JP5806226B2 - 加水分解に安定な多目的ポリマー - Google Patents
加水分解に安定な多目的ポリマー Download PDFInfo
- Publication number
- JP5806226B2 JP5806226B2 JP2012542148A JP2012542148A JP5806226B2 JP 5806226 B2 JP5806226 B2 JP 5806226B2 JP 2012542148 A JP2012542148 A JP 2012542148A JP 2012542148 A JP2012542148 A JP 2012542148A JP 5806226 B2 JP5806226 B2 JP 5806226B2
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- JP
- Japan
- Prior art keywords
- monomer
- polymer
- polyethoxylated
- acrylate
- methacrylate
- 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.)
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- 229920000642 polymer Polymers 0.000 title claims description 267
- 239000000178 monomer Substances 0.000 claims description 435
- 239000000203 mixture Substances 0.000 claims description 205
- -1 2- (dimethylamino) propan-2-yl methacrylate Chemical compound 0.000 claims description 93
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 73
- 239000000047 product Substances 0.000 claims description 73
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 60
- 229920002554 vinyl polymer Polymers 0.000 claims description 60
- 150000002734 metacrylic acid derivatives Polymers 0.000 claims description 43
- 239000012986 chain transfer agent Substances 0.000 claims description 35
- 229920001296 polysiloxane Polymers 0.000 claims description 34
- 239000003381 stabilizer Substances 0.000 claims description 28
- 239000004094 surface-active agent Substances 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 27
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 238000004132 cross linking Methods 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 16
- 101150065749 Churc1 gene Proteins 0.000 claims description 16
- 102100038239 Protein Churchill Human genes 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 11
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 11
- 229920001400 block copolymer Polymers 0.000 claims description 11
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- VVOKYOKVMKJIMT-UHFFFAOYSA-N [3-(dimethylamino)-2,2-dimethylpropyl] 2-methylprop-2-enoate Chemical compound CN(C)CC(C)(C)COC(=O)C(C)=C VVOKYOKVMKJIMT-UHFFFAOYSA-N 0.000 claims description 9
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 229920005604 random copolymer Polymers 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 8
- VGAJYAOJRBZVNG-UHFFFAOYSA-N [2-(dimethylamino)-2-methylpropyl] 2-methylprop-2-enoate Chemical compound CN(C)C(C)(C)COC(=O)C(C)=C VGAJYAOJRBZVNG-UHFFFAOYSA-N 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- TVFWYUWNQVRQRG-UHFFFAOYSA-N 2,3,4-tris(2-phenylethenyl)phenol Chemical compound C=1C=CC=CC=1C=CC1=C(C=CC=2C=CC=CC=2)C(O)=CC=C1C=CC1=CC=CC=C1 TVFWYUWNQVRQRG-UHFFFAOYSA-N 0.000 claims description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 7
- 125000001204 arachidyl 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])[H] 0.000 claims description 7
- 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 7
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 7
- 239000004359 castor oil Substances 0.000 claims description 7
- 235000019438 castor oil Nutrition 0.000 claims description 7
- 235000012000 cholesterol Nutrition 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 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 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 7
- 230000036541 health Effects 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000002819 montanyl 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])[H] 0.000 claims description 7
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 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 claims description 7
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 claims description 6
- 235000006008 Brassica napus var napus Nutrition 0.000 claims description 6
- 240000000385 Brassica napus var. napus Species 0.000 claims description 6
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 claims description 6
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- DABQKEQFLJIRHU-UHFFFAOYSA-N 2-Propenoic acid, 2-methyl-, 3,3,5-trimethylcyclohexyl ester Chemical compound CC1CC(OC(=O)C(C)=C)CC(C)(C)C1 DABQKEQFLJIRHU-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 239000002562 thickening agent Substances 0.000 claims description 5
- 229920001567 vinyl ester resin Polymers 0.000 claims description 5
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 239000000834 fixative Substances 0.000 claims description 4
