CZ297436B6 - Rozvetvená primární alkoholová kompozice, zpusob její prípravy, rozvetvený primární alkylsulfat a alkylkarboxylat, jakoz i detergencní prostredek - Google Patents
Rozvetvená primární alkoholová kompozice, zpusob její prípravy, rozvetvený primární alkylsulfat a alkylkarboxylat, jakoz i detergencní prostredek Download PDFInfo
- Publication number
- CZ297436B6 CZ297436B6 CZ0184899A CZ184899A CZ297436B6 CZ 297436 B6 CZ297436 B6 CZ 297436B6 CZ 0184899 A CZ0184899 A CZ 0184899A CZ 184899 A CZ184899 A CZ 184899A CZ 297436 B6 CZ297436 B6 CZ 297436B6
- Authority
- CZ
- Czechia
- Prior art keywords
- branched
- primary alcohol
- olefin
- branches
- branched primary
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 188
- 238000000034 method Methods 0.000 title claims abstract description 103
- 150000003138 primary alcohols Chemical class 0.000 title claims abstract description 92
- 230000008569 process Effects 0.000 title claims abstract description 54
- 239000003599 detergent Substances 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 150000008051 alkyl sulfates Chemical class 0.000 title claims abstract description 12
- 125000005599 alkyl carboxylate group Chemical group 0.000 title claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 104
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 67
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 22
- 125000004429 atom Chemical group 0.000 claims abstract description 13
- 150000001336 alkenes Chemical class 0.000 claims description 207
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 129
- 239000003054 catalyst Substances 0.000 claims description 97
- -1 nickel carboxylate Chemical class 0.000 claims description 72
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 60
- 150000001298 alcohols Chemical class 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 239000010457 zeolite Substances 0.000 claims description 40
- 229910052759 nickel Inorganic materials 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 238000006317 isomerization reaction Methods 0.000 claims description 31
- 238000006471 dimerization reaction Methods 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 28
- 239000004094 surface-active agent Substances 0.000 claims description 26
- 229910021536 Zeolite Inorganic materials 0.000 claims description 23
- 238000007037 hydroformylation reaction Methods 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 claims description 13
- 229910001657 ferrierite group Inorganic materials 0.000 claims description 13
- 230000003647 oxidation Effects 0.000 claims description 13
- 238000007254 oxidation reaction Methods 0.000 claims description 13
- 150000007513 acids Chemical class 0.000 claims description 12
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000007844 bleaching agent Substances 0.000 claims description 9
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000013522 chelant Substances 0.000 claims description 6
- 239000002808 molecular sieve Substances 0.000 claims description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- 239000012190 activator Substances 0.000 claims description 5
- 239000000344 soap Substances 0.000 claims description 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 5
- 239000003752 hydrotrope Substances 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 230000001180 sulfating effect Effects 0.000 claims description 4
