ZA200603260B - Radical interceptors as stabilizers of polymerizable compounds - Google Patents
Radical interceptors as stabilizers of polymerizable compounds Download PDFInfo
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- ZA200603260B ZA200603260B ZA200603260A ZA200603260A ZA200603260B ZA 200603260 B ZA200603260 B ZA 200603260B ZA 200603260 A ZA200603260 A ZA 200603260A ZA 200603260 A ZA200603260 A ZA 200603260A ZA 200603260 B ZA200603260 B ZA 200603260B
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- ZA
- South Africa
- Prior art keywords
- process according
- alkyl
- cyo
- compounds
- carbon atoms
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 19
- 239000003381 stabilizer Substances 0.000 title claims description 8
- -1 p- hydroxyphenyl Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 22
- 239000002516 radical scavenger Substances 0.000 claims description 16
- 229940123457 Free radical scavenger Drugs 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 238000003860 storage Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 6
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 2
- 229910052684 Cerium Inorganic materials 0.000 claims 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229920001567 vinyl ester resin Polymers 0.000 claims 2
- OHANAHYVFPTLJI-UHFFFAOYSA-N (carbamoylamino)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCNC(N)=O OHANAHYVFPTLJI-UHFFFAOYSA-N 0.000 claims 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 101100459438 Caenorhabditis elegans nac-1 gene Proteins 0.000 claims 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 239000008139 complexing agent Substances 0.000 claims 1
- BNKAXGCRDYRABM-UHFFFAOYSA-N ethenyl dihydrogen phosphate Chemical class OP(O)(=O)OC=C BNKAXGCRDYRABM-UHFFFAOYSA-N 0.000 claims 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 claims 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 229950000688 phenothiazine Drugs 0.000 claims 1
- 150000004986 phenylenediamines Chemical class 0.000 claims 1
- 150000004053 quinones Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 7
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 7
- 229960003330 pentetic acid Drugs 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000006641 stabilisation Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 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 2
- URDCARMUOSMFFI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(2-hydroxyethyl)amino]acetic acid Chemical compound OCCN(CC(O)=O)CCN(CC(O)=O)CC(O)=O URDCARMUOSMFFI-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- 125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006060 1,1-dimethyl-3-butenyl group Chemical group 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000006061 1,2-dimethyl-1-butenyl group Chemical group 0.000 description 1
- 125000006034 1,2-dimethyl-1-propenyl group Chemical group 0.000 description 1
- 125000006062 1,2-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000006035 1,2-dimethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006063 1,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- 125000006064 1,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
- 125000006065 1,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006036 1-ethyl-1-propenyl group Chemical group 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006044 1-methyl-1-pentenyl group Chemical group 0.000 description 1
- 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006048 1-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000006052 1-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- FCKYPQBAHLOOJQ-UWVGGRQHSA-N 2-[[(1s,2s)-2-[bis(carboxymethyl)amino]cyclohexyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)[C@H]1CCCC[C@@H]1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UWVGGRQHSA-N 0.000 description 1
- HZZOUWBMMWVPTR-UHFFFAOYSA-N 2-[[6-[bis(carboxymethyl)amino]-1,4-dioxocan-6-yl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)C1(N(CC(O)=O)CC(O)=O)CCOCCOC1 HZZOUWBMMWVPTR-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000006026 2-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006045 2-methyl-1-pentenyl group Chemical group 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006049 2-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006056 2-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- SEEZWGFVHCMHJF-UHFFFAOYSA-N 2-nitrosophenol Chemical compound OC1=CC=CC=C1N=O SEEZWGFVHCMHJF-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006046 3-methyl-1-pentenyl group Chemical group 0.000 description 1
- 125000006050 3-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006054 3-methyl-3-pentenyl group Chemical group 0.000 description 1
- 125000006057 3-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- 125000006047 4-methyl-1-pentenyl group Chemical group 0.000 description 1
- 125000006051 4-methyl-2-pentenyl group Chemical group 0.000 description 1
- 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006058 4-methyl-4-pentenyl group Chemical group 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- FCKYPQBAHLOOJQ-UHFFFAOYSA-N Cyclohexane-1,2-diaminetetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)C1CCCCC1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940048195 n-(hydroxyethyl)ethylenediaminetriacetic acid Drugs 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 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
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
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Description
PF 54925 ® Radical interceptors as stabilizers of polymerizable compounds
The present invention describes the use of free radical scavengers for stabilizing polymerizable compounds to polymerization.
It is known that polymerizable compounds can readily be caused to polymerize, for example by heat or the action of light or peroxides. Since, however, polymerization has to be diminished or reduced for safety and economic reasons during production, working-up, storage and/or transport, there is a constant demand for novel, effective polymerization inhibitors.
