AU2006274207B2 - Cycloolefin copolymer bottle with a scratch-resistant coating - Google Patents
Cycloolefin copolymer bottle with a scratch-resistant coating Download PDFInfo
- Publication number
- AU2006274207B2 AU2006274207B2 AU2006274207A AU2006274207A AU2006274207B2 AU 2006274207 B2 AU2006274207 B2 AU 2006274207B2 AU 2006274207 A AU2006274207 A AU 2006274207A AU 2006274207 A AU2006274207 A AU 2006274207A AU 2006274207 B2 AU2006274207 B2 AU 2006274207B2
- Authority
- AU
- Australia
- Prior art keywords
- bottle according
- group
- groups
- silane
- bottle
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 16
- 239000006120 scratch resistant coating Substances 0.000 title 1
- 229920003023 plastic Polymers 0.000 claims abstract description 22
- 239000004033 plastic Substances 0.000 claims abstract description 22
- 239000011248 coating agent Substances 0.000 claims abstract description 19
- 238000000576 coating method Methods 0.000 claims abstract description 19
- 229920000642 polymer Polymers 0.000 claims abstract description 11
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 41
- 229910000077 silane Inorganic materials 0.000 claims description 41
- -1 polypropylene Polymers 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 239000004411 aluminium Substances 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000002736 metal compounds Chemical class 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229930194542 Keto Natural products 0.000 claims description 5
- 239000004743 Polypropylene Substances 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000001925 cycloalkenes Chemical class 0.000 claims description 5
- 239000003822 epoxy resin Substances 0.000 claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- 229920001155 polypropylene Polymers 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 4
- 125000005025 alkynylaryl group Chemical group 0.000 claims description 4
- 239000003708 ampul Substances 0.000 claims description 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 4
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
- 229920001328 Polyvinylidene chloride Polymers 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 3
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
- 239000004800 polyvinyl chloride Substances 0.000 claims description 3
- 239000005033 polyvinylidene chloride Substances 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 229910006404 SnO 2 Inorganic materials 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000010936 titanium Substances 0.000 description 8
- 150000004756 silanes Chemical class 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000006748 scratching Methods 0.000 description 4
- 230000002393 scratching effect Effects 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005595 acetylacetonate group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical class CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229960004838 phosphoric acid Drugs 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000003678 scratch resistant effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- UUNGBOQAZQUJMZ-UHFFFAOYSA-N 3-bromopropyl(trichloro)silane Chemical class Cl[Si](Cl)(Cl)CCCBr UUNGBOQAZQUJMZ-UHFFFAOYSA-N 0.000 description 1
- DMNALYQQZDWQQL-UHFFFAOYSA-N 8-bromooctyl(trichloro)silane Chemical class Cl[Si](Cl)(Cl)CCCCCCCCBr DMNALYQQZDWQQL-UHFFFAOYSA-N 0.000 description 1
- JMHWNJGXUIJPKG-UHFFFAOYSA-N CC(=O)O[SiH](CC=C)OC(C)=O Chemical class CC(=O)O[SiH](CC=C)OC(C)=O JMHWNJGXUIJPKG-UHFFFAOYSA-N 0.000 description 1
- 101150012417 IL1B gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- FYTPGBJPTDQJCG-UHFFFAOYSA-N Trichloro(chloromethyl)silane Chemical class ClC[Si](Cl)(Cl)Cl FYTPGBJPTDQJCG-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical class CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- MJWPFSQVORELDX-UHFFFAOYSA-K aluminium formate Chemical compound [Al+3].[O-]C=O.[O-]C=O.[O-]C=O MJWPFSQVORELDX-UHFFFAOYSA-K 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- ZCLVNIZJEKLGFA-UHFFFAOYSA-H bis(4,5-dioxo-1,3,2-dioxalumolan-2-yl) oxalate Chemical compound [Al+3].[Al+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O ZCLVNIZJEKLGFA-UHFFFAOYSA-H 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- YHAYSVXJJPHCRO-UHFFFAOYSA-N but-3-enyl(dichloro)silane Chemical class Cl[SiH](Cl)CCC=C YHAYSVXJJPHCRO-UHFFFAOYSA-N 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- WCOATMADISNSBV-UHFFFAOYSA-K diacetyloxyalumanyl acetate Chemical compound [Al+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WCOATMADISNSBV-UHFFFAOYSA-K 0.000 description 1
- NJKDOKBDBHYMAH-UHFFFAOYSA-N dibutyl(dichloro)silane Chemical class CCCC[Si](Cl)(Cl)CCCC NJKDOKBDBHYMAH-UHFFFAOYSA-N 0.000 description 1
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical class C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 1
- RKHXNBJRDQOIOQ-UHFFFAOYSA-N dichloro(ethyl)silane Chemical class CC[SiH](Cl)Cl RKHXNBJRDQOIOQ-UHFFFAOYSA-N 0.000 description 1
- KPPHTHGHNJOVMY-UHFFFAOYSA-N dichloro(prop-2-enyl)silane Chemical class Cl[SiH](Cl)CC=C KPPHTHGHNJOVMY-UHFFFAOYSA-N 0.000 description 1
- DBWSTBGNSJEPFT-UHFFFAOYSA-N dichloro-(2-chloroethyl)-methylsilane Chemical class C[Si](Cl)(Cl)CCCl DBWSTBGNSJEPFT-UHFFFAOYSA-N 0.000 description 1
- XMLHOFONEFDPBN-UHFFFAOYSA-N diethoxy(2-phenylethenyl)silane Chemical class CCO[SiH](OCC)C=CC1=CC=CC=C1 XMLHOFONEFDPBN-UHFFFAOYSA-N 0.000 description 1
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical class CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 1
- BGMKLPCJBFXZTQ-UHFFFAOYSA-N diethoxy(prop-2-enyl)silane Chemical class CCO[SiH](CC=C)OCC BGMKLPCJBFXZTQ-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical class CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical class CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QRLBICHXRCOJDU-UHFFFAOYSA-N methyl(phenyl)silane Chemical class C[SiH2]C1=CC=CC=C1 QRLBICHXRCOJDU-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- BOYBHDHQCOROOJ-UHFFFAOYSA-N n-[butylamino(dimethyl)silyl]butan-1-amine Chemical class CCCCN[Si](C)(C)NCCCC BOYBHDHQCOROOJ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
- 229960001756 oxaliplatin Drugs 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MOOUPSHQAMJMSL-UHFFFAOYSA-N tert-butyl(trichloro)silane Chemical class CC(C)(C)[Si](Cl)(Cl)Cl MOOUPSHQAMJMSL-UHFFFAOYSA-N 0.000 description 1
- CAPIMQICDAJXSB-UHFFFAOYSA-N trichloro(1-chloroethyl)silane Chemical class CC(Cl)[Si](Cl)(Cl)Cl CAPIMQICDAJXSB-UHFFFAOYSA-N 0.000 description 1
- FLPXNJHYVOVLSD-UHFFFAOYSA-N trichloro(2-chloroethyl)silane Chemical class ClCC[Si](Cl)(Cl)Cl FLPXNJHYVOVLSD-UHFFFAOYSA-N 0.000 description 1
- SIPHWXREAZVVNS-UHFFFAOYSA-N trichloro(cyclohexyl)silane Chemical class Cl[Si](Cl)(Cl)C1CCCCC1 SIPHWXREAZVVNS-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical class Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- NYQDBZQWFXNBRZ-UHFFFAOYSA-N trichloro-(2-chlorophenyl)silane Chemical class ClC1=CC=CC=C1[Si](Cl)(Cl)Cl NYQDBZQWFXNBRZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/046—Reinforcing macromolecular compounds with loose or coherent fibrous material with synthetic macromolecular fibrous 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
- C08J2365/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Details Of Rigid Or Semi-Rigid Containers (AREA)
- Medical Preparation Storing Or Oral Administration Devices (AREA)
- Containers Having Bodies Formed In One Piece (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Paints Or Removers (AREA)
Abstract
The invention relates to a bottle made from plastic, including or made from cycloolefin copolymer, with a coating of an inorganic/organic hybrid polymer (ORMOCER coating) .
Description
WO 2007/012474 - 1 - PCT/EP2006/007374 Cycloolefin copolymer bottle having a scratch-resistant covering The invention relates to cycloolefin copolymer bottles having a scratch-resistant covering. 5 Containers made of plastics have the advantage over glass containers of being low in weight and having a high degree of break resistance. A disadvantage of plastics containers is, however, their high susceptibility to scratching. 10 Plastics bottles are frequently used for pharmaceutical preparations. For the production of the preparations, the plastics bottles are often sterilised together with the pharmaceutical preparation. Commercially available plastics bottles contain polyethylene propylene (PEP) or polypropylene (PP) and are not autoclavable but have to be radiation-sterilised or sterilised with ethylene oxide. Those plastics bottles 15 have the additional disadvantage that they are milky and for that reason visual inspection of the contents of the bottle is not possible. A bottle made of cycloolefin copolymer (COC) is clear, but is highly susceptible to scratching. The problem of the invention is to provide a clear, coated plastics bottle the outer 20 surface of which is unsusceptible to scratching. The plastics bottles should be suitable for use on the customary filling apparatus for liquid pharmaceutical preparations or pharmaceutical powders. In addition, the plastics bottle should be autoclavable. The problem underlying the invention is now solved by a bottle made of plastics, 25 comprising or consisting of cycloolefin copolymer, having a coating of an inorganic organic hybrid polymer (ORMOCER coating). Surprisingly, it has been found that plastics bottles made of cycloolefin copolymer having an ORMOCER coating are autoclavable and are not susceptible to scratching. 30 In addition, the ORMOCER covering adheres well to the COC surface. For the bottles according to the invention, the cycloolefin copolymer can be a copolymer of ethylene and cycloolefin. 35 For the bottles according to the invention, the ethylene can be unsubstituted or substituted.
