NO781657L - Aluminiumorganiske forbindelser. - Google Patents

Aluminiumorganiske forbindelser.

Info

Publication number: NO781657L
Authority: NO; Norway
Prior art keywords: alkyl; chloro; compound; general formula; compounds
Prior art date: 1977-05-11

Application number

NO78781657A

Other languages

English (en)

Norwegian (no)

Inventor

Horst Pauling

Original Assignee

Hoffmann La Roche

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.)

1977-05-11

Filing date

1978-05-10

Publication date

1978-11-14

1978-05-10 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1978-11-14 Publication of NO781657L publication Critical patent/NO781657L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 40
125000001309 chloro group Chemical group Cl* 0.000 claims description 50
125000000217 alkyl group Chemical group 0.000 claims description 34
125000003118 aryl group Chemical group 0.000 claims description 17
230000001166 anti-perspirative effect Effects 0.000 claims description 15
239000003213 antiperspirant Substances 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
238000000034 method Methods 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 11
125000001589 carboacyl group Chemical group 0.000 claims description 10
125000003435 aroyl group Chemical group 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
150000002902 organometallic compounds Chemical class 0.000 claims description 4
239000002537 cosmetic Substances 0.000 claims description 3
125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
KUVXJBSVPBXHEK-UHFFFAOYSA-N octylaluminum Chemical compound CCCCCCCC[Al] KUVXJBSVPBXHEK-UHFFFAOYSA-N 0.000 claims description 2
208000035985 Body Odor Diseases 0.000 claims 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
206010040904 Skin odour abnormal Diseases 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
229910052796 boron Chemical group 0.000 claims 1
230000035900 sweating Effects 0.000 claims 1
-1 methyl compound Chemical class 0.000 description 58
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 17
238000005259 measurement Methods 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
125000001246 bromo group Chemical group Br* 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 12
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 10
239000007788 liquid Substances 0.000 description 10
239000003921 oil Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000013543 active substance Substances 0.000 description 8
230000000694 effects Effects 0.000 description 7
MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000000443 aerosol Substances 0.000 description 5
229910052782 aluminium Inorganic materials 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000001282 iso-butane Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
210000004243 sweat Anatomy 0.000 description 5
LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
DQLXBOOGAXBQSK-UHFFFAOYSA-M chloro-hexadecoxy-(2-methylpropyl)alumane Chemical compound CCCCCCCCCCCCCCCCO[Al](Cl)CC(C)C DQLXBOOGAXBQSK-UHFFFAOYSA-M 0.000 description 4
238000001816 cooling Methods 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
239000011261 inert gas Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
239000003380 propellant Substances 0.000 description 4
230000005068 transpiration Effects 0.000 description 4
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 3
239000004338 Dichlorodifluoromethane Substances 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
235000019404 dichlorodifluoromethane Nutrition 0.000 description 3
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 3
DZZKHRZZALRSLB-UHFFFAOYSA-N hexylaluminum Chemical compound CCCCCC[Al] DZZKHRZZALRSLB-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
125000004171 alkoxy aryl group Chemical group 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
239000012300 argon atmosphere Substances 0.000 description 2
HLLHUYCAXXETFO-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium hexadecanoate Chemical compound C(CCCCCCCCCCCCCCC)(=O)[O-].C(C(C)C)[Al+]CC(C)C HLLHUYCAXXETFO-UHFFFAOYSA-M 0.000 description 2
HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 2
238000007664 blowing Methods 0.000 description 2
KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229960000541 cetyl alcohol Drugs 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
UTAQEZCRJGIPOJ-UHFFFAOYSA-L chloro-(2-methylpropyl)-phenoxyalumane Chemical compound CC(C)C[Al](Cl)OC1=CC=CC=C1 UTAQEZCRJGIPOJ-UHFFFAOYSA-L 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000004465 cycloalkenyloxy group Chemical group 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000010926 purge Methods 0.000 description 2
239000000523 sample Substances 0.000 description 2
230000028327 secretion Effects 0.000 description 2
239000007921 spray Substances 0.000 description 2
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
229960002703 undecylenic acid Drugs 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
125000005877 1,4-benzodioxanyl group Chemical group 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
PHMNXPYGVPEQSJ-UHFFFAOYSA-N Dimethoxane Chemical compound CC1CC(OC(C)=O)OC(C)O1 PHMNXPYGVPEQSJ-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000005082 alkoxyalkenyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000005418 aryl aryl group Chemical group 0.000 description 1
125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
RFMALBGUPRCCMO-UHFFFAOYSA-M chloro-(2-ethylhexoxy)-(2-methylpropyl)alumane Chemical compound CCCCC(CC)CO[Al](Cl)CC(C)C RFMALBGUPRCCMO-UHFFFAOYSA-M 0.000 description 1
OSKMHCKXPHKVMK-UHFFFAOYSA-M chloro-(2-methylpropyl)-octadecoxyalumane Chemical compound CCCCCCCCCCCCCCCCCCO[Al](Cl)CC(C)C OSKMHCKXPHKVMK-UHFFFAOYSA-M 0.000 description 1
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000000490 cosmetic additive Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000004858 cycloalkoxyalkyl group Chemical group 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000002781 deodorant agent Substances 0.000 description 1
230000001877 deodorizing effect Effects 0.000 description 1
PZWDHVKNXVLHOV-UHFFFAOYSA-K di(hexadecanoyloxy)alumanyl hexadecanoate Chemical compound [Al+3].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O PZWDHVKNXVLHOV-UHFFFAOYSA-K 0.000 description 1
JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
QTTIHZJQJYQHNW-UHFFFAOYSA-L hexadecanoate 2-methylpropylaluminum(2+) Chemical compound C(CCCCCCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCCCCCC)(=O)[O-].C(C(C)C)[Al+2] QTTIHZJQJYQHNW-UHFFFAOYSA-L 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005644 linolenyl group Chemical group 0.000 description 1
230000007774 longterm Effects 0.000 description 1
125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
239000000463 material Substances 0.000 description 1
229940041616 menthol Drugs 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 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
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
239000013642 negative control Substances 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005441 o-toluyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
229940101267 panthenol Drugs 0.000 description 1
235000020957 pantothenol Nutrition 0.000 description 1
239000011619 pantothenol Substances 0.000 description 1
239000002304 perfume Substances 0.000 description 1
125000005561 phenanthryl group Chemical group 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000001444 retinoyl group Chemical group O=C([*])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000946 retinyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C([H])=C(C([H])([H])[H])/C([H])=C([H])/C1=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C1(C([H])([H])[H])C([H])([H])[H] 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
230000035945 sensitivity Effects 0.000 description 1
230000037394 skin elasticity Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
125000001424 substituent group Chemical group 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
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
239000011345 viscous material Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- 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
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
- C07F5/067—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage) compounds with Al also linked to H or halogen

