WO2022003261A1 - Compose triurethane modificateur de rheologie - Google Patents
Compose triurethane modificateur de rheologie Download PDFInfo
- Publication number
- WO2022003261A1 WO2022003261A1 PCT/FR2021/000067 FR2021000067W WO2022003261A1 WO 2022003261 A1 WO2022003261 A1 WO 2022003261A1 FR 2021000067 W FR2021000067 W FR 2021000067W WO 2022003261 A1 WO2022003261 A1 WO 2022003261A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbon atoms
- polyalkoxylated
- monoalcohols
- alkoxylated
- compound
- Prior art date
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Classifications
-
- 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
- C08G18/16—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
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7875—Nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/7893—Nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring having three nitrogen atoms in the ring
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
- C09D5/024—Emulsion paints including aerosols characterised by the additives
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/205—Compounds containing groups, e.g. carbamates
Definitions
- the invention relates to a rheology modifier triurethane compound.
- the invention also provides an aqueous composition comprising a triurethane compound according to the invention as well as a method of controlling the viscosity of an aqueous composition using the triurethane compound according to the invention.
- aqueous coating compositions and in particular for aqueous paint or varnish compositions, it is necessary to control the viscosity both for low or medium shear gradients and for high shear gradients.
- a paint formulation is subjected to numerous constraints requiring particularly complex rheological properties.
- pigment particles When storing paint, pigment particles tend to settle by gravity. Stabilizing the dispersion of these pigment particles then requires the availability of a paint formulation whose viscosity is high at very low shear gradients corresponding to the limiting speed of the particles.
- Paint setting is the amount of paint washed away with an application tool, such as a paintbrush, brush or roller. The tool dipped in and then removed from the paint bucket carrying a large amount of paint will avoid having to be recharged more frequently.
- the paint setting is an increasing function of the viscosity.
- the calculation of the equivalent shear gradient is a function of the paint flow rate for a particular paint thickness on the tool.
- the paint formulation should therefore also have a high viscosity at low to medium shear gradients.
- a high filling power of the paint must be sought so that during its application to a substrate, a large amount of paint is deposited during each pass.
- a high filling power then makes it possible to obtain a greater wet film during each passage of the tool.
- a high viscosity of the paint formulation should therefore be sought at high shear gradients. High viscosity at high shear gradients will also reduce or eliminate the risk of spattering or droplets forming during paint application.
- Reduced viscosity at low or medium shear gradients will also provide a good stretched appearance after application of the paint, especially a single-coat paint, on a substrate whose coated surface will then present a very regular appearance, without dents or hollow. The final visual appearance of the dry film is then much better.
- the paint should not form a sag. It is then necessary for the paint formulation to have a high viscosity at low and medium shear gradients. Finally, after being deposited on a surface, the paint should have a significant leveling capacity. Reduced viscosity at low to medium shear gradients of the paint formulation is then required.
- HEUR-type compounds hydrophobically modified ethoxylated urethanes or ethoxylated and hydrophobically modified urethanes
- rheology modifiers are known as rheology modifiers.
- EP 0307775 discloses polyurethane thickening compounds of paint compositions which are prepared from diisocyanate compounds.
- Document FR 2372865 describes compositions of surfactants and thickening polyurethanes for textile printing pastes.
- the known HEUR-type compounds do not always provide a satisfactory solution.
- the rheology modifying compounds of the state of the art do not always allow effective control of the viscosity or do not always make it possible to satisfactorily improve the compromise between Stormer viscosity (measured at low or medium shear gradients and expressed in KU units) and ICI viscosity (measured at high or very high shear gradients and expressed in s-1).
- the known rheology modifying compounds do not always make it possible to increase the ICI viscosity / Stormer viscosity ratio.
- the triurethane compound according to the invention makes it possible to provide a solution to all or part of the problems of rheology modifying agents of the state of the art.
- the invention provides a triurethane compound T prepared by reacting: a. a molar equivalent of at least one polyisocyanate compound (a) comprising on average 3 isocyanate groups and b.
- polyalkoxylated compound chosen from: linear aliphatic monoalcohols (bl) comprising from 6 to 40 polyalkoxylated carbon atoms, branched aliphatic monoalcohols (b2) comprising from 6 to 40 carbon atoms polyalkoxylated, cycloaliphatic monoalcohols (b3) comprising from 6 to 40 polyalkoxylated carbon atoms, monoaromatic monoalcohols (b4) comprising from 6 to 30 polyalkoxylated carbon atoms, polyaromatic monoalcohols (b5) comprising from 10 to 80 polyalkoxylated carbon atoms, and c.
