阅读说明：本技术 作为润湿剂和分散剂的单环氧化物-单胺加合物 (Monoepoxide-monoamine adducts as wetting agents and dispersants ) 是由 M·贝塞尔 M·梅彻斯内尔 C·纳格尔 M·桑切斯和索萨 C·比耶克尔 P·斯坦恩 于 2018-03-28 设计创作，主要内容包括：本发明涉及可如下获得的环氧化物-胺加合物：通过一种或多种通式(I)的伯胺(A)与一种或多种通式(II)的单环氧化物(B)反应,其中Q是基团R<Sup>t</Sup>-[OEt]<Sub>n</Sub>[OPr]<Sub>m</Sub>[OBu]<Sub>s</Sub>-,其中R<Sup>t</Sup>是选自具有1至6个碳原子的烷基的基团,OEt是环氧乙烷基团,OPr是环氧丙烷基团且OBu是环氧丁烷基团,n是0至100的数,m是3至50的数且s是0至20的数且n+m+s＝3至170,R是选自具有4至24个碳原子的脂族基团、具有6至18个碳原子的芳族基团和具有7至34个碳原子的芳脂族基团的有机基团,且p是0或1,其中(i)使伯胺(A)和单环氧化物(B)以1:2至1:1.35的当量比(A):(B)反应；和(ii)至少40摩尔％的基团R选自具有6至18个碳原子的芳族基团和具有7至24个碳原子的芳脂族基团；和任选随后所述反应产物的成盐和/或季铵化和/或改性。本发明还涉及包含或由所述环氧化物-胺加合物构成的润湿剂和分散剂,还涉及所述润湿剂和分散剂的生产,涉及所述环氧化物-胺加合物和所述润湿剂和分散剂用于生产分散体的用途。本发明还涉及包含所述环氧化物-胺加合物和润湿剂和分散剂的分散体和颗粒配制剂。Q-NH<Sub>2</Sub>(I)；<Image he="182" wi="580" file="DDA0002299940780000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>。(The present invention relates to epoxide-amine adducts obtainable as follows: by reacting one or more primary amines (A) of the formula (I) with one or more monoepoxides (B) of the formula (II) in which Q is a radical R t ‑[OEt] n [OPr] m [OBu] s -, wherein R t Is a group selected from alkyl groups having from 1 to 6 carbon atoms, OEt is an ethylene oxide group, OPr is a propylene oxide group and OBu is a butylene oxide group, n is a number from 0 to 100, m is a number from 3 to 50 and s is a number from 0 to 20 and n + m + s ═ 3 to 170, R is a group selected from aliphatic groups having from 4 to 24 carbon atoms, aromatic groups having from 6 to 18 carbon atoms and araliphatic groups having from 7 to 34 carbon atomsAn organic group, and p is 0 or 1, wherein (i) a primary amine (a) and a monoepoxide (B) are reacted in an equivalent ratio of (a) to (B) of 1:2 to 1: 1.35; and (ii) at least 40 mol% of the radicals R are selected from aromatic radicals having 6 to 18 carbon atoms and araliphatic radicals having 7 to 24 carbon atoms; and optionally subsequent salification and/or quaternization and/or modification of the reaction product. The invention also relates to wetting agents and dispersants comprising or consisting of the epoxide-amine adduct, to the production of the wetting agents and dispersants, and to the use of the epoxide-amine adduct and the wetting agents and dispersants for producing dispersions. The invention also relates to dispersions and particle formulations comprising the epoxide-amine adduct and wetting and dispersing agents. Q-NH 2 (I)； 。)

1. Epoxide-amine adducts obtainable by

One or more primary amines (A) of the formula (I)

Q-NH₂(I)

With one or more monoepoxides (B) of the general formula (II)

Wherein

Q is a group R^t-[OEt]_n[OPr]_m[OBu]_s-, wherein

R^tIs a group selected from alkyl groups having 1 to 6 carbon atoms,

OEt is an ethylene oxide group, OPr is a propylene oxide group and OBu is a butylene oxide group,

n is a number from 0 to 100, m is a number from 3 to 50 and s is a number from 0 to 20 and n + m + s is from 3 to 170,

r is an organic radical selected from the group consisting of aliphatic radicals having from 4 to 24 carbon atoms, aromatic radicals having from 6 to 18 carbon atoms and araliphatic radicals having from 7 to 34 carbon atoms, and p is 0 or 1,

it is characterized in that

(i) Reacting a primary amine (A) and a monoepoxide (B) in an equivalent ratio of (A) to (B) of 1:2 to 1: 1.35; and

