JP2013079340A - Aqueous dispersion - Google Patents
Aqueous dispersion Download PDFInfo
- Publication number
- JP2013079340A JP2013079340A JP2011220487A JP2011220487A JP2013079340A JP 2013079340 A JP2013079340 A JP 2013079340A JP 2011220487 A JP2011220487 A JP 2011220487A JP 2011220487 A JP2011220487 A JP 2011220487A JP 2013079340 A JP2013079340 A JP 2013079340A
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- JP
- Japan
- Prior art keywords
- mass
- meth
- group
- parts
- acrylate
- 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.)
- Granted
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- 239000006185 dispersion Substances 0.000 title claims abstract description 59
- 239000002270 dispersing agent Substances 0.000 claims abstract description 49
- 229920005672 polyolefin resin Polymers 0.000 claims abstract description 33
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000178 monomer Substances 0.000 claims abstract description 24
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 12
- 229920000642 polymer Polymers 0.000 claims description 46
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000003365 glass fiber Substances 0.000 claims description 9
- -1 polypropylene Polymers 0.000 description 232
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 94
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 48
- 229920001577 copolymer Polymers 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 26
- 239000004743 Polypropylene Substances 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 21
- 229920001155 polypropylene Polymers 0.000 description 21
- 239000000126 substance Substances 0.000 description 19
- 150000005215 alkyl ethers Chemical class 0.000 description 17
- 238000006116 polymerization reaction Methods 0.000 description 17
- 238000000034 method Methods 0.000 description 11
- 229920002554 vinyl polymer Polymers 0.000 description 11
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000003505 polymerization initiator Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000006096 absorbing agent Substances 0.000 description 8
- 230000032683 aging Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004945 emulsification Methods 0.000 description 8
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 150000001414 amino alcohols Chemical class 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 238000004513 sizing Methods 0.000 description 7
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 6
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 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 5
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000006087 Silane Coupling Agent Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 5
- 238000005342 ion exchange Methods 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 4
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 4
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229960002887 deanol Drugs 0.000 description 4
- 239000012972 dimethylethanolamine Substances 0.000 description 4
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011151 fibre-reinforced plastic Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000004711 α-olefin Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 3
- 239000003093 cationic surfactant Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229920005603 alternating copolymer Polymers 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 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
- RAJUSMULYYBNSJ-UHFFFAOYSA-N prop-1-ene-1-sulfonic acid Chemical compound CC=CS(O)(=O)=O RAJUSMULYYBNSJ-UHFFFAOYSA-N 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 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
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- IYMSIPPWHNIMGE-UHFFFAOYSA-N silylurea Chemical compound NC(=O)N[SiH3] IYMSIPPWHNIMGE-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Abstract
Description
本発明は、水性分散体に関する。 The present invention relates to an aqueous dispersion.
炭素繊維、ガラス繊維などの強化繊維とマトリックス樹脂とからなる繊維強化プラスチック(FRP)は、金属材料に比べて軽量であり、かつ強化繊維を含まないプラスチックに比べて機械的強度や弾性率が高い材料である。このような特性を有することから、繊維強化プラスチックは、航空機、自動車、鉄道車両、船舶などの多くの分野で利用されている。 Fiber reinforced plastic (FRP) made of reinforced fibers such as carbon fiber and glass fiber and matrix resin is lighter than metal materials and has higher mechanical strength and elastic modulus than plastics that do not contain reinforced fibers. Material. Because of such properties, fiber reinforced plastics are used in many fields such as aircraft, automobiles, railway vehicles, and ships.
従来、ポリエチレン、ポリプロピレン等のポリオレフィン樹脂がマトリックス樹脂である繊維強化プラスチックの補強剤として使用されるガラス繊維としては、酸変性ポリプロピレン系樹脂の水性エマルジョンを含む集束剤が塗布されたガラス繊維が用いられている(例えば、特許文献1参照)。 Conventionally, glass fiber coated with a sizing agent containing an aqueous emulsion of acid-modified polypropylene resin is used as a glass fiber used as a reinforcing agent for fiber-reinforced plastics in which polyolefin resins such as polyethylene and polypropylene are matrix resins. (For example, refer to Patent Document 1).
また、チョップドストランドの集束性を改善する目的で、高分子分散剤としてスチレン−無水マレイン酸共重合体を用いた高分子量のポリオレフィンの水性エマルジョンが提案されている(例えば、特許文献2参照)。 Further, for the purpose of improving the sizing property of chopped strands, an aqueous emulsion of a high molecular weight polyolefin using a styrene-maleic anhydride copolymer as a polymer dispersant has been proposed (for example, see Patent Document 2).
しかし、特許文献1で用いられている酸変性ポリプロピレン系樹脂の分子量は低いものであるため、水性エマルジョンから形成される乾燥皮膜の強度が低く、ガラス繊維のチョップドストランドの集束性は満足できるものではなかった。 However, since the molecular weight of the acid-modified polypropylene resin used in Patent Document 1 is low, the strength of the dry film formed from the aqueous emulsion is low, and the convergence of the chopped strands of glass fiber is not satisfactory. There wasn't.
また、特許文献2に記載の技術では、高分子量ポリオレフィン樹脂の分散が不十分であり、さらに乳化剤として脂肪酸を併用しなければエマルジョンにすることができず、ミスト化した脂肪酸により火災になる虞があるため、製造方法の改善が求められていた。 Moreover, in the technique described in Patent Document 2, the dispersion of the high molecular weight polyolefin resin is insufficient, and furthermore, an emulsion cannot be formed unless a fatty acid is used in combination as an emulsifier, and there is a risk of fire due to the misted fatty acid. For this reason, improvement of the manufacturing method has been demanded.
そこで、本発明は、上記事情に鑑みなされたものであり、集束性および密着性に優れ、かつ工業的に有利に製造できる高分子量ポリオレフィン樹脂の水性分散体を提供することを目的とする。 Then, this invention is made | formed in view of the said situation, and it aims at providing the aqueous dispersion of the high molecular weight polyolefin resin which is excellent in convergence and adhesiveness, and can be manufactured industrially advantageously.
上記課題を解決すべく、本発明者らは鋭意検討を積み重ねた。その結果、不飽和カルボン酸と(メタ)アクリルアミド単量体とを共重合して得られる高分子分散剤を用いることにより、高分子量のポリオレフィン樹脂が効率よく水性媒体中に分散し、また工業的にも安全に製造できることを見出し、本発明を完成させた。 In order to solve the above-mentioned problems, the present inventors have intensively studied. As a result, by using a polymer dispersant obtained by copolymerizing an unsaturated carboxylic acid and a (meth) acrylamide monomer, a high molecular weight polyolefin resin is efficiently dispersed in an aqueous medium, and industrially. In addition, the present inventors have found that it can be manufactured safely and completed the present invention.
すなわち、本発明は、重量平均分子量が2万以上であるポリオレフィン樹脂(A)と、不飽和カルボン酸(b−1) 3.5〜90質量部および(メタ)アクリルアミド単量体(b−2) 10〜96.5質量部(ただし、(b−1)と(b−2)との合計は100質量部)を含む単量体成分を共重合して得られる高分子分散剤(B)と、を含む、水性分散体である。 That is, the present invention relates to a polyolefin resin (A) having a weight average molecular weight of 20,000 or more, 3.5 to 90 parts by mass of an unsaturated carboxylic acid (b-1) and a (meth) acrylamide monomer (b-2). ) A polymer dispersant (B) obtained by copolymerizing a monomer component containing 10 to 96.5 parts by mass (however, the sum of (b-1) and (b-2) is 100 parts by mass) And an aqueous dispersion.
本発明によれば、集束性および密着性に優れ、かつ工業的に有利に製造できる高分子量ポリオレフィン樹脂の水性分散体が提供されうる。 ADVANTAGE OF THE INVENTION According to this invention, the aqueous dispersion of the high molecular weight polyolefin resin which is excellent in bundling property and adhesiveness, and can be manufactured industrially advantageously can be provided.
以下、本発明の水性分散体を詳細に説明する。なお、本明細書において、「(メタ)アクリレート」とは、アクリレートおよびメタクリレートの総称である。(メタ)アクリル酸等の(メタ)を含む化合物等も同様に、名称中に「メタ」を有する化合物と「メタ」を有さない化合物の総称である。このため、「(メタ)アクリル」とは、アクリルおよびメタクリル双方を包含する。例えば、「(メタ)アクリル酸」とは、アクリル酸およびメタクリル酸双方を包含する。 Hereinafter, the aqueous dispersion of the present invention will be described in detail. In this specification, “(meth) acrylate” is a general term for acrylate and methacrylate. Similarly, a compound containing (meth) such as (meth) acrylic acid is a general term for a compound having “meta” in the name and a compound not having “meta”. For this reason, "(meth) acryl" includes both acrylic and methacrylic. For example, “(meth) acrylic acid” includes both acrylic acid and methacrylic acid.
[ポリオレフィン樹脂]
本発明で用いられるポリオレフィン樹脂(A)は、重量平均分子量が2万以上である。重量平均分子量が2万未満であると、得られる乾燥皮膜の強度が低くなる。該重量平均分子量は、好ましくは3万以上、より好ましくは5万以上である。また、重量平均分子量の上限は特に制限されないが、乳化性を考慮すれば、好ましくは40万以下であり、より好ましくは20万以下である。なお、ポリオレフィン樹脂(A)の重量平均分子量は、ゲル浸透クロマトグラフィ(GPC)により測定した値を採用するものとする。
[Polyolefin resin]
The polyolefin resin (A) used in the present invention has a weight average molecular weight of 20,000 or more. When the weight average molecular weight is less than 20,000, the strength of the resulting dried film is lowered. The weight average molecular weight is preferably 30,000 or more, more preferably 50,000 or more. The upper limit of the weight average molecular weight is not particularly limited, but is preferably 400,000 or less, more preferably 200,000 or less in consideration of emulsifiability. In addition, the value measured by gel permeation chromatography (GPC) shall be employ | adopted for the weight average molecular weight of polyolefin resin (A).
ポリオレフィン樹脂(A)としては、オレフィン化合物の単独重合体または共重合体を用いることができる。該オレフィン化合物の単独重合体としては、例えば、ポリエチレン(低密度ポリエチレン、中密度ポリエチレン、高密度ポリエチレン、または線状低密度ポリエチレンなど)、ポリプロピレン、ポリイソブチレン、ポリ(1−ブテン)、ポリ(1−ペンテン)、ポリ(1−ヘキセン)等の炭素数2〜20のα−オレフィンの単独重合体を挙げることができ、共重合体としては、例えば、エチレン−プロピレン共重合体、エチレン−1−ブテン共重合体、エチレン−1−オクテン共重合体、エチレン−1−ヘキセン共重合体等を挙げることができる。 As the polyolefin resin (A), a homopolymer or copolymer of an olefin compound can be used. Examples of the homopolymer of the olefin compound include polyethylene (low density polyethylene, medium density polyethylene, high density polyethylene, or linear low density polyethylene), polypropylene, polyisobutylene, poly (1-butene), poly (1 -Pentene), poly (1-hexene) and the like homopolymers of α-olefins having 2 to 20 carbon atoms, such as ethylene-propylene copolymer, ethylene-1- Examples include butene copolymer, ethylene-1-octene copolymer, and ethylene-1-hexene copolymer.
また、極性基が導入されたポリオレフィン樹脂も使用できる。極性基が導入されたポリオレフィン樹脂の具体例としては、無水マレイン酸変性ポリエチレン、マレイン酸変性ポリエチレン、アクリル酸変性ポリエチレン、無水マレイン酸変性ポリプロピレン、マレイン酸変性ポリプロピレン、無水マレイン酸変性エチレン−プロピレン共重合体、アクリル酸変性ポリプロピレンなどの酸変性ポリオレフィン;エチレン−塩化ビニル共重合体、エチレン−塩化ビニリデン共重合体、エチレン−アクリロニトリル共重合体、エチレン−メタクリロニトリル共重合体、エチレン−酢酸ビニル共重合体、エチレン−アクリルアミド共重合体、エチレン−メタクリルアミド共重合体、エチレン−アクリル酸共重合体、エチレン−メタクリル酸共重合体、エチレン−マレイン酸共重合体、エチレン−メチル(メタ)アクリレート共重合体、エチレン−エチル(メタ)アクリルレート共重合体、エチレン−イソプロピル(メタ)アクリレート共重合体、エチレン−(メタ)アクリレート共重合体、エチレン−イソブチル(メタ)アクリレート共重合体、エチレン−2−エチルヘキシル(メタ)アクリレート共重合体、エチレン−無水マレイン酸共重合体、エチレン−エチルアクリレート−無水マレイン酸共重合体、エチレン−(メタ)アクリル酸金属塩共重合体、エチレン−酢酸ビニル共重合体またはその鹸化物、エチレン−ビニルプロピオネート共重合体、エチレン−グリシジル(メタ)アクリレート共重合体、エチレン−エチルアクリレート−グリシジルメタクリレート共重合体、エチレン−酢酸ビニル−グリシジルメタクリレート共重合体などのエチレンまたはα−オレフィン−ビニル単量体共重合体;塩素化ポリプロピレン、塩素化ポリエチレンなどの塩素化ポリオレフィン等が挙げられる。 Further, a polyolefin resin into which a polar group has been introduced can also be used. Specific examples of polyolefin resins having polar groups introduced include maleic anhydride modified polyethylene, maleic acid modified polyethylene, acrylic acid modified polyethylene, maleic anhydride modified polypropylene, maleic anhydride modified polypropylene, maleic anhydride modified ethylene-propylene copolymer. Polymers, acid-modified polyolefins such as acrylic acid-modified polypropylene; ethylene-vinyl chloride copolymer, ethylene-vinylidene chloride copolymer, ethylene-acrylonitrile copolymer, ethylene-methacrylonitrile copolymer, ethylene-vinyl acetate copolymer Copolymer, ethylene-acrylamide copolymer, ethylene-methacrylamide copolymer, ethylene-acrylic acid copolymer, ethylene-methacrylic acid copolymer, ethylene-maleic acid copolymer, ethylene-methyl (meth) a Relate copolymer, ethylene-ethyl (meth) acrylate copolymer, ethylene-isopropyl (meth) acrylate copolymer, ethylene- (meth) acrylate copolymer, ethylene-isobutyl (meth) acrylate copolymer, ethylene 2-ethylhexyl (meth) acrylate copolymer, ethylene-maleic anhydride copolymer, ethylene-ethyl acrylate-maleic anhydride copolymer, ethylene- (meth) acrylic acid metal salt copolymer, ethylene-vinyl acetate Copolymer or saponified product thereof, ethylene-vinyl propionate copolymer, ethylene-glycidyl (meth) acrylate copolymer, ethylene-ethyl acrylate-glycidyl methacrylate copolymer, ethylene-vinyl acetate-glycidyl methacrylate copolymer Etc. Or α- olefin - vinyl monomer copolymer, chlorinated polypropylene, chlorinated polyolefins such as chlorinated polyethylene.
