CN101460556B - 包含由有机硅材料涂覆的塑料材料的制品的处理方法 - Google Patents
包含由有机硅材料涂覆的塑料材料的制品的处理方法 Download PDFInfo
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- CN101460556B CN101460556B CN2007800185684A CN200780018568A CN101460556B CN 101460556 B CN101460556 B CN 101460556B CN 2007800185684 A CN2007800185684 A CN 2007800185684A CN 200780018568 A CN200780018568 A CN 200780018568A CN 101460556 B CN101460556 B CN 101460556B
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- plastic material
- aqueous solution
- phosphorus
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- transfer catalyst
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- 239000000463 material Substances 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims abstract description 35
- 239000004033 plastic Substances 0.000 title claims abstract description 34
- 229920003023 plastic Polymers 0.000 title claims abstract description 34
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 22
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000004753 textile Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 14
- 150000002500 ions Chemical class 0.000 claims description 13
- -1 ethyl trimethyl phosphate trimethylpentyl phosphorus Chemical compound 0.000 claims description 11
- 150000001408 amides Chemical class 0.000 claims description 10
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 9
- 238000006068 polycondensation reaction Methods 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 150000003818 basic metals Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052728 basic metal Inorganic materials 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 150000003839 salts Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 239000011669 selenium Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical group C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 2
- WCZKTXKOKMXREO-UHFFFAOYSA-N triethylsulfanium Chemical compound CC[S+](CC)CC WCZKTXKOKMXREO-UHFFFAOYSA-N 0.000 claims description 2
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- ROKZAMCDHKVZIQ-UHFFFAOYSA-N 1-bromo-3,3-dimethylbutane Chemical compound CC(C)(C)CCBr ROKZAMCDHKVZIQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 150000003017 phosphorus Chemical class 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims 1
- QUHDFJOEQABQQI-UHFFFAOYSA-N tetrabutylphosphanium;tetramethylphosphanium Chemical compound C[P+](C)(C)C.CCCC[P+](CCCC)(CCCC)CCCC QUHDFJOEQABQQI-UHFFFAOYSA-N 0.000 claims 1
- HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical compound CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims 1
- 229920002379 silicone rubber Polymers 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000005660 chlorination reaction Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 150000003376 silicon Chemical class 0.000 description 5
- 229920002050 silicone resin Polymers 0.000 description 5
- 238000004876 x-ray fluorescence Methods 0.000 description 5
- 229920002302 Nylon 6,6 Polymers 0.000 description 4
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- WXJVQQPLIMTRFK-UHFFFAOYSA-N C(CCC)[P](CCCC)(CCCC)CCCC Chemical compound C(CCC)[P](CCCC)(CCCC)CCCC WXJVQQPLIMTRFK-UHFFFAOYSA-N 0.000 description 2
- MSOSFUYYWGPQEI-UHFFFAOYSA-N C(CCCCCCCCCCCCCCC)[P](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(CCCCCCCCCCCCCCC)[P](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 MSOSFUYYWGPQEI-UHFFFAOYSA-N 0.000 description 2
- 241000370738 Chlorion Species 0.000 description 2
- QZHCWVOOQUPXGE-UHFFFAOYSA-N OC[P] Chemical compound OC[P] QZHCWVOOQUPXGE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910001038 basic metal oxide Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000012815 thermoplastic material Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- UCRIXEWTILHNCG-UHFFFAOYSA-N 1-ethyl-2h-pyridine Chemical compound CCN1CC=CC=C1 UCRIXEWTILHNCG-UHFFFAOYSA-N 0.000 description 1
- NVEUWWMNWPNXOC-UHFFFAOYSA-N 2,2-dimethyltridecane Chemical compound CCCCCCCCCCCC(C)(C)C NVEUWWMNWPNXOC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- AUCVMXYVKNCUAO-UHFFFAOYSA-N CCCC[P+](C)(CCCC)CCCC.N Chemical compound CCCC[P+](C)(CCCC)CCCC.N AUCVMXYVKNCUAO-UHFFFAOYSA-N 0.000 description 1
- YTNSNFSZEOAYRF-UHFFFAOYSA-N CN(C)C.P Chemical compound CN(C)C.P YTNSNFSZEOAYRF-UHFFFAOYSA-N 0.000 description 1
- MKZVKOTWQCUBHD-UHFFFAOYSA-N C[P](C)(C)C Chemical compound C[P](C)(C)C MKZVKOTWQCUBHD-UHFFFAOYSA-N 0.000 description 1
- DGWAPBBFTVKTMD-UHFFFAOYSA-N C[P](CC)(C)C Chemical compound C[P](CC)(C)C DGWAPBBFTVKTMD-UHFFFAOYSA-N 0.000 description 1
- FGJUKQXJMIRONG-UHFFFAOYSA-N C[P](CCCCC)(C)C Chemical compound C[P](CCCCC)(C)C FGJUKQXJMIRONG-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229920006020 amorphous polyamide Polymers 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- CUXQLKLUPGTTKL-UHFFFAOYSA-M microcosmic salt Chemical compound [NH4+].[Na+].OP([O-])([O-])=O CUXQLKLUPGTTKL-UHFFFAOYSA-M 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SDZQEZNDOPDYPP-UHFFFAOYSA-N n,n-dimethylmethanamine;propan-1-amine Chemical compound CCCN.CN(C)C SDZQEZNDOPDYPP-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002892 organic cations Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 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
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B44—DECORATIVE ARTS
- B44C—PRODUCING DECORATIVE EFFECTS; MOSAICS; TARSIA WORK; PAPERHANGING
- B44C1/00—Processes, not specifically provided for elsewhere, for producing decorative surface effects
- B44C1/22—Removing surface-material, e.g. by engraving, by etching
-
- 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
- C08J11/00—Recovery or working-up of waste materials
-
- 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
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
-
- 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
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
- B29B17/02—Separating plastics from other materials
- B29B2017/0213—Specific separating techniques
- B29B2017/0293—Dissolving the materials in gases or liquids
- B29B2017/0296—Dissolving the materials in aqueous alkaline solutions, e.g. NaOH or KOH
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2077/00—Use of PA, i.e. polyamides, e.g. polyesteramides or derivatives thereof, as moulding material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2083/00—Use of polymers having silicon, with or without sulfur, nitrogen, oxygen, or carbon only, in the main chain, as moulding material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- B29L2022/00—Hollow articles
- B29L2022/02—Inflatable articles
- B29L2022/027—Air bags
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/141—Feedstock
- Y02P20/143—Feedstock the feedstock being recycled material, e.g. plastics
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- General Chemical & Material Sciences (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Laminated Bodies (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Lining Or Joining Of Plastics Or The Like (AREA)
Abstract
本发明涉及一种通过使用含碱金属或碱土金属氢氧化物和相转移催化剂的水溶液处理包含由有机硅材料涂覆的塑料材料的制品的方法。本发明更特别地涉及由有机硅弹性体薄层涂覆的纺织品材料，例如尤其是用于保护车辆乘客安全的气囊型可膨胀保护袋。
Description
技术领域
本发明涉及一种通过使用含碱金属或碱土金属氢氧化物和相转移催化剂的水溶液处理包含由有机硅涂覆的塑料材料的制品的方法。本发明更特别地涉及由有机硅弹性体材料薄层涂覆的纺织品材料，例如尤其是用于保护车辆乘客安全的气囊型可膨胀保护袋。
背景技术
有许多下述这样的制品：这些制品基于热塑性材料，尤其是基于聚酰胺或聚酯，例如是纺织制品、膜或模制件类型的，它们用旨在赋予其某些性能(尤其是不渗透性和/或耐磨性)的有机硅材料涂覆。这些制品通常通过沉积可交联有机硅组合物以形成有机硅弹性体薄层来制造。
但是也面临着再利用这些制品的成分尤其是回收塑料材料的问题。这是因为机械碎裂塑料材料的有机硅材料是非常困难的。已存在实现这个目的的化学途径，但它们的缺点在于它们的实现以及它们对热塑性材料性能的损害。
因而需要开发一种实施简单的方法，以允许优化再利用这些制品，尤其是不会不利地改变或劣化塑料基质。
发明内容
申请人已经开发了一种用于通过使用包含碱金属或碱土金属氢氧化物和相转移催化剂的水溶液来再利用包含至少一种由有机硅材料涂覆的塑料材料的制品的方法，该方法没有上述缺点。这是因为，碱金属或碱土金属氢氧化物和相转移催化剂的组合使用可以实现有机硅材料与塑料材料的有效分离，而不会导致塑料材料如聚酰胺或聚酯的结构改变，尤其是它们分子量的降低。
本发明因而涉及一种用于处理包含至少一种由有机硅材料涂覆的塑料材料的制品的方法，该方法包括至少下面的步骤：
-a)所述制品利用含碱金属或碱土金属氢氧化物和相转移催化剂的水溶液进行处理，任选地通过加热进行，以将有机硅材料的全部或一部分溶解或悬浮在该水溶液中；并且
-b)从溶液中分离塑料材料。
在本发明方法的步骤a)中，有机硅材料与塑料材料分离并且以溶解的形式或悬浮的形式存在于水溶液中。
相转移催化剂是众所周知的，并且常规用于进行位于水相中的阴离子(例如氢氧离子)与有机底物之间的反应。术语“相转移催化剂”因而被理解为是指能够将阴离子从水相移动到有机相的催化剂。
根据本发明，术语“相转移催化剂”尤其被理解为是指可以将氢氧离子反应物从溶液的水相转移到有机硅的有机相的两性分子。这种催化剂尤其具有将其亲和性在水相和有机相之间分配的正抗衡离子。这些输送离子在反应发生时被反复利用，这就是为什么称为相转移催化作用的原因。
在这种方法中，氢氧离子与有机硅材料的有机硅链反应形成硅烷醇化物(silanolates)。硅烷醇化物衍生物则以溶解或悬浮的形式存在于水溶液中。
在本发明的方法中，可使用已知的相转移催化剂，尤其是在JerryMARCH的著作《Advanced Organic Chemistry(高等有机化学)》(第3版)，John Wiley & Sons，1985，第320页及之后的内容中所述的那些。
在本发明方法中使用的相转移催化剂优选鎓盐，其鎓离子尤其来源于氮、磷、砷、硫、硒、氧、碳或碘，并且与烃残基配位结合。来源于氮、磷或砷的鎓离子将是四配位的。来源于硫、硒、氧、碳或S＝O的鎓离子将是三配位的，而来源于碘的鎓离子将是二配位的。与这些不同元素配位结合的烃残基是任选取代的烷基、烯基、芳基、环烷基、芳烷基基团，两个配位的烃残基可一起形成单个的二价基团。
在本发明方法中优选使用的催化剂是铵盐、磷鎓盐、吡啶鎓盐和/或锍盐。
作为鎓离子的实例，可以提到下述阳离子：四甲基铵、三乙基甲基铵、三丁基甲基铵、三甲基丙基铵，四乙基铵、四丁基铵、四甲基磷鎓、四丁基磷鎓、乙基三甲基磷鎓、三甲基戊基磷鎓、辛基三甲基磷鎓、四苯基磷鎓、鲸蜡基三甲基磷鎓、鲸蜡基三苯基磷鎓、烷基三(羟甲基)磷鎓、正丁基三苯基磷鎓、带有含10-16个碳原子的烃链的三苯基磷鎓、N-甲基吡啶鎓、N-乙基吡啶鎓、三甲基锍、三乙基锍和三苯基锍。
与这些有机阳离子结合的阴离子的性质并不十分关键。所有“硬”或“中间”碱均适合作为阴离子。术语“硬”或“中间”碱被理解为是指与R.PEARSON在Journal of Chem.Ed.45，第581-587页(1968)中给出的传统定义相对应的任何阴离子，术语“硬”和“中间”分别具有在这个参考文件中使用的术语“硬”和“边界线(borderline)”的含义。在可构成所述鎓盐的阴离子的“硬”或“中间”碱中，可以提到下述离子：F-、Cl-、Br-、I-、PO4 3-、HPO4 2-、H2PO4 -、SO4 2-、HSO4 -和NO3 -。尤其优选氯根离子和溴根离子。
特别合适的是其四个基团是具有1-5个碳原子的烷基或苄基的铵离子。至于阴离子的选择，优选氯根离子和溴根离子。
作为催化剂特别优选的是氯化四丁铵、溴化鲸蜡基三甲基磷鎓、氯化鲸蜡基三苯基磷鎓、氯化或溴化烷基三(羟甲基)磷鎓、带有含10-16个碳原子的烃链的溴化三苯基磷鎓、氯化正丁基三苯基磷鎓。
鎓盐可以以固态或以在其溶剂之一中的溶液的形式被引入到该水溶液中，所述溶剂通常是水。
作为碱金属氢氧化物，尤其可以提及LiOH、NaOH和KOH。
通常地，在该水溶液中使用1-60％重量，优选5-50％重量，更优选10-40％重量的碱金属或碱土金属氢氧化物。该水溶液可包含0.1-10mol％，优选1-3mol％的相转移催化剂，相对于氢氧离子的摩尔数。
该塑料材料可以采取能够被有机硅材料涂覆的各种形式；并且尤其可以是纱线、纤维、纺织制品、模制件、挤出件或膜的形式。纺织制品可以是例如织造、非织造或针织的。
作为实例，可以提及用于保护车辆乘客安全的气囊、传送带、耐火织物、绝热材料、补偿器(compensateurs)如管道用柔性密封套筒、管子、膜、服装、旨在用于内部或外部纺织品建筑物中的柔性材料如防雨布、帐篷、台子以及大帐幕。
该塑料材料优选是热塑性塑料，尤其是基于聚酰胺、聚酯和/或聚烯烃。
作为聚酰胺的类型，可以提及例如半结晶或无定形聚酰胺如脂族或半芳族聚酰胺。尤其可以提及(共)聚酰胺PA-6、PA-6，6、PA-4，6、PA-6，10、PA-6，12、PA-11、PA-12和/或共混物如聚酰胺PA-6/6，6。
作为聚酯的类型，可以提及聚对苯二甲酸乙二醇酯(PET)，其不仅指仅由对苯二甲酸单体或其酯如对苯二甲酸二甲酯和乙二醇获得的均聚物，也指共聚物。
作为聚烯烃的类型，可以提及聚乙烯类和聚丙烯类。
能够被使用以形成可以向大量的塑料材料提供官能性的涂层的可交联液体有机硅配制剂有很多。可以使用各种各样的多组份、双组份或单组份聚有机硅氧烷(POS)配制剂，其在室温下或者在热条件下通过聚加成、氢化硅烷化、自由基或缩聚反应交联。应当指出：所述有机硅组合物被充分地描述于文献中，尤其是Walter NOLL的著作《Chemistry andTechnology of Silicones(有机硅化学和技术)》，Academic Press，1968，第2版中，尤其是第386至409页中。
塑料材料的有机硅涂层可以由例如有机硅油或有机硅树脂组成。
本发明的方法特别适合于再利用由有机硅材料涂覆的塑料材料，该有机硅材料在湿气作用下通过缩聚反应交联，这通常在本领域中已知的催化剂的存在下进行(参见例如申请FR2865223)。
本发明的方法的处理步骤a)可以在容器中如槽或池中进行。在这个步骤中，可任选地加热反应介质到20-100℃的温度。在这个步骤中，制品可与溶液保持接触一至数个小时，例如1-3个小时，甚至高达24个小时，这取决于涂覆所述塑料材料的有机硅材料的用量。反应介质可任选地进行搅拌。
尤其是，在处理步骤a)中可以引入研磨或切碎形式的包含至少一种由有机硅材料涂覆的塑料材料的制品。
本发明方法的步骤b)中的溶液与塑料材料的分离可以通过取出该塑料材料或者排出该水溶液来进行。该塑料材料可任选地用水洗涤和/或通过传统方式干燥。
还可以在本发明的方法中增加步骤c)，在该步骤c)中，塑料材料用酸处理，这尤其用于中和保留在所述塑料材料中的氢氧离子。为此，可以使用含有酸尤其是乙酸、甲酸、磷酸或硬脂酸或己二酸的水溶液。该材料可任选地用水洗涤和/或通过传统方法干燥。
回收的塑料材料随后可被转变成粒料。
在本说明书中使用的特定用语是为了便于理解本发明的原理。不过应当理解的是，使用这样的特定用语并不对本发明的范围造成限制。表述“和/或”包括含义“和”、“或”以及与这种表述有关的要素的其它所有可能的组合。
具体实施方式
通过下面仅仅以示意性方式给出的实施例可以更清楚本发明的其它细节或优点。
实验部分
实施例1：
将100g由涂覆了通过缩聚交联的有机硅树脂的聚酰胺66所制成的气囊片浸入20g的含1％重量氯化四丁铵的50％重量NaOH水溶液中。在60℃的温度下接触3小时后，将所述片从溶液中移出。将其用水洗涤，然后将其用含5％重量乙酸的水溶液冲洗。然后用水再洗涤，直到水的pH值为中性。
通过X-射线荧光分析可以观察到在处理之后的所述片的表面上不存在任何含硅衍生物。通过DSC的观察可以证实在处理之后聚酰胺的分子量没有变化。
实施例2(对比)
将100g由涂覆了通过缩聚/聚加成交联的有机硅树脂的聚酰胺66所制成的气囊片浸入20g的50％重量NaOH水溶液中。在60℃的温度下接触3小时后，将所述片从溶液中移出。将其用水洗涤，然后将其用含5％重量乙酸的水溶液冲洗。然后用水再洗涤，直到水的pH值为中性。
通过X-射线荧光分析可以观察到在处理之后的所述片的表面上存在全部的含硅衍生物。再取这些聚酰胺片并且使其在100℃下反应24小时。通过X-射线荧光分析可以观察到在所述片的表面上存在大部分的含硅衍生物。
实施例3
将100g由涂覆了通过缩聚/聚加成交联的有机硅树脂的聚酰胺66所制成的气囊片浸入20g的含0.5％重量氯化四丁基磷鎓的50％重量NaOH水溶液中。在100℃的温度下接触16小时后，将所述片从溶液中移出。将其用水洗涤，然后将其用含5％重量乙酸的水溶液冲洗。然后用水再洗涤，直到水的pH值为中性。
通过X-射线荧光分析可以观察到在处理之后的所述片的表面上不存在任何含硅衍生物。通过DSC的观察可以证实在处理之后聚酰胺的分子量没有变化。
实施例4
将100g由涂覆了通过缩聚/聚加成交联的有机硅树脂的聚酰胺66所制成的气囊片浸入20g的含0.5％重量氯化三甲基十二烷基磷鎓的50％重量NaOH水溶液中。在100℃的温度下接触16小时后，将所述片从溶液中移出。将其用水洗涤，然后将其用含5％重量乙酸的水溶液冲洗。然后用水再洗涤，直到水的pH值为中性。
通过X-射线荧光分析可以观察到在处理之后的所述片的表面上不存在任何含硅衍生物。通过DSC的观察可以证实在处理之后聚酰胺的分子量没有变化。
Claims (14)
1.一种用于处理包含至少一种由有机硅材料涂覆的塑料材料的制品的方法，该方法包括至少下面的步骤：
-a)所述制品利用含碱金属或碱土金属氢氧化物和相转移催化剂的水溶液进行处理，任选地通过加热进行，以将有机硅材料的全部或一部分溶解或悬浮在该水溶液中；并且
-b)从溶液中分离塑料材料，
其中该水溶液包含0.1-10mol％的相转移催化剂，相对于氢氧离子的摩尔数，
其中相转移催化剂选自
盐，其
离子来源于氮、磷、砷、硫、硒、氧、碳或碘，并且与烃残基配位结合，
其中在该水溶液中使用1-60％重量的碱金属或碱土金属氢氧化物。
2.权利要求1的方法，其特征在于在该水溶液中使用5-50％重量的碱金属或碱土金属氢氧化物。
3.权利要求1的方法，其特征在于在该水溶液中使用10-40％重量的碱金属或碱土金属氢氧化物。
4.权利要求1的方法，其特征在于相转移催化剂选自铵盐、磷
盐、吡啶
盐和/或锍盐。
5.权利要求4的方法，其特征在于相转移催化剂选自四甲基铵、三乙基甲基铵、三丁基甲基铵、三甲基丙基铵，四乙基铵、四丁基铵、四甲基磷
四丁基磷
乙基三甲基磷
三甲基戊基磷
辛基三甲基磷四苯基磷
鲸蜡基三甲基磷
鲸蜡基三苯基磷
烷基三(羟甲基)磷
正丁基三苯基磷
带有含10-16个碳原子的烃链的三苯基磷
N-甲基吡啶N-乙基吡啶
三甲基锍、三乙基锍和三苯基锍的盐。
6.权利要求1的方法，其特征在于碱金属氢氧化物选自LiOH、NaOH和KOH。
7.权利要求1-6中任一项的方法，其特征在于该塑料材料以纱线、纤维、纺织制品、模制件、挤出件或膜的形式存在。
8.权利要求1-6中任一项的方法，其特征在于该塑料材料基于聚酰胺、聚酯和/或聚烯烃。
9.权利要求1-6中任一项的方法，其特征在于该塑料材料由有机硅材料涂覆，该有机硅材料由在室温下或者在热条件下通过聚加成、氢化硅烷化、自由基或缩聚反应交联的多组份或单组份聚有机硅氧烷配制剂产生。
10.权利要求9的方法，其特征在于所述多组份聚有机硅氧烷配制剂为双组份聚有机硅氧烷配制剂。
11.权利要求1-6中任一项的方法，其特征在于该塑料材料由在催化剂存在下在湿气作用下通过缩聚反应交联的有机硅材料涂覆。
12.权利要求1-6中任一项的方法，其特征在于在步骤a)中，反应介质被加热到20-100℃的温度。
13.权利要求1-6中任一项的方法，其特征在于在步骤b)之后，塑料材料用水洗涤和/或进行干燥。
14.权利要求1-6中任一项的方法，其特征在于该方法包括：利用酸处理塑料材料并且任选地利用水洗涤和/或进行干燥的另外步骤c)。
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| BE1019650A5 (fr) * | 2010-11-22 | 2012-09-04 | Comet Traitements Sa | Procede d'elimination de derives a base de silicium d'une phase organique, en particulier dans des residus de craquage catalytique. |
| FR2973274B1 (fr) * | 2011-03-31 | 2016-05-06 | Rhodia Operations | Procede de traitement de textiles techniques |
| WO2016049898A1 (zh) * | 2014-09-30 | 2016-04-07 | 华为技术有限公司 | 身份认证的方法、装置及用户设备 |
| ES2977903T3 (es) | 2020-03-27 | 2024-09-02 | Evonik Operations Gmbh | Reciclaje de materiales de estructuras planas siliconizadas |
| US11732092B2 (en) | 2020-10-19 | 2023-08-22 | Evonik Operations Gmbh | Upcycling process for processing silicone wastes |
| US12060460B2 (en) | 2021-04-29 | 2024-08-13 | Evonik Operations Gmbh | Process for producing endcapped, liquid siloxanes from silicone wastes |
| JP7422944B2 (ja) * | 2021-09-24 | 2024-01-26 | リンテック株式会社 | 基材の分離方法 |
| JP7118485B1 (ja) | 2022-02-28 | 2022-08-16 | リファインバース株式会社 | エアバッグの処理システムおよびエアバッグの処理方法 |
| CN114573982A (zh) * | 2022-03-09 | 2022-06-03 | 广东沃府实业有限公司 | 一种基于再生pa66气囊料改性的汽车扎带材料及其制备方法 |
| JP7383093B1 (ja) | 2022-08-02 | 2023-11-17 | 信越化学工業株式会社 | シリコーンコーティング樹脂基材のリサイクル方法 |
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| GB1229210A (zh) * | 1968-03-13 | 1971-04-21 | ||
| US4161464A (en) * | 1978-03-24 | 1979-07-17 | The B. F. Goodrich Company | Devulcanized rubber composition and process for preparing same |
| JP3004415B2 (ja) * | 1991-09-12 | 2000-01-31 | アサヒビール株式会社 | プラスチック製容器、その再利用化方法及び表面処理剤 |
| EP0589642A1 (en) * | 1992-09-24 | 1994-03-30 | General Electric Company | Salvaging organic thermoplastics |
| US5384159A (en) * | 1993-09-22 | 1995-01-24 | General Electric Company | Process for restoring discharded silicone-polycarbonate parts |
| US6428738B1 (en) * | 1995-11-01 | 2002-08-06 | Patent Holding Company | Method of manufacturing an in-mold laminate component |
| US5817183A (en) * | 1996-08-12 | 1998-10-06 | General Electric Company | Method for removing coatings from thermoplastic substrates |
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| JP3956202B2 (ja) * | 2002-05-30 | 2007-08-08 | 関西電力株式会社 | シリコーン化合物の解重合法 |
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| US20050230347A1 (en) * | 2004-04-14 | 2005-10-20 | Gallas James M | Methods for tinting plastic films and sheets with melanin |
| US7248061B2 (en) * | 2004-09-14 | 2007-07-24 | Denso Corporation | Transmission device for transmitting a signal through a transmission line between circuits blocks having different power supply systems |
| US7315042B2 (en) * | 2004-11-18 | 2008-01-01 | 3M Innovative Properties Company | Semiconductors containing trans-1,2-bis(acenyl)ethylene compounds |
-
2006
- 2006-05-22 FR FR0604544A patent/FR2901278B1/fr not_active Expired - Fee Related
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2007
- 2007-05-22 CN CN2007800185684A patent/CN101460556B/zh not_active Expired - Fee Related
- 2007-05-22 WO PCT/EP2007/054915 patent/WO2007135140A1/fr active Application Filing
- 2007-05-22 EP EP07729357A patent/EP2027197B1/fr not_active Ceased
- 2007-05-22 US US12/301,500 patent/US9115261B2/en not_active Expired - Fee Related
- 2007-05-22 BR BRPI0711000-6A patent/BRPI0711000B1/pt not_active IP Right Cessation
- 2007-05-22 DE DE200760004980 patent/DE602007004980D1/de active Active
- 2007-05-22 AT AT07729357T patent/ATE458778T1/de not_active IP Right Cessation
- 2007-05-22 JP JP2009511505A patent/JP4690483B2/ja not_active Expired - Fee Related
- 2007-05-22 RU RU2008150473A patent/RU2433148C2/ru active
- 2007-05-22 KR KR1020087027812A patent/KR101411686B1/ko active IP Right Grant
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Also Published As
| Publication number | Publication date |
|---|---|
| US20100012623A1 (en) | 2010-01-21 |
| CN101460556A (zh) | 2009-06-17 |
| RU2433148C2 (ru) | 2011-11-10 |
| EP2027197A1 (fr) | 2009-02-25 |
| DE602007004980D1 (de) | 2010-04-08 |
| JP4690483B2 (ja) | 2011-06-01 |
| KR101411686B1 (ko) | 2014-06-25 |
| BRPI0711000A2 (pt) | 2011-08-23 |
| FR2901278B1 (fr) | 2008-07-04 |
| RU2008150473A (ru) | 2010-06-27 |
| TNSN08480A1 (fr) | 2010-04-14 |
| MX2008014764A (es) | 2009-01-27 |
| KR20090018908A (ko) | 2009-02-24 |
| US9115261B2 (en) | 2015-08-25 |
| JP2009537686A (ja) | 2009-10-29 |
| EP2027197B1 (fr) | 2010-02-24 |
| WO2007135140A1 (fr) | 2007-11-29 |
| ATE458778T1 (de) | 2010-03-15 |
| BRPI0711000B1 (pt) | 2017-12-05 |
| FR2901278A1 (fr) | 2007-11-23 |
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