GB1399239A - Piperidine derivatives - Google Patents

Piperidine derivatives

Info

Publication number
GB1399239A
GB1399239A GB2845872*[A GB2845872A GB1399239A GB 1399239 A GB1399239 A GB 1399239A GB 2845872 A GB2845872 A GB 2845872A GB 1399239 A GB1399239 A GB 1399239A
Authority
GB
United Kingdom
Prior art keywords
compound
radical
reacting
hydrogen
organic
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
GB2845872*[A
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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 BE792043D priority Critical patent/BE792043A/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Priority to GB2845872*[A priority patent/GB1399239A/en
Priority to SE7215112A priority patent/SE454277B/en
Priority to IL40888A priority patent/IL40888A/en
Priority to PL15915472A priority patent/PL90214B1/pl
Priority to CH263676A priority patent/CH585714A5/xx
Priority to CH1729872A priority patent/CH586252A5/xx
Priority to CH263776A priority patent/CH585715A5/en
Priority to CS728130A priority patent/CS190377B2/en
Priority to SU7201851503A priority patent/SU584795A3/en
Priority to IT32252/72A priority patent/IT971346B/en
Priority to ES409079A priority patent/ES409079A1/en
Priority to FR7242421A priority patent/FR2182789B1/fr
Priority to RO7283383A priority patent/RO71050A/en
Priority to RO7283993A priority patent/RO64573A/en
Priority to HUCI1307A priority patent/HU167244B/hu
Priority to CA157,753A priority patent/CA997767A/en
Priority to JP47121099A priority patent/JPS5920709B2/en
Priority to DE19722258752D priority patent/DE2258752A1/en
Priority to AT1019972A priority patent/AT324009B/en
Priority to NLAANVRAGE7216278,A priority patent/NL174942C/en
Priority to DE2258752A priority patent/DE2258752C2/de
Priority to DD167212A priority patent/DD106190A5/xx
Priority to FR7318100A priority patent/FR2183294B1/fr
Priority to FR7318099A priority patent/FR2183293B1/fr
Priority to US05/577,501 priority patent/US4046737A/en
Priority to US05/577,534 priority patent/US4049647A/en
Priority to US05/577,502 priority patent/US4021432A/en
Publication of GB1399239A publication Critical patent/GB1399239A/en
Priority to HK478/77A priority patent/HK47877A/en
Priority to US05/938,974 priority patent/USRE31342E/en
Priority to US05/938,849 priority patent/USRE31343E/en
Priority to MY197825A priority patent/MY7800025A/en
Expired legal-status Critical Current

Links

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
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Hydrogenated Pyridines (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

Abstract

1399239 o - Substituted - (4 - hydroxy- 2,2,6,6 - tetramethylpiperidines) CIBA-GEIGY AG 30 Nov 1972 [30 Nov 1971 17 June 1972 28 July 1972] 55487/71 28458/72 35473/72 Headings C2B C2C and C2P [Also in Division C3] The invention comprises compounds I, II and III where R 1 and R 2 are organic radicals; n is 1, 2, 3 or 4 in Formula (I) and is 1 or 2 in Formula (II); q is 1 or 2; R 3 is an organic or inorganic, e.g. borate or phosphate radical having a valency appropriate to n, R<SP>I</SP> and R<SP>II</SP> are C 1-4 alkyl or are linked to form a C 5-12 cycloalkyl radical; R<SP>III</SP> and R<SP>IV</SP> are C 1-12 alkyl or are linked to form a C 5-12 cycloalkyl radical; Y is hydrocarbyl; R is hydrogen or an organic radical; and R 12 is hydrogen or an optionally substituted hydrocarbyl radical, and their preparation by esterification or etherification using known methods; reacting a compound IX with a compound capable of introducing the group R 1 or where R 1 and R 3 are identical carrying out the said reaction with a compound XI; or by reacting a compound XVII with an isocyanate R 12 (NCO) q . 4-Hydroxypiperidines (A) are made by reacting a compound (B) with a Grignard reagent and hydrolysing the product, R<SP>1</SP> 1 being R 1 or hydrogen The compounds of the invention are stabilizers for polymers.
GB2845872*[A 1971-11-30 1972-06-17 Piperidine derivatives Expired GB1399239A (en)

Priority Applications (32)