これらポリオレフィン樹脂(A)は、単独で用いてもまたは2種以上を組み合わせて用いてもよい。また、上記ポリオレフィン樹脂(A)が共重合体である場合、共重合体の形態は特に限定されず、交互共重合体、ランダム共重合体、ブロック共重合体、グラフト共重合体のいずれであってもよい。 These polyolefin resins (A) may be used alone or in combination of two or more. Further, when the polyolefin resin (A) is a copolymer, the form of the copolymer is not particularly limited, and may be any of an alternating copolymer, a random copolymer, a block copolymer, and a graft copolymer. May be.
上記ポリオレフィン樹脂(A)には、必要に応じて、他の樹脂またはゴムを本発明の効果を損なわない範囲内で添加してもよい。 If necessary, other resins or rubbers may be added to the polyolefin resin (A) as long as the effects of the present invention are not impaired.
前記の他の樹脂またはゴムとしては、例えば、プロピレン/ブテン−1共重合体などのα−オレフィン共重合体;エチレン/プロピレン/5−エチリデン−2−ノルボルネン共重合体などのエチレンまたはα−オレフィン−α−オレフィン−ジエン単量体共重合体;ポリブタジエン、ポリイソプレンなどのポリジエン;スチレン−ブタジエン共重合体などのビニル単量体−ジエン共重合体;スチレン−ブタジエン−スチレンブロック共重合体などのビニル単量体−ジエン−ビニル単量体ブロック共重合体;水素化(スチレン−ブタジエンランダム共重合体)などの水素化(ビニル単量体−ジエンランダム共重合体);水素化(スチレン−ブタジエン−スチレンブロック共重合体)などの水素化(ビニル単量体−ジエン−ビニル単量体ブロック共重合体);アクリロニトリル−ブタジエン−スチレングラフト共重合体、メチルメタクリレート−ブタジエン−スチレングラフト共重合体などのビニル単量体−ジエン−ビニル単量体グラフト共重合体;ポリ塩化ビニル、ポリ塩化ビニリデン、ポリアクリロニトリル、ポリ酢酸ビニル、ポリアクリル酸エチル、ポリアクリル酸ブチル、ポリメタクリル酸メチル、ポリスチレンなどのビニル重合体;塩化ビニル−アクリロニトリル共重合体、塩化ビニル−酢酸ビニル共重合体、アクリロニトリル−スチレン共重合体、メチルメタクリレート−スチレン共重合体などのビニル共重合体等が挙げられる。 Examples of the other resin or rubber include α-olefin copolymers such as propylene / butene-1 copolymer; ethylene or α-olefin such as ethylene / propylene / 5-ethylidene-2-norbornene copolymer. -Α-olefin-diene monomer copolymer; polydiene such as polybutadiene and polyisoprene; vinyl monomer-diene copolymer such as styrene-butadiene copolymer; styrene-butadiene-styrene block copolymer, etc. Vinyl monomer-diene-vinyl monomer block copolymer; Hydrogenation (vinyl monomer-diene random copolymer) such as hydrogenation (styrene-butadiene random copolymer); Hydrogenation (styrene-butadiene) -Styrene block copolymer) and other hydrogenation (vinyl monomer-diene-vinyl monomer block copolymer) A vinyl monomer-diene-vinyl monomer graft copolymer such as acrylonitrile-butadiene-styrene graft copolymer and methyl methacrylate-butadiene-styrene graft copolymer; polyvinyl chloride, polyvinylidene chloride, poly Vinyl polymers such as acrylonitrile, polyvinyl acetate, polyethyl acrylate, polybutyl acrylate, polymethyl methacrylate, and polystyrene; vinyl chloride-acrylonitrile copolymer, vinyl chloride-vinyl acetate copolymer, acrylonitrile-styrene copolymer And vinyl copolymers such as methyl methacrylate-styrene copolymer.
これらポリオレフィン樹脂(A)の中でも、乳化性および乾燥皮膜の強度の観点から、無水マレイン酸変性ポリプロピレン、無水マレイン酸変性エチレン−プロピレン共重合体、アクリル酸変性ポリプロピレンが好ましい。 Among these polyolefin resins (A), maleic anhydride-modified polypropylene, maleic anhydride-modified ethylene-propylene copolymer, and acrylic acid-modified polypropylene are preferable from the viewpoints of emulsifiability and dry film strength.
ポリオレフィン樹脂(A)は市販品を用いてもよいし合成品を用いてもよい。市販品の例としては、例えば、EASTMAN G3216、EASTMAN G3003、 EASTMAN G3015(以上、EASTMAN CHEMICAL COMPANY製)、POLYBOND(登録商標)3200、POLYBOND(登録商標)1001(以上、Chemtura Corporation社製)、ハイワックス(登録商標) NP0555A(三井化学株式会社製)、Exxelor(登録商標)PO 1015、Exxelor(登録商標)PO 1020(以上、Exxonmobil Chemical社製)、TOYOTAC(登録商標)H1000P、TOYOTAC(登録商標)H3000P(以上、東洋紡績株式会社製)、ユーメックス(登録商標)1001(三洋化成工業株式会社製)等が挙げられる。また、合成するための重合方法は特に制限されず、公知の方法を用いることができ、例えば、高圧ラジカル重合法、中低圧重合法、溶液重合法、スラリー重合法、塊状重合法、気相重合法等を挙げることができる。また、重合に使用する触媒も特に制限はなく、例えば、過酸化物触媒、チーグラー−ナッタ触媒、メタロセン触媒等が挙げられる。 As the polyolefin resin (A), a commercially available product or a synthetic product may be used. Examples of commercially available products include, for example, EASTMAN G3216, EASTMAN G3003, EASTMAN G3015 (manufactured by EASTMAN CHEMICAL COMPANY), POLYBOND (registered trademark) 3200, POLYBOND (registered trademark) 1001 (manufactured by Chemtora Corp. (Registered trademark) NP0555A (manufactured by Mitsui Chemicals, Inc.), Exxelor (registered trademark) PO 1015, Exxelor (registered trademark) PO 1020 (above, manufactured by Exxonbil Chemical), TOYOTAC (registered trademark) H1000P, TOYOTAC (registered trademark) H3000P (Above, manufactured by Toyobo Co., Ltd.), Umex (registered trademark) 1001 (manufactured by Sanyo Chemical Industries, Ltd.) Can be mentioned. The polymerization method for synthesis is not particularly limited, and a known method can be used. For example, a high-pressure radical polymerization method, a medium-low pressure polymerization method, a solution polymerization method, a slurry polymerization method, a bulk polymerization method, a gas phase polymerization method, and the like. Legal etc. can be mentioned. The catalyst used for the polymerization is not particularly limited, and examples thereof include peroxide catalysts, Ziegler-Natta catalysts, metallocene catalysts, and the like.
[高分子分散剤]
本発明で用いられる高分子分散剤(B)は、不飽和カルボン酸(b−1)および(メタ)アクリルアミド単量体(b−2)を含む単量体成分を共重合して得られるポリマーである。高分子分散剤(B)の形態は特に限定されず、交互共重合体、ランダム共重合体、ブロック共重合体、グラフト共重合体のいずれであってもよい。
[Polymer dispersant]
The polymer dispersant (B) used in the present invention is a polymer obtained by copolymerizing monomer components containing an unsaturated carboxylic acid (b-1) and a (meth) acrylamide monomer (b-2). It is. The form of the polymer dispersant (B) is not particularly limited, and may be any of an alternating copolymer, a random copolymer, a block copolymer, and a graft copolymer.
<不飽和カルボン酸>
本発明の高分子分散剤の(b−1)成分である不飽和カルボン酸の例としては、例えば、アクリル酸、メタクリル酸、クロトン酸、イタコン酸、マレイン酸、無水マレイン酸、フマル酸、シトラコン酸、無水シトラコン酸、メサコン酸などが挙げられる。これらは単独でも、または2種以上組み合わせても用いることができる。これらの中でも、メタクリル酸、イタコン酸が好ましい。
<Unsaturated carboxylic acid>
Examples of the unsaturated carboxylic acid that is the component (b-1) of the polymer dispersant of the present invention include, for example, acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, maleic anhydride, fumaric acid, citracone Examples include acid, citraconic anhydride, and mesaconic acid. These may be used alone or in combination of two or more. Among these, methacrylic acid and itaconic acid are preferable.
高分子分散剤中の(b−1)成分の量は、(b−1)成分と(b−2)成分との合計を100質量部として3.5〜90質量部であり、好ましくは7〜80質量部であり、より好ましくは30〜70質量部である。(b−1)成分の量が3.5質量部未満であるとポリオレフィン樹脂(A)の分散性が不足となり、一方、90質量部を超えると、高分子分散剤の粘度が高くなりハンドリング性に劣るようになる。 The amount of the component (b-1) in the polymer dispersant is 3.5 to 90 parts by mass, preferably 7 to 100 parts by mass of the total of the components (b-1) and (b-2). It is -80 mass parts, More preferably, it is 30-70 mass parts. When the amount of the component (b-1) is less than 3.5 parts by mass, the dispersibility of the polyolefin resin (A) becomes insufficient. On the other hand, when it exceeds 90 parts by mass, the viscosity of the polymer dispersant increases and handling properties are increased. Become inferior.
<(メタ)アクリルアミド単量体>
本発明の高分子分散剤の(b−2)成分である(メタ)アクリルアミド単量体の例としては、例えば、(メタ)アクリルアミド、N−メチル(メタ)アクリルアミド、N−エチル(メタ)アクリルアミド、N−プロピル(メタ)アクリルアミド、N−n−ブチル(メタ)アクリルアミド、N−tert−ブチル(メタ)アクリルアミド、N−ブトキシメチル(メタ)アクリルアミド、N−イソプロピル(メタ)アクリルアミド、N−メチロール(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、N,N−ジエチル(メタ)アクリルアミド、N−メチル−N−エチル(メタ)アクリルアミド、N−ヒドロキシエチル(メタ)アクリルアミド、N−ヒドロキシエチル−N−メチル(メタ)アクリルアミド、(メタ)アクリロイルモルフォリンなどが挙げられる。これらは単独でも、または2種以上組み合わせても用いることができる。これらの中でも、分散剤の水溶液中での安定性を得る観点から、(メタ)アクリルアミド、N−ヒドロキシエチル(メタ)アクリルアミドが好ましい。
<(Meth) acrylamide monomer>
Examples of the (meth) acrylamide monomer that is the component (b-2) of the polymer dispersant of the present invention include (meth) acrylamide, N-methyl (meth) acrylamide, and N-ethyl (meth) acrylamide. N-propyl (meth) acrylamide, Nn-butyl (meth) acrylamide, N-tert-butyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-methylol ( (Meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-methyl-N-ethyl (meth) acrylamide, N-hydroxyethyl (meth) acrylamide, N-hydroxyethyl- N-methyl (meth) acrylamide, (meth) acryloyl Such as morpholine and the like. These may be used alone or in combination of two or more. Among these, (meth) acrylamide and N-hydroxyethyl (meth) acrylamide are preferable from the viewpoint of obtaining stability of the dispersant in an aqueous solution.
高分子分散剤中の(b−2)成分の量は、(b−1)成分と(b−2)成分との合計を100質量部として10〜96.5質量部であり、好ましくは20〜93質量部であり、より好ましくは30〜70質量部である。(b−2)成分の量が10質量部未満であると親水性不足となり、一方、96.5質量部を超えると、ポリオレフィン樹脂(A)の分散性が低下する。 The amount of the component (b-2) in the polymer dispersant is 10 to 96.5 parts by mass with 100 parts by mass of the sum of the components (b-1) and (b-2), preferably 20 It is -93 mass parts, More preferably, it is 30-70 mass parts. When the amount of the component (b-2) is less than 10 parts by mass, the hydrophilicity is insufficient. On the other hand, when it exceeds 96.5 parts by mass, the dispersibility of the polyolefin resin (A) decreases.
本発明で用いられる高分子分散剤は、必要に応じて他の単量体成分を含んでいてもよい。他の単量体成分の例としては、(メタ)アクリル酸エステル、エチレン性不飽和単量体等が挙げられる。これら他の単量体成分は、単独でもまたは2種以上組み合わせて用いてもよい。以下、他の単量体成分について説明する。 The polymer dispersant used in the present invention may contain other monomer components as necessary. Examples of other monomer components include (meth) acrylic acid esters and ethylenically unsaturated monomers. These other monomer components may be used alone or in combination of two or more. Hereinafter, other monomer components will be described.
<(メタ)アクリル酸エステル>
本発明で用いられる(メタ)アクリル酸エステルは特に制限されないが、エステル部分に炭素数1〜22の直鎖状、分枝状、または環状のアルキル基を有する(メタ)アクリル酸エステルが好ましい。
<(Meth) acrylic acid ester>
The (meth) acrylic acid ester used in the present invention is not particularly limited, but a (meth) acrylic acid ester having a linear, branched or cyclic alkyl group having 1 to 22 carbon atoms in the ester portion is preferable.
