JP2018035351A - メタクリル酸またはその無水物の小粒径テロマー - Google Patents
メタクリル酸またはその無水物の小粒径テロマー Download PDFInfo
- Publication number
- JP2018035351A JP2018035351A JP2017162285A JP2017162285A JP2018035351A JP 2018035351 A JP2018035351 A JP 2018035351A JP 2017162285 A JP2017162285 A JP 2017162285A JP 2017162285 A JP2017162285 A JP 2017162285A JP 2018035351 A JP2018035351 A JP 2018035351A
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- JP
- Japan
- Prior art keywords
- cotelomer
- particle size
- methacrylic acid
- telomer
- weight
- 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
Links
- 239000002245 particle Substances 0.000 title claims abstract description 40
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 43
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 title claims description 18
- 229920000642 polymer Polymers 0.000 claims abstract description 61
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 26
- 229920000570 polyether Polymers 0.000 claims abstract description 26
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 22
- 150000001412 amines Chemical class 0.000 claims abstract description 20
- 229920005862 polyol Polymers 0.000 claims abstract description 16
- 238000001035 drying Methods 0.000 claims abstract description 15
- 150000003077 polyols Chemical class 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 11
- 229920001577 copolymer Polymers 0.000 claims abstract description 6
- -1 alkyl mercaptans Chemical class 0.000 claims description 26
- 239000003999 initiator Substances 0.000 claims description 11
- 238000000227 grinding Methods 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000001694 spray drying Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000001125 extrusion Methods 0.000 claims description 4
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 4
- 238000012644 addition polymerization Methods 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims 1
- 238000002036 drum drying Methods 0.000 claims 1
- 238000013467 fragmentation Methods 0.000 claims 1
- 238000006062 fragmentation reaction Methods 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- 150000003871 sulfonates Chemical class 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 18
- 239000007787 solid Substances 0.000 abstract description 11
- 239000002243 precursor Substances 0.000 abstract description 9
- 239000000243 solution Substances 0.000 abstract description 4
- 239000003381 stabilizer Substances 0.000 abstract description 4
- 229920005646 polycarboxylate Polymers 0.000 abstract description 3
- 239000006254 rheological additive Substances 0.000 abstract description 3
- 125000005395 methacrylic acid group Chemical class 0.000 abstract description 2
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- 150000008064 anhydrides Chemical class 0.000 description 17
- 229920001427 mPEG Polymers 0.000 description 13
- 238000001542 size-exclusion chromatography Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920001223 polyethylene glycol Polymers 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000032050 esterification Effects 0.000 description 10
