WO2011069771A1 - Heat-expandable microcapsules comprising magnetic metal oxide particles - Google Patents
Heat-expandable microcapsules comprising magnetic metal oxide particles Download PDFInfo
- Publication number
- WO2011069771A1 WO2011069771A1 PCT/EP2010/067286 EP2010067286W WO2011069771A1 WO 2011069771 A1 WO2011069771 A1 WO 2011069771A1 EP 2010067286 W EP2010067286 W EP 2010067286W WO 2011069771 A1 WO2011069771 A1 WO 2011069771A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- metal oxide
- oxide particles
- microcapsule
- shell
- coated metal
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/32—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof from compositions containing microballoons, e.g. syntactic foams
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/14—Polymerisation; cross-linking
Definitions
- Heat-expandable microcapsules comprising magnetic metal oxide particles
- the invention relates to heat-expandable microcapsules which comprise magnetic metal oxide particles enclosed by a shell, their production and use.
- US 6106946 discloses heat-expandable microcapsules which comprise magnetic particles having an average particle diameter of from 5 to 200 nm.
- the microcapsules are a constituent of sound-absorbing and insulating materials, as are used in electrical devices, vehicles or building materials .
- EP-A-1185594 discloses heat-expandable microcapsules which expand as a result of the introduction of heat and thereby weaken the cohesion of adhesives and the interfacial bonds.
- a disadvantage of this process is considered to be that the entire object warms up as a result of introducing the heat and not just the area where the bonds are to be broken.
- such a process can only be used to a limited extent.
- it is not very energy-efficient to heat large parts when it is only necessary to heat small areas in a targeted manner .
- WO 2006/042782 discloses a process for recycling
- the adhesive mass here can comprise ferromagnetic, ferrimagnetic or superparamagnetic particles which permit inductive heating of the adhesive mass.
- the adhesive mass can comprise heat-expandable microcapsules which are
- magnetic particles and the microcapsules are spatially separate from one another, meaning that the advantages of inductive heating are only partly translated. Furthermore, the application of the magnetic particles involves
- the invention provides a microcapsule consisting of a capsule shell made of a thermoplastic resin and a
- the capsule shell which comprises magnetic particles and one or more hydrocarbons with a boiling point of -15°C to 220°C, or consists thereof, where the magnetic particles are magnetic metal oxide particles with a shell comprising silicon dioxide,
- the coated metal oxide particles have an average primary particle diameter of from 2 to 100 nm, preferably 10 to 80 nm and particularly preferably 20 to 70 nm, and where the average diameter of the microcapsules is 5 to 50 ym, preferably 10 to 30 ym.
- magnetic metal oxide particles are to be understood as meaning those which have ferromagnetic, ferrimagnetic and/or superparamagnetic properties. In the presence of electrical, magnetic or electromagnetic alternating fields, these particles lead to a heating of the dispersion located in the microcapsule and thus to an expansion of the microcapsule.
- coated metal oxide particles may be isolated
- aggregated particles may be present here in a form in which metal oxide particles have become intergrown and the shell surrounds the intergrown metal oxide particles.
- the microcapsule according to the invention can comprise, essentially or exclusively, such coated metal oxide particles, in which the metal oxide particles have become intergrown and the shell surrounds the intergrown metal oxide particles.
- the average diameter of the microcapsules according to the invention can increase upon heating to 80 to 220°C by a hundred times, preferably by 40 to 80 times, the original average diameter without leading to destruction of the microcapsule .
- invention is preferably 1 to 10 mm, particularly
- the fraction of the coated metal oxide particles is 0.001 to 5% by weight, based on the microcapsule.
- a fraction of from 0.01 to 1% by weight is adequate for an expansion of the microcapsule by a factor of 40 to 80 in the presence of electromagnetic alternating fields.
- the fraction of the coated metal oxide particles, based on the dispersion can be 0.1 to 10% by weight, preferably 0.5 to 5.
- the metal oxide particles present in the microcapsule according to the invention are preferably selected from the group consisting of the oxides of cobalt, chromium, dysprosium, iron, erbium, gadolinium, holmium, nickel and terbium.
- the metal oxides are iron oxides, such as haematite, magnetite and
- maghemite may be present individually or in the form of a mixture.
