WO2022117786A1 - Strukturiertes material - Google Patents
Strukturiertes material Download PDFInfo
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- WO2022117786A1 WO2022117786A1 PCT/EP2021/084110 EP2021084110W WO2022117786A1 WO 2022117786 A1 WO2022117786 A1 WO 2022117786A1 EP 2021084110 W EP2021084110 W EP 2021084110W WO 2022117786 A1 WO2022117786 A1 WO 2022117786A1
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- Prior art keywords
- composition
- bubbles
- azo compound
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- 239000000463 material Substances 0.000 title claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 61
- -1 azo compound Chemical class 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 40
- 238000010438 heat treatment Methods 0.000 claims abstract description 23
- 230000003287 optical effect Effects 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims description 23
- 239000003999 initiator Substances 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 15
- 238000000354 decomposition reaction Methods 0.000 claims description 12
- 239000004094 surface-active agent Substances 0.000 claims description 12
- 239000011159 matrix material Substances 0.000 claims description 7
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- 239000012949 free radical photoinitiator Substances 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 35
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 28
- 230000005855 radiation Effects 0.000 description 25
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
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- 238000005187 foaming Methods 0.000 description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
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- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 13
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- 238000001878 scanning electron micrograph Methods 0.000 description 9
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- 238000003847 radiation curing Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
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- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 4
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- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 3
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
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- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 239000007783 nanoporous material Substances 0.000 description 3
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 3
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- VUIMBZIZZFSQEE-UHFFFAOYSA-N 1-(1h-indol-3-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CNC2=C1 VUIMBZIZZFSQEE-UHFFFAOYSA-N 0.000 description 2
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- GZPRASLJQIBVDP-UHFFFAOYSA-N 2-[[4-[2-[4-(oxiran-2-ylmethoxy)cyclohexyl]propan-2-yl]cyclohexyl]oxymethyl]oxirane Chemical compound C1CC(OCC2OC2)CCC1C(C)(C)C(CC1)CCC1OCC1CO1 GZPRASLJQIBVDP-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 2
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- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 2
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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- DHCIAVVQOMVUPC-UHFFFAOYSA-N 1-(3,4-diacetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C(C(C)=O)=C1 DHCIAVVQOMVUPC-UHFFFAOYSA-N 0.000 description 1
- SKBBQSLSGRSQAJ-UHFFFAOYSA-N 1-(4-acetylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)=O)C=C1 SKBBQSLSGRSQAJ-UHFFFAOYSA-N 0.000 description 1
- YZRCTUCUGYQYOS-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)-2-phenylethanone Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)CC1=CC=CC=C1 YZRCTUCUGYQYOS-UHFFFAOYSA-N 0.000 description 1
- ZEFQETIGOMAQDT-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)propan-1-one Chemical compound C1=CC(C(=O)CC)=CC=C1N1CCOCC1 ZEFQETIGOMAQDT-UHFFFAOYSA-N 0.000 description 1
- QKNQPCLQRXMWJO-UHFFFAOYSA-N 1-(tert-butyldiazenyl)cyclohexane-1-carbonitrile Chemical compound CC(C)(C)N=NC1(C#N)CCCCC1 QKNQPCLQRXMWJO-UHFFFAOYSA-N 0.000 description 1
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- 239000005056 polyisocyanate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
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
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/06—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent
- C08J9/10—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing nitrogen, the blowing agent being a compound containing a nitrogen-to-nitrogen bond
- C08J9/102—Azo-compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F120/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F120/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F120/10—Esters
- C08F120/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F120/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/04—Azo-compounds
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/28—Treatment by wave energy or particle radiation
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/245—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing a polymeric component
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- 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
- C08J2201/00—Foams characterised by the foaming process
-
- 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
- C08J2203/00—Foams characterized by the expanding agent
- C08J2203/04—N2 releasing, ex azodicarbonamide or nitroso compound
-
- 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
- C08J2205/00—Foams characterised by their properties
- C08J2205/04—Foams characterised by their properties characterised by the foam pores
- C08J2205/044—Micropores, i.e. average diameter being between 0,1 micrometer and 0,1 millimeter
-
- 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
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
-
- 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
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J2333/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2333/06—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J2333/10—Homopolymers or copolymers of methacrylic acid esters
-
- 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
- C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters
- C08J2333/14—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
Definitions
- the invention relates to the production of structured materials, in particular optical materials with fine bubbles.
- Nanoporous materials have always drawn scientific attention to various applications such as : B. lightweight materials with low cost, membranes, heat or heat insulators, etc. Nanoporous materials could also prevent the cracks from propagating and lower the refractive index of polymer materials.
- a P - y (Equation 1) where AP is the pressure difference between the inside and outside of a spherical bubble of radius r and y is the surface tension.
- thermoplastic foaming process using physical or chemical blowing agents.
- Supercritical CO2 is one of the most widely used physical blowing agents.
- the foaming process is accomplished either by a rapid pressure drop in an autoclave or by transferring CO2-soaked materials to a bath above the glass transition temperature (T g ) of the materials triggered. Due to the absorptivity under the different external pressure or temperature, supersaturated CO2 is physically desorbed in the polymer matrix and starts to generate a foam structure.
- T g glass transition temperature
- the mean diameter of the foamed polystyrene which is reached at 80 °C by rapidly releasing the pressure of 380 bar, is in the range of 2 to 3 pm (I.
- the object of the invention is to specify a method which allows fine bubbles to be produced in a polymer, a material comprising such bubbles, and its use.
- the object is achieved by a method for producing structured materials comprising the steps: a) providing a curable composition comprising: a1) at least one monomer comprising at least one polymerizable or polycondensable group; a2) at least one initiator for the polymerization or polycondensation of the monomer; a3) at least one azo compound; b ) curing the composition comprising at least one irradiation to form a structured material comprising vesicles.
- a curable composition comprising: a1) at least one monomer comprising at least one polymerizable or polycondensable group; a2) at least one initiator for the polymerization or polycondensation of the monomer; a3) at least one azo compound; b ) curing the composition comprising at least one irradiation to form a structured material comprising vesicles.
- the timing of the decomposition of the azo compound and thus the release of the nitrogen to generate the bubbles in the course of curing can be controlled. This is particularly the case when the azo compound decomposes more slowly or not at all under the activating conditions of the initiator.
- composition provided can be curable by any curing mechanism, for example physically curing, thermal curing, chemical curing or radiation curing, the composition is preferably chemical curing or radiation curing, particularly preferably radiation curing.
- the composition is preferably a radiation-curable composition that is cured by radiation.
- N electromagnetic and/or corpuscular radiation
- photoinitiators are present as initiators in the composition, which can be decomposed by light of the irradiated wavelength to form free radicals, which in turn can start a radical polymerization.
- the radiation-curable monomers are preferably monomers for acrylic acid esters, methacrylic acid esters and/or unsaturated polyester resins.
- Unsaturated polyester resins are known per se to those skilled in the art.
- the radiation-curable monomers are preferably monomers for methacrylates, acrylates, hydroxy, polyester, polyether, carbonate, epoxy or urethane (meth)acrylates and (meth)acrylated polyacrylates, some of which can optionally be amine-modified.
- Polyester (meth)acrylates are the corresponding esters of ⁇ , ⁇ -ethylenically unsaturated carboxylic acids, preferably of (meth)acrylic acid, particularly preferably of acrylic acid, with polyester polyols.
- Polyether (meth)acrylates are the corresponding esters of ⁇ , ⁇ -ethylenically unsaturated carboxylic acids, preferably of (meth)acrylic acid, particularly preferably of acrylic acid, with polyether oils.
- the polyether oils are preferably polyethylene glycol with a molar mass between 106 and 2000, preferably 106 to 1500, particularly preferably 106 to 1000, poly-1,2-propanediol with a molar mass between 134 and 1178, poly-1,3 -Propanediol with a molecular weight between 134 and 1178 and polytetrahydrofurandiol with a number-average molecular weight M n in the range from about 500 to 4000, preferably 600 to 3000, in particular 750 to 2000.
- Urethane (meth) acrylates are z. B. obtainable by reacting polyisocyanates with hydroxyalkyl (meth)acrylates and optionally chain extenders such as diols, polyols, diamines, polyamines or dithiols or polythiols.
- Urethane (meth)acrylates which are dispersible in water without the addition of emulsifiers also contain ionic and/or nonionic hydrophilic groups which, for. B. are introduced into the urethane by structural components such as hydroxycarboxylic acids.
- Epoxy (meth)acrylates are obtainable by reacting epoxides with (meth)acrylic acid.
- epoxides examples include epoxidized olefins, aromatic glycidyl ethers or aliphatic glycidyl ethers, preferably those of aromatic or aliphatic glycidyl ethers.
- Epoxidized olefins can be, for example, ethylene oxide, propylene oxide, isobutylene oxide, 1-butene oxide, 2-butene oxide, vinyl oxirane, styrene oxide or epichlorohydrin, preference being given to ethylene oxide, propylene oxide, isobutylene oxide, vinyloxirane, styrene oxide or epichlorohydrin, particularly preferably ethylene oxide or propylene oxide or epichlorohydrin and most preferably ethylene oxide and epichlorohydrin.