エステル部分に炭素数1〜22の直鎖状、分枝状、または環状のアルキル基を有する(メタ)アクリル酸エステルの例としては、例えば、メチル(メタ)アクリレート、エチル(メタ)アクリレート、n−プロピル(メタ)アクリレート、イソプロピル(メタ)アクリレート、n−ブチル(メタ)アクリレート、イソブチル(メタ)アクリレート、sec−ブチル(メタ)アクリレート、tert−ブチル(メタ)アクリレート、n−ペンチル(メタ)アクリレート、iso−アミル(メタ)アクリレート、tert−ペンチル(メタ)アクリレート、ネオペンチル(メタ)アクリレート、n−へキシル(メタ)アクリレート、3−メチルペンタン−2−イル(メタ)アクリレート、3−メチルペンタン−3−イル(メタ)アクリレート、4−メチルペンチル(メタ)アクリレート、4−メチルペンタン−2−イル(メタ)アクリレート、1,3−ジメチルブチル(メタ)アクリレート、3,3−ジメチルブチル(メタ)アクリレート、3,3−ジメチルブタン−2−イル(メタ)アクリレート、n−ヘプチル(メタ)アクリレート、1−メチルヘキシル(メタ)アクリレート、3−メチルヘキシル(メタ)アクリレート、4−メチルヘキシル(メタ)アクリレート、5−メチルヘキシル(メタ)アクリレート、1−エチルペンチル(メタ)アクリレート、1−(n−プロピル)ブチル(メタ)アクリレート、1,1−ジメチルペンチル(メタ)アクリレート、1,4−ジメチルペンチル(メタ)アクリレート、1,1−ジエチルプロピル(メタ)アクリレート、1,3,3−トリメチルブチル(メタ)アクリレート、1−エチル−2,2−ジメチルプロピル(メタ)アクリレート、n−オクチル(メタ)アクリレート、1−メチルヘプチル(メタ)アクリレート、2−メチルヘプチル(メタ)アクリレート、5−メチルヘプチル(メタ)アクリレート、1−エチルヘキシル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、1−プロピルペンチル(メタ)アクリレート、2−プロピルペンチル(メタ)アクリレート、1,1−ジメチルヘキシル(メタ)アクリレート、1,4−ジメチルヘキシル(メタ)アクリレート、1,5−ジメチルヘキシル(メタ)アクリレート、1−エチル−1−メチルペンチル(メタ)アクリレート、1−エチル−4−メチルペンチル(メタ)アクリレート、1,1,4−トリメチルペンチル(メタ)アクリレート、2,4,4−トリメチルペンチル(メタ)アクリレート、1−イソプロピル−1,2−ジメチルプロピル(メタ)アクリレート、1,1,3,3−テトラメチルブチル(メタ)アクリレート、n−ノニル(メタ)アクリレート、1−メチルオクチル(メタ)アクリレート、6−メチルオクチル(メタ)アクリレート、1−エチルヘプチル(メタ)アクリレート、n−デシル(メタ)アクリレート、1−メチルノニル(メタ)アクリレート、1−エチルオクチル(メタ)アクリレート、1−(n−ブチル)ヘキシル(メタ)アクリレート、1,1−ジメチルオクチル(メタ)アクリレート、3,7−ジメチルオクチル(メタ)アクリレート、n−ウンデシル(メタ)アクリレート、1−メチルデシル(メタ)アクリレート、1−エチルノニル(メタ)アクリレート、n−ドデシル(メタ)アクリレート、n−トリデシル(メタ)アクリレート、n−テトラデシル(メタ)アクリレート、1−メチルトリデシル(メタ)アクリレート、n−ペンタデシル(メタ)アクリレート、n−ヘキサデシル(メタ)アクリレート、n−ヘプタデシル(メタ)アクリレート、n−オクタデシル(メタ)アクリレート、n−ノナデシル(メタ)アクリレート、n−エイコシル(メタ)アクリレート、シクロペンチル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、メチルシクロヘキシル(メタ)アクリレート、トリメチルシクロヘキシル(メタ)アクリレート、ノルボルニル(メタ)アクリレート、ノルボルニルメチル(メタ)アクリレート、シアノノルボルニル(メタ)アクリレート、イソボルニル(メタ)アクリレート、ボルニル(メタ)アクリレート、メンチル(メタ)アクリレート、フェンチル(メタ)アクリレート、アダマンチル(メタ)アクリレート、ジメチルアダマンチル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デカ−8−イル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デカ−4−メチル(メタ)アクリレート、シクロデシル(メタ)アクリレートなどが挙げられ、これらは単独でもまたは2種以上組み合わせても用いることができる。これらの中でも、n−ブチル(メタ)アクリレート、n−ヘキシル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレート、シクロヘキシル(メタ)アクリレートが好ましい。特に、乾燥後の皮膜強度調整および得られる分散剤の乳化性の観点から、シクロヘキシル(メタ)アクリレートと、n−ブチル(メタ)アクリレートまたは2−エチルヘキシル(メタ)アクリレートとを併用することがより好ましい。 Examples of (meth) acrylic acid esters having a linear, branched or cyclic alkyl group having 1 to 22 carbon atoms in the ester moiety include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, n -Propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, n-pentyl (meth) acrylate , Iso-amyl (meth) acrylate, tert-pentyl (meth) acrylate, neopentyl (meth) acrylate, n-hexyl (meth) acrylate, 3-methylpentan-2-yl (meth) acrylate, 3-methylpentane- 3-yl (meth) acrylate, 4 Methylpentyl (meth) acrylate, 4-methylpentan-2-yl (meth) acrylate, 1,3-dimethylbutyl (meth) acrylate, 3,3-dimethylbutyl (meth) acrylate, 3,3-dimethylbutane-2 -Yl (meth) acrylate, n-heptyl (meth) acrylate, 1-methylhexyl (meth) acrylate, 3-methylhexyl (meth) acrylate, 4-methylhexyl (meth) acrylate, 5-methylhexyl (meth) acrylate 1-ethylpentyl (meth) acrylate, 1- (n-propyl) butyl (meth) acrylate, 1,1-dimethylpentyl (meth) acrylate, 1,4-dimethylpentyl (meth) acrylate, 1,1-diethyl Propyl (meth) acrylate, 1,3,3-tri Tylbutyl (meth) acrylate, 1-ethyl-2,2-dimethylpropyl (meth) acrylate, n-octyl (meth) acrylate, 1-methylheptyl (meth) acrylate, 2-methylheptyl (meth) acrylate, 5-methyl Heptyl (meth) acrylate, 1-ethylhexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 1-propylpentyl (meth) acrylate, 2-propylpentyl (meth) acrylate, 1,1-dimethylhexyl (meth) acrylate 1,4-dimethylhexyl (meth) acrylate, 1,5-dimethylhexyl (meth) acrylate, 1-ethyl-1-methylpentyl (meth) acrylate, 1-ethyl-4-methylpentyl (meth) acrylate, 1 , 1,4-tri Methylpentyl (meth) acrylate, 2,4,4-trimethylpentyl (meth) acrylate, 1-isopropyl-1,2-dimethylpropyl (meth) acrylate, 1,1,3,3-tetramethylbutyl (meth) acrylate , N-nonyl (meth) acrylate, 1-methyloctyl (meth) acrylate, 6-methyloctyl (meth) acrylate, 1-ethylheptyl (meth) acrylate, n-decyl (meth) acrylate, 1-methylnonyl (meth) Acrylate, 1-ethyloctyl (meth) acrylate, 1- (n-butyl) hexyl (meth) acrylate, 1,1-dimethyloctyl (meth) acrylate, 3,7-dimethyloctyl (meth) acrylate, n-undecyl ( (Meth) acrylate, 1-methyldecyl (meth) ) Acrylate, 1-ethylnonyl (meth) acrylate, n-dodecyl (meth) acrylate, n-tridecyl (meth) acrylate, n-tetradecyl (meth) acrylate, 1-methyltridecyl (meth) acrylate, n-pentadecyl (meth) ) Acrylate, n-hexadecyl (meth) acrylate, n-heptadecyl (meth) acrylate, n-octadecyl (meth) acrylate, n-nonadecyl (meth) acrylate, n-eicosyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (Meth) acrylate, methylcyclohexyl (meth) acrylate, trimethylcyclohexyl (meth) acrylate, norbornyl (meth) acrylate, norbornylmethyl (meth) acrylate, Nonorbornyl (meth) acrylate, isobornyl (meth) acrylate, bornyl (meth) acrylate, menthyl (meth) acrylate, fentyl (meth) acrylate, adamantyl (meth) acrylate, dimethyladamantyl (meth) acrylate, tricyclo [5.2.1 0.0 2,6 ] dec-8-yl (meth) acrylate, tricyclo [5.2.1.0 2,6 ] dec-4-methyl (meth) acrylate, cyclodecyl (meth) acrylate, and the like. Can be used alone or in combination of two or more. Among these, n-butyl (meth) acrylate, n-hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, and cyclohexyl (meth) acrylate are preferable. In particular, it is more preferable to use cyclohexyl (meth) acrylate and n-butyl (meth) acrylate or 2-ethylhexyl (meth) acrylate in combination from the viewpoint of film strength adjustment after drying and emulsifying properties of the resulting dispersant. .
単量体成分が上記の(メタ)アクリル酸エステル成分をさらに含む場合の含有量は、(b−1)成分と(b−2)成分との合計を100質量部として、2〜90質量部であることが好ましく、25〜85質量部であることがより好ましい。かような範囲であれば、ハンドリング性と乳化性を両立した分散剤を得ることができる。 The content in the case where the monomer component further contains the (meth) acrylic acid ester component is 2 to 90 parts by mass with 100 parts by mass of the sum of the (b-1) component and the (b-2) component. It is preferable that it is 25-85 mass parts. If it is such a range, the dispersing agent which compatible handling property and emulsification property can be obtained.
<エチレン性不飽和単量体>
エチレン性不飽和単量体の例としては、例えば、1,3−ブタジエン、イソプレン等のジエン化合物;ビニルスルホン酸、メチルビニルスルホン酸、p−スチレンスルホン酸、(メタ)アリルスルホン酸、(メタ)アクリルスルホン酸、(メタ)アクリル酸−2−スルホン酸エチル、2−アクリルアミド−2−ヒドロキシプロパンスルホン酸等のエチレン性不飽和スルホン酸もしくはその塩;塩化ビニル、臭化ビニル、塩化ビニリデン等のハロゲン化ビニル単量体;スチレン、α−メチルスチレン、ビニルトルエン、2,4−ジメチルスチレン、ハロゲンで核置換されたスチレン、1−ビニルナフタレン、p−メチルスチレン、p−プロピルスチレン、p−シクロヘキシルスチレン、p−ドデシルスチレン等の芳香族ビニル単量体;酢酸ビニル等が挙げられる。
<Ethylenically unsaturated monomer>
Examples of the ethylenically unsaturated monomer include diene compounds such as 1,3-butadiene and isoprene; vinyl sulfonic acid, methyl vinyl sulfonic acid, p-styrene sulfonic acid, (meth) allyl sulfonic acid, (meta ) Ethylenically unsaturated sulfonic acids such as acrylic sulfonic acid, (meth) acrylic acid-2-ethyl sulfonate, 2-acrylamido-2-hydroxypropane sulfonic acid or salts thereof; vinyl chloride, vinyl bromide, vinylidene chloride, etc. Halogenated vinyl monomers: styrene, α-methylstyrene, vinyltoluene, 2,4-dimethylstyrene, styrene nucleus-substituted with halogen, 1-vinylnaphthalene, p-methylstyrene, p-propylstyrene, p-cyclohexyl Aromatic vinyl monomers such as styrene and p-dodecylstyrene; vinyl acetate Etc. The.
単量体成分が上記のエチレン性不飽和単量体成分をさらに含む場合の含有量は、(b−1)成分と(b−2)成分との合計を100質量部として、6.5〜67.0質量部であることが好ましく、8.0〜20質量部であることがより好ましい。かような範囲であれば、分散剤の機械的安定性を向上させることができる。 The content in the case where the monomer component further contains the above ethylenically unsaturated monomer component is 6.5 to 100 parts by mass of the sum of the component (b-1) and the component (b-2). The amount is preferably 67.0 parts by mass, and more preferably 8.0 to 20 parts by mass. If it is such a range, the mechanical stability of a dispersing agent can be improved.
高分子分散剤(B)は、市販品を用いてもよいし合成品を用いてもよい。合成する場合は、溶液重合、乳化重合、懸濁重合など従来公知の重合方法により合成することができる。溶液重合の場合は水、メチルアルコール、エチルアルコール、イソプロピルアルコール、t−ブチルアルコールなどの低級アルコール類やアセトン、メチルエチルケトン、ジオキサン等の溶剤を、単独または2種以上組み合わせて使用して重合を行えばよい。乳化重合や懸濁重合の場合は、従来公知のアニオンおよび/またはノニオン界面活性剤を使用し、前記の溶剤中において重合を行えばよい。 As the polymer dispersant (B), a commercially available product or a synthetic product may be used. In the case of synthesis, it can be synthesized by a conventionally known polymerization method such as solution polymerization, emulsion polymerization or suspension polymerization. In the case of solution polymerization, polymerization may be performed using water, lower alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, and t-butyl alcohol, or solvents such as acetone, methyl ethyl ketone, and dioxane, either alone or in combination of two or more. Good. In the case of emulsion polymerization or suspension polymerization, a conventionally known anion and / or nonionic surfactant may be used and polymerization may be carried out in the solvent.
重合開始剤も、従来公知のものが使用できる。具体的には、例えば、過硫酸アンモニウム、過硫酸カリウム、過硫酸ナトリウムなどの過硫酸塩、これら過硫酸塩と還元剤との組み合わせによるレドックス系重合触媒、2,2’−アゾビスイソブチロニトリル(AIBN)2,2’−アゾビス−(2,4−ジメチルバレロニトリル)、1,1’−アゾビス(シクロヘキサン−1−カルボニトリル)、2,2’−アゾビス−4−メトキシ−2,4−ジメチルバレロニトリルなどのアゾ系もしくはジアゾ系触媒、または過酸化水素、t−ブチルパーオキサイド、ベンゾイルパーオキサイド、メチルエチルケトンパーオキサイド、ジイソプロピルパーオキシカーボネート、クメンヒドロパーオキサイド、t−ブチルヒドロパーオキサイド、ジ−t−ブチルパーオキサイド、ジクミルパーオキサイド、2,4−ジクロロベンゾイルパーオキサイド、ラウロイルパーオキサイド、2,2−ビス−(4,4−t−ブチルパーオキシシクロヘキシル)プロパン、トリス−(t−ブチルパーオキシ)トリアジンなどの過酸化物を挙げることができる。これら重合開始剤の使用量は特に制限されないが、単量体の合計量100質量部に対して、概ね0.01〜0.50質量部であることが好ましい。 A conventionally well-known thing can also be used for a polymerization initiator. Specifically, for example, persulfates such as ammonium persulfate, potassium persulfate, and sodium persulfate, redox polymerization catalysts based on a combination of these persulfates and a reducing agent, 2,2′-azobisisobutyronitrile. (AIBN) 2,2′-azobis- (2,4-dimethylvaleronitrile), 1,1′-azobis (cyclohexane-1-carbonitrile), 2,2′-azobis-4-methoxy-2,4- An azo or diazo catalyst such as dimethylvaleronitrile, or hydrogen peroxide, t-butyl peroxide, benzoyl peroxide, methyl ethyl ketone peroxide, diisopropyl peroxycarbonate, cumene hydroperoxide, t-butyl hydroperoxide, di- t-Butyl peroxide, Dicumyl peroxide Examples of peroxides such as 2,4-dichlorobenzoyl peroxide, lauroyl peroxide, 2,2-bis- (4,4-t-butylperoxycyclohexyl) propane, and tris- (t-butylperoxy) triazine be able to. Although the usage-amount of these polymerization initiators is not restrict | limited, It is preferable that it is about 0.01-0.50 mass part with respect to 100 mass parts of total amounts of a monomer.
高分子分散剤(B)を合成する際には、高分子分散剤(B)の分子量の調節をより容易にするために、分子量調節剤を用いることが好ましい。 When synthesizing the polymer dispersant (B), it is preferable to use a molecular weight modifier in order to make it easier to adjust the molecular weight of the polymer dispersant (B).
分子量調節剤としては、例えば、n−ドデシルメルカプタン、t−ドデシルメルカプタン、n−オクチルメルカプタン、ステアリルメルカプタン、チオフェノール、チオ安息香酸、チオサリチル酸、ナフタレンチオール、トルエンチオール、メルカプトエタノール、メルカプトプロパノール、メルカプトブタノール、メルカプトグリコール、チオグリセリン、システアミン塩酸もしくはその塩、メルカプトプロピオン酸もしくはその塩、チオグリコール酸もしくはその塩、チオ酢酸もしくはその塩、チオリンゴ酸もしくはその塩、メチル基、エチル基、プロピル基、ブチル基、メトキシブチル基、n−オクチル基、2−エチルヘキシル基などのアルキル基を有するチオグリコール酸エステルもしくはメルカプトプロピオン酸エステル、チオグリコール酸とエチレングリコール、トリメチロールプロパンなど多価アルコールとのエステル、ターピノーレン、α−メチルスチレン、またはα−メチルスチレンダイマー等が挙げられる。分子量調節剤の量は特に制限されないが、単量体の合計量100質量部に対して概ね0.1〜10質量部であることが好ましい。 Examples of the molecular weight regulator include n-dodecyl mercaptan, t-dodecyl mercaptan, n-octyl mercaptan, stearyl mercaptan, thiophenol, thiobenzoic acid, thiosalicylic acid, naphthalene thiol, toluene thiol, mercaptoethanol, mercaptopropanol, mercaptobutanol. , Mercaptoglycol, thioglycerin, cysteamine hydrochloride or its salt, mercaptopropionic acid or its salt, thioglycolic acid or its salt, thioacetic acid or its salt, thiomalic acid or its salt, methyl group, ethyl group, propyl group, butyl group Thioglycolic acid ester or mercaptopropionic acid ester having an alkyl group such as methoxybutyl group, n-octyl group, 2-ethylhexyl group, Cholic acid and ethylene glycol, esters of polyhydric alcohols such as trimethylolpropane, terpinolene, alpha-methylstyrene or alpha-methylstyrene dimer or the like, can be mentioned. The amount of the molecular weight regulator is not particularly limited, but is preferably about 0.1 to 10 parts by mass with respect to 100 parts by mass of the total amount of monomers.
重合時間や重合温度も特に制限されないが、一例をあげれば、重合時間は2〜7時間の範囲であり、重合温度は70〜90℃の範囲である。 The polymerization time and the polymerization temperature are not particularly limited. For example, the polymerization time is in the range of 2 to 7 hours, and the polymerization temperature is in the range of 70 to 90 ° C.
得られた共重合体(高分子分散剤)は、必要に応じて共重合体中の不飽和カルボン酸部分を、無機アルカリおよび/または有機アルカリにより中和してもよい。中和に用いる無機アルカリとしては、水酸化ナトリウム、水酸化カリウムなどが挙げられ、有機アルカリとしてはアンモニウム、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン等の有機アミン類が挙げられる。該アルカリによる共重合体の中和は、完全中和であってもよいし部分中和であってもよい。 In the obtained copolymer (polymer dispersing agent), the unsaturated carboxylic acid moiety in the copolymer may be neutralized with an inorganic alkali and / or an organic alkali as necessary. Examples of the inorganic alkali used for neutralization include sodium hydroxide and potassium hydroxide, and examples of the organic alkali include organic amines such as ammonium, monoethanolamine, diethanolamine, and triethanolamine. The neutralization of the copolymer with the alkali may be complete neutralization or partial neutralization.
得られる高分子分散剤(B)の重量平均分子量(Mw)は、1,000〜700,000であることが好ましく、1,500〜500,000であることがより好ましい。重量平均分子量がこのような範囲であれば、ポリオレフィン樹脂(A)を効率良く分散させることができる。なお、高分子分散剤(B)の重量平均分子量は、後述の実施例に記載の方法により測定した値を採用するものとする。 The weight average molecular weight (Mw) of the resulting polymer dispersant (B) is preferably 1,000 to 700,000, more preferably 1,500 to 500,000. When the weight average molecular weight is in such a range, the polyolefin resin (A) can be efficiently dispersed. In addition, the value measured by the method as described in the below-mentioned Example shall be employ | adopted for the weight average molecular weight of a polymer dispersing agent (B).
高分子分散剤(B)は単離して用いてもよいし、溶液や水性分散液の形態で用いてもよい。ただし、本発明の水性分散体をより簡便に製造するという観点から、水性分散液の形態であることが好ましい。 The polymer dispersant (B) may be used after isolation, or may be used in the form of a solution or an aqueous dispersion. However, from the viewpoint of more easily producing the aqueous dispersion of the present invention, it is preferably in the form of an aqueous dispersion.
[水性分散体]
本発明の水性分散体は、上記の重量平均分子量が2万以上であるポリオレフィン樹脂(A)と、上記の高分子分散剤(B)とを含む。
[Aqueous dispersion]
The aqueous dispersion of the present invention contains the polyolefin resin (A) having a weight average molecular weight of 20,000 or more and the polymer dispersant (B).
本発明の水性分散体中のポリオレフィン樹脂(A)の含有量(濃度)は、水性分散体の全質量に対して、10〜40質量%であることが好ましく、20〜30質量%であることがより好ましい。また、高分子分散剤(B)の含有量は、ポリオレフィン樹脂(A)の量を100質量部として、1〜35質量部が好ましく、3〜15質量部がより好ましい。 The content (concentration) of the polyolefin resin (A) in the aqueous dispersion of the present invention is preferably 10 to 40% by mass, and preferably 20 to 30% by mass with respect to the total mass of the aqueous dispersion. Is more preferable. Moreover, 1-35 mass parts is preferable and, as for content of a polymer dispersing agent (B), the quantity of polyolefin resin (A) is 100 mass parts, and 3-15 mass parts is more preferable.
本発明の水性分散体の製造方法は特に制限されないが、例えば、オートクレーブなどの加圧可能で通常の剪断力を有する装置に、ポリオレフィン樹脂(A)、高分子分散剤(B)、水性媒体、および必要に応じて乳化剤や中和剤等を仕込み、ポリオレフィン樹脂(A)の軟化温度付近または軟化温度以上の温度まで加熱し撹拌することによって得られる。ここで、水性媒体とは、水を主成分とする液体であり、水溶性の有機溶剤を含有していてもよい。 The method for producing the aqueous dispersion of the present invention is not particularly limited. For example, a polyolefin resin (A), a polymer dispersant (B), an aqueous medium, And if necessary, an emulsifier, a neutralizing agent, etc. are prepared, and it is obtained by heating and stirring near the softening temperature of the polyolefin resin (A) or higher than the softening temperature. Here, the aqueous medium is a liquid containing water as a main component and may contain a water-soluble organic solvent.
使用できる有機溶剤の具体例としては、例えば、メタノール、エタノール、n−プロピルアルコール、イソプロピルアルコール、n−ブチルアルコール、イソブチルアルコール、sec−ブチルアルコール、t−ブチルアルコール、n−アミルアルコール、イソアミルアルコール、sec−アミルアルコール、t−アミルアルコール、1−エチル−1−プロパノール、2−メチル−1−ブチルアルコール、n−ヘキシルアルコール、シクロヘキシルアルコール等のアルコール類、メチルエチルケトン、メチルイソブチルケトン、エチルブチルケトン、シクロヘキサノン等のケトン類、テトラヒドロフラン、ジオキサン等のエーテル類、酢酸エチル、酢酸−n−プロピル、酢酸イソプロピル、酢酸−n−ブチル、酢酸イソブチル、酢酸−sec−ブチル、酢酸−3−メトキシブチル、プロピオン酸メチル、プロピオン酸エチル、炭酸ジエチル、炭酸ジメチル等のエステル類、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールエチルエーテルアセテート等のグリコール誘導体、さらには、1−メトキシ−2−プロパノール、1−エトキシ−2−プロパノール、3−メトキシ−3−メチル−1−ブタノール、メトキシブタノール、アセトニトリル、ジメチルホルムアミド、ジメチルアセトアミド、ジアセトンアルコール、アセト酢酸エチル、1,2−ジメチルグリセリン、1,3−ジメチルグリセリン、トリメチルグリセリン等が挙げられる。これらの有機溶剤は、単独でもまたは2種以上を混合して用いてもよい。 Specific examples of the organic solvent that can be used include, for example, methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, sec-butyl alcohol, t-butyl alcohol, n-amyl alcohol, isoamyl alcohol, alcohols such as sec-amyl alcohol, t-amyl alcohol, 1-ethyl-1-propanol, 2-methyl-1-butyl alcohol, n-hexyl alcohol, cyclohexyl alcohol, methyl ethyl ketone, methyl isobutyl ketone, ethyl butyl ketone, cyclohexanone Ketones such as tetrahydrofuran, dioxane, etc., ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, acetic acid-sec Esters such as butyl, 3-methoxybutyl acetate, methyl propionate, ethyl propionate, diethyl carbonate, dimethyl carbonate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, ethylene Glycol derivatives such as glycol ethyl ether acetate, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, 3-methoxy-3-methyl-1-butanol, methoxybutanol, acetonitrile, dimethylformamide, dimethylacetamide , Diacetone alcohol, ethyl acetoacetate, 1,2-dimethylglycerol, 1,3-dimethylglycerol, trimethylglycerol and the like. These organic solvents may be used alone or in admixture of two or more.
有機溶媒を用いる場合の添加量は特に制限されないが、水性媒体全体に対して0〜10質量部であることが好ましい。 The addition amount in the case of using an organic solvent is not particularly limited, but is preferably 0 to 10 parts by mass with respect to the entire aqueous medium.
乳化剤は特に制限されないが、乳化性、安全性および各種添加剤を加えた時のゲル化抑制の観点から、ノニオン界面活性剤を用いることが好ましい。 The emulsifier is not particularly limited, but it is preferable to use a nonionic surfactant from the viewpoint of emulsifying property, safety, and suppression of gelation when various additives are added.
ノニオン界面活性剤の例としては、例えば、ポリオキシエチレンオクチルエーテル、ポリオキシエチレンデシルエーテル、ポリオキシエチレンドデシルエーテル、ポリオキシエチレンミリスチルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンイソステアリルエーテル、ポリオキシエチレンベヘニルエーテル、ポリオキシエチレン−2−エチルヘキシルエーテル、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルエーテル(合成系)、ナロー型ポリオキシエチレンアルキルエーテル、ポリオキシエチレンオクチルドデシルエーテル、ポリオキシエチレンスチレン化フェニルエーテル、ポリオキシエチレンβ−ナフチルエーテル、ポリオキシエチレン硬化ヒマシ油エーテル、ポリエチレングリコールモノアルキル脂肪酸エステル、ポリエチレングリコール脂肪酸エステル、ポリオキシエチレンソルビタンモノラウリン酸エステル等が挙げられる。 Examples of nonionic surfactants include, for example, polyoxyethylene octyl ether, polyoxyethylene decyl ether, polyoxyethylene dodecyl ether, polyoxyethylene myristyl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene Oleyl ether, polyoxyethylene isostearyl ether, polyoxyethylene behenyl ether, polyoxyethylene-2-ethylhexyl ether, polyoxyethylene alkyl ether, polyoxyethylene alkyl ether (synthetic system), narrow type polyoxyethylene alkyl ether, poly Oxyethylene octyldodecyl ether, polyoxyethylene styrenated phenyl ether, polyoxyethylene β-naphthyl ester Ether, polyoxyethylene hydrogenated castor oil ether, polyethylene glycol monoalkyl fatty acid esters, polyethylene glycol fatty acid esters, polyoxyethylene sorbitan monolaurate, and the like.
さらに安定な水性分散体を得るために、乳化剤として上記ノニオン界面活性剤の他に、カチオン界面活性剤、アニオン界面活性剤、両性界面活性剤、反応性界面活性剤、または上記(B)成分以外の高分子分散剤等を併用してもよい。 In order to obtain a more stable aqueous dispersion, in addition to the above nonionic surfactant as an emulsifier, a cationic surfactant, an anionic surfactant, an amphoteric surfactant, a reactive surfactant, or other than the component (B) These polymer dispersants may be used in combination.
カチオン界面活性剤としては、例えば、ドデシルアミン酢酸塩、ステアリルアミン酢酸塩等の高級アルキルモノアミン塩、N−ドデシル−1,3−ジアミノプロパンアジピン酸塩、N−ドデシルプロピレンジアミンジオレイン酸塩等のアルキルジアミン塩、ドデシルトリメチルアンモニウムクロライド、ベヘニルトリメチルアンモニウムクロライド等の4級アンモニウム塩等が挙げられる。 Examples of the cationic surfactant include higher alkyl monoamine salts such as dodecylamine acetate and stearylamine acetate, N-dodecyl-1,3-diaminopropane adipate, and N-dodecylpropylenediamine dioleate. Examples thereof include quaternary ammonium salts such as alkyldiamine salts, dodecyltrimethylammonium chloride, and behenyltrimethylammonium chloride.
アニオン界面活性剤としては、半硬化牛脂脂肪酸石鹸ナトリウム塩、ステアリン酸石鹸ナトリウム塩、オレイン酸石鹸カリウム塩、ガムロジン系不均化ロジンナトリウム塩、アルケニルコハク酸ジカリウム塩、ドデシル硫酸エステルナトリウム塩、無水重亜硫酸ソーダ、ポリオキシエチレンアルキル(C12,C13)エーテル硫酸エステルナトリウム塩、ポリオキシエチレンドデシル硫酸エステルアンモニウム塩、ドデシルベンゼンスルホン酸ソーダ等が挙げられる。 Anionic surfactants include semi-cured tallow fatty acid soap sodium salt, stearic acid soap sodium salt, oleic acid soap potassium salt, gum rosin disproportionated rosin sodium salt, alkenyl succinic acid dipotassium salt, dodecyl sulfate sodium salt, anhydrous heavy Examples include sodium sulfite, polyoxyethylene alkyl (C12, C13) ether sulfate sodium salt, polyoxyethylene dodecyl sulfate ammonium salt, and dodecylbenzene sulfonic acid soda.
両性界面活性剤としては、例えば、カルボキシベタイン系、スルホベタイン系、ホスホベタイン系、アミドアミノ酸系、イミダゾリニウムベタイン系界面活性剤等が挙げられる。 Examples of amphoteric surfactants include carboxybetaine-based, sulfobetaine-based, phosphobetaine-based, amide amino acid-based, and imidazolinium betaine-based surfactants.
反応性界面活性剤としては、例えば、アルキルプロペニルフェノールポリエチレンオキサイド付加物やこれらの硫酸エステル塩、アリルアルキルフェノールポリエチレンオキサイド付加物やこれらの硫酸エステル塩、アリルジアルキルフェノールポリエチレンオキサイド付加物やこれらの硫酸エステル塩等の反応性2重結合を有する化合物等が挙げられる。 Examples of reactive surfactants include alkylpropenylphenol polyethylene oxide adducts and their sulfate esters, allyl alkylphenol polyethylene oxide adducts and their sulfate esters, allyl dialkylphenol polyethylene oxide adducts and their sulfate esters. Examples thereof include compounds having a reactive double bond.
(B)成分以外の高分子分散剤としては、例えば、分子内に複数のカルボキシル基を有するポリカルボン酸系高分子分散剤、分子内に複数のアミノ基を有するポリアミン系高分子分散剤、分子内に複数のアミド基を有する高分子分散剤、分子内に複数の多環式芳香族化合物を含有する高分子分散剤などが挙げられる。 Examples of polymer dispersants other than the component (B) include polycarboxylic acid polymer dispersants having a plurality of carboxyl groups in the molecule, polyamine polymer dispersants having a plurality of amino groups in the molecule, and molecules. Examples thereof include a polymer dispersant having a plurality of amide groups therein, a polymer dispersant containing a plurality of polycyclic aromatic compounds in the molecule, and the like.
また、上記中和剤としては、例えば、水酸化カリウム、水酸化ナトリウム、水酸化マグネシウム、水酸化カルシウム、炭酸ナトリウム、重炭酸ナトリウム、炭酸カリウム、重炭酸カリウム、炭酸カルシウム、重炭酸カルシウム、炭酸マグネシウム、重炭酸マグネシウム、モノラウリルアミン、トリメチルアミン、ジメチルモノエタノールアミン、トリエタノールアミン、エチレンジアミン、アンモニア等があげられる。 Examples of the neutralizing agent include potassium hydroxide, sodium hydroxide, magnesium hydroxide, calcium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, calcium carbonate, calcium bicarbonate, magnesium carbonate. , Magnesium bicarbonate, monolaurylamine, trimethylamine, dimethylmonoethanolamine, triethanolamine, ethylenediamine, ammonia and the like.
本発明の水性分散体は、通常用いられる配合剤、例えば、酸化防止剤、表面処理剤、潤滑剤、滑剤(あるいは風合改良剤)、帯電防止剤、pH調整剤、紫外線吸収剤、光安定剤熱安定剤、消泡剤、老化防止剤、レベリング剤等をさらに含んでいてもよい。 The aqueous dispersion of the present invention contains commonly used compounding agents such as antioxidants, surface treatment agents, lubricants, lubricants (or texture improvers), antistatic agents, pH adjusters, ultraviolet absorbers, and light stabilizers. It may further contain an agent heat stabilizer, antifoaming agent, anti-aging agent, leveling agent and the like.
上記酸化防止剤の例としては、例えば、ハイドロキノン、メトキシハイドロキノン、カテコール、2,6−ジ−t−ブチル−p−クレゾール(BHT)、2,2’−メチレンビス(4−メチル−6−t−ブチルフェノール)等のフェノール系酸化防止剤;チオ尿素、テトラメチルチウラムジサルファイド、ジメチルジチオカルバミン酸およびその塩、亜硫酸ナトリウム、チオ硫酸ナトリウム、2−メルカプトベンゾチアゾールおよびその塩、ジラウリル3,3’−チオジプロピオネート(DLTDP)、ジステアリル3,3’−チオジプロピオネート(DSTDP)等の含硫黄化合物;トリフェニルホスファイト、トリエチルホスファイト、亜リン酸ナトリウム、次亜リン酸ナトリウム、トリフェニルホスファイト(TPP)、トリイソデシルホスファイト(TDP)等の含リン化合物;オクチル化ジフェニルアミン、N−n−ブチル−p−アミノフェノール、N,N−ジイソプロピル−p−フェニレンジアミン、尿素、グアニジンなどの含窒素化合物;等が挙げられる。 Examples of the antioxidant include hydroquinone, methoxyhydroquinone, catechol, 2,6-di-t-butyl-p-cresol (BHT), 2,2′-methylenebis (4-methyl-6-t-), for example. Phenolic antioxidants such as butylphenol); thiourea, tetramethylthiuram disulfide, dimethyldithiocarbamic acid and its salts, sodium sulfite, sodium thiosulfate, 2-mercaptobenzothiazole and its salts, dilauryl 3,3′-thiodipro Sulfur-containing compounds such as pionate (DLTDP) and distearyl 3,3′-thiodipropionate (DSTDP); triphenyl phosphite, triethyl phosphite, sodium phosphite, sodium hypophosphite, triphenyl phosphite (TPP), triisodecy Phosphorus-containing compounds such as phosphite (TDP); nitrogen-containing compounds such as octylated diphenylamine, Nn-butyl-p-aminophenol, N, N-diisopropyl-p-phenylenediamine, urea and guanidine; .
上記表面処理剤の例としては、例えば、アミノシラン系カップリング剤、エポキシシラン系カップリング剤、ビニルシラン系カップリング剤、メタクリロシラン系カップリング剤、ウレイドシラン系カップリング剤、ボラン系カップリング剤、チタネート系カップリング剤、アルミニウム系カップリング剤、クロム系カップリング剤、ジルコニウム系カップリング剤などのカップリング剤;コロイダルシリカ、コロイダルアルミナなどのコロイダルゲル等が挙げられる。 Examples of the surface treatment agent include, for example, amino silane coupling agents, epoxy silane coupling agents, vinyl silane coupling agents, methacrylo silane coupling agents, ureido silane coupling agents, and borane coupling agents. And coupling agents such as titanate coupling agents, aluminum coupling agents, chromium coupling agents, and zirconium coupling agents; colloidal gels such as colloidal silica and colloidal alumina.
上記潤滑剤としては、例えば、動植物油水添硬化物、パラフィンワックス、エステル系合成油などが挙げられる。 Examples of the lubricant include animal and vegetable oil hydrogenated cured products, paraffin wax, and ester-based synthetic oil.
上記滑剤(あるいは風合改良剤)としては、例えば、ブチルステアレート、テトラエチレンペンタミンジステアレート、水添ひまし油、イミダゾリン系脂肪酸アミド、カチオン性脂肪酸アミド、カチオン性ポリエチレンイミンポリアミド、ビスフェノールAポリ(オキシエチレン)エーテルグリコール等が挙げられる。 Examples of the lubricant (or texture improver) include butyl stearate, tetraethylenepentamine distearate, hydrogenated castor oil, imidazoline fatty acid amide, cationic fatty acid amide, cationic polyethyleneimine polyamide, bisphenol A poly (oxy). Ethylene) ether glycol and the like.
上記帯電防止剤としては、例えば、アニオン界面活性剤、カチオン界面活性剤等の各種界面活性剤が挙げられる。 Examples of the antistatic agent include various surfactants such as an anionic surfactant and a cationic surfactant.
上記pH調整剤としては、例えば、塩酸、硫酸、燐酸などの無機酸やクエン酸、コハク酸、りんご酸、乳酸などの有機酸等の酸、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸カリウム、モノエタノールアミン、ジエタノールアミン、トリエタノールアミン等のアルカリなどが挙げられる。 Examples of the pH adjuster include inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid, and acids such as citric acid, succinic acid, malic acid, and lactic acid, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate. And alkalis such as monoethanolamine, diethanolamine, and triethanolamine.
上記紫外線吸収剤としては、例えば、ベンゾフェノン系紫外線吸収剤、ベンゾトリアゾール系紫外線吸収剤、シアノクリレート系紫外線吸収剤、トリアジン系紫外線吸収剤、環状イミノエステル系紫外線吸収剤、フェニルサリシレート系紫外線吸収剤等が挙げられる。 Examples of the UV absorber include benzophenone UV absorbers, benzotriazole UV absorbers, cyanoacrylate UV absorbers, triazine UV absorbers, cyclic imino ester UV absorbers, and phenyl salicylate UV absorbers. Etc.
上記光安定剤としては、例えば、2,2,6,6−テトラメチル−4−ピペリジルステアレート、1,2,2,6,6−ペンタメチル−4−ピペリジルステアレート等のヒンダードアミン系光安定剤等が挙げられる。 Examples of the light stabilizer include hindered amine light stabilizers such as 2,2,6,6-tetramethyl-4-piperidyl stearate and 1,2,2,6,6-pentamethyl-4-piperidyl stearate. Etc.
さらに、本発明の水性分散体は、下記化学式(1)で表されるリン酸エステル化合物を含んでもよい。下記化学式(1)で表されるリン酸エステル化合物を含むことにより、本発明の水性分散体をガラス繊維用集束剤として用いた場合、ガラス繊維の集束性がより向上する。 Furthermore, the aqueous dispersion of the present invention may contain a phosphate compound represented by the following chemical formula (1). By including the phosphate ester compound represented by the following chemical formula (1), when the aqueous dispersion of the present invention is used as a sizing agent for glass fibers, the sizing property of the glass fibers is further improved.
前記化学式(1)中、Rは炭素数1〜22の直鎖状または分枝状のアルキル基であり、nは0〜30の整数であり、mは1〜3の整数であり、Mは水素原子、アルカリ金属、第2族金属、アンモニウム基、または有機アンモニウム基である。 In said chemical formula (1), R is a C1-C22 linear or branched alkyl group, n is an integer of 0-30, m is an integer of 1-3, M is A hydrogen atom, an alkali metal, a Group 2 metal, an ammonium group, or an organic ammonium group.
前記一般式(1)中のRで用いられる炭素数1〜22の直鎖状または分岐状のアルキル基の例としては、例えば、メチル基、エチル基、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、t−ブチル基、n−ペンチル基、iso−アミル基、t−ペンチル基、ネオペンチル基、n−へキシル基、3−メチルペンタン−2−イル基、3−メチルペンタン−3−イル基、4−メチルペンチル基、4−メチルペンタン−2−イル基、1,3−ジメチルブチル基、3,3−ジメチルブチル基、3,3−ジメチルブタン−2−イル基、n−ヘプチル基、1−メチルヘキシル基、3−メチルヘキシル基、4−メチルヘキシル基、5−メチルヘキシル基、1−エチルペンチル基、1−(n−プロピル)ブチル基、1,1−ジメチルペンチル基、1,4−ジメチルペンチル基、1,1−ジエチルプロピル基、1,3,3−トリメチルブチル基、1−エチル−2,2−ジメチルプロピル基、n−オクチル基、2−エチルヘキシル基、2−メチルヘキサン−2−イル基、2,4−ジメチルペンタン−3−イル基、1,1−ジメチルペンタン−1−イル基、2,2−ジメチルヘキサン−3−イル基、2,3−ジメチルヘキサン−2−イル基、2,5−ジメチルヘキサン−2−イル基、2,5−ジメチルヘキサン−3−イル基、3,4−ジメチルヘキサン−3−イル基、3,5−ジメチルヘキサン−3−イル基、1−メチルヘプチル基、2−メチルヘプチル基、5−メチルヘプチル基、2−メチルヘプタン−2−イル基、3−メチルヘプタン−3−イル基、4−メチルヘプタン−3−イル基、4−メチルヘプタン−4−イル基、1−エチルヘキシル基、2−エチルヘキシル基、1−プロピルペンチル基、2−プロピルペンチル基、1,1−ジメチルヘキシル基、1,4−ジメチルヘキシル基、1,5−ジメチルヘキシル基、1−エチル−1−メチルペンチル基、1−エチル−4−メチルペンチル基、1,1,4−トリメチルペンチル基、2,4,4−トリメチルペンチル基、2,3,4−トリメチルペンタン−3−イル基、1−イソプロピル−1,2−ジメチルプロピル基、1,1,3,3−テトラメチルブチル基、n−ノニル基、1−メチルオクチル基、6−メチルオクチル基、1−エチルヘプチル基、1−(n−ブチル)ペンチル基、4−メチル−1−(n−プロピル)ペンチル基、1,5,5−トリメチルヘキシル基、1,1,5−トリメチルヘキシル基、3,5,5−トリメチルヘキシル基、2−メチルオクタン−3−イル基、n−デシル基、イソデシル基、1−メチルノニル基、1−エチルオクチル基、1−(n−ブチル)ヘキシル基、1,1−ジメチルオクチル基、3,7−ジメチルオクチル基、3,7−ジメチルオクタン−3−イル基、n−ウンデシル基、1−メチルデシル基、1−エチルノニル基、n−ドデシル基、イソドデシル基、2−(n−ブチル)オクチル基、2,3,4,6,6−ペンタメチルヘプタン−3−イル基、n−トリデシル基、イソトリデシル基、n−テトラデシル基、イソテトラデシル基、2−(n−ヘキシル)オクチル基、1−メチルトリデシル基、n−ペンタデシル基、イソペンタデシル基、3,7,11−トリメチルドデシル基、n−ヘキサデシル基、n−ヘプタデシル基、n−オクタデシル基、イソステアリル基、n−ノナデシル基、n−エイコサデシル基、3,7,11,15−テトラメチルヘキサデシル基、ヘニコシル基、ドコシル基等が挙げられる。 Examples of the linear or branched alkyl group having 1 to 22 carbon atoms used for R in the general formula (1) include, for example, a methyl group, an ethyl group, a methyl group, an ethyl group, and an n-propyl group. , Isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group, iso-amyl group, t-pentyl group, neopentyl group, n-hexyl group, 3-methylpentane 2-yl group, 3-methylpentan-3-yl group, 4-methylpentyl group, 4-methylpentan-2-yl group, 1,3-dimethylbutyl group, 3,3-dimethylbutyl group, 3, 3-dimethylbutan-2-yl group, n-heptyl group, 1-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 1-ethylpentyl group, 1- (n- Propyl Butyl group, 1,1-dimethylpentyl group, 1,4-dimethylpentyl group, 1,1-diethylpropyl group, 1,3,3-trimethylbutyl group, 1-ethyl-2,2-dimethylpropyl group, n -Octyl group, 2-ethylhexyl group, 2-methylhexane-2-yl group, 2,4-dimethylpentan-3-yl group, 1,1-dimethylpentan-1-yl group, 2,2-dimethylhexane- 3-yl group, 2,3-dimethylhexane-2-yl group, 2,5-dimethylhexane-2-yl group, 2,5-dimethylhexane-3-yl group, 3,4-dimethylhexane-3- Yl group, 3,5-dimethylhexane-3-yl group, 1-methylheptyl group, 2-methylheptyl group, 5-methylheptyl group, 2-methylheptan-2-yl group, 3-methylheptane-3- B Group, 4-methylheptan-3-yl group, 4-methylheptan-4-yl group, 1-ethylhexyl group, 2-ethylhexyl group, 1-propylpentyl group, 2-propylpentyl group, 1,1-dimethylhexyl Group, 1,4-dimethylhexyl group, 1,5-dimethylhexyl group, 1-ethyl-1-methylpentyl group, 1-ethyl-4-methylpentyl group, 1,1,4-trimethylpentyl group, 2, 4,4-trimethylpentyl group, 2,3,4-trimethylpentan-3-yl group, 1-isopropyl-1,2-dimethylpropyl group, 1,1,3,3-tetramethylbutyl group, n-nonyl Group, 1-methyloctyl group, 6-methyloctyl group, 1-ethylheptyl group, 1- (n-butyl) pentyl group, 4-methyl-1- (n-propyl) pentyl group, 1, 5,5-trimethylhexyl group, 1,1,5-trimethylhexyl group, 3,5,5-trimethylhexyl group, 2-methyloctane-3-yl group, n-decyl group, isodecyl group, 1-methylnonyl group 1-ethyloctyl group, 1- (n-butyl) hexyl group, 1,1-dimethyloctyl group, 3,7-dimethyloctyl group, 3,7-dimethyloctane-3-yl group, n-undecyl group, 1-methyldecyl group, 1-ethylnonyl group, n-dodecyl group, isododecyl group, 2- (n-butyl) octyl group, 2,3,4,6,6-pentamethylheptan-3-yl group, n-tridecyl Group, isotridecyl group, n-tetradecyl group, isotetradecyl group, 2- (n-hexyl) octyl group, 1-methyltridecyl group, n-pentadecyl group, isopentadecyl 3,7,11-trimethyldodecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, isostearyl group, n-nonadecyl group, n-eicosadecyl group, 3,7,11,15-tetramethyl A hexadecyl group, a henicosyl group, a docosyl group, etc. are mentioned.