(ii) at least 40 mol% of the radicals R are selected from aromatic radicals having 6 to 18 carbon atoms and araliphatic radicals having 7 to 24 carbon atoms; and optionally subsequently

(a) Salt formation and/or quaternization of the nitrogen atom introduced into the reaction product of (a) and (B) via formula (I); and/or

(b) The reaction of hydroxyl groups formed by ring opening of the epoxide ring of formula (II) and/or NH groups formed by equimolar reaction of a species of formula (I) with a species of formula (II) with one or more species selected from the group consisting of lactones, hydroxycarboxylic acids, lactides, monoepoxide compounds and monoisocyanates.

2. The epoxide-amine adduct as claimed in claim 1, characterized in that it comprises one or more species of the general formula (III) as reaction product of (A) and (B)

Wherein

Q, R and p are as defined for formula (I), and

R¹is H or a group CH₂-CH(OH)-[CH₂-O]_p-R, provided that

At least 33 mol% of the radicals R¹Is CH₂-CH(OH)-[CH₂-O]_p‘-R, wherein p' is 0 or 1.

3. The epoxide-amine adduct of claim 2, characterized in that species (III) is present in the reaction product of (a) and (B) in an amount of at least 50% by weight based on the weight of the reaction product of (a) and (B).

4. The epoxide-amine adduct as claimed in one or more of claims 2 to 4, characterized in that the species of the formula (III) is converted completely or partially by salt formation into the species of the general formula (IVa)

Wherein

Q、R、R¹And p is as defined in formula (III), and

X^Θis an acid anion

And/or

Conversion, wholly or partially by quaternization, into species of formula (IVb)

Wherein

Q, R and p are as defined in formula (III),

R¹is CH₂-CH(OH)-[CH₂-O]_p‘-R, wherein p' is 0 or 1,

R²is an aliphatic group having 4 to 20 carbon atoms, an aromatic group having 6 to 14 carbon atoms or an araliphatic group having 7 to 30 carbon atoms, and

Y^Θis an anion selected from the group consisting of halide and sulfate or Y^ΘWith the radical R²Form a group R²-Y^ΘWherein R is²Is a group CH₂And Y is^ΘIs COO^Θ。

5. The epoxide-amine adduct as claimed in one or more of claims 1 to 4, characterized in that n is a number from 5 to 75, m is a number from 3 to 40 and s is a number from 0 to 10.

6. The epoxide-amine adduct as claimed in one or more of claims 1 to 5, characterized in that at least 40 mol% of the radicals R are selected from phenyl and cresyl groups.

7. The epoxide-amine adduct as claimed in one or more of claims 1 to 6, characterized in that the primary amine (A) and the monoepoxide (B) are reacted in an equivalence ratio (A) to (B) of 1:1.9 to 1: 1.5.

8. Wetting agents and dispersants comprising or consisting of one or more epoxide-amine adducts as claimed in claims 1 to 7.

9. A process for producing the wetting agent and the dispersant as claimed in claim 8, wherein

Reacting one or more primary amines (A) of the formula (I)

Q-NH₂(I)

With one or more monoepoxides (B) of the formula (II)

Wherein

Q is a group R^t-[OEt]_n[OPr]_m[OBu]_s-, wherein

R^tIs a group selected from alkyl groups having 1 to 6 carbon atoms,

OEt is an ethylene oxide group, OPr is a propylene oxide group and OBu is a butylene oxide group,

n is a number from 0 to 100, m is a number from 3 to 50 and s is a number from 0 to 20 and n + m + s is from 3 to 170,

r is an organic radical selected from the group consisting of aliphatic radicals having from 4 to 24 carbon atoms, aromatic radicals having from 6 to 18 carbon atoms and araliphatic radicals having from 7 to 34 carbon atoms, and p is 0 or 1,

it is characterized in that

(i) Reacting a primary amine (A) and a monoepoxide (B) in an equivalent ratio of (A) to (B) of 1:2 to 1: 1.35; and

(ii) at least 40 mol% of the radicals R are selected from aromatic radicals having 6 to 18 carbon atoms and araliphatic radicals having 7 to 24 carbon atoms; and the reaction product formed in the process is optionally wholly or partially

(a) Salification and/or quaternization by reacting the nitrogen atom introduced into the reaction product of (a) and (B) via formula (I) with an acid or a quaternizing agent; and/or

(b) The hydroxyl groups formed via ring opening of the epoxide ring of formula (II) and/or the NH groups formed by equimolar reaction of the species of formula (I) and the species of formula (II) are modified by reaction with one or more species selected from the group consisting of lactones, hydroxycarboxylic acids, lactides, monoepoxide compounds and monoisocyanates.

10. Use of the epoxide-amine adduct as claimed in any of claims 1 to 7, the wetting agent and dispersant as claimed in claim 8 and/or the wetting agent and dispersant obtainable by the process as claimed in claim 9 for producing a dispersion comprising a dispersion medium, at least one type of dispersed solid and the epoxide-amine adduct and/or the wetting agent and dispersant.

11. Use of the epoxide-amine adduct as claimed in any of claims 1 to 7, the wetting agent and the dispersant as claimed in claim 8 and/or the wetting agent and the dispersant obtainable by the process as claimed in claim 9 as emulsifier.

12. A dispersion comprising a dispersion medium, at least one type of dispersed particulate solid and at least one epoxide-amine adduct as claimed in any one of claims 1 to 7, a wetting agent and a dispersing agent as claimed in claim 8 or obtainable by the process as claimed in claim 9.

13. The dispersion as claimed in claim 12, wherein it is selected from the group consisting of inks, printing inks, coating compositions, lacquers, pigment pastes, filler pastes, pigment concentrates, ceramic materials, cosmetics, casting compounds, moulding compounds and polymer concrete compositions.

14. A dispersion as claimed in claim 12 or 13, wherein the total amount of epoxide-amine adduct as claimed in any one of claims 1 to 7, wetting agent and dispersing agent as claimed in claim 8 and wetting agent and dispersing agent obtainable by the process as claimed in claim 9 is from 0.1% to 10% by weight, based on the total weight of the dispersion.

15. A granule formulation comprising, based on the total weight of the granule formulation, from 5.0% to 99.9% by weight of one or more particulate solids and from 0.1% to 95.0% by weight in total of one or more epoxide-amine adducts, one or more wetting agents and dispersants as set forth in claim 8 and one or more wetting agents and dispersants obtainable by the process as set forth in claim 9.

Examples

Measuring method

Amine number

Amine Number (AN) is understood to mean the amount of KOH in mg corresponding to AN amine content of 1 g of substance. The amine number is determined by neutralization with 0.1N perchloric acid in acetic acid as titrant according to DIN 16945.

Addition of inert solvents such as cyclohexane, dioxane, chlorobenzene, acetone, methyl ethyl ketone can improve the titration of very weak bases.

Epoxy equivalent

Epoxy equivalent is understood to mean the amount of epoxy resin in grams which contains 16 grams of epoxy-bonded oxygen (epoxide oxygen).

Epoxy groups in epoxy resins can be determined by addition of HBr to the epoxide ring. By using HClO in the presence of cetyltrimethylammonium bromide (N, N, N-trimethyl-1-hexadecylammonium bromide; CTABr)₄The equivalent of HBr liberated was titrated.

Since the amine is also protonated simultaneously in the titration with perchloric acid, this amount of perchloric acid has to be subtracted to calculate the epoxy equivalent. The amine number must therefore be determined before the epoxy equivalent weight is determined.

Epoxy equivalent 1000/(consumption (ml) × n × f) - (amine value/56.1) by initial weight (gr.) }

n-normality of titrant

factor of titrant

Acid value

The acid number was determined by neutralization with 0.1N KOH in ethanol as titrant according to DIN EN ISO 2114.

R-COOH+KOH→R-COOK+H₂O

Comparative example

All adducts not according to the invention and pastes, paints and polymer concretes made using said adducts are indicated herein with an "x".

Epoxide-amine adduct EA1

82 g of Epikote 828(0.07 mol; undiluted difunctional bisphenol A-epichlorohydrin reaction product, manufacturer Momentive) were reacted with 528 g of Jeffamine M2070 (0.085 mol; a polyether monoamine with a terminal primary amino group, approx.10 OPr and 31 OEt units; amine number 27mg KOH/g; manufacturer Huntsman) at 140 ℃ for 27 hours.

Amine number 19.6mg KOH/g

Infinite epoxy equivalent weight

Epoxide-amine adduct EA2

82 g of Epikote 828(0.22 mol) were reacted with 359 g of Jeffamine M2070 (0.177 mol) and 8.6 g of dimethylaminopropylamine (0.08 mol) at 140 ℃ for 7 hours. Subsequently, 145 g of polyether-toluene diisocyanate adduct (preparation see below) was added and allowed to react for another 5 hours at 65 ℃.

Amine number 21.7mg KOH/g

Infinite epoxy equivalent weight

Isocyanate content 0.05%

Examples of the invention

Epoxide-amine adduct EA3

Cresyl glycidyl ether (1.042 moles) was reacted with Jeffamine M2070(0.573 moles, 10% excess NH) at 140 ℃ for 16 hours.

Amine number 23.99mg KOH/g

Infinite epoxy equivalent weight

Epoxide-amine adduct EA4

Cresyl glycidyl ether (1.042 moles) was reacted with Jeffamine M2005(0.573 moles, 10% excess NH) at 140 ℃ for 16 hours.

Amine number 22.54mg KOH/g

Infinite epoxy equivalent weight

Epoxide-amine adduct EA5

Cresyl glycidyl ether (1.042 moles) was reacted with surfaminine L200(0.546 moles, 5% excess NH) at 140 ℃ for 16 hours.

Amine number 24mg KOH/g

Infinite epoxy equivalent weight

Epoxide-amine adduct EA6

Cresyl glycidyl ether (2.83 moles) was reacted with 1462.30 grams of surfaminine L100 (1.486 moles, 5% excess NH) at 140 ℃ for 16 hours.

Amine number 60mg KOH/g

Infinite epoxy equivalent weight

Epoxide-amine adduct EA7

Cresyl glycidyl ether (0.75 mole) and Grilonit RV1814(0.762 mole) were reacted with Jeffamine eM2070(0.83 mole, 10% excess NH) at 140 ℃ for 16 h.

Amine number 22.9mg KOH/g

Infinite epoxy equivalent weight

Epoxide-amine adduct EA8

Vikolox 16(0.49 moles, C16 α -olefin oxide from Arkema) and cresyl glycidyl ether (0.75 moles) were reacted with Jeffamine M2070(0.68 moles) at 140 ℃ for 16 hours.

Amine number 22.9mg KOH/g

Infinite epoxy equivalent weight

Epoxide-amine adduct EA9 (salt formation)

49 g EA8(0.02 mol) was reacted with 2.35 g (0.02 mol) benzoic acid in 8 g Dowanol PMA at 50 ℃ for 1 hour.

Amine number 19.2mg KOH/g

Acid value 18.6mg KOH/g

SC:80％

Epoxide-amine adduct EA10 (quaternization of salt-forming adduct EA 9)

29.2 g EA9(0.01 mol) was reacted with 1.67 g (0.01 mol) cresyl glycidyl ether in 0.42 g Dowanol PMA at 120 ℃ for 4 h.

Amine number 18.4mg KOH/g

Acid value 17.0mg KOH/g

SC:80％

Epoxide-amine adduct EA11

1000 g of EA8(0.41 mol) were reacted with 46.8 g of benzyl chloride (0.37 mol) in 355 g of Dowanol PM and 355 g of Dowanol PMA at 120 ℃ for 4 hours.

Amine number 2.0mg KOH/g, residual content of benzyl chloride <500ppm (determined by HPLC)

SC:60％

Comparative example 1 not according to the invention

Comparative examples were made according to the instructions of International publication WO 2016059066A1 for Polymer 4.

Performance testing

The use of the polymers according to the invention as wetting agents and dispersants for the production of pigment concentrates and their use in paint systems.

Raw material

Production of pigment pastes and coating formulations

Pigment pastes PP were made according to the formulations in tables 1 to 4 below. The wetting and dispersing additives or Algene WF, Arkopal N100, Lansurf CO12 and MAKON TSP-25 (in the case of the reference pigment pastes), PEG 400, demineralized water and Preventol P91 MV were weighed into a beaker in this order and homogenized manually using a spatula. Subsequently, the respective amounts of pigment were incorporated in small amounts at a time in the Dispermat at about 500rpm (1.5m/s) using a gear wheel. Next, the batches were homogenized in a Dispermat at 3000rpm (9m/s) for 10 minutes. Thereafter, the pH was adjusted with sulfuric acid, the batch was completed with Rocima521 and transferred to a bead mill. The batch was then milled in a bead mill using SAZ-120-S beads (0.6-0.8mm) at 2800 + -50 rpm for 1 hour.

TABLE 1

TABLE 2

Pigment PB 15:0	PP2a*	PP2b*	PP2c	PP2d
					Algene WF	11.00
Lansurf CO12	7.90
					Comparative example 1		18.90
EA6			18.90
					EA3				18.90
Polyglykol P 400	6.00	6.00	6.00	6.00
					Softened water	31.30	31.30	31.30	31.30
Preventol P 91MV	0.14	0.14	0.14	0.14
					Hostaperm Blue A2R 15:0	43.0	43.0	43.0	43.0
H2SO4，25％	0.38	0.38	0.38	0.38
					Rocima 521	0.30	0.30	0.30	0.30
Sum of parts by weight	100.0	100.0	100.0	100.0

TABLE 3

TABLE 4

Pigment PO 34	PP4a*	PP4b	PP4c
				Algene WF	10.0
MAKON TSP-25	5.5
				EA3		15.50
EA11			15.50
				Polyglykol P 400	5.0	5.0	5.0
Softened water	40.97	40.97	40.97
				Preventol P 91MV	0.14	0.14	0.14
Permanent Orange RL 70	37.5	37.5	37.5
				H2SO4，25％	0.59	0.59	0.59
Rocima 521	0.30	0.30	0.30
				Sum of parts by weight	100.0	100.0	100.0

Further processable formulations of these slurries (pigment slurries: PP1b, PP1e, PP1f, PP2b and PP3b, PP3d, PP3 e) were not possible with the dispersant of comparative example 1, which is not according to the invention, since in these cases strong thickening or gelling of the slurry occurred after grinding was visible.

The resulting pigment slurry, which was in a processable range in terms of its viscosity, was mixed in a ratio of 3 parts by weight pigment slurry/97 parts by weight of Brilluxgloss Ename 275 (white, base 40). These slurries were stirred with a spatula and then homogenized for 3 minutes using a Skandex shaker (the composition of the coating formulation can be seen in table 5). The paint was applied to the control chart (contrast chart) using a 150 μm rod applicator and wiped (rub-out) in one position. The paint film is flashed off at 23 ℃ for 5 to 10 minutes. Immediately thereafter, a wiping test (rub-out test) was performed. The films were then cured at 23 ℃ for 24 hours and then the Δ L, Δ a, Δ b and Δ E values were determined.

TABLE 5

The Color intensity and the L, a, b and Δ E values were measured in each case on the white areas of the comparison plot with a Color Sphere Gloss instrument (available from BYKGardner). Color intensity was measured in% and Δ L, Δ a, Δ b and Δ E values were measured relative to the respective reference formulations containing wetting and dispersing additives from the prior art. In addition, Δ L, Δ a, Δ b, and Δ E values of the wipe (rub-out) were measured in comparison with the unloaded region.

The measurement results for each coating formulation can be derived from tables 6 to 9.

TABLE 6

TABLE 7

TABLE 8

TABLE 9

In summary, with regard to the use of the epoxide-amine adducts of the invention in pigment concentrates, it can be said that significantly higher color intensities are achieved than with the wetting and dispersing additives of the prior art. In formulations F1c, F1d, F2c and F2d, by using the additives of the invention, the blue hue is shifted as desired to a darker blue color (-b component) than in formulations F1a and F2a, respectively. The green formulation F3c appeared to be significantly greener (-a component) than the corresponding reference formulation F3a, and the orange formulations F4b and F4c exhibited significantly stronger red and yellow components (+ a and + b components) than the formulation F4a by using the epoxide-amine adduct of the present invention. The additives of the invention stabilize the colour paste excellently and achieve a significantly better E-value in the wiping (rub-out).

Manufacture and testing of Polymer concrete compositions

Raw material

1. Production of a Filler-containing unsaturated polyester resin (UP) for determining viscosity reduction

The UP resin and additives were initially loaded in a beaker having a diameter of 80mm and manually stirred with a spatula. The filler was then weighed into Millisil W10 and stirred with the same spatula. Thereafter, the compound was dispersed under the following conditions: 1 minute by means of a dissolver (40mm dissolving disc, peripheral speed 1.95m/s (930rpm)) and 2 additional minutes by means of a dissolver (40mm dissolving disc, peripheral speed 3.9m/s (1865 rpm)). The corresponding formulations are listed in table 10.

After dispersion, the samples were filled into aluminum cups and stored in a water bath at 30 ℃ for 30 minutes. The viscosity in pascal seconds is measured using a Brookfield DV II + rotational viscometer (spindle 6, shear rate 20rpm) at 30 ℃. The viscosity and the percentage reduction in viscosity compared to UP1 are listed in table 10.

Watch 10

Formulation	UP1*	UP2*	UP3*	UP4	UP5	UP6
							Palatal P4-01	30.00	29.30	29.30	29.30	29.30	29.30
BYK-W 908	-	0.70	-	-	-	-
							BYK-W 909	-	-	0.70	-	-	-
EA3	-	-	-	0.70	-	-
							EA4	-	-	-	-	0.70
EA7						0.70
							Millisil W 10	70.00	70.00	70.00	70.00	70.00	70.00
Sum of parts by weight	100.00	100.00	100.00	100.00	100.00	100.00
							Viscosity [ Pa.s ]]	80.8	51.8	58.4	37.6	46.0	36.2
Viscosity reduction [% ]]		35.9	27.7	53.5	43.1	55.2

1% additive based on filler

The formulations UP4, UP5 and UP6 of the invention containing the epoxide-amine adduct according to the invention are able to reduce the viscosity of the formulations considerably more than the customary wetting and dispersing agents of the prior art. This is particularly pronounced in the case of UP4 and UP6 using formulations EA3 and EA 7. In EA3 and EA7, n > m (EtO: PrO ═ 31:10), while for EA4, m > n (EtO: PrO ═ 6: 29).

This test is a preliminary test in the manufacture of polymer concrete. It was used to determine the effect of additives on viscosity reduction. For this purpose, neither a coupling agent (BYK C8000) nor catalysis was initially used. Furthermore, the addition of crude silicate was omitted for viscosity measurement.

2. Manufacture of polymer concrete compositions

UP resin (Palatal P4-01), coupling agent (tackifier) (BYK C8000), co-promoter (Akzo NL-51P) and free radical initiator (Trigonox C) were initially loaded in a beaker. The amounts are shown in table 11. Subsequently, wetting and dispersing additives and pigments were added and manually stirred. Thereafter, the quartz mixture and quartz powder were added and stirred manually. The compound was then homogenized in a Speed Mixer DAC 400.1FVZ at 1650rpm for 10 seconds.

3. Manufacture of Polymer Concrete Tiles (PCT)

A square metal spacer (approximately 6mm thick, 20cm side length) was lined with PE film and a sample of the polymer concrete composition was laid in the metal spacer. The filled metal spacer frame was covered with a PE film before pressing to avoid contamination of the press. Subsequently, the specimens thus prepared were pressed at 50 bar (about 250N/cm) using a Polystat 200T press²) And pressing at 90 ℃ for 5 minutes. The pressed composition was then removed from the spacer frame and placed on a glass plate that had been pretreated with a release wax. The final curing of the polymer concrete tiles was carried out in an air circulation drying oven at 80 ℃ for 1 hour. The polymer concrete compositions are listed in table 11.

The surface properties of the cured polymer concrete tiles were then evaluated according to the school-grade system from 1 to 6. In this case, 1 represents a smooth dense surface without deep holes and with good leveling. Such samples have desirable properties such as high strength, low air inclusions and a premium appearance. 6 represents a rough surface with a very uneven porous appearance and indicating poor compaction. Such samples exhibit lower strength with deep defects or chipping. The ratings are given in table 11. When using the epoxide-amine adducts of the present invention (EA3, EA4 and EA7), it is possible to detect greatly improved surface quality.

TABLE 11

The formulations of the invention PCT4, PCT5 and PCT6, which contain the epoxide-amine adducts according to the invention, provide outstanding surface quality compared to the conventional wetting and dispersing agents of the prior art. This is particularly pronounced in the case of UP4 and UP6 using formulations EA3 and EA 7. In EA3 and EA7, n > m (EtO: PrO ═ 31:10), while for EA4, m > n (EtO: PrO ═ 6: 29).