CA1097448A - Copolymeres hydrophiles, insolubles dans l'eau - Google Patents
Copolymeres hydrophiles, insolubles dans l'eauInfo
- Publication number
- CA1097448A CA1097448A CA230,168A CA230168A CA1097448A CA 1097448 A CA1097448 A CA 1097448A CA 230168 A CA230168 A CA 230168A CA 1097448 A CA1097448 A CA 1097448A
- Authority
- CA
- Canada
- Prior art keywords
- water
- gel
- soluble
- process according
- monomer
- 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
- 229920001480 hydrophilic copolymer Polymers 0.000 title description 7
- 239000000178 monomer Substances 0.000 claims abstract description 92
- 229920000642 polymer Polymers 0.000 claims abstract description 36
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 21
- 229920001577 copolymer Polymers 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 68
- 230000008569 process Effects 0.000 claims description 58
- -1 radicals diisopropyl perdicarbonate Chemical class 0.000 claims description 52
- 239000000499 gel Substances 0.000 claims description 50
- 239000000017 hydrogel Substances 0.000 claims description 44
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 27
- 150000003254 radicals Chemical class 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 230000002363 herbicidal effect Effects 0.000 claims description 17
- 239000004615 ingredient Substances 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 15
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- 229920001451 polypropylene glycol Polymers 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 230000000361 pesticidal effect Effects 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- 239000003205 fragrance Substances 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 229940063557 methacrylate Drugs 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 238000007334 copolymerization reaction Methods 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 150000004985 diamines Chemical class 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000005442 diisocyanate group Chemical group 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003949 imides Chemical class 0.000 claims description 5
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 5
- 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 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229920001567 vinyl ester resin Polymers 0.000 claims description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 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 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 claims description 2
- 238000010894 electron beam technology Methods 0.000 claims description 2
- 125000005670 ethenylalkyl group Chemical group 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 2
- BHAYFXKTLWGHHO-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.C=CN1CCCC1=O BHAYFXKTLWGHHO-UHFFFAOYSA-N 0.000 claims 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims 1
- 229910052939 potassium sulfate Inorganic materials 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 239000003814 drug Substances 0.000 description 50
- 229940079593 drug Drugs 0.000 description 38
- 239000000243 solution Substances 0.000 description 30
- 239000002245 particle Substances 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 20
- 239000003826 tablet Substances 0.000 description 19
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 17
- 239000012948 isocyanate Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 150000002513 isocyanates Chemical class 0.000 description 16
- 230000008961 swelling Effects 0.000 description 14
- 239000012530 fluid Substances 0.000 description 13
- 230000002496 gastric effect Effects 0.000 description 13
- 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 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 11
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 11
- 150000002978 peroxides Chemical class 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000002775 capsule Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 229960002474 hydralazine Drugs 0.000 description 9
- 229960004801 imipramine Drugs 0.000 description 9
- 239000012528 membrane Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 229960003223 tripelennamine Drugs 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 8
- 239000007943 implant Substances 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- XZZXIYZZBJDEEP-UHFFFAOYSA-N imipramine hydrochloride Chemical compound [Cl-].C1CC2=CC=CC=C2N(CCC[NH+](C)C)C2=CC=CC=C21 XZZXIYZZBJDEEP-UHFFFAOYSA-N 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 7
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000003431 cross linking reagent Substances 0.000 description 6
- 238000009792 diffusion process Methods 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 229920001477 hydrophilic polymer Polymers 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical compound OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 239000004594 Masterbatch (MB) Substances 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 229960004090 maprotiline Drugs 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
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- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 4
- 229920002799 BoPET Polymers 0.000 description 4
- QSLMDECMDJKHMQ-UHFFFAOYSA-N Maprotiline Chemical compound C12=CC=CC=C2C2(CCCNC)C3=CC=CC=C3C1CC2 QSLMDECMDJKHMQ-UHFFFAOYSA-N 0.000 description 4
- 239000005041 Mylar™ Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000011248 coating agent Substances 0.000 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 description 4
- 229960003957 dexamethasone Drugs 0.000 description 4
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- 238000011068 loading method Methods 0.000 description 4
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- 229940063559 methacrylic acid Drugs 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
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- 238000011282 treatment Methods 0.000 description 4
- 229960000834 vinyl ether Drugs 0.000 description 4
- YSUCWSWKRIOILX-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2-phenylethyl)guanidine;hydrochloride Chemical compound Cl.NC(N)=NC(N)=NCCC1=CC=CC=C1 YSUCWSWKRIOILX-UHFFFAOYSA-N 0.000 description 3
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
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- 239000000417 fungicide Substances 0.000 description 3
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- JUMYIBMBTDDLNG-UHFFFAOYSA-N methylphenidate hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(C(=O)OC)C1CCCC[NH2+]1 JUMYIBMBTDDLNG-UHFFFAOYSA-N 0.000 description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
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- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 244000297179 Syringa vulgaris Species 0.000 description 2
- 235000004338 Syringa vulgaris Nutrition 0.000 description 2
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- 239000000642 acaricide Substances 0.000 description 2
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- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
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- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
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- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
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- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/44—Polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, not provided for in a single one of groups B01D71/26-B01D71/42
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/06—Organic material
- B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
- B01D71/80—Block polymers
-
- 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)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Materials Engineering (AREA)
- Pest Control & Pesticides (AREA)
- Dispersion Chemistry (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Dermatology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Toxicology (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48374374A | 1974-06-27 | 1974-06-27 | |
| US483743 | 1974-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1097448A true CA1097448A (fr) | 1981-03-10 |
Family
ID=23921343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA230,168A Expired CA1097448A (fr) | 1974-06-27 | 1975-06-25 | Copolymeres hydrophiles, insolubles dans l'eau |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5927766B2 (fr) |
| AT (1) | AT336891B (fr) |
| AU (1) | AU498575B2 (fr) |
| BE (1) | BE830653A (fr) |
| CA (1) | CA1097448A (fr) |
| CH (1) | CH616694A5 (fr) |
| DE (1) | DE2528068A1 (fr) |
| DK (1) | DK152740C (fr) |
| ES (1) | ES438862A1 (fr) |
| FR (1) | FR2276063A1 (fr) |
| GB (1) | GB1511563A (fr) |
| IE (1) | IE41567B1 (fr) |
| IL (1) | IL47577A (fr) |
| NL (1) | NL7507704A (fr) |
| NZ (1) | NZ177941A (fr) |
| SE (1) | SE429049B (fr) |
| ZA (1) | ZA754096B (fr) |
Families Citing this family (23)
| 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 |
| GB1594389A (en) * | 1977-06-03 | 1981-07-30 | Max Planck Gesellschaft | Dressing material for wounds |
| 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 |
| EP0000507B1 (fr) * | 1977-07-20 | 1982-09-29 | Ciba-Geigy Ag | Procédé de préparation d'hydrogels sous forme de perles sphériques de plus grand diamètre |
| US4136250A (en) * | 1977-07-20 | 1979-01-23 | Ciba-Geigy Corporation | Polysiloxane hydrogels |
| 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 |
| ES2043619T3 (es) * | 1986-05-14 | 1994-01-01 | Takiron Co | Adhesivo para administracion percutanea. |
| 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 |
| US4931282A (en) * | 1987-11-25 | 1990-06-05 | Minnesota Mining And Manufacturing Company | Pressure-sensitive medical sealant |
| US5019636A (en) * | 1989-05-10 | 1991-05-28 | Allied-Signal Inc. | Polyester chain-extended vinyl ether urethane oligomers |
| US5210111A (en) * | 1991-08-22 | 1993-05-11 | Ciba-Geigy Corporation | Crosslinked hydrogels derived from hydrophilic polymer backbones |
| 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 |
| KR101578564B1 (ko) * | 2007-08-02 | 2015-12-28 | 바스프 에스이 | 활성 물질 포함 중합체 네트워크, 이의 제조 방법 및 이의 용도 |
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 |
| NL96621C (fr) * | 1970-08-05 | |||
| 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 JP JP50077135A patent/JPS5927766B2/ja not_active Expired
- 1975-06-24 FR FR7519686A patent/FR2276063A1/fr active Granted
- 1975-06-24 DE DE19752528068 patent/DE2528068A1/de active Granted
- 1975-06-25 GB GB26942/75A patent/GB1511563A/en not_active Expired
- 1975-06-25 CA CA230,168A patent/CA1097448A/fr not_active Expired
- 1975-06-25 ES ES438862A patent/ES438862A1/es not_active Expired
- 1975-06-25 AT AT486875A patent/AT336891B/de not_active IP Right Cessation
- 1975-06-26 NZ NZ177941A patent/NZ177941A/xx unknown
- 1975-06-26 BE BE157688A patent/BE830653A/fr not_active IP Right Cessation
- 1975-06-26 IE IE1419/75A patent/IE41567B1/en unknown
- 1975-06-26 ZA ZA00754096A patent/ZA754096B/xx unknown
- 1975-06-26 IL IL47577A patent/IL47577A/xx unknown
- 1975-06-27 NL NL7507704A patent/NL7507704A/xx not_active Application Discontinuation
- 1975-07-21 AU AU82487/75A patent/AU498575B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE830653A (fr) | 1975-12-29 |
| IE41567L (en) | 1975-12-27 |
| IE41567B1 (en) | 1980-01-30 |
| DK273175A (da) | 1975-12-28 |
| AT336891B (de) | 1977-05-25 |
| NZ177941A (en) | 1978-06-20 |
| DK152740B (da) | 1988-05-02 |
| DE2528068A1 (de) | 1976-01-08 |
| JPS51125142A (en) | 1976-11-01 |
| FR2276063B1 (fr) | 1978-07-28 |
| GB1511563A (en) | 1978-05-24 |
| DE2528068C2 (fr) | 1989-03-16 |
| ZA754096B (en) | 1976-05-26 |
| IL47577A (en) | 1978-08-31 |
| ATA486875A (de) | 1976-09-15 |
| FR2276063A1 (fr) | 1976-01-23 |
| IL47577A0 (en) | 1975-08-31 |
| JPS5927766B2 (ja) | 1984-07-07 |
| SE429049B (sv) | 1983-08-08 |
| AU498575B2 (en) | 1979-03-15 |
| DK152740C (da) | 1988-10-10 |
| ES438862A1 (es) | 1977-02-01 |
| CH616694A5 (en) | 1980-04-15 |
| SE7507025L (sv) | 1975-12-29 |
| AU8248775A (en) | 1977-01-06 |
| NL7507704A (nl) | 1975-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |