CH495959A - Verfahren zur Herstellung von Sonnenlicht filternden Stoffen - Google Patents
Verfahren zur Herstellung von Sonnenlicht filternden StoffenInfo
- Publication number
- CH495959A CH495959A CH1690866A CH1690866A CH495959A CH 495959 A CH495959 A CH 495959A CH 1690866 A CH1690866 A CH 1690866A CH 1690866 A CH1690866 A CH 1690866A CH 495959 A CH495959 A CH 495959A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrazine
- methyl
- sulfobenzaldehyde
- carboxyphenyl
- sulfophenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 8
- 239000000126 substance Substances 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 7
- 159000000000 sodium salts Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 230000000475 sunscreen effect Effects 0.000 claims 1
- 239000000516 sunscreening agent Substances 0.000 claims 1
- -1 bromopropyl Chemical group 0.000 description 94
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 16
- SHHKMWMIKILKQW-UHFFFAOYSA-N 2-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=O SHHKMWMIKILKQW-UHFFFAOYSA-N 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000003287 bathing Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YIKWQSHFMBOYON-UHFFFAOYSA-N 2,4-dichloro-3-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C(C=O)=C1Cl YIKWQSHFMBOYON-UHFFFAOYSA-N 0.000 description 2
- LJRBVVNQJGAQQY-UHFFFAOYSA-N 2-bromo-5-formylbenzenesulfonic acid Chemical compound BrC1=C(C=C(C=O)C=C1)S(=O)(=O)O LJRBVVNQJGAQQY-UHFFFAOYSA-N 0.000 description 2
- JXFUQVJNPIAUTP-UHFFFAOYSA-N 2-chloro-3-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=O)=C1Cl JXFUQVJNPIAUTP-UHFFFAOYSA-N 0.000 description 2
- AKVOYDMLDVWAJO-UHFFFAOYSA-N 2-formyl-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(C=O)=C1 AKVOYDMLDVWAJO-UHFFFAOYSA-N 0.000 description 2
- RFQQTWOZHGEREC-UHFFFAOYSA-N 2-formyl-5-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(C=O)C(S(O)(=O)=O)=C1 RFQQTWOZHGEREC-UHFFFAOYSA-N 0.000 description 2
- UHDNUPHSDMOGCR-UHFFFAOYSA-N 3-Formylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=O)=C1 UHDNUPHSDMOGCR-UHFFFAOYSA-N 0.000 description 2
- QFUQJXPXVPAMLL-UHFFFAOYSA-N 3-cyano-4-formylbenzenesulfonic acid Chemical compound C(#N)C1=C(C=O)C=CC(=C1)S(=O)(=O)O QFUQJXPXVPAMLL-UHFFFAOYSA-N 0.000 description 2
- ARZBLPSPBDDHPF-UHFFFAOYSA-N 3-formyl-4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=C(C=C(C(=O)O)C=C1)C=O ARZBLPSPBDDHPF-UHFFFAOYSA-N 0.000 description 2
- CEQZAURBTQUFBP-UHFFFAOYSA-N 3-formyl-4-prop-1-enylbenzoic acid Chemical compound C(=CC)C1=C(C=C(C(=O)O)C=C1)C=O CEQZAURBTQUFBP-UHFFFAOYSA-N 0.000 description 2
- MRXZEDMLQMDMGB-UHFFFAOYSA-N 3-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=O)=C1 MRXZEDMLQMDMGB-UHFFFAOYSA-N 0.000 description 2
- UJEKWYDFCZEYEH-UHFFFAOYSA-N 4-ethoxycarbonyl-3-formylbenzoic acid Chemical compound C(=O)(OCC)C1=C(C=C(C(=O)O)C=C1)C=O UJEKWYDFCZEYEH-UHFFFAOYSA-N 0.000 description 2
- GDZXRBUCLLKACJ-UHFFFAOYSA-N 4-formyl-2-hydroxybenzenesulfonic acid Chemical compound OC1=CC(C=O)=CC=C1S(O)(=O)=O GDZXRBUCLLKACJ-UHFFFAOYSA-N 0.000 description 2
- OKFPEGQLJXBXFI-UHFFFAOYSA-N 4-formyl-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1C=O OKFPEGQLJXBXFI-UHFFFAOYSA-N 0.000 description 2
- OOOLBFCCHPTUOB-UHFFFAOYSA-N 4-formyl-3-methylsulfonylbenzenesulfonic acid Chemical compound CS(=O)(=O)C1=C(C=O)C=CC(=C1)S(=O)(=O)O OOOLBFCCHPTUOB-UHFFFAOYSA-N 0.000 description 2
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 2
- GXRQQNQCMLEUAW-UHFFFAOYSA-N 5-chloro-2-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(Cl)=CC=C1C=O GXRQQNQCMLEUAW-UHFFFAOYSA-N 0.000 description 2
- IPBVITPZBJFMCA-UHFFFAOYSA-N C(C)N(N)C1=CC(=CC=C1)C(=O)O Chemical compound C(C)N(N)C1=CC(=CC=C1)C(=O)O IPBVITPZBJFMCA-UHFFFAOYSA-N 0.000 description 2
- IXGWOFPUEDTVFQ-UHFFFAOYSA-N C(C)N(N)C1=CC=C(C=C1)S(=O)(=O)O Chemical compound C(C)N(N)C1=CC=C(C=C1)S(=O)(=O)O IXGWOFPUEDTVFQ-UHFFFAOYSA-N 0.000 description 2
- JKTGKUCLQUVDND-UHFFFAOYSA-N C(C)OC1=C(C=O)C=CC(=C1)S(=O)(=O)O Chemical compound C(C)OC1=C(C=O)C=CC(=C1)S(=O)(=O)O JKTGKUCLQUVDND-UHFFFAOYSA-N 0.000 description 2
- JFJOQTMUSPHDLO-UHFFFAOYSA-N C(CCCCC)N(N)C1=CC=C(C=C1)S(=O)(=O)O Chemical compound C(CCCCC)N(N)C1=CC=C(C=C1)S(=O)(=O)O JFJOQTMUSPHDLO-UHFFFAOYSA-N 0.000 description 2
- KCAQRPUYIGDHIO-UHFFFAOYSA-N ClC=1C(=CC(=C(C=O)C1)S(=O)(=O)O)S(=O)(=O)O Chemical compound ClC=1C(=CC(=C(C=O)C1)S(=O)(=O)O)S(=O)(=O)O KCAQRPUYIGDHIO-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- LDRUNWNURNKONM-UHFFFAOYSA-N 2,4,6-trichloro-3-formylbenzoic acid Chemical compound ClC1=C(C(=O)O)C(=CC(=C1C=O)Cl)Cl LDRUNWNURNKONM-UHFFFAOYSA-N 0.000 description 1
- ROZWJSHXLAGYLT-UHFFFAOYSA-N 2,5-dichloro-4-formylbenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(C=O)C=C1Cl ROZWJSHXLAGYLT-UHFFFAOYSA-N 0.000 description 1
- BZJPIMKTHRDMKX-UHFFFAOYSA-N 2,6-dichloro-3-formylbenzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC(C=O)=C1Cl BZJPIMKTHRDMKX-UHFFFAOYSA-N 0.000 description 1
- SDXPWBZAOHPYIS-UHFFFAOYSA-N 2-chloro-4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1Cl SDXPWBZAOHPYIS-UHFFFAOYSA-N 0.000 description 1
- WASOCELOYFJJIU-UHFFFAOYSA-N 2-chloro-5-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(C=O)=CC=C1Cl WASOCELOYFJJIU-UHFFFAOYSA-N 0.000 description 1
- IXRZYMSAPALJEX-UHFFFAOYSA-N 2-fluoro-5-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(C=O)=CC=C1F IXRZYMSAPALJEX-UHFFFAOYSA-N 0.000 description 1
- AVNMSIRJVFNXSO-UHFFFAOYSA-N 2-formyl-4-hydroxybenzenesulfonic acid Chemical compound OC=1C=C(C=O)C(=CC1)S(=O)(=O)O AVNMSIRJVFNXSO-UHFFFAOYSA-N 0.000 description 1
- LXTOEAOXORNZIC-UHFFFAOYSA-N 2-formyl-6-methylbenzenesulfonic acid Chemical compound CC1=CC=CC(C=O)=C1S(O)(=O)=O LXTOEAOXORNZIC-UHFFFAOYSA-N 0.000 description 1
- XEESIWCWGFAPBD-UHFFFAOYSA-N 2-formylbenzene-1,3,5-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C(C=O)C(S(O)(=O)=O)=C1 XEESIWCWGFAPBD-UHFFFAOYSA-N 0.000 description 1
- VJANOAQDBBSULF-UHFFFAOYSA-N 2-formylbenzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1C=O VJANOAQDBBSULF-UHFFFAOYSA-N 0.000 description 1
- DILXLMRYFWFBGR-UHFFFAOYSA-N 2-formylbenzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C(C=O)=C1 DILXLMRYFWFBGR-UHFFFAOYSA-N 0.000 description 1
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
- MHEGCFHJTYVGOG-UHFFFAOYSA-N 3-(2-cyanoethyl)-4-formylbenzenesulfonic acid Chemical compound C(#N)CCC1=C(C=O)C=CC(=C1)S(=O)(=O)O MHEGCFHJTYVGOG-UHFFFAOYSA-N 0.000 description 1
- ZRNUYEXGNXMLPE-UHFFFAOYSA-N 3-(2-ethoxyethyl)-4-formylbenzenesulfonic acid Chemical compound C(C)OCCC1=C(C=O)C=CC(=C1)S(=O)(=O)O ZRNUYEXGNXMLPE-UHFFFAOYSA-N 0.000 description 1
- DCGYQZRCLYSILS-UHFFFAOYSA-N 3-[amino(methyl)amino]-4-methylbenzenesulfonic acid Chemical compound CN(N)C1=C(C=CC(=C1)S(=O)(=O)O)C DCGYQZRCLYSILS-UHFFFAOYSA-N 0.000 description 1
- QAQWFIHIZBEXFD-UHFFFAOYSA-N 3-[amino(methyl)amino]benzoic acid Chemical compound CN(N)C1=CC(=CC=C1)C(=O)O QAQWFIHIZBEXFD-UHFFFAOYSA-N 0.000 description 1
- SQGXRAIEUNWHRI-UHFFFAOYSA-N 3-butyl-4-formylbenzenesulfonic acid Chemical compound C(CCC)C1=C(C=O)C=CC(=C1)S(=O)(=O)O SQGXRAIEUNWHRI-UHFFFAOYSA-N 0.000 description 1
- RZWWCCAMYORMOY-UHFFFAOYSA-N 3-chloro-2-formylbenzenesulfonic acid Chemical compound ClC=1C(=C(C=CC=1)S(=O)(=O)O)C=O RZWWCCAMYORMOY-UHFFFAOYSA-N 0.000 description 1
- RNKGHUYNFBSMNH-UHFFFAOYSA-N 3-chloro-4-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=O)C(Cl)=C1 RNKGHUYNFBSMNH-UHFFFAOYSA-N 0.000 description 1
- ZJGALBSMNQNMOC-UHFFFAOYSA-N 3-formyl-2-hydroxy-5-methylbenzenesulfonic acid Chemical compound CC1=CC(C=O)=C(O)C(=C1)S(O)(=O)=O ZJGALBSMNQNMOC-UHFFFAOYSA-N 0.000 description 1
- KQLRFWVNJUCXQT-UHFFFAOYSA-N 3-formyl-4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1C=O KQLRFWVNJUCXQT-UHFFFAOYSA-N 0.000 description 1
- PEULTQMQZORNLA-UHFFFAOYSA-N 3-formyl-4-propan-2-yloxybenzoic acid Chemical compound CC(C)OC1=CC=C(C(O)=O)C=C1C=O PEULTQMQZORNLA-UHFFFAOYSA-N 0.000 description 1
- UZHGMEKLLSWCDS-UHFFFAOYSA-N 4-[amino(ethyl)amino]benzoic acid Chemical compound C(C)N(N)C1=CC=C(C=C1)C(=O)O UZHGMEKLLSWCDS-UHFFFAOYSA-N 0.000 description 1
- BJWQWDCZAOFFLM-UHFFFAOYSA-N 4-[amino(methyl)amino]benzoic acid Chemical compound CN(N)C1=CC=C(C(O)=O)C=C1 BJWQWDCZAOFFLM-UHFFFAOYSA-N 0.000 description 1
- GXVMCBCQOJISCX-UHFFFAOYSA-N 4-chloro-2-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1C=O GXVMCBCQOJISCX-UHFFFAOYSA-N 0.000 description 1
- AMZDKMDHDIKPKK-UHFFFAOYSA-N 4-chloro-3-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(C=O)=C1 AMZDKMDHDIKPKK-UHFFFAOYSA-N 0.000 description 1
- SKPWEADPCJMLID-UHFFFAOYSA-N 4-fluoro-3-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(C=O)=C1 SKPWEADPCJMLID-UHFFFAOYSA-N 0.000 description 1
- VWCQCCWIWMJKQQ-UHFFFAOYSA-N 4-formyl-3-hexoxybenzenesulfonic acid Chemical compound C(CCCCC)OC1=C(C=O)C=CC(=C1)S(=O)(=O)O VWCQCCWIWMJKQQ-UHFFFAOYSA-N 0.000 description 1
- XOCRTNXXJKNEDO-UHFFFAOYSA-N 4-formyl-3-methoxybenzenesulfonic acid Chemical compound COC1=C(C=O)C=CC(=C1)S(=O)(=O)O XOCRTNXXJKNEDO-UHFFFAOYSA-N 0.000 description 1
- PQYVGRGYAZDHFY-UHFFFAOYSA-N 4-formylbenzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=O)C(S(O)(=O)=O)=C1 PQYVGRGYAZDHFY-UHFFFAOYSA-N 0.000 description 1
- XSAOGXMGZVFIIE-UHFFFAOYSA-N 4-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=O)C=C1 XSAOGXMGZVFIIE-UHFFFAOYSA-N 0.000 description 1
- UNPFGHWGINGTEQ-UHFFFAOYSA-N 5-chloro-2-formyl-4-methylbenzenesulfonic acid Chemical compound ClC1=C(C=C(C=O)C(=C1)S(=O)(=O)O)C UNPFGHWGINGTEQ-UHFFFAOYSA-N 0.000 description 1
- LLESHAOZCBMEGH-UHFFFAOYSA-N 5-ethoxy-2-formyl-4-(2-methylpropyl)benzenesulfonic acid Chemical compound C(C)OC1=C(C=C(C=O)C(=C1)S(=O)(=O)O)CC(C)C LLESHAOZCBMEGH-UHFFFAOYSA-N 0.000 description 1
- UHYRCTRGSKIWNH-UHFFFAOYSA-N 5-formyl-2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(C=O)C=C1S(O)(=O)=O UHYRCTRGSKIWNH-UHFFFAOYSA-N 0.000 description 1
- NYLQWZDOUGUUFA-UHFFFAOYSA-N 5-formyl-2-iodobenzenesulfonic acid Chemical compound IC1=C(C=C(C=O)C=C1)S(=O)(=O)O NYLQWZDOUGUUFA-UHFFFAOYSA-N 0.000 description 1
- CXANNMZOMWEXTN-UHFFFAOYSA-N 5-formyl-2-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(C=O)C=C1S(O)(=O)=O CXANNMZOMWEXTN-UHFFFAOYSA-N 0.000 description 1
- LWXVYNDWXAKJPU-UHFFFAOYSA-N 5-formyl-2-propan-2-yloxybenzenesulfonic acid Chemical compound C(C)(C)OC1=C(C=C(C=O)C=C1)S(=O)(=O)O LWXVYNDWXAKJPU-UHFFFAOYSA-N 0.000 description 1
- ITFUDAFBUBAQFY-UHFFFAOYSA-N 5-formyl-4-hydroxybenzene-1,3-disulfonic acid Chemical compound OC1=C(C=O)C=C(S(O)(=O)=O)C=C1S(O)(=O)=O ITFUDAFBUBAQFY-UHFFFAOYSA-N 0.000 description 1
- VSQKSEMZHQSLOT-UHFFFAOYSA-N 5-formylbenzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(C=O)=CC(S(O)(=O)=O)=C1 VSQKSEMZHQSLOT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- CDSGGYJPQRXASK-UHFFFAOYSA-N C(#N)C(C)N(N)C1=C(C=C(C=C1)S(=O)(=O)O)C#N Chemical compound C(#N)C(C)N(N)C1=C(C=C(C=C1)S(=O)(=O)O)C#N CDSGGYJPQRXASK-UHFFFAOYSA-N 0.000 description 1
- BSOLHQOLMMWWSA-UHFFFAOYSA-N C(C)N(N)C1=CC(=CC=C1C(=O)O)Br Chemical compound C(C)N(N)C1=CC(=CC=C1C(=O)O)Br BSOLHQOLMMWWSA-UHFFFAOYSA-N 0.000 description 1
- IPHIRTLLALCELO-UHFFFAOYSA-N CCOC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1C=O Chemical compound CCOC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1C=O IPHIRTLLALCELO-UHFFFAOYSA-N 0.000 description 1
- BYHSGZZMPXXNLI-UHFFFAOYSA-N CN(N)C1=C(C=C(C=C1)S(=O)(=O)O)Cl Chemical compound CN(N)C1=C(C=C(C=C1)S(=O)(=O)O)Cl BYHSGZZMPXXNLI-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- LOQVOFUCFCWEGO-UHFFFAOYSA-N N#CC(C(S(O)(=O)=O)=C1)=CC(C=O)=C1S(O)(=O)=O Chemical compound N#CC(C(S(O)(=O)=O)=C1)=CC(C=O)=C1S(O)(=O)=O LOQVOFUCFCWEGO-UHFFFAOYSA-N 0.000 description 1
- UGYNQCFWDHGPHB-UHFFFAOYSA-N OCCC1=C(C=O)C=CC(=C1)S(=O)(=O)O Chemical compound OCCC1=C(C=O)C=CC(=C1)S(=O)(=O)O UGYNQCFWDHGPHB-UHFFFAOYSA-N 0.000 description 1
- IHGVOGHGCMLFEI-UHFFFAOYSA-N OS(C1=CC(S(O)(=O)=O)=C(C=O)C(Cl)=C1)(=O)=O Chemical compound OS(C1=CC(S(O)(=O)=O)=C(C=O)C(Cl)=C1)(=O)=O IHGVOGHGCMLFEI-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910001413 alkali metal ion Inorganic materials 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- UOBCZXSWQQWTGC-UHFFFAOYSA-N amino(phenyl)carbamic acid Chemical class OC(=O)N(N)C1=CC=CC=C1 UOBCZXSWQQWTGC-UHFFFAOYSA-N 0.000 description 1
- ZMJZYXKPJWGDGR-UHFFFAOYSA-N aminosulfamic acid Chemical compound NNS(O)(=O)=O ZMJZYXKPJWGDGR-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- UUKHCUPMVISNFW-UHFFFAOYSA-L disodium;4-formylbenzene-1,3-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=C(C=O)C(S([O-])(=O)=O)=C1 UUKHCUPMVISNFW-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000036449 good health Effects 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 150000004031 phenylhydrazines Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940045998 sodium isethionate Drugs 0.000 description 1
- LADXKQRVAFSPTR-UHFFFAOYSA-M sodium;2-hydroxyethanesulfonate Chemical compound [Na+].OCCS([O-])(=O)=O LADXKQRVAFSPTR-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- 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
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51744365A | 1965-12-29 | 1965-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH495959A true CH495959A (de) | 1970-09-15 |
Family
ID=24059822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1690866A CH495959A (de) | 1965-12-29 | 1966-11-25 | Verfahren zur Herstellung von Sonnenlicht filternden Stoffen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3462479A (en:Method) |
| BE (1) | BE691462A (en:Method) |
| CH (1) | CH495959A (en:Method) |
| DE (1) | DE1568725A1 (en:Method) |
| FR (1) | FR1506841A (en:Method) |
| GB (1) | GB1172509A (en:Method) |
| NL (1) | NL6617904A (en:Method) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3176608D1 (en) * | 1980-05-21 | 1988-02-18 | Ciba Geigy Ag | Process for the preparation of a uv-absorbing mask |
| US6998113B1 (en) | 2005-01-31 | 2006-02-14 | Aquea Scientific Corporation | Bodywashes containing additives |
| US7037513B1 (en) | 2005-01-31 | 2006-05-02 | Aquea Scientific Corporation | Bodywash additives |
| US20060173709A1 (en) * | 2005-01-31 | 2006-08-03 | Traynor Daniel H | Bodywash additive business methods |
| US7025952B1 (en) | 2005-01-31 | 2006-04-11 | Aquea Scientific Corporation | Methods of preparation and use of bodywashes containing additives |
| US7001592B1 (en) | 2005-01-31 | 2006-02-21 | Aquea Scientific Corporation | Sunscreen compositions and methods of use |
| US20080112904A1 (en) * | 2005-03-08 | 2008-05-15 | Daniel Henry Traynor | Sunscreen Compositions And Methods Of Use |
| AU2008254646A1 (en) * | 2007-05-21 | 2008-11-27 | Aquea Scientific Corporation | Highly charged microcapsules |
| US11724134B2 (en) | 2012-11-06 | 2023-08-15 | CoLabs International Corporation | Compositions containing a cellulose derived capsule with a sunscreen active agent |
| US11491088B2 (en) | 2012-11-06 | 2022-11-08 | CoLabs International Corporation | Compositions containing a capsule with a moisturizing agent |
| US9456966B2 (en) | 2012-11-06 | 2016-10-04 | CoLabs International Corporation | Composition containing a cellulose derived capsule with a sunscreen |
| US10322301B2 (en) | 2012-11-06 | 2019-06-18 | CoLabs International Corporation | Compositions containing a cellulose derived capsule with a sunscreen active agent |
| US11707421B2 (en) | 2012-11-06 | 2023-07-25 | Colabs Int'l Corp. | Compositions containing a flexible derived capsule with an active agent |
| US11690793B2 (en) | 2012-11-06 | 2023-07-04 | Colabs Int'l Corp. | Composition containing a cellulose derived capsule with a sunscreen |
| AU2019291885A1 (en) | 2018-06-27 | 2021-02-04 | CoLabs International Corporation | Compositions comprising silicon dioxide-based particles including one or more agents |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1935712A (en) * | 1928-03-02 | 1933-11-21 | Gen Aniline Works Inc | Ketone hydrazones, and process of making the same |
-
1965
- 1965-12-29 US US517443A patent/US3462479A/en not_active Expired - Lifetime
-
1966
- 1966-11-24 DE DE19661568725 patent/DE1568725A1/de active Pending
- 1966-11-25 CH CH1690866A patent/CH495959A/de not_active IP Right Cessation
- 1966-12-19 BE BE691462D patent/BE691462A/xx unknown
- 1966-12-20 NL NL6617904A patent/NL6617904A/xx unknown
- 1966-12-20 GB GB56896/66A patent/GB1172509A/en not_active Expired
- 1966-12-27 FR FR89039A patent/FR1506841A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1506841A (fr) | 1967-12-22 |
| BE691462A (en:Method) | 1967-05-29 |
| GB1172509A (en) | 1969-12-03 |
| NL6617904A (en:Method) | 1967-06-30 |
| DE1568725A1 (de) | 1970-04-16 |
| US3462479A (en) | 1969-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |