CN1171920C - 聚乙烯基酯的接枝共聚物及其制备方法和用途 - Google Patents
聚乙烯基酯的接枝共聚物及其制备方法和用途 Download PDFInfo
- Publication number
- CN1171920C CN1171920C CNB011034246A CN01103424A CN1171920C CN 1171920 C CN1171920 C CN 1171920C CN B011034246 A CNB011034246 A CN B011034246A CN 01103424 A CN01103424 A CN 01103424A CN 1171920 C CN1171920 C CN 1171920C
- Authority
- CN
- China
- Prior art keywords
- acid
- methyl
- ester
- alkyl
- radical initiator
- 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 - Lifetime
Links
- 229920000570 polyether Polymers 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 17
- 239000003814 drug Substances 0.000 title claims description 6
- 239000011248 coating agent Substances 0.000 title claims description 5
- 239000004615 ingredient Substances 0.000 title claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 15
- 229920000642 polymer Polymers 0.000 title description 14
- 239000000463 material Substances 0.000 title description 4
- 239000004721 Polyphenylene oxide Substances 0.000 title description 3
- 239000000853 adhesive Substances 0.000 title 1
- 230000001070 adhesive effect Effects 0.000 title 1
- 238000012856 packing Methods 0.000 title 1
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 30
- 239000003999 initiator Substances 0.000 claims abstract description 27
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 18
- 239000007788 liquid Substances 0.000 claims abstract description 15
- 229920001567 vinyl ester resin Polymers 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 12
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 10
- 229920001290 polyvinyl ester Polymers 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- 150000003254 radicals Chemical class 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 26
- 239000007787 solid Substances 0.000 abstract description 5
- 229910052740 iodine Inorganic materials 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- -1 polyoxyethylene Polymers 0.000 description 78
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 7
- 239000004327 boric acid Substances 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- 229920002266 Pluriol® Polymers 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000008118 PEG 6000 Substances 0.000 description 4
- 229920002584 Polyethylene Glycol 6000 Polymers 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 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
- 125000005395 methacrylic acid group Chemical group 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 4
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-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
- 125000003158 alcohol group Chemical group 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910021538 borax Inorganic materials 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 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
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000010339 sodium tetraborate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- IAUGBVWVWDTCJV-UHFFFAOYSA-N 1-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound CCC(S(O)(=O)=O)NC(=O)C=C IAUGBVWVWDTCJV-UHFFFAOYSA-N 0.000 description 2
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 2
- ZMARGGQEAJXRFP-UHFFFAOYSA-N 1-hydroxypropan-2-yl 2-methylprop-2-enoate Chemical compound OCC(C)OC(=O)C(C)=C ZMARGGQEAJXRFP-UHFFFAOYSA-N 0.000 description 2
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 2
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-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
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- TZPOVCFULKVVQI-UHFFFAOYSA-N N1C=NC=C1.C(=C)C=CC Chemical class N1C=NC=C1.C(=C)C=CC TZPOVCFULKVVQI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 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
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-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
- 235000015165 citric acid Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000002537 cosmetic Substances 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
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-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
- 238000009826 distribution Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 229960004580 glibenclamide Drugs 0.000 description 2
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YHCVYAHUIMOIGE-UHFFFAOYSA-N 2,3-dihydroxypropyl but-2-enoate Chemical compound CC=CC(=O)OCC(O)CO YHCVYAHUIMOIGE-UHFFFAOYSA-N 0.000 description 1
- YMHOBZXQZVXHBM-UHFFFAOYSA-N 2,5-dimethoxy-4-bromophenethylamine Chemical compound COC1=CC(CCN)=C(OC)C=C1Br YMHOBZXQZVXHBM-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- RCGCPJFKOPMRON-UHFFFAOYSA-N 2-(dimethylamino)ethyl but-2-enoate Chemical compound CC=CC(=O)OCCN(C)C RCGCPJFKOPMRON-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- QQBUHYQVKJQAOB-UHFFFAOYSA-N 2-ethenylfuran Chemical class C=CC1=CC=CO1 QQBUHYQVKJQAOB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
- FMYZXPWRXLBAOV-UHFFFAOYSA-N 2-hydroxyethyl 2-methylidenebutanoate Chemical compound CCC(=C)C(=O)OCCO FMYZXPWRXLBAOV-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- LPNSCOVIJFIXTJ-UHFFFAOYSA-N 2-methylidenebutanamide Chemical compound CCC(=C)C(N)=O LPNSCOVIJFIXTJ-UHFFFAOYSA-N 0.000 description 1
- XIADDNKBYXBWMA-UHFFFAOYSA-N 2-methylpropyl 2-methylidenebutanoate Chemical compound CCC(=C)C(=O)OCC(C)C XIADDNKBYXBWMA-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- CAMBAGZYTIDFBK-UHFFFAOYSA-N 3-tert-butylperoxy-2-methylpropan-1-ol Chemical compound CC(CO)COOC(C)(C)C CAMBAGZYTIDFBK-UHFFFAOYSA-N 0.000 description 1
- JBLNCBDNFKLARF-UHFFFAOYSA-N 4,5-bis(ethenyl)-1h-imidazole Chemical class C=CC=1N=CNC=1C=C JBLNCBDNFKLARF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 229920005789 ACRONAL® acrylic binder Polymers 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical group ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- YBXHSDOJCKEVRI-UHFFFAOYSA-N C(=C)C=1NC=CN1.CC1(CC(C(=O)O)=CC=C1)C(=O)O Chemical compound C(=C)C=1NC=CN1.CC1(CC(C(=O)O)=CC=C1)C(=O)O YBXHSDOJCKEVRI-UHFFFAOYSA-N 0.000 description 1
- FDFDYWKCGLKQSJ-UHFFFAOYSA-N C(C=C)(=O)OC(C)(C)C.C(C)C=CC Chemical compound C(C=C)(=O)OC(C)(C)C.C(C)C=CC FDFDYWKCGLKQSJ-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 229920001651 Cyanoacrylate Polymers 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- SNEBFJPGYXTAMX-UHFFFAOYSA-N S(=O)(=O)(OC)O.C(=C)C=1NC=CN1.CC1(CC(C(=O)O)=CC=C1)C(=O)O Chemical compound S(=O)(=O)(OC)O.C(=C)C=1NC=CN1.CC1(CC(C(=O)O)=CC=C1)C(=O)O SNEBFJPGYXTAMX-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 241000545067 Venus Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 description 1
