WO2006087079A1 - Compositions durcissables par reaction d'addition de michael - Google Patents
Compositions durcissables par reaction d'addition de michael Download PDFInfo
- Publication number
- WO2006087079A1 WO2006087079A1 PCT/EP2006/000689 EP2006000689W WO2006087079A1 WO 2006087079 A1 WO2006087079 A1 WO 2006087079A1 EP 2006000689 W EP2006000689 W EP 2006000689W WO 2006087079 A1 WO2006087079 A1 WO 2006087079A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- component
- addition
- crosslinkable compositions
- general formula
- functional
- 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
- C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/04—Homopolymers or copolymers of monomers containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
- C09K3/1018—Macromolecular compounds having one or more carbon-to-silicon linkages
Definitions
- the invention relates to compositions which can be cured by a Michael-type addition reaction and to their use.
- Michael addition of activated methylene compounds, e.g. Malonic esters, cyanoacetic esters or amines, the so-called Michael donors, with electron-poor alkenes, such. ⁇ , ⁇ -unsaturated
- curable compositions according to a Michael-type reaction are that neither high-cost noble metal catalysts nor toxicologically questionable tin catalysts are necessary for the curing.
- hardening no products are split off, which could lead to a shrinkage of the hardening product or to an environmental impact.
- U.S. 4,698,406 discloses Michael addition curable organopolysiloxane blends. These mixtures contain, as crosslinkable components, an aminoalkyl- and an acryl-functional organopolysiloxane. Acrylic-functional components are understood below to mean compounds having acrylic, methacrylic, acrylamide and methacrylamide groups.
- Michael acceptor component i.a. describes an organopolysiloxane whose acrylic functions L correspond to the general formula I,
- R 1 is hydrogen or a monovalent organic radical.
- EP 0 780 422 and EP 0 818 497 describe, by Michael addition, curable aqueous organopolysiloxane emulsions which are obtainable by mixing a Michael acceptor-functionalized organopolysiloxane, an emulsifier and a Michael donor-functionalized hardener in water.
- Acrylic functional organopolysiloxanes are i.a. by
- Acrylic functionalization of pyrogenic and colloidal silica is described inter alia in US 2003/0194549 A and US 4491508 A and is, for example, by reacting the oxides achieved with 3-methacrylatopropyltrimethoxysilane.
- Curable organopolysiloxane mixtures would be advantageous in which the Michael acceptor contains units of the general formula I and thereby has a high reactivity towards Michael donors, so that a sufficient network density of the composition obtainable after curing is ensured for an application.
- the invention relates to addition-crosslinkable compositions Z, the one
- Component A which carries at least one activated methylene group, amino, carbinol or thiol as Michael donor, and a
- Component B the at least one radical of the general formula II ⁇ Si - CR 2 2 -ADC (II),
- R 2 is hydrogen or hydrocarbon radical having 1 to 12
- Carbon atoms whose carbon chain may be interrupted by non-adjacent oxygen, sulfur, or NR 3 groups,
- R 3 is hydrogen or hydrocarbon radical having 1 to 12 carbon atoms
- D is a carbonyl group
- C is an ethylenically unsaturated group.
- Component B which carries at least one functional group of the general formula II and whose functional group ADC is only separated by a methylene group from the silyl group ⁇ Si, shows a significantly higher reactivity towards the component A than a component whose Michael acceptor a longer alkyl chain (general formula I: - (CR ⁇ ) x "it m x ⁇ 2) is connected to the silyl group.
- component A all amino- or carbinol- or thiol-functional monomers, oligomers or polymers
- oligomeric and polymeric components A are common amine hardeners which are used, for example, for crosslinking epoxy resins, e.g. Diethylenetriamine, triethylenetetramine,
- aminoethylpiperazine polyethylenepolyamine, metaphenylenediamine, diaminodiphenylsulfone, Diethyl and polyamides of type Versamid ® (Henkel) or Ancamide ® (Air Products and Chemicals, Inc.).
- aminofunktioneile silanes such as trimethoxysilane be Ethylendiaminopropyl or hydrolysis products thereof, amino functional organopolysiloxanes such as Wacker ® HP 2000 (Wacker-Chemie) and siliconates, such as are described for example in EP 0780422 A2, are used.
- component A monomeric, oligomeric and polymeric compounds such as acrylic polyols, polyester polyols, polyether polyols, epoxy polyols,
- Polyurethane polyols and carbinol functional organopolysiloxanes are used;
- component A is monomeric, oligomeric and polymeric compounds which carry activated methylene groups. This can be, for example acetoacetoxy polymers as described in Park & Lack, 110th year, 2/2004, pp 22-24 ⁇ , or polymers as activated
- Methylene groups units of the formulas -CO-CHR U -CO-, NC-CHR U -CO-, -CO-CHR U -NC> 2, CHR U -CN, where R u is a monovalent organic radical or hydrogen.
- R u is a monovalent organic radical or hydrogen.
- correspondingly functionalized particles such as, for example, amino-functional pyrogenic, precipitated or colloidal silica or metal oxides, for example aluminum oxide, can be used as component A.
- Component B has radicals of the general formula II which have an electron-deficient ethylenically unsaturated group C as Michael acceptor.
- the hydrocarbon radicals R ⁇ i to 4 carbon atoms Preferably, the hydrocarbon radicals R ⁇ i to 4 carbon atoms.
- Hydrocarbon radicals R 3 1 to 4 carbon atoms.
- component B are monomeric, oligomeric or polymeric Compounds or particulate structures which have at least one functional group of the general formula II.
- A-D-C of the general formula II preferably has the
- component B are organopolysiloxanes of the general formula III,
- R ⁇ hydrogen or a monovalent optionally substituted by - CO, -NCO, -NR X 2 '-COOH, -halogen, -P (O) (OR X ) 2 , -EPOX, -SH, -OH or -CONR X 2 substituted Si-C-bonded C 1 . C2o hydrocarbon radical or C 1 -C 1 S-.
- R 5 is an optionally cyano or halogen-substituted C 1- C 1 5.Kohlenwasserstoffrest,
- R x is hydrogen or a C 1 -C 1Q- hydrocarbon radical optionally substituted by -CN or halogen, s are values of at least 1, v are values of 1, 2 or 3, u values of 1, 2 or 3, where u must be less than or equal to v and
- R ⁇ , A, D, C have the above meanings.
- the hydrocarbon radicals R 4 have 1 to 6 carbon atoms. Particularly preferred are methyl and ethyl radicals. Preferably, the hydrocarbon radicals R ⁇ have 1 to 4 carbon atoms. Particularly preferred are methyl and ethyl radicals.
- component B metal oxide and metal mixed oxide particles (eg aluminum oxides such as corundum, mixed aluminum oxides with other metals and / or silicon, titanium oxides, zirconium oxides, iron oxides), silica particles (eg colloidal silica, fumed silica, precipitated silica) can be used having on their surface over functions of general formula II, via which a reaction with the functional groups of component A can take place.
- metal oxide and metal mixed oxide particles eg aluminum oxides such as corundum, mixed aluminum oxides with other metals and / or silicon, titanium oxides, zirconium oxides, iron oxides
- silica particles eg colloidal silica, fumed silica, precipitated silica
- These particles which can be used as component B preferably have an average diameter of less than 1 mm, more preferably less than 1000 nm, the particle size being determined by transmission electron microscopy.
- the particles which can be used as component B consist of pyrogenic silicic acid functionalized with radicals of the general formula II.
- correspondingly functionalized colloidal silicon or metal oxides are used, which are preferably present as a dispersion of the corresponding submicron oxide particles in an aqueous or organic solvent.
- the oxides of the metals aluminum, titanium, Zirconium, tantalum, tungsten, hafnium and tin are used.
- compositions Z one or more different components A and B can be used.
- compositions Z are the subject of the invention, which contain, as component A, an amine-functional siloxane and, as components B, a methacryl-functional siloxane and a methacryl-functional silicic acid.
- the acrylic functional organopolysiloxanes and oxides are prepared by customary processes known to the person skilled in the art, for example cohydrolysis, equilibration and termination of silanol-functional compounds.
- alkoxy- and chlorosilanes examples are acrylatimethyl-trimethoxysilane, acrylatomethyl-methyldimethoxysilane, acrylatomethyl-dimethylmethoxysilane, acrylatomethyl-triethoxysilane, acrylatomethyl-methyldiethoxysilane, acrylatomethyl-dimethylethoxysilane, acrylatomethyl-trichlorosilane, acrylatomethyl-methyldichlorosilane, acrylatorethyl-dimethylchlorosilane, methacrylatomethyltrimethoxysilane, methacrylatomethyl- methyldimethoxysilane, methacrylatomethyldimethylmethoxysilane, methacrylatomethyltriethoxysilane, methacrylatomethyldiethoxysilane, methacrylatomethyldimethylethoxysilane, methacrylatomethyltrichlorosilane, me
- Methacrylamidomethyl-triethoxysilane methacrylamidomethyl-methyldiethoxysilane, methacrylamidomethyl-dimethylethoxysilane, methacrylamidomethyl-trichlorosilane, methacrylamidomethyl-methyldichlorosilane and methacrylamidomethyl-dimethylchlorosilane.
- compositions 2 The preparation of the compositions 2 is carried out by mixing the components A and B in the presence or
- component A is present, for example, as an alcoholic solution, then component B can be mixed into this solution and the composition Z obtained can be applied directly.
- the solvent is in this case before or during the
- Hardening process evaporated or remains as a plasticizer in the cured material.
- the solvent after mixing e.g. be removed by distillation before the composition is cured.
- at least one of the components A or B is present below the curing temperature as a liquid.
- a solid component may be dissolved or dispersed in the liquid component.
- components A and / or B are in the form of an aqueous emulsion or dispersion.
- emulsifiers and / or protective colloids are polyvinyl alcohols, cellulose derivatives or vinylpyrrolidone-containing polymers.
- Common emulsifiers are, for example, ethoxylated alcohols and phenols (alkyl radical C 4 -C 1 S / EO grade 3-100), alkali metal and ammonium salts of alkyl sulfates (C 3 -C 18), sulfuric acid and phosphoric acid esters and alkyl sulfonates. Particularly preferred are sulfosuccinic and alkali alkyl sulfates and polyvinyl alcohols.
- emulsifiers are, for example, ethoxylated alcohols and phenols (alkyl radical C 4 -C 1 S / EO grade 3-100), alkali metal and ammonium salts of alkyl sulfates (C 3 -C 18), sulfuric acid and phosphoric acid esters and alkyl sulf
- the emulsions containing the components A and / or B are prepared in a conventional manner known to the person skilled in the art. To avoid a premature reaction between the components A and B, is preferably one of
- Component A and Component B are dispersed separately and then combined.
- composition Z containing an ⁇ , ⁇ -amino functional linear organopolysiloxane as component A and an organopolysiloxane resin having a low density of acrylic functions as component B provides an elastomer after cure.
- component B having a high acrylic density results in a thermoset material after curing.
- the ratio of components A and B to one another is preferably selected such that the molar ratio of Michael donors to radicals of the general formula II is 2: 1 to 1: 2 is. Preferably, a ratio of 1.5: 1 to 1: 1.5 is selected. In particular, an excess of an amine-functional compound used as component A should be avoided in order to prevent yellowing of the cured materials.
- compositions Z are preferably used for this 5 min - 48 h at 0-180 0 C heated. Particularly preferably, the curing is carried out for 20 min - 24 hours at 20-120 0 C.
- the curing takes place after evaporation of the aqueous solvent. The evaporation of the water can be carried out under atmospheric pressure or reduced pressure and / or with heating.
- composition Z which contain as component A an activated methylene compound, carbinol- or thiol-functional compounds, find tertiary
- Amines such as 1, 5-diazabicyclo [4.3.0 1 ' s ] non-5-ene (DBN), 1,8-
- the catalysts are preferably added in 0.1 to 10 wt .-%; most preferably, the amounts of catalyst added are less than 5% by weight.
- compositions Z can also contain common solvents as well as the additives and additives customary in formulations.
- leveling agents, surface-active substances, adhesion promoters and light stabilizers should be mentioned such as UV absorbers and / or radical scavengers such as 3,5-di-tert-butyl-4-hydroxytoluene (BHT), thixotropic agents and other solids and fillers.
- BHT 3,5-di-tert-butyl-4-hydroxytoluene
- thixotropic agents such as 3,5-di-tert-butyl-4-hydroxytoluene (BHT)
- BHT 3,5-di-tert-butyl-4-hydroxytoluene
- thixotropic agents such as 3,5-di-tert-butyl-4-hydroxytoluene (BHT)
- BHT 3,5-di-tert-butyl-4-hydroxytoluene
- thixotropic agents such as 3,5-di-
- compositions Z are preferably used as adhesives and sealants and as coating agents for preferably metal, wood, paper, glass, textile and plastic substrates.
- a preferred application is the use of the compositions Z for the encapsulation of electronic components.
- the organopolysiloxane used HP 2000 MQ resin powder 803 TF and Silres ® SIO are from Wacker-Chemie GmbH / Kunststoff, available. Tonsil ® Optimum FF is a product of southern chemistry.
- Example 5 According to Example 5, 5.00 g of the non-functionalized organopolysiloxane resin MQ 803 TF with 1.65 g of an amino-functional organopolysiloxane resin mixed HP 2000, and stored for 1 hour at 120 0 C. This gives a cloudy, highly viscous oil, which is covered by a thin skin. The product dissolves when stored in toluene.
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
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- Compositions Of Macromolecular Compounds (AREA)
Abstract
La présente invention concerne des compositions Z durcissables par addition, qui contiennent: une composante A qui porte au moins un groupe méthylène rendu actif, une fonction amino, carbinol ou thiol en tant que donneur de Michaël; et une composante B qui présente au moins un radical de formule générale (II) =Si-CR22-A-D-C, dans laquelle R2 est hydrogène ou un radical hydrocarbure contenant de 1 à 12 atomes de carbone et dont la chaîne carbonée peut être interrompue par des groupes oxygène, soufre ou NR3 non voisins, R3 est hydrogène ou un radical hydrocarbure contenant de 1 à 12 atomes de carbone, A est oxygène, soufre, =NR3 ou =N-(D-C), D est un groupe carbonyle et C est un groupe éthyléniquement insaturé.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005007320.4 | 2005-02-17 | ||
DE200510007320 DE102005007320A1 (de) | 2005-02-17 | 2005-02-17 | Durch Michael Additionsreaktion härtbare Zusammensetzungen |
Publications (1)
Publication Number | Publication Date |
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WO2006087079A1 true WO2006087079A1 (fr) | 2006-08-24 |
Family
ID=36046627
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2006/000689 WO2006087079A1 (fr) | 2005-02-17 | 2006-01-26 | Compositions durcissables par reaction d'addition de michael |
Country Status (2)
Country | Link |
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DE (1) | DE102005007320A1 (fr) |
WO (1) | WO2006087079A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012045902A1 (fr) | 2010-10-07 | 2012-04-12 | Consejo Superior De Investigaciones Científicas (Csic) | Procédé permettant l'enrobage et la fonctionnalisation de nanoparticules par réaction de michael |
WO2021110621A1 (fr) | 2019-12-04 | 2021-06-10 | Fischerwerke Gmbh & Co. Kg | Système hybride de durcissement par réaction de michael destiné à être utilisé dans une technologie de fixation chimique |
WO2021110622A1 (fr) | 2019-12-04 | 2021-06-10 | Fischerwerke Gmbh & Co. Kg | Résine synthétique à durcissement par réaction de michael destinée à être utilisée dans une technologie de fixation chimique |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102006055974A1 (de) * | 2006-11-24 | 2008-05-29 | Henkel Kgaa | Reaktionsklebstoff |
WO2018134291A1 (fr) | 2017-01-19 | 2018-07-26 | Jotun A/S | Composition antisalissure |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4698406A (en) * | 1986-11-04 | 1987-10-06 | Dow Corning Corporation | Curable organopolysiloxane composition |
US5292849A (en) * | 1991-12-27 | 1994-03-08 | Shin-Etsu Chemical Co., Ltd. | Process for the manufacturing of acrylic organopolysiloxanes |
EP0780422A2 (fr) * | 1995-12-20 | 1997-06-25 | Dow Corning Corporation | Emulsions à base de silicones réticulant par réaction d'addition Michael |
EP0818497A2 (fr) * | 1996-07-09 | 1998-01-14 | Dow Corning Corporation | Emulsions réticulables par réaction d'addition Michael pour former des compositions organiques modifiés par du silicone |
DE10219734A1 (de) * | 2002-05-02 | 2003-06-05 | Consortium Elektrochem Ind | Herstellung von (meth)acrylfunktionellen Siloxanen |
WO2004089961A1 (fr) * | 2003-04-07 | 2004-10-21 | Consortium für elektrochemische Industrie GmbH | Particules fonctionnalisees organosilyle et leur production |
-
2005
- 2005-02-17 DE DE200510007320 patent/DE102005007320A1/de not_active Withdrawn
-
2006
- 2006-01-26 WO PCT/EP2006/000689 patent/WO2006087079A1/fr not_active Application Discontinuation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4698406A (en) * | 1986-11-04 | 1987-10-06 | Dow Corning Corporation | Curable organopolysiloxane composition |
US5292849A (en) * | 1991-12-27 | 1994-03-08 | Shin-Etsu Chemical Co., Ltd. | Process for the manufacturing of acrylic organopolysiloxanes |
EP0780422A2 (fr) * | 1995-12-20 | 1997-06-25 | Dow Corning Corporation | Emulsions à base de silicones réticulant par réaction d'addition Michael |
EP0818497A2 (fr) * | 1996-07-09 | 1998-01-14 | Dow Corning Corporation | Emulsions réticulables par réaction d'addition Michael pour former des compositions organiques modifiés par du silicone |
DE10219734A1 (de) * | 2002-05-02 | 2003-06-05 | Consortium Elektrochem Ind | Herstellung von (meth)acrylfunktionellen Siloxanen |
WO2004089961A1 (fr) * | 2003-04-07 | 2004-10-21 | Consortium für elektrochemische Industrie GmbH | Particules fonctionnalisees organosilyle et leur production |
Non-Patent Citations (1)
Title |
---|
ALTMANN ET AL: "The hydrolysis/condensation behaviour of methacryloyloxyalkylfunctio nal alkoxysilanes: structure-reactivity relations", MONATSHEFTE FUER CHEMIE, SPRINGER VERLAG, VIENNA, AT, vol. 134, 12 June 2003 (2003-06-12), pages 1081 - 1092, XP002328645, ISSN: 0026-9247 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012045902A1 (fr) | 2010-10-07 | 2012-04-12 | Consejo Superior De Investigaciones Científicas (Csic) | Procédé permettant l'enrobage et la fonctionnalisation de nanoparticules par réaction de michael |
WO2021110621A1 (fr) | 2019-12-04 | 2021-06-10 | Fischerwerke Gmbh & Co. Kg | Système hybride de durcissement par réaction de michael destiné à être utilisé dans une technologie de fixation chimique |
WO2021110622A1 (fr) | 2019-12-04 | 2021-06-10 | Fischerwerke Gmbh & Co. Kg | Résine synthétique à durcissement par réaction de michael destinée à être utilisée dans une technologie de fixation chimique |
Also Published As
Publication number | Publication date |
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DE102005007320A1 (de) | 2006-08-24 |
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