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 230000000447 dimerizing effect Effects 0.000 claims description 3
- 229920005646 polycarboxylate Polymers 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical group 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 2
- 238000004851 dishwashing Methods 0.000 claims description 2
- 230000003165 hydrotropic effect Effects 0.000 claims description 2
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical class OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- 238000009991 scouring Methods 0.000 claims description 2
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- 150000004760 silicates Chemical class 0.000 claims description 2
- 150000003890 succinate salts Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 35
- 238000005481 NMR spectroscopy Methods 0.000 description 30
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 23
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 150000001721 carbon Chemical group 0.000 description 19
- 229910052751 metal Inorganic materials 0.000 description 17
- 239000002184 metal Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 238000004821 distillation Methods 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 229910000033 sodium borohydride Inorganic materials 0.000 description 12
- 239000012279 sodium borohydride Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 11
- 238000004140 cleaning Methods 0.000 description 11
- 239000000571 coke Substances 0.000 description 10
- 239000003446 ligand Substances 0.000 description 10
- 238000005670 sulfation reaction Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 238000006384 oligomerization reaction Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 230000019635 sulfation Effects 0.000 description 9
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 235000015165 citric acid Nutrition 0.000 description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 230000036961 partial effect Effects 0.000 description 8
- 239000004711 α-olefin Substances 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
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- 150000002739 metals Chemical class 0.000 description 6
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
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- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 5
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
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- 125000000129 anionic group Chemical group 0.000 description 4
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- 230000003197 catalytic effect Effects 0.000 description 4
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- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 4
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- WJIBZZVTNMAURL-UHFFFAOYSA-N phosphane;rhodium Chemical compound P.[Rh] WJIBZZVTNMAURL-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FRPJTGXMTIIFIT-UHFFFAOYSA-N tetraacetylethylenediamine Chemical compound CC(=O)C(N)(C(C)=O)C(N)(C(C)=O)C(C)=O FRPJTGXMTIIFIT-UHFFFAOYSA-N 0.000 description 1
- DZOAKHKNLDCJQU-UHFFFAOYSA-N tetradecanoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCCCCCCCCCCCCC(O)=O DZOAKHKNLDCJQU-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical class [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
- C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
- C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
- C07C305/06—Hydrogenosulfates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/755,827 US5780694A (en) | 1996-11-26 | 1996-11-26 | Dimerized alcohol compositions and biodegradible surfactants made therefrom having cold water detergency |
| US08/755,843 US5849960A (en) | 1996-11-26 | 1996-11-26 | Highly branched primary alcohol compositions, and biodegradable detergents made therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ184899A3 CZ184899A3 (cs) | 1999-11-17 |
| CZ297436B6 true CZ297436B6 (cs) | 2006-12-13 |
Family
ID=27116135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ0184899A CZ297436B6 (cs) | 1996-11-26 | 1997-11-25 | Rozvetvená primární alkoholová kompozice, zpusob její prípravy, rozvetvený primární alkylsulfat a alkylkarboxylat, jakoz i detergencní prostredek |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0958267B1 (https=) |
| JP (1) | JP4118960B2 (https=) |
| KR (1) | KR100641537B1 (https=) |
| CN (1) | CN1090599C (https=) |
| AU (1) | AU725968B2 (https=) |
| BG (1) | BG64047B1 (https=) |
| BR (1) | BR9713144B1 (https=) |
| CA (1) | CA2271200C (https=) |
| CZ (1) | CZ297436B6 (https=) |
| DE (1) | DE69728429T2 (https=) |
| ES (1) | ES2214650T3 (https=) |
| NZ (1) | NZ334834A (https=) |
| PL (1) | PL197319B1 (https=) |
| PT (1) | PT958267E (https=) |
| RO (1) | RO120404B1 (https=) |
| RU (1) | RU2198159C2 (https=) |
| SK (1) | SK285235B6 (https=) |
| TR (1) | TR199901169T2 (https=) |
| WO (1) | WO1998023566A1 (https=) |
Families Citing this family (93)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA24137A1 (fr) | 1996-04-16 | 1997-12-31 | Procter & Gamble | Fabrication d'agents de surface ramifies . |
| EG22088A (en) * | 1996-04-16 | 2002-07-31 | Procter & Gamble | Alkoxylated sulfates |
| EG21174A (en) * | 1996-04-16 | 2000-12-31 | Procter & Gamble | Surfactant manufacture |
| WO1997039089A1 (en) * | 1996-04-16 | 1997-10-23 | The Procter & Gamble Company | Liquid cleaning compositions containing selected mid-chain branched surfactants |
| PH11997056158B1 (en) * | 1996-04-16 | 2001-10-15 | Procter & Gamble | Mid-chain branched primary alkyl sulphates as surfactants |
| US6093856A (en) * | 1996-11-26 | 2000-07-25 | The Procter & Gamble Company | Polyoxyalkylene surfactants |
| ZA989155B (en) | 1997-10-10 | 1999-04-12 | Procter & Gamble | Mixed surfactant system |
| JP2001519376A (ja) | 1997-10-14 | 2001-10-23 | ザ、プロクター、エンド、ギャンブル、カンパニー | 中間鎖分岐界面活性剤を含んでなるパーソナルクレンジング組成物 |
| WO1999019435A1 (en) | 1997-10-14 | 1999-04-22 | The Procter & Gamble Company | Granular detergent compositions comprising mid-chain branched surfactants |
| CN1281500A (zh) | 1997-10-14 | 2001-01-24 | 普罗格特-甘布尔公司 | 含有中链支链表面活性剂的轻垢液体或凝胶餐具洗涤剂组合物 |
| DE19859911A1 (de) * | 1998-12-23 | 2000-06-29 | Basf Ag | Verfahren zur Herstellung von Tensidalkoholen und Tensidalkoholethern, die hergestellten Produkte und ihre Verwendung |
| DE19910370A1 (de) | 1999-03-09 | 2000-09-14 | Basf Ag | Verfahren zur Herstellung von Tensidalkoholen und Tensidalkoholethern, die hergestellten Produkte und ihre Verwendung |
| DE19912418A1 (de) | 1999-03-19 | 2000-09-21 | Basf Ag | Verfahren zur Herstellung von Tensidalkoholen und Tensidalkoholethern, die hergestellten Produkte und ihre Verwendung |
| US7202205B1 (en) | 1999-09-01 | 2007-04-10 | Daniel Stedman Connor | Processes for making surfactants via adsorptive separation and products thereof |
| DE19955593A1 (de) | 1999-11-18 | 2001-05-23 | Basf Ag | C13-Alkoholgemisch und funktionalisiertes C13-Alkoholgemisch |
| US7102038B2 (en) * | 2000-05-08 | 2006-09-05 | Shell Oil Company | Phosphorous removal and diene removal, when using diene sensitive catalyst, during conversion of olefins to branched primary alcohols |
| KR100802783B1 (ko) * | 2000-06-26 | 2008-02-12 | 바스프 악티엔게젤샤프트 | 13 및 15개의 탄소 원자를 가진 알코올 혼합물 및 표면활성 물질의 제조에 있어서의 그의 용도 |
| US6706931B2 (en) * | 2000-12-21 | 2004-03-16 | Shell Oil Company | Branched primary alcohol compositions and derivatives thereof |
| US6765106B2 (en) * | 2001-02-15 | 2004-07-20 | Shell Oil Company | Process for preparing a branched olefin, a method of using the branched olefin for making a surfactant, and a surfactant |
| EP1241112A3 (en) | 2001-03-15 | 2003-02-26 | The Procter & Gamble Company | Flexible multiple compartment pouch |
| EP1501775B9 (de) | 2002-04-26 | 2012-09-26 | Basf Se | Alkoxylatgemische und diese enthaltende waschmittel |
| RU2250892C2 (ru) * | 2003-05-16 | 2005-04-27 | ГУ Институт нефтехимии и катализа Академии наук Республики Башкортостан и УНЦ РАН | Способ получения 1,3,4-триалкилциклопентан-1-олов |
| RU2247705C2 (ru) * | 2003-05-19 | 2005-03-10 | ГУ Институт нефтехимии и катализа Академии наук Республики Башкортостан и УНЦ РАН | Способ получения транс-3,4-диалкилциклопентан-1-олов |
| CN100545143C (zh) | 2003-08-28 | 2009-09-30 | 国际壳牌研究有限公司 | 支链酯组合物 |
| MY139122A (en) * | 2003-10-15 | 2009-08-28 | Shell Int Research | Preparation of branched aliphatic alcohols using a process stream from a dehydrogenation-isomerization unit |
| WO2005037416A2 (en) * | 2003-10-15 | 2005-04-28 | Shell Internationale Research Maatschappij B.V. | Preparation of branched aliphatic alcohols using combined process streams from a hydrogenation unit, a dehydrogenation unit, a dimerization unit and an isomerization unit |
| WO2005037753A1 (en) * | 2003-10-15 | 2005-04-28 | Shell Internationale Research Maatschappij B.V., | Preparation of branched aliphatic alcohols using combined process streams from a hydrogenation unit and a dehydrogenation-isomerization unit |
| WO2005037748A2 (en) * | 2003-10-15 | 2005-04-28 | Shell Internationale Research Maatshappij B.V. | Preparation of branched aliphatic alcohols using combined process streams from a dimerization unit and an isomerization unit |
| MY140652A (en) * | 2003-10-15 | 2010-01-15 | Shell Int Research | Preparation of branched aliphatic alcohols using a process stream from an isomerization unit with recycle to a dehydrogenation unit |
| US7335802B2 (en) | 2003-10-15 | 2008-02-26 | Shell Oil Company | Methods of preparing branched aliphatic alcohols |
| RU2006134656A (ru) * | 2004-03-02 | 2008-04-10 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (NL) | Композиции для гигиены, содержащие высокоразветвленный первичный спирт |
| US8211949B2 (en) | 2007-09-24 | 2012-07-03 | Dow Global Technologies Llc | Functionalized long-chain olefin mixtures and uses therefor |
| CN102057013B (zh) | 2008-04-10 | 2014-04-09 | 巴斯夫欧洲公司 | 用于三级原油回收的基于支化醇的表面活性剂 |
| TW201031743A (en) | 2008-12-18 | 2010-09-01 | Basf Se | Surfactant mixture comprising branched short-chain and branched long-chain components |
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| US20110166370A1 (en) * | 2010-01-12 | 2011-07-07 | Charles Winston Saunders | Scattered Branched-Chain Fatty Acids And Biological Production Thereof |
| US20140005082A1 (en) * | 2010-12-29 | 2014-01-02 | Julian Richard BARNES | Method and composition for enhanced hydrocarbons recovery from a formation containing a crude oil |
| CN102643725B (zh) * | 2012-04-25 | 2014-03-26 | 中国日用化学工业研究院 | 一种超浓缩液体洗涤剂及其制备技术 |
| SG11201407840XA (en) * | 2012-05-29 | 2014-12-30 | Shell Int Research | A laundry detergent composition and method of making thereof |
| JP6191188B2 (ja) * | 2013-03-26 | 2017-09-06 | 日油株式会社 | 金属加工油用エステル基油 |
| US10196336B2 (en) * | 2013-06-28 | 2019-02-05 | Dow Global Technologies Llc | Process for the preparation of lightly-branched hydrophobes and the corresponding surfactants and applications thereof |
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| TW201605945A (zh) | 2014-07-08 | 2016-02-16 | 巴斯夫歐洲公司 | 包含二羧酸的酯及１，２－環己烷二羧酸的酯之模製化合物 |
| TW201609628A (zh) | 2014-07-08 | 2016-03-16 | 巴斯夫歐洲公司 | 包含脂族二羧酸二酯及對苯二甲酸二烷基酯之塑化劑組成物 |
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| TWI686444B (zh) | 2014-09-04 | 2020-03-01 | 德商巴斯夫歐洲公司 | 包含聚合二羧酸酯的塑化劑組成物 |
| US9493725B2 (en) | 2014-09-08 | 2016-11-15 | The Procter & Gamble Company | Detergent compositions containing a predominantly C15 alkyl branched surfactant |
| US9493726B2 (en) | 2014-09-08 | 2016-11-15 | The Procter & Gamble Company | Detergent compositions containing a predominantly C15 branched alkyl alkoxylated surfactant |
| TW201619119A (zh) | 2014-10-09 | 2016-06-01 | 巴斯夫歐洲公司 | 包含飽和二羧酸之環烷基酯及１，２－環己烷二羧酸酯的塑化劑組成物 |
| TW201619120A (zh) | 2014-10-09 | 2016-06-01 | 巴斯夫歐洲公司 | 包含飽和二羧酸之環烷基酯及對苯二甲酯之塑化劑組成物 |
| EP3250635B1 (de) | 2015-01-30 | 2018-10-24 | Basf Se | Weichmacher-zusammensetzung, die polymere dicarbonsäureester und terephthalsäuredialkylester enthält |
| CA2999998A1 (en) | 2015-09-30 | 2017-04-06 | Basf Se | Plasticizer composition containing polymeric dicarboxylic acid esters and 1,2-cyclohexane dicarboxylic acid esters |
| CA2999936A1 (en) | 2015-09-30 | 2017-04-06 | Basf Se | Plasticizer composition containing polymeric dicarboxylic acid esters and dicarboxylic acid diesters |
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| US9828565B2 (en) | 2015-12-22 | 2017-11-28 | Shell Oil Company | Alcohol composition and derivatives thereof |
| US9828573B2 (en) | 2015-12-22 | 2017-11-28 | Shell Oil Company | Alcohol composition and derivatives thereof |
| US10550242B2 (en) | 2016-01-20 | 2020-02-04 | Basf Se | Plasticiser composition containing aliphatic dicarboxylic acid esters and diesters selected from 1,2-cyclohexane dicarboxylic acid esters and terephthalic acid esters |
| EP3686238A1 (de) | 2016-03-23 | 2020-07-29 | Basf Se | Polymer-zusammensetzung, enthaltend einen cycloalkyl-alkyl-dicarbonsäurediester als weichmacher |
| EP3266859A1 (en) | 2016-07-05 | 2018-01-10 | Basf Se | Composition suitable as degreasing agent for removing greasy and/or oil type deposits |
| EP3266858A1 (en) | 2016-07-05 | 2018-01-10 | Basf Se | Anti-greying agent |
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| WO2018024597A1 (de) | 2016-08-01 | 2018-02-08 | Basf Se | Weichmacher-zusammensetzung |
| WO2018024594A1 (de) | 2016-08-01 | 2018-02-08 | Basf Se | Weichmacher-zusammensetzung |
| EP3498811B1 (en) | 2016-08-09 | 2025-02-12 | Kao Corporation | Surfactant composition |
| WO2019185409A1 (de) | 2018-03-29 | 2019-10-03 | Basf Se | Pvc-zusammensetzung, enthaltend wenigstens einen weichmacher der wenigstens eine carbonsäureestergruppe aufweist und wenigstens eine carbodiimidverbindung |
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| WO2020256852A1 (en) | 2019-06-20 | 2020-12-24 | Exxonmobil Chemical Patents Inc. | Amphiphilic reaction products from lightly branched olefins and methods for production thereof |
| CN110452369B (zh) * | 2019-07-04 | 2022-10-28 | 联泓(江苏)新材料研究院有限公司 | 一种除油乳化性能优异的异构醇嵌段聚醚及其制备方法和应用 |
| CN112522324A (zh) * | 2019-09-18 | 2021-03-19 | 重庆工商大学 | 一种用加酶洗衣粉催化烯烃环氧化的方法 |
| CN113731483B (zh) * | 2020-05-29 | 2023-10-13 | 中国石油化工股份有限公司 | 一种改性氧化催化材料及其制备方法和应用 |
| CN115551977A (zh) * | 2020-05-29 | 2022-12-30 | 陶氏环球技术有限责任公司 | 具有混合的c13-c14醇的组合物及表面活性剂 |
| EP4161696A4 (en) * | 2020-06-05 | 2025-05-28 | Scion Holdings LLC | BRANCHED ALCOHOLS |
| WO2021247516A1 (en) | 2020-06-05 | 2021-12-09 | SCION Holdings LLC | Branched alcohols |
| MX2022013878A (es) | 2020-06-05 | 2022-11-30 | Procter & Gamble | Composiciones detergentes que contienen un surfactante ramificado. |
| US12221404B2 (en) | 2020-06-05 | 2025-02-11 | SCION Holdings LLC | Composition comprising branched aldehydes |
| US11680032B2 (en) | 2020-06-05 | 2023-06-20 | SCION Holdings LLC | Alcohols production |
| WO2022089867A1 (en) * | 2020-10-08 | 2022-05-05 | Exxonmobil Chemical Patents Inc. | Selective lightly branched alcohols through hydroformylation of isomerized linear olefin feeds |
| US12145904B2 (en) | 2020-12-17 | 2024-11-19 | SCION Holdings LLC | Branched products |
| US20220401331A1 (en) | 2021-06-16 | 2022-12-22 | The Procter & Gamble Company | Personal cleansing compositions, methods and uses |
| CN118201587A (zh) | 2021-11-04 | 2024-06-14 | 科蒂公司 | 不含乙醇的芳香剂底座 |
| US12312563B2 (en) | 2021-12-03 | 2025-05-27 | The Procter & Gamble Company | Liquid detergent compositions |
| US20230174896A1 (en) * | 2021-12-03 | 2023-06-08 | The Procter & Gamble Company | Liquid detergent compositions |
| EP4638411A1 (de) | 2022-12-21 | 2025-10-29 | Basf Se | Weichmacher |
| WO2024133358A1 (de) | 2022-12-21 | 2024-06-27 | Basf Se | Weichmacher-verbindung |
| WO2024153687A1 (de) | 2023-01-19 | 2024-07-25 | Basf Se | Verfahren zur herstellung von 1,2-cyclohexandicarbonsäuredialkylestern |
| NL2035477B1 (en) | 2023-02-20 | 2024-09-03 | Coty Inc | Eye cream formulation |
| FR3146280A1 (fr) | 2023-03-03 | 2024-09-06 | Coty Inc. | Formulations cosmétiques et leurs utilisations |
| NL2034750B1 (en) | 2023-05-02 | 2024-11-14 | Coty Inc | Ethanol-free fragrance chassis |
| DE112024002592A5 (de) | 2023-06-15 | 2026-04-09 | Basf Se | Weichmacher-Zusammensetzung |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1151630A (fr) * | 1955-06-15 | 1958-02-03 | Ici Ltd | Nouveaux alcools saturés et leur procédé de fabrication |
| GB798541A (en) | 1955-06-15 | 1958-07-23 | Ici Ltd | New primary alcohols |
| US4426542A (en) * | 1981-04-22 | 1984-01-17 | Monsanto Company | Synthesis of plasticizer and detergent alcohols |
| US4598162A (en) | 1981-06-11 | 1986-07-01 | Monsanto Company | Detergent range aldehyde and alcohol mixtures and derivatives, and process therefor |
| GB8420945D0 (en) * | 1984-08-17 | 1984-09-19 | Unilever Plc | Detergents compositions |
| EP0313559B1 (en) * | 1986-07-01 | 1991-08-28 | DAVY McKEE (LONDON) LIMITED | Process for the production of aldehydes by hydroformylation |
| US5072057A (en) | 1986-10-03 | 1991-12-10 | Exxon Research & Engineering Co. | Process for the hydroformylation of sulfur-containing thermally cracked petroleum residue and novel products thereof |
| GB8702654D0 (en) * | 1987-02-06 | 1987-03-11 | Davy Mckee Ltd | Process |
| US5196624A (en) * | 1990-04-27 | 1993-03-23 | Chevron Research And Technology Company | Detergent grade to C10 to C28 olefins, (C10 to C28 alkyl)benzenes and C10 to C28 alkyl) benzene sulfonates and process for preparing same using a phosphine containing catalyst |
| US5196625A (en) * | 1990-04-27 | 1993-03-23 | Chevron Research & Technology Company | Detergent grade to C10 to C28 olefins, (C10 to C28 alkyl) benzenes and (C10 to C28 alkyl) benzene sulfonates and process for preparing same using a phosphite containing catalyst |
| US5510306A (en) * | 1993-12-29 | 1996-04-23 | Shell Oil Company | Process for isomerizing linear olefins to isoolefins |
-
1997
- 1997-11-25 AU AU56569/98A patent/AU725968B2/en not_active Ceased
- 1997-11-25 JP JP52430198A patent/JP4118960B2/ja not_active Expired - Lifetime
- 1997-11-25 NZ NZ334834A patent/NZ334834A/xx unknown
- 1997-11-25 PL PL333503A patent/PL197319B1/pl not_active IP Right Cessation
- 1997-11-25 CN CN97199966A patent/CN1090599C/zh not_active Expired - Lifetime
- 1997-11-25 PT PT97952830T patent/PT958267E/pt unknown
- 1997-11-25 RU RU99113994/04A patent/RU2198159C2/ru active
- 1997-11-25 CZ CZ0184899A patent/CZ297436B6/cs not_active IP Right Cessation
- 1997-11-25 BR BRPI9713144-0A patent/BR9713144B1/pt not_active IP Right Cessation
- 1997-11-25 ES ES97952830T patent/ES2214650T3/es not_active Expired - Lifetime
- 1997-11-25 EP EP97952830A patent/EP0958267B1/en not_active Revoked
- 1997-11-25 DE DE69728429T patent/DE69728429T2/de not_active Revoked
- 1997-11-25 RO RO99-00592A patent/RO120404B1/ro unknown
- 1997-11-25 CA CA002271200A patent/CA2271200C/en not_active Expired - Lifetime
- 1997-11-25 TR TR1999/01169T patent/TR199901169T2/xx unknown
- 1997-11-25 KR KR1019997004593A patent/KR100641537B1/ko not_active Expired - Fee Related
- 1997-11-25 WO PCT/EP1997/006694 patent/WO1998023566A1/en not_active Ceased
- 1997-11-25 SK SK686-99A patent/SK285235B6/sk not_active IP Right Cessation
-
1999
- 1999-05-28 BG BG103445A patent/BG64047B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69728429D1 (de) | 2004-05-06 |
| JP4118960B2 (ja) | 2008-07-16 |
| AU5656998A (en) | 1998-06-22 |
| RU2198159C2 (ru) | 2003-02-10 |
| KR20000069117A (ko) | 2000-11-25 |
| KR100641537B1 (ko) | 2006-10-31 |
| DE69728429T2 (de) | 2005-03-03 |
| SK68699A3 (en) | 1999-11-08 |
| PT958267E (pt) | 2004-08-31 |
| RO120404B1 (ro) | 2006-01-30 |
| ES2214650T3 (es) | 2004-09-16 |
| CN1238749A (zh) | 1999-12-15 |
| CA2271200A1 (en) | 1998-06-04 |
| TR199901169T2 (xx) | 1999-08-23 |
| EP0958267B1 (en) | 2004-03-31 |
| BR9713144B1 (pt) | 2009-01-13 |
| SK285235B6 (sk) | 2006-09-07 |
| BG103445A (en) | 2000-05-31 |
| EP0958267A1 (en) | 1999-11-24 |
| CN1090599C (zh) | 2002-09-11 |
| CZ184899A3 (cs) | 1999-11-17 |
| JP2001506597A (ja) | 2001-05-22 |
| NZ334834A (en) | 2000-07-28 |
| WO1998023566A1 (en) | 1998-06-04 |
| BG64047B1 (bg) | 2003-11-28 |
| CA2271200C (en) | 2009-02-03 |
| PL197319B1 (pl) | 2008-03-31 |
| AU725968B2 (en) | 2000-10-26 |
| BR9713144A (pt) | 2000-02-08 |
| PL333503A1 (en) | 1999-12-20 |
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|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20091125 |