ALKOXYLATED POLYAMIDOAMINES AS DISPERSANT AGENTS

Abstract

An alkoxylated polyamidoamine obtainable by a) reacting a polycarboxylic compound having a total number TN of carboxylic groups of 3 to 10 with a primary diamine of formula I H.sub.2N—Z—NH.sub.2 wherein Z represents a bond or an organic group with 1 to 20 carbon atoms in a ratio of 0.3 TN to TN mols of the diamine per 1 mol of the polycarboxylic compound and b) alkoxylating the product obtained in a) with at least 0.5 mol of alkyleneoxide per 1 mol of primary amino groups

Claims

1. An alkoxylated polyamidoamine obtainable by: a) reacting a polycarboxylic compound having a total number TN of carboxylic groups of 3 to 10 with a primary diamine of formula I:
H.sub.2N—Z—NH.sub.2 wherein Z represents a bond or an organic group with 1 to 20 carbon atoms in a ratio of 0.3 TN to TN mols of the diamine per 1 mol of the polycarboxylic compound, and b) alkoxylating the product obtained in a) with at least 0.5 mol of alkyleneoxide per 1 mol of primary amino groups.

2. The alkoxylated polyamidoamine according to claim 1, wherein the carboxylic groups are selected from carboxylic acid groups, carboxylic halogenid groups, carboxylic ester groups, carboxylic anhydride groups, and mixtures thereof, whereby a carboxylic anhydride group corresponds to two carboxylic groups.

3. The alkoxylated polyamidoamine according to claim 1, wherein the carboxylic compound is a compound of formula II: ##STR00002## wherein X.sup.1 to X.sup.3 independently from each other represent a halogenid, cyanide or a group O—R.sup.1 with R.sup.1 being hydrogen or an organic group with at maximum 30 carbon atoms, and R represents hydrogen or a group C(═O)—R.sup.2 with R.sup.2 being an organic group with at maximum 30 carbon atoms

4. The alkoxylated polyamidoamine of claim 1, wherein Z in formula I is an aliphatic hydrocarbon group comprising a cycloaliphatic ring system

5. The alkoxylated polyamidoamine of claim 1, wherein the diamine of formula I is 1-methyl-2,4-diamine-cyclohexane, 1-methyl-2,6-diamine-cyclohexane or mixtures thereof.

6. The alkoxylated polyamidoamine of claim 1, wherein the polycarboxylic compound and the diamine are reacted in a ratio of 0.3 TN to 0.98 TN mols of the diamine per 1 mol of the polycarboxylic compound.

7. The alkoxylated polyamidoamine of claim 1, wherein the polyamidoamine obtained in step a) has an amine number of 100 to 1500 mg KOH/g.

8. The alkoxylated polyamidoamine of claim 1, wherein the alkyleneoxide used in step b) is an alkyleneoxide with 2 to 6 carbon atoms.

9. The alkoxylated amidoamine of claim 1, wherein the degree of alkoxylation of the alkoxylated polyamidoamine is 0.5 to 100 mols of alkyleneoxide per 1 mol of primary amino groups of the polyamidoamine obtained in step a).

10. The alkoxylated polyamidoamine of claim 1, wherein the alkoxylated polyamidoamine has a number average molecular weight (Mn) of 300 to 50.000 g/mol.

11. Use of A method of using the alkoxylated polyamidoamine of claim 1, the method comprising using the alkoxylated polyamidoamine as a dispersant.

12. A method of using the alkoxylated polyamidoamine of claim 1, the method comprising using the alkoxylated polyamidoamine as a dispersant for the preparation of pigment dispersions.

13. Pigment dispersions comprising: a pigment, the alkoxylated polyamidoamine of claim 1, and a solvent selected from water, organic solvents, or mixtures thereof.

14. Use of A method of using the pigment dispersions of claim 13, the method comprising using the pigment dispersions for the preparation of aqueous or organic solvent based coating compositions, adhesives, or sealants.

Description

EXAMPLES

Synthesis of Polymers

Example 1: Polyamidoamine 1

[0125] 138.15 g of triethylcitrate were placed in a 500 mL four-necked flask equipped with a stirrer a condensation column, a thermometer and a Nitrogen inlet. 179.51 g of Methyldiaminocyclohexane were added dropwise to the reaction flask within 10 minutes under stirring. The reaction mixture was slowly heated up to 95 C (external temperature) and kept at this temperature under stirring for 5 Hours under nitrogen. Ethanol was collected as distillate. Then the pressure within the reactor was gradually reduced to 40 mbar and the reaction was continued for 2 and ½ hours under stirring. Then, the temperature of the external heat source was slowly increased to 112 C and kept 2 hours under stirring. Ethanol was further collected as distillate. The reaction temperature was then reduced to room temperature and 284.5 g of fluid product were collected.