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Anesthesiology (AREA)
Toxicology (AREA)
Birds (AREA)
Epidemiology (AREA)
Cosmetics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)

NO78781657A 1977-05-11 1978-05-10 Aluminiumorganiske forbindelser. NO781657L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LU77315A LU77315A1 (de)	1977-05-11	1977-05-11	Verfahren zur herstellung von aluminiumorganischen verbindungen

Publications (1)

Publication Number	Publication Date
NO781657L true NO781657L (no)	1978-11-14

Family

ID=19728571

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO78781657A NO781657L (no)	1977-05-11	1978-05-10	Aluminiumorganiske forbindelser.

Country Status (18)

Country	Link
JP (1)	JPS53141220A (de)
AR (1)	AR218062A1 (de)
AT (1)	AT362517B (de)
AU (1)	AU519030B2 (de)
BE (1)	BE866890A (de)
BR (1)	BR7802942A (de)
DE (1)	DE2820657A1 (de)
DK (1)	DK206678A (de)
ES (1)	ES469659A1 (de)
FR (1)	FR2390449A1 (de)
GB (1)	GB1596599A (de)
IT (1)	IT1094812B (de)
LU (1)	LU77315A1 (de)
NL (1)	NL7804659A (de)
NO (1)	NO781657L (de)
PT (1)	PT68023B (de)
SE (1)	SE7805359L (de)
ZA (1)	ZA782546B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA816685B (en) *	1980-10-03	1982-09-29	Hoffmann La Roche	Aluminium compounds containing organic radicals
DE69830486T2 (de) *	1997-05-01	2006-03-16	Kao Corp.	Aluminiumverbindungen und deren verwendung

