WO2002102868A1 - Epaississants non ioniques pour compositions pigmentaires, notamment pour peintures, et leurs applications - Google Patents
Epaississants non ioniques pour compositions pigmentaires, notamment pour peintures, et leurs applications Download PDFInfo
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- WO2002102868A1 WO2002102868A1 PCT/FR2002/001939 FR0201939W WO02102868A1 WO 2002102868 A1 WO2002102868 A1 WO 2002102868A1 FR 0201939 W FR0201939 W FR 0201939W WO 02102868 A1 WO02102868 A1 WO 02102868A1
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Classifications
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- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
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- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33348—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing isocyanate group
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
Definitions
- the present invention relates to the technical sector of pigment compositions and in particular pigment compositions for paints and similar compositions, and even more precisely pigment bases for paints intended for coloring.
- the rheological profile of the composition or base comes into play, the base being the aqueous composition charged with white color, base of the colored pigment composition. or pigmented.
- This white charged and / or pigmented aqueous composition is formed from a liquid phase which may be water or an organic solvent miscible with water or a mixture of the two, one or more polymers in suspension in the liquid phase called “binders”, fillers and / or pigments, of at least one agent dispersing fillers and / or pigments which may be a water-soluble polymer or copolymer, adjuvants as diverse as coalescing agents, biocides , anti-foaming agents or the like, and finally at least one thickening agent which is a natural or synthetic polymer or copolymer.
- a liquid phase which may be water or an organic solvent miscible with water or a mixture of the two, one or more polymers in suspension in the liquid phase called “binders”, fillers and / or pigments, of at least one agent dispersing fillers and / or pigments which may be a water-soluble polymer or copolymer, adjuvants as diverse as coalescing agents, biocides , anti
- the rheological profile is well known to those skilled in the art, and is represented by the curve of the viscosity ⁇ as a function of the speed gradient D.
- composition is a measure of the pressure applied to the composition or to the base (Unless otherwise specified, the term “composition” will be used in the following to designate any composition, or any base for paint or the like, aqueous loaded and / or pigmented as defined above).
- the application will cause a dissociation or heterogeneity of the composition, and therefore areas of different color density, for example less dense streaks in color, which is obviously not the aim.
- compositions for painting (together below, including in the claims, as already indicated, “compositions”) having very good compatibility with pigment dyes, as well on matt paints than on satin paints.
- the invention aims in particular to provide compositions which ensure excellent pigment compatibility and have a high viscosity at low and medium shear gradient also called speed gradient, both on matt paints and on satin paints, that is to say -to say in particular in a range of speed gradient D between:
- the white bases contain, as is known to those skilled in the art, fillers such as carbonates, in particular calcium, a titanium oxide, kaolin, and similar well-known fillers, which can be used according to the invention.
- fillers such as carbonates, in particular calcium, a titanium oxide, kaolin, and similar well-known fillers, which can be used according to the invention.
- Pigment dyes are also well known to those skilled in the art, and are for example chosen from carbon black, phthalocyanine blue, iron oxides
- the test consists in applying a layer of paint to a support without shearing, that is to say slowly and without stress, then in applying a shearing by a rotary movement of a finger applied to said layer of paint.
- the intensity of color on the area rubbed by the finger will remain constant or "homogeneous" with respect to the area not rubbed; otherwise, the rubbed area will exhibit heterogeneity in color intensity compared to the untreated area.
- This heterogeneity will be expressed by a colorimetric difference measured using a spectro-colorimeter called Spectro-pen TM.
- Polyurethane thickeners are also known which make it possible to obtain, in an aqueous paint, high viscosities under a high speed gradient but which are not capable of developing high Brookfield TM viscosities.
- these products are functionalized with short ends of the hydrocarbon chain, that is to say comprising less than 14 carbon atoms.
- These compounds have the advantage of retaining a certain pigmentary compatibility but do not make it possible to obtain high Brookfield TM viscosities under a low shear gradient.
