DE1570139A1 - Process for vulcanizing carbon black blends of natural rubber and ethylene propylene terpolymer rubber - Google Patents

Process for vulcanizing carbon black blends of natural rubber and ethylene propylene terpolymer rubber

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Publication number
DE1570139A1
DE1570139A1 DE19651570139 DE1570139A DE1570139A1 DE 1570139 A1 DE1570139 A1 DE 1570139A1 DE 19651570139 DE19651570139 DE 19651570139 DE 1570139 A DE1570139 A DE 1570139A DE 1570139 A1 DE1570139 A1 DE 1570139A1
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DE
Germany
Prior art keywords
rubber
carbon black
natural rubber
vulcanizing
blends
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Pending
Application number
DE19651570139
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German (de)
Inventor
Chandra Hrishikesh Roy
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Metzeler AG
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Metzeler AG
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Filing date
Publication date
Application filed by Metzeler AG filed Critical Metzeler AG
Publication of DE1570139A1 publication Critical patent/DE1570139A1/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C08L9/06—Copolymers with styrene
    • 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
    • C08K5/32—Compounds containing nitrogen bound to oxygen
    • C08K5/33—Oximes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L21/00—Compositions of unspecified rubbers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C08L23/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L7/00—Compositions of natural rubber
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/16—Elastomeric ethene-propene or ethene-propene-diene copolymers, e.g. EPR and EPDM rubbers

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Description

Verfahren zum Vulkanisieren von rußhaltigen Verschnittmischungen aus Naturkautschuk und Athylen-Propylen-Terpolymer-Kautschuk Die Erfindung bezieht sich auf ein Verfahren zum Vulkanisieren von rußhaltigen Verschnittmischungen aus Naturkautschuk und Athylen.Propylen-Terpolymer-Kautschuk, die neben einem schwefelhaltigen Vulkanisationssystem Zinkoxyd enthalten, unter Druck und Wärme.Process for the vulcanization of blends containing carbon black Natural rubber and ethylene-propylene terpolymer rubber The invention relates to a process for vulcanizing carbon black blends made from natural rubber and Athylen.Propylen-Terpolymer-Gummi, which in addition to a sulfur-containing vulcanization system Contain zinc oxide under pressure and heat.

Ungesättigte Polymere konnten bisher mit einem gesättigten Polymer nicht so zusammenvulkanisiert werden, daß ein praktisch verwendbares Vulkanisat entsteht.Unsaturated polymers could previously with a saturated polymer are not vulcanized together so that a practically usable vulcanizate arises.

Seit der Entdeckung des Äthylen-Propylen-Terpolymer-Kautschuks blieben Bestrebungen, dieses Polymer gemeinsam mit normalen ungesättigten Polymeren zu verarbeiten, ohne Errolg.Ever since the discovery of ethylene-propylene terpolymer rubber Efforts to process this polymer together with normal unsaturated polymers, without success

Bekannt sind bereits Naturkautschuk-Athylen-Propylen-Terpoly mer-Verschnittmischungen, die außer Ruß, Zinkoxyd und Stearinsäure ein aus Tetramethylthiurainrnonosulfid, Dibenzothiazyldisulfid und Schwefel enthaltendes Vulkanisationssystem in sich einschließen. Die Schnittfestigkeit von Vulkanisaten solcher Mischungen ist nicht sehr gut.Already known are natural rubber-ethylene-propylene-terpolymer blends, which, in addition to carbon black, zinc oxide and stearic acid, are made from tetramethylthiurainonosulfide, Vulcanization system containing dibenzothiazyl disulfide and sulfur in themselves lock in. The cut resistance of vulcanizates of such mixtures is not very good.

Bekannt sind ferner auch Naturkautschuk-Xthylen-Propylen Mischpolymerisat-Verschnittmischungen, die als Vulkanisationssystem Dicumyl-Peroxyd enthalten. Dicumyl-Peroxyd ist Jedoch durch seinen unangenehmen, in ungemischtem, gemischtem und vulkanisiertem Zustande gegebenen Geruch sowohl bei der Verarbeitung als auch bei dem Anwenden der Vulkanisate außerordentlich lästig und kann deshalb nicht verwendet werden.Also known are natural rubber-ethylene-propylene mixed polymer blends, which contain dicumyl peroxide as a vulcanization system. However, dicumyl peroxide is by its unpleasant, unmixed, mixed and vulcanized state given odor both during processing and when using the vulcanizates extremely annoying and therefore cannot be used.

Es wurde nun gefunden, daß mit aus Athylen-Propylen-Terpolymerkautschuk-Naturkautschukverschnitten dann Uberraschend praktisch verwertbare Vulkanisate erzeugt werden können, wenn die Verschnittmischungen zumindest Alterungsschutzmittel, Zinkstearat, Weichmacher sowie Kieselsäure enthalten und deren Vulkanisationssystem aus Dibenzothiazyldisulfid, Tetramethylthiuramdisulfid, Mercaptobenzothiazol, Diphenylguanidin, pp'-Dibenzoylchinondioxim, Phthalsäureanhydrid und weniger als einem Gewichtsteil elementarem Schwefel, bezogen auf 100 Gewichtsteile Gesamtkautschuk, zusammengesetzt sind.It has now been found that blends of ethylene-propylene terpolymer rubber with natural rubber then surprisingly practically usable vulcanizates can be produced if the blend mixtures at least anti-aging agents, zinc stearate, plasticizers as well as silica and their vulcanization system made of dibenzothiazyl disulfide, Tetramethylthiuram disulfide, mercaptobenzothiazole, diphenylguanidine, pp'-dibenzoylquinone dioxime, Phthalic anhydride and less than one part by weight elemental sulfur to 100 parts by weight of total rubber.

In den nachfolgendon Mischungabeispielen I bis III sind bekannte und allgemion übliele Naturkautschuk (I)- und Butylkautschukauslitäten (II) oimer Naturkautschuk-Äthylen-Propylen Terpolymer-Verschnittquslität (III) zum Vergleich gegenübergestellt.In the following Mixture Examples I to III are known and Generally common natural rubber (I) and butyl rubber auslities (II) or natural rubber-ethylene-propylene Terpolymer blend quality (III) compared for comparison.