[0126] The polymer was characterized via Gel Permeation Chromatography in hexafluoroisopropanol and amino numbers:

[0127] Mn: 341 g/mol

[0128] Mw: 1000 g/mol

[0129] PD*: 2.9

[0130] Amino number**: 458 mgKOH/g

[0131] Viscosity: 300 mPas @ 23 C and 100 1/s

[0132] *PD: polydispersity (Mw/Mn)

Example 2: Polyamidoamine 2

[0133] 331.55 g of triethylcitrate were placed in a 1 L four-necked flask equipped with a stirrer a condensation column, a thermometer and a Nitrogen inlet. 430.82 g of Methyldiaminocyclohexane were added dropwise to the reaction flask within 20 minutes under stirring. The reaction mixture was slowly heated up to 143 C (external temperature) and kept at this temperature under stirring for 6 hours. Ethanol was collected as distillate. Then the temperature of the external heat source was reduced to 105 C and slowly the pressure was reduced to 250 mbar within 1½ hour. Ethanol was further collected as distillate. The reaction temperature was then reduced to room temperature and 623 g of viscous fluid product were collected.

[0134] The polymer was characterized via Gel Permeation Chromatography in hexafluoroisopropanol.

[0135] Mn: 407 g/mol

[0136] Mw: 1970 g/mol

[0137] PD*: 4.8

[0138] Amino number: 425 mg KOH/g

[0139] Viscosity: 9800 mPas @ 40 C and 100 1/s

Example 3: Polyamidoamine 3

[0140] 331.55 g of triethylcitrate were placed in a 1 L four-necked flask equipped with a stirrer a condensation column, a thermometer and a Nitrogen inlet. 430.82 g of Methyldiaminocyclohexane were added dropwise to the reaction flask within 20 minutes under stirring. The reaction mixture was slowly heated up to 143 C (external temperature) and kept at this temperature under stirring for 8 hours. Ethanol was collected as distillate. Then the temperature of the external heat source was reduced to 105 C and slowly the pressure was reduced to 350 mbar within 30 minutes and kept at 350 mbar for further 30 minutes under stirring. Ethanol was further collected as distillate. The reaction temperature was then reduced to 80° C. and 541.7 g of viscous product were collected. The polyamidoamine was solid at room temperature.

[0141] The polymer was characterized via Gel Permeation Chromatography in hexafluoroisopropanol and amino numbers:

[0142] Mn: 667 g/mol

[0143] Mw: 4010 g/mol

[0144] PD*: 6

[0145] Amino number: 402 mgKOH/g

Example 4

Polymer A=Polyamidoamine 1 Ethoxylated with 40 Ethoxy Groups Per Primary Amino Group

[0146] 122.0 g polyamidoamine 1 from example 1 and 16 g water (10% relative to total amount) were charged in a 2 L autoclave and flushed with nitrogen. The reactor was heated to 120° C. and 35 g ethylene oxide were dosed within 10 minutes and the mixture was stirred overnight. Then, 4 g of an aqueous potassium hydroxide solution (50% wt) were added and the water was removed from the system by heating the reactor to 120° C. under reduced pressure. Subsequently, 30 g ethylene oxide were dosed to reaction mixture within 10 minutes and afterwards 816 g ethylene oxide were added within 16 hours. The reaction mixture was allowed to post-react for 6 hours and subsequently the reactor was cooled to 100° C. The reaction mixture was stripped with nitrogen and volatile compounds were removed in vacuo at 80° C. 1010 g of the ethoxylated polyamidoamine were obtained. The ethoxylated polyamidoamine was liquid at room temperature.

[0147] The polymer was characterized by Gel Permeation Chromatography in THF.

