TW574061B - Dispersants - Google Patents
Dispersants Download PDFInfo
- Publication number
- TW574061B TW574061B TW91105671A TW91105671A TW574061B TW 574061 B TW574061 B TW 574061B TW 91105671 A TW91105671 A TW 91105671A TW 91105671 A TW91105671 A TW 91105671A TW 574061 B TW574061 B TW 574061B
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- TW
- Taiwan
- Prior art keywords
- dispersant
- patent application
- scope
- item
- group
- Prior art date
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 95
- -1 phosphate ester Chemical class 0.000 claims abstract description 34
- 229920000768 polyamine Polymers 0.000 claims abstract description 22
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 21
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000002596 lactones Chemical class 0.000 claims abstract description 15
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 239000010452 phosphate Substances 0.000 claims abstract description 10
- 229920000728 polyester Polymers 0.000 claims abstract description 8
- JRFXQKZEGILCCO-UHFFFAOYSA-N 5,5-dimethyl-1,3-dioxan-2-one Chemical compound CC1(C)COC(=O)OC1 JRFXQKZEGILCCO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 45
- 239000007787 solid Substances 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 27
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000003973 paint Substances 0.000 claims description 11
- 239000000049 pigment Substances 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 239000004033 plastic Substances 0.000 claims description 8
- 229920003023 plastic Polymers 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 7
- 239000004642 Polyimide Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 229920001721 polyimide Polymers 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 4
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- ALFVSYUDZOYICO-UHFFFAOYSA-N carbonic acid ethene Chemical compound C=C.C=C.C=C.OC(O)=O ALFVSYUDZOYICO-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 abstract description 14
- 239000003795 chemical substances by application Substances 0.000 abstract description 13
- 229920000137 polyphosphoric acid Polymers 0.000 abstract description 8
- 229920002873 Polyethylenimine Polymers 0.000 abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000007788 liquid Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 13
- 238000005886 esterification reaction Methods 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000976 ink Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 230000000865 phosphorylative effect Effects 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 235000021317 phosphate Nutrition 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 241000640882 Condea Species 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000000227 grinding Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical group O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000052 vinegar Substances 0.000 description 4
- 235000021419 vinegar Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 101100505161 Caenorhabditis elegans mel-32 gene Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 229920002125 Sokalan® Chemical class 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- HSVPRYWNEODRGU-UHFFFAOYSA-J butanoate;zirconium(4+) Chemical compound [Zr+4].CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O HSVPRYWNEODRGU-UHFFFAOYSA-J 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 2
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 2
- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 description 2
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910000906 Bronze Inorganic materials 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-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
- 239000005639 Lauric acid Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 101100510439 Oryza sativa subsp. japonica KSL8 gene Proteins 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000010974 bronze Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 229910010293 ceramic material Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000001034 iron oxide pigment Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000696 magnetic material Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 2
- CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920000083 poly(allylamine) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
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- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- SRMHHEPXZLWKOK-UHFFFAOYSA-N heptan-3-amine Chemical compound CCCCC(N)CC SRMHHEPXZLWKOK-UHFFFAOYSA-N 0.000 description 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 description 1
- 229950004531 hexyldecanoic acid Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- LMHJFKYQYDSOQO-UHFFFAOYSA-N hydroxydecanoic acid Natural products CCCCCC(O)CCCC(O)=O LMHJFKYQYDSOQO-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical class COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- KELHQGOVULCJSG-UHFFFAOYSA-N n,n-dimethyl-1-(5-methylfuran-2-yl)ethane-1,2-diamine Chemical compound CN(C)C(CN)C1=CC=C(C)O1 KELHQGOVULCJSG-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AJCDFVKYMIUXCR-UHFFFAOYSA-N oxobarium;oxo(oxoferriooxy)iron Chemical compound [Ba]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O AJCDFVKYMIUXCR-UHFFFAOYSA-N 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Chemical class 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Chemical class 0.000 description 1
- 239000004814 polyurethane Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229950006800 prenderol Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FIABMSNMLZUWQH-UHFFFAOYSA-N propyl 2-methoxyacetate Chemical compound CCCOC(=O)COC FIABMSNMLZUWQH-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
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 239000012763 reinforcing filler Substances 0.000 description 1
- 239000008678 sanqi Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- FPSFKBGHBCHTOE-UHFFFAOYSA-N sodium 3-hydroxy-4-[(3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl)diazenyl]naphthalene-1-sulfonic acid Chemical compound [Na+].O=C1C(N=NC=2C3=CC=CC=C3C(=CC=2O)S(O)(=O)=O)C(C)=NN1C1=CC=CC=C1 FPSFKBGHBCHTOE-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229940094938 stannous 2-ethylhexanoate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/002—Pigment pastes, e.g. for mixing in paints in organic medium
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polyesters Or Polycarbonates (AREA)
- Lubricants (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Paper (AREA)
Description
574061 A7 B7
五、發明説明( 本發明係關於含環狀伸烷基碳酸酯之殘基 劑’含此種具有微㈣固體與液體介質之分散劑= =係,,及此種分散液與磨基劑在油漆二: 、“其包括用於非撞擊式列表機(例如,"即需即 列表機)之油墨),塑膠材質之用途。 已不斷設法尋❹不良貯存條件下仍具有較高流動性女 分散劑’因為此種分散劑具容易處理之優點。而且,才: 法尋找可以使大量微粒狀固體(例如,色素)分散在有機$ 體介質内並形成具優異性質(例如,改良光澤性)之油漆及 油墨之分散劑。 歐洲專利EP 164, 8Π揭示一種聚酯之磷酸酯分散劑,其 係經由聚合羥基羧酸(例如,6 _羥基己酸)或ε _己内酯而製 成。 WO 98/19784揭示含聚環氧烷類羰基鏈(下文稱為p〇AC 鏈)(其係衍生自視需要經烷基取代之ε _己内酯及5 —戊内 醋)之分散劑。該POAC鏈可含有能夠與聚胺(例如,聚乙 二亞胺)反應以得到鹼性分散劑之末端羧酸基,或該p〇AC 可含有能夠酯化以得到酸性分散劑之末端羥基。目前頃發 現可後得其它有用分散劑,其中該p〇AC鏈係衍生自一或 多種羥基羧酸或其内酯,及一或多種環狀伸烷基碳酸酯。 根據本發明,係提供式1分散劑(包括其鹽): T-X,(A)m-(B)n-Z 1 其中 T為氫或聚合作用終止基團之殘基; -4- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) 574061 A7 B7 五、發明説明(2 ) X為直接鍵或二價橋基: A為一或多種視需要經取代之CV5()-伸烷基或C2_5G-伸烷 基羥基羧酸或其内酯之殘基; B為一或多種視需要經取代之環狀伸烷基碳酸酯之殘 基; Z為酸基或驗基,或含一種酸基或驗基之部份,使得當 Z為鹼基或含鹼基之部份時,該T-X-(A)m-(B)n-基團可經由 醯胺及/或鹽鍵合物與Z連接; m及η為正整數;且 m+n為 2 至 200。 當Z為多價時,不只一個由T-X-(A)m-(B)n-表示之POAC 鏈可以與各Z連接,且這些POAC鏈可相同或不同。 該由-(A)m-(B)n-表示之POAC鏈可以是嵌段或無規共聚物 之POAC鏈,但是較佳為無規共聚物之POAC鏈。亦必需知 道A或B可以與該T-X基團連接。根據該聚合作用終止基團 T之性質,該由T-X-(A)m-(B)n-表示之POAC鏈可具有能夠 與Z連接之羥基或羧基端基。這些端基在下文中分別被稱 為 TP0ACS# 及 TP0AC酸。 當X為二價鍵結基團時,其較佳為-S-,-NR1-(其中R1為 氫或C丨-2〔)烷基)或特別為-C〇-或-〇-。 該聚合作用終止基τ較佳為可視需要經取代之Cmo-烴 基,其可以是芳基,雜芳基,烷基,烯基或環烷基。該烷 基及晞基可以具直鏈性或分支鏈性。 當T被取代時,該取代基可以是一或多種氧,硫,氮或 -5- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) A7 B7