- the coated metal oxide particles have a) a BET surface area of from 10 to 80 m 2 /g, b) a thickness of the shell of from 2 to 30 nm and c) a content of iron oxide of from 60 to 90% by weight and of silicon dioxide of from 10 to 40% by weight, in each case based on the coated metal oxide particles.
- metal oxide particles may also be present, the shell of which has been surface-modified. These can be obtained by treating the coated metal oxide particles with a surface-modifying agent, in particular one with which a hydrophobicization of the surface results. By virtue of this measure, the stability of the dispersion in the inside of the microcapsule can be improved.
- Preferred surface-modifying agents may be in particular the following silanes:
- R alkyl, such as methyl, ethyl, n-propyl, isopropyl, butyl
- R' alkyl, such as methyl, ethyl, n-propyl, isopropyl, butyl
- R' cycloalkyl
- n 1-20
- y l, 2.
- R ' ' ' ' ' H, alkyl .
- cyclic polysiloxanes D3, D4, D5 and also polysiloxanes and silicone oils can also be used.
- D3, D4 and D5 are to be understood as meaning cyclic polysiloxanes having 3, 4 or 5 units of the type
- dimethylpolysiloxanes can be used particularly
- the dispersion in the inside of the microcapsule also comprises one or more hydrocarbons having a boiling point of from -15°C to 220°C.
- hydrocarbon is also intended to include a halogenated hydrocarbon.
- the capsule shell of the microcapsule according to the invention is a thermoplastic resin. It can be obtained from one or more polymerizable monomers, the monomers being selected from the group consisting of acrylamide, acrylonitrile, acrylic acid, benzyl methacrylate,
- N, -dimethylacrylamide, N, -dimethylmethacrylamide, tert- butyl methacrylate and N-vinylpyrrolidone N, -dimethylacrylamide, N, -dimethylmethacrylamide, tert- butyl methacrylate and N-vinylpyrrolidone .
- one or more polymerizable crosslinking monomers having two or more polymerizable double bonds may be present. Examples thereof are ethylene glycol
- the invention further provides a process for producing the microcapsule according to the invention, in which a) an organic dispersion which comprises coated metal
- oxide particles having an average primary particle diameter of from 2 to 100 nm, the shell of which comprises amorphous silicon dioxide, b) an aqueous solution or water c) and one or more monomers, if appropriate in the
- polymerization catalyst in both variants are, for example, peroxides, such as benzoyl peroxide, tert-butyl perbenzoate, cumyl hydroperoxides, tert-butyl peracetate, lauryl peroxide and diisopropyl
- peroxides such as benzoyl peroxide, tert-butyl perbenzoate, cumyl hydroperoxides, tert-butyl peracetate, lauryl peroxide and diisopropyl
- azobisdimethylvaleronitrile and azobisisobutyronitrile and also azo compounds such as azoamide compounds and alkylazo compounds.
- the dispersion polymerization preferably takes place at temperatures of from 40 to 80°C. Preference is likewise given to an embodiment in which the dispersion polymerization is carried out under shearing conditions at an energy density of at least 1000 KJ/m 3 .
- the invention further provides the use of the
- thermoplasts as a constituent of thermosets, as a constituent of paper products and in technical textile fabrics.
Abstract
Microcapsule consisting of a capsule shell made of a thermoplastic resin and a dispersion enclosed by the capsule shell which comprises magnetic particles and one or more hydrocarbons with a boiling point of -15°C to 220°C, where the magnetic particles are magnetic metal oxide particles with a shell comprising silicon dioxide and the coated metal oxide particles have an average primary particle diameter of from 2 to 100 nm and where the average diameter of the microcapsule is 5 to 50 μm. The microcapsule can be obtained by subjecting a) an organic dispersion which comprises coated metal oxide particles having an average primary particle diameter of from 2 to 100 nm, the shell of which comprises amorphous silicon dioxide, b) an aqueous solution or water and c) one or more monomers, if appropriate in the presence of one or more polymerization catalysts, to a dispersion polymerization.
Description
Heat-expandable microcapsules comprising magnetic metal oxide particles
The invention relates to heat-expandable microcapsules which comprise magnetic metal oxide particles enclosed by a shell, their production and use.
US 6106946 discloses heat-expandable microcapsules which comprise magnetic particles having an average particle diameter of from 5 to 200 nm. The microcapsules are a constituent of sound-absorbing and insulating materials, as are used in electrical devices, vehicles or building materials .
EP-A-1185594 discloses heat-expandable microcapsules which expand as a result of the introduction of heat and thereby weaken the cohesion of adhesives and the interfacial bonds. A disadvantage of this process is considered to be that the entire object warms up as a result of introducing the heat and not just the area where the bonds are to be broken. For articles which have heat-sensitive areas, such a process can only be used to a limited extent. Moreover, it is not very energy-efficient to heat large parts when it is only necessary to heat small areas in a targeted manner .
WO 2006/042782 discloses a process for recycling
electrical or electronic components in which, in one process step, an adhesive connection between two elements of the component, formed by an adhesive mass, is broken by expandable particles located in the adhesive mass
expanding as a result of supplying energy and thereby being able to force open the adhesive bond. The adhesive
mass here can comprise ferromagnetic, ferrimagnetic or superparamagnetic particles which permit inductive heating of the adhesive mass. Furthermore, the adhesive mass can comprise heat-expandable microcapsules which are
ultimately intended to lead to breaking of the adhesive bond. The disadvantage of this process is that the
magnetic particles and the microcapsules are spatially separate from one another, meaning that the advantages of inductive heating are only partly translated. Furthermore, the application of the magnetic particles involves
difficulties in the form of an uneven distribution of the magnetic particles and/or an agglomeration of the magnetic particles. As a result of these effects too, the
effectiveness of inductive heating is reduced. It was therefore the object of the present invention to provide a subject matter which allows a more efficient heating of adhesive bonds than is known in the prior art.
The invention provides a microcapsule consisting of a capsule shell made of a thermoplastic resin and a
dispersion enclosed by the capsule shell which comprises magnetic particles and one or more hydrocarbons with a boiling point of -15°C to 220°C, or consists thereof, where the magnetic particles are magnetic metal oxide particles with a shell comprising silicon dioxide,
preferably a shell consisting of silicon dioxide, and the coated metal oxide particles have an average primary particle diameter of from 2 to 100 nm, preferably 10 to 80 nm and particularly preferably 20 to 70 nm, and where the average diameter of the microcapsules is 5 to 50 ym, preferably 10 to 30 ym.
In this connection, magnetic metal oxide particles are to be understood as meaning those which have ferromagnetic, ferrimagnetic and/or superparamagnetic properties. In the presence of electrical, magnetic or electromagnetic alternating fields, these particles lead to a heating of the dispersion located in the microcapsule and thus to an expansion of the microcapsule.
The coated metal oxide particles may be isolated
individual particles or aggregated particles. The
aggregated particles may be present here in a form in which metal oxide particles have become intergrown and the shell surrounds the intergrown metal oxide particles.
Furthermore, there is the possibility that the coated metal oxide particles have become intergrown via their shell. Preferably, the microcapsule according to the invention can comprise, essentially or exclusively, such coated metal oxide particles, in which the metal oxide particles have become intergrown and the shell surrounds the intergrown metal oxide particles. The average diameter of the microcapsules according to the invention can increase upon heating to 80 to 220°C by a hundred times, preferably by 40 to 80 times, the original average diameter without leading to destruction of the microcapsule . The thickness of the microcapsule according to the
invention is preferably 1 to 10 mm, particularly
preferably 4 to 8 mm.
Furthermore, preference is given to an embodiment in which the fraction of the coated metal oxide particles is 0.001 to 5% by weight, based on the microcapsule. As a rule, a
fraction of from 0.01 to 1% by weight is adequate for an expansion of the microcapsule by a factor of 40 to 80 in the presence of electromagnetic alternating fields.
In this connection, the fraction of the coated metal oxide particles, based on the dispersion, can be 0.1 to 10% by weight, preferably 0.5 to 5.
The metal oxide particles present in the microcapsule according to the invention are preferably selected from the group consisting of the oxides of cobalt, chromium, dysprosium, iron, erbium, gadolinium, holmium, nickel and terbium. Within the context of the invention, ferrites are also considered to be metal oxides. These may be for example ferrites of the general formula MFe2<04, where M = Ca, Cd, Co, Cu, Mg, Ni or Zn. Preferably, the metal oxides are iron oxides, such as haematite, magnetite and
maghemite. These may be present individually or in the form of a mixture.
