DE2528068C2 - - Google Patents
Info
- Publication number
- DE2528068C2 DE2528068C2 DE2528068A DE2528068A DE2528068C2 DE 2528068 C2 DE2528068 C2 DE 2528068C2 DE 2528068 A DE2528068 A DE 2528068A DE 2528068 A DE2528068 A DE 2528068A DE 2528068 C2 DE2528068 C2 DE 2528068C2
- Authority
- DE
- Germany
- Prior art keywords
- water
- hydrogel
- alkyl
- hours
- carbon atoms
- 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.)
- Expired
Links
- -1 hydroxyalkyl maleates Chemical class 0.000 claims description 69
- 239000000178 monomer Substances 0.000 claims description 59
- 239000000017 hydrogel Substances 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 39
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 29
- 239000000499 gel Substances 0.000 claims description 23
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 claims description 19
- 238000006116 polymerization reaction Methods 0.000 claims description 19
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 150000003254 radicals Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 230000002209 hydrophobic effect Effects 0.000 claims description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 229960002474 hydralazine Drugs 0.000 claims description 9
- 229920001451 polypropylene glycol Polymers 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000003205 fragrance Substances 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- 238000007334 copolymerization reaction Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 4
- 229960003957 dexamethasone Drugs 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims description 4
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- 239000004009 herbicide Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- MBGGBVCUIVRRBF-UHFFFAOYSA-N sulfinpyrazone Chemical compound O=C1N(C=2C=CC=CC=2)N(C=2C=CC=CC=2)C(=O)C1CCS(=O)C1=CC=CC=C1 MBGGBVCUIVRRBF-UHFFFAOYSA-N 0.000 claims description 4
- 229960003329 sulfinpyrazone Drugs 0.000 claims description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- 239000000739 antihistaminic agent Substances 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 229920001567 vinyl ester resin Polymers 0.000 claims description 3
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
- 230000001387 anti-histamine Effects 0.000 claims description 2
- 125000005670 ethenylalkyl group Chemical group 0.000 claims description 2
- 229960004801 imipramine Drugs 0.000 claims description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- NOVZFMNCTCKLPF-UHFFFAOYSA-N 2,5-bis(aziridin-1-yl)-3,6-dipropoxycyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C(OCCC)=C(N2CC2)C(=O)C(OCCC)=C1N1CC1 NOVZFMNCTCKLPF-UHFFFAOYSA-N 0.000 claims 2
- 239000008186 active pharmaceutical agent Substances 0.000 claims 2
- 239000003470 adrenal cortex hormone Substances 0.000 claims 2
- 230000001195 anabolic effect Effects 0.000 claims 2
- 230000000202 analgesic effect Effects 0.000 claims 2
- 239000003098 androgen Substances 0.000 claims 2
- 230000000954 anitussive effect Effects 0.000 claims 2
- 230000001773 anti-convulsant effect Effects 0.000 claims 2
- 230000001430 anti-depressive effect Effects 0.000 claims 2
- 230000003276 anti-hypertensive effect Effects 0.000 claims 2
- 239000001961 anticonvulsive agent Substances 0.000 claims 2
- 239000000935 antidepressant agent Substances 0.000 claims 2
- 229940005513 antidepressants Drugs 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- 229960003965 antiepileptics Drugs 0.000 claims 2
- 239000004599 antimicrobial Substances 0.000 claims 2
- 239000003096 antiparasitic agent Substances 0.000 claims 2
- 229940125687 antiparasitic agent Drugs 0.000 claims 2
- 229940124584 antitussives Drugs 0.000 claims 2
- 239000002830 appetite depressant Substances 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 2
- 229940124630 bronchodilator Drugs 0.000 claims 2
- 239000003218 coronary vasodilator agent Substances 0.000 claims 2
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 claims 2
- 239000000824 cytostatic agent Substances 0.000 claims 2
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002934 diuretic Substances 0.000 claims 2
- 239000003176 neuroleptic agent Substances 0.000 claims 2
- 229940125725 tranquilizer Drugs 0.000 claims 2
- 239000003204 tranquilizing agent Substances 0.000 claims 2
- 230000002936 tranquilizing effect Effects 0.000 claims 2
- 239000003383 uricosuric agent Substances 0.000 claims 2
- 229940124549 vasodilator Drugs 0.000 claims 2