- 239000002954 polymerization reaction product Substances 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 238000009792 diffusion process Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000003440 styrenes Chemical class 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 230000002421 anti-septic effect Effects 0.000 claims description 2
- 239000002216 antistatic agent Substances 0.000 claims description 2
- 230000003750 conditioning effect Effects 0.000 claims description 2
- 230000003340 mental effect Effects 0.000 claims description 2
- 230000008447 perception Effects 0.000 claims description 2
- 239000006254 rheological additive Substances 0.000 claims description 2
- 239000000375 suspending agent Substances 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims 2
- 239000003899 bactericide agent Substances 0.000 claims 1
- 239000000022 bacteriostatic agent Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003906 humectant Substances 0.000 claims 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 39
- 238000006116 polymerization reaction Methods 0.000 description 38
- 239000000839 emulsion Substances 0.000 description 33
- 125000005842 heteroatom Chemical group 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 125000004432 carbon atom Chemical group C* 0.000 description 27
- 239000002253 acid Substances 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 23
- 239000000499 gel Substances 0.000 description 22
- 238000000034 method Methods 0.000 description 21
- 238000006460 hydrolysis reaction Methods 0.000 description 20
- 239000004816 latex Substances 0.000 description 19
- 229920000126 latex Polymers 0.000 description 19
- 238000007720 emulsion polymerization reaction Methods 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 230000007062 hydrolysis Effects 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 16
- 229920001577 copolymer Polymers 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 238000012546 transfer Methods 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- 238000003860 storage Methods 0.000 description 14
- 239000003999 initiator Substances 0.000 description 13
- 230000008719 thickening Effects 0.000 description 13
- 239000002736 nonionic surfactant Substances 0.000 description 12
- 229920000151 polyglycol Polymers 0.000 description 12
- 239000010695 polyglycol Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical group C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 239000011324 bead Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 7
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 7
- 125000005907 alkyl ester group Chemical group 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
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- 125000000524 functional group Chemical group 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 6
- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- 239000003945 anionic surfactant Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000002837 carbocyclic group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
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- 230000003301 hydrolyzing effect Effects 0.000 description 6
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- 150000003573 thiols Chemical class 0.000 description 6
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 5
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 5
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- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
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- 238000003756 stirring Methods 0.000 description 5
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- 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 description 4
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
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- 230000009466 transformation Effects 0.000 description 4
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- 229910052719 titanium Inorganic materials 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 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
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- BORISOXJXHFNLS-UHFFFAOYSA-N tris(2-propan-2-yloxyethenyl)silane Chemical compound C(C)(C)OC=C[SiH](C=COC(C)C)C=COC(C)C BORISOXJXHFNLS-UHFFFAOYSA-N 0.000 description 1
- PKRKCDBTXBGLKV-UHFFFAOYSA-N tris(ethenyl)-methylsilane Chemical compound C=C[Si](C)(C=C)C=C PKRKCDBTXBGLKV-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 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
- 239000003643 water by type Substances 0.000 description 1
- 239000007883 water-soluble azo polymerization initiator Substances 0.000 description 1
