EP4493609A1 - Copolymère uréthane alkylé épaississant - Google Patents
Copolymère uréthane alkylé épaississantInfo
- Publication number
- EP4493609A1 EP4493609A1 EP23714788.9A EP23714788A EP4493609A1 EP 4493609 A1 EP4493609 A1 EP 4493609A1 EP 23714788 A EP23714788 A EP 23714788A EP 4493609 A1 EP4493609 A1 EP 4493609A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- diisocyanate
- compounds
- formula
- linear
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4833—Polyethers containing oxyethylene units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
Definitions
- the invention relates to a thickening urethane copolymer prepared using a non-alkoxy Guerbet alcohol comprising a doubly branched alkyl group.
- the method for preparing this copolymer and its use in aqueous compositions, in particular in coating compositions, also form part of the invention.
- aqueous hydraulic binder compositions are known, aqueous adhesive compositions, aqueous detergent compositions, aqueous cosmetic compositions, aqueous ink compositions, aqueous paper coating compositions, aqueous coating compositions, in particular aqueous varnish compositions or aqueous paint compositions, for example aqueous decorative paint compositions or aqueous industrial paint compositions.
- these aqueous compositions must have a texture suitable for their use or storage. In particular, they must have a suitable viscosity.
- these aqueous compositions must be able to be used under conditions which can vary widely.
- the viscosity of these aqueous compositions may vary or deteriorate.
- the functional properties of these aqueous compositions can therefore be altered if their rheological behavior is not suitable, for example to prevent sedimentation or phase separation phenomena during storage time, which can also be manifested by variations in viscosity. .
- Such variations or degradations are particularly detrimental or damaging for aqueous hydraulic binder compositions, for aqueous adhesive compositions, for aqueous detergent compositions, for aqueous cosmetic compositions, for aqueous ink compositions, for aqueous coating compositions. of paper, for aqueous coating compositions, in particular for aqueous varnish or paint compositions.
- aqueous compositions which do not present such disadvantages or aqueous compositions which do not lead to such problems.
- aqueous coating compositions in particular aqueous varnish or paint compositions, whose viscosity is adapted to allow their homogeneity to be maintained as well as the integrity of their functional properties. Maintaining viscosity and limiting viscosity loss of these aqueous compositions should be possible over wide ranges of shear gradient.
- aqueous coating compositions use rheology modifying polymers. These polymers should make it possible to give aqueous compositions the desired rheological properties for wide ranges of shear rates. These polymers should also improve the shear thinning of these aqueous compositions by giving them sufficient pseudo-plasticity, ensuring their stability and homogeneity during their storage life, facilitating their transfer to application tools and helping to limit the appearance drips once applied.
- the compatibility of the different constituents of an aqueous coating composition must also be taken into account. In particular, it is important that the thickening copolymer and the pigments and binders used have good compatibility.
- aqueous coating compositions in particular paint compositions and particularly with regard to the addition of pigment concentrates used for coloring.
- pigment compatibility Without good pigment compatibility, the rheology of the composition can be significantly degraded. Insufficient pigment compatibility can also lead to a reduction in color strength and result in an uneven or washed out shade, which may result in the use of a higher quantity of pigment or the presence of aesthetic defects in the final coating.
- Document WO 2019091819 describes an aqueous composition comprising a surfactant compound and a polyurethane polymer prepared from a Guerbet alcohol obtained by condensation of two linear alcohols.
- Document EP 1806386 describes a composition comprising two thickening polymers prepared from a hydrophobic compound obtained by condensation of two linear alcohols.
- Document WO 2022023621 describes diurethane compounds prepared from polyethoxylated Guerbet alcohols.
- Polymers known as thickening agents do not always provide a satisfactory solution to these various problems. There is therefore a need to have improved rheology modifying copolymers.
- the copolymer according to the invention makes it possible to provide a solution to all or part of the problems of polymers of the state of the art.
- the invention provides a copolymer P prepared by at least one polymerization reaction:
- At least one isocyanate compound (a) independently chosen from a diisocyanate compound (al), a polyisocyanate compound (a2) and their combinations;
- - R independently represents a linear C4-C9-alkyl group
- - m independently represents 0 or 1;
- - n independently represents a number ranging from 2 to 7.