WO 2007/012474 - 2 - PCT/EP2006/007374 Furthermore, for the bottle according to the invention, the cycloolefin can be dicyclopentadiene or a dicyclopentadiene derivative. 5 For the bottle according to the invention, the dicyclopentadiene or dicyclopentadiene derivative can be unsubstituted or substituted. Furthermore, for the bottle according to the invention, the plastics can comprise or consist of a mixture of the cycloolefin polymer and a polymer from the group formed 10 by polypropylene, polyvinyl chloride and polyvinylidene chloride. Furthermore, the bottle according to the invention can be provided with a hybrid polymer coating comprising or consisting of (i) a hydrolytic condensate, preparable from a silane of the formula RmSiX 4 -m having 15 the following meanings: R = crosslinkable organic radical X = hydrolysable and condensable group m = 1 or 2 or 3 (with 1 being preferred) with a metal compound, 20 (ii) a prepolymer that is crosslinkable with the radicals R of the silane, (iii) one or more (especially one or two) optional non-crosslinkable organofunctional silane(s) and (iv) an optional low-volatility oxide. 25 For the bottle according to the invention, R in the silane formula can be a radical from the group formed by alkyl, alkenyl, alkynyl, aryl, arylalkyl, alkylaryl, arylalkenyl, alkenylaryl, arylalkynyl and alkynylaryl, it being possible for those radicals to be interrupted one or more times by an 0 atom and/or an S atom and/or an N atom and/or by an NH group, or to have a terminal OH, SH or NH 2 group. 30 For the bottle according to the invention, the radicals R in the silane formula can be, independently of one another, an unsubstituted radical or a radical substituted by one or more substituents from the group formed by halogen atoms, unsubstituted amino, amide, aldehyde, keto, alkylcarbonyl, carboxy, mercapto, cyano, isocyano, cyanato, 35 isocyanato, hydroxy, alkoxy, alkoxycarbonyl, sulfonic acid, phosphoric acid, acrylic, WO 2007/012474 - 3 - PCT/EP2006/007374 acryloxy, methacrylic, methacryloxy, glycidyl, glycidyloxy, epoxy and vinyl groups and such groups in substituted form. For the bottle according to the invention, the radicals X in the silane formula can be, 5 independently of one another, alkoxy groups, aryloxy groups, acyloxy groups, alkyl carbonyl groups, alkoxycarbonyl groups, hydroxy groups, halogen, hydrogen or substituted or unsubstituted amino groups. For the bottle according to the invention, a prepolymer can be provided which carries 10 a group R as reactive group, R having a meaning as detailed above. Thus, for the bottle according to the invention a prepolymer can be provided which carries a group R as reactive group, R in the prepolymer and in the silane having the same meaning. 15 Furthermore, for the bottle according to the invention the silane and the prepolymer can be a combination as follows: (i) silane having epoxy groups with epoxy resin as prepolymer and/or (ii) silane having vinyl radicals with prepolymer having crosslinkable double bonds 20 and/or (iii) silane having polymerisable double bonds with prepolymer having crosslinkable double bonds and/or (iv) mercapto-group-containing silane with prepolymer having crosslinkable double bonds and/or 25 (v) isocyanate-group-containing silane with polyol as prepolymer and/or (vi) hydroxyl-group-containing silane with isocyanate as prepolymer and/or (vii) amino-group-containing silane with epoxy resin as prepolymer. Thus, the bottle according to the invention can be provided with a hydrolytic 30 condensate of an acrylic-group-containing silane and with a prepolymer acrylate. Furthermore, for the bottle according to the invention an optional non-crosslinkable organofunctional silane of the formula R'mSiX 4 -m having the following meanings can be provided: 35 R' = non-crosslinkable organic radical X = hydrolysable and condensable group WO 2007/012474 -4 - PCT/EP2006/007374 m = 1 or 2 or 3. For the bottle according to the invention, R' in the silane formula can be a radical from the group formed by alkyl, cycloalkyl, aryl, arylalkyl and alkylaryl, it being possible for 5 those radicals to be interrupted one or more times by an 0 atom and/or an S atom and/or an N atom and/or by an NH group or to have a terminal OH, SH or NH 2 group. Furthermore, for the bottle according to the invention, the radicals R' in the silane formula can be, independently of one another, an unsubstituted radical or a radical 10 substituted by one or more substituents from the group formed by halogen atoms, unsubstituted amide, aldehyde, keto, alkylcarbonyl, carboxy, cyano, alkoxy and alkoxycarbonyl groups and such groups in substituted form. Furthermore, for the bottle according to the invention the radicals X in the silane 15 formula R'mSiX 4 -m can be, independently of one another, alkoxy groups, aryloxy groups, alkylcarbonyl groups, alkoxycarbonyl groups, hydroxy groups, halogen, hydrogen or substituted or unsubstituted amino groups. Furthermore, for the bottle according to the invention a low-volatility oxide of 20 compounds of elements of main group la, Ila, Ilia, IVa and/or Va or of sub-group 1lb, Il1b, Vb, VIb, Vllb and/or VIllb, with the exception of aluminium, can be provided. Thus, for the bottle according to the invention B 2 0 3 , P 2 0 5 and/or SnO 2 can be provided. 25 Furthermore, the bottle according to the invention can be provided with ABRASIL GA2-30, ABRASIL GA2-35 or ABRASIL VM-26-IPA2 as coating material. Furthermore, the bottle according to the invention can have a cylindrical or prismatic 30 or square shape. Furthermore, the bottle according to the invention can be an injection bottle, a screw closure bottle or an ampoule. 35 Furthermore, the bottle according to the invention can be an injection bottle or screw closure bottle having a volume of from 1 to 1000 ml.
WO 2007/012474 - 5 - PCT/EP2006/007374 Furthermore, the bottle according to the invention can be an injection bottle having a volume of from 2 to 100 ml. 5 Furthermore, the bottle according to the invention can be an ampoule having a volume of from 1 to 20 ml. Furthermore, the bottle according to the invention can be provided with a coating having a thickness of from 1 to 100 pm, especially from 2 to 30 pm and preferably 10 from 8 to 20 pm. Finally, the bottle according to the invention can be provided filled with a pharma ceutical preparation and closed with a closure. 15 The invention is described in greater detail below. The term alkyl refers to a saturated, straight-chain or branched hydrocarbon group having especially from 1 to 20 carbon atoms, preferably from 1 to 12 carbon atoms, more especially from 1 to 6 carbon atoms, for example the methyl, ethyl, propyl, 20 isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, 2,2-dimethylbutyl or n-octyl group. The terms alkenyl and alkynyl refer to at least partially unsaturated, straight-chain or branched hydrocarbon groups having especially from 2 to 20 carbon atoms, prefer ably from 2 to 12 carbon atoms, more especially from 2 to 6 carbon atoms, for 25 example the ethenyl, allyl, acetylenyl, propargyl, isoprenyl or hex-2-enyl group. Preferably, alkenyl groups have one or two (preferably one) double bond(s) and alkynyl groups have one or two (preferably one) triple bond(s). The term cycloalkyl refers to a cyclic group that has one or more rings (preferably 1 30 or 2) and contains especially from 3 to 14 ring carbon atoms, preferably from 3 to 10 ring carbon atoms. Examples are the cyclopropyl, cyclobutyl, cyclopentyl and cyclo hexyl group. The term aryl or Ar refers to an aromatic group that has one or more rings having 35 especially from 6 to 14 ring carbon atoms, preferably from 6 to 10 (especially 6) ring carbon atoms. Examples are the phenyl, naphthyl or biphenyl group.
WO 2007/012474 -6 - PCT/EP2006/007374 The terms arylalkyl, alkylaryl, arylalkenyl, alkenylaryl, arylalkynyl and alkynylaryl refer to groups which, in accordance with the above definitions, contain both aryl and alkyl, alkenyl or alkynyl groups. Specific examples are toluene, xylene, mesitylene, styrene, 5 benzyl and cumene. Such a group preferably contains one or two aromatic rings having from 6 to 10 ring carbon atoms and one or two alkyl, alkenyl and/or alkynyl groups having from 1 or 2 to 6 carbon atoms. Examples of non-crosslinkable organofunctional silanes are: bis-(dimethylamino) 10 methylphenylsilanes, bis-(mono-n-butylamino)dimethylsilanes, 2-chloroethyltrichloro silanes, 2-chloroethylmethyldichlorosilanes, di-n-butyldichlorosilanes, diethyldiethoxy silanes, ethyltrimethoxysilanes, 8-bromooctyltrichlorosilanes, 3-bromopropyltrichloro silanes, tert-butyltrichlorosilanes, 1-chloroethyltrichlorosilanes, chloromethyltrichloro silanes, chlorophenyltrichlorosilanes, cyclohexyltrichlorosilanes, dimethyldichloro 15 silanes, diphenyldichlorosilanes, ethyldichlorosilanes. Special preference is given to phenyltrimethoxysilane, aminopropyltriethoxysilane and propyltrimethoxysilane. Examples of crosslinkable organofunctional silanes are vinyltrimethoxysilane, amino propyltriethoxysilane, isocyanatopropyltriethoxysilane, mercaptopropyltrimethoxy 20 silane, vinyltriethoxysilanes, vinylethyldichlorosilanes, vinylmethyldiacetoxysilanes, vinylmethyldichlorosilanes, vinylmethyldiethoxysilanes, vinyltriacetoxysilanes, vinyl trichlorosilanes, phenylvinyldiethoxysilanes, phenylallyldichlorosilanes, 3-isocyanato poryltriethoxysilanes, 3-isocyanatopropyltriethoxysilanes, methacryloxypropenyltri rnethoxylsilanes, 3-methacryloxypropyltrimethoxysilanes. Special preference is given 25 to methacryloxypropyltrimethoxysilane and 3-glycidyloxypropyltrimethoxysilane. Examples of metal compounds are: TiC 4 , ZrCl 4 , Ti(OC 2
H
5
)
4 , Ti(OC 3
H
7
)
4 , Ti(O-iso
C
3
H
7
)
4 , Ti(OC 4
H
9
)
4 , Zr(O-iso-C 3
H
7 ), Zr(OC 4
H
9
)
4 , Ti(acetylacetonato) 2 (O-iso-C 3
H)
2 , Zr(acetylacetonato) 4 , Ti(2-ethylhexyloxy) 4 and other titanium or zirconium complexes 30 with chelate ligands which are preferably coordinated by way of oxygen and/or nitrogen; AI(OCH 3
)
3 , AI(OC 2
H
5
)
3 , AI(O-n-C 3
H
7
)
3 , AI(O-iso-C 3
H
7
)
3 , AI(OC 4
H
9
)
3 , AI(O-iso
C
4
H
9
)
3 , AI(O-sec-C 4
H
9
)
3 , AIC1 3 , AICI(OH) 2 , aluminium formate, aluminium acetate and aluminium oxalate as well as the corresponding (partially) chelated compounds, such as, for example, the acetylacetonates. Compounds that are liquid at room 35 temperature, such as, for example, AI(O-sec-C 4
H
9
)
3 and AI(O-iso-C 3
H
7
)
3 are preferred.
