CA1158384A

CA1158384A - Dispersing agents, process for their manufacture and their use

Info

Publication number: CA1158384A
Application number: CA000348961A
Authority: CA
Inventors: Helmut Diery; Volker Hemmerling
Original assignee: Hoechst AG
Current assignee: Hoechst AG
Priority date: 1979-04-02
Filing date: 1980-04-01
Publication date: 1983-12-06
Also published as: DE3063254D1; JPS6326742B2; BR8002008A; DE2913176A1; DK140680A; JPS55133337A; DK160101B; EP0017189A1; EP0017189B1; ES489963A1; AR230832A1; AU533637B2; DK160101C; AU5702180A

Abstract

ABSTRACT OF THE DISCLOSURE
A dispersion of a pigment, a dyestuff, an optical brightener, a plant protecting agent or a pest-combating agent, containing as dispersing agent a compound of the formula (1) in which Y is a group of the formula or R1 denotes linear or branched C1-C24-alkyl, C2-C4-alkenyl or C1-C24alkoxypropyl, A denotes linear or branched C2-C4alkylene, Z1 and Z2, which are identical or different, denote radicals of the formula

Description

3~4 The present invention provides a dispersion of a pigment, a dyestuff, an optical brightener, a plant protecting agent or a pest-combating agent, containing as dispersing agent a compound of the formula Y-CH2IH-cH20 ~ I ~ Oz ~ I oz (1) in which Y is a group of the formula _ N R or - N'' \ z2 ~ A - OZ , R denotes linear or branched Cl-C24alkyl, Cl-C24al~enyl or Cl-C24-alkoxypropyl, A denotes linear or branched C2-C4alkylene, zl and z2, which are identical or different, denote radicals of the formula -(CH2CHO)xH in which R2 is hydrogen, methyl or ethyl and x is an integer of up to about 150, R3 and R4 denote hydrogen or Cl-C4alkyl and m is zero or an integer from 1 to 12.
The above compound is prepared by known rnethocls by first reacting a compound of the formula 2 CH2 CH-CH2-0 ~ C ~ OH ~ C ~ 2 \ 2 with an amine of the formula 3 or 4 Rl A - OH
- HN (3) - HN~' (4) EI ~ A ~ OH
to give a compound of the forrnula 5

2-.

~ ~5838~

- 3 - _E 79/F 08?

Y CH2 CHCH2 O[ ~ C~ ~ ~28-~C~l2O}m ~ C ~ ~CH2-CH-CH2 yl (5) in which Y' denotes a group of the formula -N or -N \
H AOH
and oxalkylating the compound obtained.
Suitable starting compounds of the formula 2 are the known epoxide resins as far as they contain terminal glycidyl ether groups and obtained by reacting p,p'-dihy-droxydiphenylmethane~ p~p'-dihydro~ydiphenylpropane, p,p'-dihydroxydiphenylbutane with epichlorohydrin in known manner. Higher epoxide resins as obtained, for example, by reaction of one of the aforesaid bisphenols with less than stoichiometric amounts of epichlorohydrin can also be used.
The epoxides are reacted with the amines of the formula 3 in an inert organic solvent, such as methanol or chlorobenzene, at temperatures of about 60C to 120C. It is likewise possible to earry out the reaction in the absence Or a solvent by adding the epoxide to the amine at temperatures of about 100 to 150C.
Suitable primary C1-C24allcylamines of the formula 3 are, for example, methylamine, n- or i-butylamine, n-hexyl-amine, n-octylamine, 2-ethylhexylamine, i-nonylamine, n-de-cylamine, n-dodecylamine, coconut fatty ami.ne, isotridecyl-amine, n-hexadecylamine, n-octadecylamine, tallow fatty amine, oleylamine, eicosylamine, cocosylamine, 3 butoxypro--pylamine, 3-isononyloxypropylamine, 3-n-hexadecyloxypropyl-amine, as well as dialkanol amlnes such as diethanol amine, di-isopropanol amine and di-isobutanol amine.
The aforesai.d reaction first gives the product of the formula 5 which is then oxalkylated according to known me-~ ~5~3~

thods with potassium hydroxide or preferably with sodium hydroxideor sodium methylate as catalyst at temperatures of about 160 to 200C.
The oxalkylation can be carried out with ethylene oxide whereby products containing polyethylene oxide chains are formed.
~lternati~ely~ ~irst the product can be oxalkylated with propylene oxide to build up a polypropylene chain, whereupon the oxalkylation is continued with ethylene oxide to obtain a water-soluble product and to introduce a polyethylene oxide chain. The compounds of formula (1) can be obtained not only by bloc~ polymerization in which first propylene oxide and then ethylene oxide or vice versa are introduced, but also by a mixed oxalkylation with a mixture of ethylene oxide and propylene oxide. The oxalkyla-tion can be carried out at atmospheric pressure or in an autoclave preferably under a working pressure of 2 to 8 bars with a supply of gaseous or liquid ethylene oxide. The amount of ethylene oxide, especially the lower limit of x should be such that the compounds obtained are soluble in water.
The compounds of the formula 1 prepared in this manner are excellently suitable as dispersing agents for the manufacture of dispersions of pigments/ dyestuffs and optical brighteners, and or the formulation of plant protecting agents and pest combating agents.
The compounds of formula (L) can be used in the formula-tions either alone or in combination with other surEace-active compounds, additives and auxiliaries. The anhydrous dispersing agents of the invention can be diluted in any desired proportion with water or water/alcohol mixtures and, therefore, they are especially suitable for the manufacture of highly concentrated,

4--3~1 flowable dispersions of organic and inorganic pigments.
The pigment dispersions of -the invention are prepared in known manner by dispersing the pigments, for example azo pigme~ts, laked azo pigments, triphenylmethane pigments, thioindigo pigments, perylene tetracarboxylic acid pigments, dioxazine pigments, quinacridone pigments, phthalocyanine pigments, or inorganic pig-ments, with the compounds of formula (1) and with addition of ethylene glycol, wa-ter and optionally small amounts of other dis~
persing agents in a suitable dispersing device, for example an agitator mill or a divided trough kneader. In the case of a kneader the dispersing agent and a small amount of water are first introduced whereupon the pigments are added in portions, optionally with the addition of small amounts of other dispersing agents and the whole is kneaded to give a paste o~ tough consistency. As soon as the desired fineness is obtained, the mixture is diluted to the desired color strength and consistency by adding, for example, ethylene glycol and water. With the use of an agitator mill a homogeneous paste is first prepared by stirring a mixture of the pigments, the dispersing agents of the invention, ethylene glycol and water, optionally with addition of small amounts of other dispersing agents. The suspension obtained which is capable o~
being pumped is then milled, normally in a continuous agitator mill, with quartzite beads of a diameter of about 1 mm, optionally with several passages until the desired fineness is reached. The desired color strength can then be adjusted by adding water or~
for example, ethylene glycol as water retention agent. The pro-portion of dispersing agent to pigment powder can vary within wide limits, in general it is in the range o from 0.1 to 0.2 part by

-5-3~
weight of dispersing agent for one part by welght of dry pigment powder.
The pigment dispersions of the invention obtained in this manner can be used for coloring disperse dyes for inside and outside paints, in the field of textile pigment printing or in aqueous flexographic printing inks or gravure printing inks, especially in combination with the addition of alcohols. The dispersing agents of the invention have excellent wet-ting and dispersing properties and, therefore r they can be used in relatively small amounts, relative to the pigment content of the dispersions. In flexographic printing and gravure printing light and brilliant shades are not affected by the wea~ inherent coloration of the dispersing agents of the invention.
The following examples illustra~e the formation of compounds o~ formula (l). In manufacturing examples L to 12 "ti-" means in all cases 'linternal temperature".
E X A M P L E
268 g of distilled tallow fatty amine (composition 16 18' % Cl8, 4 ~ Cl2/C14; basic N 5.21 %, measured mol 268) and 500 ml of methanol are introduced into a four-necked graduated flask with ground glass stopper provided wi-th reflux condenser, internal thermometer, stirrer and dropping funnel. At ti = 45C, 189 g of a commercial diglycidyl ether of 2,2-bis[p-hydroxyphenyl]-propane (epoxide number 193, measured mol 378) are added. The reaction mixture is stirred for 4 hours at ti = 65C
and the methanol is distilled ~ff i~ a rotary evaporator. The reaction product is a yellowish solid paste ~ith a content of basic nitrogen of 3.10/3.11 and a measured mol of 902.

