WO2007119735A1 - 分散安定剤 - Google Patents
分散安定剤 Download PDFInfo
- Publication number
- WO2007119735A1 WO2007119735A1 PCT/JP2007/057950 JP2007057950W WO2007119735A1 WO 2007119735 A1 WO2007119735 A1 WO 2007119735A1 JP 2007057950 W JP2007057950 W JP 2007057950W WO 2007119735 A1 WO2007119735 A1 WO 2007119735A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- carboxylic acid
- polymerization
- polymer
- dispersion stabilizer
- Prior art date
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- 239000006185 dispersion Substances 0.000 title claims abstract description 56
- 239000003381 stabilizer Substances 0.000 title claims abstract description 54
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 128
- 150000003839 salts Chemical class 0.000 claims abstract description 63
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims abstract description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001735 carboxylic acids Chemical class 0.000 claims abstract description 8
- 229920000642 polymer Polymers 0.000 claims description 154
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 112
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 31
- -1 aromatic carboxylic acids Chemical class 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 26
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 230000004048 modification Effects 0.000 claims description 6
- 238000012986 modification Methods 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 125000000914 phenoxymethylpenicillanyl group Chemical group CC1(S[C@H]2N([C@H]1C(=O)*)C([C@H]2NC(COC2=CC=CC=C2)=O)=O)C 0.000 description 113
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 113
- 238000006116 polymerization reaction Methods 0.000 description 75
- 239000002253 acid Substances 0.000 description 38
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 35
- 239000002245 particle Substances 0.000 description 34
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 24
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000007127 saponification reaction Methods 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 17
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 15
- 239000000839 emulsion Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 244000309464 bull Species 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 239000001530 fumaric acid Substances 0.000 description 11
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 11
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- 239000007787 solid Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
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- 229920002554 vinyl polymer Polymers 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
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- 230000015572 biosynthetic process Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001991 dicarboxylic acids Chemical class 0.000 description 6
- 238000004898 kneading Methods 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 5
- 229910001413 alkali metal ion Inorganic materials 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 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
- 239000003054 catalyst Substances 0.000 description 4
- 239000011362 coarse particle Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 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 4
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 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 3
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
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- 150000002576 ketones Chemical class 0.000 description 3
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- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
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- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 2
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- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
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- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-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
- 229940070765 laurate Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- ADTJPOBHAXXXFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]prop-2-enamide Chemical compound CN(C)CCCNC(=O)C=C ADTJPOBHAXXXFS-UHFFFAOYSA-N 0.000 description 1
- ZIWDVJPPVMGJGR-UHFFFAOYSA-N n-ethyl-2-methylprop-2-enamide Chemical compound CCNC(=O)C(C)=C ZIWDVJPPVMGJGR-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
- CPHCIYGRSFZNRD-UHFFFAOYSA-N n-methyl-1-(4,5,6,7-tetrahydro-1h-indazol-3-yl)methanamine Chemical compound C1CCCC2=C1NN=C2CNC CPHCIYGRSFZNRD-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 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
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical compound CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000005029 sieve analysis Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical class [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000011150 stannous chloride Nutrition 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
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/20—Aqueous medium with the aid of macromolecular dispersing agents
-
- 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
- C08F16/00—Homopolymers and 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
- C08F16/02—Homopolymers and 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 alcohol radical
- C08F16/04—Acyclic compounds
- C08F16/06—Polyvinyl alcohol ; Vinyl alcohol
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/30—Emulsion polymerisation with the aid of emulsifying agents non-ionic
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/34—Higher-molecular-weight carboxylic acid esters
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
Definitions
- the present invention relates to a dispersion stabilizer used in suspension polymerization or emulsion polymerization. More specifically, the present invention relates to a dispersion stabilizer having excellent polymerization stability when used in suspension polymerization or emulsion polymerization of a vinyl compound.
- PVC resin polysalt vinyl resin
- PVC resin has excellent chemical resistance and electrical insulation, and also has excellent heat resistance.
- PVC resin is prepared by using a monomer such as vinyl chloride (hereinafter, vinyl chloride monomer may be abbreviated as vinyl chloride) in an aqueous medium using an oil-soluble polymerization initiator.
