CA1206167A - Bisphenol derivatives, process for their manufacture and their use as surfactants - Google Patents

Abstract

Abstract:

Bisphenol derivatives, process for their manufacture, and their use as surfactants Compounds of the general formula X-Y-O-(-A-O-Y-O-)m-A-O-Y-X (1) wherein X denotes a radical of the general formula [R1-Gp-(O-CHR2-CHR3-)n]2N- (1a) in which R1 is a saturated aliphatic radical having 6 to 30 carbon atoms or an unsaturated aliphatic radical having one or several ethylenic bonds and 6 to 30 carbon atoms, G is phenylene or naphthylene, p is zero or 1, R2 and R3 are hydrogen or methyl, but are not both methyl, and n is a number from 0 to 25, Y denotes a radical of the formula (1b) in which R2 and R3 have the indicated meanings and q represents identical or different numbers from 0 to about 200, A denotes a radical of the general formula (1c) in which R4 and R5 are hydrogen or alkyl having 1 to carbon atoms, and m is a number from zero to 5, n and not both being zero, are obtained by subjecting 2 moles of an amine of the general formula H-X (2) - 1a -in which X has the indicated meaning, to a condensation reaction with a bis-epoxide of the general formula

Description

The invention relates -to compounds of the general formula X-Y-O-(-A-O-Y~O-) A-O-Y-X (1) wherein X denotes a radical o~ the general formula 5 . [Rl-Gp-(o-CHR2-CHR3-)n~2N- (la) in which Rl is a saturated aliphatic radical having 6 to ~0 carbon atoms or an unsaturated aliphatic radical having one or several ethylen.ic bonds and 6 to 30 carbon atoms, G is phenylene or naphthylene, p is zero or l, R2 and R3 are hydrogen or methyl, but are not both methyl, and n is a ~umber ~rom O to 25, Y denotes a radical o~ the formula -CH2-fH-CH2- , (lb~
. t~CHR2~C~3) -OH
in which R2 and R3 have the indi.cated meanings and q 15 represents identical or di~ferent numbers from O to about 200~ A denotes.a radical of the general formula ~ C~4R5 ~ (lc~

. in ~hich R4 and R5 are hydrogen or alkyl having 1 to 3 carbon a~oms, and m is a number from zero to 5, n and q not both being zero.
Those compounds are pre~erred in which Rl is a saturated aliphatic radical having 6 to 20 carbon atoms ~r an unsaturated aliphatlc radlcal having 1 or 2 double bonds and 6 to 20 carbon atoms, in particular the radical o.~ a fatty alcohol. from natural f~t5 and oils, the .,, . - .

_ 3 ~ 7 radical of an alcohol from the oxo synthesis or the radical ol ~n alkylphenol or possibly also of an alkyl-naphthol, such as are conventional in the surfactant sector. Preferably7 p is zero; i~ i-t is 1J G is pre-ferably phenylene9 in par-ticvlar p-phenylene, n is a number from 1 to 15, q is a nv~ber from 10 to 100, R4 and R5 are hydrogen or methyl and m is zero. The polyoxy alkylene group in the formula (lb) is preferably a polyo~y-ethylene chain or a block copolymer chain of propylene oxide and ethylene oxide units q being a number from 10 to 100 The invention also relates to the preparation of the compounds of the formula (1), which comprises subjec-~îng 2 moles of an amine of the general formula H-X (2) in which X has the meaning indicated above, to a conden sation reaction with a bis-epoxide of the genera~ ~ormula H2C-~CH-CH2~0(~A-O-CH2-CH CH2~o3m~A--o CH2~C~I/CH2 (3 ~ OH
in which A and m have the meaning indicated above, at temperatures from 80 to 200C in the presence of an acid catalyst and reacting the condensation product with (m ~ 2)q moles of ethylene oxide and/or propylene oxide at 100 -to 200C in the presence of a basic catalys-t~ q having the meaning indicated abo~e The inven-tion also relates to the use of the cOmpOUnd5 of the formula (1) as surfacta~ts, in particular as dispersing agerlts. The compounds are especially suitable for dispersing solid~ in aqueous flUidS, in ..

