DE10005942A1 - Verfahren zur Herstellung von wasserlöslichen oder wasserdispergierbaren polyetherhaltigen Polymerisaten sowie deren Verwendung als Überzugsmittel, Bindemittel und/oder filmbildende Hilfsstoffe in pharmazeutischen Darreichungsformen oder Verpackungsmaterialien oder als Zusatzstoffe in kosmetischen, dermatologischen oder hygienischen Zubereitungen - Google Patents
Verfahren zur Herstellung von wasserlöslichen oder wasserdispergierbaren polyetherhaltigen Polymerisaten sowie deren Verwendung als Überzugsmittel, Bindemittel und/oder filmbildende Hilfsstoffe in pharmazeutischen Darreichungsformen oder Verpackungsmaterialien oder als Zusatzstoffe in kosmetischen, dermatologischen oder hygienischen ZubereitungenInfo
- Publication number
- DE10005942A1 DE10005942A1 DE10005942A DE10005942A DE10005942A1 DE 10005942 A1 DE10005942 A1 DE 10005942A1 DE 10005942 A DE10005942 A DE 10005942A DE 10005942 A DE10005942 A DE 10005942A DE 10005942 A1 DE10005942 A1 DE 10005942A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- radical initiator
- acid
- hydrogen
- polymers
- Prior art date
- 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.)
- Withdrawn
Links
- 239000003999 initiator Substances 0.000 title claims abstract description 27
- 229920000570 polyether Polymers 0.000 title claims abstract description 25
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 17
- 239000007787 solid Substances 0.000 title claims abstract description 16
- 229920001567 vinyl ester resin Polymers 0.000 title claims abstract description 16
- 239000007788 liquid Substances 0.000 title claims abstract description 13
- 239000002904 solvent Substances 0.000 title claims abstract description 12
- 229920001515 polyalkylene glycol Polymers 0.000 title claims abstract description 11
- 230000000379 polymerizing effect Effects 0.000 title claims abstract description 8
- 238000000576 coating method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 13
- 239000004721 Polyphenylene oxide Substances 0.000 title abstract description 12
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title description 10
- 239000000178 monomer Substances 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 11
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 8
- 125000000732 arylene group Chemical group 0.000 claims abstract description 4
- -1 R 10 hydrogen Chemical class 0.000 claims description 79
- 229920000642 polymer Polymers 0.000 claims description 38
- 150000003254 radicals Chemical class 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000002537 cosmetic Substances 0.000 claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 7
- 239000002552 dosage form Substances 0.000 claims description 5
- 229920001290 polyvinyl ester Polymers 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 14
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 14
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007921 spray Substances 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 7
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 239000004327 boric acid Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229920002266 Pluriol® Polymers 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000007941 film coated tablet Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical class C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 4
- GDFCSMCGLZFNFY-UHFFFAOYSA-N Dimethylaminopropyl Methacrylamide Chemical compound CN(C)CCCNC(=O)C(C)=C GDFCSMCGLZFNFY-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 239000008118 PEG 6000 Substances 0.000 description 4
- 229920002584 Polyethylene Glycol 6000 Polymers 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 230000001105 regulatory effect Effects 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920002873 Polyethylenimine Polymers 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910021538 borax Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 3
- 229940008406 diethyl sulfate Drugs 0.000 description 3
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 3
- 210000004051 gastric juice Anatomy 0.000 description 3
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 3
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000223 polyglycerol Polymers 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 235000010339 sodium tetraborate Nutrition 0.000 description 3
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-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
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- SJIXRGNQPBQWMK-UHFFFAOYSA-N DEAEMA Natural products CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000001253 acrylic acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- AJFXNBUVIBKWBT-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] AJFXNBUVIBKWBT-UHFFFAOYSA-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
- 125000004185 ester group Chemical group 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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- 238000009736 wetting Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/2853—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers, poly(lactide-co-glycolide)
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Graft Or Block Polymers (AREA)
- Medicinal Preparation (AREA)
- Polymerisation Methods In General (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10005942A DE10005942A1 (de) | 2000-02-09 | 2000-02-09 | Verfahren zur Herstellung von wasserlöslichen oder wasserdispergierbaren polyetherhaltigen Polymerisaten sowie deren Verwendung als Überzugsmittel, Bindemittel und/oder filmbildende Hilfsstoffe in pharmazeutischen Darreichungsformen oder Verpackungsmaterialien oder als Zusatzstoffe in kosmetischen, dermatologischen oder hygienischen Zubereitungen |
| EP01101421A EP1125954B1 (de) | 2000-02-09 | 2001-01-23 | Verfahren zur Herstellung und Verwendung von wasserlöslichen oder wasserdispergierbaren polyetherhaltigen Polymerisaten |
| DE50114980T DE50114980D1 (de) | 2000-02-09 | 2001-01-23 | Verfahren zur Herstellung und Verwendung von wasserlöslichen oder wasserdispergierbaren polyetherhaltigen Polymerisaten |
| US09/767,821 US7465440B2 (en) | 2000-02-09 | 2001-01-24 | Process for preparing water-soluble or water-dispersible polyether-containing polymers and the use thereof as coating agents, binders and/or film-forming excipients in pharmaceutical dosage forms or packaging materials or as additives in cosmetic, dermatological or hygienic preparations |
| US09/762,046 US6458821B1 (en) | 1998-08-12 | 2001-02-01 | N-substituted azabicycloheptane derivatives, production and use thereof |
| JP2001032583A JP2001261754A (ja) | 2000-02-09 | 2001-02-08 | 水溶性または水分散性ポリエーテル含有ポリマーの製造方法、ならびに医薬剤形または包装材料におけるコーティング剤、結合剤および／もしくは被膜形成賦形剤としてのその使用、または化粧品、皮膚用製品もしくは衛生製品における添加剤としてのその使用 |
| CNB011034246A CN1171920C (zh) | 2000-02-09 | 2001-02-09 | 聚乙烯基酯的接枝共聚物及其制备方法和用途 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10005942A DE10005942A1 (de) | 2000-02-09 | 2000-02-09 | Verfahren zur Herstellung von wasserlöslichen oder wasserdispergierbaren polyetherhaltigen Polymerisaten sowie deren Verwendung als Überzugsmittel, Bindemittel und/oder filmbildende Hilfsstoffe in pharmazeutischen Darreichungsformen oder Verpackungsmaterialien oder als Zusatzstoffe in kosmetischen, dermatologischen oder hygienischen Zubereitungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10005942A1 true DE10005942A1 (de) | 2001-08-16 |
Family
ID=7630483
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10005942A Withdrawn DE10005942A1 (de) | 1998-08-12 | 2000-02-09 | Verfahren zur Herstellung von wasserlöslichen oder wasserdispergierbaren polyetherhaltigen Polymerisaten sowie deren Verwendung als Überzugsmittel, Bindemittel und/oder filmbildende Hilfsstoffe in pharmazeutischen Darreichungsformen oder Verpackungsmaterialien oder als Zusatzstoffe in kosmetischen, dermatologischen oder hygienischen Zubereitungen |
| DE50114980T Expired - Lifetime DE50114980D1 (de) | 2000-02-09 | 2001-01-23 | Verfahren zur Herstellung und Verwendung von wasserlöslichen oder wasserdispergierbaren polyetherhaltigen Polymerisaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50114980T Expired - Lifetime DE50114980D1 (de) | 2000-02-09 | 2001-01-23 | Verfahren zur Herstellung und Verwendung von wasserlöslichen oder wasserdispergierbaren polyetherhaltigen Polymerisaten |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7465440B2 (https=) |
| EP (1) | EP1125954B1 (https=) |
| JP (1) | JP2001261754A (https=) |
| CN (1) | CN1171920C (https=) |
| DE (2) | DE10005942A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10214087A1 (de) * | 2002-03-28 | 2003-10-23 | Fraunhofer Ges Forschung | Wasserlösliche verzweigte Blockcopolymere |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1123942B1 (en) * | 2000-02-10 | 2004-05-06 | Nippon Shokubai Co., Ltd. | Amino-group-containing polymer (salt) and production process therefor |
| DE10042815A1 (de) | 2000-08-30 | 2002-03-14 | Basf Ag | Verwendung von gepfropften Polyalkylenoxiden als Vergrauungsinhibitoren beim Waschen |