Particularly problematic are the chemical and/or physical processing during the working-up, for example by distillation or rectification, and subsequently the storage and the transport.
A large number of stabilizers for polymerizable compounds are known, in particular for acrylic acid and methacrylic acid, referred to below as (meth)acrylic acid, and the esters thereof, referred to below as (meth)acrylates.
GB-A 1 601 979 describes the stabilization of an aqueous solution of a (meth)acrylate salt with a nitrosophenolate in the presence of EDTA as a chelator.
US 4,929,660 discloses an adhesive composition which comprises a free radical acrylic monomer and a polymerization inhibitor, a metal chelator and a free radical scavenger.
This free radical scavenger is an N,N-dialkyl- or N,N-diarylalkylhydroxylamine.
The stabilization of unsaturated quaternary ammonium salts in the presence of metal scavengers is described in US 5,912,383. These metal scavengers may be diethylenetriaminepentaacetic acid and N-(hydroxyethyl)ethylenediaminetriacetic acid and the associated sodium salts.
DE-A 199 20 796 describes a process for the preparation of isobornyl (meth)acrylates by reacting camphene with (meth)acrylic acid, which process is likewise carried out in the presence of a chelate former. Nitrilotriacetic acid, ethylenediaminetetraacetic acid,
N-(2-hydroxyethyl)ethylenediaminetriacetic acid, 1,2-cyclohexylenedinitrilotetraacetic acid, diethylenetriaminepentaacetic acid, 3,6-dioxaoctamethylenedinitrilotetraacetic acid and the alkali metal salts of these acids are disclosed as chelate formers in this publication. 40 WO 02/26685 describes the stabilization of acrylic monomers during the distillation with a stabilizer in the presence of oxygen with a metal scavenger which is selected from ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTPA)
JE
* PF 54925 2 and the sodium salt thereof (NasDTPA) and trans-1,2-cyclohexanediaminepentaacetic acid. These metal scavengers are used for complexing free iron.
JP 05-295011 and JP 05-320205 likewise describe the stabilization of acrylic acid in the presence of EDTA, DTPA, CYDTA and the alkali metal salts thereof.
H-is-an-object-of the-present-invention A need exists to provide an alternative process for stabilizing polymerizable compounds to polymerization during working-up, storage and/or transport.
We have found that this objest need is achieved fulfilled by a process for stabilizing polymerizable compounds to polymerization during working-up, storage and/or transport, where at least one free radical scavenger which contains at least two glycine units is used, with the proviso that the free radical scavenger is not selected from ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTPA), trans-1,2-cyclohexanediaminetetraacetic acid (CYDTA) and the alkali metal and alkaline earth metal salts thereof. in a preferred embodiment, at least one free radical scavenger which contains at least two glycine units is used, with the proviso that the free radical scavenger does not have 2 2 of the following structural units:
RO OR'
YN
Oo + Oo where R and R’, independently of one another, may be hydrogen or metal. For example, these metals may be alkali metals, such as sodium or potassium.
In a particularly preferred embodiment, at least one free radical scavenger which contains at least two glycine units and at least one amide and/or ester unit is used. The free radical scavenger preferably has two amide units.
Very particularly preferably used free radical scavengers are those of the formula (1): 1 2
R R
~ 0 0”
A A
N X N ®
Gc" So 0” 6?
AMENDED SHEET
) PF 54925 3 ® Specifically:
G' may be NR’R* or OR” and G? may be NR®R® or OR®.
X may be C;-Cy-alkyl, NCH,COOR®, NR, O, S, PR", Se, SIORR" or aryl, where said substituents may be substituted in any desired position, but not more than five times, preferably not more than four times, particularly preferably not more than three times, by one or more hetero atoms and/or halogen atoms. X is preferably a C;-Cy- alkyl group or NCHCOOR?®, particularly preferably X is a C,-Cy-alkyl group or
NCHCOOR®. k, I, m and n, independently of one another, are from 0 to 20. | and m are preferably in the range from 0 to 10, particularly preferably from O to 5, very particularly preferably from 0 to 3 and particularly preferably from 0 to 2. k and n preferably have the same value, e.g. in the range from 0 to 10, preferably from 0 to 5, very particularly preferably from 1 to 3; in particular k and n have the value 1.
