TWI627188B - 製備界面活性劑敏感性乳化聚合物之方法 - Google Patents
製備界面活性劑敏感性乳化聚合物之方法 Download PDFInfo
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- TWI627188B TWI627188B TW103108118A TW103108118A TWI627188B TW I627188 B TWI627188 B TW I627188B TW 103108118 A TW103108118 A TW 103108118A TW 103108118 A TW103108118 A TW 103108118A TW I627188 B TWI627188 B TW I627188B
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- Prior art keywords
- vinyl
- meth
- group
- acrylate
- monomer
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 99
- 239000004908 Emulsion polymer Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 194
- 229920000642 polymer Polymers 0.000 claims abstract description 177
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 87
- 238000000034 method Methods 0.000 claims abstract description 74
- 239000003945 anionic surfactant Substances 0.000 claims abstract description 36
- 239000002198 insoluble material Substances 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims description 228
- -1 C 6 alkyl hydroperoxides Chemical class 0.000 claims description 132
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 239000003638 chemical reducing agent Substances 0.000 claims description 50
- 239000007800 oxidant agent Substances 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 230000001590 oxidative effect Effects 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- 239000002736 nonionic surfactant Substances 0.000 claims description 26
- 238000004132 cross linking Methods 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 23
- 230000002209 hydrophobic effect Effects 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 20
- 239000002280 amphoteric surfactant Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 19
- 229920000570 polyether Polymers 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 17
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
- 229920001519 homopolymer Polymers 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000012966 redox initiator Substances 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 229920002554 vinyl polymer Polymers 0.000 claims description 13
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 claims description 11
- 235000010350 erythorbic acid Nutrition 0.000 claims description 11
- 239000004318 erythorbic acid Substances 0.000 claims description 11
- 229940026239 isoascorbic acid Drugs 0.000 claims description 11
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 150000002170 ethers Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229920001567 vinyl ester resin Polymers 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 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 claims description 6
- 238000004945 emulsification Methods 0.000 claims description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229920001400 block copolymer Polymers 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
- 125000000913 palmityl 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])[H] 0.000 claims description 5
- DETXZQGDWUJKMO-UHFFFAOYSA-N 2-hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical group C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 235000010323 ascorbic acid Nutrition 0.000 claims description 4
- 229960005070 ascorbic acid Drugs 0.000 claims description 4
- 239000011668 ascorbic acid Substances 0.000 claims description 4
- 125000002511 behenyl 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])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001421 myristyl 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])[H] 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 229920005604 random copolymer Polymers 0.000 claims description 4
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 4
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 4
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- KCHNMIKAMRQBHD-UHFFFAOYSA-N 1-hydroperoxypentane Chemical group CCCCCOO KCHNMIKAMRQBHD-UHFFFAOYSA-N 0.000 claims description 3
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- 239000011149 active material Substances 0.000 claims description 3
- 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 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 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 claims description 3
- 125000005504 styryl group Chemical group 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- RBNPOMFGQQGHHO-UHFFFAOYSA-N -2,3-Dihydroxypropanoic acid Natural products OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 claims description 2
