GB1470649A - Sulphurised norbornyl derivatives and their use as lubri cant additives - Google Patents

Sulphurised norbornyl derivatives and their use as lubri cant additives

Info

Publication number
GB1470649A
GB1470649A GB1772873A GB1772873A GB1470649A GB 1470649 A GB1470649 A GB 1470649A GB 1772873 A GB1772873 A GB 1772873A GB 1772873 A GB1772873 A GB 1772873A GB 1470649 A GB1470649 A GB 1470649A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
group containing
hydrogen atom
compound
alkyl group
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
GB1772873A
Other languages
English (en)
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.)
COOPER Ltd ETHYL
Original Assignee
COOPER Ltd ETHYL
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
Priority to NL159136D priority Critical patent/NL159136C/xx
Application filed by COOPER Ltd ETHYL filed Critical COOPER Ltd ETHYL
Priority to GB1772873A priority patent/GB1470649A/en
Priority to AR253275A priority patent/AR208174A1/es
Priority to AU67752/74A priority patent/AU491635B2/en
Priority to BR2912/74A priority patent/BR7402912D0/pt
Priority to JP4160874A priority patent/JPS5347124B2/ja
Priority to FR7412738A priority patent/FR2225431B1/fr
Priority to AT304674A priority patent/AT341537B/de
Priority to US459938A priority patent/US3882031A/en
Priority to BE143102A priority patent/BE813603A/xx
Priority to IT21301/74A priority patent/IT1007869B/it
Priority to DE2417864A priority patent/DE2417864C3/de
Priority to ZA00742357A priority patent/ZA742357B/xx
Priority to CA197,455A priority patent/CA1047476A/en
Priority to NL7405010.A priority patent/NL159136B/xx
Priority to US05/664,547 priority patent/US4097474A/en
Priority to JP281377A priority patent/JPS52107009A/ja
Publication of GB1470649A publication Critical patent/GB1470649A/en
Priority to SE7711154A priority patent/SE7711154L/xx
Priority to CA313,946A priority patent/CA1066270A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/02Sulfurised compounds
    • C10M135/04Hydrocarbons
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M135/00Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
    • C10M135/32Heterocyclic sulfur, selenium or tellurium compounds
    • C10M135/34Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/086Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/221Six-membered rings containing nitrogen and carbon only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/225Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
    • C10M2215/226Morpholines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/28Amides; Imides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/30Heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/02Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
    • C10M2219/022Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106Thiadiazoles
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/042Metal salts thereof
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/02Bearings
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00Specific manufacturing methods for lubricant compositions
    • C10N2070/02Concentrating of additives

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
GB1772873A 1973-04-12 1973-04-12 Sulphurised norbornyl derivatives and their use as lubri cant additives Expired GB1470649A (en)

Priority Applications (19)

Application Number Priority Date Filing Date Title
NL159136D NL159136C (enrdf_load_stackoverflow) 1973-04-12
GB1772873A GB1470649A (en) 1973-04-12 1973-04-12 Sulphurised norbornyl derivatives and their use as lubri cant additives
AR253275A AR208174A1 (es) 1973-04-12 1974-01-01 Procedimiento para preparar una substancia oleosoluble cartente de metal y de fosforo que se presta para ser usada como aditivo para lubricantes y composicion lubricante que la contiene
AU67752/74A AU491635B2 (en) 1973-04-12 1974-04-10 Lubricating compositions containing sulphurised norbornenyl derivatives
BR2912/74A BR7402912D0 (pt) 1973-04-12 1974-04-10 Processo para preparar uma substancia isenta de fosforo, soluvel em oleo, isenta de metal, adequada para uso como aditivo de lubrificante; composicao lubrificante, e solucao de aditivo de lubrificante
JP4160874A JPS5347124B2 (enrdf_load_stackoverflow) 1973-04-12 1974-04-10
BE143102A BE813603A (fr) 1973-04-12 1974-04-11 Additifs de lubrifiants
CA197,455A CA1047476A (en) 1973-04-12 1974-04-11 Lubricant additives
US459938A US3882031A (en) 1973-04-12 1974-04-11 Lubricant compositions
FR7412738A FR2225431B1 (enrdf_load_stackoverflow) 1973-04-12 1974-04-11
IT21301/74A IT1007869B (it) 1973-04-12 1974-04-11 Additivi per lubrificanti
DE2417864A DE2417864C3 (de) 1973-04-12 1974-04-11 Schmiermittel
ZA00742357A ZA742357B (en) 1973-04-12 1974-04-11 Lubricant additives
AT304674A AT341537B (de) 1973-04-12 1974-04-11 Verfahren zur herstellung eines schmiermittelzusatzes
NL7405010.A NL159136B (nl) 1973-04-12 1974-04-11 Werkwijze ter bereiding van smeeroliesamenstellingen.
US05/664,547 US4097474A (en) 1973-04-12 1976-03-08 Process for sulfurizing norbornenyl compounds
JP281377A JPS52107009A (en) 1973-04-12 1977-01-12 Method of making additive for lubricating oil
SE7711154A SE7711154L (sv) 1973-04-12 1977-10-05 Sett att framstella en smorjmedeltillsats
CA313,946A CA1066270A (en) 1973-04-12 1978-10-23 Lubricant additives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1772873A GB1470649A (en) 1973-04-12 1973-04-12 Sulphurised norbornyl derivatives and their use as lubri cant additives

Publications (1)

Publication Number Publication Date
GB1470649A true GB1470649A (en) 1977-04-14

Family

ID=10100199

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1772873A Expired GB1470649A (en) 1973-04-12 1973-04-12 Sulphurised norbornyl derivatives and their use as lubri cant additives

Country Status (14)

Country Link
US (1) US3882031A (enrdf_load_stackoverflow)
JP (2) JPS5347124B2 (enrdf_load_stackoverflow)
AR (1) AR208174A1 (enrdf_load_stackoverflow)
AT (1) AT341537B (enrdf_load_stackoverflow)
BE (1) BE813603A (enrdf_load_stackoverflow)
BR (1) BR7402912D0 (enrdf_load_stackoverflow)
CA (1) CA1047476A (enrdf_load_stackoverflow)
DE (1) DE2417864C3 (enrdf_load_stackoverflow)
FR (1) FR2225431B1 (enrdf_load_stackoverflow)
GB (1) GB1470649A (enrdf_load_stackoverflow)
IT (1) IT1007869B (enrdf_load_stackoverflow)
NL (2) NL159136B (enrdf_load_stackoverflow)
SE (1) SE7711154L (enrdf_load_stackoverflow)
ZA (1) ZA742357B (enrdf_load_stackoverflow)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1518102A (en) * 1974-07-25 1978-07-19 Cooper Ltd Ethyl Trithiolan derivatives and lubricating compositions containing them
GB1560667A (en) * 1976-09-24 1980-02-06 Cooper & Co Ltd Edwin Sulphurize olefins and their use as lubricant additives
US4389221A (en) * 1982-07-23 1983-06-21 Shell Oil Company Gasoline composition and method for reducing fuel consumption
US4493927A (en) * 1983-12-22 1985-01-15 The Dow Chemical Company Condensation polymers of sulfur compounds and norbornenyl compounds
US4639324A (en) * 1985-07-08 1987-01-27 Ethyl Petroleum Additives, Inc. Lubricating compositions
US4927552A (en) * 1988-05-02 1990-05-22 Ethyl Petroleum Additives, Inc. Lubricating oil composition
US4876375A (en) * 1988-05-02 1989-10-24 Ethyl Petroleum Additives, Inc. Norbornyl dithiocarbamates
US4836942A (en) * 1988-06-06 1989-06-06 Ethyl Petroleum Additives, Inc. Lubricant composition
FR2712824B1 (fr) * 1993-11-26 1996-02-02 Inst Francais Du Petrole Procédé de régénération de catalyseur.
EP0714970A1 (fr) * 1994-11-28 1996-06-05 Institut Français du Pétrole Hydrocarbures éthyléniques sulfurés par le soufre élémentaire en présence d'hydroxydes de métaux alcalins ou alcalino-terreux et en présence de glycols, polyglycols ou de leurs éthers alkyliques et/ou en présence d'eau
FR2729154A1 (fr) * 1995-01-10 1996-07-12 Inst Francais Du Petrole Hydrocarbures ethyleniques sulfures par le soufre elementaire en presence de carbonate ou d'hydrogenocarbonate alcalin, leur preparation et leurs utilisations
EP4368687B1 (en) 2022-11-10 2025-06-25 Afton Chemical Corporation Corrosion inhibitor and industrial lubricant including the same
GB2623137B (en) * 2022-11-10 2024-10-30 Afton Chemical Corp Corrosion inhibitor and industrial lubricant including the same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1195749A (en) * 1966-12-19 1970-06-24 Lubrizol Corp Sulfur-Containing Cycloaliphatic Reaction Products and their use in Lubricant Compositions
US3586700A (en) * 1969-02-19 1971-06-22 Union Carbide Corp 3,4,5-trithiatricyclo(5.2.1.0**2,6)decanes and derivatives
US3793203A (en) * 1971-05-17 1974-02-19 Sun Oil Co Lubricant comprising gem-structured organo compound

Also Published As

Publication number Publication date
NL159136C (enrdf_load_stackoverflow)
DE2417864A1 (de) 1974-10-31
ZA742357B (en) 1975-11-26
JPS5076103A (enrdf_load_stackoverflow) 1975-06-21
AU6775274A (en) 1975-10-16
US3882031A (en) 1975-05-06
JPS52107009A (en) 1977-09-08
NL7405010A (enrdf_load_stackoverflow) 1974-10-15
NL159136B (nl) 1979-01-15
FR2225431A1 (enrdf_load_stackoverflow) 1974-11-08
ATA304674A (de) 1977-06-15
IT1007869B (it) 1976-10-30
BR7402912D0 (pt) 1974-11-19
BE813603A (fr) 1974-07-31
JPS5347124B2 (enrdf_load_stackoverflow) 1978-12-19
JPS5347364B2 (enrdf_load_stackoverflow) 1978-12-20
DE2417864C3 (de) 1979-06-07
CA1047476A (en) 1979-01-30
AR208174A1 (es) 1976-12-09
DE2417864B2 (de) 1978-10-05
SE7711154L (sv) 1977-10-05
AT341537B (de) 1978-02-10
FR2225431B1 (enrdf_load_stackoverflow) 1978-11-17

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee