ZA200306007B - Peroxyester preparation method - Google Patents
Peroxyester preparation method Download PDFInfo
- Publication number
- ZA200306007B ZA200306007B ZA2003/06007A ZA200306007A ZA200306007B ZA 200306007 B ZA200306007 B ZA 200306007B ZA 2003/06007 A ZA2003/06007 A ZA 2003/06007A ZA 200306007 A ZA200306007 A ZA 200306007A ZA 200306007 B ZA200306007 B ZA 200306007B
- Authority
- ZA
- South Africa
- Prior art keywords
- process according
- carbon atoms
- hydroxy
- brevets
- alkyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 11
- -1 dimethylpropyl Chemical group 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 30
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 150000004820 halides Chemical class 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000008065 acid anhydrides Chemical class 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- WOFMVUZGDHWHLJ-UHFFFAOYSA-N 7,7-dimethyloctanoyl chloride Chemical group CC(C)(C)CCCCCC(Cl)=O WOFMVUZGDHWHLJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- OIXFWERBTHZQQH-UHFFFAOYSA-N 4-hydroperoxy-4-methylpentan-2-ol Chemical group CC(O)CC(C)(C)OO OIXFWERBTHZQQH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000003074 decanoyl 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(*)=O 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical group C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001867 hydroperoxy group Chemical group [*]OO[H] 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims description 2
- 125000000400 lauroyl group Chemical group O=C([*])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])C([H])([H])[H] 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- UIERETOOQGIECD-UHFFFAOYSA-N 2-methylbut-2-enoic acid Chemical class CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 claims 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims 1
- 125000001402 nonanoyl group Chemical group O=C([*])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 claims 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims 1
- 125000000297 undecanoyl group Chemical group O=C([*])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])[H] 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- 238000003756 stirring Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002609 medium Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000002432 hydroperoxides Chemical class 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- UYMQGIDIEUCSBT-UHFFFAOYSA-N hexane-1,6-diol hydrogen peroxide Chemical class OO.OCCCCCCO UYMQGIDIEUCSBT-UHFFFAOYSA-N 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- MVELOSYXCOVILT-UHFFFAOYSA-N (4-hydroxy-2-methylpentan-2-yl) 7,7-dimethyloctaneperoxoate Chemical compound CC(O)CC(C)(C)OOC(=O)CCCCCC(C)(C)C MVELOSYXCOVILT-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- QPEAPJAKKWYRRE-UHFFFAOYSA-N 3-hydroperoxy-3,5,5-trimethylcyclohexan-1-ol Chemical class CC1(C)CC(O)CC(C)(OO)C1 QPEAPJAKKWYRRE-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical class OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/38—Peroxy compounds the —O—O— group being bound between a >C=O group and a carbon atom, not further substituted by oxygen atoms, i.e. esters of peroxy acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0101921A FR2820740B1 (fr) | 2001-02-13 | 2001-02-13 | Procede de preparation d'un peroxyester |
| PCT/FR2002/000475 WO2002064555A1 (fr) | 2001-02-13 | 2002-02-07 | Procede de preparation d'un peroxyester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200306007B true ZA200306007B (en) | 2005-01-26 |
Family
ID=8859940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA2003/06007A ZA200306007B (en) | 2001-02-13 | 2003-08-04 | Peroxyester preparation method |
Country Status (16)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102532351B (zh) * | 2011-12-26 | 2013-12-18 | 淄博正华助剂股份有限公司 | 乳液型质量分数为50%过氧化新癸酸异丙苯酯的制法 |
| CN102584665B (zh) * | 2011-12-26 | 2014-12-24 | 淄博正华助剂股份有限公司 | 溶剂型质量分数75%过氧化新癸酸异丙苯酯的制法 |
| CN102585047A (zh) * | 2011-12-26 | 2012-07-18 | 淄博正华助剂股份有限公司 | 溶剂型质量分数75%过氧化二-（3，5，5-三甲基己酰）的制法 |
| CN102532352B (zh) * | 2011-12-26 | 2013-12-18 | 淄博正华助剂股份有限公司 | 乳液型质量分数50%过氧化二-（3，5，5-三甲基己酰）的制法 |
| JP6481336B2 (ja) * | 2014-11-10 | 2019-03-13 | 日油株式会社 | 乳化重合用単量体組成物 |
| CN104447471A (zh) * | 2014-11-26 | 2015-03-25 | 淄博正华助剂股份有限公司 | 连续流制备过氧化二-(3,5,5-三甲基己酰)的方法 |
| CN105693584A (zh) * | 2016-03-17 | 2016-06-22 | 乌鲁木齐市华泰隆化学助剂有限公司 | 过氧化新癸酸异丙苯酯及通过相转移催化剂制备过氧化新癸酸异丙苯酯的方法 |
| IL279349B2 (en) * | 2018-06-12 | 2025-09-01 | Nouryon Chemicals Int Bv | Process for manufacturing composite items |
| CN109400514A (zh) * | 2018-10-30 | 2019-03-01 | 乌鲁木齐市华泰隆化学助剂有限公司 | 一种过氧化（3,5,5－三甲基己酸）叔丁酯的制备方法 |
| CN109678773A (zh) * | 2018-12-13 | 2019-04-26 | 乌鲁木齐市华泰隆化学助剂有限公司 | 一种过氧化-2-乙基己酸叔丁酯的制备方法 |
| CN111363069B (zh) * | 2020-03-27 | 2022-04-19 | 乌鲁木齐市华泰隆化学助剂有限公司 | 一种聚氯乙烯树脂复合引发剂的制备方法 |
| CN114292219A (zh) * | 2021-12-24 | 2022-04-08 | 兰州助剂厂有限责任公司 | 一种1,1-二甲基-3-羟基丁基过氧化氢的制备方法 |
| CN115536565B (zh) * | 2022-09-23 | 2024-04-05 | 山东阳谷华泰化工股份有限公司 | 一种过氧化苯甲酸叔丁酯的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE627014A (cg-RX-API-DMAC10.html) * | 1962-01-12 | |||
| DE1225643B (de) * | 1964-03-17 | 1966-09-29 | Dr Christoph Ruechardt | Verfahren zur Herstellung neuer organischer Peroxycarbonsaeureester |
| NL135610C (cg-RX-API-DMAC10.html) * | 1966-11-09 | |||
| US4634753A (en) | 1983-05-20 | 1987-01-06 | Pennwalt Corporation | Hydroxy-t-alkyl peroxyester |
| US4525308A (en) * | 1983-05-20 | 1985-06-25 | Pennwalt Corporation | Hydroxy-t-alkyl peroxyesters |
| JPS6051169A (ja) * | 1983-08-30 | 1985-03-22 | Nippon Oil & Fats Co Ltd | ペルオキシエステルの製造方法 |
| KR20020043627A (ko) * | 1999-10-13 | 2002-06-10 | 샬크비즈크 피이터 코르넬리스; 페트귄터 | 혼합된 무수물을 사용하여 퍼옥시드를 제조하는 방법 |
-
2001
- 2001-02-13 FR FR0101921A patent/FR2820740B1/fr not_active Expired - Lifetime
-
2002
- 2002-02-07 BR BRPI0207193-2A patent/BR0207193B1/pt not_active IP Right Cessation
- 2002-02-07 HU HU0400769A patent/HUP0400769A3/hu unknown
- 2002-02-07 AU AU2002237361A patent/AU2002237361B2/en not_active Ceased
- 2002-02-07 CN CNB028048725A patent/CN1223583C/zh not_active Expired - Lifetime
- 2002-02-07 US US10/467,782 patent/US7439384B2/en not_active Expired - Fee Related
- 2002-02-07 AT AT02703673T patent/ATE304529T1/de not_active IP Right Cessation
- 2002-02-07 EP EP02703673A patent/EP1362029B1/fr not_active Revoked
- 2002-02-07 ES ES02703673T patent/ES2249553T3/es not_active Expired - Lifetime
- 2002-02-07 WO PCT/FR2002/000475 patent/WO2002064555A1/fr not_active Ceased
- 2002-02-07 DE DE60206136T patent/DE60206136T2/de not_active Expired - Lifetime
- 2002-02-07 JP JP2002564488A patent/JP4080885B2/ja not_active Expired - Lifetime
- 2002-02-07 KR KR1020037010571A patent/KR100717089B1/ko not_active Expired - Fee Related
- 2002-02-08 TW TW091102380A patent/TWI262183B/zh not_active IP Right Cessation
- 2002-04-28 SA SA2230079A patent/SA02230079B1/ar unknown
-
2003
- 2003-08-04 ZA ZA2003/06007A patent/ZA200306007B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20030075187A (ko) | 2003-09-22 |
| JP2004529098A (ja) | 2004-09-24 |
| HUP0400769A3 (en) | 2005-03-29 |
| BR0207193B1 (pt) | 2012-09-04 |
| SA02230079B1 (ar) | 2006-11-11 |
| ES2249553T3 (es) | 2006-04-01 |
| US20040176632A1 (en) | 2004-09-09 |
| ATE304529T1 (de) | 2005-09-15 |
| HUP0400769A2 (hu) | 2004-07-28 |
| EP1362029A1 (fr) | 2003-11-19 |
| TWI262183B (en) | 2006-09-21 |
| FR2820740B1 (fr) | 2003-04-25 |
| US7439384B2 (en) | 2008-10-21 |
| AU2002237361B2 (en) | 2006-05-04 |
| WO2002064555A1 (fr) | 2002-08-22 |
| JP4080885B2 (ja) | 2008-04-23 |
| CN1491210A (zh) | 2004-04-21 |
| KR100717089B1 (ko) | 2007-05-10 |
| EP1362029B1 (fr) | 2005-09-14 |
| CN1223583C (zh) | 2005-10-19 |
| DE60206136T2 (de) | 2006-06-22 |
| BR0207193A (pt) | 2004-02-10 |
| FR2820740A1 (fr) | 2002-08-16 |
| DE60206136D1 (de) | 2005-10-20 |
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