- vinyl chloride monomer may be abbreviated as vinyl chloride
- an oil-soluble polymerization initiator e.g., oil-soluble polymerization initiator
- Factors that control the quality of PVC resin when producing it by suspension polymerization include the polymerization rate of PVC resin, the ratio of water and vinyl chloride in the polymerization reaction system, polymerization temperature, type of polymerization initiator and The amount, type of polymerization tank, stirring speed of the polymerization reaction solution, type of dispersion stabilizer, etc. are mentioned. Among these, the influence of the type of dispersion stabilizer is large.
- Patent Documents 1 to 4 As a dispersion stabilizer used in suspension polymerization of chlor chloride, polybutyl alcohol (hereinafter sometimes abbreviated as PVA) is often used (Patent Documents 1 to 4). In order to improve the stability (polymerization stability), it has been proposed to use heat-treated PVA for the polymerization reaction (Patent Documents 1 to 3). However, when suspension polymerization of butyl chloride is performed using these conventional dispersion stabilizers, an effect that is not necessarily satisfactory in terms of polymerization stability is obtained. Let ’s go.
- PVA polybutyl alcohol
- Patent Document 1 Japanese Patent Laid-Open No. 51-45189
- Patent Document 2 Japanese Patent Laid-Open No. 10-67806
- Patent Document 3 Japanese Patent Laid-Open No. 2004-250695
- Patent Document 4 JP-A-8-259609
- PVA is also frequently used as a dispersant for emulsion polymerization of unsaturated monomers.
- so-called “completely saponified PVA” generally having a saponification degree of about 98 mol%, and saponification.
- Partially saponified PVA” with a degree of saponification of about 88 mol% is used.
- the former is used as a dispersion stabilizer, a relatively good unsaturated polymer can be obtained in terms of water resistance and fluidity (high-speed coating property), but the surface activity of the dispersion stabilizer itself is low.
- An object of the present invention is to provide a dispersion stabilizer having excellent polymerization stability when used in suspension polymerization or emulsion polymerization.
- the dispersion stabilizer of the present invention When the dispersion stabilizer of the present invention is used for suspension polymerization such as salt syrup, vinyl chloride can be stably polymerized, and therefore the block caused by unstable polymerization. As a result, polymer particles having a sharp particle size distribution with few coarse particles can be obtained. Further, even when the dispersion stabilizer of the present invention is used for emulsion polymerization of unsaturated monomers, the unsaturated monomers can be stably polymerized, and the resulting polymer has a small amount of filtration remaining. It is possible to achieve an excellent effect.
- carboxylic acid having an unsaturated double bond used in the present invention, acrylic acid, methacrylic acid, crotonic acid, isocrotonic acid, propionic acid, 2_pentenoic acid, 4_pentenoic acid, 2-heptenoic acid , 2-Otathenic acid, cinnamate, myristoleic acid, palmitoleic acid, oleic acid, elaidic acid, batasenic acid, gadoleic acid, erucic acid, nervonic acid, linoleic acid, linolenic acid, eleostearic acid, stearidone Unsaturated monocarboxylic acids such as acid, arachidonic acid, eicosapentaenoic acid, succinic acid, docosahexaenoic acid, sorbic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, itaconic acid, citraconic acid,
- Aliphatic carboxylic acids that do not contain an olefinic unsaturated bond in the molecule of the present invention include formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, caprylic acid, and force puric acid. , Lauric acid, myristic acid, palmitic acid, stearic acid, cyclohexanecarboxylic acid, acetoacetic acid, glycololeic acid, lactic acid, ascorbic acid, etc.
- aromatic carboxylic acids that do not contain olefinic unsaturated bonds in the molecule include aromatic monocarboxylic acids such as phenylacetic acid, benzoic acid, toluic acid, salicylic acid; phthalic acid, isophthalic acid, terephthalic acid, p- Aromatic dicarboxylic acids such as hydroxybenzoic acid.
- aliphatic carboxylic acids and / or aromatic carboxylic acids can also be used as salts.
- an aliphatic carboxylic acid and / or an aromatic carboxylic acid or a salt thereof having two or more carboxyl groups in the molecule is preferred.
- the aliphatic carboxylic acid and / or aromatic carboxylic acid or a salt thereof can be used alone or in combination of two or more.