particular for colorants, above all ~or pigrr.ents, particularly preferred ~ield of applica-tion is tne p-f para-tion of aqueous printing ir~s and emulsion pain~s, The starting materials of -the formula (2) are 5 kno~n from German Offenlegungsschri~t 2,555,895.
The bis-epoxides o~ the general for~.ula (3) can be prepared, for ex~ple, by reacting 2,2-bis (4 hydroxyphenyl)-methane, 2,2-bis-(4-hydroxyphenyl)-propan or 2,2-bis-(4~hydrox~phenyl~-butane wi-th epichlorohydrin (Ullmanns Enzyklopadie der Technischen Chemie ~Ullmanri's Encyclopedia of Indust~ial Chemistry~, 3rd Edition, 8th Volume (1957), pages 431 et se~.), The sur~actant properiies of the claimed co~lpounds result from the presence o~ hydrophilic and hydrophobic structures in the molecule~ the hydrophilic properties essentially being provided by the polyoxyalkylene chair~, The desired surfactant properties can be influenced within wide limits by the selection of the star-ting materials of the ~ormulaè (2) and (3) on the o-ne hand a-~d by the nature and quantity of the alkylene oxide on ~he other hand, Advantageouslyg the ~uantity of alkylene oxide is such that compounds are ob~ained ~Jhich give clear solutions in water.
The condensation of the compounds (2) and (3) is advantageously carried out at temperatures ab~ve 100C, in particular at t~lperatures between 1.20 and 180C.
It ls expedient -to carry out the reaction with exc-lusion o~ oxygen, Aci.d ca~alysts whicll can be used are~ in part-cular~ ~ewis acids~ for examp1e alumin~ chloride, 5 ~
boron trifluoride/ether complexes or phenols The oxyalkylation of the conde~,ation products obtained from the amines (2) and bis--epoxides (3) is expediently carried out in the presence of strongly basic catalysts, such as potassium hydroxide, sodium h~;droxide or alkali metal alcoholates, for example sodium methylate.
Adv~tageously, the temperature is in the range from 120 to 180C, in particular between 150 ard 170C The oxyalkylation can be carried out with etnylene oxide alone or ~fiith a mixt~re of ethylene oxide and propylene oxide It is also possible, ho~ever, first to intro-duce a polyoxypropylene chain into the surfactant mole-cule9 by means of propylene cxide, and +vhen to introduce a polyoxye+vhylene chain by means o~ ethylene oxide.
The quantity o~ ethylene oxide preferably is such that the compounds obtained are readily soluble in water, The oxyalkyla-tion can be carried out ~Ji-thout pressure or in pressure vessels, The pre~erred working p-~essure is 2 to 8 bars.
The surfactal~vs acc.ording vo ~vhe inv~ntion are suitable ~or dispersing solids, in par-ticular in aqueous fluids Dispersions which contain, for example, ~ine~y particulate ores, minerals, sparingly soluble or insoluble salts, wax particles or plastic particles, plant protection agents and pesticides and optical brighteners, in particular d~yes and pigments, as the solids may be mentioned, The suitability of -~he surfac-cants according to the invention for the prepara-tion oi pigment dispersions ~ 6 - ~ Z~6 ~ ~
should be particu].arly singled out Pigment dispersior.s of this type can contain inorganic and/or o~ganic pig-ments Examples of suitable inorganic pigments a~e white pigments and colored pigments9 such as titani.um oxides, zinc oxides, æinc sulfides, cadmium sulfides or cadmium selenides, iron oxides, chromium oxides, chromate pigments and mixed oxides suitable as pigments and obtained from the elements aluminum, antimony, chromium, iron, cobalt, copper, nickel, titan_um and zinc, and also ~rades of carbon black and extender pigmen-cs.
'~he following may be mentioned as examples of sui~able organic pigments: azo pigments, azamethines, azaporphines, quinacridones7 ~lavanthrone compound.s, anthanthrone compounds and pyranthrone compounds, deriva-tives of naphthalene tetracarboxylic acid, of perylenetetracarboxylic acid, of thioindi~o, of dioxazine and of tetrachloroisoindolinone, laked pigments, such as the Mg, Ca, Sr, Ba,. Al, Mn, Co and Ni salts of dyes containing acid groups, and also corresporlding pi~ment mixtures.
In addition to the surfactants according to the invention, the solids dispersions can also contain ..vrther co~ventional additives, such as foam reO~ulators and viscosity re~llators, anti~sett7ing agents, ~etting agents and solvents, hydrotropic agents, preservatives, agents ~hich prevent or retard drying up, and anionic, cationic, non-ionic or amphoteric known surfactants and pro-tective collnids The kno~n surfactants can be those ~ ich are des-cribed, ~or ex~ple, in K Lindn.er: Tensid~, _ 7 . ~%~6~L~7 Textilhil~smittel, llaschrohstoffe [Sur~actants, Textile Auxiliaries, Detergent Raw Materials~, in N Sch~r~eld~:
Grenzfl~chenaktive ~thylenoxydaddukte, ihre Hérsiellung, Eigenschaf-teil, Anwendung und ~nalyse [Surf'ace-act--~e ethylene oxide adducts7 their manufacture, properties, use and analysis~ and in McCutcheon, Detergents &
Emulsi iers, International Edition 1978.
The preservatives can be substances such as have been compiied, for example, by K -H Wallhau~er and W
Fi.nk in Farbe und Lack9 Volume 82 (1976), No. 2, pages Sui~able additives ~Jhioh prevent or retard drying-up o~ the solids dispersions are above all subs-t&nces which have a low volatility and complete or limited mis cibility with water, such as, for example, polyhydric alcohols as well as their ethers and -tneir reaction pro-ducts ~th ethylene oxide or propylene oxide, in parti~
cular glycols,.glycol ethers and polyglycols, and acid amides, in particular formamide9 urea ~nd 1-methyl-2~
pyrrolidone. Addi.ti.ves of this type can be used alone or a~ a mixture with one another Depending on the hardness of the par-ticles of -the solids ~sed, the preparation of the solids dispersions can be ca.r:ried out, for example, by means o~ agita-tors, dissolvers, rotor/s~ator mills, ball mills, stirred ball ~ills (sand mills or bead mills), in high-speed mixers, kneading apparatus sr on roll mills.
~ re~erred dispersions contaln 4 to 85, preferab'ly 30 to ~0, % by weight o~ solids., 1 to 30, preferably 2 z~
to 15, S' by weight of -the sur~actants according to ~ e invention and 5 to 95, preferably 10 to 60, % by ~,Jeigh-t of water includi~g further possible additives Solids dispersions ~ihic'n co~tain the surfactants according to the invention have a high stability and a high solids content, coupled a-t the same time w_th good rheological proper-ties I~ pigments are used as the solids, pigment dis-persions are obtained which are versatile in use The-y are suutable, for example, ~or coloring (pigme~ting) emulsion paints and wallpaper paints, water~dilu-table lacquers, wood stains, paper pulpsg printin~ ir)ks fo~
textile printir~, gravure printing, flexographic printing and other printing processes, and for use in spin-dyeing.
1~ The good d~spersing properties o~ the sur~actants according to ~he invention ]ead to pigment dispersions having a high tinctorial strengt~ and brigh-tness Com-pared with pigment dispersions containing conventional surfactants, the pigmen-t dispersions contajning -the sur-Z0 factants according to the invention are distinguisned by a broad compatibility with the most diverse aqueous binder systems, in particular aqueous printing inks, an~ a par ticularly high s-tability -to floccula~ion, abo~e all in co~parison with plastic dispersions and pain-ts contain-ing cellulose ethers.Examples o ~x~p_e 1:
~40 g of an ether~amine of the formula [Rl-(0-CH2 CH2)5~2N~I in ~hich p~l represents the alkyl ` - ` g ~L2~61~i7 radical of coconu-t fatty alcohol (having a mean molecv.lar weight of 880), 72.6 g o~ a diglycidyl e-ther of 27 2~
b.is~(4-hydroxyphenyl)-propane (Epon number lg3, molecular weight found to be 378) and 0 6 g of pheno~ as a catalyst are initially in-troduced into a 500 ml flask ~itted with a reflux condenser, stirrer and internal thermometer, and the mixture is slowly heated -to 150C under a nitrogen atmosphere and is kept at this temperature for 16 hours After cooling1 a yellow9 viscous fluid having an Epon nu~ber of less than 1 is obtained.
a) 162 g of the addition product obtained are oxy-ethylated wilh 190 g of ethylene oxide at 170~C in a pressure vessel, in the presence of 0.75 g of po~.Tdered potassium hydroxide The wa~y reaction pî oduct OL pale bro~nish color has a turbidity point of 73C in water ~according to DIN 53~917)o b) 115 g of the addition product obtained are reacted, after -the addition of 1 g of powdered sodium hydroYide, in an autocla~e with 285 g of ethylene oxide. The brownish waxy surfac-tant has a turbidity point of 91C
c) After mixing wi-th 1 3 g of sodium hydroxide powder, 130 g of the addition product obtained are reacted in a pressure vessel with 17 g o~ propylene o~ide and subsequently wi~h 172 g of ethylene o~ide. The waxy, mixed oxyalkyla-te shows a turbîdity point of 73C in aqueous solution.
ation E a~ple 2: -Corresponding t~ Example 1, 253 g o:E an additionproduct oE 2 moles of an e-ther~-ne of the formula .