- polyurethanes are known which develop high Brookfield TM viscosities under a low shear gradient (Synthesis and Characterization of Model Associative Polymers, Richard D. Jenkins, David R. Bassett, César A. Silebi and Mohamed S. El-Aasser , J. of Applied Polymer Science, vol. 58, p 209-230 (1995); Polymeric Mat. Sci. And Engineering, vol. 59, p 1033 (1988); Polymeric Mat. Sci. And
- the invention aims in particular to provide compositions which ensure excellent pigment compatibility and exhibit a high viscosity at low and medium shear gradient, both on matt paints and on satin paints, and do not exhibit the drawbacks linked to the use of so-called ionic acrylic copolymers, namely the obligation to carry out the formulation at a pH greater than 7, their poor resistance to water, or their low propensity to spread, or finally their very high sensitivity to salts.
- the invention therefore aims to solve a particularly difficult problem often encountered by the user.
- compositions in the general sense given above, and in particular white bases, in particular for paint
- compositions having simultaneously a high Brookfield TM viscosity at low shear gradient and excellent pigment compatibility, both on matt and satin paints.
- Brookfield TM viscosity at low shear gradient and excellent pigment compatibility both on matt and satin paints.
- the invention not only provides a solution to this problem, but also proposes thickeners which are better thickeners than those of the prior art.
- the invention relates in its general principle to molecules which are thickeners having the above properties, and which are of the polymer type with an alkylene oxide chain, in particular ethylene oxide (EO) or ethylene oxide and propylene oxide (OP) characterized in that they are based on polyisocyanate and in particular diisocyanate units and comprise at the chain end hydrocarbon groups themselves comprising at least three substituted or unsubstituted aromatic rings .
- EO ethylene oxide
- OP ethylene oxide
- thickeners are already known having hydrocarbon groups at the chain end, these groups having fairly long chain lengths and sometimes aromatic or cyclic groups, but the invention was able to define the above selection criteria.
- These thickeners are non-ionic.
- the invention relates in particular to thickeners corresponding to formula (I) below:
- DI is a di-isocyanate group such as toluene di-isocyanate, isophorone diisocyanate or hexamethylene di-isocyanate
- PEG is a polyethylene glycol group of molecular weight ranging from 6000 to 20,000, n is between 1 and 40, x, z, x ', z is between 1 and 40, y, y' is between 0 and 40 , with x + y + z + x '+ y' + z 'between 2 and 80.
- the molecular weight of the PEG is between 6,000 and 15,000, preferably close to 10,000.
- n is close to 1.
- R or R ' are hydrocarbon groups comprising at least three aromatic rings, substituted or not, and are different or identical.
- the associative polymers are not suitable: for example, a product functionalized with a group having 8 carbon atoms, which is a pure associative, certainly gives suitable pigment compatibility, but it does not is not a suitable thickener, by far, low or medium shear gradient.
- the group R will be a tristyrylphenyl group (TSP) of formula:
- the group R will be a distyrylphenyl group (DSP) of formula:
- the group R is substituted.
- the substituents of the group R are preferably chosen from the groups: phenyls, benzyls or linear or branched alkyls containing any number of carbon atoms. According to another preferred embodiment, the one or more substituents are placed on the aromatic groups, themselves optionally substituted.
- one of the phenyl groups of the TSP group is itself substituted by at least one phenyl group.
- An interesting case according to the invention is that where one of the styryl groups of the TSP group is itself substituted by a styryl group, the R group then being a tetrasty rylpheny le group.
- the invention also relates to the use of the compound according to the invention as a thickener for aqueous, charged and / or pigmented, white or colored compositions.
- the invention finally relates to the aqueous compositions, charged and / or pigmented, white or colored, containing the thickening compound according to the invention.
- the thickening compound according to the invention is introduced into said compositions in an amount of 0.1% to 2.0%, preferably in an amount of 0.2% to 1.0%, amount expressed in percent by dry weight relative to the total mass of the composition.
- compositions according to the invention are characterized in that they contain the thickening copolymer according to the invention, preferably in an amount of 0.1% to 2.0%, and very preferably at a rate of 0.2% to 1.0%, quantity expressed in percent by dry weight relative to the total mass of the composition.
- Brookfield TM viscosity measurements are commonly used, well known to those skilled in the art.
- the “low” shear gradient measurements correspond to velocities of the device set at 10 and 100 revolutions / minute.