これらのうち、炭素数8〜22の分枝状のアルキル基が好ましく、特に、2−エチルヘキシル基、イソステアリル基、またはイソデシル基が好ましい。 Among these, a branched alkyl group having 8 to 22 carbon atoms is preferable, and a 2-ethylhexyl group, an isostearyl group, or an isodecyl group is particularly preferable.
前記一般式(1)中、nはエチレンオキサイドの付加モル数であり、0〜30の整数であるが、好ましくは0〜10の整数である。mは1〜3の整数であり、好ましくは1または2である。 In the general formula (1), n is the number of moles of ethylene oxide added and is an integer of 0 to 30, preferably an integer of 0 to 10. m is an integer of 1 to 3, preferably 1 or 2.
前記一般式(1)中、Mは水素原子、アルカリ金属、第2族金属、アンモニウム基、または有機アンモニウム基である。アルカリ金属としては、例えば、リチウム(Li)、ナトリウム(Na)、カリウム(K)等が挙げられ、第2族金属としては、例えば、ベリリウム(Be)、マグネシウム(Mg)、カルシウム(Ca)、ストロンチウム(Sr)、バリウム(Ba)等が挙げられる。有機アンモニウム基とは、有機アミン由来のアンモニウム基であり、前記有機アミンとしては、例えば、モノエタノールアミン、ジエタノールアミン、トリエタノールアミンなどのアルカノールアミン、メチルアミン、ジメチルアミン、トリエチルアミン、エチルアミン、ジエチルアミン、トリエチルアミン等が挙げられる。 In the general formula (1), M is a hydrogen atom, an alkali metal, a Group 2 metal, an ammonium group, or an organic ammonium group. Examples of the alkali metal include lithium (Li), sodium (Na), and potassium (K). Examples of the Group 2 metal include beryllium (Be), magnesium (Mg), calcium (Ca), Examples include strontium (Sr) and barium (Ba). The organic ammonium group is an ammonium group derived from an organic amine. Examples of the organic amine include alkanolamines such as monoethanolamine, diethanolamine, and triethanolamine, methylamine, dimethylamine, triethylamine, ethylamine, diethylamine, and triethylamine. Etc.
なお、上記リン酸エステル化合物は、単独でもまたは2種以上組み合わせて用いてもよい。また、上記リン酸エステル化合物は、市販品を用いてもよいし合成品を用いてもよい。 In addition, you may use the said phosphate ester compound individually or in combination of 2 or more types. Moreover, the said phosphate ester compound may use a commercial item, and may use a synthetic product.
上記リン酸エステル化合物の含有量は、ポリオレフィン樹脂(A)の量を100質量部として、1〜30質量部であることが好ましい。 The content of the phosphoric ester compound is preferably 1 to 30 parts by mass based on 100 parts by mass of the polyolefin resin (A).
本発明の水性分散体は、例えば、ガラス繊維等の無機繊維用集束剤、炭素繊維用集束剤、金属塗装、潤滑剤、トナーバインダー、ガラス繊維とオレフィン樹脂とのヒートシール剤、フロアーポリッシュなどに好適に用いられる。 The aqueous dispersion of the present invention can be used for, for example, a sizing agent for inorganic fibers such as glass fibers, a sizing agent for carbon fibers, a metal coating, a lubricant, a toner binder, a heat sealant of glass fibers and an olefin resin, and a floor polish. Preferably used.
以下、実施例を挙げて本発明をさらに詳細に説明するが、本発明は下記の実施例により何ら制限されるものではない。また、重量平均分子量の測定は下記表1に記載の条件により測定を行った。 EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated further in detail, this invention is not restrict | limited at all by the following Example. The weight average molecular weight was measured under the conditions described in Table 1 below.
また、粘度の測定にはB型粘度計(株式会社東京計器製造所製 形式:BM)を用い、25℃での粘度を測定した。 Moreover, the viscosity in 25 degreeC was measured for the measurement of a viscosity using the B-type viscometer (Tokyo Keiki Manufacturing Co., Ltd. model: BM).
<分散剤の製造>
(製造例1)
温度計、冷却器、攪拌機、および窒素導入管を備えた五つ口フラスコに、シクロヘキシルメタクリレート 100.5質量部、2−エチルヘキシルアクリレート 28.7質量部、メタクリル酸 71.7質量部、40質量%アクリルアミド水溶液 215.3質量部、ターピノーレン 1質量部、メルカプトプロピオン酸−2−エチルヘキシル 0.5質量部、およびエチレングリコールビスチオグリコレート 1.5質量部をそれぞれ仕込んだ。さらに、水 290.9質量部、イソプロピルアルコール 280質量部を仕込み、80℃まで加熱を行った。その後、重合開始剤としてアゾビスイソブチロニトリル 5.8質量部を加え、80℃で4時間重合反応を行った。反応終了後、イソプロピルアルコールを留去し、さらに水で濃度を調製することで、重量平均分子量が101,000である高分子分散剤1を濃度30質量%で含む水性分散液1(分散液の粘度:960mPa・s)を得た。
<Manufacture of dispersant>
(Production Example 1)
In a five-necked flask equipped with a thermometer, a condenser, a stirrer, and a nitrogen introduction tube, 100.5 parts by mass of cyclohexyl methacrylate, 28.7 parts by mass of 2-ethylhexyl acrylate, 71.7 parts by mass of methacrylic acid, 40% by mass Acrylamide aqueous solution 215.3 parts by mass, terpinolene 1 part by mass, mercaptopropionic acid-2-ethylhexyl 0.5 part by mass, and ethylene glycol bisthioglycolate 1.5 part by mass were charged. Furthermore, 290.9 parts by mass of water and 280 parts by mass of isopropyl alcohol were charged and heated to 80 ° C. Thereafter, 5.8 parts by mass of azobisisobutyronitrile was added as a polymerization initiator, and a polymerization reaction was performed at 80 ° C. for 4 hours. After completion of the reaction, isopropyl alcohol was distilled off, and the concentration was adjusted with water, whereby an aqueous dispersion 1 (dispersion of the dispersion) containing the polymer dispersant 1 having a weight average molecular weight of 101,000 at a concentration of 30% by mass. Viscosity: 960 mPa · s) was obtained.
(製造例2)
製造例1と同様の反応装置に、シクロヘキシルメタクリレート 57.2質量部、n−ブチルアクリレート 57.2質量部、メタクリル酸 85.8質量部、40質量%アクリルアミド水溶液 214.5質量部、ターピノーレン 2.9質量部、α−メチルスチレンダイマー 2.9質量部、およびトリメチロールプロパントリスチオグリコレート 2.6質量部をそれぞれ仕込んだ。さらに、水 291.3質量部、イソプロピルアルコール 280質量部を仕込み、80℃まで加熱を行った。その後、重合開始剤として過硫酸アンモニウム 5.7質量部を加え、80℃で4時間重合反応を行った。反応終了後、イソプロピルアルコールを留去し、さらに水で濃度を調製することで、重量平均分子量が101,000である高分子分散剤2を濃度30質量%で含む水性分散液2(分散液の粘度:860mPa・s)を得た。
(Production Example 2)
In the same reactor as in Production Example 1, 57.2 parts by mass of cyclohexyl methacrylate, 57.2 parts by mass of n-butyl acrylate, 85.8 parts by mass of methacrylic acid, 214.5 parts by mass of acrylamide aqueous solution 214.5 parts by mass, and terpinolene. 9 parts by mass, 2.9 parts by mass of α-methylstyrene dimer, and 2.6 parts by mass of trimethylolpropane tristhioglycolate were charged. Furthermore, 291.3 parts by mass of water and 280 parts by mass of isopropyl alcohol were charged and heated to 80 ° C. Thereafter, 5.7 parts by mass of ammonium persulfate was added as a polymerization initiator, and a polymerization reaction was performed at 80 ° C. for 4 hours. After completion of the reaction, isopropyl alcohol is distilled off, and the concentration is adjusted with water, whereby an aqueous dispersion 2 containing a polymer dispersant 2 having a weight average molecular weight of 101,000 at a concentration of 30% by mass (dispersion of the dispersion). Viscosity: 860 mPa · s) was obtained.
(製造例3)
製造例1と同様の反応装置に、シクロヘキシルメタクリレート 56.7質量部、n−ブチルメタクリレート 28.4質量部、2−エチルヘキシルアクリレート 28.4質量部、40質量%アクリルアミド水溶液 248質量部、イタコン酸 56.7質量部、p−スチレンスルホン酸ナトリウム 8.5質量部、ビニルスルホン酸ナトリウム 5.7質量部、ターピノーレン 2.8質量部、α−メチルスチレンダイマー 2.8質量部、2−メルカプトエタノール 2.8質量部、およびエチレングリコールビスチオグリコレート 1.2質量部をそれぞれ仕込んだ。さらに、水 271.2質量部、イソプロピルアルコール 280質量部を加え、80℃まで加熱を行った。その後、重合開始剤として過硫酸アンモニウム 5.7質量部を添加し、80℃で4時間反応を行った。反応終了後、イソプロピルアルコールを留去し、水で濃度調整を行うことにより、重量平均分子量が120,000である高分子分散剤3を濃度30質量%で含む水性分散液3(分散液の粘度:800mPa・s)を得た。
(Production Example 3)
In the same reactor as in Production Example 1, 56.7 parts by mass of cyclohexyl methacrylate, 28.4 parts by mass of n-butyl methacrylate, 28.4 parts by mass of 2-ethylhexyl acrylate, 248 parts by mass of an aqueous acrylamide solution 248 parts by mass, and itaconic acid 56 0.7 parts by mass, sodium p-styrenesulfonate 8.5 parts by mass, sodium vinylsulfonate 5.7 parts by mass, terpinolene 2.8 parts by mass, α-methylstyrene dimer 2.8 parts by mass, 2-mercaptoethanol 2 8 parts by mass and 1.2 parts by mass of ethylene glycol bisthioglycolate were charged. Furthermore, 271.2 parts by mass of water and 280 parts by mass of isopropyl alcohol were added and heated to 80 ° C. Thereafter, 5.7 parts by mass of ammonium persulfate was added as a polymerization initiator and reacted at 80 ° C. for 4 hours. After completion of the reaction, isopropyl alcohol was distilled off, and the concentration was adjusted with water, whereby an aqueous dispersion 3 (the viscosity of the dispersion) containing the polymer dispersant 3 having a weight average molecular weight of 120,000 at a concentration of 30% by mass. : 800 mPa · s).
