CA1009096A - Carbon-coated articles and method of making same - Google Patents

Carbon-coated articles and method of making same

Info

Publication number
CA1009096A
CA1009096A CA185,117A CA185117A CA1009096A CA 1009096 A CA1009096 A CA 1009096A CA 185117 A CA185117 A CA 185117A CA 1009096 A CA1009096 A CA 1009096A
Authority
CA
Canada
Prior art keywords
carbon
making same
coated articles
articles
coated
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.)
Expired
Application number
CA185,117A
Other languages
English (en)
Other versions
CA185117S (en
Inventor
Jack C. Bokros
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gulf Oil Corp
Original Assignee
Gulf Oil Corp
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 Gulf Oil Corp filed Critical Gulf Oil Corp
Application granted granted Critical
Publication of CA1009096A publication Critical patent/CA1009096A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23CCOATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/22Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
    • C23C16/26Deposition of carbon only
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61FFILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2/00Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
    • A61F2/02Prostheses implantable into the body
    • A61F2/24Heart valves ; Vascular valves, e.g. venous valves; Heart implants, e.g. passive devices for improving the function of the native valve or the heart muscle; Transmyocardial revascularisation [TMR] devices; Valves implantable in the body
    • A61F2/2421Heart valves ; Vascular valves, e.g. venous valves; Heart implants, e.g. passive devices for improving the function of the native valve or the heart muscle; Transmyocardial revascularisation [TMR] devices; Valves implantable in the body with non-pivoting rigid closure members
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/02Inorganic materials
    • A61L27/08Carbon ; Graphite
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28Materials for coating prostheses
    • A61L27/30Inorganic materials
    • A61L27/306Other specific inorganic materials not covered by A61L27/303 - A61L27/32
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00Use of inorganic substances as compounding ingredients
    • C08K3/02Elements
    • C08K3/04Carbon
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00Use of inorganic substances as compounding ingredients
    • C08K3/10Metal compounds
    • C08K3/14Carbides
    • CCHEMISTRY; METALLURGY
    • C23COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23CCOATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C16/00Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
    • C23C16/22Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
    • FMECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16JPISTONS; CYLINDERS; SEALINGS
    • F16J15/00Sealings
    • F16J15/16Sealings between relatively-moving surfaces
    • F16J15/34Sealings between relatively-moving surfaces with slip-ring pressed against a more or less radial face on one member
    • F16J15/3496Sealings between relatively-moving surfaces with slip-ring pressed against a more or less radial face on one member use of special materials
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61FFILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F2310/00Prostheses classified in A61F2/28 or A61F2/30 - A61F2/44 being constructed from or coated with a particular material
    • A61F2310/00005The prosthesis being constructed from a particular material
    • A61F2310/00161Carbon; Graphite
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/26Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/263Coating layer not in excess of 5 mils thick or equivalent
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/26Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/263Coating layer not in excess of 5 mils thick or equivalent
    • Y10T428/264Up to 3 mils
    • Y10T428/2651 mil or less
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2918Rod, strand, filament or fiber including free carbon or carbide or therewith [not as steel]
    • Y10T428/292In coating or impregnation
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/30Self-sustaining carbon mass or layer with impregnant or other layer
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31678Of metal

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Public Health (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Metallurgy (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • General Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Cardiology (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Vapour Deposition (AREA)
  • Laminated Bodies (AREA)
  • Carbon And Carbon Compounds (AREA)
  • Materials For Medical Uses (AREA)
  • Physical Vapour Deposition (AREA)
CA185,117A 1973-02-05 1973-11-06 Carbon-coated articles and method of making same Expired CA1009096A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US05/329,526 US3969130A (en) 1973-02-05 1973-02-05 Carbon-coated articles and method of making same

Publications (1)

Publication Number Publication Date
CA1009096A true CA1009096A (en) 1977-04-26

Family

ID=23285822

Family Applications (1)

Application Number Title Priority Date Filing Date
CA185,117A Expired CA1009096A (en) 1973-02-05 1973-11-06 Carbon-coated articles and method of making same

Country Status (10)

Country Link
US (1) US3969130A (ja)
JP (1) JPS49111912A (ja)
CA (1) CA1009096A (ja)
CH (1) CH592746A5 (ja)
DE (1) DE2360686A1 (ja)
ES (1) ES421423A1 (ja)
FR (1) FR2216366B1 (ja)
GB (1) GB1420483A (ja)
IT (1) IT997807B (ja)
SE (1) SE400268B (ja)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1490347A (en) * 1974-02-08 1977-11-02 Dunlop Ltd Friction members
US4038703A (en) * 1975-11-14 1977-08-02 General Atomic Company Prosthetic devices having a region of controlled porosity
US4035541A (en) * 1975-11-17 1977-07-12 Kennametal Inc. Sintered cemented carbide body coated with three layers
DE2603456C2 (de) * 1976-01-30 1984-04-05 Robert Bosch Gmbh, 7000 Stuttgart Verfahren zur Herstellung eines Knochenimplantates
US4405685A (en) * 1980-11-13 1983-09-20 Agency Of Industrial Science & Technology, Ministry Of International Trade & Industry Carbon fibers with duplex metal carbide coating and methods for manufacture thereof
US4537759A (en) * 1981-08-24 1985-08-27 Eagle-Picher Industries, Inc. Production of elemental silicon from impure silane feed
US4487799A (en) * 1982-06-24 1984-12-11 United Technologies Corporation Pyrolytic graphite pretreatment for carbon-carbon composites
US4850717A (en) * 1982-09-17 1989-07-25 Clark Eugene V Process sensor tube having erosion and corrosion resistance
US5387247A (en) * 1983-10-25 1995-02-07 Sorin Biomedia S.P.A. Prosthetic device having a biocompatible carbon film thereon and a method of and apparatus for forming such device
US4668579A (en) * 1984-02-01 1987-05-26 The United States Of America As Represented By The Secretary Of The Air Force Interstitially protected oxidation resistant carbon-carbon composite
JPS60227763A (ja) * 1984-04-27 1985-11-13 筏 義人 抗血栓性医用材料
FR2566272B1 (fr) * 1984-06-20 1987-04-03 France Implant Est Implants chirurgicaux perfectionnes comportant un revetement, notamment en nitrure de titane
DE3687529T2 (de) * 1985-03-20 1993-05-13 Sharp Kk Herstellung von graphiteinlagerungsverbindung und gedopte carbonfilme.
US5084151A (en) * 1985-11-26 1992-01-28 Sorin Biomedica S.P.A. Method and apparatus for forming prosthetic device having a biocompatible carbon film thereon
IT1196836B (it) * 1986-12-12 1988-11-25 Sorin Biomedica Spa Protesi in materiale polimerico con rivestimento di carbonio biocompatibile
JPH01197376A (ja) * 1988-02-01 1989-08-09 Ibiden Co Ltd 多孔質炭素材及びその製造方法
JPH0722018B2 (ja) * 1988-03-04 1995-03-08 シャープ株式会社 黒鉛電極の製造方法
US5169508A (en) * 1988-03-04 1992-12-08 Sharp Kabushiki Kaisha Graphite electrode
DE8815082U1 (de) * 1988-11-29 1989-05-18 Biotronik Meß- und Therapiegeräte GmbH & Co Ingenieurbüro Berlin, 1000 Berlin Herzklappenprothese
US5163958A (en) * 1989-02-02 1992-11-17 Cordis Corporation Carbon coated tubular endoprosthesis
US4980202A (en) * 1989-07-03 1990-12-25 United Technologies Corporation CVD SiC matrix composites containing carbon coated fibers
US5370694A (en) * 1989-07-25 1994-12-06 Smith & Nephew Richards, Inc. Zirconium oxide and nitride coated endoprostheses for tissue protection
US5258022A (en) * 1989-07-25 1993-11-02 Smith & Nephew Richards, Inc. Zirconium oxide and nitride coated cardiovascular implants
US5628790A (en) * 1989-07-25 1997-05-13 Smith & Nephew, Inc. Zirconium oxide zirconium nitride coated valvular annuloplasty rings
US5282850A (en) * 1989-07-25 1994-02-01 Smith & Nephew Richards, Inc. Artificial heart components with wear resistant coatings of reduced thrombogenicity
US5496359A (en) * 1989-07-25 1996-03-05 Smith & Nephew Richards, Inc. Zirconium oxide and zirconium nitride coated biocompatible leads
US5611347A (en) * 1989-07-25 1997-03-18 Smith & Nephew, Inc. Zirconium oxide and zirconium nitride coated percutaneous devices
US5477864A (en) * 1989-12-21 1995-12-26 Smith & Nephew Richards, Inc. Cardiovascular guidewire of enhanced biocompatibility
JPH046265A (ja) * 1990-04-24 1992-01-10 Toyota Central Res & Dev Lab Inc 鉄系合金基体への固体潤滑被膜の形成方法および固体潤滑被膜をもつ摺動部材
IT1247037B (it) * 1991-06-25 1994-12-12 Sante Camilli Valvola venosa artificiale
US5238866A (en) * 1991-09-11 1993-08-24 GmbH & Co. Ingenieurburo Berlin Biotronik Mess- und Therapiegerate Plasma enhanced chemical vapor deposition process for producing an amorphous semiconductive surface coating
US5207707A (en) * 1992-01-16 1993-05-04 Carbomedics, Inc. Tri-leaflet all carbon heart valve
US5514410A (en) * 1994-09-08 1996-05-07 Carbon Implants, Inc. Pyrocarbon and process for depositing pyrocarbon coatings
US5954724A (en) 1997-03-27 1999-09-21 Davidson; James A. Titanium molybdenum hafnium alloys for medical implants and devices
EP1200639A1 (en) 1999-05-20 2002-05-02 Medicalcv, Inc. Pyrolytic carbon coating apparatus having feed gas actuator
US7632309B1 (en) * 1999-12-13 2009-12-15 St. Jude Medical, Inc. Pyrolytic carbon and metal/metalloid carbide composites
DE602005008057D1 (de) 2004-03-01 2008-08-21 Pebble Bed Modular Reactor Pty Kernbrennstoff
US20070228664A1 (en) * 2006-03-31 2007-10-04 Krishnamurthy Anand Mechanical seals and methods of making
EP2056004A1 (en) * 2007-10-29 2009-05-06 General Electric Company Mechanical seals and methods of making
JP2012517284A (ja) * 2009-02-09 2012-08-02 セント ジュード メディカル インコーポレイテッド 医療デバイスの生体適合性の向上
CN104984400B (zh) * 2015-07-10 2017-10-27 中奥汇成科技股份有限公司 一种具有碳基膜的关节头

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3676179A (en) * 1968-10-03 1972-07-11 Gulf Oil Corp Coated article and method for making same
US3673051A (en) * 1969-03-20 1972-06-27 Gen Electric Pyrolytic graphite
US3677795A (en) * 1969-05-01 1972-07-18 Gulf Oil Corp Method of making a prosthetic device
US3684585A (en) * 1970-07-13 1972-08-15 Materials Technology Corp Method for forming adherent titanium carbide coatings on metal or composite substrates
US3685059A (en) * 1970-07-28 1972-08-22 Gulf General Atomic Inc Prosthetic blood circulation device having a pyrolytic carbon coated blood contacting surface

Also Published As

Publication number Publication date
FR2216366B1 (ja) 1977-06-10
GB1420483A (en) 1976-01-07
FR2216366A1 (ja) 1974-08-30
SE400268B (sv) 1978-03-20
DE2360686A1 (de) 1974-08-08
US3969130A (en) 1976-07-13
IT997807B (it) 1975-12-30
JPS49111912A (ja) 1974-10-24
ES421423A1 (es) 1976-04-16
CH592746A5 (ja) 1977-11-15

Similar Documents

Publication Publication Date Title
CA1009096A (en) Carbon-coated articles and method of making same
AU474405B2 (en) Rapamycin and process of preparation
CA1016334A (en) Utility pole and method of making same
CA1006572A (en) Electrocatalyst and process of manufacture
CA991379A (en) Form of ammonium tetramolybdate and method of preparation
CA1023502A (en) Glove and method for the production of said glove
CA1025455A (en) N-phenylpyrroies and process for their manufacture
CA994697A (en) Type disc and method of making same
CA998294A (en) Flocked article and method of making
CA1030530A (en) Antibiotic derivatives of xk-62-2 and method of production thereof
AU471624B2 (en) Full open end and method of making
AU487735B2 (en) Article carrier and method of making same
CA961351A (en) Pallet and method of production
CA975976A (en) Thawer-cooker and method of using the same
CA1019355A (en) Limestone-expanding clay granules and method of making same
CA988072A (en) Catalyst and method of making same
AU476870B2 (en) Food container and method of making same
AU6854474A (en) Article carrier and method of making same
CA1006199A (en) Flange and method of making same
AU485751B2 (en) Multilayer composition and method of making same and articles therefrom
CA889947A (en) Product and method of making same
AU478202B2 (en) Disteroidyl-ethers and process
CA1002941A (en) Disteroidyl-ethers and process
AU481190B2 (en) Disteroidyl-ethers and process
CA1015354A (en) Disteroidyl-ethers and process