~ -6-~ ~5~3~

225.2 g of the addition product obtained are oxethylated with 228 g of ethylene oxide a~ 180C for 17 hours in the presence of 2 g of pulverized caustic soda. The liquid product obtained has a cloud point of 57C (in water according to DIN 53,917) and contains 20.6 mols of ethylene oxide, relative to 1 mol.
The addition product of tallow fatty amine and diglycidyl ether can also be prepared in the melt. In this case the tallow fatty amine is heated to ti = 150C, whereupon the diglycidyl ether heated to 50C is added dropwise at said temperature over a period of about 1 hour and stirring of the mixture is continued for 90 minutes.
E X A M P L E _2:
In the manner described in E~ample 1, 105 g of propylene oxide are added dropwise over a period of 15 hours at 170 to 190C
and in the presence of 0.5 g of pulverized -6a-1 ~583~
- 7 ~ HOE 79/F 082 caustic sod~ to ~0.2 g (0.1 mol) of the addition product of 2 mols of tallow fatty aMine and 1 mol of the diglyci-dyl ether of 2,2-bis/p-hydroxyphenyl7 propane. The poly-oxypropylate obtained is a brown liquid of medium vis-cosity containing 18.8 mols of propylene oxide units permol, which is further reacted with ethylene oxide. Af-ter addition of 1 g of pu]verized caustic soda, 72 g of ethylene oxide are added dur~ng the course of 7 hours at ti - 180C. The brown liquid of medium viscosity has a cloud point of 38C ~in waker) and of 79C ~in butyl digly-col) according to DIN 53,917.

2.2 g of pulverized caustic soda are added to 419 g (0.46 msl) of an addition product prepared as described in Example 1 from 2 mols of distilled tallow fatty amine and the diglycidyl ether of 2,2-bis/p~hydroxyphenyl7~propane The oxethylation is carried out with 451 g of ethylene oxi-de at 140 to 160C under pressure and for 4 hours. The li-quid reaction product has a cloud point of 61.3C in waterand contains 22.3 mols of ethylene oxide per mol.

370 g (2 mols) of distilled dodecylamine with 98 % of C12alkyl (basic nitrogen 7.53/7.55 %) are dissolved in 1,000 ml of methanol and a~ ti = 45C 378 g of a diglycidyl ether of 2,2-bis/p-hydroxyphenyl / propane (epoxide number 193, measured mol 378) are added over a period of 15 minutes.
The mixture is stirred for 4 hours at 65C whereupon the methanol is distilled off. The light reaction product so--lidifies on cooling to a waxy solid mass (basic nitrogen 3.70/3.69, measur-ed mol 758).
303.2 g (0.4 mol) of the reaction product are reacted at ti : 180C over a period of 22 hours and in the presence of 1.5 g of` pulverized caustic soda with 443 g of propylene oxide. A further 1.5 g of pulverized caustic soda are ad-ded after about one half of the reaction time.

3~L

g3.3 g of the oxpropylated compound are oxethylated at 180 to 190C by introducing 88 g of ethylene oxide to give a liquid, water soluble product having a cloud po~nt of` 78C in butyl diglycol according to DIN 53,917.

E X A M P 1. E 4a:
93.3 g of the oxpropylated compound of Example ~ are reacted in analogous manner with 173.5 g of ethylene oxide.
In this case a paste which is soluble in water to give a clear solution and which has a cloud point of 93C in bu-tyl diglycol according to DIN 53,917 is obtained.

E X A M P L E 5:
When, instead of the dodecylamine of Example 4, coco-nut fatty amine (basic nitrogen 7.08/7.11 %) is used, a di-addition product on the diglycidyl ether of 2,2-bis/p-hy droxyphenyl7-propane is obtained in the form of a waxy mass with a basic nitrogen content of 3.54/3.56 % and a measured mol of 789. 315.6 g of this compound are oxpropylated with 441 ~ of propylene oxide at 180 to 200C in the presence of 1 g of pulverized caustic soda. A liquid of medium visco-sity is obtained. 378.4 g of the oxpropylated compound are reacted at 190C and in the presence of caustic soda with 375 g of ethylene oxide. The dispersing agent obtained gives a clear solution in water and has a cloud point of 78.0C in water and of 90.0C in butyl diglycol according to DIN 53,g17.
The addition compound of coconut fatty amine and the diglycidyl ether can also be produced in the absence of a solvent. To this end 788 g of distilled coconut fatty % f ~12~ 19 % f 514~ 13 % of Cg/C10, 17 % of C16/C18) are heated to 120C and 740 g of the diglycidyl ether ar-e added dropwise within 20 minutes while cooling with ice, whereby the temperature rises to 150C. Stirrin~
of the reaction mixture is continued for 1 hour at 120C.