- 229920003170 water-soluble synthetic polymer Polymers 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
Classifications
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1802—C2-(meth)acrylate, e.g. ethyl (meth)acrylate
-
- 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
- C08F216/14—Monomers containing only one unsaturated aliphatic radical
- C08F216/1416—Monomers containing oxygen in addition to the ether oxygen, e.g. allyl glycidyl ether
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
-
- 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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
-
- 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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/103—Esters of polyhydric alcohols or polyhydric phenols of trialcohols, e.g. trimethylolpropane tri(meth)acrylate
-
- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Cosmetics (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
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|---|---|---|---|
| US26540209P | 2009-12-01 | 2009-12-01 | |
| US61/265,402 | 2009-12-01 | ||
| PCT/US2010/058507 WO2011068837A2 (en) | 2009-12-01 | 2010-12-01 | Hydrolytically stable multi-purpose polymers |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015121345A Division JP2015163721A (ja) | 2009-12-01 | 2015-06-16 | 加水分解に安定な多目的ポリマー |
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| JP2013512330A JP2013512330A (ja) | 2013-04-11 |
| JP2013512330A5 JP2013512330A5 (enExample) | 2014-01-09 |
| JP5806226B2 true JP5806226B2 (ja) | 2015-11-10 |
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| JP2012542148A Expired - Fee Related JP5806226B2 (ja) | 2009-12-01 | 2010-12-01 | 加水分解に安定な多目的ポリマー |
| JP2015121345A Withdrawn JP2015163721A (ja) | 2009-12-01 | 2015-06-16 | 加水分解に安定な多目的ポリマー |
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| JP2015121345A Withdrawn JP2015163721A (ja) | 2009-12-01 | 2015-06-16 | 加水分解に安定な多目的ポリマー |
Country Status (8)
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|---|---|
| US (1) | US9187590B2 (enExample) |
| EP (1) | EP2507275B1 (enExample) |
| JP (2) | JP5806226B2 (enExample) |
| CN (1) | CN102639575B (enExample) |
| AR (1) | AR079232A1 (enExample) |
| BR (1) | BR112012013063B1 (enExample) |
| ES (1) | ES2534193T3 (enExample) |
| WO (1) | WO2011068837A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2011068820A1 (en) * | 2009-12-01 | 2011-06-09 | Lubrizol Advanced Materials, Inc. | Hydrolytically stable multi-purpose polymers |
| JP5278709B2 (ja) * | 2009-12-04 | 2013-09-04 | 株式会社村田製作所 | 導電性樹脂組成物およびチップ型電子部品 |
| WO2012030750A2 (en) † | 2010-09-02 | 2012-03-08 | Lubrizol Advanced Materials, Inc. | Polymers and compositions |
| CN102432748B (zh) * | 2011-07-26 | 2013-11-06 | 北京君伦润众科技有限公司 | 两亲高分子和用途 |
| CN102382242B (zh) * | 2011-07-26 | 2013-10-23 | 北京君伦润众科技有限公司 | 一种两亲高分子及其用途 |
| 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 |
| JP5746240B2 (ja) * | 2013-02-26 | 2015-07-08 | 国立研究開発法人国立循環器病研究センター | 温度応答性ポリマーの製造方法、温度応答性ポリマー、細胞培養器の製造方法、及び細胞培養器 |
| US9291909B2 (en) * | 2013-05-17 | 2016-03-22 | Az Electronic Materials (Luxembourg) S.A.R.L. | Composition comprising a polymeric thermal acid generator and processes thereof |
| US20150191642A1 (en) * | 2014-01-08 | 2015-07-09 | Hercules Incorporated | Cementing fluid and methods for producing the same |
| JP6535192B2 (ja) * | 2015-03-25 | 2019-06-26 | 株式会社日本触媒 | 抗菌剤 |
| US9937118B2 (en) | 2016-06-21 | 2018-04-10 | Johnson & Johnson Consumer Inc. | Clear suspending personal care cleansing compositions |
| US10159638B2 (en) | 2016-06-21 | 2018-12-25 | Johnson & Johnson Consumer Inc. | Personal care compositions containing complexing polyelectrolytes |
| CN106279702A (zh) * | 2016-08-26 | 2017-01-04 | 四川省建筑科学研究院 | 一种消泡型功能单体、聚羧酸减水剂及其制备方法 |
| TW201840635A (zh) * | 2017-01-26 | 2018-11-16 | 美商盧伯利索先進材料有限公司 | 具有改良化學及熱安定性之含有一或二個四級胺錨定基的聚合分散劑 |
| CN108752540B (zh) * | 2018-05-29 | 2020-05-26 | 江苏苏博特新材料股份有限公司 | 一种两亲性多功能杂化纳米粒子、其制备方法及其应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US33156A (en) | 1861-08-27 | Improvement in machinery for ringing fog-bells | ||
| US4384096A (en) | 1979-08-27 | 1983-05-17 | The Dow Chemical Company | Liquid emulsion polymers useful as pH responsive thickeners for aqueous systems |
| US4421902A (en) | 1982-09-30 | 1983-12-20 | Rohm And Haas Company | Alkyl, poly(oxyethylene) poly(carbonyloxyethylene) acrylate emulsion copolymers for thickening purposes |
| US4514552A (en) | 1984-08-23 | 1985-04-30 | Desoto, Inc. | Alkali soluble latex thickeners |