- aromatic glycidyl ethers are bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol B diglycidyl ether, bisphenol S diglycidyl ether, hydroquinone diglycidyl ether, alkylation products of phenol/dicyclopentadiene, e.g. 2,5-bis[ ( 2, 3 -Epoxypropoxy ) phenyl ] octahydro- 4 , 7-methano-5H-indene) (CAS No. [13446-85-0] ) ), Tris [ 4-( 2 , 3-epoxypropoxy ) phenyl ]methane isomers ) CAS no. [66072-39-7] ), phenol based epoxy novolaks (CAS no. [9003-35-4] ) and cresol based epoxy novolaks (CAS no. [37382-79-9] ) .
- aliphatic glycidyl ethers examples include 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol tetraglycidyl ether, 1,1,2,2-tetrakis[4-(2,3-epoxypropoxy)phenyl]ethane (CAS no [27043-37-4] ), diglycidyl ether of polypropylene glycol (a, w-bis ( 2 , 3-epoxy-propoxy) poly (oxypropylene) (CAS No. [16096-30-3] ) and of hydrogenated bisphenol A (2,2-bis[4-(2,3-epoxypropoxy)cyclohexyl]propane, CAS no. [13410-58-7]) .
- the epoxide (meth)acrylates preferably have a number-average molar weight M n of from 200 to 20,000, particularly preferably from 200 to 10,000 g/mol and very particularly preferably from 250 to 3000 g/mol; the content of (meth)acrylic groups is preferably 1 to 5, particularly preferably 2 to 4 per 1000 g of epoxide (meth)acrylate (determined by gel permeation chromatography with polystyrene as standard and tetrahydrofuran as eluent).
- (Meth)acrylated polyacrylates are the corresponding esters of ⁇ , ⁇ -ethylenically unsaturated carboxylic acids, preferably of (meth)acrylic acid, particularly preferably of acrylic acid, with polyacrylate polyols, obtainable by esterifying polyacrylate polyols with (meth)acrylic acid.
- Carbonate (meth)acrylates are also available with different functionalities.
- the number-average molecular weight M n of the carbonate (meth)acrylates is preferably less than 3000 g/mol, particularly preferably less than 1500 g/mol, particularly preferably less than 800 g/mol (determined by gel permeation chromatography with polystyrene as standard, tetrahydrofuran solvent).
- the carbonate (meth)acrylates are easily obtainable by transesterification of carbonic acid esters with polyhydric, preferably dihydric, alcohols (diols, e.g. hexanediol) and subsequent esterification of the free OH groups with (meth)acrylic acid or also transesterification with (meth) acrylic acid esters, such as it is described, for example, in EP 0 092 269 A1. They can also be obtained by reacting phosgene, urea derivatives with polyhydric, for example dihydric, alcohols.
- (meth)acrylates of polycarbonate polyols such as the reaction product of one of the diols or polyols mentioned and a carbonic acid ester and a hydroxyl-containing (meth)acrylate.
- Suitable carbonic acid esters are ethylene, 1,2- or 1,3-propylene carbonate, dimethyl, diethyl or dibutyl carbonate.
- Suitable hydroxyl-containing (meth)acrylates are 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 1,4-butanediol mono(meth)acrylate, neopentyl glycol mono(meth)acrylate, glycerol mono- and di(meth)acrylate, trimethylolpropane mono- and di(meth)acrylate and pentaerythritol mono-, di- and tri(meth)acrylate.
- Particularly preferred monomers are methacrylates, acrylates and modified and unmodified esters thereof.
- examples are, for example, methacrylic acid esters or acrylic acid esters.
- (meth)acrylates containing hydroxyl groups are, for example, 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 1,4-butanediol mono(meth)acrylate, neopentylglycol mono(meth)acrylate, glycerol mono - and di(meth)acrylate, trimethylolpropane mono- and di(meth)acrylate and pentaerythritol mono-, di- and tri(meth)acrylate.
- the composition comprises at least one initiator for the polymerisation or polycondensation of the monomer, preferably a photoinitiator, in particular a UV photoinitiator.
- UV photoinitiators can, for example, be photoinitiators known to those skilled in the art, e.g. those in "Advances in Polymer Science", Volume 14, Springer Berlin 1974 or in KK Dietliker, Chemistry and Technology of UV and EB Formulation for Coatings, Inks and Paints, Volume 3; Photoinitiators for Free Radical and Cationic Polymerization, P.K.T. Oldring (Eds), SITA Technology Ltd, London.