- the isocyanate compound (a) is a diisocyanate compound (al) chosen from:
- H12MDI methylene bis (4-cyclohexylisocyanate)
- - symmetrical aliphatic diisocyanate compounds preferably hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI);
- IPDI isophorone diisocyanate
- the compound (al) is chosen from IPDI, HDI, H12MDI and their combinations.
- the isocyanate compound (a) can be a polyisocyanate compound (a2) comprising strictly more than 2 isocyanate functions or more than 2.2 isocyanate functions or even more than 2.5 isocyanate functions. More preferably, the polyisocyanate compound (a2) comprises more than 2.6 isocyanate functions or more than 2.7 isocyanate functions or more than 3 isocyanate functions.
- the polyisocyanate compound (a2) comprises from 2.2 to 6 isocyanate functions, from 2.2 to 4 isocyanate functions, from 2.2 to 3.5 isocyanate functions, from 2.5 to 6 isocyanate functions , from 2.2 to 5 isocyanate functions, from 2.5 to 4 isocyanate functions, from 2.5 to 3.5 isocyanate functions, in particular from 2.6 to 3.3 isocyanate functions.
- the polyisocyanate compound (a2) is chosen from: o triphenylmethane-4,4’,4”-triisocyanate or 1,1’,1”-methylidynetris (4-isocyanatobenzene); o an isocyanurate compound, in particular an isocyanurate compound of a compound chosen from:
- H12MDI methylene bis (4-cyclohexylisocyanate)
- - symmetrical aliphatic diisocyanate compounds preferably hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI); - asymmetric aromatic diisocyanate compounds, preferably:
- trimer compound of biurea in particular a trimer compound of biurea of a compound chosen from:
- m-XDI m-xylylene diisocyanate
- H12MDI methylene bis(4-cyclohexylisocyanate)
- HDI hexamethylene diisocyanate
- PDI pentamethylene diisocyanate
- asymmetric aromatic diisocyanate compounds preferably:
- IPDI isophorone diisocyanate
- compound (a2) is chosen from triphenylmethane-4,4',4”-triisocyanate, 1,1', l”-methylidynetris (4- isocyanatobenzene)
- an HDI isocyanurate an IPDI isocyan
- the polyhydroxy compound (b) is a compound (bl) of formula II:
- - L independently represents an oxyalkylene residue
- the polyhydroxy compound (b) is a compound (bl) of formula II in which:
- - p independently represents a number ranging from 50 to 400, preferably from 100 to 300.
- the polyhydroxy compound (b) is a compound (bl) of formula II in which L independently represents an oxyethylene residue and p independently represents a number ranging from 50 to 400, preferably from 100 to 300.
- the compound (bl) of formula II can be combined with a non-alkoxylated compound (b2) comprising at least three hydroxyl groups.
- the compound (b2) comprises three hydroxyl groups. Much more preferably, it is chosen from glycerol, pentaerythritol and combinations thereof.
- the polyhydroxylated compound (b) can also be polyethoxylated pentaerythritol or a polyalkoxylated compound (b3) comprising at least three hydroxyl groups.
- compound (b3) is different from compound (b2) and comprises three hydroxyl groups.
- compound (b3) is different from compound (b2) and comprises three hydroxyl groups.
- the copolymer P can be prepared using one or more combinations of compounds (bl), (b2) and (b3).
- the compounds (b), (bl) or (b3) independently have a molar mass (Mw) measured by CES ranging from 1,500 to 40,000 g/mol, preferably from 2,000 to 20,000 g/mol. mol, more preferably from 2,000 to 15,000 g/mol or from 2,000 to
- the molar mass of compounds (b), (bl) or (b3) is determined by Size Exclusion Chromatography (CES) or in English “Gel Permeation Chromatography” (GPC).
- CES Size Exclusion Chromatography
- GPC Gel Permeation Chromatography
- This technique uses a “Waters” brand liquid chromatography device equipped with a detector.
- This detector is a “Waters” 2414 type refractometric concentration detector.