.

_ lo- ~2~6~
[C~7~133-(0-CH2~CH2~)12]2NH and 1 mole of ~e diglycidyl ether of 2,2 bis-(4-hydroxyphenyl)-propane are cxyethyla~
ted, in the presence of 1 g of potassium hydroxide powder, with 618 g of ethylene oxide at 170C in a pres-sure vessel The brownish, waxy surfacta~t obtained . has a turbidity point of 90C in ~rater Preparation Exam~le 3:
Analogously to Example 1, 230 g of ethylene oxide are added in the course of 6 hours to 185 g of the addi -tion product of 2 moles of -the ether-amine from Example 1 and 1 mole of the diglycidyl ether of 2,2-bis-(4-hydroxyphenyl.~-methane in a pressure ~essel, in the ~re-sence of 0.5 g of sodium hydroxide powder. The result-ing brotmish, waxy surfactant has a turbidity point.o 80C in wa~er.
_re~aration Exam~e 4:
1~0 g of the secondary ether-amine from F.xampl~
1 are, with the addi-tion of 0 5 g of phenol, reac'æd a~
described in Example 1 wlth 95.5 g of a compound of the

2~ ~ollowing formula CH2-C}l-Cil2-o- ~-C; ~-O-CH2 ~ ~I Ci 2 ~) ~ ~)-o-c~l2-cH-~`H2 - .4 1 g of potassium hydroxide powder is added to 150 g of this reaction product, and the mix-t~re is reac-ted-in a press1~re vessel with 147 g of ethylene o~ide at 160C.
The bro~mish, waxy polyoxyalkylate shows a ~u-r~idity . ', .

'6~67 point o~ 77C in aqueous solution Preparatio:~ ~x~ple 5:
Corresponding to Example 17 16g g of an adduct of 2 moles of an ether-amine of the formula ~R -(0 CH2-CH2~)8~2NH in ~Jhich R~ represents the alkyl radical of tallow fa-tty alcohol, and 1 mole oi the di-glycidyl ether of 2,2-bis-(4-hydroxyphenyl)-propane are reacted, after Ihe addition of 1 g of sodium hydroxide powdeL, ~ith 110 g of e-thylene oxide The turbidity point of ~e brownish, waxy surfactant is 72C~
Preparation ~
Correspo~ing to Ex~lple 1, 295 g of an adAuct of 2 moles of an ether-amine of the formula ~R -(O-CH2-CH~ 0~2NH in which Rl repr~sents the alkyl radical o~ coconut fatty alcohol, and 1 mole o~ the diglyoidyl ether of 2,2~bis~(4~hydroxyphenyl)-propane are reacted, a~ter the addition OT 1 g of so~ium hydroxide po~der, with 226 g of e~hylene oxide. The ~axy, bro~ish polyoxyalkylate has a turbidity point Gf 74C
in water.
Preparatio Example 7:
Corresponding to Exa~ple 1, 161 g o~ an adduct o~ 2 moles of ether-amine of ~he formula ~iso-C13~I27~(0-CH2~C~2)~2~rI and 1 mole of the diglycid-yl ether o~ 2,2-bis~(4-hydroxyphenyl)~propane are reacted, after the addi-t.ion of 1 g of sodium hydroxide powder, wil;h 197 g o~ e-thylene oxide The b~o~,mish reaction producl; obtained h~; a waxy conslstency and has a -~urbidi~y pOillt OI 78~ in ~ater, - 12 ~ 6 arat on Exa~.ple 8:
- Corresponding to Example 1, 210 g of an additio:n product of 2 moles of a secor~ary ether-amine of ~e formula [R -(O~CH2-CH2)5~2~
in which Rl represents a4-isononylphenyl radical, and 1 mole of the diglycidyl ether of 2,2~bis-(4~hydroxyphen-yl)-propane are oxyethyla-ted, in the presence 013 0.9 g 0l potassium hydroxide powder9 with 242 g of ethylene oxide at 170C in à pressure vessel. The brownish waxy surfactant obtained has a turbidity point of 80C in w~ter.
In the applica-tion examples ~ich follow, par-ts are parts by weight, 7.5 ~$~______n Exam~le 1:
._ ..._ 700 parts of ground dolomite are dispersed by means of a dissolver for 0.5 hour in a mixtur~ of 10 parts o~ oleic acid, ~0 parts o~ the surfactant from Preparation Exa~ple 2 and 193 parts of water, with the addition of 10 parts of highly disperse, pyrogenic silica. By the addition of 57 parts of water~ a flowable, slightly thixotropic and pumpable dispersion having good storage stabili-ty is obtained ;~,li--D ~3 D :~
700 parts of an iron oxide red pigment are in-troduced in portions into a mixture of ~ Z ~r k~ 7 - 13 ~
40 parts of ~he surfactant from Preparation E;~ar~le 3, 5 parts of tallow-fatty alkyl-propyle-nediamine, 100 parts of 2 ethyl-2-(hydroxymethyl~-propane~ diol and 130 parts of water and are dispersed by means of a dis-. solver do~ to a particle fineness smaller than 5 ~m, After dilution with 75 parts of water, a pigment preparation having goodrheological properties is obtaine~, which is particu~
10larly suitable ~or coloring aqueous paints based on plastic dispersions.
When this pigment preparation is stirred, for example in a concentration of 2,b by weight9 into an emul-sion paint which contains a copolymer of styrene and an acrylate as the binder and a methylhydroxyethyl-cellulose as the cell-llose ether, and the colored dispersion paint is brushed onto paper, a deep coloring is obtained ~ich does not show any flocculation phenomena in the rub-~ut test ~German Auslegeschrift 2,6~8J946, column 3).
~ID~ "Id'D~-s~3~t-~
. Corresponding to Application Example 2, a pigment dispersion o~
. 800 parts of a chromium oxide green pi~ment, ; 22 parts of the surfactant from Preparation E~ample 2,

3 parts o~ M~oleoylsarcosine, 50 parts of ethylene glycol and 125 parts of water is prepared, The properties of this pigmen-t ~ispersion are comparable ~ith those o:
the dispersion o~ Application Example 2~