- polyvinyl alcohol polymer (hereinafter, polyvinyl alcohol polymer may be abbreviated as PVA polymer) (A) obtained by esterifying PVA polymer having a double bond in the side chain
- PVA polymer obtained by esterifying PVA polymer having a double bond in the side chain
- the saponification degree of the PVA polymer (A) is preferably 60 mol% or more.
- the upper limit of the saponification degree is not particularly limited.
- a PVA polymer (B) or a carboxylic acid-modified PVA polymer (C) having a double bond in the side chain obtained by esterifying the PVA polymer (A) is dispersed for emulsion polymerization.
- the degree of saponification of the PVA polymer (A) is preferably 50 mol% or more, more preferably 70 mol% or more, still more preferably 80 mol% or more, and particularly preferably 83 mol%.
- the upper limit of the saponification degree is not particularly limited.
- the degree of polymerization of the PVA polymer (A) is not particularly limited, but is preferably 100 to 8,000, more preferably ⁇ 200 to 3000, and further preferably ⁇ 250 to 2500.
- the bull ester polymer used as a raw material for producing the PVA polymer (A) is a bulk polymerization method, solution polymerization method, suspension polymerization method, emulsion polymerization of a vinyl ester monomer.
- a conventionally known method such as a combination method, dispersion polymerization method, etc.
- the power to do S is the industrial viewpoint.
- preferred polymerization methods are the solution polymerization method, the emulsion polymerization method and the dispersion polymerization method. In the polymerization operation, any one of a batch method, a semi-batch method and a continuous method can be employed.
- butyl ester monomers examples include butyl acetate, formate, propionate, prillate, and versatic butyl. Is preferable from an industrial viewpoint.
- the bull ester monomer may be copolymerized with another monomer as long as the gist of the present invention is not impaired.
- the monomer that can be used include ethylene-propylene, n-butene, isobutylene, and the like; acrylic acid and its salts, methyl acrylate, ethyl acrylate, n-propinole acrylate, and i-acrylate.
- Acrylic esters such as propyl, n-butyl acrylate, i-butyl acrylate, t-butyl acrylate, 2-ethylhexyl acrylate, dodecyl acrylate, octadecyl acrylate; methacrylic acid and its salts; methacryl Acid methylol, ethyl methacrylate, n-propyl methacrylate, i-propyl methacrylate, n-butyl methacrylate, i-butyl methacrylate, t-butyl methacrylate, 2-ethyl hexyl hexyl, dodecyl methacrylate, methacrylic acid Methacrylate esters such as Octadecyl Acrylamide, N-methylacrylamide, N-ethylacrylamide, N, N-dimethylaretalinoleamide, diacetoneacrylamide, acrylamidepropanesulfonic acid and its
- a chain transfer agent may be allowed to coexist for the purpose of adjusting the degree of polymerization of the resulting bull ester polymer during the polymerization of the bull ester monomer.
- Chain transfer agents include aldehydes such as acetoaldehyde, propionaldehyde, butyraldehyde, benzaldehyde; ketones such as acetone, methyl ethyl ketone, hexanone, cyclohexanone; 2-hydroxyethanethiol, dodecyl mercaptan, etc. Mercaptans; halogenated hydrocarbons such as trichloroethylene and perchloroethylene, among which aldehydes and ketones are preferably used.
- the amount of chain transfer agent added is determined according to the chain transfer constant of the chain transfer agent to be added and the degree of polymerization of the target vinyl ester polymer, but is generally 0. 1 to: 10% by weight is desirable.
- the content of 1,2-glycol bonds is large, which is obtained by saponifying a butyl ester polymer obtained by polymerizing a vinyl ester monomer under a temperature condition higher than usual.
- PVA polymers can also be preferably used.
- the content of 1,2-glycol bond is not particularly limited, but is preferably 1.9 mol% or more, more preferably 2.0 mol% or more, and even more preferably 2.1 mol% or more. It is.
- a conventionally known basic catalyst such as sodium hydroxide, potassium hydroxide or sodium methoxide
- an acidic catalyst such as p-toluenesulfonic acid.