- phosphine oxides for example, phosphine oxides, benzophenones, ⁇ -hydroxy-alkyl-aryl-ketones, thioxanthones, anthraquinones, acetophenones, benzoins and benzoin ethers, ketals, imidazoles or phenylglyoxylic acids and mixtures thereof are suitable.
- photoinitiators which do not evolve any gaseous components such as nitrogen during decomposition.
- phosphine oxides are mono- or bis-acylphosphine oxides, such as those described in EP 7 508 A2, EP 57 474 A2,
- EP 196 18 720 A1 EP 0 495 751 A1 or EP 0 615 980 A2 are described, for example 2,4,6-trimethylbenzoyldiphenylphosphine oxide, ethyl 2,4,6-trimethylbenzoylphenylphosphinate or bis(2,6-dimethoxybenzoyl)- 2,4,4-trimethylpentylphosphine oxide .
- benzophenones are benzophenone, 4-aminobenzophenone, 4,4'-bis(dimethylamino)benzophenone, 4-phenylbenzophenone, 4-chlorobenzophenone, Michler's ketone, o-methoxybenzophenone, 2,4,6-trimethylbenzophenone, 4 -Methylbenzophenone, 2,4-dimethylbenzophenone, 4-isopropylbenzophenone, 2-chlorobenzo- phenone, 2,2'-dichlorobenzophenone, 4-methoxybenzophenone, 4-propoxybenzophenone or 4-butoxybenzophenone, a-hydroxy-alkyl-aryl-ketones are for example 1-benzoylcyclohexan-l-ol (1-hydroxy-cyclohexyl-phenylketone) , 2-Hydroxy-2 , 2-dimethylacetophenone, ( 2-Hydroxy-2-methyl-l-phen
- Xanthones and thioxanthones are, for example, 1O-thioxanthenone, thioxanthen-9-one, xanthen-9-one, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2,4-dichlorothioxanthone or chloroxanthenone .
- anthraquinones are ß-methylanthraquinone, tert-butylanthraquinone, anthraquinone carboxylic acid ester, benz[de]anthracene-7-one, benz[a]anthracene-7, 12-dione, 2-methylanthraxquinone,
- acetophenones are acetophenone, acetonaphthoquinone, valerophenone, hexanophenone, a-phenylbutyrophenone, p-morpholinopropiophenone, dibenzosuberone, 4-morpholinobenzophenone, p-diacetylbenzene, 4'-methoxyacetophenone, a-tetralone, 9-acetylphenanthrene, 2- Acetylphenanthrene, 3-acetylphenanthrene, 3- acetylindole, 9-fluorenone, 1- indanone, 1 , 3 , 4-triacetylbenzene , 1- acetonaphthone, 2-acetonaphthone, 2 , 2-dimethoxy-2-phenylaceto- phenone, 2 , 2- Diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 1-hydroxyaceto
- benzoins and benzoin ethers are 4-morpholinodeoxybenzoin, benzoin, benzoin isobutyl ether, benzoin tetrahydropyranyl ether, benzoin methyl ether, benzoin ethyl ether, benzoin butyl ether, benzoin isopropyl ether or 7-H-benzoin methyl ether .
- ketals are acetophenone dimethyl ketal, 2,2-diethoxyacetophenone, or benzil ketals, such as benzil dimethyl ketal.
- Phenylglyoxylic acids are described, for example, in DE 198 26 712 A1, DE 199 13 353 A1 or WO 98/33761 A1.
- Photoinitiators that can also be used are, for example, benzaldehyde, methyl ethyl ketone, 1-naphthaldehyde, triphenylphosphine, tri-o-tolylphosphine or 2,3-butanedione.
- Typical mixtures include, for example, 2-hydroxy-2-methyl-l-phenyl-propan-2-one and 1-hydroxy-cyclohexyl-phenyl ketone,
- photoinitiators are 2,4,6-trimethylbenzoyldiphenylphosphine oxide, ethyl 2,4,6-trimethylbenzoylphenylphosphinate, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, benzophenone, 1-benzoylcyclohexan-l-ol , 2-hydroxy-2,2-dimethylacetophenone and 2,2-dimethoxy-2-phenylacetophenone.
- the composition also contains at least one azo compound.
- This is a compound that releases nitrogen when activated.
- This is preferably a free-radical photoinitiator based on azo-nitriles. These compounds absorb only little in the UV range and, depending on their structure, decompose only slightly under UV radiation. In particular, they are not influenced in this way by the activation of the initiator, in particular the photoinitiator. However, it is also possible that they can be activated by correspondingly strong UV radiation.
- azo compounds examples include azobisisobutyronitrile (2,2'-azobis(2-methylpropionitrile), AIBN), azobiscyanovaleric acid (ACVA), 2,2'-azobis(2,4-dimethyl)valeronitrile (ABVN)), 2,2'-azobis-(2-methylbutyronitrile (AMBN)), 1,1'-azobis(cyclohexane-l-carbonitrile (ACCN), 1-((cyano-l-methyl-ethyl)azo) formamide (CABN), 2,2'-azobis(2-methylpropionamide) dihydrochloride (MBA), dimethyl 2,2'-azobis(2-methylpropionate (AIBME), 2,2'-azobis [2 -(2-imidazolin-2-yl)propane] dihydrochloride (AIBI), 2,2'-azobis(2,4-dimethylpentanenitrile, 1,1'-azobis(cyclohexanecarbonitrile) (ACHN),
- an azo compound which also decomposes under UV radiation
- this decomposition preferably begins at a different UV wavelength than the UV photoinitiator used.
- the photoinitiator preferably requires a longer wavelength for activation than the azo compound.
- the photoinitiator can be activated with irradiation at wavelengths of more than 400 nm, while the azo compound is only decomposed at wavelengths of less than 400 nm, preferably less than 380 nm.
- a preferred composition according to the invention therefore comprises at least one free radical UV photoinitiator and at least one free radical initiator based on azo-nitrile.
- the composition also comprises at least one surface-active agent, in particular at least one stabilizer, in particular a surfactant.
- a surfactant may include nonionic surfactants such as polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether and polyoxyethylene oleyl ether, polyoxyethylene alkyl allyl ethers such as polyoxyethylene octylphenol ether, Polyoxyethylenalkylarylether wie Polyoxyethylenoctylphenylether und Polyoxyethylennonylphenylether , Polyoxyethylen- oder Polyoxypropylen-Blockcopolymere seine, Sorbitanfettklaer wie Sorbitanmonolaurat, Sorbitanmonopalmitat , Sorbitanmonostearat , Sorbitanmonooleat , Sorbitantrioleat und Sorbitantristearat occupational Polyoxyethylensorbitanfett GmbH wie Polyoxyethylen
- organosiloxane polymers such as BYK-302, BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-370, BYK-375 and BYK-378 (trade names, products of BYK-Chemie Wesel), in particular based on polyether-modified dimethylpolysiloxanes.
- the at least one surfactant is preferably used in a content of 0 to 2% by weight, in particular 0 to 1% by weight, very particularly 0 to 0.5% by weight, based on the composition as a whole.
- compositions that can be used in the process according to the invention can additionally contain 0 to 10% by weight of other additives.
- Activators, fillers, pigments, dyes, thickeners, thixotropic agents, viscosity modifiers, plasticizers or chelating agents can be used as further additives. All components are preferably soluble in one another and form a homogeneous composition.
- the composition can additionally contain a solvent, but is preferably solvent-free.
- the composition comprises 0.01 to 5% by weight of at least one initiator, based on the composition as a whole, preferably 0.01 to 1% by weight, in particular 0.01 to 0.5% by weight. .
- the composition comprises 0.01 to 20% by weight of at least one azo compound, based on the total composition, preferably 1 to 10% by weight, in particular 2 to 8% by weight. % .
- the composition comprises 0.01 to 1% by weight of at least one initiator, based on the total composition, and 0.01 to 20% by weight of at least one azo compound, based on the total composition, preferably 1 to 10% by weight .-%, in particular 2 to 8 wt. % .
- the composition comprises 50 to 99% by weight of at least one monomer, 0.01 to 5% by weight of at least one initiator, 0.01 to 20% by weight of at least one azo compound and 0 to 2 % by weight of at least one surfactant.
- the composition comprises 50 to 99% by weight of at least one monomer, 0.01 to 1% by weight at least one initiator, 1 to 10% by weight of at least one azo compound and 0 to 1% by weight of at least one surfactant.
- the amount and type of azo compound employed is such that the volume of maximum releasable nitrogen (at STP) to volume of the composition is no more than 50:1, more preferably no more than 20:1, most especially is no more than 10:1.
- Providing the composition preferably comprises applying the composition to a surface as a coating or placing it in a mold.
- composition is then cured to form a structured material. curing the composition comprising at least one irradiation to form a structured material comprising vesicles.
- drying can be carried out. This is carried out below the decomposition temperature of the components of the composition.
- the composition can be cured under an oxygen-containing atmosphere or under an inert gas.
- Radiation curing is carried out with high-energy light, e.g. (N)IR, VIS, UV light or electron beams, preferably UV list.
- high-energy light e.g. (N)IR, VIS, UV light or electron beams, preferably UV list.
- radiation sources for radiation curing are mercury low-pressure lamps, mercury medium-pressure lamps, High-pressure lamps and fluorescent tubes, pulse lamps, metal halide lamps, LEDs or excimer lamps.
- Radiation sources are, for example, high-pressure mercury vapor lamps, lasers, pulsed lamps (flashlight) or halogen lamps or excimer radiators.
- the irradiation dose is preferably 80 to 3000 mJ/cm 2 , preferably 2700 mJ/cm 2 .
- radiation sources can also be used for curing, e.g. B. two to four .
- irradiation in several steps at different wavelengths, for example in order to selectively control the decomposition of the azo compound. It is conceivable, for example, to start only or primarily the photoinitiator and thus the polymerization of the at least one monomer in a first step and only initiate the decomposition of the azo compound in a second step by irradiation with a different wavelength.
- Irradiation can optionally also be carried out in the absence of oxygen, e.g. B. be carried out under an inert gas atmosphere. Nitrogen, noble gases, carbon dioxide or combustion gases are preferably suitable as inert gases. Furthermore, the irradiation can be done by using the coating composition transparent media is covered. Transparent media are e.g. B. plastic foils or glass .
- PET is transparent to radiation with a wavelength below 300 nm.
- photoinitiators which generate free radicals with this radiation are 2,4,6-trimethylbenzoyldiphenylphosphine oxide, ethyl 2,4,6-trimethylbenzoylphenylphosphinate and bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide.
- curing is carried out in at least one of the following ways:
- the advantage of the two-stage process is in particular that the formation of the bubbles can be observed via the temperature and the duration of the heating, which enables a better optimization of the process to a specific obtain bubble density or bubble size. This applies in particular to simultaneous heating and irradiation. As a result, the material is not yet fully polymerized when the nitrogen is released.
- the intensity and/or wavelength of the irradiation can be changed in several stages, for example in order to only start the decomposition of the azo compound after a first partial polymerization. This is particularly preferred when no heating is performed as in method 3.
- the polymerization can be initiated by irradiation with a first wavelength.
- the azo compound is decomposed by subsequent irradiation with a second wavelength. This second irradiation can also take place in addition to the first.
- the intensity of the radiation in the wavelength range of the azo compound is lower than in the range for the photoinitiator. At least multi-stage, in particular two-stage, irradiation is preferred.
- the curing step in which the azo compound is decomposed, is carried out until the bubbles are of the desired size.
- the components of the composition, monomer, photoinitiator and azo compound, and preferably also the stabilizer, if present, can be adjusted accordingly.
- the previous at least partial polymerization prevents the bubbles from enlarging too much or from Nitrogen escapes from the composition. At the same time, heavy foam formation is avoided, but fine bubbles are obtained. Thus, the viscosity of the composition increases through the polymerization of the monomer, which reduces the bubble growth induced by the azo compound.
- surfactants additionally reduces the surface tension of the composition, which favors the formation of bubbles and also reduces the diameter of the bubbles.
- the composition is heated to less than 120° C., in particular to less than 100° C., in particular to less than 70° C. This makes it possible to apply a coating structured according to the invention even to temperature-sensitive substrates.
- the duration of the heating is preferably less than one minute, in particular less than 40 seconds.
- the duration of an irradiation is preferably up to 10 minutes, preferably up to 5 minutes. This applies to a single-stage process as well as to multi-stage processes. In the case of simultaneous heating, the irradiation can last as long as the heating.
- the resulting bubbles have a refractive index of approximately 1 and can thus help reduce scattering.
- Curing is preferably carried out until bubbles with an average diameter of less than 1 ⁇ m, in particular below 500 nm, in particular below 300 nm. This can be determined by determining the mean diameter of at least 40 bubbles in a cross section of the material using an SEM.
- a transparent structured material can be obtained.
- the invention therefore relates to a structured material produced using the method according to the invention.
- Such a material comprises a polymer matrix containing a large number of closed cavities (bubbles) with a diameter of less than 1 ⁇ m, in particular less than 500 nm, particularly less than 300 nm.
- the cavities are preferably distributed in the material. This variable preferably applies to at least 50%, in particular at least 60%, very particularly at least 80% of the cavities. This information preferably applies to the maximum diameter of the cavities.
- the determination is preferably carried out by SEM based on 100 cavities in a cross section through the material, with the cavities evaluated being no more than 20 ⁇ m apart in the cross section.
- the structured material is optically transparent.
- bubbles can be detected by scattering of laser light.
- the material according to the invention can be used in many, in particular optical, applications. This applies in particular to applications where an optically transparent material with scattering properties is required.
- the material can be applied to smooth or structured surfaces as a coating, which itself can also be structured, for example embossed.
- the structured material according to the invention is particularly suitable for the production or coating of optical elements.
- optical elements are used in particular as holographic applications, light management foils, diffusers, planar gradient index lenses in imaging optics, head-up displays, head-down displays, optical waveguides, especially in optical communications and transmission technology, and optical Suitable for data storage.
- optical elements that can be manufactured include security holograms, image holograms, digital holograms for information storage, systems with components that process light wavefronts, planar waveguides, beam splitters, and lenses.
- the material according to the invention can be produced on an embossed optical structure.
- the bubbles are produced so finely that the material remains optically transparent.
- the presence of the bubbles can then be detected by scattering laser light.
- the characteristic itself cannot be copied by normal means, since the inner structure of the material cannot be copied.
- range information always includes all - not mentioned - intermediate values and all conceivable sub-intervals.
- FIG. 4 SEM images of a PHEMA film with nanobubbles, (HEMA (10 g), ABVN (0.65 g), Irgacure 819 (0.03 g) + BYK 378 (0.4 wt%)) prepolymerized with UV -Light heating on a hot plate at 110 °C for 10 s (a) low magnification, b) high magnification of the center of a) ; c) , d) e) Enlargements on surface, middle and bottom as marked in a);
- FIG. 6 shows a schematic representation of a security hologram between two glass plates 100, an embossed structure 110 and areas with nanobubbles 120;
- 2-HEMA (2-hydroxyethyl methacrylate, 98%) and AIBN (2,2'-azobis(2-methylpropionitrile) , 98%) were purchased from Sigma Aldrich.
- the UV initiator IRGACURE 819 was purchased from Ciba Specialty Chemicals AG.
- V-65 (2,2'-Azobis(2,4-dimethylvaleronitrile) was purchased from FUJIFILM Wako Chemicals, Europe GmbH.
- Surfactants of BYK-378 were purchased from BYK (BYK Additives and Instruments, Germany). All materials were readily available cleaning used.
- UV-A 20800 mW/cm 2 , UV-B 18200 mW/cm 2 , UVC 2894 mW/cm 2 , total 86300 mW /cm 2 ) were used to initiate the polymerization and the post-bubbling process, respectively.
- the mixture was placed between two glass substrates - one of them was treated with a non-stick silanization - placed using 200 ⁇ m masking tape as a spacer and then irradiated with a UV lamp (wavelength 405 nm) for 5 min. After the UV irradiation, the non-stick glass was removed.
- the film on the glass substrate was transferred to a hot plate at various temperatures above the transition temperature (Tg) of PHEMA to generate bubbles and cooled to room temperature.
- Tg transition temperature
- the various foaming conditions, ie temperature and time were determined experimentally when the films turned white (opaque). During foaming, the samples on the hot plate were placed under the optical microscope to measure nucleation and bubble growth in-situ. Another film without AIBN containing only the monomer and Irgacure was made for reference.
- a surfactant from BYK 378 (0.4% by weight) was added to the mixture.
- the foaming conditions on the hot plate were carefully controlled to the point just before the film started to turn white (opaque).
- AIBN has been replaced by ABVN.
- the mixture was partially cured under the UV lamp for 2 minutes instead of fully cured.
- the partially cured, high viscosity HEMA was then heated at 70°C, ie below the Tg of PHEMA, transferred to the hot plate and irradiated together with UV radiation (1000 W) for a further 2 min.
- UV precured PHMEA sheets remained transparent in both cases, both with AIBN and without AIBN, as shown in Figure 1(a). Since the polymerization was mainly triggered by the photoinitiator Irgacure 819 and UV radiation with a wavelength of 405 nm, AIBN, which has a main absorption maximum at 350 nm, remained mostly unreacted.
- FIG. 2 shows how nucleation begins and nuclei grow at different temperatures. Because AIBN could thermally decompose faster at higher temperature (120°C), more nuclei were formed in a short time compared to the other films heated at lower temperature (100°C). Interestingly, it was found that the growth of the pre-existing bubbles and other nucleation occurred simultaneously.
- the films become opaque due to light scattering caused by the bubbles (Also, the shape of the bubbles changes from spherical to ellipsoidal, causing the film to be stretched in the vertical direction if the heating continues for more than 1 hour). While bubble size and density could be controlled by foaming temperature and time, it was impossible to achieve ultrafine bubbles.
- the volume of HEMA monomer and PHEMA polymer is 9.35 mL (density: 1.07 g/cm 3 ) and 8.70 mL (density: 1.15 g/cm 3 ), respectively. Therefore, the volume ratio of nitrogen gas to PHEMA film is approximately 7:1.
- supercritical CO2 foaming which has a volume ratio of CO2 to PMMA of up to 180:1, the production of ultrafine bubbles by conventional chemical foaming is hardly achievable without further modifications.
- Figure 3(a) shows the effect of surfactant on bubble size.
- Byk 378 was added to the solution (10g HEMA monomer, 0.32g AIBN, 0.02g Irgacure 819, 0.4 wt% BYK 378) to reduce the surface tension and free energy required , to get the interface between a bubble and the surrounding matrix. If the foaming temperature and time are carefully controlled, it was possible to achieve only ultra-fine bubbles. The bubbles were clearly detected by SEM as shown in Figure 3(b).
- AIBN was replaced by ABVN. According to one report, ABVN generates nitrogen gases at least 3 times faster than AIBN. As a result, the foaming time could be significantly reduced from 45 seconds to 10 seconds while the density of the bubbles increased as shown in Fig.
- FIGS. 4 and 5 also show the importance of the heating time. With a heating time of more than 20 seconds at 100° C., only microbubbles were obtained.
- a PHEMA with an embossed structure was created using a commercially available embossing foil as a template.
- a mixture of HEMA and Irgacure 819 was used to copy the structure from the master sheet and was fully cured by UV radiation.
- Another mixture of HEMA, Irgacure 819, BYK 378 and ABVN was filled into the embossed structure and placed between two slides.
- the foaming process proceeded similarly as previously optimized, i.e. 2 min by UV radiation (405 nm) followed by the combination of thermal heating at 70 °C and powerful UV radiation (1000 W) for 1 min.
- the sample was tested on it whether specific diffraction patterns are observed when the laser passes through the structured area.
- the microstructure and the distribution of the nanobubbles were characterized using the SEM.
- a PLA (polylactic acid) optical fiber with a diameter of 400 pm was used.
- the end tip of the PLA wire has been hand dip coated in a mixture of HEMA, Irgacure 819, BYK 378 and ABVN in some spots.
- the dip-coated PLA wire was transferred to the N2 flow chamber and held horizontally.
- the coated area was directly irradiated with UV radiation (1000 W) while the wire was rotated continuously at room temperature.
- the outcoupling efficiency was qualitatively verified by injecting the green laser into the fiber and the scattering effect was demonstrated.
- the sample was characterized with regard to the size and distribution of the bubbles using SEM.
- the security hologram is shown schematically in FIG.
- the coating of the security marking which contained ultrafine bubbles in the embossed structure, was transparent and objects behind the coating were clearly visible, as shown in Figure 7(a).
- the linear structure of the master embossing structure was difficult to see with the naked eye. Hence it seems to be a homogeneous and clear coating.
- a linear diffraction pattern appeared on the screen when a red laser light passed through the sample as shown in Fig. 7(b).
- the SEM images show that the two areas have a different microstructure and contrast.
- ultrafine bubbles in the PHEMA film serve efficiently as scattering points, as shown in Fig. 8 shown.
- the fiber with nanobubbles and without the outcoupling coating there was a clear difference between the fiber with nanobubbles and without the outcoupling coating. This phenomenon could be explained by the SEM image of the porous PHEMA coating. The amount of scattered light could be further tuned by changing the thickness of the outcoupling coating or by changing the size of the bubbles, resulting in a tailored light-outcoupling fiber system.
- a new method to generate microbubbles and ultrafine bubbles in the transparent PHEMA using azo initiators has been described. It has been found that both reducing the surface tension of the matrix and increasing the degree of supersaturation are critical factors in the production of ultrafine bubbles. It could be shown that the foaming process can be carried out under slightly different conditions, e.g. B. by (a) thermal heating only, (b) combination of thermal heating and UV radiation, and (c) UV radiation at room temperature only.
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EP21835624.4A EP4255972A1 (de) | 2020-12-03 | 2021-12-03 | Strukturiertes material |
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- 2020-12-03 DE DE102020132126.0A patent/DE102020132126A1/de not_active Withdrawn
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2021
- 2021-12-03 JP JP2023533233A patent/JP2023551538A/ja active Pending
- 2021-12-03 US US18/038,549 patent/US20240067789A1/en active Pending
- 2021-12-03 EP EP21835624.4A patent/EP4255972A1/de active Pending
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