- linear aliphatic monoalcohols comprising from 6 to 40 polyalkoxylated carbon atoms
- branched aliphatic monoalcohols comprising from 6 to 40 carbon atoms polyalkoxylated
- cycloaliphatic monoalcohols comprising from 6 to 40 polyalkoxylated carbon atoms
- the triurethane compound T is prepared from at least one compound (a) comprising three isocyanate groups and at least one, two or three compounds (b) capable of reacting with these isocyanate groups and comprising a hydrocarbon chain - saturated, unsaturated or aromatic - combined with a polyalkoxylated chain.
- this reactive compound is a monohydroxy compound.
- the invention also provides several other particular triurethane compounds which share these essential characteristics with the compound T according to the invention. These triurethane compounds Ta, Tb and Te according to the invention then respectively comprise 3, 2 or 1 polyalkoxylated chain.
- the invention therefore provides a triurethane compound Ta comprising 3 polyalkoxylated chains.
- the triurethane compound Ta according to the invention is prepared by reaction: a. of a molar equivalent of at least one triisocyanate compound (a) and b.
- polyalkoxylated compound chosen from: linear aliphatic monoalcohols (bl) comprising from 6 to 40 polyalkoxylated carbon atoms, branched aliphatic monoalcohols (b2) comprising from 6 to 40 carbon atoms polyalkoxylated, cycloaliphatic monoalcohols (b3) comprising from 6 to 40 polyalkoxylated carbon atoms, monoaromatic monoalcohols (b4) comprising from 6 to 30 polyalkoxylated carbon atoms, polyaromatic monoalcohols (b5) comprising from 10 to 80 polyalkoxylated carbon atoms, and c.
- linear aliphatic monoalcohols comprising from 6 to 40 polyalkoxylated carbon atoms
- branched aliphatic monoalcohols comprising from 6 to 40 carbon atoms polyalkoxylated
- cycloaliphatic monoalcohols comprising from 6 to 40 polyalkoxylated carbon atoms
- polyalkoxylated compound identical or different, chosen from: linear aliphatic monoalcohols (c1) comprising from 6 to 40 polyalkoxylated carbon atoms, branched aliphatic monoalcohols (c2) comprising from 6 to 40 polyalkoxylated carbon atoms, cycloaliphatic monoalcohols (c3) comprising from 6 to 40 polyalkoxylated carbon atoms, monoaromatic monoalcohols (c4) comprising from 6 to 30 polyalkoxylated carbon atoms, polyaromatic monoalcohols (c5) comprising from 10 to 80 polyalkoxylated carbon atoms.
- linear aliphatic monoalcohols c1 comprising from 6 to 40 polyalkoxylated carbon atoms
- branched aliphatic monoalcohols c2 comprising from 6 to 40 polyalkoxylated carbon atoms
- cycloaliphatic monoalcohols c3 comprising from 6 to 40 polyalk
- the linear aliphatic polyalkoxylated monoalcohols (b1) used to prepare the triurethane compound Ta comprise from 80 to 500 alkoxylated groups.
- the polyalkoxylated monoalcohols (b4) monoaromatic used to prepare the triurethane compound Ta comprise from 6 to 12 carbon atoms or comprise from 22 to 30 carbon atoms.
- the invention therefore also provides a triurethane compound Tb comprising 2 polyalkoxylated chains and one non-alkoxylated chain.
- the triurethane compound Tb according to the invention is prepared by reaction: a. of a molar equivalent of at least one triisocyanate compound (a) and b.
- polyalkoxylated compound chosen from: linear aliphatic monoalcohols (bl) comprising from 6 to 40 polyalkoxylated carbon atoms, branched aliphatic monoalcohols (b2) comprising from 6 to 40 carbon atoms polyalkoxylated, cycloaliphatic monoalcohols (b3) comprising from 6 to 40 polyalkoxylated carbon atoms, monoaromatic monoalcohols (b4) comprising from 6 to 30 polyalkoxylated carbon atoms, polyaromatic monoalcohols (b5) comprising from 10 to 80 polyalkoxylated carbon atoms, vs.
- linear aliphatic monoalcohols comprising from 6 to 40 polyalkoxylated carbon atoms
- branched aliphatic monoalcohols comprising from 6 to 40 carbon atoms polyalkoxylated
- cycloaliphatic monoalcohols comprising from 6 to 40 polyalkoxylated carbon atoms
- the invention therefore also provides a triurethane compound Te comprising 1 polyalkoxylated chain and 2 non-alkoxylated chains.
- the triurethane compound Te according to the invention is prepared by reaction: a. of a molar equivalent of at least one triisocyanate compound (a) and b.
- the condensation of compounds a, b and c is carried out in the presence of a catalyst.
- This catalyst can be chosen from an amine, preferably l, 8-diazabicyclo [5.4.0] undec-7-ene (DBU), a derivative of a metal chosen from Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Traces of water can also participate in the catalysis of the reaction.
- metal derivatives preferred is a derivative selected from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin diacetate, sodium oxide.
- the preferred metal derivative is chosen from a derivative of Bi, a derivative of S n and a derivative of Ti.
- ⁇ symmetrical aromatic diisocyanate compounds preferably: diphenylmethylene 2,2'-diisocyanate (2,2'-MDI) and diphenylmethylene 4,4'-diisocyanate (4,4'-MDI);
- the non-alkoxylated monoalcohols are compounds comprising a hydrocarbon chain and a single terminal hydroxyl (OH) group.
- the non-alkoxylated monoalcohols are compounds of formula R ′ —OH in which R ′ represents a hydrocarbon chain.
- the polyalkoxylated monoalcohols comprise from 2 to 500 alkoxylated groups, preferably from 80 to 400 alkoxylated groups or from 100 to 200 alkoxylated groups.
- the preferred organic solvents are non-reactive solvents with the isocyanate functions of compound a, in particular the solvents chosen from hydrocarbon solvents (in particular Cs to C30 petroleum cuts), aromatic solvents (in particular toluene and its derivatives) and their derivatives. combinations. More preferably according to the invention, the condensation is carried out directly with the various reagents or else is carried out in toluene.
- This method of viscosity control according to the invention comprises the addition of at least one triurethane compound according to the invention in an aqueous composition.
- This viscosity control method can also include the addition of at least one triurethane compound prepared according to the preparation method according to the invention.
- the viscosity control method according to the invention is implemented by means of an aqueous composition according to the invention. Also so preferred, the viscosity control method according to the invention is implemented by means of an aqueous formulation according to the invention.
- the triurethane compound Tal obtained is formulated using a surfactant of the ethoxylated alcohol type (n-octanol ethoxylated with ten equivalents of ethylene oxide), 1000 ppm of an agent biocide (Biopol SMV Chemipol) and 1000 ppm of an antifoam agent (Tego 1488 Evonik).
- a composition is obtained consisting of 20% by mass of compound according to the invention, 5% by mass of surfactant compound and 75% by mass of water.
- Example 1-2 preparation of a Tbl compound according to the invention
- the obtained triurethane compound Tbl is formulated using the surfactant compound, the biocidal agent and the antifoam agent of Example 1-1.
- the composition obtained consists of 20% by mass of the compound according to the invention, 5% by mass of surfactant compound and 75% by mass of water.
- Example 3 characterization of paint formulations according to the invention
- the Brookfield viscosity measured at 25 ° C and at 10 rpm and at 100, was determined 24 hours after their preparation. rpm (p Bki o and p Bki oo in mPa.s) using a Brookfield DV-1 viscometer with mobile type RV.
- the cone-plane viscosity or ICI viscosity measured at high shear gradient (pi in mPa.s), was determined 24 hours after their preparation and at room temperature, by means of a Cone & Plate Research Equipment London (REL) viscometer with a measuring scale of 0 to 5 poises, and the Stormer viscosity, measured at a medium shear gradient (pS in Krebs Units or KU), using the standard module of a viscometer Brookfield KU-2.
- the properties of the paint formulations are shown in Table 3.
- the triurethane compounds according to the invention make it possible to prepare paint formulations whose viscosities are particularly well controlled.
- the viscosity p i is particularly high and the ratio m / p is then excellent.
- the compounds according to the invention allow an excellent compromise between viscosity at high shear gradient and viscosity at low shear gradient.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dispersion Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202180044424.6A CN115916911A (zh) | 2020-06-30 | 2021-06-29 | 流变改性的三氨基甲酸酯化合物 |
US18/002,379 US20230265295A1 (en) | 2020-06-30 | 2021-06-29 | Rheology-modifying triurethane compound |
EP21746505.3A EP4172278A1 (fr) | 2020-06-30 | 2021-06-29 | Compose triurethane modificateur de rheologie |
KR1020237001713A KR20230027181A (ko) | 2020-06-30 | 2021-06-29 | 레올로지-개질 트리우레탄 화합물 |
BR112022027006A BR112022027006A2 (pt) | 2020-06-30 | 2021-06-29 | Composto de triuretano, métodos para preparar um composto de triuretano e para controlar a viscosidade de uma composição aquosa composição aquosa, formulação aquosa e pasta de pigmento à base de água |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FRFR2006871 | 2020-06-30 | ||
FR2006871A FR3111893B1 (fr) | 2020-06-30 | 2020-06-30 | Composé triuréthane modificateur de rhéologie |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2022003261A1 true WO2022003261A1 (fr) | 2022-01-06 |
WO2022003261A8 WO2022003261A8 (fr) | 2022-12-22 |
Family
ID=73698915
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2021/000067 WO2022003261A1 (fr) | 2020-06-30 | 2021-06-29 | Compose triurethane modificateur de rheologie |
Country Status (7)
Country | Link |
---|---|
US (1) | US20230265295A1 (fr) |
EP (1) | EP4172278A1 (fr) |
KR (1) | KR20230027181A (fr) |
CN (1) | CN115916911A (fr) |
BR (1) | BR112022027006A2 (fr) |
FR (1) | FR3111893B1 (fr) |
WO (1) | WO2022003261A1 (fr) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2372865A1 (fr) | 1976-12-01 | 1978-06-30 | Rohm & Haas | Compositions epaississantes |
EP0307775A2 (fr) | 1987-09-18 | 1989-03-22 | Rheox International, Inc. | Agent épaississant d'un polyuréthane modifié dispersible dans l'eau ayant une viscosité améliorée à taux de cisaillement élevé dans des systèmes aqueux |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11507405A (ja) * | 1995-06-07 | 1999-06-29 | ザ シャーウィン−ウィリアムズ カンパニー | 親水的にエンドキャップされたポリウレタン増粘剤 |
JPH0967563A (ja) * | 1995-09-01 | 1997-03-11 | Asahi Denka Kogyo Kk | 粘性調整剤 |
JP5542897B2 (ja) * | 2011-12-14 | 2014-07-09 | ローム アンド ハース カンパニー | レオロジー調整剤 |
FR3057871B1 (fr) * | 2016-10-20 | 2018-11-02 | Coatex | Compose urethane modificateur de rheologie |
-
2020
- 2020-06-30 FR FR2006871A patent/FR3111893B1/fr active Active
-
2021
- 2021-06-29 EP EP21746505.3A patent/EP4172278A1/fr active Pending
- 2021-06-29 WO PCT/FR2021/000067 patent/WO2022003261A1/fr unknown
- 2021-06-29 KR KR1020237001713A patent/KR20230027181A/ko unknown
- 2021-06-29 BR BR112022027006A patent/BR112022027006A2/pt unknown
- 2021-06-29 US US18/002,379 patent/US20230265295A1/en active Pending
- 2021-06-29 CN CN202180044424.6A patent/CN115916911A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2372865A1 (fr) | 1976-12-01 | 1978-06-30 | Rohm & Haas | Compositions epaississantes |
EP0307775A2 (fr) | 1987-09-18 | 1989-03-22 | Rheox International, Inc. | Agent épaississant d'un polyuréthane modifié dispersible dans l'eau ayant une viscosité améliorée à taux de cisaillement élevé dans des systèmes aqueux |
Non-Patent Citations (2)
Title |
---|
CAS , no. 25265-77-4 |
CAS, no. 34590-94-8 |
Also Published As
Publication number | Publication date |
---|---|
EP4172278A1 (fr) | 2023-05-03 |
FR3111893B1 (fr) | 2023-04-28 |
WO2022003261A8 (fr) | 2022-12-22 |
KR20230027181A (ko) | 2023-02-27 |
US20230265295A1 (en) | 2023-08-24 |
BR112022027006A2 (pt) | 2023-01-24 |
CN115916911A (zh) | 2023-04-04 |
FR3111893A1 (fr) | 2021-12-31 |
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