- 238000005886 esterification reaction Methods 0.000 description 10
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 239000002202 Polyethylene glycol Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000002033 PVDF binder Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000005102 attenuated total reflection Methods 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229920002732 Polyanhydride Polymers 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000004570 mortar (masonry) Substances 0.000 description 3
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000008030 superplasticizer Substances 0.000 description 3
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 239000012491 analyte Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000012711 chain transfer polymerization Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000013480 data collection Methods 0.000 description 2
- 229940031098 ethanolamine Drugs 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
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- 239000000543 intermediate Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000003921 particle size analysis Methods 0.000 description 2
- 238000010951 particle size reduction Methods 0.000 description 2
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- 238000001228 spectrum Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- FWMFMCKIDWLKIH-UHFFFAOYSA-N C(C(=C)C)(=O)O.[PH2](=O)O Chemical compound C(C(=C)C)(=O)O.[PH2](=O)O FWMFMCKIDWLKIH-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 235000003332 Ilex aquifolium Nutrition 0.000 description 1
- 235000002296 Ilex sandwicensis Nutrition 0.000 description 1
- 235000002294 Ilex volkensiana Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 241000220010 Rhode Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
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- 230000002950 deficient Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
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- 229950000688 phenothiazine Drugs 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
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- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- ACUGTEHQOFWBES-UHFFFAOYSA-M sodium hypophosphite monohydrate Chemical compound O.[Na+].[O-]P=O ACUGTEHQOFWBES-UHFFFAOYSA-M 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
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
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- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
MAAの次亜リン酸テロマーは、モノマーの総重量に基づいて、9.0重量%の次亜リン酸ナトリウム水和物を含む次亜リン酸ナトリウムの存在下で、水溶液中で重合させたメタクリル酸から形成した。
材料をエステル化させて櫛型ポリマーを作った。まず、重量平均分子量が約6000であるメタクリル酸の次亜リン酸テロマーを、150℃で2時間加熱し、水分を蒸発させ、実施例1として使用した。それから、オーブン乾燥させた次亜リン酸塩含有ポリメタクリル酸(pMAA)の一部を、200℃で30分加熱し、酸をポリメタクリル酸無水物(pMAAn)に変換し、これを実施例2とした。また、過硫酸塩で開始させた、Mwが6,500であるpMAAを実施例3で用いた。3つの材料はすべて、乳鉢と乳棒を用いてすりつぶした後、さらにRetsch(ペンシルバニア州ニュータウン)MM400ボールミルを用いて30Hzで2分間粉砕した。粒径分析は、Beckman−Coulter(カリフォルニア州ブレア)のLS 13 320レーザー回折式粒径分析器(Beckman−Coulter、カリフォルニア州ブレア)を用いて、乾燥材料で行った。その結果生じた平均粒径サイズを以下の表1に示す。
