CA1109075A - Procede pour la preparation de 2-acyloxyalcane sulfonates-1, et leur emploi dans des substances pour les soins des dents et de la bouche - Google Patents

Procede pour la preparation de 2-acyloxyalcane sulfonates-1, et leur emploi dans des substances pour les soins des dents et de la bouche

Info

Publication number: CA1109075A
Authority: CA; Canada
Prior art keywords: sodium; sulfonate; mouth; care; acyloxyalkane
Prior art date: 1976-05-05
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA277,670A

Other languages

English (en)

Inventor

Herbert Hartung

Siegfried Billenstein

Jochen M. Quack

Alwin Reng

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-05-05

Filing date

1977-05-04

Publication date

1981-09-15

1976-05-05 Priority claimed from DE19762619750 external-priority patent/DE2619750A1/de

1976-05-05 Priority claimed from DE19762619846 external-priority patent/DE2619846A1/de

1977-05-04 Application filed by Hoechst AG filed Critical Hoechst AG

1981-09-15 Application granted granted Critical

1981-09-15 Publication of CA1109075A publication Critical patent/CA1109075A/fr

Status Expired legal-status Critical Current

Links

239000000126 substance Substances 0.000 title claims description 15
238000004519 manufacturing process Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 claims abstract description 32
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
238000005187 foaming Methods 0.000 claims abstract description 10
239000002253 acid Substances 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract 3
-1 alkaline earth metal salts Chemical class 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
239000011734 sodium Substances 0.000 claims description 12
229910052708 sodium Inorganic materials 0.000 claims description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
150000003871 sulfonates Chemical class 0.000 claims description 9
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
150000003460 sulfonic acids Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims 4
239000003513 alkali Substances 0.000 claims 2
150000007513 acids Chemical class 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 12
235000019640 taste Nutrition 0.000 abstract description 8
238000009472 formulation Methods 0.000 abstract description 6
150000001875 compounds Chemical class 0.000 abstract description 3
239000004088 foaming agent Substances 0.000 abstract description 3
229910001413 alkali metal ion Inorganic materials 0.000 abstract description 2
229910021645 metal ion Inorganic materials 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
DOFRGJITFVGCFN-UHFFFAOYSA-N C(C)(=O)OC(C)CCCCCCCCCCCC.[Na] Chemical compound C(C)(=O)OC(C)CCCCCCCCCCCC.[Na] DOFRGJITFVGCFN-UHFFFAOYSA-N 0.000 description 14
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
235000019441 ethanol Nutrition 0.000 description 11
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
239000001506 calcium phosphate Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 10
229940081974 saccharin Drugs 0.000 description 10
235000019204 saccharin Nutrition 0.000 description 10
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 10
239000000606 toothpaste Substances 0.000 description 10
239000000341 volatile oil Substances 0.000 description 10
235000019739 Dicalciumphosphate Nutrition 0.000 description 9
238000004140 cleaning Methods 0.000 description 9
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 9
229910000390 dicalcium phosphate Inorganic materials 0.000 description 9
229940038472 dicalcium phosphate Drugs 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000004354 Hydroxyethyl cellulose Substances 0.000 description 7
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 7
229910000019 calcium carbonate Inorganic materials 0.000 description 7
229940071826 hydroxyethyl cellulose Drugs 0.000 description 7
239000002904 solvent Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 6
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
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 5
235000011187 glycerol Nutrition 0.000 description 5
239000007788 liquid Substances 0.000 description 5
235000019333 sodium laurylsulphate Nutrition 0.000 description 5
HPNPFXJPJXALQB-UHFFFAOYSA-M sodium;2-acetyloxytetradecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCC(CS([O-])(=O)=O)OC(C)=O HPNPFXJPJXALQB-UHFFFAOYSA-M 0.000 description 5
229940034610 toothpaste Drugs 0.000 description 5
HRDZWVFQOJEFJT-UHFFFAOYSA-N C(CCCCCCCCCCC)C(C)O.[Na] Chemical compound C(CCCCCCCCCCC)C(C)O.[Na] HRDZWVFQOJEFJT-UHFFFAOYSA-N 0.000 description 4
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
239000001768 carboxy methyl cellulose Substances 0.000 description 4
235000012239 silicon dioxide Nutrition 0.000 description 4
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 4
239000004299 sodium benzoate Substances 0.000 description 4
235000010234 sodium benzoate Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000008112 carboxymethyl-cellulose Substances 0.000 description 3
229940105329 carboxymethylcellulose Drugs 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000002537 cosmetic Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000002324 mouth wash Substances 0.000 description 3
125000001421 myristyl 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])[H] 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
238000005498 polishing Methods 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 3
229940082004 sodium laurate Drugs 0.000 description 3
235000010265 sodium sulphite Nutrition 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
WPCBBWIJKAISIT-UHFFFAOYSA-N C(C)(=O)OC(C)CCCCCCCCCC.[Na] Chemical compound C(C)(=O)OC(C)CCCCCCCCCC.[Na] WPCBBWIJKAISIT-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
235000010443 alginic acid Nutrition 0.000 description 2
229920000615 alginic acid Polymers 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
229910021502 aluminium hydroxide Inorganic materials 0.000 description 2
PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 2
229910000323 aluminium silicate Inorganic materials 0.000 description 2
CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000499 gel Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229940051866 mouthwash Drugs 0.000 description 2
235000015205 orange juice Nutrition 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
239000003826 tablet Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
239000008399 tap water Substances 0.000 description 2
235000020679 tap water Nutrition 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
BHHYHSUAOQUXJK-UHFFFAOYSA-L zinc fluoride Chemical compound F[Zn]F BHHYHSUAOQUXJK-UHFFFAOYSA-L 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 1
IOHJQSFEAYDZGF-UHFFFAOYSA-N 2-dodecyloxirane Chemical compound CCCCCCCCCCCCC1CO1 IOHJQSFEAYDZGF-UHFFFAOYSA-N 0.000 description 1
NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
YUBGJSHFULOAKN-UHFFFAOYSA-N 2-hydroxyhexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCC(O)CS(O)(=O)=O YUBGJSHFULOAKN-UHFFFAOYSA-N 0.000 description 1
UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 description 1
XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 description 1
MOMKYJPSVWEWPM-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=CS1 MOMKYJPSVWEWPM-UHFFFAOYSA-N 0.000 description 1
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
102000009027 Albumins Human genes 0.000 description 1
108010088751 Albumins Proteins 0.000 description 1
POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000206575 Chondrus crispus Species 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
HZWXJJCSDBQVLF-UHFFFAOYSA-N acetoxysulfonic acid Chemical compound CC(=O)OS(O)(=O)=O HZWXJJCSDBQVLF-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
229960000458 allantoin Drugs 0.000 description 1
230000004075 alteration Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
229910001634 calcium fluoride Inorganic materials 0.000 description 1
229940043256 calcium pyrophosphate Drugs 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000006735 deficit Effects 0.000 description 1
235000019821 dicalcium diphosphate Nutrition 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000010981 drying operation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
229960004667 ethyl cellulose Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000008233 hard water Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
229940071676 hydroxypropylcellulose Drugs 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
230000007794 irritation Effects 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
235000001055 magnesium Nutrition 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
229910000400 magnesium phosphate tribasic Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
125000000913 palmityl 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])[H] 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 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
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
235000019983 sodium metaphosphate Nutrition 0.000 description 1
229960004711 sodium monofluorophosphate Drugs 0.000 description 1
229960001922 sodium perborate Drugs 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000019832 sodium triphosphate Nutrition 0.000 description 1
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
150000008053 sultones Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
230000009967 tasteless effect Effects 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Oral & Maxillofacial Surgery (AREA)
Epidemiology (AREA)
Birds (AREA)
Cosmetics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA277,670A 1976-05-05 1977-05-04 Procede pour la preparation de 2-acyloxyalcane sulfonates-1, et leur emploi dans des substances pour les soins des dents et de la bouche Expired CA1109075A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DEP2619846.9		1976-05-05
DE19762619750 DE2619750A1 (de)	1976-05-05	1976-05-05	Schaumerzeugende stoffe fuer zahnund mundpflegemittel
DEP2619750.2		1976-05-05
DE19762619846 DE2619846A1 (de)	1976-05-05	1976-05-05	Verfahren zur herstellung reiner 2-acyloxyalkansulfonaten-1

Publications (1)

Publication Number	Publication Date
CA1109075A true CA1109075A (fr)	1981-09-15

Family

ID=25770417

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA277,670A Expired CA1109075A (fr)	1976-05-05	1977-05-04	Procede pour la preparation de 2-acyloxyalcane sulfonates-1, et leur emploi dans des substances pour les soins des dents et de la bouche

Country Status (6)

Country	Link
JP (1)	JPS52133922A (fr)
CA (1)	CA1109075A (fr)
FR (1)	FR2350337A1 (fr)
GB (1)	GB1575923A (fr)
IT (1)	IT1075525B (fr)
NL (1)	NL7704736A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1994009763A1 (fr) *	1992-11-04	1994-05-11	Unilever Plc	Ameliorations concernant des tensio-actifs a base d'isethionate substitue et compositions de soin pour la peau renfermant lesdits tensio-actifs

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE652410C (de) *	1929-11-01	1937-10-30	I G Farbenindustrie Akt Ges	Verfahren zur Herstellung esterartiger aliphatischer Sulfonsaeuren
US2094451A (en) *	1930-05-01	1937-09-28	Ig Farbenindustrie Ag	Production of hydroxy-sulfonic acids
GB544405A (en) *	1939-06-28	1942-04-13	James Howard Cummings	An improved proteolytic dentifrice
DE1076704B (de) *	1957-03-07	1960-03-03	Keystone Chemurgic Corp	Verfahren zur Herstellung von therapeutisch verwendbaren Carbonsaeurederivaten
US3004049A (en) *	1959-12-01	1961-10-10	Gen Aniline & Film Corp	Production of ester type anionic surface active agents
BE650323A (fr) *	1963-07-09
US3686239A (en) *	1968-01-30	1972-08-22	M & T Chemicals Inc	Process for the preparation of sulfohydrocarbon-di-yl neocarboxylates
GB1338966A (en) *	1970-12-14	1973-11-28	Procter & Gamble	Detergent builder compositions

1977
- 1977-04-29 NL NL7704736A patent/NL7704736A/xx not_active Application Discontinuation
- 1977-05-03 IT IT2313577A patent/IT1075525B/it active
- 1977-05-04 CA CA277,670A patent/CA1109075A/fr not_active Expired
- 1977-05-04 JP JP5085877A patent/JPS52133922A/ja active Pending
- 1977-05-05 GB GB1885277A patent/GB1575923A/en not_active Expired
- 1977-05-05 FR FR7713682A patent/FR2350337A1/fr active Pending

Also Published As

Publication number	Publication date
JPS52133922A (en)	1977-11-09
FR2350337A1 (fr)	1977-12-02
NL7704736A (nl)	1977-11-08
GB1575923A (en)	1980-10-01
IT1075525B (it)	1985-04-22

Legal Events

Date	Code	Title	Description
1998-09-15	MKEX	Expiry

Publication	Publication Date	Title
US3531564A (en)	1970-09-29	Fluoride dental preparation
US5756074A (en)	1998-05-26	Compositions based on an abrasive system and on a surfactant system
EP0670827B1 (fr)	1997-04-16	Alkylglyceramides et leur utilisation comme tensioactifs
US4791097A (en)	1988-12-13	Benzoic acid esters and their use
JPS6360725B2 (fr)	1988-11-25
JPS6141502B2 (fr)	1986-09-16
EP0091237B1 (fr)	1986-01-08	Composition détergente
US3887712A (en)	1975-06-03	Oral hygiene products
US3344018A (en)	1967-09-26	Biocidal quaternary ammonium sulfamates
JP2871856B2 (ja)	1999-03-17	マイルドで実質上無色のシャンプー組成物
US3223704A (en)	1965-12-14	Quaternary ammonium sulfamates
CA1109075A (fr)	1981-09-15	Procede pour la preparation de 2-acyloxyalcane sulfonates-1, et leur emploi dans des substances pour les soins des dents et de la bouche
US4111653A (en)	1978-09-05	Alkali stannite depilatories
US4454153A (en)	1984-06-12	Zinc salt of a hydrolyzed tricarboxylic acid from ene-adducts of maleic anhydride to undecylenic acid
US5616782A (en)	1997-04-01	Method of producing alkyl sulfoacetate compositions
JPH04327570A (ja)	1992-11-17	アルキルエーテルカルボン酸タウリド
US6503873B1 (en)	2003-01-07	Ultra mild detergent compositions
JPH0560519B2 (fr)	1993-09-02
US5371251A (en)	1994-12-06	Polyol polyether sulfosuccinates, a process for preparing them, and their use
US2909535A (en)	1959-10-20	Novel higher aliphatic acid derivatives and compositions containing the same
US2842479A (en)	1958-07-08	Nu-higher aliphatic acyl alpha-amino aryl acetic acids and compositions therewith
JPH04503060A (ja)	1992-06-04	界面活性混合物
US3898284A (en)	1975-08-05	Ether-linked quaternary ammonium compounds
JP2855095B2 (ja)	1999-02-10	表面活性剤
JPH04507248A (ja)	1992-12-17	歯垢防止用の口腔および歯の手入れ用製剤