RHEOLOGY-MODIFYING TRIURETHANE COMPOUND

Abstract

A triurethane compound may be used to modify rheology. An aqueous composition may include such a triurethane compound and the viscosity of an aqueous composition may be controlled using the triurethane compound.

Claims

1. A triurethane compound, prepared by reacting: a. one molar equivalent of at least one polyisocyanate compound (a) comprising on average three isocyanate groups; and b. one molar equivalent of at least one polyalkoxylated compound (b) comprising (b1) a straight aliphatic comprising from 6 to 40 polyalkoxylated carbon atoms, (b2) a branched aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b3) a cycloaliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b4) a monoaromatic monoalcohol comprising from 6 to 30 polyalkoxylated carbon atoms, and/or (b5) a polyaromatic monoalcohol comprising from 10 to 80 polyalkoxylated carbon atoms, and c. two molar equivalents of at least two identical or different compounds (c) comprising (c1) a straight aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (c2) branched aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (c3) cycloaliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (c4) a monoaromatic monoalcohol comprising from 6 to 30 polyalkoxylated carbon atoms, (c5) a polyaromatic monoalcohol comprising from 10 to 80 polyalkoxylated carbon atoms, (c6) straight aliphatic monoalcohol (c6) comprising from 6 to 40 non-alkoxylated carbon atoms, (c7) a branched aliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms, (c8) a cycloaliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms, (c9) amonoaromatic monoalcohol (c9) comprising from 6 to 30 non-alkoxylated carbon atoms, and/or (c10) a polyaromatic monoalcohol comprising from 10 to 80 non-alkoxylated carbon atoms.

2. The triurethane compound of compound claim 1, prepared by reacting: a. one molar equivalent of the at least one triisocyanate compound (a); and b. one molar equivalent of the at least one polyalkoxylated compound (b) comprising (b1) the straight aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b2) the branched aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b3) the cycloaliphatic monoalcohol (b3) comprising from 6 to 40 polyalkoxylated carbon atoms, (b4) the monoaromatic monoalcohol comprising from 6 to 30 polyalkoxylated carbon atoms, and/or (b5) the polyaromatic monoalcohol comprising from 10 to 80 polyalkoxylated carbon atoms, and c. two molar equivalents of the at least one identical or different polyalkoxylated compound (c), comprising (c1) the straight aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (c2) the branched aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (c3) the cycloaliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (c4) the monoaromatic monoalcohol comprising from 6 to 30 polyalkoxylated carbon atoms, and/or (c5) the polyaromatic monoalcohol (c5) comprising from 10 to 80 polyalkoxylated carbon atoms.

3. The triurethane compound of claim 1, prepared by reacting: a. one molar equivalent of the at least one triisocyanate compound (a); and b. one molar equivalent of the at least one polyalkoxylated compound (b) comprising (b1) the straight aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b2) the branched aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b3) the cycloaliphatic monoalcohol (b3) comprising from 6 to 40 polyalkoxylated carbon atoms, (b4) the monoaromatic monoalcohol comprising from 6 to 30 polyalkoxylated carbon atoms, and/or (b5) the polyaromatic monoalcohol comprising from 10 to 80 polyalkoxylated carbon atoms; and c. one molar equivalent of the at least one identical or different polyalkoxylated compound (c), comprising (c1) the straight aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (c2) the branched aliphatic monoalcohol (c2) comprising from 6 to 40 polyalkoxylated carbon atoms, (c3) a cycloaliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (c4) a monoaromatic monoalcohol comprising from 6 to 30 polyalkoxylated carbon atoms, and/or (c5) a polyaromatic monoalcohol (c5) comprising from 10 to 80 polyalkoxylated carbon atoms, and one molar equivalent of the at least one identical or different non-alkoxylated compound (c), comprising (c6) the straight aliphatic monoalcohol (c6) comprising from 6 to 40 non-alkoxylated carbon atoms, (c7) the branched aliphatic monoalcohol (c7) comprising from 6 to 40 non-alkoxylated carbon atoms, (c8) the cycloaliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms, (c9) the monoaromatic monoalcohol comprising from 6 to 30 non-alkoxylated carbon atoms, and/or (c10) the polyaromatic monoalcohol comprising from 10 to 80 non-alkoxylated carbon atoms.

4. The triurethane compound of claim 1, prepared by reacting: a. one molar equivalent of the at least one triisocyanate compound (a); and b. one molar equivalent of the at least one identical or different polyalkoxylated compound (b), comprising (b1) the straight aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b2) the branched aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b3) the cycloaliphatic monoalcohol (b3) comprising from 6 to 40 polyalkoxylated carbon atoms, (b4) the monoaromatic monoalcohol comprising from 6 to 30 polyalkoxylated carbon atoms, and/or (b5) the polyaromatic monoalcohol comprising from 10 to 80 polyalkoxylated carbon atoms, and c. two molar equivalents of the at least one identical or different non-alkoxylated compound (c), comprising (c6) the straight aliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms, (c7) the branched aliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms, (c8) the cycloaliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms, (c9) the monoaromatic monoalcohol comprising from 6 to 30 non-alkoxylated carbon atoms, and/or (c10) thepolyaromatic monoalcohol (c10) comprising from 10 to 80 non-alkoxylated carbon atoms.

5. The triurethane compound of claim 1, wherein the reaction uses a single compound (a) or uses two or three different compounds (a), or wherein the compound (a) comprises: triphenylmethane-4,4′,4″-triisocyanate or 1,1′,1“-methylidynetris (4-isocyanatobenzene); an isocyanurate compound; and/or a biuret trimer compound .

6. The triurethane compound of claim 1, wherein the compound (a) comprises triphenylmethane-4,4′,4″-triisocyanate, 1,1′,1″-methylidynetris (4-isocyanatobenzene), an HDI isocyanurate, an IPDI isocyanurate, a PDI isocyanurate, an HDI biuret trimer, an IPDI biuret trimer, a PDI biuret trimer, or a combination thereof.

7. The triurethane compound of claim 1, having a degree of polyalkoxylation in a range of from 100 to 500, or wherein the polyalkoxylated monoalcohol comprises from 2 to 500 alkoxy groups, or wherein alkoxy groups are —CH.sub.2CH.sub.2O—, —CH.sub.2CH(CH.sub.3)O—, —CH(CH.sub.3)CH.sub.2O—, —CH(CH.sub.2CH.sub.3)CH.sub.2O—, —CH.sub.2CH(CH.sub.2CH.sub.3)O—, or a combination thereof.

8. The triurethane compound of claim 1, wherein a hydrocarbon chain of the monoalcohol (b1) comprises from 6 to 30 carbon atoms, or wherein one or more straight polyalkoxylated aliphatic monoalcohols (b1) are used to prepare the triurethane compound Ta and comprise from 80 to 500 alkoxy groups, or wherein a hydrocarbon chain of the monoalcohol (b2) comprises from 6 to 30 carbon atoms, or wherein a hydrocarbon chain of the monoalcohol (b3) comprises from 6 to 30 carbon atoms, or wherein a hydrocarbon chain of the monoalcohol (b4) comprises from 12 to 30 carbon atoms, or wherein the monoaromatic polyalkoxylated alcohol (b4) is used to prepare the triurethane compound Ta and comprises from 6 to 12 carbon atoms, or wherein a hydrocarbon chain of the monoalcohol (b5) comprises from 10 to 60 carbon atoms.

9. The triurethane compound of claim 1 wherein a hydrocarbon chain of the monoalcohol (c1) comprises from 6 to 30 carbon atoms, or wherein a hydrocarbon chain of the monoalcohol (c2) comprises from 6 to 30 carbon atoms, or wherein a hydrocarbon chain of the monoalcohol (c3) comprises from 6 to 30 carbon atoms, or wherein a hydrocarbon chain of monoalcohol (c4) comprises from 12 to 30 carbon atoms, or wherein a hydrocarbon chain of the monoalcohol (c5) comprises from 10 to 60 carbon atoms or wherein a hydrocarbon chain of monoalcohol (c6) comprises from 6 to 30 carbon atoms, or wherein one or more straight non-alkoxylated aliphatic monoalcohols (c6) are used to prepare the triurethane compound Tb and comprise from 16 to 40 carbon atoms, or wherein a hydrocarbon chain of the monoalcohol (c7) comprises from 6 to 30 carbon atoms, or wherein a hydrocarbon chain of the monoalcohol (c8) comprises from 6 to 30 carbon atoms,, or wherein a hydrocarbon chain of the monoalcohol (c9) comprises from 12 to 30 carbon atoms, or wherein a hydrocarbon chain of the monoalcohol (c10) comprises from 10 to 60 carbon atoms.

10. A method for preparing a triurethane compound T, the method comprising reacting: a. one molar equivalent of at least one polyisocyanate compound (a) comprising on average three isocyanate groups; and b. one molar equivalent of at least one polyalkoxylated compound (b) comprising (b1) a straight aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b2) a branched aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b3) a cycloaliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (b4) a monoaromatic monoalcohol comprising from 6 to 30 polyalkoxylated carbon atoms, and/or (b5) a polyaromatic monoalcohol comprising from 10 to 80 polyalkoxylated carbon atoms, and c. two molar equivalents of at least two identical or different compounds (c) comprising (c1) a straight aliphatic monoalcohol (c1) comprising from 6 to 40 polyalkoxylated carbon atoms, (c2) a branched aliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (c3) a cycloaliphatic monoalcohol comprising from 6 to 40 polyalkoxylated carbon atoms, (c4) a monoaromatic monoalcohol comprising from 6 to 30 polyalkoxylated carbon atoms, (c5) a polyaromatic monoalcohol comprising from 10 to 80 polyalkoxylated carbon atoms, (c6) a straight aliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms, (c7) a branched aliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms, (c8) a cycloaliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms, (c9) a monoaromatic monoalcohol comprising from 6 to 30 non-alkoxylated carbon atoms, and/or (c10) a polyaromatic monoalcohol comprising from 10 to 80 non-alkoxylated carbon atoms.

11. The method of claim 10, which prepares the triurethane compound T of claim 1.

12. Aqueous composition, comprising: the triurethane compound T of claim 1, and optionally an amphiphilic compound; a polysaccharide derivative; a solvent; anti-foaming agent; and/or a biocide agentagents.

13. An aqueous formulation, comprising: the composition of claim 12; and optionally an organic pigment, mineral pigment, organic particles, organo-metallic particles, or mineral particles; and optionally a particle-spacer agent, a dispersing agent, a stabilising steric agent, an electrostatic stabilizer agent, an opacifying agent, a solvent, a coalescing agent, an anti-foaming agent, a preservative agent, a biocide agent, a spreading agent, a thickening agent, a film-forming copolymer, or a mixture thereof.

14. The formulation of claim 13, which is a coating formulation.

15. A concentrated, water-based pigment pulp, comprising: the triurethane compound T of claim 1; and a colored organic or mineral pigment.

16. A method for controlling the viscosity of an aqueous composition, the method comprising: adding at least one of the triurethane compound T of claim 1.

17. The method of claim 16, in which the aqueous composition is a composition comprising the triurethane compound T, and optionally an amphiphilic compound; a polysaccharide derivative; a solvent; anti-foaming agent; and/or a biocide agent.

Description

[0172] The following examples illustrate the various aspects of the invention.

EXAMPLE 1: PREPARATION OF URETHANE COMPOUNDS ACCORDING TO THE INVENTION

Example 1-1: Preparation of a Compound Ta1 According to the Invention

[0173] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump, and a nitrogen inlet and heated by means of a double jacket in which oil circulates, 450.3 g of a dodecanol/tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM = 6,355 Da) is introduced and heated to 90° C. in an inert atmosphere. This product is dehydrated.

[0174] Under stirring and in an inert atmosphere, 12.97 g of HDI isocyanurate (mean MM = 549 g/mol) is then added in one hour in the presence of 200 ppm of a bismuth carboxylate catalyst. When the addition is complete, the reaction mixture is left to stir for 60 minutes at 90° C. ± 1° C. Then, the absence of isocyanate is checked by back titration. 1 g is collected from the reaction medium to which an excess of dibutylamine (1 mol, for example) is added, which reacts with any isocyanate groups that may be present in the medium. Any unreacted dibutylamine is then assayed with hydrochloric acid (1 N, for example). The number of isocyanate groups present in the reaction medium can then be deduced. If this number is not zero, the reaction is continued for 15-minute periods until the reaction is completed. When the level reaches zero, the triurethane compound Ta1 is formulated using a surfactant compound such as ethoxylated alcohol (ethoxylated n-octanol with ten ethylene oxide equivalents), 1,000 ppm of a biocide agent (Biopol SMV Chemipol) and 1,000 ppm of an anti-foaming agent (Tego 1488 Evonik). A composition is obtained consisting of 20% by mass of compound according to the invention, 5% by mass of surfactant and 75% by mass of water.

Example 1-2: Preparation of a Compound Tb1 According to the Invention

[0175] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump, and a nitrogen inlet and heated by means of a double jacket in which oil circulates, 448.7 g of a dodecanol/tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM = 6,355 Da) is introduced and heated to 90° C. in an inert atmosphere. This product is dehydrated.

[0176] Under stirring and in an inert atmosphere, 6.57 g of dodecanol is rapidly added, then 19.38 g of HDI isocyanurate (mean MM = 549 g/mol) is added in one hour in the presence of 200 ppm of a bismuth carboxylate catalyst. When the addition is complete, the reaction mixture is left to stir for 60 minutes at 90° C. ± 1° C. As described in Example 1-1-1, the absence of isocyanate is checked by back titration. If this number is not zero, the reaction is continued for 15-minute periods until the reaction is completed. When the level reaches zero, the triurethane compound Tb1 obtained is formulated using the surfactant compound, the biocide agent and the anti-foaming agent of example 1-1. The composition obtained consists of 20% by mass of compound according to the invention, 5% by mass of surfactant and 75% by mass of water.

Example 1-3: Preparation of a Compound Tb2 According to the Invention

[0177] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump, and a nitrogen inlet and heated by means of a double jacket in which oil circulates, 348.6 g of a dodecanol/tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM = 6,355 Da) and 82.61 g of dodecanol ethoxylated with 30 mol of ethylene oxide (MM=1,506 g/mol) are introduced and heated to 90° C. in an inert atmosphere. These products are dehydrated.

[0178] Under stirring and in an inert atmosphere, 10.20 g of dodecanol is rapidly added, then 30.12 g of HDI isocyanurate (mean MM = 549 g/mol) is added in one hour in the presence of 200 ppm of a bismuth carboxylate catalyst. When the addition is complete, the reaction mixture is left to stir for 60 minutes at 90° C. ± 1° C. As described in Example 1-1, the absence of isocyanate is checked by back titration. If this number is not zero, the reaction is continued for 15-minute periods until the reaction is completed. When the level reaches zero, the triurethane compound Tb2 obtained is formulated in water with the biocide agent and the anti-foaming agent of example 1-1. The composition obtained consists of 20% by mass of compound according to the invention and 80% by mass of water.

Example 1-4: Preparation of a Compound Tc1 According to the Invention

[0179] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump, and a nitrogen inlet and heated by means of a double jacket in which oil circulates, 415.1 g of a dodecanol/tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM = 6,355 Da) is introduced. This product is dehydrated.

[0180] Under stirring and in an inert atmosphere, 24.30 g of dodecanol is rapidly added, then 35.86 g of HDI isocyanurate (mean MM = 549 g/mol) is added in one hour in the presence of 200 ppm of a bismuth carboxylate catalyst. When the addition is complete, the reaction mixture is left to stir for 60 minutes at 90° C. ± 1° C. As described in Example 1-1, the absence of isocyanate is checked by back titration. If this number is not zero, the reaction is continued for 15-minute periods until the reaction is completed. When the level reaches zero, the triurethane compound Tc1 obtained is formulated in water with the biocide agent and the anti-foaming agent of example 1-1. The composition obtained consists of 20% by mass of compound according to the invention and 80% by mass of water.

Example 1-5: Preparation of a Compound Ta2 According to the Invention

[0181] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump, and a nitrogen inlet and heated by means of a double jacket in which oil circulates, 398.9 g of a dodecanol/tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM = 6,355 Da) and of 47.27 g of dodecanol ethoxylated with 30 mol of ethylene oxide (MM=1,506 g/mol) are introduced and heated to 90° C. in an inert atmosphere. This blend is dehydrated.

[0182] Under stirring and in an inert atmosphere, 17.23 g of HDI isocyanurate (mean MM = 549 g/mol) is then added in one hour in the presence of 200 ppm of a bismuth carboxylate catalyst. When the addition is complete, the reaction mixture is left to stir for 60 minutes at 90° C. ± 1° C. As described in Example 1-1, the absence of isocyanate is checked by back titration. If this number is not zero, the reaction is continued for 15-minute periods until the reaction is completed. When the level reaches zero, the triurethane compound Ta2 obtained is formulated using the surfactant compound, the biocide agent and the anti-foaming agent of example 1-1. The composition obtained consists of 20% by mass of compound according to the invention, 5% by mass of surfactant and 75% by mass of water.

Example 1-6: Preparation of a Compound Ta3 According to the Invention

[0183] In a 3 L glass reactor equipped with mechanical stirring rod, a vacuum pump, and a nitrogen inlet and heated by means of a double jacket in which oil circulates, 440.6 g of ethoxylated tristyryl phenol is introduced with 130 mol of ethylene oxide (MM = 6,120 Da) that is heated to 90° C. in an inert atmosphere. This product is dehydrated.

[0184] Under stirring and in an inert atmosphere, 13.17 g of HDI isocyanurate (mean MM = 549 g/mol) is then added in one hour in the presence of 200 ppm of a bismuth carboxylate catalyst. When the addition is complete, the reaction mixture is left to stir for 60 minutes at 90° C. ± 1° C. As described in Example 1-1, the absence of isocyanate is checked by back titration. If this number is not zero, the reaction is continued for 15-minute periods until the reaction is completed. When the level reaches zero, the triurethane compound Ta3 obtained is formulated in water with the biocide agent and the anti-foaming agent of example 1-1. The composition obtained consists of 20% by mass of compound according to the invention and 80% by mass of water.

Example 1-7: Preparation of a Compound Ta4 According to the Invention

[0185] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump, and a nitrogen inlet and heated by means of a double jacket in which oil circulates, 440.6 g of a dodecanol/tetradecanol blend ethoxylated with 130 mol of ethylene oxide (MM = 6,355 Da) is introduced and heated to 90° C. in an inert atmosphere. This product is dehydrated.

[0186] Under stirring and in an inert atmosphere, 13.02 g of HDI biuret (mean MM = 549 g/mol) are then added in one hour in the presence of 200 ppm of a bismuth carboxylate catalyst. When the addition is complete, the reaction mixture is left to stir for 60 minutes at 90° C. ± 1° C. As described in Example 1-1, the absence of isocyanate is checked by back titration. If this number is not zero, the reaction is continued for 15-minute periods until the reaction is completed.

[0187] When the level reaches zero, the triurethane compound Ta4 obtained is formulated using the surfactant compound, the biocide agent and the anti-foaming agent of example 1-1.

[0188] The composition obtained consists of 20% by mass of compound according to the invention, 5% by mass of surfactant and 75% by mass of water.

Example 1-8: Preparation of a Compound Ta5 According to the Invention

[0189] In a 3 L glass reactor equipped with a mechanical stirring rod, a vacuum pump, and a nitrogen inlet and heated by means of a double jacket in which oil circulates, 301.1 g of a dodecanol/tetradecanol blend ethoxylated with 140 mol of ethylene oxide (MM = 6,355 Da) and 142.71 g of dodecanol ethoxylated with 30 mol of ethylene oxide (MM=1,506 g/mol) are introduced and heated to 90° C. in an inert atmosphere. This blend is dehydrated.

[0190] Under stirring and in an inert atmosphere, 26.01 g of HDI isocyanurate (mean MM = 549 g/mol) is then added in one hour in the presence of 200 ppm of a bismuth carboxylate catalyst. When the addition is complete, the reaction mixture is left to stir for 60 minutes at 90° C. ± 1° C. As described in Example 1-1, the absence of isocyanate is checked by back titration. If this number is not zero, the reaction is continued for 15-minute periods until the reaction is completed. When the level reaches zero, the triurethane compound Ta5 obtained is formulated using the surfactant compound, the biocide agent and the anti-foaming agent of example 1-1. The composition obtained consists of 20% by mass of compound according to the invention, 5% by mass of surfactant and 75% by mass of water.

EXAMPLE 2: PREPARATION OF PAINT FORMULATIONS ACCORDING TO THE INVENTION

[0191] Paint formulations F1 to F6 according to the invention are prepared from aqueous compositions of triurethane compound according to the invention. All of the ingredients and proportions (% by mass) used are listed in Table 1.

TABLE-US-00001 Ingredients Quantity (g) Water 99.7 Dispersing agent (Coadis BR3 Coatex) 3.9 Biocide agent (Acticide MBS Thor) 1.3 Anti-foaming agent (Airex 901W Evonik) 1.31 NH.sub.4OH (28%) 0.6 TiO.sub.2 pigment (RHD2 Huntsman) 122.2 CaCO.sub.3pigment (Omyacoat 850 OG Omya) 84.6 Binding agent (Acronal S790 Basf) 270.7 Monopropylene glycol 6.5 Solvent (Texanol Eastman) 6.5 Anti-foaming agent (Tego 825 Evonik) 1 Aqueous composition 1 according to the invention 28.7 Added water q.s.p 650 g total

EXAMPLE 3: CHARACTERISATION OF PAINT FORMULATIONS ACCORDING TO THE INVENTION

[0192] For the paint formulations according to the invention, the Brookfield viscosity, measured at 25° C. and at 10 rpm and 100 rpm (.Math.Bk10 and .Math.Bk100 in mPa.s) was determined 24 hours after their preparation using a Brookfield DV-1 viscometer with RV spindles.

[0193] The properties of the paint formulations are listed in Table 2.

TABLE-US-00002 Formulation Compound .Math..sub.Bk10 .Math..sub.Bk100 F1 Ta1 3 620 2 108 F2 Tb1 7 480 2 956 F3 Ta3 2 050 1 159 F4 Ta5 6 820 3 456 F5 Tc1 14 200 5 355 F6 Ta4 15 900 8 605

[0194] The triurethane compounds according to the invention are highly effective in obtaining excellent low and medium shear gradient viscosities for paint compositions.

EXAMPLE 4 CHARACTERISATION OF PAINT FORMULATIONS ACCORDING TO THE INVENTION

[0195] For the paint formulations according to the invention, the Cone Plan viscosity or ICI viscosity, measured at high shear gradient (.Math.I in mPa.s) was determined 24 hours after their preparation and at room temperature, using a Cone & Plate Research Equipment London (REL) viscometer having a measuring range of 0 to 5 poise, and the Stormer viscosity, measured at medium shear gradient (.Math.S in Krebs Units or KUs), was determined using the reference module of a Brookfield KU-2 viscometer. The properties of the paint formulations are listed in Table 3.

TABLE-US-00003 Formulation Compound .Math..sub.I .Math..sub.s .Math..sub.I/.Math..sub.s F1 Ta1 350 103 3,4 F2 Tb1 315 109 2,9 F3 Ta3 245 87 2,8 F4 Ta5 280 116 2,4

[0196] The triurethane compounds according to the invention make it possible to prepare paint formulations with particularly well-controlled viscosities. In particular, the .Math..sub.I viscosity is particularly high and the .Math..sub.I/.Math..sub.s ratio is therefore excellent. The compounds according to the invention allow for an excellent compromise between high shear gradient viscosity and low shear gradient viscosity.