WO2007012623A1 - Copolymere auf basis von n-vinylpyrrolidon und verzweigten aliphatischen carbonsäuren und deren verwendung als solubilisatoren - Google Patents
Copolymere auf basis von n-vinylpyrrolidon und verzweigten aliphatischen carbonsäuren und deren verwendung als solubilisatoren Download PDFInfo
- Publication number
- WO2007012623A1 WO2007012623A1 PCT/EP2006/064554 EP2006064554W WO2007012623A1 WO 2007012623 A1 WO2007012623 A1 WO 2007012623A1 EP 2006064554 W EP2006064554 W EP 2006064554W WO 2007012623 A1 WO2007012623 A1 WO 2007012623A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- copolymers
- preparations
- water
- acid
- monomers
- Prior art date
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- 239000002904 solvent Substances 0.000 title claims abstract description 56
- 229920001577 copolymer Polymers 0.000 title claims abstract description 55
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 title claims description 12
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 41
- 239000000126 substance Substances 0.000 claims abstract description 26
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 11
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 239000004480 active ingredient Substances 0.000 claims description 21
- 239000002537 cosmetic Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 16
- 239000013543 active substance Substances 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003905 agrochemical Substances 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 235000015872 dietary supplement Nutrition 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 235000005911 diet Nutrition 0.000 claims description 3
- 230000000378 dietary effect Effects 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 2
- 229940088623 biologically active substance Drugs 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- -1 ethoxylated sorbitan fatty acid esters Chemical class 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000006104 solid solution Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 150000001735 carboxylic acids Chemical class 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 230000007928 solubilization Effects 0.000 description 6
- 238000005063 solubilization Methods 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 235000021466 carotenoid Nutrition 0.000 description 4
- 150000001747 carotenoids Chemical class 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 229940088594 vitamin Drugs 0.000 description 4
- 239000011782 vitamin Substances 0.000 description 4
- 235000013343 vitamin Nutrition 0.000 description 4
- 229930003231 vitamin Natural products 0.000 description 4
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940035674 anesthetics Drugs 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 2
- 229940018557 citraconic acid Drugs 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- 239000011159 matrix material Substances 0.000 description 2
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 2
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- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
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- 229920002554 vinyl polymer Polymers 0.000 description 2
- SGKNPYKCCQCHAE-UHFFFAOYSA-N (1-hydroxy-2-methylpropyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)OC(=O)C(C)=C SGKNPYKCCQCHAE-UHFFFAOYSA-N 0.000 description 1
- XPEMPJFPRCHICU-UHFFFAOYSA-N (1-tert-butylcyclohexyl) prop-2-enoate Chemical compound C=CC(=O)OC1(C(C)(C)C)CCCCC1 XPEMPJFPRCHICU-UHFFFAOYSA-N 0.000 description 1
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 1
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- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
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- PABGQABTFFNYFH-UHFFFAOYSA-N 2-methyl-n-octadecylprop-2-enamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C(C)=C PABGQABTFFNYFH-UHFFFAOYSA-N 0.000 description 1
- IMCBLSMMFWHLSN-UHFFFAOYSA-N 2-methyl-n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C(C)=C IMCBLSMMFWHLSN-UHFFFAOYSA-N 0.000 description 1
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- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 description 1
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- MDYPDLBFDATSCF-UHFFFAOYSA-N nonyl prop-2-enoate Chemical compound CCCCCCCCCOC(=O)C=C MDYPDLBFDATSCF-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- RZKYDQNMAUSEDZ-UHFFFAOYSA-N prop-2-enylphosphonic acid Chemical compound OP(O)(=O)CC=C RZKYDQNMAUSEDZ-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- ATZHWSYYKQKSSY-UHFFFAOYSA-N tetradecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)=C ATZHWSYYKQKSSY-UHFFFAOYSA-N 0.000 description 1
- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/08—Vinyl acetate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/10—Vinyl esters of monocarboxylic acids containing three or more carbon atoms
Definitions
- the invention relates to copolymers based on N-vinyllactams or N-vinylamides and vinyl esters of branched aliphatic carboxylic acids, their preparation and their use as solubilizers of sparingly water-soluble substances. Furthermore, the invention relates to corresponding preparations for use on humans, animals and plants.
- Solubilization is the solubilization of in a certain solvent, in particular water, difficultly or insoluble substances by surface-active compounds, the solubilizers to understand.