WO 2007/012474 -7 - PCT/EP2006/007374 Cycloolefin copolymer (COC) can be used as material for the plastics bottles. Cyclo olefin copolymers are copolymers of ethylene and cyclic olefins. Suitable monomers are unsubstituted or substituted ethylenes. The cyclic olefin monomers are derived 5 especially from dicyclopentadiene and can likewise be in unsubstituted or substituted form. The cycloolefin copolymers can be used in admixture with polypropylene, poly vinyl chloride or polyvinylidene chloride. It is preferable to use high-purity cycloolefin copolymers of substituted ethylene and substituted norbomene. They are available from Ticona under the trade name Topas@. They are distinguished by high break 10 resistance, high transparency and high heat, radiation and chemical resistance. They are free of ions and heavy metals. They can be sterilised by means of autoclaving, ethylene oxide and gamma or electron radiation. In addition, they have pronounced barrier properties with respect to water vapour and oxygen. For example, Topas 8007, 6013 and 6015 exhibit lower permeability to water vapour and oxygen than polypropyl 15 ene. ORMOCERs (Organic Modified Ceramics) are understood as being inorganic-organic hydrid polymers. They are silicone polymers which are known as coating material for metals, glass, stone, etc. The preparation of the inorganic-organic hybrid polymers is 20 described, for example, in DE 43 03 570 C. For the synthesis of the hybrid polymers there are used functionalised silanes RmSiX4.m, wherein X is a hydrolysable and condensable group and R is a cross linkable organic radical. The groups X can be, independently of one another, alkoxy 25 groups, aryloxy groups, acyloxy groups, alkylcarbonyl groups, alkoxycarbonyl groups, halogen, hydrogen or substituted or unsubstituted amino groups. The crosslinkable radical R can be alkyl, alkenyl, alkynyl, aryl, arylalkyl, alkylaryl, arylalkenyl, alkenylaryl, arylalkynyl, alkynylaryl, it being possible for those radicals to be interrupted by 0, S or N atoms or by NH groups, or to have terminal OH, SH or NH 2 groups, and to carry 30 one or more substituents from the group of the halogens and substituted or unsub stituted amino, amide, aldehyde, keto, alkylcarbonyl, carboxy, mercapto, cyano, isocyano, cyanato, isocyanato, hydroxy, alkoxy, alkoxycarbonyl, sulfonic acid, phos phoric acid, acrylic, acryloxy, methacrylic, methacryloxy, epoxy, glycidyl, glycidyloxy or vinyl groups. The number m can have the value 1, 2 or 3. The compounds RmSiX 4 -m 35 are combined with metal compounds such as halogen, alkyl, alkoxy, acyloxy or hydroxy compounds of aluminium, zirconium or titanium. The metal compounds can WO 2007/012474 - 8 - PCT/EP2006/007374 be oligomeric in chelate compound form. It may also be a complexed or non complexed aluminium salt with an organic or inorganic acid. In addition to comprising a hydrolytic condensate of RmSiX 4 -m with a metal compound, the coating material comprises a prepolymer. The prepolymers can react with the crosslinkable groups R 5 and thus serve the crosslinking. Preferably, the prepolymers can have reacting groups that are identical to the radical R of the compound RmSiX 4 -m. For example, in the case of acrylic-group-containing silanes, acrylates are used as prepolymer. The coating material can, in addition, contain non-crosslinkable organofunctional silanes, for example having alkyl or aryl groups, and/or low-volatility oxides. 10 The preparation and use of the inorganic-organic hybrid polymers is effected by the hydrolysis of the starting compounds to form a colloidal solution which contains the split-off hydrolysis products, for example the alcohols, and which is termed a lacquer. If applicable, it is also possible to add lacquer solvents. Such a lacquer can be applied 15 to the material to be coated. Once the Si-O-Si network has been formed, the cross linking of the organic molecule groups takes place. That can be effected by polymerisation or polyaddition reactions. As coating material there may be used ORMOCER lacquer ABRASIL GA2-30 or 20 GA2-35 and Ormocer lacquer ABRASIL VM-26-IPA2. ORMOCER lacquer ABRASIL GA2-30 is a thermally hardening hybrid lacquer having a high degree of scratch resistance, high moisture and chemical resistance, a high-gloss surface and high thermal resistance. ABRASIL GA2-35, a variant of ABRASIL GA2-30, is likewise a thermally hardening hydrid lacquer. ABRASIL GA2-35 is a preparation having 25 hydrolysed organically modified silicic acid esters, hydrolysed aluminium alkoxide and a complex-former. Also present are an epoxy resin and, as solvent, 2-butanol and methoxypropanol. ORMOCER lacquer ABRASIL VM-26-IPA2 is a UV-hardening hybrid lacquer having a high degree of scratch resistance. Preferably, ORMOCER lacquer ABRASIL GA2-30 and ABRASIL GA2-35 are used. 30 The plastics bottles according to the invention can be injection bottles (=vial), screw closure bottles or ampoules. The plastics bottles can have a cylindrical shape or have a rectangular base. Injection 35 bottles or screw-closure bottles can contain a volume of from 1 to 1000 ml. The WO 2007/012474 - 9 - PCT/EP2006/007374 volume of the injection bottles is preferably from 2 to 100 ml. Ampoules can contain a volume of from 1 to 20 ml. The plastics injection bottles can be closed with rubber stoppers. Suitable materials 5 for the rubber stoppers are chlorobutyl or bromobutyl rubber stoppers. The stopper can be provided with a crimped cap of a lightweight metal, for example of aluminium. The screw-closure bottles can be closed with a screw closure made, for example, of aluminium. 10 The coated plastics bottles can be produced by the following process: - coating of the COC bottles with an ORMOCER lacquer by means of vacuum vapour deposition, immersion, flood-coating, pouring, injection, spraying or brush 15 application, preferably by spraying - full hardening of the lacquer by UV or IR radiation or heat treatment at from 60 to 150 0 C, especially at 130 0 C The layer thickness of the ORMOCER lacquer can be from 1 to 100 pm, especially 20 from 2 to 30 pm. A layer thickness of from 8 to 20 pm is preferred. The coated COC bottles can be filled with a pharmaceutical preparation. The coated COC bottles can be autoclaved, radiation-sterilised or sterilised with 25 ethylene oxide. The sterilised COC bottles can be fed into the filling apparatus, the bottles being pressed tightly against one another by a holding ring to prevent them from falling over. The bottles are placed onto a conveyor belt with the aid of a turntable, the 30 bottles still being held tightly pressed together by means of a holding ring. The action of the turntable and the holding ring causes the bottles to rub against one another, which in the case of uncoated plastics bottles would result in their outer surfaces becoming scratched. The bottles are transported by conveyor belt to the filling needles, where they are filled with the liquid in question. The bottles are then closed 35 with a rubber stopper and crimped cap.
-10 The filled plastics bottles according to the invention can be autoclaved. Autoclaving can be carried out at a temperature of at least 1210C, at a pressure of at least 2 bar for a period of at least 15 min. Alternatively, autoclaving at 1 10*C and a longer period in the autoclave is possible, 5 The invention is explained in greater detail by the following Example, but without the scope of the invention being limited thereby. Example 1: 10 Substrate: vials made of Topas Lacquer: Abrasil GA2-30 Pretreatment: flame treatment on a mandrel before lacquering, wipe with acetone and blow off with compressed 15 air Application: spraying Full hardening: 130*C/1 hour The COC bottles are pretreated by flame treatment before lacquering. The lacquer 20 Abrasil GA2-30 is applied in a spraying process. The full hardening of the lacquer layer is effected in an oven at 130*C/1 hour. The film adheres well to the surface of the bottle. This is shown by a layer adhesion test by means of the cross-cut test (DIN ISO 2409). The coated bottles are washed in a bottle-washing machine and dried in a sterilisation 25 tunnel. The bottles are filled with an oxaliplatin solution in a filling/capping apparatus (for example VSR F01 from Bosch/Strunk) and then autoclaved at at least 121 C/2 bar/15 min. After passing through the filling apparatus, the bottles have no scratches. Comprises/comprising and grammatical variations thereof when used in this specification are to be taken to specify the presence of stated features, integers, steps or components or groups thereof, but do not preclude the presence or addition of one or more other features, integers, steps, components or groups thereof.
Claims (28)
1. Bottle made of plastics, comprising or consisting of cycloolefin copolymer, having a coating of an inorganic-organic hybrid polymer (ORMOCER coating). 5
2. Bottle according to claim 1, the cycloolefin copolymer being a copolymer of ethylene and cycloolefin.
3. Bottle according to claim 2, the ethylene being unsubstituted or substituted. 10
4. Bottle according to any one of the preceding claims, the cycloolefin being dicyclo pentadiene or a dicyclopentadiene derivative.
5. Bottle according to claim 4, the dicyclopentadiene or dicyclopentadiene derivative 15 being unsubstituted or substituted
6. Bottle according to any one of the preceding claims, the plastics comprising or consisting of a mixture of the cycloolefin polymer and a polymer from the group formed by polypropylene, polyvinyl chloride and polyvinylidene chloride. 20
7. Bottle according to any one of the preceding claims having a hybrid polymer coating, comprising or consisting of (i) a hydrolytic condensate, preparable from a silane of the formula RmSiX 4 m having the following meanings: 25 R = crosslinkable organic radical X = hydrolysable and condensable group m = 1 or 2 or 3 (with 1 being preferred) with a metal compound, (ii) a prepolymer that is crosslinkable with the radicals R of the silane, 30 (iii) one or more optional non-crosslinkable organofunctional silane(s) and (iv) an optional low-volatility oxide.
8. Bottle according to claim 7, R in the silane formula being a radical from the group formed by alkyl, alkenyl, alkynyl, aryl, arylalkyl, alkylaryl, arylalkenyl, alkenylaryl, 35 arylalkynyl and alkynylaryl and it being possible for those radicals to be inter- WO 2007/012474 - 12 - PCT/EP2006/007374 rupted one or more times by an 0 atom and/or an S atom and/or an N atom and/or by an NH group, or to have a terminal OH, SH or NH 2 group.
9. Bottle according to claim 8, the radicals R in the silane formula being, independ 5 ently of one another, an unsubstituted radical or a radical substituted by one or more substituents from the group formed by halogen atoms, unsubstituted amino, amide, aldehyde, keto, alkylcarbonyl, carboxy, mercapto, cyano, isocyano, cyanato, isocyanato, hydroxy, alkoxy, alkoxycarbonyl, sulfonic acid, phosphoric acid, acrylic, acryloxy, methacrylic, methacryloxy, glycidyl, glycidyloxy, epoxy and 10 vinyl groups and such groups in substituted form.
10. Bottle according to any one of claims 7 to 9, the radicals X in the silane formula being, independently of one another, alkoxy groups, aryloxy groups, acyloxy groups, alkylcarbonyl groups, alkoxycarbonyl groups, hydroxy groups, halogen, 15 hydrogen or substituted or unsubstituted amino groups.
11. Bottle according to any one of claims 7 to 10, comprising a prepolymer which carries a group R as reactive group, R having a meaning in accordance with any one of claims 7 to 9. 20
12. Bottle according to claim 11, comprising a prepolymer which carries a group R as reactive group, R in the prepolymer and in the silane having the same meaning.
13. Bottle according to any one of claims 7 to 12, the silane and the prepolymer 25 being a combination as follows: (i) silane having epoxy groups with epoxy resin as prepolymer and/or (ii) silane having vinyl radicals with prepolymer having crosslinkable double bonds and/or (iii) silane having polymerisable double bonds with prepolymer having cross 30 linkable double bonds and/or (iv) mercapto-group-containing silane with prepolymer having crosslinkable double bonds and/or (v) isocyanate-group-containing silane with polyol as prepolymer and/or (vi) hydroxyl-group-containing silane with isocyanate as prepolymer and/or 35 (vii) amino-group-containing silane with epoxy resin as prepolymer. WO 2007/012474 - 13 - PCT/EP2006/007374
14. Bottle according to any one of claims 7 to 13, comprising a hydrolytic condensate of an acrylic-group-containing silane and with a prepolymer acrylate. 5
15. Bottle according to any one of claims 7 to 14, comprising an optional non crosslinkable organofunctional silane of the formula R'mSiX4.m having the following meanings: R'= non-crosslinkable organic radical X = hydrolysable and condensable group 10 m=1or2or3.
16. Bottle according to claim 15, R' in the silane formula being a radical from the group formed by alkyl, cycloalkyl, aryl, arylalkyl and alkylaryl and it being possible for those radicals to be interrupted one or more times by an 0 atom and/or an S 15 atom and/or an N atom and/or by an NH group or to have a terminal OH, SH or NH 2 group.
17. Bottle according to claim 15 or 16, the radicals R' in the silane formula being, independently of one another, an unsubstituted radical or a radical substituted by 20 one or more substituents from the group formed by halogen atoms, unsubstituted amide, aldehyde, keto, alkylcarbonyl, carboxy, cyano, alkoxy, alkoxycarbonyl groups and such groups in substituted form.
18. Bottle according to any one of claims 15 to 17, the radicals X in the silane formula 25 being, independently of one another, alkoxy groups, aryloxy groups, alkylcarbonyl groups, alkoxycarbonyl groups, hydroxy groups, halogen, hydrogen or substituted or unsubstituted amino groups.
19. Bottle according to any one of claims 7 to 18, comprising a low-volatility oxide of 30 compounds of elements of main group la, Ila, lila, IVa and/or Va or of sub-group Ilb, Illb, Vb, VIb, Vllb and/or VIlIb, with the exception of aluminium.
20. Bottle according to claim 19, comprising B 2 0 3 , P 2 0 5 and/or SnO 2 . 35
21. Bottle according to any one of the preceding claims, comprising ABRASIL GA2-30, ABRASIL GA2-35 or ABRASIL VM-26-IPA2 as coating material. WO 2007/012474 - 14 - PCT/EP2006/007374
22. Bottle according to any one of the preceding claims, having a cylindrical or prismatic or square shape. 5
23. Bottle according to any one of the preceding claims, the bottle being an injection bottle, a screw-closure bottle or an ampoule.
24. Bottle according, to claim 22 or 23 in the form of an injection bottle or screw closure bottle having a volume of from 1 to 1000 ml. 10
25. Bottle according to claim 24 in the form of an injection bottle having a volume of from 2 to 100 ml.
26. Bottle according to claim 22 or 23 in the form of an ampoule having a volume of 15 from 1 to 20 ml.
27. Bottle according to any one of the preceding claims, having a coating having a thickness of from 1 to 100 pm, especially from 2 to 30 pm and preferably from 8 to 20 pm. 20
28. Bottle according to any one of the preceding claims, filled with a pharmaceutical preparation and closed with a closure.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005034892A DE102005034892A1 (en) | 2005-07-26 | 2005-07-26 | Cycloolefin copolymer bottle with a scratch-resistant coating |
| DE102005034892.0 | 2005-07-26 | ||
| PCT/EP2006/007374 WO2007012474A1 (en) | 2005-07-26 | 2006-07-26 | Cycloolefin copolymer bottle with a scratch-resistant coating |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2006274207A1 AU2006274207A1 (en) | 2007-02-01 |
| AU2006274207B2 true AU2006274207B2 (en) | 2011-07-21 |
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ID=37012498
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006274207A Ceased AU2006274207B2 (en) | 2005-07-26 | 2006-07-26 | Cycloolefin copolymer bottle with a scratch-resistant coating |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20080217202A1 (en) |
| EP (1) | EP1907460B1 (en) |
| JP (1) | JP2009503164A (en) |
| CN (1) | CN101228218A (en) |
| AT (1) | ATE450560T1 (en) |
| AU (1) | AU2006274207B2 (en) |
| CA (1) | CA2614791A1 (en) |
| DE (2) | DE102005034892A1 (en) |
| ES (1) | ES2335921T3 (en) |
| NO (1) | NO20080221L (en) |
| PL (1) | PL1907460T3 (en) |
| SI (1) | SI1907460T1 (en) |
| WO (1) | WO2007012474A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102020210680A1 (en) | 2020-08-21 | 2022-02-24 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Adhesion Promoting Composite, Method of Making an Adhesion Promoting Composite, Electrical Device, Method of Making an Electrical Device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2010061910A1 (en) * | 2008-11-28 | 2012-04-26 | 東洋製罐株式会社 | High gloss multi-layer plastic container |
| WO2011120595A1 (en) * | 2010-03-29 | 2011-10-06 | Siemens Concentrated Solar Power Ltd. | Front surface mirror for reflecting sunlight, method for manufacturing the mirror and use of the mirror |
| WO2016138455A1 (en) * | 2015-02-26 | 2016-09-01 | Sio2 Medical Products, Inc. | Cycloolefin polymer container with a scratch resistant and anti-static coating |
| CN107709423A (en) * | 2015-07-01 | 2018-02-16 | 沙特基础工业全球技术有限公司 | The frosting of hardness with enhancing and the method for manufacturing it |
| CN107876356A (en) * | 2017-11-28 | 2018-04-06 | 安徽益顺塑业有限公司 | A kind of coating process of transparent plastic bottle |
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- 2005-07-26 DE DE102005034892A patent/DE102005034892A1/en not_active Withdrawn
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2006
- 2006-07-26 US US11/996,771 patent/US20080217202A1/en not_active Abandoned
- 2006-07-26 AU AU2006274207A patent/AU2006274207B2/en not_active Ceased
- 2006-07-26 AT AT06762821T patent/ATE450560T1/en active
- 2006-07-26 WO PCT/EP2006/007374 patent/WO2007012474A1/en active Application Filing
- 2006-07-26 CN CNA2006800268894A patent/CN101228218A/en active Pending
- 2006-07-26 CA CA002614791A patent/CA2614791A1/en not_active Abandoned
- 2006-07-26 ES ES06762821T patent/ES2335921T3/en active Active
- 2006-07-26 SI SI200630541T patent/SI1907460T1/en unknown
- 2006-07-26 JP JP2008523234A patent/JP2009503164A/en active Pending
- 2006-07-26 PL PL06762821T patent/PL1907460T3/en unknown
- 2006-07-26 EP EP06762821A patent/EP1907460B1/en not_active Not-in-force
- 2006-07-26 DE DE502006005525T patent/DE502006005525D1/en active Active
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- 2008-01-14 NO NO20080221A patent/NO20080221L/en not_active Application Discontinuation
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1479379A1 (en) * | 2003-05-19 | 2004-11-24 | Euro-Celtique S.A. | Dry liposomal PVP-iodine compositions |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102020210680A1 (en) | 2020-08-21 | 2022-02-24 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Adhesion Promoting Composite, Method of Making an Adhesion Promoting Composite, Electrical Device, Method of Making an Electrical Device |
| WO2022038271A1 (en) | 2020-08-21 | 2022-02-24 | Robert Bosch Gmbh | Coupling agent composite material, method for producing a coupling agent composite material, electrical device, and method for producing an electrical device |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080217202A1 (en) | 2008-09-11 |
| AU2006274207A1 (en) | 2007-02-01 |
| CA2614791A1 (en) | 2007-02-01 |
| DE502006005525D1 (en) | 2010-01-14 |
| EP1907460B1 (en) | 2009-12-02 |
| JP2009503164A (en) | 2009-01-29 |
| NO20080221L (en) | 2008-02-22 |
| EP1907460A1 (en) | 2008-04-09 |
| ATE450560T1 (en) | 2009-12-15 |
| WO2007012474A1 (en) | 2007-02-01 |
| CN101228218A (en) | 2008-07-23 |
| PL1907460T3 (en) | 2010-04-30 |
| DE102005034892A1 (en) | 2007-02-08 |
| SI1907460T1 (en) | 2010-03-31 |
| ES2335921T3 (en) | 2010-04-06 |
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