- JHYYINIEKJKMDD-UHFFFAOYSA-N 1-ethenyl-3,3-dimethylpyrrolidin-2-one Chemical compound CC1(C)CCN(C=C)C1=O JHYYINIEKJKMDD-UHFFFAOYSA-N 0.000 claims description 2
- DJABNVJZYFGAJE-UHFFFAOYSA-N 1-ethenyl-5-ethylpyrrolidin-2-one Chemical compound CCC1CCC(=O)N1C=C DJABNVJZYFGAJE-UHFFFAOYSA-N 0.000 claims description 2
- HQGPZXPTJWUDQR-UHFFFAOYSA-N 1-ethenyl-5-methylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C=C HQGPZXPTJWUDQR-UHFFFAOYSA-N 0.000 claims description 2
- FFDNCQYZAAVSSF-UHFFFAOYSA-N 1-ethenyl-6-methylpiperidin-2-one Chemical compound CC1CCCC(=O)N1C=C FFDNCQYZAAVSSF-UHFFFAOYSA-N 0.000 claims description 2
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 claims description 2
- HMPUKFGKTNAIRX-UHFFFAOYSA-N 1-prop-1-en-2-ylpyrrolidin-2-one Chemical compound CC(=C)N1CCCC1=O HMPUKFGKTNAIRX-UHFFFAOYSA-N 0.000 claims description 2
- HVCNQTCZNBPWBV-UHFFFAOYSA-N 2-hydroxy-2-sulfinoacetic acid Chemical compound OC(=O)C(O)S(O)=O HVCNQTCZNBPWBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- MMEXLQDBXCXJEL-UHFFFAOYSA-N S=S=S.[Na+] Chemical compound S=S=S.[Na+] MMEXLQDBXCXJEL-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- KVMGZRHAVFZQQJ-UHFFFAOYSA-N ethenyl 2-methylhexanoate Chemical compound CCCCC(C)C(=O)OC=C KVMGZRHAVFZQQJ-UHFFFAOYSA-N 0.000 claims description 2
- WNMORWGTPVWAIB-UHFFFAOYSA-N ethenyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC=C WNMORWGTPVWAIB-UHFFFAOYSA-N 0.000 claims description 2
- RASNHPFIOGUOOT-UHFFFAOYSA-N ethenyl 6-methylheptanoate Chemical compound CC(C)CCCCC(=O)OC=C RASNHPFIOGUOOT-UHFFFAOYSA-N 0.000 claims description 2
- TVFJAZCVMOXQRK-UHFFFAOYSA-N ethenyl 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC(=O)OC=C TVFJAZCVMOXQRK-UHFFFAOYSA-N 0.000 claims description 2
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 claims description 2
- CMDXMIHZUJPRHG-UHFFFAOYSA-N ethenyl decanoate Chemical class CCCCCCCCCC(=O)OC=C CMDXMIHZUJPRHG-UHFFFAOYSA-N 0.000 claims description 2
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 claims description 2
- UJRIYYLGNDXVTA-UHFFFAOYSA-N ethenyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC=C UJRIYYLGNDXVTA-UHFFFAOYSA-N 0.000 claims description 2
- LZWYWAIOTBEZFN-UHFFFAOYSA-N ethenyl hexanoate Chemical compound CCCCCC(=O)OC=C LZWYWAIOTBEZFN-UHFFFAOYSA-N 0.000 claims description 2
- NWJTZFZQVYJIHU-UHFFFAOYSA-N ethenyl nonanoate Chemical compound CCCCCCCCC(=O)OC=C NWJTZFZQVYJIHU-UHFFFAOYSA-N 0.000 claims description 2
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 claims description 2
- BLZSRIYYOIZLJL-UHFFFAOYSA-N ethenyl pentanoate Chemical compound CCCCC(=O)OC=C BLZSRIYYOIZLJL-UHFFFAOYSA-N 0.000 claims description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- RTXGMZRJRSWDRN-UHFFFAOYSA-N n-ethenyl-n-(hydroxymethyl)acetamide Chemical compound CC(=O)N(CO)C=C RTXGMZRJRSWDRN-UHFFFAOYSA-N 0.000 claims description 2
- MLADWLUEOJQILB-UHFFFAOYSA-N n-ethenyl-n-(hydroxymethyl)formamide Chemical compound OCN(C=C)C=O MLADWLUEOJQILB-UHFFFAOYSA-N 0.000 claims description 2
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 claims description 2
- OFESGEKAXKKFQT-UHFFFAOYSA-N n-ethenyl-n-methylformamide Chemical compound C=CN(C)C=O OFESGEKAXKKFQT-UHFFFAOYSA-N 0.000 claims description 2
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 claims description 2
- VSVCAMGKPRPGQR-UHFFFAOYSA-N propan-2-one;sulfurous acid Chemical compound CC(C)=O.OS(O)=O VSVCAMGKPRPGQR-UHFFFAOYSA-N 0.000 claims description 2
- 235000010265 sodium sulphite Nutrition 0.000 claims description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 claims 1
- GOCCREQJUBABAL-UHFFFAOYSA-N 2,2-dihydroxyacetic acid Chemical compound OC(O)C(O)=O GOCCREQJUBABAL-UHFFFAOYSA-N 0.000 claims 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 claims 1
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 claims 1
- IEPPSWCSPBCKLP-UHFFFAOYSA-N N-ethenyl-9H-fluoren-1-amine Chemical compound C(=C)NC1=CC=CC=2C3=CC=CC=C3CC12 IEPPSWCSPBCKLP-UHFFFAOYSA-N 0.000 claims 1
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 1
- VTYVIFFJJXAHTG-UHFFFAOYSA-M azanium;sodium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [NH4+].[Na+].[O-]S([O-])(=O)=S VTYVIFFJJXAHTG-UHFFFAOYSA-M 0.000 claims 1
- MRIZMKJLUDDMHF-UHFFFAOYSA-N cumene;hydrogen peroxide Chemical group OO.CC(C)C1=CC=CC=C1 MRIZMKJLUDDMHF-UHFFFAOYSA-N 0.000 claims 1
- IGBZOHMCHDADGY-UHFFFAOYSA-N ethenyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC=C IGBZOHMCHDADGY-UHFFFAOYSA-N 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims 1
- XNEFVTBPCXGIRX-UHFFFAOYSA-N methanesulfinic acid Chemical compound CS(O)=O XNEFVTBPCXGIRX-UHFFFAOYSA-N 0.000 claims 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical group C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims 1
- 239000002245 particle Substances 0.000 abstract description 78
- 239000000725 suspension Substances 0.000 abstract description 20
- 230000006641 stabilisation Effects 0.000 abstract description 3
- 238000011105 stabilization Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
- 239000012530 fluid Substances 0.000 description 56
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 38
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 38
- 239000000839 emulsion Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 26
- 125000000129 anionic group Chemical group 0.000 description 25
- 229920001577 copolymer Polymers 0.000 description 22
- 229910052708 sodium Inorganic materials 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- 239000011734 sodium Substances 0.000 description 19
- 229920001223 polyethylene glycol Polymers 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 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 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 14
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- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
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- 125000005702 oxyalkylene group Chemical group 0.000 description 1
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- 238000004806 packaging method and process Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
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- 238000005191 phase separation Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 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
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
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- 229920002006 poly(N-vinylimidazole) polymer Polymers 0.000 description 1
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- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
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- 229920001282 polysaccharide Polymers 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
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- 239000001508 potassium citrate Substances 0.000 description 1
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- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
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- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
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- 239000012429 reaction media Substances 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
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- NKNLXPQRJKBHBZ-UHFFFAOYSA-M sodium;2-phenoxybenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1OC1=CC=CC=C1 NKNLXPQRJKBHBZ-UHFFFAOYSA-M 0.000 description 1
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- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
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- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
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- 125000002889 tridecyl 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])[H] 0.000 description 1
- QTUIJRIDZOSXHJ-UHFFFAOYSA-M tridecyl sulfate Chemical compound CCCCCCCCCCCCCOS([O-])(=O)=O QTUIJRIDZOSXHJ-UHFFFAOYSA-M 0.000 description 1
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- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical class CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
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- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
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- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Chemical class COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/08—Vinyl acetate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/05—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media from solid 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
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F216/125—Monomers containing two or more unsaturated aliphatic radicals, e.g. trimethylolpropane triallyl ether or pentaerythritol triallyl ether
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2331/00—Characterised by the use of copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, or carbonic acid, or of a haloformic acid
- C08J2331/02—Characterised by the use of omopolymers or copolymers of esters of monocarboxylic acids
- C08J2331/04—Homopolymers or copolymers of vinyl acetate
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Cosmetics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Detergent Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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| US201361776055P | 2013-03-11 | 2013-03-11 | |
| US61/776,055 | 2013-03-11 |
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| BR112017012858A2 (pt) * | 2014-12-17 | 2018-01-09 | Lubrizol Advanced Mat Inc | composição, fluidos de perfuração e de fraturamento hidráulico, e, métodos para intensificar sinergicamente a viscosidade e a tensão de escoamento e a viscosidade de uma composição de tensoativo. |
| US11753526B2 (en) * | 2017-03-06 | 2023-09-12 | L. Brüggemann Gmbh & Co. Kg | Synergistically active composition |
| WO2018204812A1 (en) * | 2017-05-04 | 2018-11-08 | Lubrizol Advanced Materials, Inc. | Dual activated microgel |
| KR102642297B1 (ko) * | 2019-09-25 | 2024-02-28 | 주식회사 엘지화학 | 수성 점착제 조성물의 제조 방법 및 이에 의해 제조되는 수성 점착제 조성물 |
| EP4008312A1 (en) * | 2020-12-01 | 2022-06-08 | Calyxia | Emulsion comprising size-controlled droplets |
| FR3125041A1 (fr) * | 2021-07-09 | 2023-01-13 | Snf Sa | Procédé d’obtention de N-vinylformamide biosourcé |
| CN114283966B (zh) * | 2021-12-31 | 2024-11-15 | 西安宏星电子浆料科技股份有限公司 | 有机载体及其方法、导电银浆料及其方法和太阳能电池 |
| CN116942564B (zh) * | 2022-04-18 | 2025-09-23 | 万华化学集团股份有限公司 | 宽pH值透明度的增稠悬浮聚合物、制备方法及含其的清洗剂组合物、制备方法及应用 |
| US12241016B2 (en) | 2022-08-08 | 2025-03-04 | Cnpc Usa Corporation | High temperature high salt low end rheology modifiers |
| CN115532183B (zh) * | 2022-09-27 | 2025-08-26 | 江南大学 | 一种高效的温敏体系的制备与应用 |
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| TW201335294A (zh) * | 2012-01-26 | 2013-09-01 | Lubrizol Advanced Mat Inc | 水分散性可自交聯的預聚物組成物 |
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| DE4212768A1 (de) * | 1992-04-16 | 1993-10-21 | Huels Chemische Werke Ag | Verfahren zur Herstellung von wäßrigen Polymerdispersionen |
| DK0596318T3 (da) * | 1992-11-04 | 1999-06-14 | Nat Starch Chem Invest | Emulsionsbindemidler med lavt indhold af formaldehydrest, og som har forbedret trækstyrke |
| DE4405621A1 (de) * | 1994-02-22 | 1995-08-24 | Basf Ag | Verfahren zur Herstellung von Copolymerisaten aus Vinylestern und monoethylenisch ungesättigten Carbonsäuren und ihre Verwendung |
| AU672159B2 (en) * | 1994-06-14 | 1996-09-19 | National Starch And Chemical Investment Holding Corporation | High performance PVOH stabilised EVA adhesives |
| US5663258A (en) | 1996-02-20 | 1997-09-02 | Isp Investments Inc. | Strongly swellable, moderately crosslinked copolymers of vinylpyrrolidone and vinyl acetate |
| JP3801888B2 (ja) * | 2000-09-04 | 2006-07-26 | 株式会社日本触媒 | ビニルエーテル基含有(メタ)アクリル酸エステル類の製造方法並びにビニルエーテル基ペンダントラジカル重合体および架橋体 |
| US7288616B2 (en) * | 2002-01-18 | 2007-10-30 | Lubrizol Advanced Materials, Inc. | Multi-purpose polymers, methods and compositions |
| JP2004045749A (ja) * | 2002-07-11 | 2004-02-12 | Menicon Co Ltd | 高含水性眼用レンズ及びその製造方法 |
| US7378479B2 (en) * | 2002-09-13 | 2008-05-27 | Lubrizol Advanced Materials, Inc. | Multi-purpose polymers, methods and compositions |
| JP5778889B2 (ja) * | 2006-11-09 | 2015-09-16 | ルブリゾル アドバンスド マテリアルズ, インコーポレイテッド | 刺激緩和ポリマーおよびその使用 |
| DE102007048141A1 (de) | 2007-10-05 | 2009-04-09 | Henkel Ag & Co. Kgaa | Wässrige Dispersion |
| JP6162121B2 (ja) | 2011-09-13 | 2017-07-12 | ルブリゾル アドバンスド マテリアルズ, インコーポレイテッド | 界面活性剤応答性エマルジョン重合ミクロゲル |
| KR101974993B1 (ko) * | 2011-09-13 | 2019-05-03 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 계면활성제 반응성 분산 중합된 마이크로-겔 |
| JP2014534275A (ja) | 2011-09-13 | 2014-12-18 | ルブリゾル アドバンスド マテリアルズ, インコーポレイテッド | 界面活性剤応答性ミクロゲル |
| CN102863594A (zh) * | 2012-09-14 | 2013-01-09 | 苏州飞翔新材料研究院有限公司 | 一种聚合物乳液及其应用 |
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- 2014-03-05 EP EP14713997.6A patent/EP2970537B1/en not_active Not-in-force
- 2014-03-05 BR BR112015022163A patent/BR112015022163A2/pt not_active Application Discontinuation
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| TW201335294A (zh) * | 2012-01-26 | 2013-09-01 | Lubrizol Advanced Mat Inc | 水分散性可自交聯的預聚物組成物 |
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| US10577444B2 (en) | 2020-03-03 |
| US20160017070A1 (en) | 2016-01-21 |
| JP2016521290A (ja) | 2016-07-21 |
| TW201441265A (zh) | 2014-11-01 |
| JP6499637B2 (ja) | 2019-04-10 |
| BR112015022163A2 (pt) | 2017-07-18 |
| AR095214A1 (es) | 2015-09-30 |
| CN105073798A (zh) | 2015-11-18 |
| KR20150128752A (ko) | 2015-11-18 |
| CN105073798B (zh) | 2018-09-25 |
| EP2970537A1 (en) | 2016-01-20 |
| EP2970537B1 (en) | 2017-02-22 |
| WO2014164092A1 (en) | 2014-10-09 |
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