- 239000003071 vasodilator agent Substances 0.000 claims 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 claims 1
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 claims 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 1
- LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 claims 1
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims 1
- JMBQKKAJIKAWKF-UHFFFAOYSA-N Glutethimide Chemical compound C=1C=CC=CC=1C1(CC)CCC(=O)NC1=O JMBQKKAJIKAWKF-UHFFFAOYSA-N 0.000 claims 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
- ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 claims 1
- XWALNWXLMVGSFR-HLXURNFRSA-N Methandrostenolone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 XWALNWXLMVGSFR-HLXURNFRSA-N 0.000 claims 1
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 claims 1
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 claims 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 1
- ARFHIAQFJWUCFH-IZZDOVSWSA-N Nifurtimox Chemical compound CC1CS(=O)(=O)CCN1\N=C\C1=CC=C([N+]([O-])=O)O1 ARFHIAQFJWUCFH-IZZDOVSWSA-N 0.000 claims 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 claims 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 claims 1
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- 230000000648 anti-parkinson Effects 0.000 claims 1
- 229940035678 anti-parkinson drug Drugs 0.000 claims 1
- 239000000939 antiparkinson agent Substances 0.000 claims 1
- 239000000168 bronchodilator agent Substances 0.000 claims 1
- 229960000623 carbamazepine Drugs 0.000 claims 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 claims 1
- 229960003529 diazepam Drugs 0.000 claims 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims 1
- 230000001882 diuretic effect Effects 0.000 claims 1
- 229960001022 fenoterol Drugs 0.000 claims 1
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 claims 1
- 229960000961 floxuridine Drugs 0.000 claims 1
- 229960002972 glutethimide Drugs 0.000 claims 1
- 229960002003 hydrochlorothiazide Drugs 0.000 claims 1
- 230000000147 hypnotic effect Effects 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 229940039009 isoproterenol Drugs 0.000 claims 1
- 229960004502 levodopa Drugs 0.000 claims 1
- QSLMDECMDJKHMQ-GSXCWMCISA-N maprotiline Chemical compound C12=CC=CC=C2[C@@]2(CCCNC)C3=CC=CC=C3[C@@H]1CC2 QSLMDECMDJKHMQ-GSXCWMCISA-N 0.000 claims 1
- 229960004090 maprotiline Drugs 0.000 claims 1
- 229960000299 mazindol Drugs 0.000 claims 1
- 229960003377 metandienone Drugs 0.000 claims 1
- 229960001797 methadone Drugs 0.000 claims 1
- 229960001344 methylphenidate Drugs 0.000 claims 1
- 229960001566 methyltestosterone Drugs 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 229960002009 naproxen Drugs 0.000 claims 1
- 230000000701 neuroleptic effect Effects 0.000 claims 1
- 229960002644 nifurtimox Drugs 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 claims 1
- 229960003243 phenformin Drugs 0.000 claims 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 claims 1
- 229960002895 phenylbutazone Drugs 0.000 claims 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 claims 1
- 229960003147 reserpine Drugs 0.000 claims 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims 1
- 229960001225 rifampicin Drugs 0.000 claims 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 claims 1
- 229960002784 thioridazine Drugs 0.000 claims 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims 1
- 229960001082 trimethoprim Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 description 52
- 229940079593 drug Drugs 0.000 description 49
- 239000000243 solution Substances 0.000 description 33
- 239000012948 isocyanate Substances 0.000 description 24
- 150000002513 isocyanates Chemical class 0.000 description 23
- 239000002245 particle Substances 0.000 description 23
- 239000003826 tablet Substances 0.000 description 23
- 229920000642 polymer Polymers 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 230000008961 swelling Effects 0.000 description 14
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 12
- 239000013543 active substance Substances 0.000 description 12
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 12
- 150000002978 peroxides Chemical class 0.000 description 12
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 210000004051 gastric juice Anatomy 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 230000004584 weight gain Effects 0.000 description 11
- 235000019786 weight gain Nutrition 0.000 description 11
- FSSICIQKZGUEAE-UHFFFAOYSA-N 2-[benzyl(pyridin-2-yl)amino]ethyl-dimethylazanium;chloride Chemical compound Cl.C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CC=C1 FSSICIQKZGUEAE-UHFFFAOYSA-N 0.000 description 10
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 239000011888 foil Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000009792 diffusion process Methods 0.000 description 8
- 229920001477 hydrophilic polymer Polymers 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 239000003431 cross linking reagent Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 229920001480 hydrophilic copolymer Polymers 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
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- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2210/00—Compositions for preparing hydrogels
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Materials Engineering (AREA)
- Pharmacology & Pharmacy (AREA)
- Dispersion Chemistry (AREA)
- Wood Science & Technology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Dentistry (AREA)
- Transplantation (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Materials For Medical Uses (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Medicinal Preparation (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48374374A | 1974-06-27 | 1974-06-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2528068A1 DE2528068A1 (de) | 1976-01-08 |
| DE2528068C2 true DE2528068C2 (enrdf_load_stackoverflow) | 1989-03-16 |
Family
ID=23921343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752528068 Granted DE2528068A1 (de) | 1974-06-27 | 1975-06-24 | Wasserunloesliche hydrophile copolymere |
Country Status (17)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0530140A1 (en) * | 1991-08-22 | 1993-03-03 | Ciba-Geigy Ag | Crosslinked hydrogels derived from hydrophilic polymer backbones |
| WO2009016112A3 (de) * | 2007-08-02 | 2009-12-23 | Basf Se | Wirkstoffe enthaltende polymernetzwerke, verfahren zu deren herstellung sowie deren verwendung |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU494547B2 (en) * | 1972-07-10 | 1977-10-20 | Johnson & Johnson | Hydrophilic random interpolymer compositions and method for making same |
| US4235988A (en) | 1976-12-13 | 1980-11-25 | Imperial Chemical Industries Limited | Delivery means for biologically active agents |
| DE2725261C2 (de) * | 1977-06-03 | 1986-10-09 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Transparentes Flüssigkeitsverbandmaterial, seine Herstellung und Verwendung |
| GB1594389A (en) * | 1977-06-03 | 1981-07-30 | Max Planck Gesellschaft | Dressing material for wounds |
| US4136250A (en) * | 1977-07-20 | 1979-01-23 | Ciba-Geigy Corporation | Polysiloxane hydrogels |
| EP0000507B1 (de) * | 1977-07-20 | 1982-09-29 | Ciba-Geigy Ag | Verfahren zur Herstellung von Hydrogelen in Form kugelförmiger Perlen grösseren Durchmessers |
| JPS5535910A (en) * | 1978-09-06 | 1980-03-13 | Teijin Ltd | Permselectivity composite membrane and preparation thereof |
| AT371723B (de) * | 1978-11-15 | 1983-07-25 | Max Planck Gesellschaft | Transparentes fluessigkeitsverbandmaterial, und verfahren zu seiner herstellung |
| SE431821B (sv) * | 1979-01-29 | 1984-03-05 | Perstorp Ab | Lagringsstabilt, prostaglandininnehallande medicinskt preparat |
| SE448544B (sv) * | 1979-12-05 | 1987-03-02 | Kendall & Co | Vattenabsorberande komposition och anvendning derav som berare for ett lekemedel |
| SU1243627A3 (ru) * | 1979-12-05 | 1986-07-07 | Дзе Кендалл Компани (Фирма) | Гелеобразующа композици |
| US4892736A (en) * | 1983-10-07 | 1990-01-09 | The Forsyth Dental Infirmary For Children | Intra-pocket drug delivery devices for treatment of periodontal diseases |
| JPS60199012A (ja) * | 1984-03-24 | 1985-10-08 | Toomee Sangyo Kk | コンタクトレンズ材料 |
| US4911691A (en) * | 1984-09-21 | 1990-03-27 | Menlo Care, Inc. | Assembly for adminstering IV solution |
| US4883699A (en) * | 1984-09-21 | 1989-11-28 | Menlo Care, Inc. | Polymeric article having high tensile energy to break when hydrated |
| DE3780700T2 (de) * | 1986-05-14 | 1993-02-04 | Ono Pharmaceutical Co | Klebstoff fuer perkutane verabreichung. |
| US4931282A (en) * | 1987-11-25 | 1990-06-05 | Minnesota Mining And Manufacturing Company | Pressure-sensitive medical sealant |
| US5225473A (en) * | 1987-11-25 | 1993-07-06 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesives |
| US4846185A (en) * | 1987-11-25 | 1989-07-11 | Minnesota Mining And Manufacturing Company | Bioelectrode having a galvanically active interfacing material |
| US5019636A (en) * | 1989-05-10 | 1991-05-28 | Allied-Signal Inc. | Polyester chain-extended vinyl ether urethane oligomers |
| DE19908184A1 (de) | 1999-02-25 | 2000-08-31 | Basf Ag | Verfahren zur Herstellung wässriger Dispersionen von Copolymerisaten aus hydrophilen und hydrophoben Monomeren sowie daraus erhältliche Copolymerisate und deren Anwendungen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297745A (en) * | 1962-04-05 | 1967-01-10 | Robertson Co H H | Ethylenically unsaturated di-and tetra-urethane monomers |
| US3553174A (en) * | 1967-11-27 | 1971-01-05 | Amicon Corp | Reaction product of a hydroxyacrylate and an aliphatic isocyanate and transparent article made therefrom |
| US3677920A (en) * | 1968-07-06 | 1972-07-18 | Asahi Chemical Ind | Photopolymerizable diisocyanate modified unsaturated polyester containing acrylic monomers |
| DE1065621B (de) * | 1970-08-05 | 1959-09-17 | Prag Dr Otto Wichterle | Verfahren zur Herstellung von hydrophilen, gequollenen bzw stark quellfähigen geformxen Gebilden |
| GB1352063A (en) * | 1971-01-08 | 1974-05-15 | Ici Ltd | Polymerisable compositions and resins derived thererom |
| GB1439132A (en) * | 1972-03-13 | 1976-06-09 | Special Polymers Ltd | Method for the production of a hydrophilic polymer product |
-
1975
- 1975-06-12 CH CH761775A patent/CH616694A5/de not_active IP Right Cessation
- 1975-06-17 DK DK273175A patent/DK152740C/da not_active IP Right Cessation
- 1975-06-18 SE SE7507025A patent/SE429049B/xx not_active IP Right Cessation
- 1975-06-24 DE DE19752528068 patent/DE2528068A1/de active Granted
- 1975-06-24 FR FR7519686A patent/FR2276063A1/fr active Granted
- 1975-06-24 JP JP50077135A patent/JPS5927766B2/ja not_active Expired
- 1975-06-25 AT AT486875A patent/AT336891B/de not_active IP Right Cessation
- 1975-06-25 ES ES438862A patent/ES438862A1/es not_active Expired
- 1975-06-25 CA CA230,168A patent/CA1097448A/en not_active Expired
- 1975-06-25 GB GB26942/75A patent/GB1511563A/en not_active Expired
- 1975-06-26 IE IE1419/75A patent/IE41567B1/en unknown
- 1975-06-26 NZ NZ177941A patent/NZ177941A/xx unknown
- 1975-06-26 ZA ZA00754096A patent/ZA754096B/xx unknown
- 1975-06-26 IL IL47577A patent/IL47577A/xx unknown
- 1975-06-26 BE BE157688A patent/BE830653A/xx not_active IP Right Cessation
- 1975-06-27 NL NL7507704A patent/NL7507704A/xx not_active Application Discontinuation
- 1975-07-21 AU AU82487/75A patent/AU498575B2/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0530140A1 (en) * | 1991-08-22 | 1993-03-03 | Ciba-Geigy Ag | Crosslinked hydrogels derived from hydrophilic polymer backbones |
| WO2009016112A3 (de) * | 2007-08-02 | 2009-12-23 | Basf Se | Wirkstoffe enthaltende polymernetzwerke, verfahren zu deren herstellung sowie deren verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| BE830653A (fr) | 1975-12-29 |
| SE429049B (sv) | 1983-08-08 |
| IL47577A0 (en) | 1975-08-31 |
| CA1097448A (en) | 1981-03-10 |
| SE7507025L (sv) | 1975-12-29 |
| FR2276063B1 (enrdf_load_stackoverflow) | 1978-07-28 |
| JPS5927766B2 (ja) | 1984-07-07 |
| AU498575B2 (en) | 1979-03-15 |
| AU8248775A (en) | 1977-01-06 |
| ATA486875A (de) | 1976-09-15 |
| DK152740C (da) | 1988-10-10 |
| ZA754096B (en) | 1976-05-26 |
| JPS51125142A (en) | 1976-11-01 |
| NL7507704A (nl) | 1975-12-30 |
| FR2276063A1 (fr) | 1976-01-23 |
| IE41567L (en) | 1975-12-27 |
| GB1511563A (en) | 1978-05-24 |
| ES438862A1 (es) | 1977-02-01 |
| DE2528068A1 (de) | 1976-01-08 |
| DK273175A (da) | 1975-12-28 |
| IL47577A (en) | 1978-08-31 |
| IE41567B1 (en) | 1980-01-30 |
| AT336891B (de) | 1977-05-25 |
| DK152740B (da) | 1988-05-02 |
| CH616694A5 (en) | 1980-04-15 |
| NZ177941A (en) | 1978-06-20 |
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Legal Events
| Date | Code | Title | Description |
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| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: REDIES, B., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 40 |
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| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: AGRIPAT AG, BASEL, CH |
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| 8328 | Change in the person/name/address of the agent |
Free format text: COHAUSZ, W., DIPL.-ING. KNAUF, R., DIPL.-ING. COHAUSZ, H., DIPL.-ING. WERNER, D., DIPL.-ING. DR.-ING. REDIES, B., DIPL.-CHEM. DR.RER.NAT. SCHIPPAN, R., DIPL.-ING. DR.-ING. THIELMANN, A., DIPL.-ING., PAT.-ANWAELTE, 4000 DUESSELDORF |
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