- Such solublisers are able to convert poorly water-soluble or water-insoluble substances into clear, at most opalescent aqueous solutions, without the chemical structure of these substances undergoing any change (see Römpp Chemie Lexikon, 9th edition, Bd.5. P. 4203, Thieme Verlag, Stuttgart, 1992).
- the solubilizates prepared are characterized in that the poorly water-soluble or water-insoluble substance is colloidally dissolved in the molecular associates of the surface-active compounds which form in aqueous solution - the so-called micelles.
- the resulting solutions are stable single-phase systems that appear optically clear to opalescent and can be prepared without energy input.
- solubilizers can improve the appearance of cosmetic formulations as well as food preparations by rendering the formulations transparent.
- the bioavailability and thus the effect of drugs can be increased by the use of solubilizers.
- solubilizers for pharmaceutical drugs and cosmetic agents mainly surfactants such as ethoxylated (hydrogenated) castor oil, ethoxylated sorbitan fatty acid esters or ethoxylated hydroxystearic acid are used.
- solubilizers described above used so far, show a number of application disadvantages. So z.
- their parenteral administration is associated with a release of histamine and a resulting drop in blood pressure (Lorenz et al., Agents and Actions, Vol. 12, 1/2, 1982).
- solubilizers have, for some sparingly soluble drugs, e.g. Clotrimazole only a small solubilizing effect.
- solid solutions refers to a state in which a substance is dispersed in a solid matrix, for example a polymer matrix, in a molecular dispersion Example when used in solid pharmaceutical administration forms of a sparingly soluble active ingredient for improved release of the active ingredient
- An important requirement of such solid solutions is that they are stable even after storage for a prolonged period of time, ie that the active ingredient should not crystallize out.
- the hygroscopicity of the solubilizers also plays an important role. Solubilizers that absorb too much water from the ambient air, lead to a flow of the solid solution and the unwanted crystallization of the active ingredients. Even when processed into dosage forms too great hygroscopicity can cause problems.
- US 4,432,881 describes hydrophobically modified polyacrylic acid having a molecular weight between 200,000 and 5,000,000 obtained by copolymerization of acrylic acid with the corresponding N-alkylacrylamides or acrylates.
- the polymers obtained are used as dispersible hydrophobic thickeners.
- U.S. 4,395,524 discloses the copolymerization of hydrophilic components (e.g., acrylamide, acrylic acid, N-vinylpyrrolidone, and the like) with N-alkylacrylamides.
- hydrophilic components e.g., acrylamide, acrylic acid, N-vinylpyrrolidone, and the like
- the polymers thus obtained having a molecular weight of from 30,000 to 2,000,000 are used as thickeners, sedimentation stabilizers or dispersants.
- EP-A-0 268 164 describes the use of copolymers of monoolefinically unsaturated acids and alkyl esters of monoolefinically unsaturated acids for the stabilization of O / W emulsions.
- EP-A 876 819 describes the use of copolymers of at least 60% by weight of N-vinylpyrrolidone and amides or esters with long-chain alkyl groups.
- EP-A 948 957 describes the use of copolymers of monoethylenically unsaturated carboxylic acids such as, for example, acrylic acid and hydrophobically modified comonomers such as N-alkyl or N, N-dialkylamides of unsaturated carboxylic acids with Ce-C3o-alkyl radicals.
- polymeric solubilizers have the disadvantages that they either do not form stable solid solutions or are too hygroscopic. They also leave room for improvement in terms of solubilization in aqueous systems.
- the object was to provide new solubilizers for pharmaceutical, cosmetic, food-processing and agro-technical applications.
- wt .-% information of the individual components add up to 100 wt .-%, and with the proviso that the sum of the amounts of b) and c) is 1 to 40 wt .-% of the total amount.
- the invention relates to their use as solubilizers for sparingly soluble in water substances and corresponding preparations.
- Suitable monomers a) are N-vinyllactams such as N-vinylpyrrolidone, N-vinylpiperidone and N-vinylcaprolactam or N-vinylamides such as N-methyl-N-vinylacetamide, N-vinylacetamide and N-vinylformamide
- Preferred monomers a) are N-vinylpyrrolidone and N-vinylcaprolactam.