- Brookfield TM viscosity measurements are carried out after 24 hours of storage at rest, 1 week of storage at rest and 1 month of storage at rest.
- the Stormer viscosity measurement is also used (expressed in Krebs “KU” units). These measures are also well known to those skilled in the art. This Stormer viscosity applies to measurements with an “average” shear gradient.
- the aqueous, charged and / or pigmented, white or colored compositions according to the invention are characterized in that they contain the thickening copolymer according to the invention, preferably in an amount of 0.1% to 2.0%, and very preferably at a rate of 0.2% to 1.0%, quantity expressed in percent by dry weight relative to the total mass of the composition, and in that the value of the sum of the ratings ( ⁇ E mate + ⁇ Esatiêt + ⁇ mate + ⁇ s tinée) is greater than or equal to 3 and very preferably equal to 4, with the following notations, namely:
- Brookfield TM viscosity after 24 hours (denoted ⁇ s tinée) at 10 rpm. is greater than or equal to 2000 mPa.s, 0, if the Brookfield TM viscosity after 24 hours (noted ⁇ its tin e ee) at 10 rpm. is between 800 inclusive and 2,000 mPa.s excluded,
- the determination of the value of Delta E ( ⁇ E) of the matt or satin colored aqueous formulation is carried out by adding, to the white base, 5% by weight of black pigment, that is to say 10 g. of black pigment (COLANYL TM Black marketed by CLARIANT) in 190 g. of white paint.
- black pigment COLANYL TM Black marketed by CLARIANT
- This test consists in applying without shearing, using a filmograph, 150 micrometers of the formulation of the colored matt or satin paint to be tested on a contrast card, that is to say slowly and without constraint and at wait
- the color difference between the sheared area (area rubbed) and the non-sheared area (area of the film not rubbed) determined by means of the spectro-colorimeter called Spectro-pen makes it possible to evaluate (value of ⁇ E) whether or not the paint composition tested has good pigmentary compatibility.
- the purpose of this example is to demonstrate the rheological and pigmentary compatibility properties provided by the thickening agents according to the invention for paint formulations, matt, with solvent and at constant dosage.
- paint formulations include the ingredients and additives listed in the first part of Tables 1a, 1b and the components of the white base, and which the person skilled in the art will recognize.
- COATEX P 90 designates a polyacrylate dispersant marketed by the company COATEX under the brand name COATEX P 90.
- Monoethylene glycol is a coalescing agent.
- the Mergal K6N TM product designates a biocidal agent sold by the company TROY.
- the TiO 2 RL 68 product is a titanium oxide sold by the company MILLENNIUM.
- the Hydrocarb TM product is a known fine filler of the natural CaCO 3 type, marketed by the OMYA group.
- the Durcal TM product is a coarser filler, also known, of the natural CaCO 3 type, marketed by the OMYA group.
- Rhodopas DS 910 TM is a styrene-acrylic binder sold by the company RHODIA.
- the product "White spirit” is a well-known petroleum cut which has a solvent function.
- the above-mentioned matt paint formulation was prepared in which the thickening agent to be tested is added.
- L determined by the implementation of the Spectro-pen TM spectro-colorimeter, measures the whiteness of the formulation applied to the contrast card. The closer the values are to 100, the worse the compatibility. This value is for illustrative purposes only.
- This test illustrates the prior art and uses 0.57% by dry weight, relative to the total weight of the formulation, of a well known polyurethane based on the condensation product of an alcohol containing 16 carbon atoms. , toluene diisocyanate and polyethylene glycol with a molecular weight of 10,000.
