ds 1
Bs 3 stiffness
(g / 20 mm) not iflh-
pragnant
tea cloth Do after
SJMfor-
sohrift
inconspicuous
ned Tuoh ge
mäa at
game 8
impräg
ned Degree of recurrence
Dirt deposits, % 25.0
23.5 26.0
25.0 6.0
6.6 89
• l 100 83

00981 5/1867

The cloth impregnated according to the ST regulation was impregnated according to Example 8 alone as per Example 8.

The stiffness was made with a "handle-o-raeter" from the company Thwing Albert Instrument Co. measured.

Aue Table II shows that the combined impregnation with a known resin together with the reaction product prepared according to Example 2 has a resistance to Obtained resurfacing of superior durability without the cloth losing its grip «

The reaction product obtained according to Example 5 shows similarly favorable results in the impregnation as the reaction product according to example 2.

Example 9

The reaction product prepared according to Example 3 was described below eammen zubi with an agent to achieve permanent ironed creases Used to impregnate a cloth. The impregnation was carried out according to Example 8. The results obtained are given in Table III.

009815/1867

TABLE III

Impregnated search

test

Degree of renewed dirt deposition

I) s 1 Da 5

Wash-and-wear properties

stiffness
(g / 20 imn)

Removability for engine oil

don't eat "präßüier" tes 2! uch

24.0 23.0

3.5

Cloth after S3! ~ Before ~ impregnated font

27.0 24.0

4.0

105

Cloth according to Bsi «" game 9 impregnated

4.5 7 * 0

4.7

78

The peelability for engine oil is measured by that a drop of motor oil (manufacturer Maruzen Sekiyu K.K «, Uo.40) is brought onto the cloth and then the cloth once is washed in a HauBhaltawaschraaschine «the detachment»

0098 15/186

■■ "· egg»

Capability is assessed according to the following values:

1 r »not completely removed.

2 ss somewhat detached.

3 ™ replaced in the usual way.

4 - almost completely replaced »

5 - completely detached.

Aim lab oll β III can be seen that the impregnation with a combination of a reaction product unit manufactured according to the invention and a scanned finishing agent for stirrup folds results in a favorable protection against renewed soiling and a good ability to remove motor oil without the ¥ aah-and-wear-ligands and the grip (stiffness) of the impregnated cloth are adversely affected

0 0 9 8 15/1867

Claims (10)

P A Ϊ E H ί A Ii S P 2 Il C H E ϊ Ι «Process for the production of polyether alcohol from 4 j 5-dihydroxy-1 , 3 - ü ihyd5? Oxyaiethyl ~ 2 ~ imida3olidonverbindungen, thereby geksn π ζ e I ch η β k that an alkyl-substituted 4 »5-dihydroxy-1 _? 5 = dihydroxymethyl-2- the al3.gemeiYien Porniel I (I) CH-OH ¹ SI 3 OR ^ OR ⁵ in which R, R, R ^ and R are hydrogen atoms ^v or alkyl groups with 1 to 4 carbon atoms and at least one of these groups is an alkyl group with 1 to 4 carbon atoms, with a water-soluble polyalkylene glycol with a molecular weight of 400 to 10,000 in a molar ratio of 1: 0.2 converts. 2. The method according to claim 1, characterized in that a compound of the general » 009815/1867 ~ 23 - My formula I is used in which at least one of the groups H ^1, R ^2, R ⁵ or R * is a methyl group . 3. The method according to claim 1 to 2 _S, characterized in that the water-soluble polyalkylene! Ycol · polyethylene uglycol, polypropylene glycol or a gopolynierieat of ethylene glycol and propylene glycol is used. 4 »Method according to claim 1 to 3 * thereby characterized in that the reaction is in the presence an acid. 5 * Method according to claim 4 »Γ & d u r c h g e indicates, that the acid p-l'oluenesulfone » acid, toluene-2,4 ~ disulfonic acid, hydrochloric acid, sulfuric acid, Nitric acid or phosphoric acid is used. 6. The method according to claim 1 to 5 _f, characterized in that the reaction is carried out at tteinperaturen of 20 bio 100 ⁰ C. 7 »Process for finishing textiles from synthetic Pipes or mixed fibers made from synthetic fibers and cellulose fibers, characterized in that that the textiles with the polyether alcohols of 4 »5 ~ 3) i- 0 0 9 8 15/1867 hydroxy-1,3-ai are produced according to claim 1, impregnated in aqueous solution in the presence of an acidic catalyst, the solution would take up to a weight of 0 ₉ 5 Ms 10 of the compound, based on the textiles, and the 2 textiles at a The temperature ^{dries to 120 0} O and then hardens at an oil temperature of 130 to 170 ⁰ O 8. Verfaliren according to claim 7, characterized in that the acidic Kfetalyestor an organic acid, an inorganic acid oi®r © in Salt of a strong acid with "a weak base is used. 9. The method according to claim 8, characterized in that the acid catalyst Zinc nitrate or magnesium chloride used " 10. The method according to claim 7 to 9 *, characterized in that the Polyätheralkohcl the 4,5 "-Uihydroxy-1 ^ -dihydroxyiaethyl-S-imidazolideavesrtiiiii" dung used in a concentration of 1 to 20 percent by weight. 11 «The method according to claim 7 to 10, characterized in that the acidic catalyst 0098 15/186 in an amount of 1 to 100% by weight, based on the polyether alcohol the 4 # 5-dihyroxy-1 »3« »dihydroxysiethyl-2-iiBida» olidone compound used" 009815/1867