HK1066527A1 - Processes for the purification of higher diamondoiss and compositions comprising such diamondoids - Google Patents

Processes for the purification of higher diamondoiss and compositions comprising such diamondoids

Info

Publication number
HK1066527A1
HK1066527A1 HK04109481A HK04109481A HK1066527A1 HK 1066527 A1 HK1066527 A1 HK 1066527A1 HK 04109481 A HK04109481 A HK 04109481A HK 04109481 A HK04109481 A HK 04109481A HK 1066527 A1 HK1066527 A1 HK 1066527A1
Authority
HK
Hong Kong
Prior art keywords
diamondoiss
diamondoids
purification
compositions
processes
Prior art date
Application number
HK04109481A
Other languages
English (en)
Inventor
Jeremy E Dahl
Robert M Carlson
Original Assignee
Chevron Usa Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Chevron Usa Inc filed Critical Chevron Usa Inc
Publication of HK1066527A1 publication Critical patent/HK1066527A1/xx

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • C07C13/64—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings with a bridged ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/395—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification of at least one compound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/05—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
    • C07C23/18—Polycyclic halogenated hydrocarbons
    • C07C23/20—Polycyclic halogenated hydrocarbons with condensed rings none of which is aromatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
    • C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/28—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings
    • C07C47/34—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic
    • C07C47/347—Saturated compounds having —CHO groups bound to carbon atoms of rings other than six—membered aromatic rings polycyclic having a —CHO group on a condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
    • C07C49/423—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/04—Purification; Separation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/135—Purification; Separation; Use of additives by gas-chromatography
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/90—Ring systems containing bridged rings containing more than four rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nanotechnology (AREA)
  • Water Supply & Treatment (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Mathematical Physics (AREA)
  • Theoretical Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Composite Materials (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Carbon And Carbon Compounds (AREA)
  • Processing Of Solid Wastes (AREA)
  • Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
  • Manufacture And Refinement Of Metals (AREA)
  • Chemical Vapour Deposition (AREA)
HK04109481A 2001-01-19 2004-12-01 Processes for the purification of higher diamondoiss and compositions comprising such diamondoids HK1066527A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US26284201P 2001-01-19 2001-01-19
PCT/US2002/004549 WO2002096804A2 (en) 2001-01-19 2002-01-17 Processes for the purification of higher diamondoids and compositions comprising such diamondoids

Publications (1)

Publication Number Publication Date
HK1066527A1 true HK1066527A1 (en) 2005-03-24

Family

ID=22999293

Family Applications (1)

Application Number Title Priority Date Filing Date
HK04109481A HK1066527A1 (en) 2001-01-19 2004-12-01 Processes for the purification of higher diamondoiss and compositions comprising such diamondoids

Country Status (24)

Country Link
US (2) US6844477B2 (xx)
EP (1) EP1392603B1 (xx)
JP (1) JP2005503352A (xx)
KR (1) KR20040004490A (xx)
CN (1) CN1286784C (xx)
AR (2) AR032499A1 (xx)
AT (1) ATE438590T1 (xx)
AU (1) AU2002321993B2 (xx)
BR (1) BR0206531A (xx)
CA (1) CA2435407A1 (xx)
CZ (1) CZ20031977A3 (xx)
DE (1) DE60233221D1 (xx)
HK (1) HK1066527A1 (xx)
HU (1) HUP0302721A3 (xx)
IL (2) IL156963A0 (xx)
MX (1) MXPA03006377A (xx)
MY (1) MY143730A (xx)
NO (1) NO20033259L (xx)
NZ (1) NZ525260A (xx)
PL (1) PL369175A1 (xx)
RU (1) RU2307822C2 (xx)
TW (2) TWI302527B (xx)
WO (3) WO2002096804A2 (xx)
ZA (5) ZA200302929B (xx)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7795468B2 (en) * 2001-01-19 2010-09-14 Chevron U.S.A. Inc. Functionalized higher diamondoids
IL156965A0 (en) * 2001-01-19 2004-02-08 Chevron Usa Inc Polymerizable higher diamondoid derivatives
US6843851B2 (en) * 2001-01-19 2005-01-18 Chevron U.S.A., Inc. Compositions comprising pentamantanes and processes for their separation
US7173160B2 (en) * 2002-07-18 2007-02-06 Chevron U.S.A. Inc. Processes for concentrating higher diamondoids
US7309476B2 (en) * 2002-07-18 2007-12-18 Chevron U.S.A. Inc. Diamondoid-based components in nanoscale construction
US7049374B2 (en) 2002-07-18 2006-05-23 Chevron U.S.A. Inc. Heterodiamondoids
US7488565B2 (en) * 2003-10-01 2009-02-10 Chevron U.S.A. Inc. Photoresist compositions comprising diamondoid derivatives
US7402716B2 (en) * 2003-12-31 2008-07-22 Chevron U.S.A. Inc. Hybrid cubic/hexagonal diamondoids
US20070037909A1 (en) * 2005-08-10 2007-02-15 Chevron U.S.A. Inc. Diamondoid-based nucleating agents for thermoplastics
US20070251446A1 (en) * 2006-03-24 2007-11-01 Chevron U.S.A. Inc. Chemically attached diamondoids for CVD diamond film nucleation
US8062512B2 (en) * 2006-10-06 2011-11-22 Vary Petrochem, Llc Processes for bitumen separation
US7758746B2 (en) 2006-10-06 2010-07-20 Vary Petrochem, Llc Separating compositions and methods of use
CA2665579C (en) 2006-10-06 2015-06-30 Robert C. Yeggy Separating compositions and methods of use
US8367166B2 (en) * 2008-10-31 2013-02-05 Chevron U.S.A. Inc. Synthesis of higher diamondoids
CN102101817B (zh) * 2009-12-18 2013-04-24 中国石油天然气股份有限公司 石油和烃源岩中低级金刚烷类化合物的分离和富集方法
JPWO2011099351A1 (ja) * 2010-02-12 2013-06-13 国立大学法人 東京大学 ダイヤモンドイドの合成方法及びダイヤモンドイド
WO2012096710A2 (en) * 2011-01-14 2012-07-19 Exxonmobil Upstream Research Company System and method for performing geochronology
CN102768256B (zh) * 2012-07-23 2014-06-04 中国石油天然气股份有限公司 用全二维气相色谱定量石油样品中金刚烷类化合物的方法
WO2019060467A1 (en) 2017-09-21 2019-03-28 Verily Life Sciences Llc RETINAL CAMERAS WITH MOBILE OPTICAL STOPS
CN111635289B (zh) * 2020-04-29 2022-07-05 中国石油天然气股份有限公司 一种分离原油中乙基降金刚烷类化合物的方法和系统

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US3457318A (en) 1967-11-30 1969-07-22 Atlantic Richfield Co Alkenyl adamantanes
US3832332A (en) 1971-10-22 1974-08-27 Sun Research Development Polyamide polymer of diamino methyl adamantane and dicarboxylic acid
US4982049A (en) 1989-05-26 1991-01-01 Mobil Oil Corp. Purification of hydrocarbonaceous fractions
CA2017527A1 (en) 1989-05-26 1990-11-26 Mobil Oil Corporation Purification of hydrocarbonaceous fractions
US4952748A (en) 1989-05-26 1990-08-28 Mobil Oil Corp. Purification of hydrocarbonaceous fractions
US4952749A (en) 1989-05-26 1990-08-28 Mobil Oil Corp. Removal of diamondoid compounds from hydrocarbonaceous fractions
US4952757A (en) 1989-11-15 1990-08-28 Summagraphics Corporation Low-power electromagnetic digitizer tablet
US5017734A (en) 1989-12-11 1991-05-21 Kurt Baum Ethynyl adamantane derivatives and methods of polymerization thereof
US5019665A (en) 1990-04-18 1991-05-28 Mobil Oil Corp. Shape-selective process for concentrating diamondoid-containing hydrocarbon solvents
US5245104A (en) 1990-12-17 1993-09-14 Mobil Oil Corporation Method and apparatus for producing and separating diamondoid compounds from natural gas streams
US5461184A (en) 1991-09-25 1995-10-24 Chevron U.S.A. Inc. Method for diamondoid extraction using a solvent system
US5414189A (en) 1992-08-24 1995-05-09 Mobil Oil Corporation Isolation of high purity diamondoid fractions and components
US5268513A (en) 1992-09-10 1993-12-07 Mobil Oil Corporation Air hydroxylation of diamondoids
US5256391A (en) 1992-09-11 1993-10-26 Mobil Oil Corporation Method for synthesizing microporous crystalline material
US5298666A (en) 1992-09-18 1994-03-29 Mobil Oil Corporation Synthesis of adamantane-2,4-dione
US5306851A (en) * 1992-11-23 1994-04-26 Mobil Oil Corporation High viscosity index lubricant fluid
US5347063A (en) 1993-03-09 1994-09-13 Mobil Oil Corporation Method for direct arylation of diamondoids
US5576355A (en) 1993-06-04 1996-11-19 Mobil Oil Corp. Diamondoid derivatives for pharmaceutical use
US5369213A (en) 1993-06-30 1994-11-29 Mobil Oil Corporation Oxidative coupling of diamondoids and aromatics
US5382684A (en) 1993-07-06 1995-01-17 Mobil Oil Corporation Nitrogenous 1,3-substituted adamantanes
US5334228A (en) * 1993-10-18 1994-08-02 Mobil Oil Corporation Deposit control additives and fuel compositions containing the same
US5400427A (en) 1993-10-18 1995-03-21 Mobil Oil Corporation Fiber optic cable and viscous filler material
US5397488A (en) 1993-12-09 1995-03-14 Mobil Oil Corporation Oxidatively stable esters derived from diamondoids totally hydroxylated at the bridgeheads
US5430193A (en) 1994-04-22 1995-07-04 Mobil Oil Corporation Synthesis of 4-hydroxy-2-adamantanes and related compounds
US5394733A (en) 1994-06-24 1995-03-07 Mobil Oil Corporation Quantitative pyrolysis-gas chromatography using diamondoid compounds
US5498812A (en) 1994-08-04 1996-03-12 Mobil Oil Corporation Two-stage process for producing diamondoid hydrocarbons
KR20000029498A (ko) 1997-05-23 2000-05-25 고지마 아끼로;오가와 다이스께 중합성아다만탄유도체및그의제조방법

Also Published As

Publication number Publication date
TWI235743B (en) 2005-07-11
EP1392603B1 (en) 2009-08-05
CZ20031977A3 (cs) 2003-12-17
CN1286784C (zh) 2006-11-29
ZA200302928B (en) 2004-04-14
PL369175A1 (en) 2005-04-18
US6743290B2 (en) 2004-06-01
MXPA03006377A (es) 2004-10-29
US20020139295A1 (en) 2002-10-03
NO20033259D0 (no) 2003-07-18
WO2002096804A2 (en) 2002-12-05
WO2002057202A1 (en) 2002-07-25
CN1501900A (zh) 2004-06-02
TWI302527B (en) 2008-11-01
BR0206531A (pt) 2004-03-23
ATE438590T1 (de) 2009-08-15
WO2002057203A1 (en) 2002-07-25
ZA200302925B (en) 2004-07-19
US20020193648A1 (en) 2002-12-19
IL156963A0 (en) 2004-02-08
MY143730A (en) 2011-06-30
JP2005503352A (ja) 2005-02-03
RU2307822C2 (ru) 2007-10-10
ZA200302927B (en) 2004-05-27
EP1392603A2 (en) 2004-03-03
KR20040004490A (ko) 2004-01-13
HUP0302721A2 (hu) 2003-11-28
NZ525260A (en) 2004-09-24
ZA200302929B (en) 2004-04-14
NO20033259L (no) 2003-09-12
DE60233221D1 (de) 2009-09-17
RU2003125362A (ru) 2005-02-10
AR032499A1 (es) 2003-11-12
HUP0302721A3 (en) 2005-05-30
CA2435407A1 (en) 2002-12-05
IL156963A (en) 2006-08-20
AU2002321993B2 (en) 2007-04-05
ZA200302926B (en) 2004-04-14
WO2002096804A3 (en) 2003-12-18
US6844477B2 (en) 2005-01-18
AR035529A1 (es) 2004-06-02

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PC Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee)

Effective date: 20110117