2~ 6 ~lication Exa~]e 4:
... . . ..
370 parts of C I, Pigment Violet 23 (Colour Index No, 51,319) which, on finishing, has been modified accor~ing to Example 12 o~ Ger~an Ausle~eschri~t 2,731,175, are dispersed in -the presence of 100 parts o~ the surfactant from Preparation Example lc ~nd 150 parts of ethylene glycol, in a -twin~trough kneader~
Subsequently, the kneading composition is diluted lQ with 110 parts of ethylene glycol, 268 parts of ~ater and 2 parts o~ a preservative to give a storage-stable dis-persion ~ich has very good rheological properties .and which is particularly suitable for coloring aqueous binder systems for the paint sector and tex--tile pi~lent printing When this pigment dispersi.on, for example in a concentration of 1% by weight, is s-tirred into the -emulsion paint described in Application Example 2 and is spread on paper, this gives deepg bright colorings and . .
.. a fault-free rub~out test.
Comparably good results are achieved ~en the 100 par-ts of the surfactant from Preparation Example lc are replaced ~y 100 par-ts o~ the surfactant from Preparation Example la and the 260 parts of ethylene glycol are repl.aced by 260 parts of fo~m~nide, lication Example 5:
Corresponding to App~icat.iDn Example.4, 400 parts of C I Pigmen-t Red 168 (Colour Index No 599300) are dispersed wit~
80 parts of the surfact&~t ~rom Preparation Example 6 and 115 par-ts of 1,2-propanediol in a kneader, ~nd the mIxture is diluted ~lith a further 35 parts of 1,2-propanediol and 370 parts of ~ater to give a very highly flowable ~isper-sion which, abo~e all in the sector of aqueous paints based on plastic dispersions, all~rs -~e excellent coloristic properties and the good flocculation stability -to be fully developed.
A pigment dispersion having similarly good pro-perties is ob-tained whe~ the 80 parts of the s~factan~
from Preparation Example 6 are replaced by 80 parts of ~he surfactant from Preparation Exa~ple 4 and the 150 parts of 1,2-propanediol in total are replaced by 100 parts of glycerol and 50 par-ts of 1-methyl-~2-pyrrolidone.
Application Example 6:
480 parts of Pigmen~ Red 112 (Colour Index No~ 12,370) are dispersed for 1 hour~ in a twin-trough ~neader, ` - wi~ .
90 parts o~ the surfactant from Prepara-tion Example lb, 10 parts of the sodium salt of a sulfuric acid half-ester of an adduct of 7 moles o~ ethylene oxide and l mole of tributylphenol, 100 parts of ethylene glycol and 70 parts of water Subse~uently, the kneading com- -position is diluted by the addition of 16 , 250 parts of water to give a storage-stable1 mobile pig~
ment preparation which is outstandingly suitable for coloring aqueous flexographic printing inks or gravure printing inks and for pigmenting aquecus paints based on plastic dis~ersions, Ap~l~.cation Exam~le 7:
420 parts o~ a pigmen-t carbon black having a specific surface area according to BET of 85 m2~g are stirred into a solution o~
60 parts of the surfactant from Preparation Example la, 100 parts of ethylene glycol and 340 parts of water, This suspension is ground in a stirred ball mill with 1 mm S.iliquartzite beads and is then dilu~ed by the addition o~
80 parts of water, The storage-stable pigment dis-persion obtained in this way is outstandingly suitable for use in aqueous flexogr-aphic printing inks and gravure printing inks.
eE~l_____on Ex-ample 8:
450 parts of a pigment obtained by mixed coupling of diaæotiæed ~J3~-dichlorobenzidine with acetoacetic : acid anilide and acetoacetic acid p-ani.sidide in a ratio of 9:1 are dispersed wi-th 80 parts c~ the surfactant from Prepara-tion Example 5 ~nd 160 parts of w~ter for 2 hours in a twin-trough kneader, By the addition of 100 parts o~ eth~Jlene glycol and 210 parts o~ water, a mobile pigment preparation is -~ 17 ~ Z~6~
obtained ~ich can oe diluted further ~Jith ~/ater i~
a~y proportionc It is particularly suitab'e for coloring water-con-taining binder systems, In a stirred ball mill, a suspension o~
. 450 parts of C.I, Pigment Green 7 (Colour Index No.
74,260), 60 part,s of ~e sur~actant ~rom Prepara-tion Example lc, ~0 parts of an adduct o~ 11 moles of ethylene oxide a~d 1 mole o~ nonylphenol, 50 parts of urea, 100 parts of diethylene glycol, 258 parts of water and 2 parts of a preservative is ground with 1 mm Siliquart~ite beads ~nd is then diluted -~ith a further 40 parts of water to give a pigment dispersion having - very good r'neological properties, It is suitable above all for pigmenting aqueous paints based on plastic dispersions, in which case it is distinguished by a high flocculation stability and good coloristic properties, . Pigm~nt dispersions having com~arably good pro-per-ties are obtained when the 60 parts ~f the sur~actant ~rom Preparation Example lc are replaced by 60 p~rts of the sur~actant ~rom-Preparation Example 7 or 8.

Claims (11)

1. A compound of the formula X-Y-O-(-A-O-Y-O-)m-A-O-Y-X
wherein X is a radical of the formula [R1-Gp-(O-CHR2-CHR3-)n]2N-in which R1 is a saturated aliphatic radical of from 6 to 30 carbon atoms or an unsaturated aliphatic radical having one or several ethylenic bonds and 6 to 30 carbon atoms, G is phenylene or naphthylene, p is zero or 1, R2 and R3 are hydrogen or methyl, but are not both methyl, and n is a number from 0 to 25, Y is a radical of the formula in which R2 and R3 are as defined above and q represents identical or different numbers from 0 to about 200, A is a radical of the formula in which R4 and R5 are hydrogen or alkyl of from 1 to 3 carbon atoms, and m is a number from zero to 5, n and q not both being zero.

2. A compound of the formula X-Y-O-(-A-O-Y-O-)m-A-O-Y-X

wherein X is a radical of the formula [R1-Gp-(O-CHR2-CHR3-)n]2N-in which R1 is a saturated aliphatic radical of from 6 to 30 carbon atoms or an unsaturated aliphatic radical having one or several ethylenic bonds and 6 to 30 carbon atoms, G is phenylene or naphthylene, p is zero or 1, R2 and R3 are hydrogen or methyl, but are not both methyl, and n is a number from 0 to 25, Y is a radical of the formula wherein Z is a polyoxyethylene chain or a block copolymer chain of propylene oxide and ethylene oxide units, the number of said units being of from ten to 100 and being different or the same from one radical to another, A is a radical of the formula in which R4 and R5 are hydrogen or alkyl of from 1 to 3 carbon atoms, and m is a number from zero to 5, n and q not both being zero.

3. A compound of the formula X-Y-O-(A-O-Y-O-)m-A-O-Y-X
wherein X is a radical of the formula [R1-Gp-(O-CHR2-CHR3-)n]2N-in which R1 is a saturated aliphatic radical of from 6 to 30 carbon atoms or an unsaturated aliphatic radical of from 6 to 20 carbon atoms and containing one or two double bonds and, G is phenylene, p is zero or 1, R2 and R3 are hydrogen or methyl, but are not both methyl, and n is a number from 1 to 15, wherein Y is a radical of the formula in which R2 and R3 are as defined above and q is a number from 10 to 100, being the same or not the same in the "X" radicals, wherein A is a radical of the formula in which R4 and R5 are hydrogen or methyl, wherein m is zero, and wherein n and q are not both zero.

4. A compound as claimed in claim 1, wherein R1 is a saturated aliphatic radical having 6 to 20 carbon atoms or an unsaturated aliphatic radical having one or two double bonds and 6 to 20 carbon atoms, G is phenylene, n is a number from 1 to 15, q is a number from 10 to 100, R and R5 are hydrogen or methyl and m is zero.

5. A compound as claimed in claim 1 wherein R1 is the radical of a fatty alcohol from a natural fat or oil or the radical of an alcohol from the oxo synthesis.

6. A process for the preparation of a compound as claimed in claim 1, which comprises condensing 2 moles of an amine of the general formula H-X
in which X is as defined in claim 1, with a bis-epoxide of the formula in which A and m are as defined in claim 1 at a tempe-rature from 80 to 200°C in the presence of an acid catalyst and reacting the condensation product with (m + 2)q moles of ethylene oxide, propylene oxide or both at 100 to 200°C in the presence of a basic catalyst, q being as defined in claim 1.

7, A process for reducing the surface tension of a liquid composition which comprises adding to said compo-sition an amount of a compound as claimed in claim 1 effective for reducing the surface tension.

8. A process for dispersing a solid in a liquid which comprises adding to said liquid an amount of a compound as claimed in claim 1 effective for dispersing said solid.

9. A process as claimed in claim 8, wherein the solid is a colorant.

10. A process as claimed in claim 9, wherein the colorant is a pigment.

11. A process as claimed in claim 9, wherein the liquid is an aqueous printing ink or emulsion paint.