Mischung Gewichtsteile Naturkautschuk (Para II) 95,-Styaplbutadicnkautschuk (Synpol 1500) 5,-Voichmecher (Maftolen) 1,8 Sirkhydrat 10,-Synthetiche Pettsäure (Aktoplast OL 100) 1,2 Stearinsäure (Stearin P) 2,-Mineralgtmmi als Füllstoff (Mineralgi) 1,6 Wachs (Osoberit P) 2,5 Kleber (IO-Karz) 1,6 Phenylalphannaphty lamin (Phenyl alpha) 0,6 Phenylbetannaphtylamin (Aldol beta SchJ 0,6 Abbammittel (Reimzit IV gran) 0,02 Azetylenruß (Ruß 36) 22,3 halbaktier Ruß (Ruß E) 11,1 Schwefel (Ölsehwefel o,2) 2,6 Dibenzothiasyldisulfid mit Öl (Ölvulkazit M) 0,6 Diphenylguanidin mit Öl (Ölvalkazit B) o, 33 Prüfergebaisse: Heizung bei 143°C 25 Min 35 Min Modul bei 300 % kg/cm2 40 40 Modul bei Tco l?ß../Cb 114 llo Zugfestigkeit kg/cm2 215 oo Bruchdchnung % % 650 645 Shore-Härte Sheregrade Ab 46 Elastizität % 53 54 Mischung TI Gewichtsteile Butylkautschuk (Butyl Sooo S) 100,-Paraffinöl-paraffinisches Öl (Forum 40) 17,-Zinkoxyd (Zink I RS) 5,-Poymeres p-Dinitrosobenzol (Poliao) o,l Kleber (KO-Harz) 1,-halbaktiver Rus (Ruß Durex 0) 30,- Portsetzung Mischung II Gewichtsteile Ofenruß (Rus Coram A) 30,-Schwoefel (Ölschwefel 0,2) 2,2 Tetramethylthiuramdisulfid (Vulkazit Th) 1,-Mereaptobemsothiazol (Vulkazit C) o*5 Prüfergebnisse: Heisung boi 1620 o So Min 30 Min Modul bei 300 % kg/cm2 50 54 Modul bei 500 % kg/cm2 82 -Zugfestigkeit kg/cm2 83 80 Bruchdehnung % 505 465 Shore-Härte Shoregrade 55 55 Elastizität ffi 17 16 Mischung III Gewichtsteile Naturkautschuk (Para II) 70,-Äthylen-Propylen-Terpolymer-Kautschuk 2 2) 30,-Butylkautschuk (Eutyl 218) -q Weichmacher (Naftolen) 11, Zinkoxyd (Zink I RS) 1,5 Zinkstearat 3,5 Mereaptobenzoimidazol (Weiß MB) 0,56 N-phenyl-N'-isopropyl-p-phenylendiamin(Aldol 4010 MA) 0,5 Wachs (Ozokerit P) 2,5 Kleber (Cumaronharz Flüssig) 3,-Abbaumittel (Renasit IV gran) 0,1 Kieselsäure (VN 3) 10,-halbaktiver Rus (Ruß E) 20,-Ofenruß (Ruß Ceram 3) Ihtalsäureanhydrid (Vulkalent B) 1,-Schwefel (Ölschwefel 0,2) 0,66 Mereaptobenzothiamol (Vulkazit C) 0,5 Tetremethylthiuramidsulfid (Vulkazit Th) 0,1 Dibenzothiazylidsulfid mit Öl (Ölvulkazit M) 2,6 Diphonylguanidin mit Öl (Ölvulkazit D) 0,33 pp'-Dibenzoylchinondioxim (Dibenzo GMP) 1,5 Prüfergebnisse: Heisung bot 143°C 35 Min Go Min Modul bei 3oo % kg/cm2 58 59 Modul bi 500 % kg/cm2 117-Zugrestigkeit kg/cm2 116 109 Bruchdehnung % 495 40 Shore-Härte shoregrade 59 Go Elastizität % 41 42 Lie Ergebnisse der Prüfung zur Mischung III liegen zwischen denem der Vulkanisate nch den Mischungen 1 und II, d.h. etwa zwischen den Vulkanisaten von Mischungen mit 100 % Naturkautschuk bzw. 100 % Butylkautschuk. Der Äthylen-Propylen-Terpolymer-Kautschuk-Naturkautschukverschnitt erweist sich in bezug auf Hitzebeständigkeit besser als das haturkautschukvulkanisat zur Mischung I. Das Verschnittvulkanisat der Mischung III kann vorteilhaft zu technischen und Autoschläuchen, Isolierstreifen und Innenplatten zu Fahrzeugluftreifen sowie zu zahlreichen anderen technischen Gummiartikeln und Mantelatoffen verunbeitet werden.Mixture parts by weight of natural rubber (Para II) 95, -Styaplbutadicnkautschuk (Synpol 1500) 5, -Voichmecher (Maftolen) 1,8 Sirkhydrat 10, -Synthetic fatty acid (Aktoplast OL 100) 1,2 stearic acid (Stearin P) 2, -Mineralgtmmi as filler (Mineralgi) 1.6 wax (Osoberit P) 2.5 glue (IO-Karz) 1.6 phenylalphannaphty lamin (Phenyl alpha) 0.6 phenylbetannaphtylamine (Aldol beta SchJ 0.6 decongestant (Reimzit IV gran) 0.02 acetylene black (carbon black 36) 22.3 semi-active carbon black (carbon black E) 11.1 sulfur (oleosulfur o, 2) 2.6 dibenzothiasyl disulfide with oil (oil volkacite M) 0.6 diphenylguanidine with oil (Ölvalkazit B) o, 33 testers: heating at 143 ° C 25 min 35 min module at 300 % kg / cm2 40 40 module at Tco l? ß ../ Cb 114 llo tensile strength kg / cm2 215 oo elongation at break %% 650 645 Shore hardness Shere degrees From 46 elasticity% 53 54 Mixture TI parts by weight Butyl rubber (Butyl Sooo S) 100, -paraffin oil-paraffinic oil (Forum 40) 17, -zinc oxide (Zinc I RS) 5, -Poymeres p-Dinitrosobenzol (Poliao) o, l adhesive (KO resin) 1, -semi-active Rus (soot Durex 0) 30, - Porting mixture II parts by weight of furnace black (Rus Coram A) 30, -Schwoefel (oil sulfur 0.2) 2.2 tetramethylthiuram disulfide (vulkacite Th) 1, -Mereaptobemsothiazole (Vulkacite C) o * 5 Test results: Heisung boi 1620 o So min 30 min module at 300% kg / cm2 50 54 module at 500% kg / cm2 82 tensile strength kg / cm2 83 80 Elongation at break% 505 465 Shore hardness Shore grade 55 55 Elasticity ffi 17 16 Mixture III parts by weight natural rubber (Para II) 70, -Ethylene-propylene-terpolymer-rubber 2 2) 30, -Butyl rubber (Eutyl 218) -q plasticizer (Naftolen) 11, zinc oxide (zinc I RS) 1.5 zinc stearate 3.5 mereaptobenzoimidazole (White MB) 0.56 N-phenyl-N'-isopropyl-p-phenylenediamine (Aldol 4010 MA) 0.5 wax (Ozokerit P) 2.5 glue (coumarone resin liquid) 3, -Degradation agent (Renasit IV gran) 0.1 Silicic acid (VN 3) 10. -semi-active carbon black (carbon black E) 20.00 furnace carbon black (Soot Ceram 3) Ihtalic anhydride (Vulkalent B) 1, -Sulfur (oil sulfur 0.2) 0.66 Mereaptobenzothiamol (Vulkazit C) 0.5 Tetremethylthiuramide sulfide (Vulkazit Th) 0.1 Dibenzothiazylide sulfide with oil (oil volkacite M) 2,6 Diphonylguanidine with oil (oil volcacite D) 0.33 pp'-dibenzoylquinone dioxime (Dibenzo GMP) 1.5 Test results: Heating offered 143 ° C 35 min go min module at 3oo% kg / cm2 58 59 module at 500% kg / cm2 117 tensile strength kg / cm2 116 109 Elongation at break% 495 40 Shore hardness, shore grade 59 Go elasticity% 41 42 Lie results of the test for mixture III are between between the vulcanizates after mixtures 1 and II, i.e. between the vulcanizates of mixtures with 100% natural rubber or 100% butyl rubber. The ethylene-propylene-terpolymer-rubber-natural rubber blend In terms of heat resistance, it proves to be better than the hatur rubber vulcanizate for mixture I. The blending vulcanizate of mixture III can be advantageous to technical and car hoses, insulating strips and inner panels for pneumatic vehicle tires as well be processed into numerous other technical rubber articles and jacket materials.

Es ist klar, daß ähnlich vorteilhafte Haturkautschuk-Butylkautschuk-Verschnitt-Vulkanisate auch mit gegenüber der Mischung III abweichenden Gewichtsteilen der Mischungsbestandteile erreichbar sind.It is clear that similarly advantageous natural rubber-butyl rubber blend vulcanizates also with parts by weight of the mixture constituents which differ from mixture III are attainable.

Claims (2)

Patentansprüche 1. Verfahren zum Vulkanisieren von rußhaltigen Verschnittmischungen aus Naturkautschuk und Athylen-Propylen-Terpolymer-Kautschuk, die neben einem schwefelhaltigen Vulkanisationssystem Zinkoxyd enthalten, unter Druck und Wärme, dadurch gekennzeichnet, daß solche Verschnittmischungen vulkanisiert werden, die zumindest Alterungsschutzmittel, Zinkstearat, Weichmacher sowie Kieselsäure enthalten und deren Vulkanisatlonssystem aus Dibenzothiazyldisulfid, Tetramethylthiuramdisulfid, Mercaptobenzothiazol, Diphenylguanidin, pp'-Dibenzyolchinondioxim, Phthalsäureanhydrid und weniger als einem Gewichtsteil elementarem Schwefel, bezogen auf 100 Gewichtsteile Gesamtkautschuk, zusammengesetzt ist. Claims 1. A method for vulcanizing carbon black blends made of natural rubber and ethylene-propylene terpolymer rubber, in addition to a sulfur-containing Vulcanization system containing zinc oxide, under pressure and heat, characterized by that such blends are vulcanized that contain at least anti-aging agents, Contain zinc stearate, plasticizers and silica and their vulcanization system from dibenzothiazyl disulfide, tetramethylthiuram disulfide, mercaptobenzothiazole, diphenylguanidine, pp'-dibenzyolquinone dioxime, phthalic anhydride and less than one part by weight elemental sulfur, based on 100 parts by weight of total rubber is. 2. Verfahren zum Vulkanisieren von rußhaltigen Verschnittmischungen aus Naturkautschuk und Butylkautschuk nach Anspruch 1, dadurch gekennzeichnet, daß mindestens ein Teil der Alterungsschutzmittel aus Mercaptobenzimidazol und N-phenyl-N'-isopropyl p-phenylendiamin besteht.2. Process for vulcanizing blends containing carbon black made of natural rubber and butyl rubber according to claim 1, characterized in that at least some of the anti-aging agents made from mercaptobenzimidazole and N-phenyl-N'-isopropyl p-phenylenediamine.
DE19651570139 1965-10-28 1965-10-28 Process for vulcanizing carbon black blends of natural rubber and ethylene propylene terpolymer rubber Pending DE1570139A1 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
DEM0067094 1965-10-28
DEM0067092 1965-10-28
DEM0067091 1965-10-28
DEM0067093 1965-10-28
DEM0067089 1965-10-28
DEM0067090 1965-10-28