- SPXVONMXJOSLOB-UHFFFAOYSA-M [Cl-].CC([N+](C)(C)CCCO)OC(C=C)=O Chemical compound [Cl-].CC([N+](C)(C)CCCO)OC(C=C)=O SPXVONMXJOSLOB-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical class ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000005131 dialkylammonium group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- DRZVGZCMBZUYCJ-UHFFFAOYSA-M diethyl-(3-hydroxypropyl)-(2-prop-2-enoyloxypropan-2-yl)azanium chloride Chemical compound [Cl-].CC(C)([N+](CC)(CC)CCCO)OC(C=C)=O DRZVGZCMBZUYCJ-UHFFFAOYSA-M 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- JMPVESVJOFYWTB-UHFFFAOYSA-N dipropan-2-yl carbonate Chemical class CC(C)OC(=O)OC(C)C JMPVESVJOFYWTB-UHFFFAOYSA-N 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 238000005243 fluidization Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- GFMIDCCZJUXASS-UHFFFAOYSA-N hexane-1,1,6-triol Chemical compound OCCCCCC(O)O GFMIDCCZJUXASS-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- JKJJSJJGBZXUQV-UHFFFAOYSA-N methyl 2-methylidenebutanoate Chemical class CCC(=C)C(=O)OC JKJJSJJGBZXUQV-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical group C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- MEYPYIROLGQIED-UHFFFAOYSA-N n-[12-(dimethylamino)dodecyl]-2-methylprop-2-enamide Chemical compound CN(C)CCCCCCCCCCCCNC(=O)C(C)=C MEYPYIROLGQIED-UHFFFAOYSA-N 0.000 description 1
- BPTMGBPQYPVHCN-UHFFFAOYSA-N n-[3-(dimethylamino)butyl]-2-methylprop-2-enamide Chemical compound CN(C)C(C)CCNC(=O)C(C)=C BPTMGBPQYPVHCN-UHFFFAOYSA-N 0.000 description 1
- YRVUCYWJQFRCOB-UHFFFAOYSA-N n-butylprop-2-enamide Chemical compound CCCCNC(=O)C=C YRVUCYWJQFRCOB-UHFFFAOYSA-N 0.000 description 1
- CSGOAFRNKNQONI-UHFFFAOYSA-N n-dodecyl-n-methylprop-2-enamide Chemical compound CCCCCCCCCCCCN(C)C(=O)C=C CSGOAFRNKNQONI-UHFFFAOYSA-N 0.000 description 1
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- CNWVYEGPPMQTKA-UHFFFAOYSA-N n-octadecylprop-2-enamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)C=C CNWVYEGPPMQTKA-UHFFFAOYSA-N 0.000 description 1
- BPCNEKWROYSOLT-UHFFFAOYSA-N n-phenylprop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC=C1 BPCNEKWROYSOLT-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- LYJZNXAVZMEXDH-UHFFFAOYSA-N octadecan-8-yl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCC(OC(=O)C(C)=C)CCCCCCC LYJZNXAVZMEXDH-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- AKRQMTFHUVDMIL-UHFFFAOYSA-N tetrakis(prop-2-enyl)silane Chemical compound C=CC[Si](CC=C)(CC=C)CC=C AKRQMTFHUVDMIL-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000003643 water by type Substances 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)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Graft Or Block Polymers (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Polymerisation Methods In General (AREA)
Abstract
制备聚乙烯基酯接枝共聚物的方法,该方法是通过使用自由基引发剂体系在b)存在下聚合a)和c)而进行的,其中使用液态聚亚烷基二醇作为自由基引发剂体系(进料)的溶剂:a)至少一种脂族C1-C24-羧酸的乙烯基酯;b)在室温为固态且具有通式I的聚醚;c)视需要存在的至少一种其它单体。
Description
技术领域
本发明涉及制备水溶性或水分散性含聚醚聚合物的方法及其作为药物配剂中的涂布剂、粘合剂和/或成膜赋形剂或作为化妆品、皮肤病和/或卫生保健制剂中添加剂的应用,并涉及包含这种新聚合物的化妆品、皮肤病、卫生保健和/或药物组合物。
背景技术
通过环氧乙烷对带有活性氢的聚合物如纤维素、聚酰胺等的作用而制备接枝共聚物是已知的。
U.S.说明书2,602,079公开了制备乙烯基酯烷氧基化聚合物的方法。但是其中描述的两步法是不方便和危险的,并且由于使用溶剂还是不经济的。
DE 1 077 430,DE 1 094 457和DE 1 081 229描述了制备聚乙烯基酯接枝共聚物的方法及其作为水溶性包装薄膜和作为化妆品中助剂的应用。
所引文献从总体上描述了由聚乙二醇和乙烯基酯(及其它共聚单体)制备接枝共聚物的方法。在这些情况中相应的固体聚乙二醇溶解在单体乙烯基酯中(适当时可借助溶剂),并通过加入自由基引发剂而聚合。部分混合物进行部分聚合,随后加入剩余的混合物。
以这种方式进行的方法存在相当多的安全缺陷,例如由于在聚合或进料之前接枝基体、单体和引发剂的混合。
发明内容
本发明的目的是开发一种同样可用于工业应用的安全方法,其中自由基引发剂的计量性(meterability)良好,即使是在小用量时,并且该方法不具有所述缺点。
我们发现由制备聚乙烯基酯接枝共聚物的方法可实现此目的,该方法是通过使用自由基引发剂体系在b)存在下聚合a)和c)而进行的:
a)脂族C1-C24-羧酸的至少一种乙烯基酯
b)在室温为固态且具有通式I的聚醚
c)视需要而存在的至少一种其它单体其中使用液态聚亚烷基二醇作为自由基引发剂体系的溶剂
聚合可通过常规聚合方法进行。聚合可间歇或优选以进料法(feed process)进行。
在间歇法中聚合过程可如此:将含聚醚的化合物b)溶解在a)的至少一种单体和可能的其它共聚单体c)中,加入聚合引发剂后,聚合混合物至完全。在进料法中,聚合是半连续进行的:开始时混合部分例如10%由含聚醚的化合物b)、a)的至少一种单体、可能的其它共聚单体c)及引发剂组成的用于聚合的混合物,加热混合物至聚合温度,并在引发聚合后根据聚合进程加入剩余的用于聚合的混合物。聚合物也可通过下列方法获得:将含聚醚的化合物b)引入到反应器中并加热到聚合温度,一次全部、分批或者优选与引发剂平行地连续加入a)的至少一种单体、优选其它共聚单体c)和聚合引发剂,并聚合。
与现有技术相反,将引发剂溶解在液态聚亚烷基二醇中可确保安全的反应控制。新方法的另外优点是引入另外的接枝基体可改进产品性能,不需要其它的即化学上不同的溶剂。
根据本发明制备的接枝共聚物可用作药物配料或化妆品中的涂布剂及粘合剂和/或成膜赋形剂。
用于自由基引发剂的溶剂为在室温为液态的聚亚烷基二醇。其分子量为88-1000,优选为100-600。聚乙二醇是特别优选使用的。
在室温为固态的聚醚是指通式I的聚醚
其中各变量彼此独立地具有下列含义:
R1氢、C1-C24-烷基、R9-C(=O)-、R9-NH-C(=O)-、多元醇残基;
R8氢、C1-C24-烷基、R9-C(=O)-、R9-NH-C(=O)-;
R2-R7-(CH2)2-、-(CH2)3-、-(CH2)4-、-CH2-CH(CH3)-、-CH2-CH(CH2-CH3)-、-CH2-CHOR10-CH2-;
R9 C1-C24-烷基;
R10氢、C1-C24-烷基、R9-C(=O)-;
A-C(=O)-O-、-C(=O)-B-C(=O)-O-、-C(=O)-NH-B-NH-C(=O)-O-;
B-(CH2)t-、亚芳基,任选可被取代;
n 1-8;
s 0-500;
t 1-12;
u 1-5000;
v 0-5000;
w 0-5000;
x 1-5000;
y 0-5000;
z 0-5000。
一般用作根据本发明制备的接枝共聚物的接枝基体b)为选自基于环氧乙烷、环氧丙烷和环氧丁烷的聚环氧烷和聚甘油的通式I的聚醚。根据单体单元的性质,得到含有下列结构单元的聚合物:
-(CH2)2-O-、-(CH2)3-O-、-(CH2)4-O-、-CH2-CH(CH3)-O-、-CH2-CH(CH2-CH3)-O-、-CH2-CHOR7-CH2-O-;
它们既可以是均聚物也可以是共聚物,并且共聚物可以具有无规分布或者是所谓的嵌段共聚物形式。
根据接枝度,本发明所用聚合物包括纯接枝共聚物及上述接枝共聚物与式I的未接枝聚醚和单体a)及视需要存在的其它单体c)的均聚物或共聚物的混合物。
以烯化氧或甘油为基础制备的聚醚的终端伯羟基基团、及另外的聚甘油的仲OH基团既可以未被保护的自由形式存在也可以被C1-C24链长的醇醚化或被C1-C24链长的羧酸酯化、或与异氰酸酯反应得到氨基甲酸酯。
对于R1和R8-R10可提到的烷基基团为支化或未支化的C1-C24-烷基链,优选甲基、乙基、正丙基、1-甲基乙基、正丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、正己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基、正庚基、2-乙基己基、正辛基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正十九烷基或正二十烷基。
上述可提及烷基基团的优选代表为支化或未支化的C1-C12-,特别优选C1-C6-烷基链。
用作接枝基体的聚醚的分子量范围为1000-500,000,优选为1000-100,000,特别优选为1000-20,000,非常特别优选为1000-15,000。
使用环氧乙烷均聚物或环氧乙烷含量为40-99wt%的共聚物是有利的。因此,在优选使用的环氧乙烷聚合物中环氧乙烷单元的含量为40-100mol%。适于作为这些共聚物的共聚单体为环氧丙烷、环氧丁烷和/或环氧异丁烷。适宜的实例为环氧乙烷和环氧丙烷的共聚物、环氧乙烷和环氧丁烷的共聚物、及环氧乙烷、环氧丙烷和至少一种环氧丁烷的共聚物。在共聚物中环氧乙烷的含量优选为40-99mol%,环氧丙烷的含量为1-60mol%,而在共聚物中环氧丁烷的含量为1-30mol%。除了直链的还可以使用支化均聚物或共聚物作为接枝基体。
而且可以形成这样的聚合物,其中至少一个,优选1-8个,特别优选1-5个存在于多元醇中的羟基基体可以醚键形式与式I中所示的下列聚醚残基P相连:
n=1-8
聚合物中的烯化氧单元可无规分布或以嵌段形式存在。
但是,也可以使用分子量为1500-25,000的聚环氧烷和脂族C1-C12-,优选C1-C6-二羧酸或芳族二羧酸如草酸、琥珀酸、己二酸或对苯二甲酸的聚酯作为接枝基体,如EP-A-0 743 962所述。
另外可以使用由光气化作用制备的聚环氧烷的聚碳酸酯、或者聚环氧烷与脂族C1-C12-,优选C1-C6-二异氰酸酯或芳族二异氰酸酯如六亚甲基二异氰酸酯或亚苯基二异氰酸酯的聚氨酯作为接枝基体。
上述聚酯、聚碳酸酯或聚氨酯可包含最多500,优选最多100个聚环氧烷单元,聚环氧烷单元可以由各种烯化氧的均聚物和共聚物组成。
优选制备的聚合物是通过使用自由基引发剂体系在b)存在下聚合a)和c)而得到的:
a)脂族C1-C24-羧酸的至少一种乙烯基酯
b)在室温为固态且具有通式I的聚醚
c)视需要存在的另一种单体
其中使用液态聚亚烷基二醇作为自由基引发剂体系的溶剂。
通式I中各变量彼此独立地具有下列含义:
R1氢、C1-C24-烷基、R9-C(=O)-、多元醇残基;
R8氢、C1-C24-烷基、R9-C(=O)-;
R2-R7-(CH2)2-、-(CH2)3-、-(CH2)4-、-CH2-CH(CH3)-、-CH2-CH(CH2-CH3)-、-CH2-CHOR10-CH2-;
R9 C1-C24-烷基;
R10氢、C1-C24-烷基、R9-C(=O)-;
n 1-8;
s 0;
u 1-5000;
v 0-5000;
w 0-5000。
特别优选制备的聚合物是通过使用自由基引发剂体系在b)存在下聚合a)和c)而得到的:
a)脂族C1-C12-羧酸的至少一种乙烯基酯
b)在室温为固态且具有通式I的平均分子量大于1000的聚醚
c)视需要存在的另一种单体
其中使用液态聚亚烷基二醇作为自由基引发剂体系的溶剂,
式I中各变量彼此独立地具有下列含义:
R1氢、C1-C12-烷基、多元醇残基;
R8氢、C1-C12-烷基;
R2-R7-(CH2)2-、-(CH2)3-、-(CH2)4-、-CH2-CH(CH3)-、-CH2-CH(CH2-CH3)-、-CH2-CHOR10-CH2-;
R10氢、C1-C12-烷基;
n 1-5;
s 0;
u 2-2000;
v 0-2000;
w 0-2000。
特别优选制备的聚合物为:
其中使用自由基引发剂体系,在室温时为固态且具有通式I的平均分子量大于1000、优选为1000-15,000的聚醚存在下,使脂族C1-C6-羧酸的至少一种乙烯基酯、特别是乙酸乙烯酯与视需要存在的另一种单体反应而得到者,其中使用液态聚亚烷基二醇作为自由基引发剂体系的溶剂,其中各变量彼此独立地具有下列含义:
R1、R8氢、C1-C6-烷基,特别为氢;
R2-R7-(CH2)2-、-(CH2)3-、-CH2-CH(CH3)-、-CH2-CHOR10-CH2-,特别为-(CH2)2-;
R10氢、C1-C6-烷基;
n 1;
s 0;
u 5-500;
v 0-500,特别为0;
w 0-500,特别为0。
但是,还可以使用室温时为固态的硅酮衍生物作为聚醚。
这种含聚醚的硅酮衍生物的优选代表为包含下列结构单元者:
其中:
R10=CH3 or R9
R11=H,CH3,
R13为含有1-40个碳原子并且可包含氨基、羧基或磺酸酯基团的有机基团,或者在e=0的情况下也可为无机酸的阴离子,
并且其中R8基团可以相同或不同、且每个可衍生自含有1-20个碳原子的脂族烃,含有3-20个碳原子的脂环烃,在性质上是芳香的或等同于R12,其中:
条件是基团R8、R9或R10中至少一个为符合上述定义的含聚环氧烷的基团,
并且f为1-6的整数,
a和b为使聚硅酮嵌段的分子量为300-30,000的整数,
c和d可为0-50的整数,条件是c和d的总和大于0,并且e为0或1。
优选的基团R9和R12为其中c+d的总和为5-30者。
R8基团优选选自下列基团:甲基、乙基、丙基、丁基、异丁基、戊基、异戊基、己基、辛基、癸基、十二烷基和十八烷基,环脂族基团,特别是环己基,芳族基团,特别是苯基或萘基,混合的芳族-脂族基团如苄基或苯基乙基、以及甲苯基和二甲苯基及R12。
特别适宜的R11基团为其中在R11=-(CO)e-R13的情况下,R13为含有1-40个碳原子并且可带有可进一步离子化基团如NH2、COOH、SO3H的任意烷基、环烷基或芳基基团的那些。
在e=0的情况下优选的无机R13基团为磷酸酯和硫酸酯。
特别优选的含聚醚硅酮衍生物为具有下列一般结构者:
还可以使用含聚环氧烷的烯属不饱和单体如聚环氧烷(甲基)丙烯酸酯、聚环氧烷乙烯基醚、聚环氧烷(甲基)丙烯酰胺、聚环氧烷烯丙基酰胺或聚环氧烷乙烯基酰胺的均聚物和共聚物作为聚醚(b)。当然也可以使用这类单体与其它烯属不饱和单体的共聚物。
但是,聚乙烯亚胺与烯化氧的反应产物也可用作含聚醚化合物b)。在这种情况中使用的烯化氧优选为环氧乙烷、环氧丙烷、环氧丁烷及其混合物,特别优选环氧乙烷。可以使用的聚乙烯亚胺为数均分子量为300-20,000,优选500-10,000,非常特别优选500-5000的聚合物。所用烯化氧与聚乙烯亚胺的重量比为100∶1-0.1∶1,优选为50∶1-0.5∶1,非常特别优选为20∶1-0.5∶1。
可提及下列可共聚单体作为在式I聚醚存在下进行聚合的组分a):
脂族饱和或不饱和C1-C24-羧酸如甲酸、乙酸、丙酸、丁酸、戊酸、异戊酸、己酸、辛酸、癸酸、十一碳烯酸、月桂酸、肉豆蔻酸、棕榈酸、棕榈油酸、硬脂酸、油酸、花生酸、山萮酸、二十四酸、蜡酸和蜂花酸的乙烯基酯。
上述C1-C12-羧酸的乙烯基酯是优选使用的,特别是C1-C6-羧酸的乙烯基酯,非常特别优选乙酸乙烯酯。
当然也可以接枝共聚来自a)的各单体的混合物。
乙烯基酯(a)也可以与含有一种或多种烯属不饱和可共聚共聚单体(c)的混合物使用,在这种情况下这些另外的单体的含量应该严格限制在最多为50wt%。0-20wt%的含量是优选的。术语烯属不饱和单体是指含有至少一个可自由基聚合的碳-碳双键并且可以被一、二、三或四取代的单体。
可另外使用的优选烯属不饱和共聚单体(c)可由下列通式描述:
X-C(O)CR15=CHR14
其中
X选自基团-OH,-OM,-OR16,NH2,-NHR16,N(R16)2;
M为选自Na+,K+,Mg++,Ca++,Zn++,NH4 +,烷基铵、二烷基铵、三烷基铵和四烷基铵的阳离子;
R16基团可以是相同或不同的并且选自-H、线性或支链C1-C40-烷基基团、N,N-二甲氨基乙基、2-羟乙基、2-甲氧基乙基、2-乙氧基乙基、羟丙基、甲氧基丙基或乙氧基丙基。
R15和R14彼此独立地选自-H、线性或支链C1-C8-烷基链、甲氧基、乙氧基、2-羟基乙氧基、2-甲氧基乙氧基和2-乙氧基乙基。
适宜单体(c)的代表性而非限制性实例为例如丙烯酸或甲基丙烯酸及其盐、酯和酰胺。盐可衍生自任意无毒金属、铵或取代的铵平衡离子。
酯可衍生自线性C1-C40-、支链C3-C40-或碳环C3-C40-醇,衍生自含有2-约8个羟基基团的多元醇如乙二醇、己二醇、甘油和1,2,6-己三醇,衍生自氨基醇或衍生自醇醚如甲氧基乙醇和乙氧基乙醇、(烷基)聚乙二醇、(烷基)聚丙二醇或乙氧基化脂肪醇,例如与1-200个环氧乙烷单元反应的C12-C24-脂肪醇。
同样适宜的为通式(III)的和甲基丙烯酸的丙烯酸N,N-二烷基氨基烷基酯及N,N-二烷基氨基烷基丙烯酰胺和-甲基丙烯酰胺:
R17=H、含有1-8个碳原子的烷基,
R18=H、甲基,
R19=含有1-24个碳原子的亚烷基,任选可被烷基取代,
R20,R21=C1-C40-烷基基团,
Z=g=1时为氮或g=0时为氧。
酰胺可以是未取代的、N-烷基或N-烷基氨基单取代的或N,N-二烷基取代或N,N-二烷基氨基二取代的,其中烷基或烷基氨基衍生自线性C1-C40-、支链C3-C40-或碳环C3-C40-单元。烷基氨基基团可被另外季铵化。
优选的式III的共聚单体为N,N-二甲基氨基甲基(甲基)丙烯酸酯、N,N-二乙基氨基甲基(甲基)丙烯酸酯、N,N-二甲基氨基乙基(甲基)丙烯酸酯、N,N-二乙基氨基乙基(甲基)丙烯酸酯、N-[3-(二甲基氨基)丙基]甲基丙烯酰胺和N-[3-(二甲基氨基)丙基]丙烯酰胺。
可同样使用的共聚单体(c)为取代的丙烯酸及其盐、酯和酰胺,取代基位于处在丙烯酸二或三位置上的碳原子上,并且彼此独立地选自C1-C4-烷基、-CN、COOH,特别优选甲基丙烯酸、乙基丙烯酸和3-氰基丙烯酸。这些取代丙烯酸的盐、酯和酰胺可如上述丙烯酸的盐、酯和酰胺选择。
其它适宜的共聚单体(c)为线性C1-C40、支链C3-C40或碳环C3-C40羧酸的烯丙基酯,乙烯基或烯丙基卤化物,优选乙烯基氯和烯丙基氯,乙烯基醚,优选甲基、乙基、丁基或十二烷基乙烯基醚,乙烯基甲酰胺、乙烯基甲基乙酰胺,乙烯基胺,乙烯基内酰胺,优选乙烯基吡咯烷酮和乙烯基己内酰胺,乙烯基或烯丙基取代的杂环化合物,优选乙烯基吡啶、乙烯基噁唑啉和烯丙基吡啶。
同样适宜的为通式IV的N-乙烯基咪唑,其中R22-R24彼此独立地为氢、C1-C4-烷基或苯基:
其它适宜的共聚单体(c)为通式(V)的二烯丙基胺
R25=C1-C24-烷基。
另外的适宜共聚单体(c)为偏二氯乙烯;以及含有至少一个碳-碳双键的烃,优选苯乙烯、α-甲基苯乙烯、叔丁基苯乙烯、丁二烯、异戊二烯、环己二烯、乙烯、丙烯、1-丁烯、2-丁烯、异丁烯、乙烯基甲苯、及这些单体的混合物。
特别适宜的共聚单体(c)为丙烯酸、甲基丙烯酸、乙基丙烯酸、丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸2-乙基己酯、丙烯酸癸酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸丙酯、甲基丙烯酸正丁酯、甲基丙烯酸异丁酯、甲基丙烯酸叔丁酯、甲基丙烯酸2-乙基己酯、甲基丙烯酸癸酯、乙基丙烯酸甲酯、乙基丙烯酸乙酯、乙基丙烯酸正丁酯、乙基丙烯酸异丁酯、乙基丙烯酸叔丁酯、乙基丙烯酸2-乙基己酯、乙基丙烯酸癸酯、(甲基)丙烯酸硬脂酯、丙烯酸2,3-二羟基丙基酯、甲基丙烯酸2,3-二羟基丙基酯、丙烯酸2-羟基乙基酯、丙烯酸羟丙酯、甲基丙烯酸2-羟基乙基酯、乙基丙烯酸2-羟基乙基酯、丙烯酸2-甲氧基乙基酯、甲基丙烯酸2-甲氧基乙基酯、乙基丙烯酸2-甲氧基乙基酯、甲基丙烯酸2-乙氧基乙基酯、乙基丙烯酸2-乙氧基乙基酯、甲基丙烯酸羟丙酯、单丙烯酸甘油酯、单甲基丙烯酸甘油酯、聚亚烷基二醇(甲基)丙烯酸酯、不饱和磺酸如丙烯酰氨基丙磺酸;
丙烯酰胺、甲基丙烯酰胺、乙基丙烯酰胺、N-甲基丙烯酰胺、N,N-二甲基丙烯酰胺、N-乙基丙烯酰胺、N-异丙基丙烯酰胺、N-丁基丙烯酰胺、N-叔丁基丙烯酰胺、N-辛基丙烯酰胺、N-叔辛基丙烯酰胺、N-十八烷基丙烯酰胺、N-苯基丙烯酰胺、N-甲基甲基丙烯酰胺、N-乙基甲基丙烯酰胺、N-十二烷基甲基丙烯酰胺、1-乙烯基咪唑、1-乙烯基-2-甲基乙烯基咪唑、(甲基)丙烯酸N,N-二甲氨基甲基酯、(甲基)丙烯酸N,N-二乙氨基甲基酯、(甲基)丙烯酸N,N-二甲氨基乙基酯、(甲基)丙烯酸N,N-二乙氨基乙基酯、(甲基)丙烯酸N,N-二甲氨基丁基酯、(甲基)丙烯酸N,N-二乙氨基丁基酯、(甲基)丙烯酸N,N-二甲氨基己基酯、(甲基)丙烯酸N,N-二甲氨基辛基酯、(甲基)丙烯酸N,N-二甲氨基十二烷基酯、N-[3-(二甲氨基)丙基]甲基丙烯酰胺、N-[3-(二甲氨基)丙基]丙烯酰胺、N-[3-(二甲氨基)丁基]甲基丙烯酰胺、N-[8-(二甲氨基)辛基]甲基丙烯酰胺、N-[12-(二甲氨基)十二烷基]甲基丙烯酰胺、N-[3-(二乙氨基)丙基]甲基丙烯酰胺、N-[3-(二乙氨基)丙基]丙烯酰胺;
马来酸、富马酸、马来酸酐及其单酯、巴豆酸、衣糠酸、二烯丙基二甲基氯化铵、乙烯基醚(例如:甲基、乙基、丁基或十二烷基乙烯基醚)、乙烯基甲酰胺、乙烯基甲基乙酰胺、乙烯基胺;甲基乙烯基酮、马来酰亚胺、乙烯基吡啶、乙烯基咪唑、乙烯基呋喃、苯乙烯、苯乙烯磺酸酯、烯丙基醇、及其混合物。
其中特别优选丙烯酸、甲基丙烯酸、马来酸、富马酸、巴豆酸、马来酸酐及其单酯、丙烯酸甲酯、甲基丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸正丁酯、甲基丙烯酸正丁酯、丙烯酸叔丁酯、甲基丙烯酸叔丁酯、丙烯酸异丁酯、甲基丙烯酸异丁酯、丙烯酸2-乙基己酯、丙烯酸硬脂酯、甲基丙烯酸硬脂酯、N-叔丁基丙烯酰胺、N-辛基丙烯酰胺、2-羟乙基丙烯酸酯、丙烯酸羟丙酯、甲基丙烯酸2-羟乙基酯、甲基丙烯酸羟丙酯、(甲基)丙烯酸亚烷基二醇酯、苯乙烯、不饱和磺酸如丙烯酰氨基丙磺酸、乙烯基吡咯烷酮、乙烯基己内酰胺、乙烯基醚(例如:甲基、乙基、丁基或十二烷基乙烯基醚)、乙烯基甲酰胺、乙烯基甲基乙酰胺、乙烯基胺、1-乙烯基咪唑、1-乙烯基-2-甲基乙烯基咪唑、甲基丙烯酸N,N-二甲氨基甲基酯和N-[3-(二甲氨基)丙基]甲基丙烯酰胺;3-甲基-1-乙烯基咪唑氯化物、3-甲基-1-乙烯基咪唑硫酸甲酯、甲基丙烯酸N,N-二甲氨基乙基酯、被氯甲烷、硫酸甲酯或硫酸二乙酯季铵化的N-[3-(二甲氨基)丙基]甲基丙烯酰胺。
带有一个碱性氮原子的单体还可以下列方式被季铵化:
适于季铵化的胺为例如烷基基团中含有1-24个碳原子的烷基卤化物,例如氯甲烷、溴甲烷、碘甲烷、氯乙烷、溴乙烷、氯丙烷、氯己烷、氯十二烷、月桂基氯和苄基卤化物,特别是苄基氯和苄基溴。另外适宜的季铵化试剂为硫酸二烷基酯,特别是硫酸二甲酯或硫酸二乙酯。碱性胺的季铵化也可用烯化氧如环氧乙烷或环氧丙烷在酸存在下进行。优选的季铵化试剂为:氯甲烷、硫酸二甲酯或硫酸二乙酯。
季铵化反应可在聚合之前或聚合之后进行。
另外,可以使用不饱和酸如丙烯酸或甲基丙烯酸与通式(VI)的季铵化的环氧氯丙烷的反应产物(R26=C1-C40-烷基)。
其实例为例如:
(甲基)丙烯酰氧基羟基丙基三甲基氯化铵和(甲基)丙烯酰氧基羟基丙基三乙基氯化铵。
碱性单体也可通过用无机酸如硫酸、盐酸、氢溴酸、氢碘酸、磷酸或硝酸或者用有机酸如甲酸、乙酸、乳酸或柠檬酸中和而被阳离子化。
除了上述共聚单体,还可以使用所谓的大分子单体如带有一个或多个可自由基聚合基团的含硅大分子单体、或在例如EP 408 311中所述的烷基噁唑啉大分子单体作为共聚单体(c)。
还可以在具有交联作用或对分子量具有调节作用的化合物中使用例如EP 558423中所述的含氟单体,可联合使用或单独使用。
可以使用的调节剂是技术人员已知的常规化合物,例如硫化合物(例如:巯基乙醇、2-乙基己基巯基乙酸、巯基乙酸或十二烷基硫醇)、和三溴氯甲烷或其它对所得聚合物分子量具有调节作用的化合物。
适当时还可以使用含硫羟的硅酮化合物。
优选使用不含硅酮的调节剂。
可以使用的交联单体为带有至少两个烯属双键的化合物,例如烯属不饱和羧酸如丙烯酸或甲基丙烯酸与多元醇的酯、至少双羟基醇的醚如乙烯基醚或烯丙基醚。同样适宜的为带有至少两个双键的直链或支链、线性或环状的脂族或芳族烃,在脂族烃的情况下双键不能是共轭的。同样适宜的为丙烯酸和甲基丙烯酸的酰胺及至少双官能团胺的N-烯丙基胺,例如1,2-二氨基乙烷、1,3-二氨基丙烷。同样适宜的为三烯丙基胺或相应的铵盐、脲衍生物的N-乙烯基化合物、至少双官能团酰胺、氰脲酸酯或氨基甲酸酯。其它适宜的交联剂为二乙烯基二噁烷、四烯丙基硅烷或四乙烯基硅烷。
特别优选的交联剂实例为亚甲基双丙烯酰胺、三烯丙基胺和三烯丙基铵盐、二乙烯基咪唑、N,N’-二乙烯基亚乙基脲、多元醇与丙烯酸或甲基丙烯酸的反应产物、聚环氧烷或已与环氧乙烷和/或环氧丙烷和/或环氧氯丙烷反应的多元醇的甲基丙烯酸酯和丙烯酸酯。
其它适宜者为无机化合物如硼酸或硼酸盐,例如偏硼酸钠、硼砂(四硼酸二钠),及多电荷阳离子盐,例如铜(II)盐如乙酸铜(II)或锌、铝、钛盐。
硼酸和硼酸盐如偏硼酸钠或四硼酸二钠优选适于后继的交联。在这种情况下,可以将硼酸或硼酸盐,优选以盐溶液加入到新聚合物的溶液中。优选将硼酸或硼酸盐加入到聚合物的水溶液中。
可在制备聚合物溶液后立即将硼酸或硼酸盐加入。但是,也可以将硼酸或硼酸盐随后加入到含有新聚合物的化妆品配制剂中或在生产化妆品配制剂的过程中加入。以新聚合物为基准,硼酸或硼酸盐的含量为0-15wt%,优选为0-10wt%特别优选为0-5wt%。
适当时其它聚合物如聚酰胺、聚氨酯、聚酯、烯属不饱和单体的均聚物和共聚物也可以存在于制备新聚合物的聚合过程中。这些聚合物有些也用于化妆品,其实例为以下列注册商标已知的聚合物:AmerholdTM,UltraholdTM,Ultrahold StrongTM,LuviflexTM VBM,LuvimerTM,AcronalTM,AcudyneTM,StepanholdTM,LovocrylTM,VersatylTM,AmphomerTM或Eastma AQTM。
如果新共聚单体(c)包含可电离基团,则它们可以在聚合前或后用酸或碱进行部分或全部中和,以便以例如这种方式将在水中的溶解性和分散性调节至所要求的程度。
可用于中和带有酸性基团单体的试剂为例如无机碱如碳酸钠、碱金属氢氧化物和氨、有机碱如氨基醇,特别是2-氨基-2-甲基-1-丙醇、单乙醇胺、二乙醇胺、三乙醇胺、三异丙醇胺、三(2-羟基-1-丙基)胺、2-氨基-2-甲基1,3-丙二醇、2-氨基-2-羟甲基1,3-丙二醇、以及二胺如赖氨酸。
聚合物的K值应该为10-300,优选为15-150,特别优选为15-100,非常特别优选为20-80。每种情况下所要求的K值可以本身已知的方式由起始原料的组成调节。根据K值的范围,K值可由Fikentscher,Cellulosechemie,13卷,58-64页和71-74页(1932)的方法在N-甲基吡咯烷酮或其它溶剂中于25℃下和聚合物浓度为0.1-5wt%时测定。在交联的例如不溶聚合物的情况下叙述K值是无意义的。
用作接枝基体的聚醚与所用乙烯基酯的用量比为1∶0.5-1∶50,优选为1∶1.5-1∶35,特别优选为1∶2-1∶30。
适宜且优选的聚合引发剂为有机过氧化物如过氧化二乙酰、过氧化二苯甲酰、过氧化琥珀酰、二叔丁基过氧化物、过苯甲酸叔丁酯、过新戊酸叔丁酯、过辛酸叔丁酯、过马来酸叔丁酯、枯烯氢过氧化物、过二碳酸二异丙酯、双(邻甲苯基)过氧化物、过氧化二癸酰、过氧化二辛酰、过氧化二月桂酰、过异丁酸叔丁酯、过乙酸叔丁酯、二叔戊基过氧化物、叔丁基氢过氧化物及所述引发剂的混合物、氧化还原引发剂和偶氮引发剂(例如偶氮二异丁腈、偶氮二(2-脒基丙烷)二盐酸盐或2,2’-偶氮二(2-甲基丁腈))。
以所用单体为基准所用引发剂或引发剂混合物的量为0.01-10wt%,优选为0.1-5wt%。
聚合发生在40-200℃,优选50-140℃,特别优选60-110℃。通常在大气压下进行但也可在减压或高压下进行,优选为1-10巴。
为了提高本发明所用聚合物的亲水性,酯基团可在聚合后被水解或部分水解。水解以本身已知的方式通过在10-80℃,优选20-70℃加入甲醇钠或氢氧化钾溶液而进行。水解度依赖于所用碱的量、水解温度和水解时间。
因此聚乙烯基酯基团的水解度可以为0-100%。优选为20-100%,特别优选为40-100%,尤其为65-100%且非常特别优选为80-100%。
所得水性聚合物分散液或溶液的固含量一般为10-70wt%,优选为15-65wt%,特别优选为20-60wt%。
根据本发明所用聚合物的水解度和浓度得到水性分散液或溶液。
聚合物分散液或溶液可以通过各种干燥方法如喷雾干燥、流化喷雾干燥、鼓式干燥或冷冻干燥法转化为粉末形式。水性分散液或溶液可通过将以这种方式获得的干燥聚合物粉末重新分散在水中而重新制备。转化成粉末形式的优点是提高了储存性、运输更容易并且受微生物进攻的倾向减小。
新型水溶性或水分散性含聚环氧烷或聚甘油的聚合物特别适于作为药物配剂的胃溶性或胃分散性成膜剂或粘合剂、润湿赋形剂和/或增溶剂以及作为化妆品、皮肤病或卫生保健制剂的添加剂。
本发明进一步涉及包含该新型聚合物的化妆品、皮肤病、卫生保健和/或药物组合物。
下列实施例旨在更详细地说明该新制备方法:
实施例1
预进料500g Pluriol E 6000
进料1 900g乙酸乙烯酯
进料2 8.5g过辛酸叔丁酯
100g Pluriol E 600
设备
带有锚式搅拌器、2个可控进料容器、氮夹套管、1个内置式温度计(底部)、外部温度计(外浴温度测量)及控制过程温度的控制体系的6 l JUVO容器。
步骤
用9巴氮气将预进料加压3次。在1巴氮气下以60rpm搅拌预进料并加热至内温为88℃。预进料达到88℃后,在5小时内分别加入进料1和进料2。料加完后在88℃聚合3小时。
然后缓慢加入约2500g去离子水。随后在实验期间通过剧烈引入氮气(“吹扫”)将约400ml容器内物料,特别是水及适当时单体乙酸乙烯酯除去。
固含量41.6%
K值17.8(以去离子水中浓度为1%的溶液测定)
实施例2
预进料51.0g Pluriol E 6000
进料1 340.0g乙酸乙烯酯
进料2 1.36g过辛酸叔丁酯
9.0g Pluriol E 600
进料3 400g甲醇
进料4 4.08g氢氧化钠
36.72g甲醇
进料5 6.66g柠檬酸
659.2g去离子水
固含量19.8%
K值71.1(以N-甲基吡咯烷酮中浓度为1%的溶液测定)
设备
带有锚式搅拌器、回流冷凝管、2个可控进料容器、氮夹套、2个内置式温度计(顶部和底部)、外部温度计及控制过程温度的控制体系的2 l Pilot搅拌设备。
步骤
在温和的氮气流下以150rpm搅拌预进料并加热至外温为90℃。聚乙二醇完全熔融后,分别加入10wt%的进料1和进料2并使实验进行部分聚合30分钟。随后在3.5小时内分别加入剩余的进料1和进料2。加完料后聚合3小时。
然后将混合物冷却至60℃,搅拌下加入进料3。当实验设备冷却到30℃以下后,搅拌下加入进料4。约3-10分钟后,进行水解直至产物变成固态(必要的话关闭搅拌器)。加入进料4约30分钟后,加入进料5并将实验设备加热至外温为85℃。加热期间再次打开搅拌器。产物完全溶解后,通过蒸汽蒸馏除去甲醇(及所产生的乙酸甲酯)。
Pluriol E 6000薄片形式的(平均)分子量为6000的聚乙二醇
Pluriol E 600 室温下为液态的(平均)分子量为600的聚乙二醇
实施例3
普萘洛尔盐酸涂膜片剂(肠溶衣)的制备
通过在卧式转鼓涂布机(Accela-Cota 24″,来自Manesty)中喷涂下列组合物来将含有40mg普萘洛尔盐酸(来自Knoll AG)、195.0mg Ludipress(来自BASF Aktiengesellschaft)、12.50mgKollidon VA 64(来自BASF AG)和2.50mg硬脂酸镁的9mm双面凸片芯涂膜:
来自实施例2的接枝共聚物PEG 6000/VAc | 10.0wt% |
Sicovit红(来自BASF Aktiengesellschaft) | 1.5wt% |
二氧化钛BN 56(来自Kronos) | 3.0wt% |
滑石粉(来自Riedel de Haen) | 4.5wt% |
水 | 81.0wt% |
为了制备喷雾分散体,将接枝共聚物溶解在水中,并在加入Sicovit红、二氧化钛和滑石粉后,在金刚砂盘式磨中均匀化。在进气温度60℃下用1.0mm宽喷嘴以30g/min的喷涂速率和1.5巴喷涂压力将1260g(包括以防喷涂损失而过量的10%)施涂在5000g芯上。喷涂后在60℃干燥5分钟。
得到具有下列性能的非常光滑、有光泽的涂布了红膜的药片:
外观: 非常光滑表面
崩解(模拟胃液): 5min.11s.
崩解时间差(涂膜片-芯):42s.
硬度: 94N
硬度差(涂膜片-芯): 25N
对比例
与实施例3类似,使用Pharmacoat606(羟丙基甲基纤维素,来自Shin-etsu)替代接枝共聚物,并按制造商的说明建议加入1.0wt%的聚乙二醇6000(Lutrol 6000,BASF Aktiengesell chaft)。
得到下列片剂性能:
外观: 稍粗糙表面,模糊印痕
崩解(模拟胃液): 11min.12s.
崩解时间差(涂膜片-芯): 6min.43s.
硬度: 87N
硬度差(涂膜片-芯): 18N
实施例4
作为格列本脲片中粘合剂的应用
将890g磷酸氢钙(来自Rhone Poulenc)和30g格列本脲(来自Arzneimittelwerk Dresden)经0.8mm筛网过筛并在Turbula混炼机(来自Bachofen)中混合5分钟。在Stephan混炼机(来自Stephan)中搅拌下用119g 25wt%的PEG 6000/VAc接枝共聚物(实施例2所制备)的水性制剂缓慢润湿该粉末混合物。为进行完全润湿随后加入粘合剂制剂在800rpm下再搅拌2分钟。然后将润湿的组合物过0.8mm筛网并在25℃的盘中干燥20h。随后加入45g Kollidon CL(来自BASF)和5g硬脂酸镁(来自Brlocher)也在Turbula混炼机中最后混合5分钟。然后在Korsch PH 106旋转式压机(来自Korsch)中于10kN和18kN压力下压制该片剂混合物得到直径为12mm总重量为500mg的双平面斜面药片。
性能: 10kN压力 18kN压力
硬度: 29N 55N
易碎性: 0.6% 0%
崩解: 31s. 41s.
对比例
与实施例4类似进行制备但使用羟丙基甲基纤维素(Pharmacoat 603,来自Shin-etsu)作为粘合剂,由于粘度原因必须将溶液中粘合剂浓度降低到20wt%。
性能: 10kN压力 18kN压力
硬度: 16N 40N
易碎性: 8.0% 0.6%
崩解: 35s. 58s.
