RHEOLOGY-MODIFYING DIFUNCTIONAL COMPOUND

Abstract

A difunctional compound T prepared by reacting one molar equivalent of at least one dihalogenated compound (a), and two molar equivalents of a same polyalkoxylated compound (b) selected from the group consisting of straight aliphatic monoalcohols (b1), branched aliphatic monoalcohols (b2), cycloaliphatic monoalcohols (b3), monoaromatic monoalcohols (b4), and polyaromatic monoalcohols (b5).

Claims

1. A difunctional compound T prepared by reacting: a. one molar equivalent of at least one dihalogenated compound (a) of formula (I):
L-R.sub.2  (I) wherein R independently represents Cl, Br or I and L independently represents a CH.sub.2 group and b. two molar equivalents of a same polyalkoxylated compound (b) selected from the group consisting of: straight aliphatic monoalcohols (b1) comprising from 6 to 40 polyalkoxylated carbon atoms and comprising from 80 to 500 alkoxylated groups, branched aliphatic monoalcohols (b2) comprising from 6 to 40 polyalkoxylated carbon atoms and comprising from 80 to 500 alkoxylated groups, cycloaliphatic monoalcohols (b3) comprising from 6 to 40 polyalkoxylated carbon atoms and comprising from 80 to 500 alkoxylated groups, monoaromatic monoalcohols (b4) comprising from 6 to 30 polyalkoxylated carbon atoms and comprising from 80 to 500 alkoxylated groups, and polyaromatic monoalcohols (b5) comprising from 10 to 80 polyalkoxylated carbon atoms and comprising from 80 to 500 alkoxylated groups.

2. The difunctional compound T according to claim 1, comprising a single compound (a) or two or three different compounds (a).

3. The difunctional compound T according to claim 1, wherein dihalogenated compound (a) is a compound of formula (I) wherein R independently represents Br or I.

4. The difunctional compound T according to claim 3, wherein compound (a) is selected from the group consisting of dibromomethane, diiodomethane and combinations thereof.

5. The difunctional compound T according to claim 1: wherein a degree of polyalkoxylation is between 100 and 502, or wherein the polyalkoxylated compound (b) comprises from 100 to 500 alkoxylated groups, or wherein the alkoxylated groups are selected from the group consisting of oxyethylene (—CH.sub.2CH.sub.2O—), oxypropylene (—CH.sub.2CH(CH.sub.3)O— or —CH(CH.sub.3)CH.sub.2O—), oxybutylene (—CH(CH.sub.2CH.sub.3)CH.sub.2O— or —CH.sub.2CH(CH.sub.2CH.sub.3)O—) and combinations thereof.

6. The difunctional compound T according to claim 1, wherein a hydrocarbon chain of the straight aliphatic monoalcohol (b1) comprises from 6 to 30 carbon atoms, a hydrocarbon chain of the branched aliphatic monoalcohol (b2) comprises from 6 to 30 carbon atoms, or a hydrocarbon chain of the cycloaliphatic monoalcohol (b3) comprises from 6 to 30 carbon atoms, or a hydrocarbon chain of the monoaromatic monoalcohol (b4) comprises from 12 to 30 carbon atoms or a hydrocarbon chain of the polyaromatic monoalcohol (b5) comprises from 10 to 60 carbon atoms.

7. A method for preparing a difunctional compound T, comprising reacting: a. one molar equivalent of at least one dihalogenated compound (a) of formula (I):
L-R.sub.2  (I) wherein R independently represents Cl, Br or I and L independently represents a CH.sub.2 group and b. two molar equivalents of a same polyalkoxylated compound (b) selected from the group consisting of: straight aliphatic monoalcohols (b1) comprising from 6 to 40 polyalkoxylated carbon atoms and comprising from 80 to 500 alkoxylated groups, branched aliphatic monoalcohols (b2) comprising from 6 to polyalkoxylated carbon atoms and comprising from 80 to 500 alkoxylated groups, cycloaliphatic monoalcohols (b3) comprising from 6 to 40 polyalkoxylated carbon atoms and comprising from 80 to 500 alkoxylated groups, monoaromatic monoalcohols (b4) comprising from 6 to 30 polyalkoxylated carbon atoms and comprising from 80 to 500 alkoxylated groups, and polyaromatic monoalcohols (b5) comprising from 10 to 80 polyalkoxylated carbon atoms and comprising from 80 to 500 alkoxylated groups.

8. The method according to claim 7 wherein the reacting comprises a single compound (a) or two or three different compounds (a).

9. An aqueous composition comprising: at least one difunctional compound T according to claim 1 and at least one additive selected from the group consisting of an amphiphilic compound, a polysaccharide derivative, a solvent, an anti-foaming agent, and a biocide.

10. An aqueous formulation comprising: at least one aqueous composition according to claim 9; at least one organic or mineral pigment or organic, organo-metallic or mineral particles, and at least one agent selected from the group consisting of a particle-spacer agent, a dispersing agent, a stabilising steric agent, an electrostatic stabilising agent, an opacifying agent, a solvent, a coalescing agent, an anti-foaming agent, a preservative agent, a biocide, a spreading agent, a thickening agent, a film-forming copolymer and mixtures thereof.

11. The aqueous formulation according to claim 10, wherein the aqueous formulation is an ink formulation, a varnish formulation, an adhesive formulation, or a paint formulation.

12. A concentrated aqueous pigment pulp comprising at least one difunctional compound T according to claim 1 and at least one coloured organic or mineral pigment.

13. A method for controlling a viscosity of an aqueous composition comprising adding at least one difunctional compound T according to claim 1 to the aqueous composition.

14. A method for controlling a viscosity of the aqueous composition according to claim 9, comprising adding the at least one difunctional compound T to the aqueous composition.

Description

EXAMPLES

Example 1: Preparation of Difunctional Compounds According to the Invention

Example 1-1: Preparation of a Compound T1 According to the Invention

[0064] In a 3 L glass reactor equipped with mechanical stirring, a vacuum pump, a nitrogen inlet and heated by means of a double jacket in which oil circulates, 452.3 g of ethoxylated dodecanol are introduced with 140 mol of ethylene oxide (MM=6,355 Da) that is heated to 80° C. in an inert atmosphere. 5.69 g of sodium hydroxide are added and the medium is kept stirred for 2 hours.

[0065] 6.18 g (MM=173.8 g/mol) of dibromomethane are then added in one hour. After the addition is completed, the reaction mixture is left to stir for 60 minutes at 100° C.±1° C. The compound T1 obtained is formulated in water with the addition of 1,000 ppm of a biocide (Biopol SMV Chemipol) and of 1,000 ppm of an anti-foaming agent (Tego 1488 Evonik). A composition 1 is obtained consisting of 20% by mass of compound T1 according to the invention and 80% by mass of water.

Example 1-2: Preparation of a Compound T2 According to the Invention

[0066] In a 3 L glass reactor equipped with mechanical stirring, a vacuum pump, a nitrogen inlet and heated by means of a double jacket in which oil circulates, 451.0 g of ethoxylated tristyrylphenol are introduced with 130 mol of ethylene oxide (MM=6,120 Da) that is heated to 80° C. in an inert atmosphere. 5.90 g of sodium hydroxide are added and the medium is kept stirred for 2 hours.

[0067] 6.40 g (MM=173.8 g/mol) of dibromomethane are then added in one hour. After the addition is completed, the reaction mixture is left to stir for 60 minutes at 100° C.±1° C. The compound T2 obtained is formulated in water with the addition of 1,000 ppm of a biocide (Biopol SMV Chemipol) and of 1,000 ppm of an anti-foaming agent (Tego 1488 Evonik). A composition 2 is obtained consisting of 20% by mass of compound T2 according to the invention and 80% by mass of water.

Example 2: Preparation of Paint Formulations According to the Invention

[0068] A paint formulation F1 according to the invention is prepared from aqueous composition 1 of difunctional compound T1 according to the invention. All of the ingredients and proportions (% by mass) used are listed in Table 1.

TABLE-US-00001 TABLE 1 Ingredients Amount (g) water 99.7 dispersing agent (Coadis BR3 Coatex) 3.9 biocide (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.3 pigment (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) 1.0 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

[0069] For the paint formulation according to the invention, the Brookfield viscosity, measured at 25° C. and at 10 rpm and 100 rpm (μ.sub.Bk10 and μ.sub.Bk100 in mPa.Math.s) was determined 24 hours after its preparation using a Brookfield DV-1 viscometer with RVT spindles. The properties of the paint formulation are listed in Table 2.

TABLE-US-00002 TABLE 2 Formulation Compound μ.sub.BK10 μ.sub.BK100 F1 T1 1,370 890

[0070] The difunctional 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

[0071] For the paint formulation according to the invention, the Cone Plan viscosity or ICI viscosity, measured at high shear gradient (μI in mPa.Math.s) was determined 24 hours after its preparation and at room temperature, using a Cone & Plate Research Equipment London (REL) viscometer with a measuring range of 0 to 5 poise, and the Stormer viscosity, measured at medium shear gradient (μS in Krebs Units or KUs), was determined using the reference module of a Brookfield KU-2 viscometer. The properties of the paint formulation are listed in Table 3.

TABLE-US-00003 TABLE 3 Formulation Compound μI μS μI/μS F1 T1 170 81 2.1

[0072] The difunctional compounds according to the invention make it possible to prepare paint formulations with particularly well-controlled viscosities. In particular, the μ.sub.I viscosity is particularly high and the μ.sub.r/μ.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.