| DE10050958A1 (de) * | 2000-10-13 | 2002-04-18 | Basf Ag | Verwendung von wasserlöslichen oder wasserdispergierbaren Polyetherblöcken enthaltenden Pfropfpolymerisaten als Beschichtungs- und Verpackungsmittel für Wasch-, Reinigungs- und Wäschebehandlungsmitte |
| DE10128531A1 (de) * | 2001-06-13 | 2002-12-19 | Basf Ag | Verwendung von wasserlöslichen oder wasserdispergierbaren Polyetherblöcke enthaltenden Pfropfpolymerisaten als Beschichtungsmittel, Matrixbildner und/oder Verpackungsmaterial für Agrochemikalien |
| US6667023B2 (en) * | 2002-03-01 | 2003-12-23 | Akzo Nobel N.V. | Preparation of MFI type crystalline zeolitic aluminosilicate |
| DE102006055473B4 (de) | 2005-12-21 | 2019-05-16 | Basf Se | Verfahren zur Herstellung von Pfropfcopolymeren auf Basis von Polyethern |
| JP5535086B2 (ja) * | 2008-01-22 | 2014-07-02 | ビーエーエスエフ ソシエタス・ヨーロピア | 被覆ポリオキシメチレン |
| US8029912B2 (en) | 2008-02-06 | 2011-10-04 | Basf Se | Coated polyoxymethylenes |
| CN101952352B (zh) * | 2008-02-13 | 2013-03-27 | 巴斯夫欧洲公司 | 经涂覆的聚甲醛 |
| WO2011032860A1 (de) * | 2009-09-18 | 2011-03-24 | Basf Se | Verfahren zur herstellung von zubereitungen von in wasser schwerlöslichen substanzen |
| WO2011061076A1 (de) | 2009-11-17 | 2011-05-26 | Basf Se | Verfahren zur herstellung von pfropfcopolymeren auf basis von polyethern |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2602079A (en) | 1948-11-12 | 1952-07-01 | Petrolite Corp | Oxyalkylated derivatives of resinous polymers of vinyl esters |
| DE1077430B (de) * | 1958-04-15 | 1960-03-10 | Hoechst Ag | Verfahren zur Herstellung von Pfropfpolymerisaten von Polyvinylestern |
| FR1222944A (fr) | 1958-04-15 | 1960-06-14 | Hoechst Ag | Polymères greffés et leur procédé de préparation |
| NL113645C (https=) | 1958-05-31 | |||
| US3928255A (en) * | 1971-02-22 | 1975-12-23 | Cpc International Inc | Chemically joined, phase separated self-cured hydrophilic thermoplastic graft copolymers and their preparation |
| US4085168A (en) * | 1971-02-22 | 1978-04-18 | Cpc International Inc. | Chemically joined, phase separated self-cured hydrophilic thermoplastic graft copolymers and their preparation |
| EP0039854B1 (de) * | 1980-05-09 | 1985-01-30 | Hoechst Aktiengesellschaft | Polyvinylalkohol-Komposition, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE3835840A1 (de) * | 1988-10-21 | 1990-05-31 | Hoechst Ag | Polyvinylacetalgruppen enthaltende pfropfpolymerisate auf polyurethanpfropfgrundlagen, verfahren zu ihrer herstellung und ihre verwendung |
| DE3924811A1 (de) * | 1989-07-27 | 1991-01-31 | Hoechst Ag | Pfropfpolymerisat mit ungesaettigten seitenketten, dieses enthaltendes lichtempfindliches gemisch sowie daraus hergestelltes aufzeichnungsmaterial |
| US5338814A (en) * | 1993-04-21 | 1994-08-16 | Isp Investments Inc. | Process for making narrow molecular weight distribution polyvinylpyrrolidone K-90 polymers |
| DE4403866A1 (de) * | 1994-02-08 | 1995-08-10 | Basf Ag | Amphiphile Polyester, Verfahren zu ihrer Herstellung und ihre Verwendung in Waschmitteln |
| DE19536808A1 (de) * | 1995-10-02 | 1997-04-03 | Basf Lacke & Farben | Verfahren zur Herstellung von photopolymeren Hochdruckplatten |
| CA2232489A1 (en) * | 1995-12-01 | 1997-06-12 | Janssen Pharmaceutica N.V. | Cisapride sustained release |
| CN1165296C (zh) * | 1998-09-30 | 2004-09-08 | Basf公司 | 水溶性或水可分散性含聚醚聚合物作为在药物给药形式中的包衣剂、粘合剂和/或成膜赋形剂的应用 |
-
2000
- 2000-02-09 DE DE10005942A patent/DE10005942A1/de not_active Withdrawn
-
2001
- 2001-01-23 DE DE50114980T patent/DE50114980D1/de not_active Expired - Lifetime
- 2001-01-23 EP EP01101421A patent/EP1125954B1/de not_active Expired - Lifetime
- 2001-01-24 US US09/767,821 patent/US7465440B2/en not_active Expired - Fee Related
- 2001-02-08 JP JP2001032583A patent/JP2001261754A/ja not_active Withdrawn
- 2001-02-09 CN CNB011034246A patent/CN1171920C/zh not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10214087A1 (de) * | 2002-03-28 | 2003-10-23 | Fraunhofer Ges Forschung | Wasserlösliche verzweigte Blockcopolymere |
| DE10214087B4 (de) * | 2002-03-28 | 2004-05-06 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Wasserlösliche verzweigte Blockcopolymere |
Also Published As
| Publication number | Publication date |
|---|---|
| US7465440B2 (en) | 2008-12-16 |
| JP2001261754A (ja) | 2001-09-26 |
| DE50114980D1 (de) | 2009-08-27 |
| CN1308091A (zh) | 2001-08-15 |
| US20010018489A1 (en) | 2001-08-30 |
| CN1171920C (zh) | 2004-10-20 |
| EP1125954B1 (de) | 2009-07-15 |
| EP1125954A2 (de) | 2001-08-22 |
| EP1125954A3 (de) | 2001-10-24 |
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Legal Events
| Date | Code | Title | Description |
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| 8130 | Withdrawal |