In particular, preference is given to a microcapsule in which the coated metal oxide particles have a) a BET surface area of from 10 to 80 m2/g, b) a thickness of the shell of from 2 to 30 nm and c) a content of iron oxide of from 60 to 90% by weight and of silicon dioxide of from 10 to 40% by weight, in each case based on the coated metal oxide particles. Furthermore, metal oxide particles may also be present, the shell of which has been surface-modified. These can be obtained by treating the coated metal oxide particles with a surface-modifying agent, in particular one with which a
hydrophobicization of the surface results. By virtue of this measure, the stability of the dispersion in the inside of the microcapsule can be improved.
Preferred surface-modifying agents may be in particular the following silanes:
Organosilanes (RO) 3 S 1 (CnH2n+i) and (RO) 3 Si (CnH2n-i) where R = alkyl, such as methyl, ethyl, n-propyl, isopropyl, butyl and n = 1-20.
Organosilanes R ' x (RO) ySi (CnH2n+i) and R ' x (RO) ySi (CnH2n-i) where R = alkyl, such as methyl, ethyl, n-propyl, isopropyl, butyl; R' = alkyl, such as methyl, ethyl, n-propyl, isopropyl, butyl; R' = cycloalkyl; n = 1-20; x + y = 3, x = 1 , 2; y = l, 2.
Haloorganosilanes X3 S 1 (CnH2n+i) and X3 S 1 (CnH2n_i) where X = CI, Br; n = 1-20.
Haloorganosilanes X2 (R ' ) Si (CnH2n+1) and X2 (R ' ) Si (CnH2n-i) where X = CI, Br, R' = alkyl, such as methyl, ethyl, n-propyl, isopropyl, butyl;
R' = cycloalkyl; n = 1-20. Haloorganosilanes X (R ' ) 2Si (CnH2n+1) and X (R ' ) 2Si (CnH2n_i) where X = CI, Br; R' = alkyl, such as methyl, ethyl, n-propyl, isopropyl, butyl; R' = cycloalkyl; n = 1-20.
Organosilanes (RO) 3 S 1 (CH2) m-R ' where R = alkyl, such as methyl, ethyl, propyl; m = 0, 1-20; R' = methyl, aryl such as -C6H5, substituted phenyl radicals, C4F9, OCF2-CHF-CF3, C6F13, OCF2CHF2, Sx- (CH2)3Si (OR)3;
Organosilanes (R" ) x (RO) ySi (CH2) m-R ' where R" = alkyl, x + y = 3; cycloalkyl,
x = 1, 2, y = 1, 2; m =0, 1 to 20; R' = methyl, aryl, such as C6H5, substituted phenyl radicals, C4F9, OCF2-CHF-CF3, C6F13, OCF2CHF2, Sx- (CH2) 3S1 (OR) 3, SH, NR ' R ' ' R ' ' ' where R' = alkyl, aryl; R' ' = H, alkyl, aryl; R' ' ' = H, alkyl, aryl, benzyl, C2H4NR' ' ' ' R ' ' ' ' ' where R ' ' ' ' = H, alkyl and
R ' ' ' ' ' = H, alkyl .
Haloorganosilanes X3Si (CH2) m-R ' X = CI, Br; m = 0, 1-20; R' = methyl, aryl such as ΟδΗ5, substituted phenyl
radicals, C4F9, OCF2-CHF-CF3, C6F13, 0-CF2-CHF2,
Sx- (CH2) 3S1 (OR) 3, where R = methyl, ethyl, propyl, butyl and x = 1 or 2, SH.
Haloorganosilanes RX2Si (CH2) mR ' where X = CI, Br; m = 0, 1- 20; R' = methyl, aryl such as 06¾, substituted phenyl radicals, C4F9, OCF2-CHF-CF3, C6F13, 0-CF2-CHF2,
-OOC (CH3) C=CH2, -Sx- (CH2) 3Si (OR) 3, where R = methyl, ethyl, propyl, butyl and x = 1 or 2, SH.
Haloorganosilanes R2XSi (CH2) mR ' where X = CI, Br; m = 0, 1- 20; R' = methyl, aryl such as 06¾, substituted phenyl radicals, C4F9, OCF2-CHF-CF3, C6F13, 0-CF2-CHF2,
-Sx- (CH2) 3S1 (OR) 3, where R = methyl, ethyl, propyl, butyl and x = 1 or 2, SH.
Furthermore, silazanes of the general formula
R ' R2SiNHSiR2R ' where R, R' = alkyl, vinyl, aryl, can be used as surface-modifying agents.
The cyclic polysiloxanes D3, D4, D5 and also polysiloxanes and silicone oils can also be used. In this connection, D3, D4 and D5 are to be understood as meaning cyclic
polysiloxanes having 3, 4 or 5 units of the type
-O-Si (CH3)2.
The following substances can preferably be used as
surface-modifying agents: octyltrimethoxysilane,
octyltriethoxysilane .
Hexamethyldisilazane, octyltriethoxysilane and
dimethylpolysiloxanes can be used particularly
preferably .
Besides the coated metal oxide particles, the dispersion in the inside of the microcapsule also comprises one or more hydrocarbons having a boiling point of from -15°C to 220°C. Within the context of the invention, hydrocarbon is also intended to include a halogenated hydrocarbon.
Examples which may be mentioned are isobutane, n-butane, n-pentane, isopentane, n-hexane, cyclohexane, n-heptane, petroleum ether, neopentane, propane, propene, butene, CH3C1, CH2CI2, CHCI3, CCI4, CCI3F, CC12F2, CCIF3, CCIF2-CCIF2, CH2FCF3, CH3CHF2 and CHF2CF3.
The capsule shell of the microcapsule according to the invention is a thermoplastic resin. It can be obtained from one or more polymerizable monomers, the monomers being selected from the group consisting of acrylamide, acrylonitrile, acrylic acid, benzyl methacrylate,
cyclohexyl methacrylate, methacrylamide,
methacrylonitrile, methacrylic acid, methyl methacrylate,
N, -dimethylacrylamide, N, -dimethylmethacrylamide, tert- butyl methacrylate and N-vinylpyrrolidone .
In addition, one or more polymerizable crosslinking monomers having two or more polymerizable double bonds may
be present. Examples thereof are ethylene glycol
di (meth) acrylate, propylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, 1 , 4-butanediol
di (meth) acrylate, 1 , 6-hexanediol di (meth) acrylate,
trimethylolpropane tri (meth) acrylate, glycerol
di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylates , 1 , 3-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate,
1, 10-decanediol di (meth) acrylate, pentaerythritol
tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, 3-acryloyloxyglycerol monoacrylate, dimethyloltricyclodecane di (meth) acrylate and triarylformal tri (meth) acrylate .
The invention further provides a process for producing the microcapsule according to the invention, in which a) an organic dispersion which comprises coated metal
oxide particles having an average primary particle diameter of from 2 to 100 nm, the shell of which comprises amorphous silicon dioxide, b) an aqueous solution or water c) and one or more monomers, if appropriate in the
presence of one or more polymerization catalysts, are subjected to a dispersion polymerization.
Of suitability as polymerization catalyst in both variants are, for example, peroxides, such as benzoyl peroxide, tert-butyl perbenzoate, cumyl hydroperoxides, tert-butyl peracetate, lauryl peroxide and diisopropyl
peroxydicarbonate, azonitriles, such as
azobisdimethylvaleronitrile and azobisisobutyronitrile,
and also azo compounds such as azoamide compounds and alkylazo compounds.
The dispersion polymerization preferably takes place at temperatures of from 40 to 80°C. Preference is likewise given to an embodiment in which the dispersion polymerization is carried out under shearing conditions at an energy density of at least 1000 KJ/m3.
The invention further provides the use of the
microcapsules in the presence of electromagnetic
alternating fields for the breaking ("debonding") of adhesive bonds, such as fixed glazings or boards, as a constituent of coating compositions, such as paints or inks, for the filling of cracks, in the processing of thermoplasts , as a constituent of thermosets, as a constituent of paper products and in technical textile fabrics .
Claims
1. Microcapsule consisting of a capsule shell made of a thermoplastic resin and a dispersion enclosed by the capsule shell which comprises magnetic particles and one or more hydrocarbons with a boiling point of -15°C to 220°C, characterized in that the magnetic particles are magnetic metal oxide particles with a shell comprising silicon dioxide and the coated metal oxide particles have an average primary particle diameter of from 2 to 100 nm and where the average diameter of the microcapsule is 5 to 50 ym.
2. Microcapsule according to Claim 1, characterized in that its thickness is 1 to 10 mm.
3. Microcapsule according to Claims 1 or 2, characterized in that the fraction of the coated metal oxide
particles is from 0.001 to 5% by weight, based on the microcapsule .
4. Microcapsule according to Claims 1 to 3, characterized in that the fraction of the coated metal oxide
particles, based on the dispersion, is 0.1 to 10% by weight .
5. Microcapsule according to Claims 1 to 4, characterized in that the core of the coated metal oxide particles consists of one or more iron oxides comprising
haematite, magnetite and maghemite.
6. Microcapsule according to Claims 1 to 5, characterized in that the coated metal oxide particles have a) a BET surface area of from 10 to 80 m2/g, b) a thickness of the shell of from 2 to 30 nm and c) a content of iron oxide of from 60 to 90% by
weight and of silicon dioxide of from 10 to 40% by weight, in each case based on the core/shell particles.
7. Microcapsule according to Claims 1 to 6, characterized in that the shell of the metal oxide particles is surface-modified .
8. Microcapsule according to Claims 1 to 7, characterized in that the hydrocarbon is selected from the group consisting of isobutane, n-butane, n-pentane,
isopentane, n-hexane, cyclohexane, n-heptane, petroleum ether, neopentane, propane, propene, butene, CH3C1, CH2C12, CHCI3, CCI4, CCI3F, CCI2F2, CCIF3, CCIF2-CCIF2, CH2FCF3, CH3CHF2 and CHF2CF3 C.
9. Microcapsule according to Claims 1 to 8, characterized in that the capsule shell is obtained from one or more polymerizable monomers, where the monomers are selected from the group consisting of acrylamide, acrylonitrile, acrylic acid, benzyl methacrylate, cyclohexyl
methacrylate, methacrylamide, methacrylonitrile, methacrylic acid, methyl methacrylate,
N, -dimethylacrylamide, N, -dimethylmethacrylamide, tert-butyl methacrylate and N-vinylpyrrolidone .
10. Microcapsule according to Claim 9, characterized in
that the capsule shell is additionally obtained from one or more polymerizable crosslinking monomers having two or more polymerizable double bonds.
11. Process for producing the microcapsule according to Claims 1 to 10, characterized in that a) an organic dispersion which comprises coated
metal oxide particles having an average primary particle diameter of from 2 to 100 nm, the shell of which comprises amorphous silicon dioxide, b) an aqueous solution or water and c) one or more monomers, if appropriate in the
presence of one or more polymerization catalysts , are subjected to a dispersion polymerization.
12. Process according to Claim 11, characterized in that the dispersion polymerization is carried out at
temperatures of from 40 to 80°C.
13. Process according to Claims 11 or 12, characterized in that the polymerization is carried out under shearing conditions at an energy density of at least 1000 KJ/m3.
14. Use of the microcapsules according to Claims 1 to 10 in the presence of electromagnetic alternating fields for the breaking of adhesive bonds such as fixed glazings or boards, as a constituent of coating compositions, for the filling of cracks, in the processing of
thermoplasts , as a constituent of thermosets, as a constituent of paper products and in technical textile fabrics .
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102009047718 | 2009-12-09 | ||
DE102009047718.7 | 2009-12-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2011069771A1 true WO2011069771A1 (en) | 2011-06-16 |
Family
ID=43385628
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2010/067286 WO2011069771A1 (en) | 2009-12-09 | 2010-11-11 | Heat-expandable microcapsules comprising magnetic metal oxide particles |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2011069771A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103446965A (en) * | 2013-09-09 | 2013-12-18 | 青岛科技大学 | Preparation method of nickel-doped alpha-Fe2O3 multi-level structure spinous microspheres |
CN115368695A (en) * | 2022-08-08 | 2022-11-22 | 贵州师范大学 | Functional thermal expansion type foaming microcapsule and preparation method and application thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6106946A (en) | 1996-03-15 | 2000-08-22 | Matsumoto Yushi-Seiyaku Co., Ltd. | Microcapsule containing magnetic fluid, manufacturing method, and use thereof |
EP1185594A1 (en) | 1999-06-02 | 2002-03-13 | Peter Stewart Bain | Adhesive composition comprising thermoexpandable microcapsules |
US20040249037A1 (en) * | 2001-11-13 | 2004-12-09 | Jana Kolbe | Curable bonded assemblies capable of being dissociated |
WO2006042782A1 (en) | 2004-10-18 | 2006-04-27 | Tesa Ag | Process for recycling electronic components |
-
2010
- 2010-11-11 WO PCT/EP2010/067286 patent/WO2011069771A1/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6106946A (en) | 1996-03-15 | 2000-08-22 | Matsumoto Yushi-Seiyaku Co., Ltd. | Microcapsule containing magnetic fluid, manufacturing method, and use thereof |
EP1185594A1 (en) | 1999-06-02 | 2002-03-13 | Peter Stewart Bain | Adhesive composition comprising thermoexpandable microcapsules |
US20040249037A1 (en) * | 2001-11-13 | 2004-12-09 | Jana Kolbe | Curable bonded assemblies capable of being dissociated |
WO2006042782A1 (en) | 2004-10-18 | 2006-04-27 | Tesa Ag | Process for recycling electronic components |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103446965A (en) * | 2013-09-09 | 2013-12-18 | 青岛科技大学 | Preparation method of nickel-doped alpha-Fe2O3 multi-level structure spinous microspheres |
CN115368695A (en) * | 2022-08-08 | 2022-11-22 | 贵州师范大学 | Functional thermal expansion type foaming microcapsule and preparation method and application thereof |
CN115368695B (en) * | 2022-08-08 | 2023-09-19 | 贵州师范大学 | Application method of functional thermal expansion type foaming microcapsule |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4541703B2 (en) | Method for heating nanoparticulate composition and method for forming and dissociating nanoparticulate composition-containing adhesive layer | |
JP2005534720A5 (en) | Nanoparticulate composition | |
Palimi et al. | Surface modification of Fe2O3 nanoparticles with 3-aminopropyltrimethoxysilane (APTMS): An attempt to investigate surface treatment on surface chemistry and mechanical properties of polyurethane/Fe2O3 nanocomposites | |
Lü et al. | Thermosensitive poly (N-isopropylacrylamide)-grafted magnetic nanoparticles for efficient treatment of emulsified oily wastewater | |
US9290641B2 (en) | Composite material comprising polyethylene and magnetic particles | |
US8025756B2 (en) | Method of bonding materials of construction using nanoscale, superparamagnetic poly(meth)acrylate polymers | |
CN102471240A (en) | Method for producing cyanoacrylate esters in the presence of transition metal catalysts | |
JP2004506293A (en) | Ferromagnetic resonance excitation and its use for heating particle-filled substrates | |
EP1817780A1 (en) | Formulation comprising a polymerizable monomer and/or a polymer and, dispersed therein, a superparamagnetic powder | |
CA2642584A1 (en) | Nanoscale superparamagnetic poly(meth)acrylate polymers | |
WO2017060311A1 (en) | Method for preparing composite particles comprising a magnetic core and a photocatalytically active coating, and composite particles obtainable by said method | |
JP2013014716A (en) | Inorganic particle-containing foam | |
WO2011069771A1 (en) | Heat-expandable microcapsules comprising magnetic metal oxide particles | |
Guo et al. | Facile monomer stabilization approach to fabricate iron/vinyl ester resin nanocomposites | |
RU2719833C1 (en) | Coated propping agents for formation hydraulic fracture during production | |
WO2009146252A1 (en) | Filled nanoparticles | |
CN109096499B (en) | Superparamagnetic nano magnetic bead, preparation method thereof and application of controllable emulsification/demulsification performance | |
Wang et al. | Synthesis and characterization of SiO2/(PMMA/Fe3O4) magnetic nanocomposites | |
Daradmare et al. | Epoxy–8-HQ@ PS/GO composite coatings: Size effect and the loading of fillers on the self-healing and passive protection | |
KR20110069785A (en) | Method for producing hydrophilized microparticles, and hydrophilized microparticles produced by the method | |
Billon et al. | Surface-initiated nitroxide-mediated polymerization | |
EP3649208A2 (en) | Core-shell nanoparticles and their use in adhesive formulations | |
Davies et al. | Magnetically activated adhesives: towards on-demand magnetic triggering of selected polymerisation reactions | |
WO2022039676A1 (en) | Induction heating-cured adhesives | |
Hritcu et al. | Novel hybrid coatings with controlled wettability by composite nanoparticle aggregation |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10776109 Country of ref document: EP Kind code of ref document: A1 |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10776109 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 10776109 Country of ref document: EP Kind code of ref document: A1 |