- DI isophorone di-isocyanate
- DI isophorone di-isocyanate
- Test No. 7 This test illustrates the invention and uses 0.57% by dry weight, relative to the total weight of the formulation, of a compound of formula (I) in which: DI is isophorone di -isocyanate,
- DI isophorone di-isocyanate
- DI isophorone di-isocyanate
- This test illustrates a field outside the invention and uses 0.57% by dry weight, relative to the total weight of the formulation, of a compound of formula (I) in which: DI is isophorone di-isocyanate,
- This test illustrates a field outside the invention and uses 0.57% by dry weight, relative to the total weight of the formulation, of a compound of formula (I) in which: DI is isophorone di-isocyanate,
- This test illustrates a field outside the invention and uses 0.57% by dry weight, relative to the total weight of the formulation, of a compound of formula (I) in which: DI is isophorone di-isocyanate,
- DI isophorone di-isocyanate
- PEG is a polyethylene glycol with molecular weight equal to 6000
- n l
- DI isophorone di-isocyanate
- PEG is a polyethylene glycol with molecular weight equal to 8000
- n l
- DI isophorone di-isocyanate
- Pigment compatibility (addition of 5% by weight of black pigment paste)
- Pigment compatibility (addition of 5% by weight of pigment paste nos)
- the notation ⁇ ma te is equal to + 1 and the notation ⁇ E ma te is equal to + 1 giving a total ( ⁇ Emate + ⁇ mate) equal to + 2.
- the notation ⁇ mat e is equal to + 1 and the notation ⁇ E ma te is equal to + 1 giving a total ( ⁇ E mate + ⁇ a te) equal to + 2.
- the notation ⁇ mate is equal to + 1 and the notation ⁇ E m te is equal to + 1 giving a total ( ⁇ E mat e + ⁇ m ate) equal to + 2.
- the notation ⁇ mate is equal to 0 and the notation ⁇ E ma te is equal to + 1 giving a total ( ⁇ E ma te + mate) equal to + 1.
- the purpose of this example is to demonstrate the rheological and pigmentary compatibility properties provided by the thickening agents according to the invention for paint formulations, satin, with solvent and at constant dosage.
- paint formulations include the ingredients and additives listed in the first part of Tables 2a, 2b and 2c, which constitute the white base, and which the person skilled in the art will recognize.
- COATEX BR3 designates a polyacrylate dispersant marketed by the company COATEX under the brand name COATEX BR3.
- - Tego 1488 designates an anti-foaming agent sold by the company TEGO.
- - MPG designates monopropylene glycol which is a coalescing agent.
- the Mergal K6N TM product designates a biocidal agent sold by the company TROY.
- the Hydrocarb TM product is a known fine filler of the natural CaCO 3 type, marketed by the OMYA group.
- the TiO 2 RHD2 product is a titanium oxide sold by the company ELEMENTIS.
- Acronal 290D TM is a styrene-acrylic binder sold by the company BASF.
- This test illustrates the prior art and uses 0.22% by dry weight, relative to the total weight of the formulation, of a well known polyurethane based on the product of condensation of an alcohol containing 16 carbon atoms, of toluene di-isocyanate and of polyethylene glycol of molecular weight equal to 10,000.
- DI isophorone di-isocyanate
- DI isophorone di-isocyanate
- DI isophorone di-isocyanate
- DI isophorone di-isocyanate
- PEG is a polyethylene glycol with a molecular weight equal to 10,000
- n l
- DI isophorone di-isocyanate
- PEG is a polyethylene glycol with a molecular weight equal to 10,000
- n l
- Test No. 34 This test illustrates a field outside the invention and uses 0.22% by dry weight, relative to the total weight of the formulation, of a compound of formula (I) in which: DI is isophorone diisocyanate,
- DI isophorone di-isocyanate
- DI isophorone di-isocyanate
- DI isophorone di-isocyanate
- Test No. 41 This test illustrates the invention and uses 0.22% by dry weight, relative to the total weight of the formulation, of a compound of formula (I) in which:
- DI isophorone di-isocyanate
- Test No. 42 This test illustrates the invention and uses 0.22% by dry weight, relative to the total weight of the formulation, of a compound of formula (I) in which:
- DI isophorone di-isocyanate
- DI isophorone di-isocyanate
- Pigment compatibility (addition of 5% by weight of black pigment paste)
- Pigment compatibility (addition of 5% by weight of black pigment paste)
- Reading tables 2a, 2b and 2c makes it possible to assign the notations ⁇ E sa tiné and ⁇ sa tiné to the various tests.
- Example 3 The sum of the totals of the notations of Example 1 relating to matt paints and of Example 2 relating to satin paints is collated in Table 3 below.
- Reading Table 3 shows that only the polyurethanes functionalized with groups containing at least three aromatic rings, that is to say that only compounds corresponding to formula (I) in which R and R 'are groups hydrocarbons comprising at least three substituted or unsubstituted aromatic cycles, make it possible to develop viscosities under a low significant shear gradient without losing pigment compatibility, this property being preserved whether it is a matt paint or a satin paint.
- Tests n ° 1-23, 10-32, 11-33, 12-34, 13-35, 14-36, 15-37, 16-38 and 18-40 do not allow to reach the strictly defined criteria (total notations less than 3) whereas the tests of the invention n ° 2-24, 3-25, 4-26, 5-27, 6-28, 7-29, 8-30, 9-31, 17- 39, 19-41, 20-42, 21-43, and 22-44 meet these criteria (total ratings greater than or equal to 3).
- the purpose of this example is to demonstrate the rheological and pigmentary compatibility properties provided by the thickening agents according to the invention for formulations for matt paints, with solvent at variable dosage and constant rheology.
- Test No. 46 This test illustrates the invention and uses 0.75% by dry weight, relative to the total weight of the formulation, of a compound of formula (I) in which: DI is toluene di- isocyanate
- DI isophorone di-isocyanate
- Reading Table 4 allows the ratings ⁇ E mate and ⁇ ma te to be assigned to the various tests.
- the notation ⁇ ma te is equal to 0 and the notation ⁇ E ma te is equal to + 1 giving a total ( ⁇ E mate + ⁇ m ate) equal to + 1; for test no. 46: the notation ⁇ raa te is equal to 0 and the notation ⁇ E ma te is equal to + 1 giving a total ( ⁇ E mate + ⁇ m ate) equal to + 1; for test no.
- the notation ⁇ ma t e is equal to 0 and the notation ⁇ E ma te is equal to + 1 giving a total ( ⁇ E mate + ⁇ m ate) equal to + 1; for test n ° 48: the notation ⁇ ma te is equal to + 1 and the notation ⁇ E ma te is equal to + 1 giving a total ( ⁇ E mate + ⁇ mate) equal to + 2;
- the purpose of this example is to demonstrate the rheological and pigment compatibility properties provided by the thickening agents according to the invention for formulations for satin paint, with variable dosage solvent and constant rheology.
- DI hexaméfhylène di-isocyanate
- Test No. 50 This test illustrates the invention and uses 0.12% by dry weight, relative to the total weight of the formulation, of a compound of formula (I) in which: DI is toluene di- isocyanate
- DI isophorone di-isocyanate
- DI isophorone di-isocyanate
- PEG is a polyethylene glycol with a molecular weight equal to 10,000
- n l
- Reading Table 5 allows the ratings ⁇ E mate and ⁇ m at e to be assigned to the various tests.
- Example 6 The sum of the totals of the notations of Example 3 relating to matt paints and of Example 4 relating to satin paints is collated in Table 6 below:
- Reading Table 6 makes it possible to see that the compounds according to the invention make it possible to reach the criteria strictly defined for different doses and more particularly for doses varying from 0.1% to 2% by dry weight of said thickening compound relative to to the total mass of the composition.
- the invention also covers all the embodiments and all the applications which will be directly accessible to those skilled in the art on reading the present application, their own knowledge, and possibly simple routine tests.
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MXPA03010238A MXPA03010238A (es) | 2001-06-19 | 2002-06-06 | Espesantes no ionicos para composiciones pigmentarias, especialmente para pinturas y sus aplicaciones. |
DK02748940.0T DK1425325T3 (da) | 2001-06-19 | 2002-06-06 | Ikke-ioniske fortykningsmidler til pigmentsammensætninger, især malinger, og anvendelser deraf |
EP02748940.0A EP1425325B1 (fr) | 2001-06-19 | 2002-06-06 | Epaississants non ioniques pour compositions pigmentaires, notamment pour peintures,et leurs applications |
CA2446454A CA2446454C (fr) | 2001-06-19 | 2002-06-06 | Epaississants non ioniques pour compositions pigmentaires, notamment pour peintures, et leurs applications |
US10/480,251 US7217761B2 (en) | 2001-06-19 | 2002-06-06 | Non-ionic thickeners for pigment compositions, in particular for paints and applications thereof |
ES02748940.0T ES2498367T3 (es) | 2001-06-19 | 2002-06-06 | Espesantes no iónicos para composiciones pigmentarias, especialmente para pinturas y sus aplicaciones |
KR1020037016513A KR100969261B1 (ko) | 2001-06-19 | 2002-06-06 | 안료 조성물, 특히 페인트용 안료 조성물을 위한 비이온성점증제 및 이것의 용도 |
US11/590,779 US20070066752A1 (en) | 2001-06-19 | 2006-11-01 | Non-ionic thickeners for pigment compositions, in particular paints and applications thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR01/08062 | 2001-06-19 | ||
FR0108062A FR2826014B1 (fr) | 2001-06-19 | 2001-06-19 | Epaississants non ioniques pour compositions pigmentaires, notamment pour peintures, assurant la compatibilite pigmentaire, et leurs applications |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/590,779 Continuation US20070066752A1 (en) | 2001-06-19 | 2006-11-01 | Non-ionic thickeners for pigment compositions, in particular paints and applications thereof |
Publications (1)
Publication Number | Publication Date |
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WO2002102868A1 true WO2002102868A1 (fr) | 2002-12-27 |
Family
ID=8864520
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2002/001939 WO2002102868A1 (fr) | 2001-06-19 | 2002-06-06 | Epaississants non ioniques pour compositions pigmentaires, notamment pour peintures, et leurs applications |
Country Status (9)
Country | Link |
---|---|
US (2) | US7217761B2 (fr) |
EP (1) | EP1425325B1 (fr) |
KR (1) | KR100969261B1 (fr) |
CA (1) | CA2446454C (fr) |
DK (1) | DK1425325T3 (fr) |
ES (1) | ES2498367T3 (fr) |
FR (1) | FR2826014B1 (fr) |
MX (1) | MXPA03010238A (fr) |
WO (1) | WO2002102868A1 (fr) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011030197A2 (fr) | 2009-09-10 | 2011-03-17 | Coatex S.A.S. | Polyurethanes associatifs a base de cardanol, epaississants associatifs correspondants et leurs utilisations |
WO2011104599A1 (fr) | 2010-02-26 | 2011-09-01 | Coatex S.A.S. | Monomere associatif a base d'alcools oxo, polymere acrylique contenant ce monomere, utilisation dudit polymere comme epaississant dans une formulation aqueuse, formulation obtenue |
WO2011104600A1 (fr) | 2010-02-26 | 2011-09-01 | Coatex S.A.S. | Emulsion acrylique associative contenant un monomere a base d'alcool oxo, son procede de fabrication et procede d'epaississement d'une formulation aqueuse a partir de cette emulsion |
WO2012172248A1 (fr) | 2011-06-14 | 2012-12-20 | Coatex | Epaississants non ioniques associatifs contenant des alkyls cyclohexylols, formulations les contenant et leurs utilisations |
WO2012172249A1 (fr) | 2011-06-14 | 2012-12-20 | Coatex | Epaississants non ioniques associatifs contenant des alkyls cyclohexylols, formulations les contenant et leurs utilisations |
WO2013072617A1 (fr) | 2011-11-18 | 2013-05-23 | Coatex | Epaississants ioniques associatifs contenant des alkyls cyclohexylols alkoxyles, leurs utilisations et formulations les contenant |
WO2013072592A2 (fr) | 2011-11-18 | 2013-05-23 | Coatex | Épaississants non ioniques associatifs contenant des alkyls cyclohexylols alkoxyles, leurs utilisations et formulations les contenant |
FR3014874A1 (fr) * | 2013-12-16 | 2015-06-19 | Coatex Sas | Agent epaississant hydrosoluble pour systemes aqueux, formulations le contenant et utilisations |
WO2016097647A1 (fr) | 2014-12-19 | 2016-06-23 | Coatex | Agent epaississant pour systemes aqueux, formulations le contenant et utilisations |
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FR2826014B1 (fr) * | 2001-06-19 | 2007-04-13 | Coatex Sas | Epaississants non ioniques pour compositions pigmentaires, notamment pour peintures, assurant la compatibilite pigmentaire, et leurs applications |
US7803864B2 (en) | 2006-01-05 | 2010-09-28 | Rohm And Haas Company | Associative thickener compositions and methods of use |
US7906577B2 (en) * | 2008-01-18 | 2011-03-15 | Rhodia Operations | Latex binders, aqueous coatings and paints having freeze-thaw stability and methods for using same |
FR2931161B1 (fr) | 2008-05-14 | 2010-04-23 | Coatex Sas | Utilisation d'un couple dispersant acrylique-epaississant associatif dans une peinture alkyde pour ameliorer la retention du niveau de brillant |
FR2933098B1 (fr) * | 2008-06-26 | 2010-08-20 | Coatex Sas | Utilisation comme agents epaississants pour peinture aqueuse de polyethers a base d'epoxyde d'alpha olefines ou de glycidyl ether en presence de tensio-actifs |
CN107109087A (zh) * | 2014-12-19 | 2017-08-29 | 威士伯采购公司 | 含有流变改性剂的涂料组合物 |
AU2017239546B2 (en) | 2016-10-21 | 2022-01-13 | Rohm And Haas Company | Deep base paint formulation |
BR102020001678A2 (pt) | 2019-02-15 | 2020-09-15 | Rohm And Haas Company | Polímero de óxido de alquileno capeado com um copolímero em bloco de alcoxilato de éter arílico |
CN109880038B (zh) * | 2019-03-05 | 2021-09-28 | 广州浦利姆环保科技有限公司 | 水性聚氨酯及其制备方法、水性色浆 |
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US4079028A (en) * | 1975-10-03 | 1978-03-14 | Rohm And Haas Company | Polyurethane thickeners in latex compositions |
JPH0364309A (ja) * | 1989-08-01 | 1991-03-19 | Toray Ind Inc | ブロックドポリイソシアネート分散液 |
DE4101239C1 (fr) * | 1991-01-17 | 1992-04-02 | Th. Goldschmidt Ag, 4300 Essen, De | |
EP0537900A2 (fr) * | 1991-10-18 | 1993-04-21 | Rohm And Haas Company | Epaississants |
JPH11263961A (ja) * | 1998-03-16 | 1999-09-28 | Sanyo Chem Ind Ltd | エマルション型感圧接着剤組成物 |
US6093764A (en) * | 1997-07-18 | 2000-07-25 | Coatex S.A. | Use of a copolymer with a surface-active structure as a dispersing and/or crushing aid |
JP2001303461A (ja) * | 2000-04-28 | 2001-10-31 | Asahi Denka Kogyo Kk | 捺染糊用増粘剤および捺染糊用増粘剤を含有した捺染糊用組成物 |
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DE3048021A1 (de) * | 1980-12-19 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Insektizide und akarizide mittel und ihre verwendung |
FR2826014B1 (fr) * | 2001-06-19 | 2007-04-13 | Coatex Sas | Epaississants non ioniques pour compositions pigmentaires, notamment pour peintures, assurant la compatibilite pigmentaire, et leurs applications |
-
2001
- 2001-06-19 FR FR0108062A patent/FR2826014B1/fr not_active Expired - Lifetime
-
2002
- 2002-06-06 MX MXPA03010238A patent/MXPA03010238A/es active IP Right Grant
- 2002-06-06 WO PCT/FR2002/001939 patent/WO2002102868A1/fr active Application Filing
- 2002-06-06 CA CA2446454A patent/CA2446454C/fr not_active Expired - Fee Related
- 2002-06-06 ES ES02748940.0T patent/ES2498367T3/es not_active Expired - Lifetime
- 2002-06-06 DK DK02748940.0T patent/DK1425325T3/da active
- 2002-06-06 US US10/480,251 patent/US7217761B2/en not_active Expired - Lifetime
- 2002-06-06 KR KR1020037016513A patent/KR100969261B1/ko not_active IP Right Cessation
- 2002-06-06 EP EP02748940.0A patent/EP1425325B1/fr not_active Expired - Lifetime
-
2006
- 2006-11-01 US US11/590,779 patent/US20070066752A1/en not_active Abandoned
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US4079028B1 (fr) * | 1975-10-03 | 1990-08-21 | Rohm & Haas | |
JPH0364309A (ja) * | 1989-08-01 | 1991-03-19 | Toray Ind Inc | ブロックドポリイソシアネート分散液 |
DE4101239C1 (fr) * | 1991-01-17 | 1992-04-02 | Th. Goldschmidt Ag, 4300 Essen, De | |
EP0537900A2 (fr) * | 1991-10-18 | 1993-04-21 | Rohm And Haas Company | Epaississants |
US6093764A (en) * | 1997-07-18 | 2000-07-25 | Coatex S.A. | Use of a copolymer with a surface-active structure as a dispersing and/or crushing aid |
JPH11263961A (ja) * | 1998-03-16 | 1999-09-28 | Sanyo Chem Ind Ltd | エマルション型感圧接着剤組成物 |
JP2001303461A (ja) * | 2000-04-28 | 2001-10-31 | Asahi Denka Kogyo Kk | 捺染糊用増粘剤および捺染糊用増粘剤を含有した捺染糊用組成物 |
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PATENT ABSTRACTS OF JAPAN vol. 015, no. 216 (C - 0837) 4 June 1991 (1991-06-04) * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011030197A2 (fr) | 2009-09-10 | 2011-03-17 | Coatex S.A.S. | Polyurethanes associatifs a base de cardanol, epaississants associatifs correspondants et leurs utilisations |
WO2011104599A1 (fr) | 2010-02-26 | 2011-09-01 | Coatex S.A.S. | Monomere associatif a base d'alcools oxo, polymere acrylique contenant ce monomere, utilisation dudit polymere comme epaississant dans une formulation aqueuse, formulation obtenue |
WO2011104600A1 (fr) | 2010-02-26 | 2011-09-01 | Coatex S.A.S. | Emulsion acrylique associative contenant un monomere a base d'alcool oxo, son procede de fabrication et procede d'epaississement d'une formulation aqueuse a partir de cette emulsion |
WO2012172248A1 (fr) | 2011-06-14 | 2012-12-20 | Coatex | Epaississants non ioniques associatifs contenant des alkyls cyclohexylols, formulations les contenant et leurs utilisations |
WO2012172249A1 (fr) | 2011-06-14 | 2012-12-20 | Coatex | Epaississants non ioniques associatifs contenant des alkyls cyclohexylols, formulations les contenant et leurs utilisations |
WO2013072617A1 (fr) | 2011-11-18 | 2013-05-23 | Coatex | Epaississants ioniques associatifs contenant des alkyls cyclohexylols alkoxyles, leurs utilisations et formulations les contenant |
WO2013072592A2 (fr) | 2011-11-18 | 2013-05-23 | Coatex | Épaississants non ioniques associatifs contenant des alkyls cyclohexylols alkoxyles, leurs utilisations et formulations les contenant |
FR3014874A1 (fr) * | 2013-12-16 | 2015-06-19 | Coatex Sas | Agent epaississant hydrosoluble pour systemes aqueux, formulations le contenant et utilisations |
WO2015092248A1 (fr) | 2013-12-16 | 2015-06-25 | Coatex | Agent épaississant hydrosoluble pour systèmes aqueux, formulations le contenant et utilisations |
WO2016097647A1 (fr) | 2014-12-19 | 2016-06-23 | Coatex | Agent epaississant pour systemes aqueux, formulations le contenant et utilisations |
Also Published As
Publication number | Publication date |
---|---|
CA2446454A1 (fr) | 2002-12-27 |
FR2826014A1 (fr) | 2002-12-20 |
CA2446454C (fr) | 2011-04-12 |
US20070066752A1 (en) | 2007-03-22 |
DK1425325T3 (da) | 2014-09-15 |
KR20040010730A (ko) | 2004-01-31 |
ES2498367T3 (es) | 2014-09-24 |
FR2826014B1 (fr) | 2007-04-13 |
MXPA03010238A (es) | 2004-03-10 |
US20040147672A1 (en) | 2004-07-29 |
KR100969261B1 (ko) | 2010-07-14 |
EP1425325A1 (fr) | 2004-06-09 |
EP1425325B1 (fr) | 2014-08-13 |
US7217761B2 (en) | 2007-05-15 |
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