1977
- 1977-05-11 LU LU77315A patent/LU77315A1/de unknown
1978
- 1978-04-26 AR AR271916A patent/AR218062A1/es active
- 1978-04-28 NL NL7804659A patent/NL7804659A/xx not_active Application Discontinuation
- 1978-05-03 ZA ZA00782546A patent/ZA782546B/xx unknown
- 1978-05-09 FR FR7813657A patent/FR2390449A1/fr not_active Withdrawn
- 1978-05-09 JP JP5415478A patent/JPS53141220A/ja active Pending
- 1978-05-10 PT PT68023A patent/PT68023B/pt unknown
- 1978-05-10 BR BR7802942A patent/BR7802942A/pt unknown
- 1978-05-10 IT IT23212/78A patent/IT1094812B/it active
- 1978-05-10 NO NO78781657A patent/NO781657L/no unknown
- 1978-05-10 AT AT338378A patent/AT362517B/de not_active IP Right Cessation
- 1978-05-10 ES ES469659A patent/ES469659A1/es not_active Expired
- 1978-05-10 SE SE7805359A patent/SE7805359L/xx unknown
- 1978-05-10 BE BE187539A patent/BE866890A/xx unknown
- 1978-05-10 DK DK206678A patent/DK206678A/da not_active Application Discontinuation
- 1978-05-10 GB GB18673/78A patent/GB1596599A/en not_active Expired
- 1978-05-11 AU AU36006/78A patent/AU519030B2/en not_active Expired
- 1978-05-11 DE DE19782820657 patent/DE2820657A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
GB1596599A (en)	1981-08-26
PT68023B (en)	1980-05-07
DK206678A (da)	1978-11-12
FR2390449A1 (fr)	1978-12-08
AT362517B (de)	1981-05-25
ATA338378A (de)	1980-10-15
BR7802942A (pt)	1978-12-19
ZA782546B (en)	1979-06-27
PT68023A (en)	1978-06-01
AU519030B2 (en)	1981-11-05
DE2820657A1 (de)	1978-11-23
IT7823212A0 (it)	1978-05-10
AU3600678A (en)	1979-11-15
BE866890A (fr)	1978-11-10
ES469659A1 (es)	1979-09-16
SE7805359L (sv)	1978-11-12
AR218062A1 (es)	1980-05-15
LU77315A1 (de)	1979-03-26
IT1094812B (it)	1985-08-10
NL7804659A (nl)	1978-11-14
JPS53141220A (en)	1978-12-08

Publication	Publication Date	Title
Brown et al.	1980	Hydroboration. 55. Hydroboration of alkynes with dibromoborane-dimethyl sulfide. Convenient preparation of alkenyldibromoboranes
Evans et al.	1979	Phosphonamide stabilized allylic carbanions. New homoenolate anion equivalents
Eisch et al.	1971	Organometallic compounds of Group III. XIX. Regiospecificity and stereochemistry in the hydralumination of unsymmetrical acetylenes. Controlled cis or trans reduction of 1-alkynyl derivatives
US4822602A (en)	1989-04-18	Cosmetic sticks
Bertini et al.	1970	Geminal dimetallic compounds: Reactivity of methylene magnesium halides and related compounds. A general carbonyl olefination reaction
Brown et al.	1979	Hydroboration. 51. Hydroboration of representative allenes with 9-borabicyclo [3.3. 1] nonane. An exceptional directive effect providing a direct synthesis of B-allyl-9-borabicyclo [3.3. 1] nonane derivatives
US5175321A (en)	1992-12-29	Amide derivatives and dermatologic preparations containing the same
EP0482860A1 (de)	1992-04-29	Kosmetische Zusammensetzung
JP2003533457A (ja)	2003-11-11	高い有効性、低い残留性の制汗剤棒状組成物
US4055634A (en)	1977-10-25	Antiperspirants
Braverman et al.	1974	The [2, 3]-sigmatropic rearrangement of propargyl benzenesulphinates to allenyl phenyl sulphones
Noble et al.	1978	Scalp carriage of Pityrosporum species: the effect of physiological maturity, sex and race
Bell et al.	1965	Kinetic hydrogen isotope effects in the ionization of some ketonic substances
NO781657L (no)	1978-11-14	Aluminiumorganiske forbindelser.
US6231842B1 (en)	2001-05-15	Antiperspirant and deodorant sticks containing triglyceride gellants having improved product hardness and low residue performance
US6258346B1 (en)	2001-07-10	Cosmetic sticks containing triglyceride gellants having improved product hardness and low residue performance
AU603606B2 (en)	1990-11-22	Light-screen agent
JPH07118119A (ja)	1995-05-09	化粧料及び口腔剤
Suzuki et al.	2004	7Li-and 31P NMR spectra of cyclopentanone lithium enolate in ethereal solvents: identification of the HMPA-coordinated aggregate structures
US2779799A (en)	1957-01-29	1-cyclobutyl-1-ethynyl-ethanol-1
RU2162077C2 (ru)	2001-01-20	ПРИМЕНЕНИЕ β-(ХЛОРЭТИЛ)БУТИЛСУЛЬФИДА В КАЧЕСТВЕ ИМИТАТОРА β,β′-ДИХЛОРДИЭТИЛСУЛЬФИДА
NL194030C (nl)	2001-05-03	Creme of lotion.
JP3156867B2 (ja)	2001-04-16	２−ヒドロキシメチル−シクロアルカノール誘導体
EP0555208A1 (de)	1993-08-18	Metalloximat/polyethylenglykole chemisches dekontaminierungssystem.
JP2883760B2 (ja)	1999-04-19	有害生物忌避剤