E X A M P L E 6:
The addition product of 2 mols of diethanolamine on l mol of diglycidyl ether of 2,2-bis/p-hydroxyphenyl7-propa-ne, prepared by adding the diglycidyl ether to the di.etha-nolamir.e at ti. = 120C over a period of 30 minutes and withstirring of the mixture for 2 hours at 140C, is oxalkylat-ed. For this purpose 1,033 g of propylene oxi.de are added at ti = 190 to 205C in the presence o~ 2 g of pulverized caustic soda and under nitrogen on 127.2 g (0.2 measured mol) of the compound obtained. Next, 318 g of ethylene oxide are added on 174.0 g of the oxpropylated compound.
The final product is a water-soluble paste having a cloud point of 87.5C in water and of 94.5C in butyl dig'ycol.

E X A M P L E_ 7:
25~ g (2 mols) of 2-ethylhexylamine are heated to ti. -90C whereupon 370 g (1 mol) of diglycidyl ether of 2,2-bis-/p-hydroxyphenyl7-propane are added within 20 minutes whereby the temperature of the reaction mixture rises to ti = 100C. Stirring of the mixture is continued for 90 minutes at ti = 110C. Measured mol 634.
253.6 g of the addition compound are reacted in the presence of 2 g of pulverized caustic soda and at 190 to 2t0C with 597 g of propylene oxide. The compound obtained contains 26.2 mols of propylene oxide per mol.
212.6 g of the propylene oxide reaction product are then reacted at 180 to 195C with 345 g of ethylene oxide whereupon a water-soluble surface acti.ve compound is ob-tained having a cloud point of 90.5C in butyl and of 83.5C in waker.

E X A M P L E 8:
-An addition product is prepared from 2 mols of ~-methyl-ethanolamine and 1 mol of diglycidyl ether of 2,2-bis/p_hy_ droxypheny~7-propane by adding the diglycidyl ether to the amine at 130 to 150C and stirring the rnixture for 2 hours at 1~0C. The product is an a~lber-colored transparent ~ ~ ~83~

resin. 2~0 g (0.5 mol) thereof are reacted with 1,678 g Or propylene oxide in the presence of 2 g of pulverized caustic soda at 190 to 195C. 387.6 g of the reaction product are then reacted at 190C with 674 g of ethylene oxide. The solidified waxy, water-soluble product obtained has a cloud point, of 88.0C i.n water and of 90.5C in butyl diglycol.

254.6 g (1 mol) of a distilled tallow fatty amine are dissolved in 500 ml of chlorobenzene and a solution of 936 g (0.5 mol) of a compound of the formula t5 CH - CH
CH2-&H~CH2-0 ~ 1~'3CH2C~EICfl2 - ~,3-C~oCH2C~-&H2 m= 5-6 in 1424 g chlorobenzene is added over a period of about 10 minutes at 45C and stirring of the reaction mixture is continued for 3 1/2 hours at 70C. After distillation of the chlorobenzene, a brittle resin is obtained having a content of basic nitrogen of 1.13 %.
1.5 g of pulverized caustic soda are added to 476.4 g (0.2 mol) of the reaction product obtained which is then reacted with 326 g of propylene oxide at 170 to 190C. A
clear viscous product is obtained. 200.5 g thereof (0.05 mol) are further reacted with 146 g of ethylene oxide. The water-soluble product obtained having a medium viscosity has a cloud poi.nt of 30.4C in water.

E X A M P L E 10:
In the manner described in Example 9, 204 g (0.8 mol) of a distilled tallow fatty amine are reacted in chloroben-zene as solvent with 1,168 g (0.4 mol) of a condensed ep-oxide resi.n of the formula 2 with R3 and R4 being CH3 and IL ~5838~
~ HOE 79/F 082 m being 12. A resinous, britt1.e solid is obtained. 686 g (0.2 mol) thereof are reacted with 672 g (12 rnols) of pro-pylene oxide in the presence of 1 g of pulverized caustic soda and at 180 to 210C. 339.5 g (0.05 mol) of the vis-cous compound obtained are reacted with 246 g of ethylene oxide in the presence of 0.5 g of pulverized causti.c soda and at 190 to 200C. The reaction product is soluble in water and has a cloud point of 36.9C in water and of 68.5C in butyl diglycol according to DIN 53,917.

E X A M P L E 11:
522 g (2 mols) of distilled tallow fatty amine are heated to ti - 150C whereupon 936 g (1 mol) of an epoxide resin of the formula 2 with R3 and R4 being CH3 and m being 2.4 are added at 145 to 155C over a period of about 90 minutes. Stirring of the reaction mixture is continued for 1 hour at 150C. 291.6 g (0.2 mol) of the resin obtained are mixed with 1 g of pulverized caustic soda and reacted with 428 g of propylene oxide at 180 to 220C.
360 g (0.1 mol) of the oxpropylated compound are then oxethylated at 190 to 195C with 280 g of ethylene oxide.
~he water-soluble reaction product obtained has a cloud point of 34C in water and of 72.0C in butyl diglycol according to DIN 53,917.
E X A _P L E 12:
510 g (2 mols) of distilled tallow fatty amine (compo-sition as indicated in Example 1) are dissolved in 100 ml of methanol. At ti - 45C 352 g (1 mol) of diglycidyl ether of bis-/p-hydroxyphenyl7methane (epoxide number 207/208) are added, the mixture is stirred for 4 hours at 65C, whereupon the methanol is evaporated. Th.e reaction product solidifies to a waxy mass.
305.2 g of the reacti.on product obtained are reacted with 323 g of ethylene oxide at 190C and in the presence of 2 g of caustic soda. The water-soluble reacti.on product formed has a cloud point of 60.4C in water and of 86.5C

in bu~,yl diglycol according to DIN 53,917~
The oxalkylation products of Examples 1 to 12 are sum-- mari~ed in the following table in which EO stands for ethy-lene oxide, PO for propylene oxide and BDG means butyl di 5 glycol. `

~ ~ 5 ~ 3 A 0 ~ ~ -C- < ~ -OC~2CH-CH2C~ m _ Z1 A= -CH2-C-CH2N-R1, z1~ z2= -(CH2CH0)xH, R2= H or CH3 0 z2 ~2 Com- ~1 R3 R4 m mol alkylene cloud point pound oxide per mol according to of final DIN 53917 product No. ~ z1 ~ z2 _ _ . ~ __~ ___ _ 1 tallow ~atty -CH3-CH3 E0 20.6 57C (in H20) 2 tallow fatty -CH -CH~ 0 P0 18.8 38C (in H,O) alkyl 3 ~ E0 35.6 79C (in BDG) 3 tallow ~atty -CH3-CH3 0 E0 22.3 61,3C (in H20) 4 d~decyl -CH3-C~3 P0 19.8 78C (in BDG) E0 40.0 4a dodecyl --CH3CH3 P 19.8 93C (in BDG) EO 7~.8 alkyl -CH3-CH3 P 19.7 78,0 C (in H20) E0 42.6 90.0C (in BDG)

6 z2 -CH3-CH3 0 P0 92.2 94.5C (in ~DG) , E0 240 87.5C (in H20)

7 2-ethyl-h~xyl -CH3-C~3 P0 26.6 90.5C ( in BDG) E0 78.4 83.5 C (in H20)

8 -CH3 -CH3-CH3 P 60 88C (in H20) E0 153.2 90.5 C (in BDG)

9 tallow fatty -CH3-CH3 5-6 P0 29.1 30.4 C (in H20) ~].lcyl ~0 66.LI
tallow fatty -~H3-CH3 ^~12 P0 60 36.9C (in H20) ~lkyl EO 112 68.5C (in BDG) 11 tallow ~atty -CH3-CH3 ~ 2-4 P0 38.2 34 C ~in H20) ~ C~r . E0 63.6 72.0C (in BDG) 12 tallow fatty H H 0 E0 21 60.4C (in H20) ~lkyl 86.5OC (in BDG) 1 ~5~38~
_ 14 _ _OE 79!F 082 EXAMPLES OF liP}'L~.CATION
E "~ A M P L E
288 parts by weight of PigMent Red 14 (Colour Index Num-ber 12,380), 54 parts by weight of the compound of Example 2 and about 80 parts by weight of water are Icneaded for ap~
proximately 30 minutes in a divided trough kneader to give a tough paste. When the desired fineness is reached, the paste is diluted by adding 118 parts by weight of water and 60 parts by weight of ethylene glycol. The dispersion having a pigment content of 48 % by weight is thinly li-quid and stable to storage. It is excellently suitable for coloring aqueous paints and for use in aqueous flexo-graphic printing inks and gravure printing inks.

_ X A M P L E II:_ Instead of the compound of Example 2, 72 parts by weight of the compound of Example 6 are used. The pigment preparation obtained has the same good utilitarian proper~
ties.
~0 E X Q M P L E III:
Instead of the compound of Example 2, 72 parts by weight of the compound of Example 9 are used. The pig-ment preparation obtained has the same good utilitarian properties.

E X A M P L E IV:
Instead of the compound of Example 2 9 78 parts by weight of the compound of Example 11 are used. The pigment prepa-ration obtai.ned has the same good utilitarian properties.

E X A M P L E__V:
90 parts by weight of a copper phthalocyanine pigment(Pigment Blue 15, Colour Index Number 74,160), 20 parts of the compound of Example 4a and 70 parts by weight of water are milled for about 1 hollr in a 1 liter agitator mill with the addition of about '100 parts by weight of quartzite beads 33~1 ~ 15 - HOE 79~F_082 (1 to 2 mm in diameter) as milling bodies. Af~er milling, 20 parts by weight of ethylene glycol are added to the mil-led material and the thinly liquid dispersion containing 45 % b~J ~eight of pigment is separated from the milling bo--dies over a sieve. The dispersion is excellently suitablefor use ir. aqueous flexographic and gravure pr~nting inks.

E X A M P L E VI:
__ A pigment dispersion having equally good properties is obtained when in Example V the compound of Example 4a is replaced by 24 parts by weight of the compound of Example 5.

E X A M P L E VII-A pigment dispersion having equally good properties is obtained when in Example V the compound of Example l~a is re placed by 28 parts by weight of the compound of Example 8.

E X A M P L E VIII:
250 parts by weight of a pigment obtained by mixed coupling of diazotized 3,3'-dichlorobenzidine on acetani-lide and acetic acid p-anisidide in a proportion of 9:1, 50 parts by weight of the compound of Example 1 and about 65 parts by weight of water are kneaded for about 2 hours in a divided trough kneader to give a tough paste. When the desired fineness is reached, the dispersion is diluted to a pigment content of 50 ~ with 50 parts by weight of ethylene glycol and 135 parts by weight of water. The thin--ly liquid pi.gment dispersion obtained can be diluted in any desired ratio with water and water--containing binder sy-stems.

E X A M P L E IX:
When usi.ng in Example VIII, instead of the compound of Example 1, 60 parts by weight of the compound of Example 7, a pigment dispersion with equally good utilitarian proper-ties is obtained.

3~
- 16 - HOE 79/F 08?

E X A M P 1. ~ X:
By using in ~xample VIII, instead of the compound of Example 1, 60 parts by weight, of the compound of Example

10, a pigment dispersion having equally good properties is obtained.

E X A M P L E_ XI:
90 parts by weight of Pigment Red 147 (Colour Index Number 12,433), 20 parts by weight of the compound of Ex-ample 3 and about 30 parts by weight of water are knead-ed for about 30 minutes in a di~ided trough kneader to give a tough paste. After kneading the paste is diluted with 80 parts by weight of water and 20 parts by weight of ethylene glycol. The dispersion containing 45 parts by weight of pigment is flowable and excellently suitable for use in aqueous flexographic printing lnks.

E X A M P L E XII:
By using in Example XI, instead of the compound of Ex-ample 3, 20 parts by weight of the compound of Example 12,a pigment dispersion having equally good properties is ob-tained.

Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A dispersion of a pigment, a dyestuff, an optical brightener, a plant protecting agent or a pest-combating agent, containing as dispersing agent a compound of the formula (1) in which Y is a group of the formula or , R1 denotes linear or branched C1-C24alkyl, C1-C24alkeryl or C1-C24alkoxypropyl, A denotes linear or branched C2-C4alkylene, Z1 and Z2, which are identical or different, denote radicals of the formula in which R2 is hydrogen, methyl or ethyl and x is an integer of up to about 150, R3 and R4 denote hydro-gen or C1-C4alkyl and m is zero or an integer from 1 to 12.

2. A dispersion according to claim 1 wherein in the compound of formula (1) Y is a group of the formula in which R1 is a C12-C18alkyl or C12-C18alkenyl group, Z2 is as defined in claim 1 and R3 and R4 are both methyl groups.