NO116204B - - Google Patents

Info

Publication number: NO116204B
Authority: NO; Norway
Prior art keywords: acid; mol; formic acid; ester; hydrogen peroxide
Prior art date: 1965-07-30

Application number

NO164096A

Other languages

English (en)

Norwegian (no)

Inventor

G Melchior

Original Assignee

Cft Comp Fse Television

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.)

1965-07-30

Filing date

1966-07-28

Publication date

1969-02-17

1965-07-30 Priority claimed from FR26707A external-priority patent/FR1458292A/fr

1965-11-29 Priority claimed from FR40059A external-priority patent/FR1465533A/fr

1966-07-28 Application filed by Cft Comp Fse Television filed Critical Cft Comp Fse Television

1969-02-17 Publication of NO116204B publication Critical patent/NO116204B/no

Links

BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 82
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 62
150000002148 esters Chemical class 0.000 claims description 49
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 41
235000019253 formic acid Nutrition 0.000 claims description 41
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 23
238000000034 method Methods 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 16
150000007513 acids Chemical class 0.000 claims description 12
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 11
239000007864 aqueous solution Substances 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 3
150000002484 inorganic compounds Chemical class 0.000 claims 1
229910010272 inorganic material Inorganic materials 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
238000006735 epoxidation reaction Methods 0.000 description 26
239000000203 mixture Substances 0.000 description 19
239000000243 solution Substances 0.000 description 18
230000002378 acidificating effect Effects 0.000 description 17
150000002978 peroxides Chemical class 0.000 description 15
-1 fatty acid esters Chemical class 0.000 description 14
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000126 substance Substances 0.000 description 12
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 11
229910052740 iodine Inorganic materials 0.000 description 11
239000011630 iodine Substances 0.000 description 11
235000011007 phosphoric acid Nutrition 0.000 description 11
CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 8
235000021313 oleic acid Nutrition 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 5
239000000194 fatty acid Substances 0.000 description 5
229930195729 fatty acid Natural products 0.000 description 5
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
235000020661 alpha-linolenic acid Nutrition 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
229960004488 linolenic acid Drugs 0.000 description 4
KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
235000015112 vegetable and seed oil Nutrition 0.000 description 4
239000008158 vegetable oil Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000001195 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
239000005642 Oleic acid Substances 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
125000005456 glyceride group Chemical group 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
235000020778 linoleic acid Nutrition 0.000 description 3
150000002895 organic esters Chemical class 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
PSAAPHZQPIWZFX-HDXUUTQWSA-N 2-ethylhexyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(CC)CCCC PSAAPHZQPIWZFX-HDXUUTQWSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
OXPCWUWUWIWSGI-MSUUIHNZSA-N Lauryl oleate Chemical compound CCCCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC OXPCWUWUWIWSGI-MSUUIHNZSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
235000012343 cottonseed oil Nutrition 0.000 description 2
239000002385 cottonseed oil Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
125000003700 epoxy group Chemical group 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
239000000944 linseed oil Substances 0.000 description 2
235000021388 linseed oil Nutrition 0.000 description 2
239000007788 liquid Substances 0.000 description 2
WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 2
150000002889 oleic acids Chemical class 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
150000002924 oxiranes Chemical group 0.000 description 2
239000012071 phase Substances 0.000 description 2
229920001515 polyalkylene glycol Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000003813 safflower oil Substances 0.000 description 2
239000003549 soybean oil Substances 0.000 description 2
235000012424 soybean oil Nutrition 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
235000004347 Perilla Nutrition 0.000 description 1
244000124853 Perilla frutescens Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
235000019485 Safflower oil Nutrition 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
235000019486 Sunflower oil Nutrition 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
235000019498 Walnut oil Nutrition 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
YDTIDQXHYVFIKB-HZJYTTRNSA-N benzyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC1=CC=CC=C1 YDTIDQXHYVFIKB-HZJYTTRNSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000011161 development Methods 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical class CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
150000002238 fumaric acids Chemical class 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010410 layer Substances 0.000 description 1
229940049918 linoleate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
QTDSLDJPJJBBLE-PFONDFGASA-N octyl (z)-octadec-9-enoate Chemical compound CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC QTDSLDJPJJBBLE-PFONDFGASA-N 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000002913 oxalic acids Chemical class 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000010491 poppyseed oil Substances 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
MHZDONKZSXBOGL-UHFFFAOYSA-N propyl dihydrogen phosphate Chemical compound CCCOP(O)(O)=O MHZDONKZSXBOGL-UHFFFAOYSA-N 0.000 description 1
235000005713 safflower oil Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical class OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000008170 walnut oil Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N11/00—Colour television systems
- H04N11/06—Transmission systems characterised by the manner in which the individual colour picture signal components are combined
- H04N11/18—Transmission systems characterised by the manner in which the individual colour picture signal components are combined using simultaneous and sequential signals, e.g. SECAM-system
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N9/00—Details of colour television systems
- H04N9/44—Colour synchronisation
- H04N9/47—Colour synchronisation for sequential signals

Landscapes

Engineering & Computer Science (AREA)
Multimedia (AREA)
Signal Processing (AREA)
Color Television Systems (AREA)
Epoxy Compounds (AREA)

NO164096A 1965-07-30 1966-07-28 NO116204B (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR26707A FR1458292A (fr)	1965-07-30	1965-07-30	Perfectionnements au système secam
FR40059A FR1465533A (fr)	1965-11-29	1965-11-29	Perfectionnement aux systèmes de télévision en couleurs

Publications (1)

Publication Number	Publication Date
NO116204B true NO116204B (fr)	1969-02-17

Family

ID=26165141

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO164096A NO116204B (fr)	1965-07-30	1966-07-28

Country Status (11)

Country	Link
AT (1)	AT261018B (fr)
BE (1)	BE684847A (fr)
CH (1)	CH449700A (fr)
DE (2)	DE1462484C3 (fr)
DK (1)	DK118784B (fr)
FI (1)	FI41753C (fr)
GB (1)	GB1099739A (fr)
LU (1)	LU51643A1 (fr)
NL (1)	NL151603B (fr)
NO (1)	NO116204B (fr)
OA (1)	OA02248A (fr)

1966
- 1966-07-26 LU LU51643A patent/LU51643A1/xx unknown
- 1966-07-26 OA OA52546A patent/OA02248A/fr unknown
- 1966-07-27 DK DK389866AA patent/DK118784B/da unknown
- 1966-07-28 NO NO164096A patent/NO116204B/no unknown
- 1966-07-28 GB GB34050/66A patent/GB1099739A/en not_active Expired
- 1966-07-28 CH CH1091066A patent/CH449700A/fr unknown
- 1966-07-29 DE DE1462484A patent/DE1462484C3/de not_active Expired
- 1966-07-29 FI FI662015A patent/FI41753C/fi active
- 1966-07-29 BE BE684847D patent/BE684847A/xx not_active IP Right Cessation
- 1966-07-29 NL NL666610768A patent/NL151603B/xx not_active IP Right Cessation
- 1966-07-29 DE DE1966C0039752 patent/DE1462484A1/de active Granted
- 1966-08-01 AT AT735966A patent/AT261018B/de active

Also Published As

Publication number	Publication date
FI41753B (fr)	1969-10-31
DK118784B (da)	1970-10-05
GB1099739A (en)	1968-01-17
NL6610768A (fr)	1967-01-31
FI41753C (fi)	1970-02-10
CH449700A (fr)	1968-01-15
DE1462484C3 (de)	1975-11-06
LU51643A1 (fr)	1966-09-26
OA02248A (fr)	1970-05-05
BE684847A (fr)	1967-01-30
NL151603B (nl)	1976-11-15
DE1462484B2 (de)	1975-03-27
DE1462484A1 (de)	1968-12-19
AT261018B (de)	1968-04-10

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