实施例5
作为生产超音速凝胶赋形剂的应用
在50℃将5g对羟基苯甲酸甲酯溶解在724g软化水中。随后搅拌下引入6g聚丙烯酸(Carbopol 940,来自Goodrich)和15g PEG6000/VAc接枝共聚物(实施例2)。然后加入200g软化水和50g浓度为4%的氢氧化钠水溶液,搅拌15分钟,注意不要引入空气。这样生产出具有非常舒适皮肤感觉和良好接触性能的凝胶。
实施例6
作为消毒喷雾剂中成膜剂的应用
将150g PEG 6000/VAc接枝共聚物(实施例2)溶解在375软化水中,并加入375g乙醇。然后搅拌下将100g聚乙烯基吡咯烷酮/碘(PVP-Jod 30/06,BASF Aktiengesellschaft)溶解在该聚合物溶液中,并用该制剂装满泵喷瓶。消毒喷雾剂在皮肤上显示了非常良好的成膜性并且在应力条件(52℃7天)下储存后碘不损失。
Claims (7)
2.权利要求1所要求的方法,其中自由基引发剂体系溶液是在贯穿聚合反应时间内连续加入的。
3.权利要求1或2所要求的方法,其中使用液态聚乙二醇作为室温下自由基引发剂的溶剂。
4.由权利要求1-3中任何一项所要求的方法制备的聚合物在药物配剂中作为涂布剂、粘合剂和/或成膜赋形剂的应用。
5.由权利要求1-3中任何一项所要求的方法制备的聚合物作为化妆品、卫生保健和/或皮肤病制剂中添加剂的应用。
6.除常规赋形剂外还包含至少一种由权利要求1-3中任何一项所要求的方法制备的聚合物的化妆品、皮肤病、卫生保健或药物配剂。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10005942.2 | 2000-02-09 | ||
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 (2)
Publication Number | Publication Date |
---|---|
CN1308091A CN1308091A (zh) | 2001-08-15 |
CN1171920C true CN1171920C (zh) | 2004-10-20 |
Family
ID=7630483
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB011034246A Expired - Lifetime 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 |
Country Status (5)
Country | Link |
---|---|
US (1) | US7465440B2 (zh) |
EP (1) | EP1125954B1 (zh) |
JP (1) | JP2001261754A (zh) |
CN (1) | CN1171920C (zh) |
DE (2) | DE10005942A1 (zh) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE60103092T2 (de) | 2000-02-10 | 2005-04-28 | Nippon Shokubai Co., Ltd. | Amino-Gruppe enthaltender Polymer (Salz) und dessen Herstellungsverfahren |
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 |
DE10214087B4 (de) * | 2002-03-28 | 2004-05-06 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Wasserlösliche verzweigte Blockcopolymere |
DE102006055473B4 (de) | 2005-12-21 | 2019-05-16 | Basf Se | Verfahren zur Herstellung von Pfropfcopolymeren auf Basis von Polyethern |
BRPI0907432A2 (pt) | 2008-01-22 | 2019-09-24 | Basf Se | peça moldada de polioximetileno revestida, e, processo para produzir peças moldadas de polioximetileno revestidas |
BRPI0908073A2 (pt) * | 2008-02-06 | 2015-08-25 | Basf Se | Moldagem de polioximetileno revestido, processo para a produção de moldagem de polioximetileno revestido, e, composição de moldagem de polioximetileno |
ATE555153T1 (de) * | 2008-02-13 | 2012-05-15 | Basf Se | Beschichtete polyoxymethylene |
CN102573755A (zh) * | 2009-09-18 | 2012-07-11 | 巴斯夫欧洲公司 | 制备具有低水溶性的物质的制剂的方法 |
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 |
FR1222944A (fr) | 1958-04-15 | 1960-06-14 | Hoechst Ag | Polymères greffés et leur procédé de préparation |
DE1077430B (de) * | 1958-04-15 | 1960-03-10 | Hoechst Ag | Verfahren zur Herstellung von Pfropfpolymerisaten von Polyvinylestern |
BE579240A (zh) | 1958-05-31 | |||
US4085168A (en) * | 1971-02-22 | 1978-04-18 | Cpc International Inc. | Chemically joined, phase separated self-cured hydrophilic thermoplastic graft copolymers and their preparation |
US3928255A (en) * | 1971-02-22 | 1975-12-23 | 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 |
EP0866707A1 (en) * | 1995-12-01 | 1998-09-30 | Janssen Pharmaceutica N.V. | Cisapride sustained release |
ES2212633T3 (es) * | 1998-09-30 | 2004-07-16 | Basf Aktiengesellschaft | Empleo de polimeros hidrosolubles o dispersables en agua, que contienen polieter como agente de recubrimiento, aglutinante y/o producto auxiliar formador de pelicula en formas de presentacion farmaceuticas. |
-
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
Also Published As
Publication number | Publication date |
---|---|
DE50114980D1 (de) | 2009-08-27 |
EP1125954B1 (de) | 2009-07-15 |
EP1125954A3 (de) | 2001-10-24 |
JP2001261754A (ja) | 2001-09-26 |
CN1308091A (zh) | 2001-08-15 |
EP1125954A2 (de) | 2001-08-22 |
DE10005942A1 (de) | 2001-08-16 |
US20010018489A1 (en) | 2001-08-30 |
US7465440B2 (en) | 2008-12-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1171920C (zh) | 聚乙烯基酯的接枝共聚物及其制备方法和用途 | |
CN1176956C (zh) | 包含乙烯酯和聚醚的聚合物的硬胶囊、其用途和生产方法 | |
CN1167403C (zh) | 毛发护理剂 | |
CN1061055C (zh) | 热塑弹性共聚物及含该共聚物的护发和护肤组合物 | |
CN1234744C (zh) | 化妆品组合物 | |
CN1334830A (zh) | 亲水性两性聚合物 | |
CN1157426C (zh) | 用于处理角蛋白基质的支化/嵌段共聚物 | |
CN1289548C (zh) | 水溶性聚合物及其制备方法,含有它们的组合物及其美容用途 | |
CN1254229C (zh) | 用于氧化染色角蛋白纤维的组合物 | |
CN1658823A (zh) | 包括至少一种含有(甲基)丙烯酰胺单元的水溶性共聚物的化妆品产品 | |
CN1522686A (zh) | 即用漂白组合物、其制备方法以及漂白方法 | |
CN1259862A (zh) | 含增韧的接枝聚合物的个人护理组合物 | |
CN1189152C (zh) | 美发配方 | |
CN1265021A (zh) | 包含聚硅氧烷的聚合物在化妆品配制剂中的应用 | |
CN1328449A (zh) | 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 | |
CN1213721C (zh) | 化妆品组合物 | |
CN1298746C (zh) | 高官能的聚合物乳液 | |
CN1326732A (zh) | 含有乙烯基酯和聚醚的聚合物的软胶囊,其用途及生产方法 | |
CN1151769C (zh) | 毛发化妆品组合物 | |
CN1890277A (zh) | 两性阴离子共聚物 | |
CN1890278A (zh) | 基于(甲基)丙烯酸叔丁酯的共聚物及其用途 | |
CN1305366A (zh) | 美容产品 | |
CN1157179C (zh) | 包含线形增韧硅氧烷接枝聚合物的个人护理组合物 | |
CN1271989C (zh) | 包含至少一种具有n-乙烯基内酰胺单元的共聚物的化妆品组合物 | |
CN1269377A (zh) | 水溶性或水分散性聚合物盐 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C06 | Publication | ||
PB01 | Publication | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CX01 | Expiry of patent term |
Granted publication date: 20041020 |
|
CX01 | Expiry of patent term |