- the proportion of the monomer a) in the copolymer is preferably in the range of 70 to 95 wt .-%, particularly preferably in the range of 74 to 94 wt .-%.
- hydrophobic components b) are according to the invention Vinylester of aliphatic branched rule, especially saturated branched, C 8 -C 3 -carboxylic acids.
- vinyl esters of the so-called Versatic® acids having at least 8 carbon atoms are suitable.
- the Versatic acids are highly branched saturated monocarboxylic acids having tertiary carboxyl groups, wherein the ⁇ -branching site carries at least one methyl group and the number refers to the total number of carbon atoms, so Versatic 8 is for example 2,2-dimethyl-hexanoic acid .
- Other suitable acids are, for example, 2,2-dimethylheptanoic acid, 2-ethyl-2-methylheptanoic acid, 2,2-dimethyloctanoic acid, 2-ethyl-2-methyloctanoic acid or 2,2-dimethylnonanoic acid; vinyl esters are preferred Versatic 9 and Versatic 10 acids. Such vinyl esters of Versatic acids are commercially available.
- the proportion of hydrophobic monomer units b) in the copolymer is preferably in the range of 5 to 30 wt .-%, particularly preferably 10 to 20 wt .-%.
- monomer c) vinyl acetate is used in amounts of up to 30 wt .-%.
- the sum of the amounts of monomers b) and c) is preferably 8 to 30, particularly preferably 10 to 30 wt .-%.
- the sum of components a) to c) is 100% by weight.
- copolymers may contain the following radically copolymerizable monomers d):
- NC 8 -C 3 O-AlkVl- or N NC 8 -C 3 o-dialkyl-substituted amides of monoethylenically unsaturated C 3 -C 8 -carboxylic acids, wherein the alkyl radicals are straight-chain or branched aliphatic or cycloaliphatic alkyl radicals with 8 to 30, preferably 8 to 18 carbon atoms.
- acrylic acid, methacrylic acid, dimethacrylic acid, ethacrylic acid, maleic acid, citraconic acid, methylenemalonic acid, allyligetic acid, vinylacetic acid, crotonic acid, fumaric acid, mesaconic acid and itaconic acid are suitable, preferably acrylic acid, methacrylic acid , Maleic acid or mixtures of said carboxylic acids.
- Preferred amidated comonomers are, for example, N-stearylacrylamide, N-stearylmethacrylamide, N- (1-methyl) undecylacrylamide, N- (1-methyl) undecylmethacrylamide, N-dodecylacrylamide, N-dodecylmethacrylamide, N-octylacrylamide, N-octylmethacrylic amide, N, N-dioctylacrylamide, N, N-dioctylmethacrylamide, N-cetylacrylamide, N-cetylmethacrylamide, N-dodecylacrylamide, N-dodecylmethacrylamide, N-myristylacrylamide, N-myristylmethacrylamide, N- (2-ethyl) -hexylacrylamide, N- (2-ethyl) -hexylmethacrylamid.
- maleic anhydride as a comonomer, this can be polymer-analogously reacted with N-alkylamines by ring-opening to the corresponding amides.
- Further comonomers d) are monoethylenically unsaturated C3-Ce-carboxylic klareester with a C 8 -C 3 O--alcohol, preferably a C 8 -C 8 -alcohol, advertising used to.
- acrylic or methacrylic esters with fatty alcohols having a chain length of 8 to 18 carbon atoms, where the alkyl radicals may be branched or unbranched.
- octyl acrylate 2-ethylhexyl acrylate, nonyl acrylate, decyl acrylate, lauryl acrylate, myristyl acrylate, cetyl acrylate, stearyl acrylate, oleyl acrylate, behenyl acrylate, octyl methacrylate, 2-ethylhexyl methacrylate, nonyl methacrylate, decyl methacrylate, lauryl methacrylate, myristyl methacrylate, cetyl methacrylate, stearyl methacrylate, oleyl methacrylate, behenyl methacrylate , tert-butylcyclohexyl acrylate.
- vinyl esters of long-chain aliphatic, saturated or unsaturated, unbranched C 8 -C 30 -carboxylic acids such as, for example, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, cerotic acid and melissic acid be used.
- C 8 -C 30 -alkyl vinyl ethers may be copolymerized as monomers d).
- Preferred alkyl radicals of the vinyl ethers are branched or unbranched C 1 -C 6 -alkyl chains, such as, for example, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl and n-octadecyl called.
- Suitable additional free-radically copolymerizable monomers d) are:
- Monoethylenically unsaturated carboxylic acids having 3 to 8 carbon atoms such as e.g. Acrylic acid, methacrylic acid, dimethacrylic acid, ethacrylic acid, maleic acid, citraconic acid, methylmalonic acid, allylacetic acid, crotonic acid, fumaric acid, mesaconic acid and itaconic acid.
- Acrylic acid, methacrylic acid or mixtures of said carboxylic acids are preferably used from this group of monomers.
- the monoethylenically unsaturated carboxylic acids can be used as free acid, as anhydrides and in partially or completely neutralized form in the copolymerization.
- alkali metal or alkaline earth metal bases ammonia or amines, preferably sodium hydroxide, potassium hydroxide, soda, potash, sodium bicarbonate, magnesium oxide, calci um hydroxide, calcium oxide, gaseous or aqueous ammonia, triethylamine, ethanolamine, diethanolamine, triethanolamine , Morpholine, diethylenetriamine or tetraethylenepentamine.
- ammonia or amines preferably sodium hydroxide, potassium hydroxide, soda, potash, sodium bicarbonate, magnesium oxide, calci um hydroxide, calcium oxide, gaseous or aqueous ammonia, triethylamine, ethanolamine, diethanolamine, triethanolamine , Morpholine, diethylenetriamine or tetraethylenepentamine.
- suitable comonomers d) are, for example, monoethylenically unsaturated C3-Ce carboxylic esters of short-chain C 1 -C 4 alcohols or nitriles in proportions of 0 to 5 mol% for the polymerization.
- Examples include: methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, hydroxyisobutyl methacrylate, monomethyl maleate, dimethyl maleate, monoethyl maleate, diethyl maleate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, N-dimethylacrylamide, N-tert-butylacrylamide, acrylonitrile, methacrylonitrile, dimethylaminoethyl acrylate, diethylaminoethyl acrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate and the salts of the last-mentioned monomers with carboxylic acids
- Phosphonic acid group-containing monomers such as vinylphosphonic acid, allylphosphonic acid and acrylamidomethanepropanephosphonic acid;
- Preferred monomers d) are acrylic acid, methacrylic acid, methyl methacrylate, ethyl acrylate, vinyl laurate, stearyl methacrylate and lauryl acrylate.
- the proportion of monomer building blocks d) in the copolymer is preferably in the range from 0 to 5% by weight, more preferably 0% by weight.
- the copolymers used according to the invention may have Fikentscher K values, measured at 1% strength by weight in ethanol, of from 10 to 200, preferably from 15 to 100, particularly preferably from 20 to 50.
- the copolymers are prepared by free-radically polymerizing the corresponding monomers.
- the preparation is carried out by known methods, e.g. solution, precipitation, or by reverse suspension polymerization using compounds which form radicals under the polymerization conditions.
- the polymerization temperatures are usually in the range of 30 to 200, preferably 40 to 110 0 C.
- Suitable initiators are xyharmen example, azo and peroxy and the customary redox initiator systems, such as combinations of hydrogen peroxide and reducing compounds, such as sodium sulfite, sodium bisulfite, sodium formaldehyde sulfoxylate and hydrazine.
- the reaction medium used are all customary solvents in which the monomers are soluble.
- water or alcoholic solvents e.g. Methanol, ethanol, n-propanol or isopropanol or mixtures of such alcohols with water used.
- the polymerization can also be carried out in the presence of conventional regulators, if relatively lower molecular weights are to be set.
- the solids content of the resulting organic solution is usually 20 to 60 wt .-%, in particular 25 to 40 wt .-%.
- a nonaqueous solvent used for the polymerization may then be removed by steam distillation and exchanged for water.
- the aqueous solutions of the copolymers can by various drying methods such as spray drying, fluidized spray drying, drum drying or Freeze-drying can be converted into powder form, from which an aqueous solution can be prepared by redispersing in water again.
- copolymers to be used according to the invention can in principle be used in all fields in which only sparingly soluble or insoluble substances in water are to be used either in aqueous preparations or to exert their effect in an aqueous medium. Accordingly, the copolymers are used as solubilizers of substances sparingly soluble in water, in particular biologically active substances.
- the term "poorly water-soluble” also encompasses practically insoluble substances and means that at least 30 to 100 g of water per g of substance is required for a solution of the substance in water at 20 ° C. In the case of practically insoluble substances, at least 10,000 g of water per g substance needed.
- water-sparingly soluble biologically active substances are pharmaceutical active substances for humans and animals, cosmetic or agrochemical active substances or dietary supplements or dietary active substances.
- Also suitable as the sparingly soluble substances to be solubilized are also dyes such as inorganic or organic pigments.
- amphiphilic compounds for use as solubilizers for pharmaceutical and cosmetic preparations and food preparations are provided. They possess the property of solubilizing sparingly soluble active ingredients in the field of pharmacy and cosmetics, sparingly soluble food supplements, for example vitamins and carotenoids, but also sparingly soluble active substances for use in crop protection agents and veterinary active ingredients.
- the copolymers can be used as solubilizers in cosmetic formulations.
- they are suitable as solubilizers for cosmetic oils. They have a good solubility for fats and oils, such as peanut oil, jojoba oil, coconut oil, almond oil, olive oil, palm oil, castor oil, soybean oil or wheat germ oil or for essential oils such as mountain pine oil, lavender oil, rosemary oil, pine needle oil, pine oil, eucalyptus oil, peppermint oil, sage oil, bergamot oil , Turpentine oil, lemon balm oil, sage oil, juniper oil, lemon oil, aniseed oil, cardamom oil; Peppermint oil, camphor oil etc. or for mixtures of these oils.
- fats and oils such as peanut oil, jojoba oil, coconut oil, almond oil, olive oil, palm oil, castor oil, soybean oil or wheat germ oil or for essential oils such as mountain pine oil, lavender oil, rosemary oil, pine needle oil, pine oil, eucalyptus oil,
- inventive polymers can be used as solubilizers for sparingly soluble in water or insoluble UV absorbers such as 2-hydroxy-4-methoxy benzophenone (Uvinul ® M 40, Fa. BASF), 2,2 ', 4,4'-tetrahydroxybenzophenone ( Uvinul ® D 50), 2,2'-dihydroxy-4,4'-dimethoxybenzophenone (Uvinul ® D49), 2,4-Dihydroxybenzo- phenone (Uvinul ® 400), 2-cyano-3,3-diphenylacrylate 2 ' -ethylhexylester (Uvinul ® N 539), 2,4,6-trianilino-p- (carbo-2'-ethylhexyl-1 '-oxi) -1, 3,5-triazine (Uvinul ® T 150), 3- ( 4- methoxybenzylidene) camphor (Eusolex ® 6300, Fa.
- UV absorbers such as 2-hydroxy-4-me
- the present invention therefore also cosmetic preparations containing at least one of the copolymers of the invention mentioned above as solubilizers. Preference is given to those preparations which, in addition to the solubilizer, contain one or more sparingly soluble cosmetic active ingredients, for example the abovementioned oils or UV absorbers.
- formulations are water or water / alcohol based solubilisates.
- the solubilizers according to the invention are used in a ratio of 0.2: 1 to 20: 1, preferably 1: 1 to 15: 1, more preferably 2: 1 to 12: 1 to the sparingly soluble cosmetic active ingredient.
- the content of solubilizer according to the invention in the cosmetic preparation is, depending on the active ingredient, in the range of 1 to 50 wt .-%, preferably 3 to 40 wt .-%, particularly preferably 5 to 30 wt .-%.
- auxiliaries may be added to this formulation, for example nonionic, cationic or anionic surfactants such as alkylpolyglycosides, fatty alcohol sulfates, fatty alcohol ether sulfates, alkanesulfonates, fatty alcohol ethoxylates, fatty alcohols.
- nonionic, cationic or anionic surfactants such as alkylpolyglycosides, fatty alcohol sulfates, fatty alcohol ether sulfates, alkanesulfonates, fatty alcohol ethoxylates, fatty alcohols.
- hydrophosphates alkyl betaines, sorbitan esters, POE sorbitan esters, sugar fatty acid esters, fatty acid polyglycerol esters, fatty acid partial glycerides, fatty acid carboxylates, fatty alcohol sulfosuccinates, fatty acid sarcosinates, fatty acid isethionates, fatty acid taurinates, citric acid esters, silicone copolymers, fatty acid polyglycol esters, fatty acid amides, fatty acid alkanolamides, quaternary ammonium compounds, alkylphenol oxethylates, fatty amine oxethylates , Cosolvents such as ethylene glycol, propylene glycol, glycerin and others.
- natural or synthetic compounds e.g. Lanolin derivatives, cholesterol derivatives, isopropyl myristate, isopropyl palmitate, electrolytes, dyes, preservatives, acids (e.g., lactic acid, citric acid).
- formulations are used, for example, in bath-supplement preparations such as bath oils, shaving waters, face lotions, hair lotions, colognes, toilet water and in sunscreens. Furthermore, they are used in the field of oral care, for example in toothpastes, mouthwashes or mouth creams.
- the copolymers of the invention can be used as a 100% substance or preferably as an aqueous solution.
- the solubilizer is usually dissolved in water and intensively mixed with the sparingly soluble cosmetic active ingredient to be used in each case.
- solubilizer it is also possible for the solubilizer to be intensively mixed with the sparingly soluble cosmetic active ingredient to be used in each case and then mixed with demineralized water with constant stirring.
- the claimed copolymers are also suitable for use as solubilizers in pharmaceutical preparations of any kind, which are characterized in that they may contain one or more sparingly soluble in water or insoluble in water drugs and vitamins and / or carotenoids.
- these are aqueous solutions or solubilisates for oral or particularly preferably for parenteral administration, such as injection solutions for intravenous, intramuscular or subcutaneous or intraperitoneal administration.
- the claimed copolymers are suitable for use in oral dosage forms such as tablets, capsules, powders, solutions. Here you can provide the poorly soluble drug with increased bioavailability.
- emulsions for example fat emulsions
- the claimed copolymers are suitable for processing a sparingly soluble drug.
- compositions of the above type may be obtained by processing the claimed copolymers with pharmaceutically active agents by conventional methods and using known and novel drugs.
- the application according to the invention may additionally contain pharmaceutical excipients and / or diluents.
- Cosolvents, stabilizers, preservatives are listed as auxiliary substances.
- the pharmaceutical active ingredients used are water-insoluble or sparingly soluble substances. According to DAB 9 (German Pharmacopoeia), the classification of the solubility of active pharmaceutical ingredients is as follows: sparingly soluble (soluble in 30 to 100 parts of solvent); poorly soluble (soluble in 100 to 1000 parts of solvent); practically insoluble (soluble in more than 10,000 parts solvent).
- the active ingredients can come from any indication.
- Examples include benzodiazepines, antihypertensives, vitamins, cytostatics - in particular taxol, anesthetics, neuroleptics, antidepressants, antibiotics, antifungals, fungicides, chemotherapeutics, urologics, platelet aggregation inhibitors, sulfonamides, spasmolytics, hormones, immunoglobulins, sera, thyroid therapeutics, psychotropic drugs, Parkinsonstoff and other antihyperkinetics, ophthalmics, neuropathy preparations, calcium metabolism regulators, muscle relaxants, anesthetics, lipid lowering agents, liver therapeutics, coronary agents, cardiakats, immunotherapeutics, regulatory peptides and their inhibitors, hypnotics, sedatives, gynecologics, gout agents, fibrinolytics, enzyme preparations and transport proteins, enzyme inhibitors, emetics, perfusion promoters , Diuretics, diagnostics, corticoids, cholinergics
- a possible manufacturing variant is the dissolution of the solubilizer in the aqueous phase, optionally with gentle heating and the subsequent dissolution of the Active ingredient in the aqueous solubilizer solution.
- the simultaneous dissolution of solubilizer and active ingredient in the aqueous phase is also possible.
- copolymers according to the invention can also be carried out, for example, by dispersing the active ingredient in the solubilizer, if appropriate with heating, and mixing it with water while stirring.
- compositions containing at least one of the copolymers of the invention as a solubilizer.
- Particularly preferred of the abovementioned pharmaceutical preparations are those which are parenterally administrable formulations.
- the content of solubilizer according to the invention in the pharmaceutical preparation is, depending on the active ingredient, in the range from 1 to 50 wt .-%, preferably 3 to 40 wt .-%, particularly preferably 5 to 30 wt .-%.
- copolymers according to the invention are also suitable as solubilizers in the food industry for nutrients, auxiliaries or adjuvants which are sparingly soluble in water or insoluble in water, for example.
- fat-soluble vitamins or carotenoids examples include clear, colored with carotenoids drinks.
- compositions include pesticides, herbicides, fungicides or insecticides, especially those preparations of pesticides used as spray or pouring broths.
- the water-soluble copolymers according to the invention are distinguished by a particularly good solubilizing action. They are also ideal for the production of stable solid solutions.
- VEOVA is used in the following examples for vinyl esters of Versatic acids.
- the number after the abbreviation indicates the number of carbon atoms.
- the monomers are commercially available.
- HWS pot with water bath, anchor stirrer and thermometer.
- the HWS pot had connections for 3 inlets, a reflux condenser and an inlet pipe, for the introduction of nitrogen or water vapor.
- Feed 1 was metered in in 4 hours, feed 2 in 6 hours. Then, polymerization was continued for a further two hours. Subsequently, 400 g of deionized water were added and steam introduced into the polymer solution for about 3 hours.
- Feed 1 was metered in in 4 hours, feed 2 in 6 hours. Then, polymerization was continued for a further two hours.
- the K value was 35 (measured 1 wt .-% in ethanol).
- Feed 1 was added in 4 hours. 37 g of feed 2 were added in 5 hours. After completion of feed 1, feed 3 was added in 1 hour. After completion of the subset of feed 2 was further polymerized at 70 0 C for one hour. It was then heated to an internal temperature of 75 ° C. In parallel with the heating process, the feed 2 (residual amount 52 g) was started and added in 2 hours. After the end of feed 2, polymerization was continued at 75 ° C. for a further 2 hours.
- the active ingredient and the polymer were weighed into a suitable glass vessel in a weight ratio of 1: 1 (in each case 2 g). and then added 16 ml of dimethylformamide as solvent.
- the reaction was stirred at 20 0 C for 24 hours on a magnetic stirrer.
- the solution was then pulled out on a glass plate with the aid of a 120 ⁇ m doctor blade. This was dried for 0.5 hours at RT in a fume hood and then dried in a drying oven at 50 ° C. and 10 mbar for a further 0.5 hours in order to remove the solvent quantitatively.
- the samples were then visually inspected. If the drug did not crystallize after 7 days, a stable solid solution had formed.
- phosphate buffer pH 7.0 was added until solubilizer and phosphate buffer in the weight ratio of 1: 9 were present.
- phosphate buffer pH 7.0 was added until solubilizer and phosphate buffer in the weight ratio of 1: 9 were present.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- General Preparation And Processing Of Foods (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002617080A CA2617080A1 (en) | 2005-07-29 | 2006-07-21 | Copolymers based on n-vinylpyrrolidone and branched aliphatic carboxylic acids, and their use as solubilizers |
US11/997,208 US20080200564A1 (en) | 2005-07-29 | 2006-07-21 | Copolymers Based on N-Vinylpyrrolidone and Branched Aliphatic Carbonxylic Acids, and Their Use as Solubilizers |
EP06777915A EP1913041A1 (de) | 2005-07-29 | 2006-07-21 | Copolymere auf basis von n-vinylpyrrolidon und verzweigten aliphatischen carbonsäuren und deren verwendung als solubilisatoren |
JP2008523341A JP2009503175A (ja) | 2005-07-29 | 2006-07-21 | N−ビニルピロリドンおよび分枝鎖脂肪族カルボン酸をベースとするコポリマー、および溶解剤としてのその使用 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005036328.8 | 2005-07-29 | ||
DE102005036328A DE102005036328A1 (de) | 2005-07-29 | 2005-07-29 | Copolymere auf Basis von N-Vinylpyrrolidon und verzweigten aliphatischen Carbonsäuren und deren Verwendung als Solubilisatoren |
Publications (1)
Publication Number | Publication Date |
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WO2007012623A1 true WO2007012623A1 (de) | 2007-02-01 |
Family
ID=36838511
Family Applications (1)
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PCT/EP2006/064554 WO2007012623A1 (de) | 2005-07-29 | 2006-07-21 | Copolymere auf basis von n-vinylpyrrolidon und verzweigten aliphatischen carbonsäuren und deren verwendung als solubilisatoren |
Country Status (7)
Country | Link |
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US (1) | US20080200564A1 (de) |
EP (1) | EP1913041A1 (de) |
JP (1) | JP2009503175A (de) |
CN (1) | CN101233161A (de) |
CA (1) | CA2617080A1 (de) |
DE (1) | DE102005036328A1 (de) |
WO (1) | WO2007012623A1 (de) |
Families Citing this family (6)
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WO2008064990A2 (en) * | 2006-11-30 | 2008-06-05 | Basf Se | Agrochemical formulations comprising l-vinyl-2 -pyrrolidinone co-polymers |
US9315694B2 (en) * | 2011-09-12 | 2016-04-19 | Oxea Gmbh | Vinyl acetate/vinyl 3,5,5-trimethylhexanoate copolymer binder resins |
CA2849080C (en) * | 2011-09-19 | 2021-07-13 | Rhodia Operations | Adjuvant compositions, agricultural pesticide compositions, and methods for making and using such compositions |
ES2676578T3 (es) * | 2014-02-19 | 2018-07-23 | Basf Se | Polímeros como material de soporte para uso en fabricación de filamentos fusionados |
US20190175487A1 (en) * | 2017-12-07 | 2019-06-13 | Johnson & Johnson Consumer Inc. | Oral Care Compositions |
CN111748053A (zh) * | 2020-05-18 | 2020-10-09 | 武汉杨森生物技术有限公司 | 一种抗凝血共聚物的制备方法及其应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0876819A1 (de) | 1997-05-07 | 1998-11-11 | Basf Aktiengesellschaft | Verwendung von Copolymerisaten des N-Vinyl-pyrrolidons in Zubereitungen wasserunlöslicher Stoffe |
EP0948957A2 (de) | 1998-03-18 | 1999-10-13 | Basf Aktiengesellschaft | Verwendung von Copolymerisaten monoethylenisch ungesättigter Carbonsäuren als Solubilisatoren |
WO2001029100A1 (de) | 1999-10-19 | 2001-04-26 | Basf Aktiengesellschaft | Verdicker für wässrige dispersionen |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2514100A1 (de) * | 1975-03-29 | 1976-10-07 | Henkel & Cie Gmbh | Kosmetische emulsionen vom wasser- in-oel-typ und deren herstellung |
US4432881A (en) * | 1981-02-06 | 1984-02-21 | The Dow Chemical Company | Water-dispersible hydrophobic thickening agent |
US4395524A (en) * | 1981-04-10 | 1983-07-26 | Rohm And Haas Company | Acrylamide copolymer thickener for aqueous systems |
-
2005
- 2005-07-29 DE DE102005036328A patent/DE102005036328A1/de not_active Withdrawn
-
2006
- 2006-07-21 US US11/997,208 patent/US20080200564A1/en not_active Abandoned
- 2006-07-21 WO PCT/EP2006/064554 patent/WO2007012623A1/de active Application Filing
- 2006-07-21 CA CA002617080A patent/CA2617080A1/en not_active Abandoned
- 2006-07-21 CN CNA2006800278788A patent/CN101233161A/zh active Pending
- 2006-07-21 JP JP2008523341A patent/JP2009503175A/ja not_active Withdrawn
- 2006-07-21 EP EP06777915A patent/EP1913041A1/de not_active Withdrawn
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0876819A1 (de) | 1997-05-07 | 1998-11-11 | Basf Aktiengesellschaft | Verwendung von Copolymerisaten des N-Vinyl-pyrrolidons in Zubereitungen wasserunlöslicher Stoffe |
EP0948957A2 (de) | 1998-03-18 | 1999-10-13 | Basf Aktiengesellschaft | Verwendung von Copolymerisaten monoethylenisch ungesättigter Carbonsäuren als Solubilisatoren |
WO2001029100A1 (de) | 1999-10-19 | 2001-04-26 | Basf Aktiengesellschaft | Verdicker für wässrige dispersionen |
Non-Patent Citations (1)
Title |
---|
"Römpp Chemie Lexikon", vol. 5, 1992, THIEME VERLAG, pages: 4203 |
Also Published As
Publication number | Publication date |
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JP2009503175A (ja) | 2009-01-29 |
DE102005036328A1 (de) | 2007-02-01 |
EP1913041A1 (de) | 2008-04-23 |
US20080200564A1 (en) | 2008-08-21 |
CA2617080A1 (en) | 2007-02-01 |
CN101233161A (zh) | 2008-07-30 |
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