Application Number Priority Date Filing Date Title
BE792043D BE792043A (en) 1971-11-30 PIPERIDINE DERIVATIVES USED TO STABILIZE ORGANIC MATERIALS
GB2845872*[A GB1399239A (en) 1971-11-30 1972-06-17 Piperidine derivatives
SE7215112A SE454277B (en) 1971-11-30 1972-11-21 THE USE OF PIPERIDE COMPOUNDS AS A LIGHT PROTECTION FOR ORGANIC POLYMERS
IL40888A IL40888A (en) 1971-11-30 1972-11-21 Piperidine derivatives their preparation and their use as stabilisers for polymeric materials
PL15915472A PL90214B1 (en) 1971-11-30 1972-11-28
CH263676A CH585714A5 (en) 1971-11-30 1972-11-28
CH1729872A CH586252A5 (en) 1971-11-30 1972-11-28
CH263776A CH585715A5 (en) 1972-06-17 1972-11-28 Piperidine derivs and prepn - and use as photo/thermal stabilisers for org (polymer) materials
HUCI1307A HU167244B (en) 1971-11-30 1972-11-29
SU7201851503A SU584795A3 (en) 1971-11-30 1972-11-29 Stabilized polymeric composition
IT32252/72A IT971346B (en) 1971-11-30 1972-11-29 PIPERIDINE DERIVATIVES
ES409079A ES409079A1 (en) 1971-11-30 1972-11-29 Piperidyl carboxylates
FR7242421A FR2182789B1 (en) 1971-11-30 1972-11-29
RO7283383A RO71050A (en) 1971-11-30 1972-11-29 PROCEDURE FOR PREPARING PIPERIDINE DERIVATIVES
RO7283993A RO64573A (en) 1971-11-30 1972-11-29 PROCESS FOR THE PREPARATION OF PIPERYDINE DERIVATIVES
CS728130A CS190377B2 (en) 1971-11-30 1972-11-29 Process for the stabilization of olefines,olefine copolymers,styrene polymers,polyamides and polyuretanes
CA157,753A CA997767A (en) 1971-11-30 1972-11-29 Piperidine derivatives
DE2258752A DE2258752C2 (en) 1971-11-30 1972-11-30
DE19722258752D DE2258752A1 (en) 1971-11-30 1972-11-30 NEW PIPERIDIN DERIVATIVES
AT1019972A AT324009B (en) 1971-11-30 1972-11-30 PROCESS FOR STABILIZING POLYMERIC MATERIAL AGAINST THE DAMAGING INFLUENCE OF LIGHT AND OR. OR HEAT
NLAANVRAGE7216278,A NL174942C (en) 1971-11-30 1972-11-30 METHOD FOR PREPARING 4-PIPERIDINOL DERIVATIVES, AND METHOD FOR STABILIZING ORGANIC MATERIAL AGAINST DEGRADATION BY THE ACTION OF LIGHT AND / OR HEAT.
JP47121099A JPS5920709B2 (en) 1971-11-30 1972-11-30 Stabilized organic material composition
DD167212A DD106190A5 (en) 1971-11-30 1972-11-30
FR7318100A FR2183294B1 (en) 1971-11-30 1973-05-16
FR7318099A FR2183293B1 (en) 1971-11-30 1973-05-16
US05/577,534 US4049647A (en) 1971-11-30 1975-05-14 Bis piperidyl carboxylates
US05/577,501 US4046737A (en) 1971-11-30 1975-05-14 Piperidine derivatives
US05/577,502 US4021432A (en) 1971-11-30 1975-05-14 Piperidine derivatives
HK478/77A HK47877A (en) 1971-11-30 1977-09-15 New piperidine derivatives
US05/938,974 USRE31342E (en) 1971-11-30 1978-09-01 Piperidyl carboxylates
US05/938,849 USRE31343E (en) 1971-11-30 1978-09-01 Piperidine derivatives
MY197825A MY7800025A (en) 1971-11-30 1978-12-31 New piperidine derivatives

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB5548771 1971-11-30
GB2845872*[A GB1399239A (en) 1971-11-30 1972-06-17 Piperidine derivatives
GB3547372 1972-07-28

Publications (1)

Publication Number Publication Date
GB1399239A true GB1399239A (en) 1975-06-25

Family

ID=27258723

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2845872*[A Expired GB1399239A (en) 1971-11-30 1972-06-17 Piperidine derivatives

Country Status (21)

Country Link
US (2) USRE31342E (en)
JP (1) JPS5920709B2 (en)
AT (1) AT324009B (en)
BE (1) BE792043A (en)
CA (1) CA997767A (en)
CH (2) CH586252A5 (en)
CS (1) CS190377B2 (en)
DD (1) DD106190A5 (en)
DE (2) DE2258752C2 (en)
ES (1) ES409079A1 (en)
FR (3) FR2182789B1 (en)
GB (1) GB1399239A (en)
HK (1) HK47877A (en)
HU (1) HU167244B (en)
IL (1) IL40888A (en)
IT (1) IT971346B (en)
MY (1) MY7800025A (en)
NL (1) NL174942C (en)
RO (2) RO71050A (en)
SE (1) SE454277B (en)
SU (1) SU584795A3 (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2627688A1 (en) * 1975-06-30 1977-01-27 Ciba Geigy Ag DISABLED PIPERIDINE CARBONIC ACIDS, METAL SALTS THEREOF AND THEREFORE STABILIZED POLYMERS
EP0249145A1 (en) * 1986-06-11 1987-12-16 ENICHEM SYNTHESIS S.p.A. Process for preparation of N-allyl-piperidine derivatives
US4927898A (en) * 1988-09-06 1990-05-22 Union Carbide Chemicals And Plastics Company Inc. Polysiloxanes with sterically hindered heterocyclic moiety
GB2249093A (en) * 1990-10-23 1992-04-29 Nat Res Dev Piperidine derivatives and their use in pharmaceutical compositions
WO1997013752A1 (en) * 1995-10-12 1997-04-17 Ciba Specialty Chemicals Holding Inc. Thermally stable hindered amines as stabilizers
CN1041317C (en) * 1991-09-30 1998-12-23 黑蒙特股份公司 Monomeric hindered amine esters of monocarboxylic resin acids and olefin polymer compositions stabilized therewith.
US6525131B1 (en) 2001-09-18 2003-02-25 Crompton Corporation Aromatic diamine polyurethane curatives with improved stability

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1402888A (en) * 1972-10-21 1975-08-13 Ciba Geigy Ag Piperidine derivatives
CH589056A5 (en) * 1973-12-10 1977-06-30 Ciba Geigy Ag
JPS51132242A (en) * 1975-03-22 1976-11-17 Adeka Argus Chem Co Ltd Light stabilising composition for synthetic resin
DE2718458A1 (en) * 1976-05-04 1977-11-24 Ciba Geigy Ag NEW STABILIZERS
DE2805838A1 (en) * 1977-02-24 1978-08-31 Ciba Geigy Ag NEW 4-ACYLOXYPIPERIDINE
JPS5469162A (en) * 1977-11-15 1979-06-02 Dainichi Seika Kogyo Kk Stabilized urethane polymer
DE2861955D1 (en) * 1977-12-02 1982-09-02 Ciba Geigy Ag Malonic acid derivatives of sterically hindered piperidines, process for their preparation and stabilised organic matter
JPS559064A (en) * 1978-07-03 1980-01-22 Sankyo Co Ltd Novel stabilizer
ATE4992T1 (en) * 1978-07-25 1983-10-15 Imperial Chemical Industries Plc POLYOLEFIN ARTICLES STERILIZABLE BY GAMMA RADIATION.
US4311820A (en) * 1979-02-14 1982-01-19 Ciba-Geigy Corporation Homopolymers and copolymers of vinyl ethers of polyalkylpiperidinols and their use as stabilizers for plastics
IT7928324A0 (en) * 1979-12-21 1979-12-21 Chimosa Chimica Organica Spa PIPERIDINE DERIVATIVES, STABILIZERS FOR SYNTHETIC POLYMERS.
DE3201415A1 (en) * 1981-01-28 1982-08-26 Sandoz-Patent-GmbH, 7850 Lörrach 4-Aminomethylpolyalkylpiperidines
CS229069B1 (en) 1981-09-23 1984-05-14 Julius Durmis Composition for stabilizing polymers and method of preparing same
JPS58113236A (en) * 1981-12-28 1983-07-06 Tounen Sekiyu Kagaku Kk Polyolefin composition
US4590268A (en) * 1982-05-10 1986-05-20 Ciba-Geigy Corporation Process for the preparation of 1-diorganocarbamoyl-polyalkylpiperidines
US4569997A (en) * 1982-08-10 1986-02-11 Ciba Geigy Corporation Polyalkylpiperidine compounds
DE3312611A1 (en) * 1983-04-08 1984-10-11 Röhm GmbH, 6100 Darmstadt METHOD FOR PRODUCING UV-PROTECTED MULTILAYERED PLASTIC MOLDED BODIES
DE3345376A1 (en) * 1983-12-15 1985-06-27 Basf Ag, 6700 Ludwigshafen FURAN-3-CARBONSAEUR DERIVATIVES
DE3522678A1 (en) * 1985-06-25 1987-01-08 Basf Ag TETRAHYDROFURANCARBONSAEUR DERIVATIVES
JPS6248745A (en) * 1985-08-28 1987-03-03 Mitsubishi Petrochem Co Ltd Polyolefin composition
IT1189095B (en) * 1986-05-02 1988-01-28 Enichem Sintesi PROCEDURE FOR THE SYNTHESIS OF ALLILATED DERIVATIVES OF 2,2,6,6-TETRALKYLPIPERIDINOLS
DE3724222A1 (en) * 1987-07-22 1989-02-02 Huels Chemische Werke Ag LIGHT STABILIZERS
IT1222647B (en) * 1987-09-11 1990-09-05 Eniricerche Spa AMERICAN COMPOUNDS STERICALLY PREVENTED AND PROCEDURE FOR THEIR PREPARATION
DE3735577A1 (en) 1987-10-21 1989-05-03 Basf Ag MIXTURE FOR STABILIZING POLYURETHANES
EP0344114B1 (en) * 1988-05-27 1994-04-06 Ciba-Geigy Ag Unsaturated derivatives of 2,2,6,6-tetramethyl piperidine
ES2050274T3 (en) * 1988-06-14 1994-05-16 Ciba Geigy Ag PROCEDURE FOR THE PHOTOCHEMICAL STABILIZATION OF UNDYED AND DYED POLYPROPYLENE FIBERS.
DE3844356A1 (en) * 1988-12-30 1990-07-05 Basf Ag 4- (2'-ETHYLHEXANOYLOXY) -2,2,6,6-TETRAMETHYL PIPERIDINE
US5180830A (en) * 1991-04-24 1993-01-19 Himont Incorporated Process for preparing hindered amine light stabilizers
NL9101619A (en) * 1991-09-25 1993-04-16 Harcros Chemicals Bv STABILIZERS FOR ORGANIC MATERIALS.
EP1184442A1 (en) * 2000-08-30 2002-03-06 Clariant International Ltd. Liquid crystal mixture
US6492521B2 (en) 2000-11-03 2002-12-10 Cytec Technology Corp. Hindered amine light stabilizers based on multi-functional carbonyl compounds and methods of making same
US6727300B2 (en) 2000-11-03 2004-04-27 Cytec Technology Corp. Polymeric articles containing hindered amine light stabilizers based on multi-functional carbonyl compounds
US6545156B1 (en) * 2000-11-03 2003-04-08 Cytec Technology Corp. Oligomeric hindered amine light stabilizers based on multi-functional carbonyl compounds and methods of making same
US6414155B1 (en) 2000-11-03 2002-07-02 Cytec Technology Corp. Oligomeric hindered amine light stabilizers based on multi-functional carbonyl compounds and methods of making same
EP1444222A1 (en) * 2001-10-23 2004-08-11 Council Of Scientific And Industrial Research Tinuvin p-hindred amine light stabilizer and derivatives thereof, and a process for the preparation thereof
US6492518B1 (en) 2001-10-30 2002-12-10 Council Of Scientific And Industrial Research Tinuvin P-hindred amine light stabilizer and derivatives thereof
JP5283153B2 (en) 2007-10-25 2013-09-04 株式会社Ａｄｅｋａ Synthetic resin composition and automotive interior / exterior material
EP2270101B1 (en) 2008-03-10 2016-01-13 Adeka Corporation Synthetic resin composition, and automotive interior/exterior material comprising the same
JP5656213B2 (en) * 2010-01-19 2015-01-21 日本化薬株式会社 Carboxylic acid composition and curable resin composition containing the carboxylic acid composition
CN105358528B (en) * 2013-07-08 2021-07-20 巴斯夫欧洲公司 Novel light stabilizers
DE102013012622A1 (en) * 2013-07-30 2015-02-05 Clariant lnternational Ltd New sterically hindered cyclic amines
US20170190874A1 (en) * 2014-05-21 2017-07-06 Solvay Specialty Polymers Usa, Llc Stabilizer Compounds
DE102015000124A1 (en) * 2015-01-07 2016-07-07 Clariant International Ltd. Process for the stabilization of polyamides

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2746964A (en) * 1953-11-02 1956-05-22 Lakeside Lab Inc Dicarboxylic acid esters of nu-alkyl-3-hydroxypiperidine and salts thereof
US3120540A (en) * 1961-09-25 1964-02-04 Warner Lambert Pharmaccutical Bis (polymethyl)-4-piperidinol alkanoates
US3640928A (en) * 1968-06-12 1972-02-08 Sankyo Co Stabilization of synthetic polymers
US3705166A (en) * 1969-08-15 1972-12-05 Sankyo Co Acrylic acid derivatives of 2,2,6,6-tetramethylpiperidines
NL154241C (en) * 1971-01-29 1900-01-01
US4021432A (en) * 1971-11-30 1977-05-03 Ciba-Geigy Corporation Piperidine derivatives
US4049647A (en) * 1971-11-30 1977-09-20 Ciba-Geigy Corporation Bis piperidyl carboxylates

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2627688A1 (en) * 1975-06-30 1977-01-27 Ciba Geigy Ag DISABLED PIPERIDINE CARBONIC ACIDS, METAL SALTS THEREOF AND THEREFORE STABILIZED POLYMERS
EP0249145A1 (en) * 1986-06-11 1987-12-16 ENICHEM SYNTHESIS S.p.A. Process for preparation of N-allyl-piperidine derivatives
US4927898A (en) * 1988-09-06 1990-05-22 Union Carbide Chemicals And Plastics Company Inc. Polysiloxanes with sterically hindered heterocyclic moiety
GB2249093A (en) * 1990-10-23 1992-04-29 Nat Res Dev Piperidine derivatives and their use in pharmaceutical compositions
CN1041317C (en) * 1991-09-30 1998-12-23 黑蒙特股份公司 Monomeric hindered amine esters of monocarboxylic resin acids and olefin polymer compositions stabilized therewith.
WO1997013752A1 (en) * 1995-10-12 1997-04-17 Ciba Specialty Chemicals Holding Inc. Thermally stable hindered amines as stabilizers
US6525131B1 (en) 2001-09-18 2003-02-25 Crompton Corporation Aromatic diamine polyurethane curatives with improved stability
US7781518B2 (en) 2001-09-18 2010-08-24 Crompton Corporation Aromatic diamine polyurethane curatives with improved stability

Also Published As

Publication number Publication date
DE2258752C2 (en) 1989-10-26
IT971346B (en) 1974-04-30
HK47877A (en) 1977-09-23
IL40888A0 (en) 1973-01-30
HU167244B (en) 1975-09-27
RO71050A (en) 1981-09-24
IL40888A (en) 1976-10-31
FR2183293A1 (en) 1973-12-14
USRE31343E (en) 1983-08-09
DD106190A5 (en) 1974-06-05
FR2183294B1 (en) 1978-05-26
FR2182789A1 (en) 1973-12-14
CH586252A5 (en) 1977-03-31
AT324009B (en) 1975-08-11
ES409079A1 (en) 1976-04-16
JPS4865180A (en) 1973-09-08
NL174942C (en) 1984-09-03
FR2183294A1 (en) 1973-12-14
DE2258752A1 (en) 1973-06-07
SE454277B (en) 1988-04-18
RO64573A (en) 1979-08-15
NL7216278A (en) 1973-06-04
BE792043A (en) 1973-05-29
CH585714A5 (en) 1977-03-15
USRE31342E (en) 1983-08-09
FR2182789B1 (en) 1976-01-30
CA997767A (en) 1976-09-28
CS190377B2 (en) 1979-05-31
NL174942B (en) 1984-04-02
FR2183293B1 (en) 1977-07-29
JPS5920709B2 (en) 1984-05-15
MY7800025A (en) 1978-12-31
SU584795A3 (en) 1977-12-15

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