Monoepoxide-monoamine adducts as wetting agents and dispersants

Abstract

The invention relates to epoxide-amine adducts obtainable by reaction of one or more primary amines (A) of general formula (I)
Q-NH.sub.2  (I)
with one or more monoepoxides (B) of general formula (II) ##STR00001##
wherein Q is a radical R.sup.t-[OEt].sub.n[OPr].sub.m[OBu].sub.s-, in which R.sup.t is a radical selected from alkyl radicals having 1 to 6 carbon atoms, OEt is an ethylene oxide radical, OPr is a propylene oxide radical and OBu is a butylene oxide radical, 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 an organic radical selected from aliphatic radicals having 4 to 24 carbon atoms, aromatic radicals having 6 to 18 carbon atoms and araliphatic radicals having 7 to 34 carbon atoms, and p is 0 or 1, wherein (i) the primary amine(s) (A) and the monoepoxide(s) (B) are reacted in an equivalents ratio (A):(B) of from 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 furthermore relates to wetting agents and dispersants comprising or consisting of the epoxide-amine adducts and also to the production of the wetting agents and dispersants and to the use of the epoxide-amine adducts and the wetting agents and dispersants for the production of dispersions. The invention also relates to dispersions and particle formulations comprising the epoxide-amine adducts and wetting agents and dispersants.

Claims

1. A dispersion, the dispersion being an ink or a coating composition and comprising a dispersion medium, at least one kind of a dispersed pigment and at least one epoxide-amine product obtained by reaction of one or more primary amines (A) of general formula (I)
Q-NH.sub.2  (I) with one or more monoepoxides (B) of general formula (II) ##STR00009## wherein Q is a radical R.sup.t-[OEt].sub.n[OPr].sub.m[OBu].sub.s-, in which R.sup.t is a radical selected from alkyl radicals having 1 to 6 carbon atoms, OEt is an ethylene oxide radical, OPr is a propylene oxide radical and OBu is a butylene oxide radical, n is a number from 5 to 75, m is a number from 3 to 40, s is a number from 0 to 10,and n+m+s=8 to 125, R is an organic radical selected from aliphatic radicals having 4 to 24 carbon atoms, aromatic radicals having 7 to 18 carbon atoms and araliphatic radicals having 7 to 34 carbon atoms, and p is 0 or 1, wherein (i) the one or more primary amines (A) and the one or more monoepoxides (B) are reacted in an equivalents ratio (A):(B) of from 1:2 to 1:1.35; and (ii) at least 40 mol % of the radicals R are selected from aromatic radicals having 7 to 18 carbon atoms and araliphatic radicals having 7 to 24 carbon atoms.

2. The dispersion as claimed in claim 1, wherein the at least one epoxide-amine product comprises one or more species of general formula (III) ##STR00010## as reaction product of (A) and (B), wherein Q is defined in formula (I), R and p are defined in formula (II), and R.sup.1 is H or a radical CH.sub.2—CH(OH)—[CH.sub.2—O].sub.p—R, with the proviso that at least 33 mol % of the radicals R.sup.1 is CH.sub.2—CH(OH)—[CH.sub.2—O].sub.p′—R, in which p′=0 or 1.

3. The dispersion as claimed in claim 2, wherein the one or more species of general formula (III) are 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 dispersion as claimed in claim 2, wherein the one or more species of general formula (III) are at least partially converted by salification into one or more species of general formula (Na) ##STR00011## wherein Q is defined in formula (I), R and p are defined in formula (II), R.sup.1 is defined in formula (III), and X⊖ is an acid anion and/or are fully or partially converted by quaternization into one or more species of formula (IVb) ##STR00012## wherein Q is defined in formula (I), R and p are defined in formula (II), R.sup.1 is CH.sub.2—CH(OH)—[CH.sub.2—O].sub.p′—R, in which p′=0 or 1, R.sup.2 is an aliphatic radical having 4 to 20 carbon atoms, an aromatic radical having 7 to 14 carbon atoms or araliphatic radical having 7 to 30 carbon atoms, and Y.sup.⊖ is an anion selected from the group consisting of halides and sulfate or Y.sup.⊖ forms with the radical R.sup.2 a radical R.sup.2—Y.sup.⊖ in which R.sup.2 is a radical CH.sub.2 and Y.sup.⊖ is COO⊖.

5. The dispersion as claimed in claim 1, wherein at least 40 mol % of the radicals R include cresyl.

6. The dispersion as claimed in claim 1, wherein the one or more primary amines (A) and the one or more monoepoxides (B) are reacted in an equivalents ratio (A):(B) of from 1:1.9 to 1:1.5.

7. The dispersion as claimed in claim 1, wherein the total amount of the at least one epoxide-amine product, based on the total weight of the dispersion, is 0.1% to 10% by weight.

8. The dispersion as claimed in claim 1, the at least one epoxide-amine product being a further product of: (a) salification and/or quaternization of the nitrogen atom introduced into the reaction product of (A) and (B) via formula (I); and/or (b) reaction of the hydroxyl group, formed by ring opening of the epoxide ring of formula (II), and/or of the NH group, 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.

9. The dispersion as claimed in claim 1, the at least one epoxide-amine product being a further product of salification and/or quaternization of the nitrogen atom introduced into the reaction product of (A) and (B) via formula (I).

10. The dispersion as claimed in claim 1, the at least one epoxide-amine product being a further product of reaction of the hydroxyl group, formed by ring opening of the epoxide ring of formula (II), and/or of the NH group, 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.

Description

(1) The invention is to be explained in more detail hereinafter on the basis of exemplary embodiments.

EXAMPLES

(2) Measurement Methods

(3) Amine Number

(4) The amine number (AN) is understood to mean the amount of KOH in mg corresponding to the amine content of 1 g of substance. The amine number is determined according to DIN 16945 by a neutralization reaction with 0.1 N perchloric acid in acetic acid as titrant.
R—NH.sub.2+HClO.sub.4.fwdarw.R—NH.sub.3.sup.⊕ClO.sub.4.sup.⊖

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

(6) Epoxy Equivalent

(7) The epoxide equivalent weight is understood to mean that amount of epoxy resin in g that contains 16 g of epoxidically bonded oxygen (epoxide oxygen).

(8) The epoxide groups in epoxy resins can be determined by addition of HBr onto the epoxide ring. The equivalent amount of HBr is liberated by titration with HClO.sub.4 in the presence of cetyltrimethylammonium bromide (N,N,N-trimethyl-1-hexadecanaminium bromide; CTABr).

(9) Since the amine is also simultaneously protonated in the titration with perchloric acid, this amount of perchloric acid has to be subtracted in order to calculate the epoxy equivalent. It is therefore necessary to determine the amine number prior to determination of the epoxy equivalent.

(10) ##STR00008##
Epoxide equivalent=initial weight (gr.)*1000/(consumption (ml)*n*f)−(amine number/56.1)

(11) n=normality of the titrant

(12) f=factor of the titrant

(13) Acid Number

(14) The acid number is determined according to DIN EN ISO 2114 by a neutralization reaction with 0.1 N KOH in ethanol as titrant.
R—COOH+KOH R.fwdarw.COOK+H.sub.2O

Comparative Examples

(15) All non-inventive adducts and the pastes, lacquers and polymer concretes produced using said adducts are designated herein with a “*”.

(16) Epoxide-Amine Adduct EA1*

(17) 82 g of Epikote 828 (0.07 mol; undiluted difunctional bisphenol A-epichlorohydrin reaction product, manufacturer Momentive) are reacted with 528 g of Jeffamine M 2070 (0.085 mol; methanol-started polyether monoamine with terminal primary amino group, approximately 10 OPr and 31 OEt units; amine number=27 mg KOH/g; manufacturer Huntsman) at 140° C. for 27 h.

(18) Amine number: 19.6 mg KOH/g

(19) Epoxy equivalent: infinite

(20) Epoxide-Amine Adduct EA2*

(21) 82 g of Epikote 828 (0.22 mol) are reacted with 359 g of Jeffamine M 2070 (0.177 mol) and 8.6 g of dimethylaminopropylamine (0.08 mol) at 140° C. for 7 h. Subsequently, 145 g of a polyether-tolylene diisocyanate adduct (preparation see below) are added and allowed to react at 65° C. for a further 5 h.

(22) Amine number: 21.7 mg KOH/g

(23) Epoxy equivalent: infinite

(24) Isocyanate content: 0.05%

Inventive Examples

(25) Epoxide-Amine Adduct EA3

(26) Cresyl glycidyl ether (1.042 mol) was reacted with Jeffamine M2070 (0.573 mol, 10% excess NH) at 140° C. for 16 h.

(27) Amine number: 23.99 mg KOH/g

(28) Epoxy equivalent: infinite

(29) Epoxide-Amine Adduct EA4

(30) Cresyl glycidyl ether (1.042 mol) was reacted with Jeffamine M2005 (0.573 mol, 10% excess NH) at 140° C. for 16 h.

(31) Amine number: 22.54 mg KOH/g

(32) Epoxy equivalent: infinite

(33) Epoxide-Amine Adduct EA5

(34) Cresyl glycidyl ether (1.042 mol) was reacted with Surfonamine L200 (0.546 mol, 5% excess NH) at 140° C. for 16 h.

(35) Amine number: 24 mg KOH/g

(36) Epoxy equivalent: infinite

(37) Epoxide-Amine Adduct EA6

(38) Cresyl glycidyl ether (2.83 mol) was reacted with 1462.30 g of Surfonamine L 100 (1.486 mol, 5% excess NH) at 140° C. for 16 h.

(39) Amine number: 60 mg KOH/g

(40) Epoxy equivalent: infinite

(41) Epoxide-Amine Adduct EA7

(42) Cresyl glycidyl ether (0.75 mol) and Grilonit RV1814 (0.762 mol) were reacted with Jeffamine M2070 (0.83 mol, 10% excess NH) at 140° C. for 16 h.

(43) Amine number: 22.9 mg KOH/g

(44) Epoxy equivalent: infinite

(45) Epoxide-Amine Adduct EA8

(46) Vikolox 16 (0.49 mol, C16 alpha-olefin oxide from Arkema) and cresyl glycidyl ether (0.75 mol) were reacted with Jeffamine M2070 (0.68 mol) at 140° C. for 16 h.

(47) Amine number: 22.9 mg KOH/g

(48) Epoxy equivalent: infinite

(49) Epoxide-Amine Adduct EA9 (Salification)

(50) 49 g of EA8 (0.02 mol) is reacted with 2.35 g (0.02 mol) of benzoic acid in 8 g of Dowanol PMA at 50° C. for 1 h.

(51) Amine number: 19.2 mg KOH/g

(52) Acid number: 18.6 mg KOH/g

(53) SC: 80%

(54) Epoxide-Amine Adduct EA10 (Quaternization of the Salified Adduct EA9)

(55) 29.2 g of EA9 (0.01 mol) is reacted with 1.67 g (0.01 mol) of cresyl glycidyl ether in 0.42 g of Dowanol PMA at 120° C. for 4 h.

(56) Amine number: 18.4 mg KOH/g

(57) Acid number: 17.0 mg KOH/g

(58) SC: 80%

(59) Epoxide-Amine Adduct EA11

(60) 1000 g of EA8 (0.41 mol) is 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° C. for 4 h.

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

(62) SC: 60%

Non-Inventive Comparative Example 1*

(63) The comparative example was produced in accordance with the instructions for polymer 4 of the international publication WO 2016059066 A1.

(64) Performance Testing

(65) Use of the polymers according to the invention as wetting agents and dispersants for production of pigment concentrates and use thereof in paint systems.

(66) Starting Materials

(67) TABLE-US-00001 Gloss Enamel 275 Lacryl-PU gloss enamel, water-based acrylic paint, PU-reinforced, manufacturer: Brillux Heliogen blue pigment, color index PB 15:3, manufacturer: Blue D 7086 BASF Heliogen green pigment, color index PG 7, manufacturer: Green L 8730 BASF Permanent orange pigment, color index PO 34, manufacturer: Orange RL 70 Clariant Hostaperm blue pigment, color index PB 15:0, manufacturer: Blue A2R Clariant Rocima 512 biocide mixture of chloromethyl-/methylisothiazolone, octylisothiazolone and bronopol, manufacturer: Dow Chemical Preventol biocide mixture of isothiazolones and bronopol, P 91 MV manufacturer: Lanxess Polyglykol polyglycol of molar mass approximately 400 g/mol, P 400 manufacturer: Clariant Arkopal N 100 nonylphenol ethoxylate, manufacturer: Clariant Lansurf CO12 castor oil ethoxylate, manufacturer: Lankem MAKON ® polyarylphenyl ethoxylate, manufacturer: Stepan TSP 25 Algene WF alkylamine ethoxylate, manufacturer: Huntsman
The Production of Pigment Pastes and Coating Formulations

(68) The pigment pastes PP were produced according to the formulations in tables 1 to 4 below. The wetting and dispersing additive, 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 weighed in this order into a beaker and homogenized by hand using a spatula. Subsequently, the respective amount of pigment was incorporated a little at a time using a toothed disk in a Dispermat at around 500 rpm (1.5 m/s). Next, the batches were homogenized in the Dispermat for 10 minutes at 3000 rpm (9 m/s). Thereafter, the pH was adjusted with sulfuric acid, the batch was completed with Rocima 521 and the batch was transferred into a bead mill. The batch was then milled in the bead mill for one hour at 2800±50 rpm using SAZ-120-S beads (0.6-0.8 mm).

(69) TABLE-US-00002 TABLE 1 Pigment PB 15:3 PP1a* PP1b* PP1e* PP1f* PP1c PP1d Algene WF 9.4 Arkopal N 100 4.7 Comparative 14.1 example 1* EA1* 14.1 EA2* 14.1 EA6 14.1 EA3 14.1 Polyglykol 7.3 7.3 7.3 7.3 7.3 7.3 P 400 Demineralized 32.5 32.5 32.5 32.5 32.5 32.5 water Preventol P 0.14 0.14 0.14 0.14 0.14 0.14 91 MV Heliogen 45.0 45.0 45.0 45.0 45.0 45.0 Blue D 7086 15:3 H.sub.2SO.sub.4, 25% 0.64 0.64 0.64 0.64 0.64 0.64 Rocima 521 0.3 0.3 0.3 0.3 0.3 0.3 Sum total of the 100.0 100.0 100.0 100.0 100.0 100.0 parts by weight

(70) TABLE-US-00003 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 Demineralized water 31.30 31.30 31.30 31.30 Preventol P 91 MV 0.14 0.14 0.14 0.14 Hostaperm Blue A2R 15:0 43.0 43.0 43.0 43.0 H.sub.2SO.sub.4, 25% 0.38 0.38 0.38 0.38 Rocima 521 0.30 0.30 0.30 0.30 Sum total of the parts by weight 100.0 100.0 100.0 100.0

(71) TABLE-US-00004 TABLE 3 Pigment PG 7 PP3a* PP3d* PP3e* PP3b* PP3c Algene WF 9.0 Arkopal N 100 4.5 Comparative example 1* 13.5 EA1* 13.5 EA2* 13.5 EA6 13.5 Polyglykol P 400 6.5 6.5 6.5 6.5 6.5 Demineralized water 30.8 30.8 30.8 30.8 30.8 Preventol P 91 MV 0.14 0.14 0.14 0.14 0.14 Heliogen Green L 8730 48.0 48.0 48.0 48.0 48.0 H.sub.2SO.sub.4, 25% 0.76 0.76 0.76 0.76 0.76 Rocima 521 0.30 0.30 0.30 0.30 0.30 Sum total of the 100.0 100.0 100.0 100.0 100.0 parts by weight

(72) TABLE-US-00005 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 Demineralized water 40.97 40.97 40.97 Preventol P 91 MV 0.14 0.14 0.14 Permanent Orange RL 70 37.5 37.5 37.5 H.sub.2SO.sub.4, 25% 0.59 0.59 0.59 Rocima 521 0.30 0.30 0.30 Sum total of the parts by weight 100.0 100.0 100.0

(73) It was not possible to obtain a further-processable formulation of the pastes with the dispersant of non-inventive comparative example 1* (pigment pastes: PP1b*, PP1e*, PP1f* PP2b* and PP3b*, PP3d*, PP3e*), since in these cases either a strong thickening of the paste occurred after grinding, or gel particles could be seen.

(74) The pigment pastes obtained, which were in a processable range in terms of their viscosity, were mixed in a ratio of 3 parts by weight of pigment paste to 97 parts by weight of Brillux Gloss Enamel 275 (white, base 40). The pastes were stirred with the spatula and then homogenized for 3 minutes using the Skandex shaker (the compositions of the coating formulations can be seen in table 5). The lacquer was applied to a contrast chart using a 150 μm bar applicator and rubbed out at one location. The lacquer films were flashed off at 23° C. for 5 to 10 minutes. The rub-out test was performed immediately afterwards. The films were then cured for 24 h at 23° C. before the ΔL, Δa, Δb and ΔE values were determined.

(75) TABLE-US-00006 TABLE 5 Coating Parts by weight/Brillux Gloss Parts by weight/ formulation Enamel 275 (white base 40) pigment paste F1a* 97 3/PP1a* F1c 97 3/PP1c F1d 97 3/PP1d F2a* 97 3/PP2a* F2c 97 3/PP2c F2d 97 3/PP2d F3a 97 3/PP3a F3c 97 3/PP3c F4a* 97 3/PP4a* F4b 97 3/PP4b F4c 97 3/PP4c

(76) The color intensity and the L, a, b and ΔE values were measured with a Color Sphere Gloss instrument (available from BYK Gardner), in each case on the white area of the contrast chart. The color intensity was measured in % and the ΔL, Δa, Δb and ΔE values were measured relative to the respective reference formulation containing wetting and dispersing additives from the prior art. In addition, the ΔL, Δa, Δb and ΔE values of the rub-out were measured in comparison with the unloaded area.

(77) The measurement results for the individual coating formulations can be gathered from tables 6 to 9.

(78) TABLE-US-00007 TABLE 6 Coating formulation F1a* F1c F1d Color intensity 100 106.8 104.8 versus F1a* Color versus F1a* ΔL 0 1.76 −0.29 Δa 0 −1.35 −0.68 Δb 0 −1.54 −0.77 ΔE 0 2.70 1.06 Rub-out ΔL 1.84 0.23 0.11 Δa −1.26 0.02 0.01 Δb −1.92 −0.08 −0.09 ΔE 2.94 0.24 0.14

(79) TABLE-US-00008 TABLE 7 Coating formulation F2a* F2c F2d Color intensity 100 103.5 102.00 versus F2a* Color versus F2a* ΔL 0 −0.22 −0.19 Δa 0 −0.57 −0.08 Δb 0 −0.73 −0.37 ΔE 0 0.94 0.42 Rub-out ΔL −0.74 0.55 −0.15 Δa 0.22 −0.03 −0.01 Δb −1.04 −0.01 −0.13 ΔE 1.29 0.55 0.19

(80) TABLE-US-00009 TABLE 8 Coating formulation F3a* F3c Mixed into Gloss Enamel 275, base 40 Color intensity 100 101.9 versus F3a* Color versus F3a* ΔL 0 0.01 Δa 0 −0.05 Δb 0 −0.09 ΔE 0 0.50 Rub-out ΔL 2.54 0.53 Δa −1.87 −0.26 Δb −0.19 −0.07 ΔE 3.15 0.59

(81) TABLE-US-00010 TABLE 9 Coating formulation F4a* F4b F4c Color intensity 100 103.8 104.1 versus F4a* Color versus F4a* ΔL 0 2.05 0.99 Δa 0 1.80 1.41 Δb 0 2.48 2.22 ΔE 0 3.86 2.81 Rub-out ΔL 2.39 0.26 0.10 Δa 0.61 −0.47 −0.29 Δb 1.14 −0.25 −0.51 ΔE 2.71 0.59 0.59

(82) In summary, for the use of the inventive epoxide-amine adducts in pigment concentrates, it can be stated that significantly higher color intensities have been achieved than with wetting and dispersing additives of the prior art. In the formulations F1c, F1d, F2c and F2d, by the use of the inventive additives, the blue shades were shifted as desired to a deeper blue compared to the formulations F1a* and F2a*, respectively, (−b component). The green formulation F3c appears significantly greener (−a component) than the corresponding reference formulation F3a* and the orange-colored formulations F4b and F4c show a significantly stronger red and yellow component (+a and +b components) by way of the use of the inventive epoxide-amine adducts in comparison to formulation F4a*. The inventive additives stabilize the color pastes very well and achieve significantly better □E values in the rub-out.

(83) Production and Testing of Polymer Concrete Compositions

(84) TABLE-US-00011 Raw materials Palatal P4-01 unsaturated polyester resin based on o-phthalic acid and glycols dissolved in styrene, manufacturer: Aliancys BYK-C 8000 reactive polymeric coupling agent, manufacturer: BYK Akzo NL-51P Co(II) 2-ethylhexanoate, accelerator for unsaturated polyester resins, manufacturer: Akzo Nobel Dorsilit 7 crystalline quartz sand of grain size 0.6 to 1.2 mm, manufacturer: Dorfner Dorsilit 8 crystalline quartz sand of grain size 0.3 to 0.8 mm, manufacturer: Dorfner Millisil W 10 quartz flour, manufacturer: Quarzwerke Hostaperm Red quinacridone red pigment, manufacturer: Clariant E3B Trigonox C tert-butyl peroxybenzoate, free-radical initiator, manufacturer: Akzo Nobel
1. Production of Filled, Unsaturated Polyester Resins (UP) for the Purpose of Determining the Reduction in Viscosity

(85) The UP resin and the additive were initially charged in a beaker having an 80 mm diameter and stirred by hand with a spatula. The filler Millisil W10 was then weighed in and likewise stirred in with a spatula. Thereafter, this compound was dispersed under the following conditions: 1 min by means of a dissolver (40 mm dissolver disk, circumferential speed 1.95 m/s (930 rpm)), and a further 2 min by means of a dissolver (40 mm dissolver disk, circumferential speed 3.9 m/s (1865 rpm)). The corresponding formulations are given in table 10.

(86) After dispersing, the sample was filled into an aluminum cup and stored in a water bath for 30 minutes at 30° C. The viscosity in pascal seconds was determined at 30° C. using a Brookfield DV II+ rotational viscometer (spindle 6, shear rate 20 rpm). The viscosities and also the percentage reductions in viscosity compared to UP1* are given in table 10.

(87) TABLE-US-00012 TABLE 10 Formulation UPI* 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 total of the 100.00 100.00 100.00 100.00 100.00 100.00 parts by weight Viscosity [Pa .Math. s] 80.8 51.8 58.4 37.6 46.0 36.2 Reduction of 35.9 27.7 53.5 43.1 55.2 viscosity [%] 1% additive based on filler The inventive formulations UP4, UP5 and UP6, which contain the epoxide-amine adducts according to the invention, are able to lower the viscosity of the formulation much more significantly compared to conventional wetting agents and dispersants of the prior art. This is particularly pronounced in the case of formulations UP4 and UP6, which make use of EA3 and EA7. In EA3 and EA7, n > m (EtO:PrO = 31:10), whereas for EA4 m > n (EtO:PrO = 6:29).

(88) This test is a preliminary test in the context of polymer concrete production. It was used to determine the influence of additives on the viscosity reduction. For this purpose, neither a coupling agent (BYK C 8000) nor a catalyst was initially used. Furthermore, the addition of coarse silicates was dispensed with in order to perform the viscosity measurements.

(89) 2. Production of the Polymer Concrete Compositions

(90) The UP resin (Palatal P4-01), coupling agent (adhesion promoter) (BYK C 8000), a co-accelerator (Akzo NL-51P) and free-radical initiator (Trigonox C) were initially charged in a beaker. The quantities are shown in table 11. Subsequently, wetting and dispersing additive and pigment were added and stirred by hand. Thereafter, the quartz mix and the quartz flour were added and stirred by hand. The compound was then homogenized for 10 seconds at 1650 rpm in a Speed Mixer DAC 400.1 FVZ.

(91) 3. Production of Polymer Concrete Tiles (PCT)

(92) A square metal spacer frame (approximately 6 mm thick, 20 cm edge length) is lined with a PE film and the sample of the polymer concrete composition is spread in the metal spacer frame. The filled metal spacer frame is covered with a PE film prior to pressing in order to avoid contamination of the press. Subsequently, the specimen thus produced is pressed using a Polystat 200T press for 5 minutes at 50 bar (approximately 250 N/cm.sup.2) and 90° C. The pressed composition is then removed from the spacer frame and placed on a glass plate that has been pretreated with a release wax. The final curing of the polymer concrete tile is effected in an air circulation drying cabinet at 80° C. for 1 hour. The polymer concrete compositions are given in table 11.

(93) The cured polymer concrete tiles are subsequently assessed with respect to their surface properties according to a school-grade system from 1 to 6. In this case, 1 stands for a smooth, compacted surface without deep holes and with good leveling. Such samples have desired properties such as high strength, few air inclusions and high-quality appearance. 6 stands for a rough surface that has a very inhomogeneous, porous appearance and indicates a poor compaction. Such samples exhibit lower strength, have deep defects or crumble. The ratings are given in table 11. When using inventive epoxide-amine adducts (EA3, EA4 and EA7), it was possible to detect a greatly improved surface quality.

(94) TABLE-US-00013 TABLE 11 Formulation PCT1* PCT2* PCT3* PCT4 PCT5 PCT6 Palatal P4-01 19.00 18.43 18.43 18.43 18.43 18.43 BYK-C 8000 0.19 0.19 0.19 0.19 0.19 0.19 Akzo NL-51P 0.04 0.04 0.04 0.04 0.04 0.04 Trigonox C 0.38 0.38 0.38 0.38 0.38 0.38 BYK-W 908 — 0.57 — — — — BYK-W 909 — — 0.57 — — — EA3 — — — 0.57 — — EA4 — — — — 0.57 — EA7 — — — — — 0.57 Hostaperm 2.09 2.09 2.09 2.09 2.09 2.09 Red E3B Dorsilit 7/Dorsilit 122.00 122.00 122.00 122.00 122.00 122.00 8(1:1) Millisil W 10 59.00 59.00 59.00 59.00 59.00 59.00 Surface quality 6 4 3 1 2 1 The inventive formulations PCT4, PCT5 and PCT6, which contain the epoxide-amine adducts according to the invention, provide an outstanding surface quality compared to conventional wetting agents and dispersants of the prior art. This is particularly pronounced in the case of formulations PCT4 and PCT6, which make use of EA3 and EA7. In EA3 and EA7, n > m (EtO:PrO = 31:10), whereas for EA4 m > n (EtO:PrO = 6:29).