実施例7および7Aのポリマー、それぞれ、pMAA次亜リン酸テロマーおよび過硫酸テロマーは、150℃で2時間加熱し、水分を蒸発させた。それから、乳棒と乳鉢を用いて、いずれも手で粉末化した。乾燥材料の粒径は、Beckman−Coulter LS 13 320レーザー回折式粒径分析器(Beckman−Coulter、カリフォルニア州ブレア)で評価および測定した。その結果を下の表4に示す。
下の表5に示すように、高流動化剤反応物の配合は、ポリエーテル側鎖を形成する反応物ならびに実施例7および7Aの乾燥ポリマーから成り、Mw2,000のポリ(エチレングリコール)メチルエーテル(mPEG2K)(Aldrich Chemicals、ミズーリ州セントルイス)およびmPEG 5,000ポリ(エチレングリコール)メチルエーテルPolygylkol(登録商標)M 5,000S(Clariant Corp.、ノースカロライナ州マウント・ホリー・ウェスト);p−トルエンスルホン酸一水和物(p−TSA、純度>98.5%、固体)および水酸化リチウム(純度>98%、固体)(Aldrich);Irganox(登録商標)5057安定剤(BASF、イリノイ州ヴァンダリア)を含んでいた。
材料をエステル化させて櫛型ポリマーを作った。まず、スルホン酸塩基(重亜硫酸塩より)および硫酸塩基(過硫酸塩より)を有するメタクリル酸のテロマーを150℃で2時間加熱し、水分を蒸発させた。これらのポリメタクリル酸(pMAA)テロマーを、実施例12および14として使用した。それから、オーブン乾燥させた実施例12および14のpMAAテロマーの一部を、220℃で30分加熱し、酸を無水物(pMAAn)テロマーに変換した(それぞれ11および13)。4つの材料はすべて、乳鉢と乳棒を用いてすりつぶした後、さらにRetsch(ペンシルバニア州ニュータウン)MM400ボールミルを用いて30Hzで2分間粉砕した。粒径分析は、Beckman−Coulter(カリフォルニア州ブレア)のLS 13 320レーザー回折式粒径分析器(Beckman−Coulter、カリフォルニア州ブレア)を用いて、乾燥材料で行った。結果として得られた平均粒径を下の表7に示す。
Claims (11)
- ヘテロ原子を含み、さらに、平均粒径が2μm〜1mmである、メタクリル酸無水物の1つまたは複数のコテロマーの粒子または凝集体を含み、前記コテロマーの重量平均分子量(Mw)が、500〜100,000である組成物。
- 前記粒子または凝集体の平均粒径が5μmから最大700μmである、請求項1に記載の組成物。
- 前記コテロマーが、メタクリル酸無水物のコテロマーである、請求項1または2に記載の組成物。
- 前記コテロマーの重量平均分子量(Mw)が、2,500〜10,000である、請求項1〜3のいずれか一項に記載の組成物。
- 前記コテロマーが、前記コテロマーを作るために使われる反応物の総重量に基づいて、20〜98重量%のメタクリル酸またはその塩基を有する重合単位から誘導される重合残基を含み、前記重合残基がメタクリル酸無水物単位ならびにメタクリル酸および/またはメタクリル酸塩単位である、請求項1〜4のいずれか一項に記載の組成物。
- 前記コテロマーが、前記コテロマーにおける酸性重合単位の総重量に基づいて、少なくとも10重量%および最大70重量%のメタクリル酸無水物基を有する、請求項1〜5のいずれか一項に記載の組成物。
- 前記コテロマーが、前記コテロマーを作るために使われる反応物の総重量に基づいて、2〜20重量%のヘテロ原子含有化合物から誘導される残基を含む、請求項1〜6のいずれか一項に記載の組成物。
- メタクリル酸無水物基含有コテロマーの製造方法であって:
アルキルメルカプタン、酸化アルキルメルカプタン、亜硫酸塩、スルホン酸塩、亜リン酸塩、次亜リン酸塩、RAFT(可逆的付加開裂連鎖移動)触媒、アゾ開始剤およびその組合せから選択されるヘテロ原子含有化合物の存在下で、メタクリル酸およびその塩から選択される1つまたは複数のモノマー混合物を水溶液付加重合する工程、その結果生じるコポリマーを180〜230℃の温度で乾燥させる工程、ならびにその粒径を小さくして、コテロマー粒子または凝集体を作る工程を含む方法。 - 前記乾燥させる工程が、噴霧乾燥、流動層乾燥、溶融押出成形、および噴霧乾燥に続く押出成形またはドラム乾燥を含む、請求項8に記載の方法。
- 前記粒径を小さくする工程が、粉砕、挽砕、摩砕、微粉砕、破砕または凍結粉砕を含む、請求項8または9に記載の方法。
- 前記方法が、さらに:
前記コテロマー粒子または凝集体を、ポリエーテルポリオール、アルキルポリエーテルポリオール、ポリ(オキシアルキレン)モノアルキルエーテル、ポリエーテルアミン、またはアルキルポリエーテルアミンの1つまたは複数と、加熱して反応させ、櫛型ポリマーを形成する工程を含む、請求項8〜10のいずれか一項に記載の方法。
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KR20140088876A (ko) | 2014-07-11 |
EP2748213A1 (en) | 2014-07-02 |
KR20140088877A (ko) | 2014-07-11 |
EP2748212A1 (en) | 2014-07-02 |
BR112014010918B1 (pt) | 2020-12-15 |
JP2014533318A (ja) | 2014-12-11 |
BR112014010918A2 (pt) | 2017-05-16 |
CN103930453B (zh) | 2016-12-21 |
US20130123436A1 (en) | 2013-05-16 |
MX2014005587A (es) | 2014-07-30 |
CN103930454A (zh) | 2014-07-16 |
JP2014533319A (ja) | 2014-12-11 |
KR101942777B1 (ko) | 2019-01-28 |
US9365657B2 (en) | 2016-06-14 |
WO2013070644A1 (en) | 2013-05-16 |
US20130122299A1 (en) | 2013-05-16 |
BR112014010920A2 (pt) | 2017-05-16 |
KR101942775B1 (ko) | 2019-01-28 |
WO2013070652A1 (en) | 2013-05-16 |
MX347061B (es) | 2017-04-10 |
EP2748212B1 (en) | 2019-09-25 |
US9499642B2 (en) | 2016-11-22 |
JP6480992B2 (ja) | 2019-03-13 |
MX2014005586A (es) | 2014-07-30 |
JP6199874B2 (ja) | 2017-09-20 |
MX347794B (es) | 2017-05-10 |
EP2748213B1 (en) | 2019-09-25 |
CN103930453A (zh) | 2014-07-16 |
CN103930454B (zh) | 2017-05-24 |
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