(製造例4)
製造例1と同様の反応装置に、シクロヘキシルメタクリレートを34.2質量部、2−エチルヘキシルアクリレート 22.8質量部、40質量%アクリルアミド水溶液 320.3質量部、イタコン酸 71.2質量部、メタアリルスルホン酸ナトリウム 14.2部、ビニルスルホン酸ナトリウムを14.2部、ターピノーレン 0.6質量部、2−メルカプトエタノール 5.7質量部、エチレングリコールビスチオグリコレート 1.0質量部、水 227.9質量部、およびイソプロピルアルコール 280質量部を加え、さらに重合開始剤としてアゾイソブチロニトリルを5.7質量部添加し、40℃で溶解した。その後80℃に加熱し、重合反応を4時間行った。反応終了後、イソプロピルアルコールを留去し、水で濃度調整を行うことにより、重量平均分子量が140,000である高分子分散剤4を濃度30質量%で含む水性分散液4(分散液の粘度:700mPa・s)を得た。
(Production Example 4)
In the same reactor as in Production Example 1, 34.2 parts by mass of cyclohexyl methacrylate, 22.8 parts by mass of 2-ethylhexyl acrylate, 320.3 parts by mass of 40% by mass acrylamide aqueous solution, 71.2 parts by mass of itaconic acid, methallyl 14.2 parts of sodium sulfonate, 14.2 parts of sodium vinyl sulfonate, 0.6 parts by weight of terpinolene, 5.7 parts by weight of 2-mercaptoethanol, 1.0 part by weight of ethylene glycol bisthioglycolate, water 227. 9 parts by mass and 280 parts by mass of isopropyl alcohol were added, and 5.7 parts by mass of azoisobutyronitrile as a polymerization initiator was further added and dissolved at 40 ° C. Thereafter, the mixture was heated to 80 ° C., and the polymerization reaction was performed for 4 hours. After completion of the reaction, isopropyl alcohol was distilled off, and the concentration was adjusted with water, whereby an aqueous dispersion 4 containing a polymer dispersant 4 having a weight average molecular weight of 140,000 at a concentration of 30% by mass (viscosity of the dispersion). : 700 mPa · s).
(製造例5)
製造例1と同様の反応装置に、シクロヘキシルメタクリレート 76.1質量部、2−エチルヘキシルアクリレート 25.1質量部、40質量%アクリルアミド水溶液 379.02質量部、イタコン酸 190.05質量部、2−エチルヘキシル−3−メルカプトプロピオネート 12.3質量部、p−スチレンスルホン酸ナトリウム 30質量部、β−メルカプトプロピオン酸 10.7質量部、水 1109.0質量部、およびイソプロピルアルコール 291.0質量部を加え、さらに重合開始剤としてアゾイソブチロニトリル 4.8質量部を添加し40℃で溶解した。その後80℃まで加熱し、4時間重合反応を行った。反応終了後、イソプロピルアルコールの留去を行い、水で濃度調整を行うことにより、重量平均分子量が150,000である高分子分散剤5を濃度30質量%で含む水性分散液5(分散液の粘度:800mPa・s)を得た。
(Production Example 5)
In the same reaction apparatus as in Production Example 1, 76.1 parts by mass of cyclohexyl methacrylate, 25.1 parts by mass of 2-ethylhexyl acrylate, 379.02 parts by mass of 40% by mass acrylamide aqueous solution, 190.05 parts by mass of itaconic acid, 2-ethylhexyl -3-mercaptopropionate 12.3 parts by mass, p-sodium styrenesulfonate 30 parts by mass, β-mercaptopropionic acid 10.7 parts by mass, water 1109.0 parts by mass, and isopropyl alcohol 291.0 parts by mass In addition, 4.8 parts by mass of azoisobutyronitrile as a polymerization initiator was added and dissolved at 40 ° C. Thereafter, the mixture was heated to 80 ° C. and subjected to a polymerization reaction for 4 hours. After completion of the reaction, isopropyl alcohol was distilled off, and the concentration was adjusted with water, whereby aqueous dispersion 5 (dispersion of dispersion) containing polymer dispersant 5 having a weight average molecular weight of 150,000 at a concentration of 30% by mass was obtained. Viscosity: 800 mPa · s) was obtained.
(製造例6)
製造例1と同様の反応装置に、シクロヘキシルメタクリレート 76.1質量部、2−エチルヘキシルアクリレート 25.1質量部、イタコン酸 190.1質量部、40質量%アクリルアミド水溶液 189.5質量部、2−エチルヘキシル−3−メルカプトプロピオネート 12質量部、p−スチレンスルホン酸ナトリウム 30.0質量部、β−メルカプトプロピオン酸 7.2質量部、水 463.0質量部、およびイソプロピルアルコール 291質量部を加え、さらに重合開始剤としてアゾイソブチロニトリル 4.8質量部を添加し40℃で溶解した。その後80℃まで加熱し、4時間重合反応を行った。反応終了後、イソプロピルアルコールの留去を行い、水で濃度調整を行うことにより、重量平均分子量が160,000である高分子分散剤6を濃度30質量%で含む水性分散液6(分散液の粘度:800mPa・s)を得た。
(Production Example 6)
In the same reactor as in Production Example 1, 76.1 parts by mass of cyclohexyl methacrylate, 25.1 parts by mass of 2-ethylhexyl acrylate, 190.1 parts by mass of itaconic acid, 189.5 parts by mass of acrylamide aqueous solution 189.5 parts by mass, 2-ethylhexyl -12 parts by mass of -3-mercaptopropionate, 30.0 parts by mass of sodium p-styrenesulfonate, 7.2 parts by mass of β-mercaptopropionic acid, 463.0 parts by mass of water, and 291 parts by mass of isopropyl alcohol, Further, 4.8 parts by mass of azoisobutyronitrile was added as a polymerization initiator and dissolved at 40 ° C. Thereafter, the mixture was heated to 80 ° C. and subjected to a polymerization reaction for 4 hours. After completion of the reaction, isopropyl alcohol was distilled off, and the concentration was adjusted with water, whereby an aqueous dispersion 6 (dispersion liquid dispersion 6) containing a polymer dispersant 6 having a weight average molecular weight of 160,000 at a concentration of 30% by mass was obtained. Viscosity: 800 mPa · s) was obtained.
(製造例7)
製造例1と同様の反応装置に、イタコン酸 129.7質量部、40質量%アクリルアミド水溶液 252.7質量部、β−メルカプトプロピオン酸 7.1質量部、水 342.4質量部、およびイソプロピルアルコール110.0質量部を加え、さらに重合開始剤としてアゾイソブチロニトリル 3.2質量部を添加し、40℃で溶解した。その後80℃まで加熱を行い、4時間重合反応行った。反応終了後、イソプロピルアルコールの留去を行い、水で濃度調整を行うことにより、重量平均分子量が180,000である高分子分散剤7を濃度30質量%で含む水性分散液7(分散液の粘度:1000mPa・s)を得た。
(Production Example 7)
In the same reactor as in Production Example 1, itaconic acid 129.7 parts by mass, 40% by mass acrylamide aqueous solution 252.7 parts by mass, β-mercaptopropionic acid 7.1 parts by mass, water 342.4 parts by mass, and isopropyl alcohol 110.0 parts by mass was added, and 3.2 parts by mass of azoisobutyronitrile as a polymerization initiator was further added and dissolved at 40 ° C. Thereafter, the mixture was heated to 80 ° C. and subjected to a polymerization reaction for 4 hours. After completion of the reaction, isopropyl alcohol was distilled off, and the concentration was adjusted with water, whereby an aqueous dispersion 7 (dispersion of the dispersion) containing a polymer dispersant 7 having a weight average molecular weight of 180,000 at a concentration of 30% by mass. Viscosity: 1000 mPa · s) was obtained.
<水性分散体の製造>
(実施例1)
攪拌機、温度計、温度コントローラーを備えた内容量1.0Lの乳化設備を有するオートクレーブに、無水マレイン酸変性ポリプロピレン(EASTMAN CHEMICAL COMPANY製「EASTMAN G3216」、重量平均分子量:60,000、酸価:16)170g、製造例5で製造した水性分散液5(高分子分散剤5の濃度:30質量%)25.6g、ポリオキシエチレンアルキルエーテル(青木油脂工業株式会社製、セフティカットLI−3085)16.8g、ポリオキシエチレンアルキルエーテル(東邦化学工業株式会社製、ペグノールO−4)18.4g、ドデシルベンゼンスルホン酸ソーダ(テイカ株式会社製、テイカパワーBN2060、有効成分:60質量%)6.5g、無水重亜硫酸ソーダ 0.7g、ジメチルエタノールアミン(日本乳化剤株式会社製、アミノアルコール 2Mabs)13.5g、イオン交換水 291.9gを加え、165℃まで加熱し500rpmで1時間熟成した。その後、140℃まで冷却し内圧を下げた後、別途用意した165℃のイオン交換水 170.0gを加え再度165℃まで加熱し、500rpmで1時間熟成した。熟成後40℃まで冷却し、無水マレイン酸変性ポリプロピレンの濃度が30質量%である水性分散体1を得た。
<Production of aqueous dispersion>
Example 1
In an autoclave having an emulsification facility with an internal capacity of 1.0 L equipped with a stirrer, a thermometer, and a temperature controller, maleic anhydride-modified polypropylene (EASTMAN G3216 manufactured by EASTMAN CHEMICAL COMPANY, weight average molecular weight: 60,000, acid value: 16 ) 170 g, 25.6 g of the aqueous dispersion 5 produced in Production Example 5 (concentration of polymer dispersant 5: 30% by mass), polyoxyethylene alkyl ether (Aoki Yushi Kogyo Co., Ltd., Safety Cut LI-3085) 16 .8 g, polyoxyethylene alkyl ether (Toho Chemical Industries, Pegnol O-4) 18.4 g, dodecylbenzenesulfonic acid soda (Taika Co., Ltd., Teica Power BN2060, active ingredient: 60% by mass) 6.5 g , 0.7 g anhydrous sodium bisulfite 13.5 g of methylethanolamine (manufactured by Nippon Emulsifier Co., Ltd., amino alcohol 2 Mabs) and 291.9 g of ion-exchanged water were added, heated to 165 ° C. and aged at 500 rpm for 1 hour. Then, after cooling to 140 ° C. and lowering the internal pressure, 170.0 g of 165 ° C. ion exchange water prepared separately was added, and the mixture was heated again to 165 ° C. and aged at 500 rpm for 1 hour. After aging, the mixture was cooled to 40 ° C. to obtain an aqueous dispersion 1 having a maleic anhydride-modified polypropylene concentration of 30% by mass.
(実施例2)
攪拌機、温度計、温度コントローラーを備えた内容量1.0Lの乳化設備を有するオートクレーブに、無水マレイン酸変性ポリプロピレン(EASTMAN CHEMICAL COMPANY製「EASTMAN G3216」、重量平均分子量:60,000、酸価:16)170g、製造例5で製造した水性分散液5(高分子分散剤5の濃度:30質量%)25.6g、ポリオキシエチレンアルキルエーテル(青木油脂工業株式会社製、セフティカットLI−3085)15.2g、ポリオキシエチレンアルキルエーテル(東邦化学工業株式会社製 ペグノールO−4)16.6g、ドデシルベンゼンスルホン酸ソーダ(テイカ株式会社製、テイカパワーBN2060、有効成分:60質量%)6.1g、無水重亜硫酸ソーダ 0.7g、ジメチルエタノールアミン(日本乳化剤株式会社製、アミノアルコール 2Mabs)5.8g、イオン交換水 286.3gを加え、165℃まで加熱し500rpmで1時間熟成した。その後、140℃まで冷却し内圧を下げた後、別途用意した165℃のイオン交換水 320gを導入し再度165℃まで加熱し、500rpmで1時間熟成した。熟成後40℃まで冷却し、無水マレイン酸変性ポリプロピレンの濃度が25質量%である水性分散体2を得た。
(Example 2)
In an autoclave having an emulsification facility with an internal capacity of 1.0 L equipped with a stirrer, a thermometer, and a temperature controller, maleic anhydride-modified polypropylene (EASTMAN G3216 manufactured by EASTMAN CHEMICAL COMPANY, weight average molecular weight: 60,000, acid value: 16 ) 170 g, 25.6 g of the aqueous dispersion 5 produced in Production Example 5 (concentration of polymer dispersant 5: 30% by mass), 15 polyoxyethylene alkyl ether (Aoki Yushi Kogyo Co., Ltd., Safety Cut LI-3085) 15 .2 g, polyoxyethylene alkyl ether (Pegnol O-4 manufactured by Toho Chemical Industry Co., Ltd.) 16.6 g, sodium dodecylbenzenesulfonate (Taika Co., Ltd., Teica Power BN2060, active ingredient: 60 mass%) 6.1 g, Anhydrous sodium bisulfite 0.7g, dime Ethanolamine (Nippon Emulsifier Co., amino alcohols 2Mabs) 5.8g, and deionized water 286.3g was added and aged for 1 hour at 500rpm and heated to 165 ° C.. Then, after cooling to 140 ° C. and lowering the internal pressure, 320 g of ion-exchanged water of 165 ° C. prepared separately was introduced, heated again to 165 ° C., and aged at 500 rpm for 1 hour. After aging, the mixture was cooled to 40 ° C. to obtain an aqueous dispersion 2 having a maleic anhydride-modified polypropylene concentration of 25% by mass.
(実施例3)
攪拌機、温度計、温度コントローラーを備えた内容量1.0Lの乳化設備を有するオートクレーブに無水マレイン酸変性ポリプロピレン(EASTMAN CHEMICAL COMPANY製「EASTMAN G3216」、重量平均分子量:60,000、酸価:16)170g、製造例6で製造した水性分散液6(高分子分散剤6の濃度:30質量%)28.4g、ポリオキシエチレンアルキルエーテル(青木油脂工業株式会社製、セフティカットLI−3085)16.8g、ポリオキシエチレンアルキルエーテル(東邦化学工業株式会社製 ペグノールO−4)18.4g、ドデシルベンゼンスルホン酸ソーダ(テイカ株式会社製、テイカパワーBN2060、有効成分:60質量%)6.5g、無水重亜硫酸ソーダ 0.7g、ジメチルエタノールアミン(日本乳化剤株式会社製、アミノアルコール 2Mabs)13.5g、およびイオン交換水 267.6g 165℃まで加熱し500rpmで1時間熟成した。その後、140℃まで冷却し内圧を下げた後、別途用意した165℃のイオン交換水 170.0gを導入し再度165℃まで加熱し、500rpmで1時間熟成した。熟成後40℃まで冷却し、無水マレイン酸変性ポリプロピレンの濃度が30質量%である水性分散体3を得た。
(Example 3)
Maleic anhydride-modified polypropylene ("EASTMAN G3216" manufactured by EASTMAN CHEMICAL COMPANY, weight average molecular weight: 60,000, acid value: 16) in an autoclave having an emulsification facility with an internal volume of 1.0 L equipped with a stirrer, thermometer and temperature controller 170 g, 28.4 g of the aqueous dispersion 6 produced in Production Example 6 (concentration of polymer dispersant 6: 30% by mass), polyoxyethylene alkyl ether (Aoki Yushi Kogyo Co., Ltd., Safety Cut LI-3085) 16. 8 g, 18.4 g of polyoxyethylene alkyl ether (Pegnol O-4 manufactured by Toho Chemical Industry Co., Ltd.), 6.5 g of sodium dodecylbenzenesulfonate (Taika Power BN2060, active ingredient: 60% by mass), anhydrous Sodium bisulfite 0.7g, Jime Ethanolamine (Nippon Emulsifier Co., amino alcohols 2Mabs) 13.5g, and heated to ion-exchange water 267.6g 165 ℃ was aged for 1 hour at 500 rpm. Then, after cooling to 140 ° C. and lowering the internal pressure, 170.0 g of 165 ° C. ion exchange water prepared separately was introduced, heated again to 165 ° C., and aged at 500 rpm for 1 hour. After aging, the mixture was cooled to 40 ° C. to obtain an aqueous dispersion 3 having a maleic anhydride-modified polypropylene concentration of 30% by mass.