Publications (1)

Publication Number Publication Date
DE1570139A1 true DE1570139A1 (en) 1969-08-28

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ID=27544885

Family Applications (6)

Application Number Title Priority Date Filing Date
DE19651570141 Pending DE1570141A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing carbon black blends of natural rubber and butyl rubber
DE19651570138 Pending DE1570138A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing carbon black blends of natural rubber and butyl rubber
DE19651570136 Pending DE1570136A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing blends of butyl rubber and, optionally oil-expanded, butadiene styrene rubber
DE19651570139 Pending DE1570139A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing carbon black blends of natural rubber and ethylene propylene terpolymer rubber
DE19651570137 Pending DE1570137A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing blends consisting of natural rubber, butyl rubber and ethylene terpolymer rubber
DE19651570140 Pending DE1570140A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing carbon black blends of natural rubber and butyl rubber

Family Applications Before (3)

Application Number Title Priority Date Filing Date
DE19651570141 Pending DE1570141A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing carbon black blends of natural rubber and butyl rubber
DE19651570138 Pending DE1570138A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing carbon black blends of natural rubber and butyl rubber
DE19651570136 Pending DE1570136A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing blends of butyl rubber and, optionally oil-expanded, butadiene styrene rubber

Family Applications After (2)

Application Number Title Priority Date Filing Date
DE19651570137 Pending DE1570137A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing blends consisting of natural rubber, butyl rubber and ethylene terpolymer rubber
DE19651570140 Pending DE1570140A1 (en) 1965-10-28 1965-10-28 Process for vulcanizing carbon black blends of natural rubber and butyl rubber

Country Status (2)

Country Link
DE (6) DE1570141A1 (en)
GB (1) GB1127102A (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2202852B (en) * 1987-03-31 1991-07-24 Acushnet Co Rubber composition for use with potable water
US4946593A (en) * 1987-03-31 1990-08-07 Acushnet Company Rubber composition for use with potable water
US5405105A (en) * 1993-05-28 1995-04-11 Hudson Valley V/Stol Aircraft, Inc. Tilt wing VTOL aircraft
DE102010060355B4 (en) 2010-11-04 2022-01-13 Continental Reifen Deutschland Gmbh Rubber mixture and its use for the manufacture of a tyre, belt, strap or tube
JP6068949B2 (en) * 2012-09-05 2017-01-25 住友ゴム工業株式会社 Rubber composition for tire, pneumatic tire and method for preventing tire discoloration
JP6068950B2 (en) * 2012-09-05 2017-01-25 住友ゴム工業株式会社 Rubber composition for tire, pneumatic tire and method for preventing tire discoloration
JP6068951B2 (en) * 2012-09-05 2017-01-25 住友ゴム工業株式会社 Rubber composition for tire, pneumatic tire and method for preventing tire discoloration

Also Published As

Publication number Publication date
GB1127102A (en) 1968-09-11
DE1570140A1 (en) 1969-08-14
DE1570141A1 (en) 1969-05-22
DE1570136A1 (en) 1970-03-26
DE1570138A1 (en) 1969-08-28
DE1570137A1 (en) 1969-08-21

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SH Request for examination between 03.10.1968 and 22.04.1971