- This liquid chromatography equipment is equipped with two steric exclusion columns in order to separate the different molecular weights of the polymers or compounds studied.
- the elution liquid phase is an organic phase composed of THF (HPLC grade, unstabilized).
- the chromatography apparatus also includes an oven which includes a system of columns in series: an “Agilent” PLgel MiniMIX-A type column 250 mm long and 4.6 mm in diameter followed by an “Agilent” type column » PLgel MiniMIX-B 250 mm long and 4.6 mm in diameter.
- the detection system consists of an RI “Waters” 2414 type refractometric detector. The columns are maintained at a temperature of 35°C and the refractometer is brought to a temperature of 35°C.
- the chromatography device is calibrated using polymethyl methacrylate standards certified by the supplier “Agilent” (“EasiVial” PMMA).
- compound (c) is obtained by a dimerization reaction of two compounds of formula I.
- This dimerization is a Guerbet reaction carried out with these two alcohols of formula I.
- the dimerization reaction and its implementation conditions are known as such.
- the Guerbet reaction is generally carried out at high temperature and pressure, in a basic medium and in the presence of a catalyst.
- Compound (c) can be prepared from the same compound of formula I or from two different compounds of formula I.
- the dimerization of two identical compounds of formula I leads to a homodimer (cl).
- compound (c) is a homodimer (cl) obtained by dimerization of two identical compounds of formula I in which:
- - R represents a linear Cs-Cv-alkyl group
- - m represents 0 or 1, preferably 0;
- - n represents a number ranging from 2 to 7.
- compound (c) is a homodimer (cl) obtained by dimerization of two identical compounds of formula I in which
- - R represents a linear C4-C9-alkyl group, preferably a linear C5-C7-alkyl group;
- - m represents 0 or 1, preferably 0;
- - n represents a number ranging from 5 to 7, preferably from 4 to 6, more preferably 4 or 5.
- the dimerization is carried out from two different compounds of formula I and leads to a mixture comprising 2 different homodimers (cl) and a heterodimer (c2).
- a mixture of compounds (c) can be obtained by dimerization of two different compounds of formula I in which:
- - R independently represents a linear Cs-Cv-alkyl group
- - m independently represents 0 or 1, preferably 0;
- - n independently represents a number ranging from 2 to 7.
- a mixture of compounds (c) can be obtained by dimerization of two different compounds of formula I in which
- - R independently represents a linear C4-C9-alkyl group, preferably a linear Cs-Cv-alkyl group;
- - m independently represents 0 or 1, preferably 0;
- - n independently represents a number ranging from 5 to 7, preferably from 4 to 6, more preferably 4 or 5.
- a preferred mixture of compounds (c) comprises a heterodimeric compound (c2) obtained by dimerization of a first compound of formula I in which R represents a linear Cs-alkyl group, m represents 0 and n represents 5 and a second compound different from formula I in which R represents a linear Cv-alkyl group, m represents 0 and n represents 4.
- a particularly preferred mixture of compounds (c) comprises:
- the dimerization carried out from two different compounds of formula I can lead to a mixture consisting of 2 different homodimers (cl) and a heterodimer (c2).
- the quantities of compounds (a), (b) and (c) may vary.
- the polymerization reaction involves:
- the polymerization reaction can carry out:
- the polymerization reaction can use only the compounds (a), (b) and (c) or use one or more other additional compounds. Then, the polymerization reaction can also use at least one hydrophobic compound (d) different from compound (c), preferably chosen from a compound of formula (III):
- - OE independently represents a CH2CH2O group
- - OP independently represents a group chosen from CH(CH3)CH2O and CH 2 CH(CH 3 )O,
- R 1 independently represents a linear or branched Cô-C40-alkyl group, a phenyl group, a polyphenyl group, preferably a linear or branched C10-C30-alkyl group, more preferably a linear C10-C22-alkyl group or branched, or a group comprising 2 to 5 phenyls or a tristyrylphenyl group or a pentastyrylcumylphenyl group, preferably less than 20 mol%, preferably 0.05 to 20 mol%, in particular 0.1 to 10 mol%, of compound (d) relative to the total molar quantity of compounds involved.
- the copolymer P according to the invention can be used in numerous technical fields, in particular as a rheology control agent. It can be incorporated into different compositions.
- the invention provides a rheological control composition comprising at least one copolymer P according to the invention.
- the rheological control composition according to the invention can be treated in an acidic manner leading to a pH less than 8, preferably a pH greater than 6. This treatment can be carried out using an acid, in particular a carboxylic acid such as as acetic acid or lactic acid.
- the rheological control composition according to the invention may also comprise at least one solvent, in particular water or a coalescence solvent, for example glycol, butylglycol, butyldiglycol, monopropyleneglycol, ethyleneglycol, ethylenediglycol, “Dowanol” products including the CAS number is 34590-94-8), “Texanol” products whose CAS number is 25265-77-4); or combined with at least one additive chosen from an amphiphilic compound, in particular a surfactant compound, preferably a hydroxylated surfactant compound, for example alkyl-polyalkylene glycol, in particular alkyl-polyethylene glycol and alkyl-polypropylene glycol; a polysaccharide derivative, for example cyclodextrin, cyclodextrin derivative, polyethers, alkyl glucosides; a hydrotropic compound, an anti-foam agent, a biocidal agent and combinations thereof.
- solvent in particular water or
- the rheological control composition according to the invention is particularly suitable for facilitating the implementation of pigments in an aqueous medium, in particular organic or mineral pigments. It can be incorporated into a particular pigmented formulation.
- the invention provides an aqueous formulation comprising:
- organic or mineral pigment or organic, organo-metallic or mineral particles for example calcium carbonate, talc, kaolin, mica, silicates, silica, metal oxides, in particular titanium dioxide, iron oxides; and eventually
- At least one agent chosen from a particle spacer, a dispersing agent, a steric stabilizing agent, an electrostatic stabilizing agent, an opacifying agent, a coloring agent, a solvent, a coalescing agent, an anti-foaming agent, a preservative, a biocidal agent, a spreading agent, a thickening agent, a film-forming copolymer and mixtures thereof.
- the formulation according to the invention is a coating formulation, in particular an ink formulation, a varnish formulation, an adhesive formulation, a paint formulation, for example decorative paint or industrial paint.
- the copolymer P according to the invention can also be used in the field of printing, in particular textile printing.
- the invention provides a concentrated aqueous pigment paste comprising at least one copolymer P according to the invention and at least one organic or mineral colored pigment.
- the invention also provides a method for controlling the viscosity of an aqueous composition which comprises the addition of at least one copolymer P according to the invention in this composition.
- the viscosity control method according to the invention is implemented for an aqueous composition which is an aqueous formulation according to the invention.
- the advantageous, particular or preferred characteristics of the copolymer P according to the invention define rheological control compositions, aqueous formulations, pigment pastes as well as methods of controlling the viscosity according to the invention which are also advantageous, particular or preferred.
- Example 1 Preparation and characterization of the copolymer (PI) according to the invention:
- a catalyst of the bismuth carboxylate type K Kat B221
- a compound (c) prepared by dimerization by Guerbet reaction of a compound of formula I in which R represents a linear Cs-alkyl group, m represents 0 and n represents 5 and a compound of formula I in which R represents a linear Cv-alkyl group, m represents 0 and n represents 4, non-ethoxylated - “Isofol” 2426S ) (16.4 g) is added in 5 min.
- a diisocyanate compound (al) isophorone diisocyanate, IPDI (9.9 g) is introduced using a syringe with stirring at 150 rpm. The reaction is continued at 100°C for 1 hour.
- a surfactant compound of ethoxylated alcohol type (“Emulan” HE 51 “Basf”) (95 g), 1,000 ppm of a biocidal agent (“Biopol” SMV “Chemipol” ), 1,000 ppm of an anti-foaming agent (“Tego” 1488 “Evonik”) and water (730 g).
- An aqueous composition is obtained consisting of 17.5% by weight of PI copolymer according to the invention, 9.5% by weight of surfactant compound and 73% by weight of water.
- the paint formulation is colored by adding 5% by weight of a black pigment (“Colanyl” N500 black “Clariant”) to obtain the Fl formulation according to the invention.
- a black pigment (“Colanyl” N500 black “Clariant”)
- the pigment compatibility of the Fl formulation is evaluated on a dry paint film.
- the coloring of the initially white paint is obtained by adding 5% of coloring based on black pigment (“Colanyl” N500 black “Clariant”), percentage calculated in relation to the weight of the white paint formulation.
- the test known as such, of rubbing the colored paint with a finger and applied to a wet thickness of 150 micrometers on a contrast card (rub out test) makes it possible to subject a small part of the surface of the paint film freshly applied color with a shearing effect generated by a circular movement of the finger.
- the shearing effect can modify the stability and distribution of the colored pigment in the matrix that constitutes the colored paint film and consequently, the intensity of the coloring at the location of the sheared area.
- the color difference between the zone of the colored paint film initially sheared and the zone of non-sheared colored paint is measured using a spectrophotometer of the spectro-guide sphere gloss type marketed by the company “Byk”.
- the color difference is quantified by the AE value calculated from the measurement parameters corresponding to the known color space L*a*b*.
- a low AE value means a reduced color difference between the sheared zone and the non-sheared zone, and therefore an improvement in pigment compatibility.
- the area of unsheared colored paint is also measured corresponding to one of the parameters of the L*a*b* color space.
- the L* parameter quantifies the intensity of the coloring.
- a low value for the parameter L* means reduced clarity and therefore a greater black intensity corresponding to an improvement in the pigment compatibility of the paint formulation evaluated in which the copolymer according to the invention is used.
- the results are presented in Table 2.
- the copolymer according to the invention makes it possible to control the different components of the viscosity, both after preparation and over time.
- the copolymer according to the invention gives good pigment compatibility to this paint formulation.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR2202412A FR3133612A1 (fr) | 2022-03-18 | 2022-03-18 | Copolymère uréthane alkylé épaississant |
PCT/FR2023/000023 WO2023175247A1 (fr) | 2022-03-18 | 2023-03-10 | Copolymère uréthane alkylé épaississant |
Publications (1)
Publication Number | Publication Date |
---|---|
EP4493609A1 true EP4493609A1 (fr) | 2025-01-22 |
Family
ID=82320094
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP23714788.9A Pending EP4493609A1 (fr) | 2022-03-18 | 2023-03-10 | Copolymère uréthane alkylé épaississant |
Country Status (6)
Country | Link |
---|---|
US (1) | US20250188221A1 (zh) |
EP (1) | EP4493609A1 (zh) |
KR (1) | KR20240161183A (zh) |
CN (1) | CN118891301A (zh) |
FR (1) | FR3133612A1 (zh) |
WO (1) | WO2023175247A1 (zh) |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7803864B2 (en) * | 2006-01-05 | 2010-09-28 | Rohm And Haas Company | Associative thickener compositions and methods of use |
US11713369B2 (en) * | 2017-11-08 | 2023-08-01 | Basf Se | Polymeric additives for reducing the viscosity loss on tinting |
FR3112776B1 (fr) * | 2020-07-27 | 2024-01-12 | Coatex Sas | Composé diuréthane modificateur de rhéologie |
-
2022
- 2022-03-18 FR FR2202412A patent/FR3133612A1/fr active Pending
-
2023
- 2023-03-10 US US18/845,596 patent/US20250188221A1/en active Pending
- 2023-03-10 CN CN202380027781.0A patent/CN118891301A/zh active Pending
- 2023-03-10 EP EP23714788.9A patent/EP4493609A1/fr active Pending
- 2023-03-10 KR KR1020247034843A patent/KR20240161183A/ko active Pending
- 2023-03-10 WO PCT/FR2023/000023 patent/WO2023175247A1/fr active Application Filing
Also Published As
Publication number | Publication date |
---|---|
FR3133612A1 (fr) | 2023-09-22 |
US20250188221A1 (en) | 2025-06-12 |
WO2023175247A1 (fr) | 2023-09-21 |
CN118891301A (zh) | 2024-11-01 |
KR20240161183A (ko) | 2024-11-12 |
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