- Solvents used in the saponification reaction include alcohols such as methanol and ethanol; esters such as methanolate and ethyl acetate; ketones such as acetone and methyl ethyl ketone; aromatic hydrocarbons such as benzene and toluene. These may be used alone or in combination of two or more.
- the PVA polymer (A) used in the present invention may have an ionic functional group at the terminal.
- these ionic functional groups include a carboxyl group and a sulfonic acid group, and among them, a carboxyl group is preferable.
- These ionic groups include salts thereof, and from the viewpoint that the PVA polymer (A) is preferably water-dispersible, an alkali metal salt is preferable.
- butyl acetate is used in the presence of a thiol compound such as thiolacetic acid, mercaptopropionic acid, 3_mercapto_1_propanesulfonic acid sodium salt, etc.
- a method such as polymerizing a bis-esterol monomer and saponifying the resulting polymer can be used.
- the PVA polymer (A) is a carboxylic acid having an unsaturated double bond or a salt thereof, or an aliphatic carboxylic acid or aromatic carboxylic acid having no olefinic unsaturated bond in the molecule.
- carboxylic acid or a salt thereof
- Examples of the method include: (1) a method in which an eight-based polymer (eight) is reacted with a carboxylic acid or a salt thereof in an anhydrous solvent in a suspended state; (ii) a carboxylic acid or a salt thereof in powder form, , Is a method in which it is dissolved or dispersed in alcohol or water such as methanol, ethanol, propanol, etc., and then mixed with a slurry or powdered PVA polymer (A) and reacted by heat treatment in a nitrogen or air atmosphere.
- the conditions for the heat treatment of the mixture of the PVA polymer (A) and the carboxylic acid or salt thereof are not particularly limited, but the temperature during the heat treatment is 60. ⁇ : 190 ° C is preferred 65 ⁇ : 185 ° C force S is preferred, 70 ⁇ : 180 ° C is more preferred.
- the heat treatment time is preferably 0.5 to 20 hours 1 to 18 hours is more preferred 1 to 16 hours Is preferred.
- the temperature at which the PVA polymer (A) and the carboxylic acid or salt thereof are melt-mixed is preferably 130 to 250 ° C and 140 to 220 ° C. More preferred.
- the time for the PVA polymer (A) and the carboxylic acid or salt thereof to stay in the apparatus used for melt-kneading is preferably:! To 15 minutes, more preferably 2 to 10 minutes.
- plasticizer usually used in PVA, thereby lowering the temperature during the heat treatment.
- the plasticizer include polyhydric alcohols such as glycerin, diglycerin, polyethylene glycol, polypropylene glycol, and sorbitol; compounds obtained by adding ethylene oxide to these alcohols; water; sugars; polyethers; amide compounds, etc. These can be used alone or in combination of two or more.
- the amount of these plasticizers used is usually 1 to 300 parts by weight with respect to 100 parts by weight of the PVA polymer, and more preferably:! To 200 parts by weight.
- the carboxylic acid having an unsaturated double bond or a salt thereof When the PVA polymer (A) and the carboxylic acid having an unsaturated double bond or a salt thereof are heat-treated, the carboxylic acid having an unsaturated double bond or a salt thereof, or the PVA
- a polymerization inhibitor examples include phenolic polymerization-inhibited chiral IJ such as hydroquinone and hydroquinone monomethyl ether, phenothiazine, N, N-diphenylparaphenylenediamine and the like.
- the blending amount of the polymerization inhibitor is preferably 0.0001 to 10 parts by weight with respect to 100 parts by weight of the PVA polymer, and more preferably 0.000 to 1 part by weight.
- the PVA polymer (A) and the carboxylic acid or salt thereof are heat-treated, 0.003 to 3% by weight of alkali metal ions are added to 100 parts by weight of the PVA polymer (A). It is preferable that the PVA-based polymer (A) is contained at a ratio of the above, since thermal deterioration, thermal decomposition, gelation, coloring, and the like of the PVA polymer (A) can be suppressed.
- the alkali metal ions include potassium ions, sodium ions, magnesium ions, etc., which are mainly present as salts of lower fatty acids such as acetic acid and propionic acid, and the PVA polymer (A) is a carboxylate. Group When it has a sulfonic acid group, it exists as a salt of these functional groups.
- the content of alkali metal ions in the PV A polymer can be measured by an atomic absorption method.
- a PVA polymer in order to promote esterification of the PVA polymer (A) with a carboxylic acid or a salt thereof, a PVA polymer (in a state where an acidic substance or basic substance acting as a catalyst is blended) It is also possible to heat-treat A) and a carboxylic acid having an unsaturated double bond or a salt thereof.
- acidic substances include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid; organic acids such as formic acid, acetic acid, oxalic acid, and p_toluenesulfonic acid; and salts such as pyridinium p-toluenesulfonic acid and ammonium chloride. ; Noleic acid such as zinc chloride, aluminum chloride, iron trichloride, tin dichloride, tin tetrachloride, boron trifluoride jetyl ether complex, etc. Can be used in combination.
- inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid
- organic acids such as formic acid, acetic acid, oxalic acid, and p_toluenesulfonic acid
- salts such as pyridinium p-toluenesulfonic acid and ammonium chlor
- basic substances include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; metal oxides such as barium oxide and silver oxide; hydrogen Alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal amides such as sodium amide and potassium amide, and the like. More than one species can be used in combination.
- the blending amount of these acidic substances and basic substances is usually preferably 0.0001 to 5 parts by weight with respect to 100 parts by weight of the PVA polymer.
- the PVA polymer (A) may be used alone, or two or more PVA polymers (A) having different characteristics may be mixed and used.
- a PVA polymer (B) having a double bond in the side chain is obtained.
- the amount of modification with a carboxylic acid having an unsaturated double bond or a salt thereof can be determined by, for example, dissolving a PVA polymer (B) in a d6_DMSO solvent and measuring it by 1H-NMR. And a method for measuring and obtaining unreacted carboxylic acid by high performance liquid chromatography.
- the PVA polymer (B) and the PVA polymer (C) are obtained by esterification.
- 0.01 to 50 Monore 0/0 force S preferably per Monomayu knit introduced carboxylic acid or a modified amount of the PVA polymer by a salt thereof (A), preferably from 0.01 to 25 Monore 0/0 force S, 0.02 to 20 mole 0/0 more preferably tool 0. 05 ⁇ : particularly preferably 15 mol 0/0.
- the PVA polymer (B) is a PVA polymer obtained by esterifying the PVA polymer (A) with an unsaturated dicarboxylic acid, or the PVA polymer (C) is PV
- the carboxyl group that is not involved in the ester bond is substituted with 1 to 3 valent carboxyl groups. It is also suitably carried out to react with any one of the metal hydroxides, salts, alkoxides, ammonia, ammonium salts, amine salts and amine salts.
- the PVA polymer (B) or the PVA polymer (C) is suitably used as a suspension stabilizer for suspension polymerization, particularly for suspension polymerization of a bull compound.
- the Bulle compounds include: vinyl halides such as salt butyls; Bull esters such as vinyl acetate and vinyl propionate; acrylic acid, methacrylic acid, esters and salts thereof; maleic acid, fumaric acid, esters thereof and anhydrides Styrene, acrylonitrile, vinylidene chloride, vinyl ether and the like.
- vinyl chloride is particularly preferably used in suspension polymerization alone or together with a monomer capable of copolymerizing with vinyl chloride and butyl chloride.
- Monomers that can be copolymerized with vinyl chloride include bisesters such as vinyl acetate and propionate butyl; (meth) acrylate esters such as methyl (meth) acrylate and ethyl (meth) acrylate; ethylene And monoolefins such as propylene; unsaturated dicarboxylic acids such as maleic anhydride and itaconic acid; acrylonitrile, styrene, vinylidene chloride and butyl ether.
- oil-soluble or water-soluble polymerization initiators conventionally used for polymerization of vinyl chloride monomers and the like can be used.
- oil-soluble polymerization initiator include percarbonate compounds such as diisopropyl peroxydicarbonate, di-2-ethenolehexenoreperoxydicarbonate, and jetoxetino leperoxydicarbonate; Oxyneodecanate, t_butylperoxybivalate, t-hexyloxypivalate, one-milperoxyneoxydecane Perester compounds such as nates; acetyl cyclohexylsulfonyl peroxide
- water-soluble polymerization initiator examples include potassium persulfate, ammonium persulfate, hydrogen peroxide, cumene hydride peroxide and the like. These oil-soluble or water-soluble polymerization initiators can be used alone or in combination of two or more.
- additives Upon suspension polymerization of the vinyl compound, other various additives can be added to the polymerization reaction system as necessary.
- the additive include polymerization regulators such as aldehydes, halogenated hydrocarbons and mercaptans, and polymerization inhibitors such as phenol compounds, phenol compounds and N-oxide compounds.
- a pH adjuster, a crosslinking agent, etc. can be added arbitrarily.
- the polymerization temperature is not particularly limited.
- the polymerization temperature can be adjusted to a high temperature exceeding 90 ° C as well as a low temperature of about 20 ° C.
- the amount used is not particularly limited, and the unsaturated monomer used for emulsion polymerization is 100. It is preferably used in the range of 1 to 20 parts by weight, more preferably 2 to 15 parts by weight, and particularly preferably 3 to 13 parts by weight in terms of solid content with respect to the parts by weight.
- the PVA polymer (B) is used as a dispersion stabilizer in an amount within the above range, the polymerization stability is further improved.
- Examples of the unsaturated monomer include olefins such as ethylene, propylene, and isobutylene; halogenated olefins such as chloro chloride, fluorinated buluyl, vinylidene glolide, and vinylidene fluoride; bur formate, bur acetate, propionic acid Bull esters such as bulls and versatic acid burs; acrylics such as acrylic acid, methacrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethyl hexyl acrylate, dodecyl acrylate, 2-hydroxetyl acrylate Acid ester; methyl metechlylate, ethyl methacrylate, meta Methacrylic acid esters such as butyl acrylate, 2-ethylhexyl methacrylate, dodecyl methacrylate, 2-hydroxyethyl methacrylate; dimethylaminoe
- acrylamide monomers such as attalinoleamide, methacrylolamide, N-methylolacrylamide, N, N-dimethylatalinoleamide, acrylamide_2_methylpropanesulfonic acid and its sodium salt; styrene, monomethylstyrene, Examples thereof include p-styrene sulfonic acid and styrene monomers such as sodium and potassium salts; N-butylpyrrolidone; and gen-based monomers such as butadiene, isoprene, and black-open plane.
- unsaturated monomers can be used alone or in admixture of two or more.
- Suitable unsaturated monomer polymers include poly (butyl acetate), ethylene / butyl acetate copolymers, and (meth) acrylate esters (co) polymers.
- the dispersion stabilizer composed of the PVA polymer (B) or PVA polymer (C) of the present invention includes, as necessary, preservatives and antifungal agents that are usually used in suspension polymerization and emulsion polymerization. Additives such as agents, anti-blocking agents and antifoaming agents can be added.
- the dispersion stabilizer of the present invention when used for suspension polymerization or emulsion polymerization, the dispersion stabilizer may be used alone, but methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, etc.
- a water-soluble or water-dispersible dispersion stabilizing aid can be used in combination, and the dispersion stabilizing aid has a saponification degree of 65 mol%.
- a partially saponified PVA having a polymerization degree of 50 to 750, preferably a saponification degree of 30 to 60 mol% and a polymerization degree of 180 to 650 is suitably used.
- the dispersion stabilizing aid may be provided with self-emulsifying properties by introducing an ionic group such as carboxylic acid or sulfonic acid.
- the weight ratio of the dispersion stabilizer to the dispersion stabilizer added varies depending on the type of dispersion stabilizer used, etc. However, the range of 95/5 to 20/80 is preferable, and 90Z10 to 30Z70 is particularly preferable.
- the dispersion stabilizer and the dispersion stabilizing aid may be charged all at the beginning of the polymerization, or may be charged separately during the polymerization.
- parts and% indicate parts by weight and% by weight, respectively.
- the dispersion stabilizer was prepared by dissolving the PVA polymer (B) obtained above in deionized water in an amount corresponding to 600 ppm with respect to vinyl chloride. 1150 g of the dispersion stabilizer thus obtained was charged into a 5 L glass-lined autoclave. Next, 1-5 g of a 70% toluene solution of diisopropyl peroxydicarbonate was charged into a dull lining autoclave, degassed until the pressure in the autoclave reached 0 ⁇ 0067 MPa, and oxygen was removed. lOOOg is charged and the contents in the autoclave are 57 ° C. The polymerization was started with stirring. The pressure in the autoclave at the start of polymerization was 0.83 MPa.
- the average particle size, particle size distribution, and scale adhesion amount of the chlorinated polymer particles were measured according to the following method. Table 1 shows the evaluation results.
- the particle size distribution was measured by dry sieve analysis to determine the average particle size.
- the content of JIS standard sieve 42 mesh on was expressed in weight%. The smaller the number, the smaller the coarse particles, the sharper the particle size distribution, and the better the polymerization stability.
- the state of scale adhesion on the inner wall of the polymerization tank after removing the polymer slurry from the polymerization tank was visually observed and evaluated according to the following criteria.
- Table 1 shows the evaluation results of the vinyl chloride polymer particles.
- a PVA polymer was synthesized in the same manner as in Example 1 except that the powder of PVA polymer (A) shown in Table 1 was added to a solution containing fumaric acid and a methanol solution, followed by heat treatment.
- suspension polymerization of butyl chloride was carried out to obtain chlorinated polymer particles.
- Table 1 shows the evaluation results. Uniform polymer particles could not be obtained due to the presence of coarse particles, and the amount of scale adhered was large and stable polymerization could not be performed.
- the dispersion stabilizer was prepared by dissolving the PVA polymer (C) obtained above in deionized water in an amount corresponding to 800 ppm with respect to the salt cellulose. 1150 g of the dispersion stabilizer thus obtained was charged into a 5 L glass-lined autoclave. Next, 1.5 g of a 70% solution of diisopropyl peroxydicarbonate in a dull lining autoclave is charged and degassed until the pressure in the autoclave reaches 0.0061 MPa. After removing oxygen, VIOOOg chloride was charged, and the contents in the autoclave were heated to 57 ° C., and polymerization was started with stirring. The pressure in the autoclave at the start of polymerization was 0.83 MPa.
- suspension polymerization of salt bulls was carried out to obtain chlorinated bur polymer particles.
- Table 1 shows the evaluation results of the vinyl chloride polymer particles.
- 1 part by weight of fumaric acid is dry-blended with 100 parts by weight of PVA polymer (A) powder having a polymerization degree of 500 and a saponification degree of 74 mol%, and using a lab plastmill for 2 minutes at a temperature of 203 ° C.
- the mixture was melt melt-kneaded, and the kneaded product was Soxhlet washed with THF to obtain a PVA polymer (B).
- a 1H-NMR measurement was performed by dissolving the PVA polymer (B) in a d6-DMSO solvent, a signal derived from a double bond was observed at 6.5 ppm.
- the amount of modification with the carboxylic acid to the PV A polymer (B) was 0.5 mol%.
- Example 2 The same as in Example 1, except that the fumaric acid was not dry blended, and the PVA polymer (B) synthesized in the same manner as in Example 21 was used except that melt kneading was performed under the conditions shown in Table 2.
- the ability of the suspension polymerization of butyl chloride to form a butyl chloride polymer particle was not possible because the salt syllable was blocked and could not be polymerized.
- PVA polymer (A) 100 parts by weight of PVA polymer (A) with a polymerization degree of 550 and a saponification degree of 74 mol% are dry blended with 1 part by weight of gnoretaric acid, and a lab plastmill is used at 200 ° C for 2 minutes. After melt-kneading, the kneaded product was soxhlet washed with THF to obtain a PVA polymer (C). The amount of modification to the PVA polymer (C) by carboxylic acid was 0.5 mol%. (Suspension polymerization of butyl chloride)
- Example 13 suspension polymerization of salt hybrid was conducted, and the resulting salt vinyl polymer particles were evaluated in the same manner as in Example 13. Table 2 shows the evaluation results.
- a PVA polymer (C) synthesized in the same manner as in Example 24 was used except that 1 part by weight of adipic acid was used in place of 1 part by weight of gnoretaric acid and heat treatment was performed under the conditions shown in Table 2.
- suspension polymerization of vinyl chloride was performed to obtain vinyl chloride polymer particles.
- Table 2 shows the evaluation results of the chlorinated polymer particles.
- a 1 L glass reactor equipped with a stirrer, reflux condenser, dropping funnel, nitrogen inlet tube and thermometer was charged with 312 g of PVA polymer (B) adjusted to a concentration of 2.5% and the temperature was adjusted to 60 After adjusting to ° C, 26 g of butyl acetate and 20 of sodium tartrate. A solution of 15 g of / o aqueous solution was charged, and the inside of the system was replaced with nitrogen. While stirring the contents of the reactor at 200 rpm, 30 g of 5% hydrogen peroxide water was continuously added dropwise over 2.5 hours to carry out polymerization. After 30 minutes from the start of the polymerization, it was confirmed that the initial polymerization was completed.
- PVA polymer as (A) similarly to the polymerization degree of 1700, Keni ⁇ 98.5 Monore 0/0, 1, 2-glycolic binding amount 2. except for using 2 mole% PVA Example 23 Using the PV A polymer (B) synthesized as described above, emulsion polymerization of vinyl acetate was conducted in the same manner as in Example 26 to obtain a poly (vinyl acetate) resin resin emulsion. When the obtained emulsion was filtered through a 200 mesh stainless steel wire mesh, the remaining amount of filtration was as low as 0.05% (solid content). The qualitative properties were also excellent. The results are shown in Table 3.
- a 1 L glass reactor equipped with a stirrer, reflux condenser, dropping funnel, nitrogen inlet tube and thermometer was charged with 312 g of PVA polymer (C) adjusted to a concentration of 2.5% and the temperature was adjusted to 60 After adjusting the temperature to 26 ° C., 26 g of butyl acetate and 15 g of a 20% aqueous solution of sodium tartrate were charged, and the system was replaced with nitrogen. While stirring the contents of the reactor at 200 rpm, 30 g of 5% hydrogen peroxide water was continuously added dropwise over 2.5 hours to carry out polymerization.
- Emulsion polymerization of vinyl acetate was carried out in the same manner as in Example 30.
- Polyacetate bur resin emulsion was obtained.
- the obtained emulsion was filtered through a 200 mesh stainless steel wire mesh. / 0 (solid content) and low at the time of polymerization
- the qualitative properties were also excellent. The results are shown in Table 3.
- the dispersion stabilizer of the present invention has excellent polymerization stability when used during suspension polymerization, it reduces block formation and scale adhesion due to unstable polymerization, reduces coarse particles, and has a sharp particle size. Polymer particles having a distribution can be obtained, or, when used for emulsion polymerization, since the polymerization stability is excellent, a polymer with a small amount of filtration can be obtained, which is extremely useful industrially.
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CN2007800131097A CN101421309B (zh) | 2006-04-12 | 2007-04-11 | 分散稳定剂 |
ES07741386T ES2423833T3 (es) | 2006-04-12 | 2007-04-11 | Estabilizador de dispersión |
KR1020087027646A KR101385069B1 (ko) | 2006-04-12 | 2007-04-11 | 분산 안정제 |
EP07741386.2A EP2006307B1 (en) | 2006-04-12 | 2007-04-11 | Dispersion stabilizer |
JP2008510957A JP5325573B2 (ja) | 2006-04-12 | 2007-04-11 | 分散安定剤 |
US12/295,352 US8426518B2 (en) | 2006-04-12 | 2007-04-11 | Dispersion stabilizer |
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Also Published As
Publication number | Publication date |
---|---|
EP2006307A4 (en) | 2010-01-20 |
TWI413649B (zh) | 2013-11-01 |
KR20090018051A (ko) | 2009-02-19 |
EP2006307B1 (en) | 2013-07-17 |
KR101385069B1 (ko) | 2014-04-14 |
CN101421309A (zh) | 2009-04-29 |
EP2006307A1 (en) | 2008-12-24 |
US8426518B2 (en) | 2013-04-23 |
US20090111940A1 (en) | 2009-04-30 |
JP5325573B2 (ja) | 2013-10-23 |
CN101421309B (zh) | 2012-12-05 |
JPWO2007119735A1 (ja) | 2009-08-27 |
TW200801054A (en) | 2008-01-01 |
ES2423833T3 (es) | 2013-09-24 |
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