| JPS61204034A (ja) | 1985-03-08 | 1986-09-10 | Kao Corp | 水性分散液 |
| US4600761A (en) | 1985-04-04 | 1986-07-15 | Alco Chemical Corporation | Acrylic emulsion copolymers for thickening aqueous systems and copolymerizable surfactant monomers for use therein |
| US4616074A (en) | 1985-10-01 | 1986-10-07 | Alco Chemical Corporation | Acrylic-methylene succinic ester emulsion copolymers for thickening aqueous systems |
| JPH0711120B2 (ja) * | 1985-12-27 | 1995-02-08 | 花王株式会社 | 製紙用サイズ剤分散液 |
| JPS6461571A (en) * | 1987-08-26 | 1989-03-08 | Kao Corp | Concentration type softening finish agent for clothing |
| US4885102A (en) | 1987-07-17 | 1989-12-05 | Kao Corporation | Cloth-softening liquid composition containing quaternary ammonium compound and a polyether derivative or cationic surfactant polymer |
| DE3924393A1 (de) | 1989-07-24 | 1991-01-31 | Roehm Gmbh | Wasserloeslicher druckempfindlicher hauthaftkleber, dessen verwendung und damit ausgeruestete mittel |
| US5179157A (en) | 1990-01-20 | 1993-01-12 | Synthopol Chemie Dr. Rer. Pol. Koch Gmbh & Co., Kg | Copolymerizate solutions based on addition products of α,β-unsaturated carboxylic acids with glycidyl esters and of α,β-unsaturated monomers which can be copolymerized with them |
| FR2659327A1 (fr) | 1990-03-08 | 1991-09-13 | Centre Nat Rech Scient | Derives du benzisothiazolinone-1-dioxyde, utilisables comme inhibiteurs des elastases. |
| US5292843A (en) | 1992-05-29 | 1994-03-08 | Union Carbide Chemicals & Plastics Technology Corporation | Polymers containing macromonomers |
| JP2666030B2 (ja) | 1992-09-21 | 1997-10-22 | 昭和高分子株式会社 | 水性シリコーン系グラフト共重合体エマルジョンの製造方法 |
| JP3022039B2 (ja) * | 1993-03-05 | 2000-03-15 | サンスター株式会社 | 歯牙着色防止用口腔用組成物 |
| US5294692A (en) | 1993-06-30 | 1994-03-15 | National Starch And Chemical Investment Holding Corporation | Associative monomers and polymers |
| US5874495A (en) | 1994-10-03 | 1999-02-23 | Rhodia Inc. | Polymers useful as PH responsive thickeners and monomers therefor |
| US5639841A (en) | 1995-02-28 | 1997-06-17 | Union Carbide Chemicals & Plastics Technology Corporation | Polymers containing macromonomer mixtures |
| IT1291520B1 (it) | 1997-04-09 | 1999-01-11 | 3V Sigma Spa | Copolimeri acrilici in emulsione acquosa con miglior potere addesante e sospendente;nuovi monomeri e loro preparazione |
| US6361768B1 (en) * | 1998-12-29 | 2002-03-26 | Pmd Holdings Corp. | Hydrophilic ampholytic polymer |
| US6207778B1 (en) * | 1999-05-07 | 2001-03-27 | Isp Investments Inc. | Conditioning/styling terpolymers |
| US7378479B2 (en) * | 2002-09-13 | 2008-05-27 | Lubrizol Advanced Materials, Inc. | Multi-purpose polymers, methods and compositions |
| US20040241130A1 (en) * | 2002-09-13 | 2004-12-02 | Krishnan Tamareselvy | Multi-purpose polymers, methods and compositions |
| CN1890358A (zh) * | 2003-12-08 | 2007-01-03 | 罗迪亚公司 | 作为酸性含水组合物增稠剂的疏水改性的双季铵盐单体和聚合物 |
| JP2005281375A (ja) * | 2004-03-29 | 2005-10-13 | Kao Corp | 水性組成物 |
| WO2007101048A2 (en) | 2006-02-24 | 2007-09-07 | Lubrizol Advanced Materials, Inc. | Polymerizable silicone copolyol macromers and polymers made therefrom |
| WO2011068820A1 (en) | 2009-12-01 | 2011-06-09 | Lubrizol Advanced Materials, Inc. | Hydrolytically stable multi-purpose polymers |
-
2010
- 2010-12-01 BR BR112012013063A patent/BR112012013063B1/pt not_active IP Right Cessation
- 2010-12-01 CN CN201080054494.1A patent/CN102639575B/zh not_active Expired - Fee Related
- 2010-12-01 EP EP10788193.0A patent/EP2507275B1/en not_active Not-in-force
- 2010-12-01 JP JP2012542148A patent/JP5806226B2/ja not_active Expired - Fee Related
- 2010-12-01 AR ARP100104436A patent/AR079232A1/es not_active Application Discontinuation
- 2010-12-01 US US13/513,306 patent/US9187590B2/en not_active Expired - Fee Related
- 2010-12-01 WO PCT/US2010/058507 patent/WO2011068837A2/en not_active Ceased
- 2010-12-01 ES ES10788193.0T patent/ES2534193T3/es active Active
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2015
- 2015-06-16 JP JP2015121345A patent/JP2015163721A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CN102639575B (zh) | 2018-07-27 |
| US9187590B2 (en) | 2015-11-17 |
| CN102639575A (zh) | 2012-08-15 |
| US20120316308A1 (en) | 2012-12-13 |
| BR112012013063A2 (pt) | 2016-11-22 |
| EP2507275A2 (en) | 2012-10-10 |
| JP2013512330A (ja) | 2013-04-11 |
| WO2011068837A3 (en) | 2011-07-28 |
| ES2534193T3 (es) | 2015-04-20 |
| EP2507275B1 (en) | 2015-03-18 |
| AR079232A1 (es) | 2012-01-04 |
| WO2011068837A2 (en) | 2011-06-09 |
| BR112012013063B1 (pt) | 2020-01-21 |
| JP2015163721A (ja) | 2015-09-10 |
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