Specifically, the radicals R' to R® may have the following meaning:
R'to R® independently of one another, may be hydrogen, C1-Cyo-alkyl, C4-Cyo- alkylcarbonyl, C,-Cx-alkenyl, C,-Cop-alkenylcarbonyl, C,-Cyg-alkynyl, Co-Coo- alkynylcarbonyl, C;-C,s-cycloalkyl, Cs-C,s-cycloalkylcarbonyl, aryl, arylcarbonyl or heterocycles,
R’ and R?®, independently of one another, may be C,-Cyo-alkyl, C4-Cyo-alkylcarbonyl, C,-
Cyo-alkenyl, C,-Cyp-alkenylcarbonyl, C,-Cye-alkynyl, C,-Cxe-alkynylcarbonyl, C3-Cys- cycloalkyl, Cs-C,s-cycloalkylcarbonyl, aryl, arylcarbonyl or heterocycles, where a) in the case of said aliphatic substituents, the radicals R*® and R* or R® and R® may also be linked to one another and together may thus form a three-membered to eight-membered, preferably a five-membered to seven-membered and particularly preferably a five-membered or six-membered ring, b) said aliphatic substituents may be straight-chain or branched, ¢) the substituents may each be interrupted in any desired position by one or more hetero atoms, the number of these hetero atoms being not more than 10, preferably 40 not more than 8, particularly preferably not more than § and in particular not more than 3, and/or :
’ PF 54925 4 ® d) the substituents may each be substituted in any desired position, but not more than five times, preferably not more than four times and particularly preferably not more than three times, by alkyl, alkyloxy, alkyloxycarbonyl, aryl, aryloxy, aryloxycarbonyl, hydroxycarbonyl, aminocarbonyl, heterocycles, hetero atoms or halogen atoms, it being possible for these likewise to be substituted not more than twice, preferably not more than once, by said groups.
R® to R'®, if appropriate independently of one another, are hydrogen or C;-Cy-alkyl.
Specifically, the general terms stated for the various radicals R have the following meaning:
C,-Coo-Alkyl: straight-chain or branched hydrocarbon radicals of up to 20 carbon atoms, preferably C,-C4o-alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert- butyl, 1,1-dimethylethyl, pentyl, 2-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyt, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 2-methylpentyl, 3-methylpentyl, 1,1- dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1- methylpropyl, 1-ethyl-2-methylpropyl, heptyl, octyl, 2-ethylhexyl, 2,4,4-trimethylpentyl, 1,1,3,3-tetramethylbutyl, nonyl and decyl and the isomers thereof.
C,-C,o-Alkylcarbonyl: a straight-chain or branched alkyl group of 1 to 20 carbon atoms (as stated above) which are attached via a carbonyl group (-CO-), preferably C,.C;o- alkylcarbonyl, for example formyl, acetyl, n-propionyl or isopropionyl, n-butanoyl, isobutanoyl, sec-butanoyl or tert-butanoyl, n-pentanoyl, isopentanoyl, sec-pentanoyl or tert-pentanoyl, n-nonanoy! or isononanoyl or n-decanoyl.
C,-C,o-Alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 20 carbon atoms and a double bond in any desired position, preferably C,-Cq- alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyi-2-propenyl, 2-methyl-2- propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl- 1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, 1-methyi-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2- propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyi- 2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1- pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2- pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3- pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4- 40 pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl- 2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2- dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-
Claims (21)
1. A process for stabilizing polymerizable compounds to polymerization during working-up, storage and/or transport, wherein at least one free radical scavenger which comprises at least two glycine units and at least one amide and/or ester unit is used.
2. The process according to claim 1, wherein at least one free radical scavenger of the formula (I) R _R? >So 0 oP Ao Ny pXyq oN 0) 2 £7 Go oxdich where G' may be NR*R* or OR’, G? may be NR°R® or OR?, R' to R®, independently of one another, may be hydrogen, C;-Co-alkyl, C4-Coo- alkylcarbonyl, C,-Cyg-alkenyl, C,-Cyo-alkenylcarbonyl, C,-Cye-alkynyl,
C.-Cyp-alkynylcarbonyl, C;-Cqs-cycloalkyl, Cs-Cs-cycloalkylcarbonyl, aryl, arylcarbonyl or heterocycles, R” and R®, independently of one another, may be C;-Cyp-alkyl, C1-Coo- alkylcarbonyl, C,-Cyo-alkenyl, C,-Cyo-alkenylcarbonyl, C,-Cyo-alkynyl, C,-Cyo-alkynylcarbonyl, C;-C4s-cycloalkyl, Cs-Cys-cycloalkylcarbonyl, aryl, arylcarbonyl or heterocycles, X may be C,-Cxo-alkyl, NCH,COOR®, NR", O, S, PR", Se, SiOR"’R" 40 or aryl, where R® to R'®, independently of one another, may be hydrogen or C,-Cy-alkyl, and k, I, m and n, independently of one another, may be numbers from 0 to 20, 45 is used.
’ PF 54925 ® 35
3. The process according to claim 2, wherein R' and R? are identical and are hydrogen or C,-Cy-alkyl.
4. The process according to claim 2 or 3, wherein R® and R® are identical and are hydrogen, C-Cyo-alkyl oderor C,-Cye-alkylcarbonyl.
5. The process according to any of claims 2 to 4, wherein R* and R® are identical and are C,-Cye-alkyl, C,-Cye-alkylcarbonyl, aryl, C,-Cyo-alkenyl, C,-Co- : alkenylcarbonyl, C,-Cye-alkynyl or C,-Cy-alkynylcarbonyl.
6. The process according to either of claims 4 and 5, wherein R*and R® are hydrogen and R* and R® are selected from phenyl, benzyl, p-methoxyphenyl, o-, m- or p- hydroxyphenyl, 1-hydroxyhexyl, methyl, ethyl, propyl, butyl, ethylene glycol, diethylene glycol, triethylene glycol, ethoxylate having 4 to 10 EO units, ethylenediamine, diethylenetriamine, triethylenetetramine and amino acids.
7. The process according to any of claims 2 to 6, wherein R” and R® are identical and are C,-Cyo-alkyl, C1-Cyo-alkylcarbonyl, aryl, C,-Cye-alkenyl, C,-Coo- alkenylcarbonyl, C,-Cye-alkynyl or C,-Cys-alkynylcarbonyl.
8. The process according to claim 7, wherein R” and R® are selected from phenyl, benzyl, p-methoxyphenyl, o-, m- or p-hydroxyphenyl, 1-hydroxyhexyl, methyl, ethyl, propyl, butyl, ethylene glycol, diethylene glycol, ethoxylate having 4 to 10 EO units, ethylenediamine, diethylenetriamine, triethylenetetramine and amino acids.
9. The process according to any of claims 2 to 8, wherein X is C4-Cy-alkyl or CH,NCOOR?®.
10. The process according to any of claims 1 to 9, wherein at least one of the following compounds is used: oH y ORL oA AN ~NY Yeu, oJ © LI °y oy 0 hid Dh OH OH ° Ng HC £,
, PF 54925 OH on HC ag Ao Aho 0 Ak o So NNN Td rte
0. 0, oO Ny oy oy 0 OH OH OH OH [e] { ;
HO. N Rk OH HC hE © we 0] © - 0 Ho Bh ¢ o ) NE ag N N “3 o oy) Shi 0 rel eH, OH HO ° r OY }§ No o © - 0 Ne MeSH HO SN NN oY “4 OH he oA) : BY A N Oo N o Nad 1 TG 07 “oH 4 0) OH OH OH a SUSI eo JY RU NAN ° AN OH OH OH OH
11. The process according to any of claims 1 to 10, wherein from 0.1 to 1 000 ppm, based on the polymerizable compound, of the free radical scavenger or of a free radical scavenger mixture are used.
, PF 54925 ® 37
12. The process according to any of claims 1 to 11, wherein at least one costabilizer is used.
13. The process according to claim 12, wherein the costabilizer is selected from the group consisting of the oxygen-containing gases, phenolic compounds, quinones and hydroquinones, N-oxyl compounds, aromatic amines, phenylenediamines, imines, sulfonamides, oximes, hydroxylamines, urea derivatives, phosphorus- containing compounds, sulfur-containing compounds, complexing agents based on tetraazaannulenes and metal salts, and, if appropriate, mixtures thereof.
14. The process according to claim 12 or 13, wherein phenothiazine, hydroquinone, hydroquinone monomethyl ether, 2,2,6,6-tetramethylpiperidin-N-oxyl, 4-hydroxy- 2,2,6,6-tetramethylpiperidin-N-oxy!, 4-ox0-2,2,6,6-tetramethyipiperidin-N-oxyl, N,N’-di-sec-butyl-p-phenylenediamine, cerium(lll) acetate, cerium(lll) ethylhexanoate, oxygen-containing gases and/or mixtures thereof are used as the costabilizer.
15. The process according to any of the preceding claims, wherein the polymerizable compound comprises at least one ethylenically unsaturated group.
16. The process according to claim 15, wherein the polymerizable compound is selected from the group consisting of the mono-, di- or triethylenically unsaturated C;-Cg-carboxylic acids, C4-Cyp-esters, C,-C,p-amides, C;-Coo-nitriles and C,-Cyp-anhydrides of these mono-, di- or triethylenically unsaturated C,-Cg- carboxylic acids, vinyl esters of carboxylic acids comprising up to 20 carbon atoms, vinyl ethers of alcohols comprising from 1 to 10 carbon atoms, vinylaromatics and vinyliheteroaromatics of up to 20 carbon atoms, vinyllactams having 3 to 10 carbon atoms in the ring, open-chain N-vinylamide compounds and N-vinylamine compounds, vinyl halides, aliphatic, if appropriate halogenated, hydrocarbons having 2 to 8 carbon atoms and 1 or 2 double bonds, vinylidenes or mixtures of these monomers.
17. The process according to claim 15 or 16, wherein mono-, di- or triethylenically unsaturated C;-Cs-carboxylic acids, C;-C,p-esters of these mono-, di- or triethylenically unsaturated C;-Cg-carboxylic acids, vinyl esters of carboxylic acids comprising up to 20 carbon atoms, vinyl ethers of alcohols comprising 1 to 10 carbon atoms, vinylaromatics and vinylheteroaromatics of up to 20 carbon atoms, vinyllactams having 3 to 10 carbon atoms in the ring, open-chain N- 40 vinylamide compounds or N-vinylamine compounds are used as the polymerizable compound.
, PF 54925 ® 38
18. The process according to any of claims 15 to 17, wherein (meth)acrylic acid, (meth)acrylates, N-vinylcaprolactam, N-vinylformamide, N-vinylimidazole, N- vinylpyrrolidone, vinylphosphoric acids, N-vinylcarbazole, N,N- divinylethyleneurea, trimethylolpropane triacrylate, ureidomethyl methacrylate, styrene, butadiene or isoprene is used as the polymerizable compound.
19. A stabilizer mixture comprising i) atleast one free radical scavenger which comprises at least two glycine units and at least one amide and/or ester unit, and ii) atleast one further stabilizer or costabilizer. 156
20. A mixture comprising a stabilizer mixture according to claim 19 and at least one polymerizable compound.
21. The use of a stabilizer mixture according to claim 19 for stabilizing polymerizable compounds to polymerization during working-up, storage and/or transport.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03021803A EP1518916A1 (en) | 2003-09-26 | 2003-09-26 | Scavenger of free radicals as stabilizers of polymerisable compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200603260B true ZA200603260B (en) | 2007-07-25 |
Family
ID=34178505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200603260A ZA200603260B (en) | 2003-09-26 | 2006-04-24 | Radical interceptors as stabilizers of polymerizable compounds |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1518916A1 (en) |
| CN (1) | CN1878852A (en) |
| ZA (1) | ZA200603260B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1874728B1 (en) * | 2005-04-28 | 2014-03-19 | Nippon Shokubai Co.,Ltd. | Composition of n-alkenyl carboxylic acid tertiary amide |
| GB201317423D0 (en) * | 2013-10-02 | 2014-09-17 | Pb Clermont Sa | Stabilized nitrocellulose based propellant composition |
| CN117431054B (en) * | 2023-11-01 | 2024-04-16 | 滨州乾坤化工机械有限公司 | High-temperature iron ion stabilizer for acidizing fracturing fluid and preparation method thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH569405A5 (en) * | 1972-07-11 | 1975-11-28 | Ciba Geigy Ag | Combatting metal deficiency in biological systems - with metal chelates of ethylene diamine tetraacetic acid diamide derivs |
| FR2639640B1 (en) * | 1988-11-25 | 1992-07-24 | Rhone Poulenc Chimie | METHOD FOR DELAYING THE GELIFICATION OF UNSATURATED MONOMERS, DELAYED GELLING COMPOSITIONS CONTAINING SAID MONOMERS AND APPLICATION OF SAID COMPOSITIONS TO THE TREATMENT OF UNDERGROUND FORMATIONS |
| DE19920796A1 (en) * | 1999-05-06 | 2000-11-09 | Roehm Gmbh | Production of isobornyl (meth)acrylate, used in lacquer binder production, uses aqueous sulfuric acid and inhibitor in reaction of camphene with (meth)acrylic acid |
| DE10105014C2 (en) * | 2001-01-26 | 2003-03-27 | Schering Ag | New process for the production of DTPA monoamides |
-
2003
- 2003-09-26 EP EP03021803A patent/EP1518916A1/en not_active Withdrawn
-
2004
- 2004-09-18 CN CNA2004800330735A patent/CN1878852A/en active Pending
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2006
- 2006-04-24 ZA ZA200603260A patent/ZA200603260B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1518916A1 (en) | 2005-03-30 |
| CN1878852A (en) | 2006-12-13 |
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