(実施例4)
攪拌機、温度計、温度コントローラーを備えた内容量1.0Lの乳化設備を有するオートクレーブに、無水マレイン酸変性ポリプロピレン(EASTMAN CHEMICAL COMPANY製「EASTMAN G3216」、重量平均分子量:60,000、酸価:16)170g、製造例7で製造した水性分散液7(高分子分散剤7の濃度:30質量%)28.4g、ポリオキシエチレンアルキルエーテル(青木油脂工業株式会社製、セフティカットLI−3085)16.8g、ポリオキシエチレンアルキルエーテル(青木油脂工業株式会社製、ブラウノンEN−1502)18.4g、ドデシルベンゼンスルホン酸ソーダ(テイカ株式会社製、テイカパワーBN2060、有効成分:60質量%)6.5g、無水重亜硫酸ソーダ 0.7g、ジメチルエタノールアミン(日本乳化剤株式会社製、アミノアルコール 2Mabs)13.5g、およびイオン交換水 267.6gを加え、165℃まで加熱し500rpmで1時間熟成した。その後、140℃まで冷却し内圧を下げた後、別途用意した165℃のイオン交換水 170.0gを添加し再度165℃まで加熱し、500rpmで1時間熟成した。熟成後40℃まで冷却し、無水マレイン酸変性ポリプロピレンの濃度が30質量%である水性分散体4を得た。
Example 4
In an autoclave having an emulsification facility with an internal capacity of 1.0 L equipped with a stirrer, a thermometer, and a temperature controller, maleic anhydride-modified polypropylene (EASTMAN G3216 manufactured by EASTMAN CHEMICAL COMPANY, weight average molecular weight: 60,000, acid value: 16 ) 170 g, 28.4 g of the aqueous dispersion 7 produced in Production Example 7 (concentration of polymer dispersant 7: 30 mass%), polyoxyethylene alkyl ether (Aoki Oil & Fat Co., Ltd., Safety Cut LI-3085) 16 .8 g, polyoxyethylene alkyl ether (Aoki Yushi Kogyo Co., Ltd., Brownon EN-1502) 18.4 g, dodecylbenzene sulfonic acid soda (Taika Co., Ltd., Teica Power BN2060, active ingredient: 60 mass%) 6.5 g Anhydrous sodium bisulfite 0. g, dimethylethanolamine (Nippon Emulsifier Co., amino alcohols 2Mabs) 13.5g, and deionized water 267.6g was added and aged for 1 hour at 500rpm and heated to 165 ° C.. Then, after cooling to 140 ° C. and lowering the internal pressure, 170.0 g of 165 ° C. ion-exchanged water prepared separately was added and heated again to 165 ° C., followed by aging at 500 rpm for 1 hour. After aging, the mixture was cooled to 40 ° C. to obtain an aqueous dispersion 4 having a maleic anhydride-modified polypropylene concentration of 30% by mass.
(比較例1)
攪拌機、温度計、温度コントローラーを備えた内容量1.0Lの乳化設備を有するオートクレーブに、無水マレイン酸変性ポリプロピレン(EASTMAN CHEMICAL COMPANY製「EASTMAN G3216」、重量平均分子量:60,000、酸価:16)170g、ポリオキシエチレンアルキルエーテル(青木油脂工業株式会社製、セフティカットLI−3085)18.9g、ポリオキシエチレンアルキルエーテル(東邦化学工業株式会社製、ペグノールO−4)20.6g、ドデシルベンゼンスルホン酸ソーダ(テイカ株式会社製、テイカパワーBN2060、有効成分:60質量%)6.1g、無水重亜硫酸ソーダ 0.7g、ジメチルエタノールアミン(日本乳化剤株式会社製、アミノアルコール 2Mabs)5.8g、イオン交換水 290.0gを加え、165℃まで加熱し500rpmで1時間熟成した。その後、140℃まで冷却し内圧を下げた後、別途用意した165℃のイオン交換水 320gを加え、再度165℃まで加熱し、500rpmで1時間熟成した。熟成後40℃まで冷却したが、未乳化物が多量に発生した。
(Comparative Example 1)
In an autoclave having an emulsification facility with an internal capacity of 1.0 L equipped with a stirrer, a thermometer, and a temperature controller, maleic anhydride-modified polypropylene (EASTMAN G3216 manufactured by EASTMAN CHEMICAL COMPANY, weight average molecular weight: 60,000, acid value: 16 ) 170 g, polyoxyethylene alkyl ether (Aoki Yushi Kogyo Co., Ltd., Safety Cut LI-3085) 18.9 g, polyoxyethylene alkyl ether (Toho Chemical Co., Ltd., Pegnol O-4) 20.6 g, dodecylbenzene Sulphonic acid soda (Taika Co., Ltd., Teica Power BN2060, active ingredient: 60% by mass) 6.1 g, anhydrous sodium bisulfite 0.7 g, dimethylethanolamine (Nippon Emulsifier Co., Ltd., amino alcohol 2 Mabs) 5 8 g, was added ion-exchanged water 290.0 g, and aged for 1 hour at 500rpm and heated to 165 ° C.. Then, after cooling to 140 ° C. and lowering the internal pressure, 320 g of ion-exchanged water of 165 ° C. prepared separately was added, heated again to 165 ° C., and aged at 500 rpm for 1 hour. Although it was cooled to 40 ° C. after aging, a large amount of non-emulsified product was generated.
(比較例2)
攪拌機、温度計、温度コントローラーを備えた内容量1.0Lの乳化設備を有するオートクレーブに、無水マレイン酸変性ポリプロピレン(EASTMAN CHEMICAL COMPANY製「EASTMAN G3216」、重量平均分子量:60,000、酸価:16)170g、高分子分散剤(サートマー社製、スチレン−マレイン酸共重合体、SMA−1000)8.5g、ポリオキシエチレンアルキルエーテル(青木油脂工業株式会社製、セフティカットLI−3085)16.8g、ポリオキシエチレンアルキルエーテル(東邦化学工業株式会社製、ペグノールO−4)18.4g、ドデシルベンゼンスルホン酸ソーダ(テイカ株式会社製、テイカパワーBN2060、有効成分:60質量%)6.5g、無水重亜硫酸ソーダ 0.7g、ジメチルエタノールアミン(日本乳化剤株式会社製、アミノアルコール 2Mabs)13.5g、イオン交換水 311.8gを加え、165℃まで加熱し1時間熟成した。その後、140℃まで冷却し内圧を下げた後、別途用意した165℃のイオン交換水 170.0gを導入し再度165℃まで加熱し、1時間熟成した。熟成後40℃まで冷却したが、未乳化物が多量に発生した。
(Comparative Example 2)
In an autoclave having an emulsification facility with an internal capacity of 1.0 L equipped with a stirrer, a thermometer, and a temperature controller, maleic anhydride-modified polypropylene (EASTMAN G3216 manufactured by EASTMAN CHEMICAL COMPANY, weight average molecular weight: 60,000, acid value: 16 ) 170 g, polymer dispersant (Sartomer, styrene-maleic acid copolymer, SMA-1000) 8.5 g, polyoxyethylene alkyl ether (Aoki Yushi Kogyo Co., Ltd., Safety Cut LI-3085) 16.8 g , 18.4 g of polyoxyethylene alkyl ether (manufactured by Toho Chemical Industry Co., Ltd., Pegnol O-4), 6.5 g of sodium dodecylbenzenesulfonate (manufactured by Teika Co., Ltd., Teica Power BN2060, active ingredient: 60% by mass), anhydrous Sodium bisulfite 0 0.7 g, 13.5 g of dimethylethanolamine (manufactured by Nippon Emulsifier Co., Ltd., amino alcohol 2 Mabs) and 311.8 g of ion-exchanged water were added, heated to 165 ° C. and aged for 1 hour. Then, after cooling to 140 ° C. and lowering the internal pressure, 170.0 g of 165 ° C. ion exchange water prepared separately was introduced, heated again to 165 ° C., and aged for 1 hour. Although it was cooled to 40 ° C. after aging, a large amount of non-emulsified product was generated.
(比較例3)
攪拌機、温度計、温度コントローラーを備えた内容量1.0Lの乳化設備を有するオートクレーブに、無水マレイン酸変性ポリプロピレン(EASTMAN CHEMICAL COMPANY製「EASTMAN G3216」、重量平均分子量:60,000、酸価:16)170g、高分子分散剤(サートマー社製、スチレン−マレイン酸共重合体、SMA−3000)8.5g、ポリオキシエチレンアルキルエーテル(青木油脂工業株式会社製、セフティカットLI−3085)16.8g、ポリオキシエチレンアルキルエーテル(東邦化学工業株式会社製、ペグノールO−4)18.4g、ドデシルベンゼンスルホン酸ソーダ(テイカ株式会社製、テイカパワーBN2060、有効成分:60質量%)6.5g、無水重亜硫酸ソーダ 0.7g、ジメチルエタノールアミン(日本乳化剤株式会社製、アミノアルコール 2Mabs)13.5g、イオン交換水 311.8gを加え、165℃まで加熱し1時間熟成した。その後、140℃まで冷却し内圧を下げた後、別途用意した165℃のイオン交換水 170.0gを加え165℃まで加熱し、1時間熟成した。熟成後40℃まで冷却したが、未乳化物が多量に発生した。
(Comparative Example 3)
In an autoclave having an emulsification facility with an internal capacity of 1.0 L equipped with a stirrer, a thermometer, and a temperature controller, maleic anhydride-modified polypropylene (EASTMAN G3216 manufactured by EASTMAN CHEMICAL COMPANY, weight average molecular weight: 60,000, acid value: 16 ) 170 g, polymer dispersant (Sartomer, styrene-maleic acid copolymer, SMA-3000) 8.5 g, polyoxyethylene alkyl ether (Aoki Yushi Kogyo Co., Ltd., Safety Cut LI-3085) 16.8 g , 18.4 g of polyoxyethylene alkyl ether (manufactured by Toho Chemical Industry Co., Ltd., Pegnol O-4), 6.5 g of sodium dodecylbenzenesulfonate (manufactured by Teika Co., Ltd., Teica Power BN2060, active ingredient: 60% by mass), anhydrous Sodium bisulfite 0 0.7 g, 13.5 g of dimethylethanolamine (manufactured by Nippon Emulsifier Co., Ltd., amino alcohol 2 Mabs) and 311.8 g of ion-exchanged water were added, heated to 165 ° C. and aged for 1 hour. Then, after cooling to 140 ° C. and lowering the internal pressure, 170.0 g of 165 ° C. ion exchange water prepared separately was added and heated to 165 ° C. and aged for 1 hour. Although it was cooled to 40 ° C. after aging, a large amount of non-emulsified product was generated.
<評価>
1.揮発残分
JIS K−6833(1980年)に準じて測定した。
<Evaluation>
1. Volatile residue Measured according to JIS K-6833 (1980).
2.pH
JIS K−6833(1980年)に準じて測定した。
2. pH
It measured according to JIS K-6833 (1980).
3.粘度
JIS Z−8803(1959年)に準じて測定した。
3. Viscosity Viscosity was measured according to JIS Z-8803 (1959).
4.平均粒径
Particle sizing systems社製、NICOMP 380にて、散乱光の光強度分布より、樹脂粒子の平均粒径を測定した。
4). Average Particle Size The average particle size of the resin particles was measured from the light intensity distribution of the scattered light using NICOMP 380 manufactured by Particle Sizing Systems.
5.液安定性
水性分散体製造後、常温(25℃)で1ヶ月保存した後の状態を、目視にて観察した。
5. Liquid stability After the aqueous dispersion was produced, the state after storage for 1 month at room temperature (25 ° C.) was visually observed.
実施例1〜4で得られた水性分散体の性状および各種評価結果を表2に示す。 Table 2 shows the properties and various evaluation results of the aqueous dispersions obtained in Examples 1 to 4.
表2から明らかなように、本発明の水性分散体においては、重量平均分子量が2万以上であるポリオレフィン樹脂が良好に分散していた。一方、上記のように、比較例1〜3の水性分散体では、未乳化物が多量に発生した。 As is clear from Table 2, in the aqueous dispersion of the present invention, the polyolefin resin having a weight average molecular weight of 20,000 or more was well dispersed. On the other hand, as described above, in the aqueous dispersions of Comparative Examples 1 to 3, a large amount of non-emulsified matter was generated.
Claims (4)
不飽和カルボン酸(b−1) 3.5〜90質量部および(メタ)アクリルアミド単量体(b−2) 10〜96.5質量部(ただし、(b−1)と(b−2)との合計は100質量部)を含む単量体成分を共重合して得られる高分子分散剤(B)と、
を含む、水性分散体。 A polyolefin resin (A) having a weight average molecular weight of 20,000 or more;
Unsaturated carboxylic acid (b-1) 3.5-90 mass parts and (meth) acrylamide monomer (b-2) 10-96.5 mass parts (however, (b-1) and (b-2) And a polymer dispersant (B) obtained by copolymerizing monomer components containing 100 parts by mass),
An aqueous dispersion comprising
前記高分子分散剤(B)の含有量がポリオレフィン樹脂(A)の量を100質量部として、1〜35質量部である、請求項1または2に記載の水性分散体。 The content of the polyolefin resin (A) is 10 to 40% by mass with respect to the total mass of the aqueous dispersion,
The aqueous dispersion according to claim 1 or 2, wherein the content of the polymer dispersing agent (B) is 1 to 35 parts by mass with respect to 100 parts by mass of the polyolefin resin (A).
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CN114761483A (en) * | 2019-12-05 | 2022-07-15 | 三井化学株式会社 | Aqueous dispersion and laminate |
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