[0148] Mn (THF): 670 g/mol

[0149] MW (THF): 1700 g/mol

[0150] PD: 2.5

[0151] Total Amine number: 45 mg KOH/g

[0152] Tert. Amine number: 42 mg KOH/g

[0153] Hydroxyl number: 129 mg KOH/g

Example 5

Polymer B=Polyamidoamine 2 Ethoxylated with 40 Ethoxy Groups Per Primary Amino Group

[0154] 133.8 g polyamidoamine 2 from example 2 and 16 g water (10% relative to total amount) were charged in a 2 L autoclave and flushed with nitrogen. The reactor was heated to 120° C. and 35 g ethylene oxide were dosed within 10 minutes and the mixture was stirred overnight. Then, 4 g of an aqueous potassium hydroxide solution (50% wt) were added and the water was removed from the system by heating the reactor to 120° C. under reduced pressure. Subsequently, 30 g ethylene oxide were dosed to reaction mixture within 10 minutes and afterwards 816 g ethylene oxide were added within 16 hours. The reaction mixture was allowed to post-react for 6 hours and subsequently the reactor was cooled to 100° C. The reaction mixture was stripped with nitrogen and volatile compounds were removed in vacuo at 80° C. 1020 g of the ethoxylated polyamidoamine were obtained. The ethoxylated polyamidoamine was solid at room temperature.

[0155] The polymer was characterized by Gel Permeation Chromatography in THF.

[0156] Mn (THF): 3500 g/mol

[0157] MW (THF): 6600 g/mol

[0158] PD: 1.9

[0159] Total Amine number: 59 mg KOH/g

[0160] Tert. Amine number: 54 mg KOH/g

[0161] Hydroxyl number: 159 mg KOH/g

Example 6

Polymer C=Polyamidoamine 3 Ethoxylated with 38.4 Ethoxy Groups Per Primary Amino Group

[0162] 145 g polyamidoamine 3 from example 3 and 16 g water (10% relative to total amount) were charged in a 2 L autoclave and flushed with nitrogen. The reactor was heated to 120° C. and 35 g ethylene oxide were dosed within 10 minutes and the mixture is stirred overnight. Then, 4 g of an aqueous potassium hydroxide solution (50% wt) were added and the water was removed from the system by heating the reactor to 120° C. under reduced pressure. Subsequently, 30 g ethylene oxide were dosed to reaction mixture within 10 minutes and afterwards 816 g ethylene oxide were added within 16 hours. The reaction mixture was allowed to post-react for 6 hours and subsequently the reactor was cooled to 100° C. The reaction mixture was stripped with nitrogen and volatile compounds were removed in vacuo at 80° C. 1036 g of the ethoxylated polyamidoamine were obtained. The ethoxylated polyamidoamine was solid at room temperature.

[0163] The polymer was characterized by Gel Permeation Chromatography in THF.

[0164] Mn (THF): 590 g/mol

[0165] MW (THF): 1100 g/mol

[0166] PD: 1.9

[0167] Total Amine number: 58 mg KOH/g

[0168] Tert. Amine number: 55 mg KOH/g

[0169] Hydroxyl number: 150 mg KOH/g

Example 7

Polymer D=Polyamidoamine 1 Propoxylated with 24 Propoxy Groups Per Primary Amino Group

[0170] 74.81 g polyamidoamine 1 from example 1 and 3.74 g water were charged in a 2 L autoclave and flushed with nitrogen. The reactor was heated to 100° C. and 30 g propylene oxide were dosed within 10 minutes and a further 45 g were dosed over 90 minutes. After completion of dosing, the mixture was stirred overnight. Then, 3.7 g of an aqueous potassium hydroxide solution (50% wt) were added and the water was removed from the system by heating the reactor to 120° C. under reduced pressure. Subsequently, 30 g propylene oxide were dosed to reaction mixture within 10 minutes and afterwards 747 g propylene oxide were added over 800 minutes. The reaction mixture was allowed to post-react for 6 hours and subsequently the reactor was cooled to 100° C. The reaction mixture was stripped with nitrogen and volatile compounds were removed in vacuo at 80° C. 899.7 g of the propoxylated polyamidoamine were obtained.

[0171] The polymer was characterized by Gel Permeation Chromatography in THF.

[0172] Mn (THF): 1700 g/mol

[0173] MW (THF): 2200 g/mol

[0174] PD: 1.29

[0175] Total Amine number: 34 mg KOH/g

Application Examples

[0176] Materials Used

[0177] Polymers A, B, C and D of example 4 to 7 are alkoxylated polyamidoamines. They were used as dispersant for the preparation of a pigment paste. The pigment paste was added to aqueous coating systems.

[0178] Sokalan® HP 20 (shortly referred to as Polymer S) was used for comparison; polymer S is an ethoxylated polyethyleneimine solved in water (solid content 80% by weight).

[0179] As pigments the carbon black pigments Special Black 100 and Colour Black FW 200 were used.

[0180] Polymers A to D were provided as highly viscous solvent-free materials with an active content of 100%. For incorporating Polymers A to D into the respective pigment dispersions the samples were heated up to 60° C. for easier handling. As Polymer S is a solution it could be simply added with increase of temperature. Pigment dispersions were prepared by mixing the components in the respective amounts and milling them down to their primary particle sizes.

[0181] The characterization of the pigments used is outlined in Table 1 below. The pigments were selected from the pigment class Pigment Black 7 (PBK 7) and are chemically composed of amorphous carbon from soot by incomplete combustion of hydrocarbons, and having different particle sizes and specific surface areas.

[0182] The pigment Color Black FW 200, if well dispersed, leads to rather transparent black coating films due to its small primary particles at <20 nm, and is used for tinting of high quality coatings. Special Black 100 has a slightly larger particle size of 50 nm, is used for mass tones in water-based coatings.

TABLE-US-00001 TABLE 1 Pigments used BET Average Particle Pigment name Class Supplier (m2/g) size D50 Special Black 100 PBk 7 Orion 35 51 nm Colour Black FW 200 PBk 7 Orion 550 13 nm

[0183] At low addition levels of these pigments to a binder system, being less than 10 wt % in the dry film, they can show a transparent behaviour, indicating the quality of the dispersion. The smaller the particle size of the carbon black particle was achieved during the milling step of the pigment paste, the more transparent the dry film appears after its let-down and curing.

[0184] Applications Examples for Water Based Systems

[0185] The pigment dispersions were prepared by mixing the components in the respective addition level as outlined in Tables 2 and 3 below for each of the pigments at two different DOP levels, by which is meant the percentage of weight of active dispersant on weight of pigment.

[0186] Pigment Dispersions

[0187] The pigment dispersions are also referred to as pigment pastes.

[0188] Pigment pastes were prepared by mixing the components listed in table 2 and 3 and adding glass beads in an amount of 40 g (1 part of weight of glass beads per 1 part of the total weight of all components) The mixtures of table 2 and 3 were Skandex® shaken in parallel for 2 hours at room temperature and the glass beads were removed by filtration. The rheology of the obtained pigment dispersions was measured after 24 hrs by using a Paar Physika UDS 200 rheometer with a cone/plate geometry. Viscosities were measured in the shear rate ranges from 0.01 to 1024 1/s. For evaluation the viscosities at a shear rate of 1.0 1/s were compared, see viscosities of the pigment dispersions in Tables 5 and 6 in mPas.

TABLE-US-00002 TABLE 2a pigment dispersions with Special Black 100 (25% pigment, 25% DOP) Pigment dispersion A1 B1 C1 S1 O1 Dispersing Polymer A Polymer B Polymer C Sokalan Blank agent (100%) (100%) 100%) HP 20 (80% in water) Amount of 2.50 g 2.50 g 2.50 g 3.13 g 0.0 g dispersing agent Water 25.75 g 25.75 g 25.75 g 25.12 g 25.75 g PEG 300 1.75 g 1.75 g 1.75 g 1.75 g 1.75 g Pigment 10.0 g 10.0 g 10.0 g 10.0 g 10.0 g Total 40.0 g 40.0 g 40.0 g 40.0 g 40.0 g

TABLE-US-00003 TABLE 2b pigment dispersions with Special Black 100 (25% pigment, 50% DOP) Pigment dispersion A2 B2 C2 S2 Dispersing Polymer A Polymer B Polymer C Sokalan agent (100%) (100%) (100%) HP 20 (80% in water) Dispersing 5.00 g 5.00 g 5.00 g 6.25 g agent Water 23.25 g 23.25 g 23.25 g 22.00 g PEG 300 1.75 g 1.75 g 1.75 g 1.75 g Pigment 10.0 g 10.0 g 10.0 g 10.0 g Total 40.0 g 40.0 g 40.0 g 40.0 g

TABLE-US-00004 TABLE 3a pigment dispersion with Colour Black FW 200 (15% pigment, 50% DOP) Pigment dispersion A3 B3 C3 S3 O2 Dispersing Polymer A Polymer B Polymer C Sokalan Blank agent (100%) (100%) (100%) HP 20 (80% in water) Amount of 3.0 g 3.0 g 3.0 g 3.75 g 0.0 g Dispersing agent Water 31.0 g 31.0 g 31.0 g 30.25 g 34.0 g Pigment 6.0 g 6.0 g 6.0 g 6.0 g 6.0 g Total 40.0 g 40.0 g 40.0 g 40.0 g 40.0 g

TABLE-US-00005 TABLE 3b pigment dispersions with Colour Black FW 200 (15% pigment, 100% DOP) Pigment dispersion A4 B4 C4 S4 Dispersing Polymer A Polymer B Polymer C Sokalan agent (100%) (100%) (100%) HP 20 (80% in water) Amount 6.0 g 6.0 g 6.0 g 7.50 g Dispersing agent Water 28.0 g 28.0 g 28.0 g 26.50 g Pigment 6.0 g 6.0 g 6.0 g 6.0 g Total 40.0 g 40.0 g 40.0 g 40.0 g

[0189] Preparation of an Aqueous Based Coating Composition

[0190] A paint was prepared by mixing part of the pigment dispersions (pigment paste) with an acrylic water based resin system. As binder NeoCryl® XK-98 was used, which is an ammonia neutralized anionic acrylic copolymer emulsion ex. DSM Coating Resins and provides high gloss, early block resistance and good color development upon tinting.

[0191] The details regarding the acrylic water based system are outlined in Table 4 below.

[0192] The components listed in Table 4 were added subsequently and stirred with efficient agitation. The wetting agent was added to ensure good flow and levelling of the liquid coating on the substrate.

TABLE-US-00006 TABLE 4 components of the pigmented coating composition component Function w/w % Neocryl ® XK-98 (45% solids) Clear Binder 83.0% DSM Coating Resins Pigment dispersion Pigment paste 16.5% from examples above, see Table 5 Hydropalat ® WE 3220, Wetting Agent 0.5% BASF SE total 100.00%

[0193] The pigment dispersions were selected to obtain pigmented coatings comprising 4.1 wt % of the pigment Special Black 100 or, alternatively 2.5 wt % of Colour Black FW 200, based on the total weight of the obtained wet pigmented coating which corresponds to 8.8% of Special Black 100 or, alternatively, 5.2% of Colour Black FW 200 based on the dried film.

[0194] The pigmented coating was applied to a polyester sheet with a 50 μwire bar coater, and the film was dried overnight at room temperature.

[0195] For evaluation the gloss values at a 60°-angle were measured. For the measurements a Byk-Gardner Haze-Gloss-Spectrometer was used.

[0196] Negative impacts on appearance were seeding, surface roughness and haze.

[0197] Rating for appearance, transparency or opaqueness/hiding power were:

[0198] x=not measurable; 1=very poor; 2=poor; 3=mediocre; 4=good; 5=excellent.

[0199] The results for the pigmented coatings are outlined in Tables 5 for Special Black 100 and in Table 6 for Colour Black FW 200.

TABLE-US-00007 TABLE 5 results for pigmented coatings comprising Special Black 100 Viscosity of the Gloss Trans- pigment of the parency Appearance Pigment dispersion, coating of the of the DOP dispersion mPas at 60° coating coating  0% O1 28400 66 x not 1 dispersed floculated 25% S1 825 79 2 4 (comparison) 50% S2 715 80 3 3 (comparison) 25% A1 1070 77 4 5 50% A2 735 77 3 5 25% B1 1090 78 4 5 50% B2 1020 80 4 5 25% C1 1100 76 3 4 50% C2 1010 80 4 5

TABLE-US-00008 TABLE 6 results for pigmented coatings comprising Colour Black FW 200 Viscosity of the Gloss Trans- pigment of the parency Appearance Pigment dispersion, coating of the of the DOP dispersion mPas at 60° coating coating  0% O2 22′200 74 2 2 floculated 50% S3 112′000  83 4 5 (comparison) 100%  S4    50 84 5 5 (comparison) 50% A3 86′800 70 3 3 100%  A4  1′600 82 4 5 50% B3 70′100 82 4 5 100%  B4   450 83 5 5 50% C3 87′200 78 4 4 100%  C4    95 83 5 5

[0200] It can be seen from Table 5 and 6 that the use of the pigment dispersions comprising alkoxylated polyamidoamines show clearly improved properties in comparison to the blank experiment. In particular, it can be seen that the coatings with pigment dispersions A1 to A4, B1 to B4 and C1 to C4 show good performance in the order of magnitude for gloss, transparency, appearance of the coating obtained. In addition, the viscosity of the pigment dispersions A1-A4, B1-B4 and C1 to C4 compared to pigment dispersions S1 to S4, at both 25% and 50% addition level of dispersant on pigment Special Black 100 is in the same range.

[0201] At a level of 100% DOP a comparable performance on pigment Colour Black FW 200 with regard to the film gloss, viscosity and transparency was found. At a lower level of 50% DOP on Colour Black FW 200, slightly improved viscosities of the pigment dispersions were found compared to pigment dispersions S1 to S4.

[0202] In case of Special Black 100, in general a better transparency was obtained for the coatings with pigment dispersions A1 to A4, B1 to B4 and C1 to C4, as compared to coatings with pigment dispersions S1 to S4, indicating a better dispersion to smaller particle sizes.

[0203] Application Examples for an Organic Solvent Based Systems

[0204] The following section concerns the testing of alkoxylated polyamidoamines as dispersing agent with regard to their dispersing efficiency for carbon black pigment Colour Black FW 200 in a solvent-based coating system as shown in Table 7.

[0205] The pigment dispersions were prepared as described above. The pigment dispersion comprised 1-methoxy-2-propyl acetate as solvent.

TABLE-US-00009 TABLE 7 pigment dispersions with Colour Black FW 200 (15% pigment) Pigment dispersion D1 D2 O3 Dispersing agent 3.54 g of 7.0 g of — Polymer D Polymer D (corresponding (corresponding to 59% DOP) to 117% DOP) 1-Methoxy-2-propyl 30.46 g 27.0 g 34.0 g acetate Pigment 60 g 6.0 g 6.0 g Total 40.0 g 40.0 g 40.0 g

[0206] A paint was prepared by mixing part of the obtained pigment dispersion with a medium solid stoving enamel system.

[0207] The medium solid stoving enamel was composed as shown in Table 8.

TABLE-US-00010 TABLE 8 composition of the medium solid stoving enamel component Function w/w % Setal 173 VS-60 Saturated polyester binder 24.7% From Allnex CAB 381.2 & CAB 381.20 Cellulose acetate binder 23.1% (ratio 72/28) From Eastman Maprenal MF 650 Melamine crosslinker 11.5% From Ineos Resamine HF 480 Plasticizer Resin 2.9% From Allnex Butyl Acetate Solvent 18.9% From BASF Xylene Solvent 18.9% From BASF total 100.00%

[0208] The components of the medium solid stoving enamel were mixed and stirred with efficient agitation.

[0209] 10 parts by weight of the pigments dispersions D1, D2 or D3 were added to 90 parts by weight of the medium solid stoving enamel.

[0210] The final pigmented coating (wet) that was applied on the substrate thus contained 1.5 wt.-% of the pigment Colour Black FW 200, based on the total weight of the obtained wet pigmented coating and 3 wt % based on the cured film.

[0211] The final pigmented coating was applied to a polyester sheet with a 50 μwire bar coater, left at RT for 10 min for flash off and cured in an ventilated oven at 130° C. for 30 min.

[0212] For evaluation, the gloss values at a 20°-angle and 60°-angle, were measured. For the measurements a Byk-Gardner Haze-Gloss-Spectrometer was used.

[0213] Negative impacts on appearance were seeding, surface roughness and haze.

[0214] Rating for transparency and appearance were:

[0215] x=not measureable; 1=very poor; 2=poor; 3=mediocre; 4=good; 5=excellent.

[0216] The results for the pigmented coating are outlined in the following Table 9.

TABLE-US-00011 TABLE 9 results for pigmented coatings with pigment dispersion O3, D1 or D2 physical Trans- condition parency Appearance Pigment of the pigment Gloss Gloss of the of the dispersion dispersion visual at 20° at 60° coating coating O3 solid 21 56 x 1 floculated floculated D1 liquid 61 87 3 3 D2 liquid 82 93 5 4

[0217] It can be seen from Table 9 that the coating compositions and obtained coatings showed clearly improved optical properties with the alkoxylated polyamidoamines in comparison to the blank experiment on Colour Black FW 200. In particular, it can be seen that the coating with pigment dispersions D1 and D2 showed a clear advantage in gloss values at both 20 and 60° in comparison to a blank experiment. The improved pigment dispersion can also be concluded from the fact that the obtained pigment dispersions were solid without the alkoxylated polyamidoamines. The film transparency and appearance of the coatings with pigment dispersions D1 and D2 were clearly enhanced.