574061 五、發明説明( 自素原子。因此’ 丁可包含一或多種醚,硫m驢 胺’胺基甲酸醋,醋(亦即,.oco-或coo_i),鐵或辖碑 胺基團。當T經鹵素取代時,該取代基較佳為氟,溴或特 别為虱。當T經氧取代時,該取代基可以是烷氧基,特別 為Ci燒氧基。 當T為芳基時,其較佳為苯基或莕基,且當τ為雜芳基 時,其較佳為σ塞吩基。然而,T最佳為烷基,缔基或環产 基。 Τ-Χ-可以是視需要經取代之脂肪族醇(T_〇H)之殘基,視 需要經取代之脂肪族硫醇(T_SH)之殘基,視需要經取代之 胺(T-NHRL)之殘基,或視需要經取代之脂肪酸(T_C〇〇H) 之殘基。 當T經取代時,該取代基較佳為自素,第三胺基或烷氧 基。然而T較佳未經取代。 T-OH之實例為甲醇’乙醇,正-丁醇,正-辛醇,正-壬 醇,正-癸醇,正·十二醇,油醇,硬脂醇,異丙醇,異丁 醇’第二-丁醇,2 -乙基丁醇,3-庚醇,2_乙基己醇, 3,5,5-三甲基己醇,3,7-二甲基辛醇及所謂蓋爾貝(Gue:rbet) 醇,例如,以品名愛索福(Isofol) (ex Condea GmbH)購自公 司之醇’並包括其混合物。蓋爾貝醇之特定實例為愛索福 (Isofol) 12,14T,16,18T,18E,20,24,28,32,32T 及 T-NHR1之實例為乙胺,丁胺,正-辛胺,丨,5•二甲基己 胺,第三-辛胺,2 -乙基己胺’二-異丙胺,2 -甲基丁 -6 - 本紙張尺度適用中國國家標準(CNS) A4规格(210 X 297公釐)
裝 訂
574061 A7 ___ _B7_ 五、發明説明(4 ) 胺’ 1 -乙基丙胺,雙(2 -乙基己胺),I,3 -二甲基丁胺, 3.3-二甲基丁胺,2 -胺基庚烷及3 -胺基庚烷。 T-COOH之實例為甲氧基醋酸,月桂酸,硬脂酸,蓖麻 油酸,2 -乙基丁酸,2 -乙基己酸,2 - 丁基庚酸,2 -己基 癸酸,2 -辛基十二酸及2 -癸基十四酸。該種類之分支鏈 月旨肪酸係以品名愛索卡(Isocarb) (ex Condea GmbH)購自公 司。其特定實例為愛索卡(Isocarb) 12,16,20,28,32, 34T及36 。 當T-C〇〇H含不只一個醚基團時,其較佳為聚伸烷基二 醇伸烯基羧基烷基醚,例如,購自Kao Chemicals GmbH之 阿基波(Akypo)酸。該阿基波酸如該式r〇(peg)CH2C〇〇H, 其中R為Cwo-燒基,且PEG為聚乙二醇之殘基。許多這些 阿基波酸係以混合物之型式購自公司。其特定實例為阿基 波(Akypo) RLM 45,R〇 50 VG,R〇 90 VG及LF2。 當丁為環烷基時’其較佳為環己基。因此,τ可以是該 環己鮮’環己胺’環己基硫醇或環己基幾酸之殘基。 當T為經由一或多種醚基團取代之烷基時,其較佳為聚 伸烷基醣單烷基醚,特別為數量平均分子量小於600之該 化合物。1¾單烷基醚之烷基較佳為c Μ ()·烷基,且特別為 C !·6-烷基。該聚伸烷基二醇較佳衍生自環氧丙烷及/或環 氧乙烷。較佳為單獨衍生自環氧乙烷之聚伸烷基二醇。其 持足貫例為聚乙一醇(350)單甲醇,三乙二醇單甲醚及該 乙氧基化蓋爾貝(Guerbet)醇。 该聚合作用終止基團T亦可以是類似可衍生A之羥基羧 本纸張尺度適用中8 8家標準(CNS) A4規格(21GX 297公》了 574061 A7 __ B7 五、發明説明(5 ) 酸(例如,經基乙酸)之該殘基° T較佳含不超過4 0個碳原子,更佳不超過3 〇個碳原 子,且尤佳不超過20個碳原子。 T亦較佳為脂肪族羧酸或脂肪族醇之該殘基。 A中該伸烯基較佳含不超過40個(更佳不超過3〇個,又 更佳不超過2 0個,且尤佳不超過1 〇個)碳原子。可獲得A 之羥基羧酸實例為羥基乙酸,乳酸,蓖麻油酸,6 - #至基己 酸,5-羥基戊酸,12-羥基硬脂酸,12-羥基癸酸,5-經基 十二酸,5 -羥基癸酸及4 -羥基癸酸。可衍生A之内酯實例 為/3 -丙内醋,視需要經统基取代之ε -己内醋及視需要經 坑基取代之5 -戊内醋。該ε -己内醋或5 -戊内酯中之燒基 取代基(群)較佳為Cu-烷基,且尤佳為烷基。如w0 98/19784所述,可經由使經烷基取代之環己酮進行氧化反 應以獲得該經烷基取代之ε -己内酯。其特定實例為7 -甲 基,3-甲基,5-甲基,6-甲基,4-甲基,5-第三-丁基, 4,6,6-三甲基及4,4,6-三甲基ε -己内酯。 Α更佳含可視需要經CN6-烷基取代之Ct.6-伸烷基鏈,且 尤佳為ε -己内醋。 可衍生Β之該環狀伸烷基碳酸酯較佳含一個5 -員環,尤 佳含6·員環❶環狀三亞甲基碳酸酯較佳视需要經Cl_6-烷 基,環烷基,攣.環烷基,C2-6-烯基’ Cw烷基氧-Ci6-烷 基及C2_6-烯基氧-Cw烷基。其特定實例為三亞甲基碳酸 酯,5,5-二甲基三亞甲基碳酸酯,5,5-二乙基三亞甲基碳 酸酯,5 -乙基-5-甲基三亞甲基碳酸酯,5 -甲基·5_丙基三 -8 - 本紙張尺度適用中國國家樣準(CNS) Α4規格(210 X 297公釐) 574061 A7 __ B7 五、發明説明(6 ) 亞甲基碳酸酯’ 5 -乙基-5 _ 丁基三亞甲基碳酸酯,5 -甲基 二亞甲基碳叙㈤’ 己丨布基二亞甲基碳酸酉旨及5 -乙 基-5-烷氧基甲基三亞甲基碳酸酯。 根據該最終分散劑是否使用於極性或非極性液體介質, 該m與η之比率可以有寬範圍不同。該m與η之比率較佳為 6:1至1:6。然而,最佳為m大於η。 m+ri較佳不超過1⑼,更佳不超過5〇,尤佳不超過2〇。 亦較佳為m+n不小於4。 當Z為酸基時,其較佳為硫酸根或鱗酸根。該鱗酸根可 以是單-,二-或三-磷酸根或其混合物’且其較佳經由使1 至3莫耳丁POAC醇與磷酸化劑之各磷原子反應而獲得。亦 可經由使該TPOAC醇與過量磷酸化劑(例如,聚磷酸)反應 以獲得該磷酸酯分散劑,其含咸信包括焦磷酸鹽之聚磷酸 部份。雖然該磷酸化劑中之鱗與各莫耳TP〇AC之比例可以 呈5:1過量,但是通常超過3:1過量並沒有好處。 當Z為鹼基或含鹼基之部份時,其較佳為聚胺或醯亞胺 之該殘基。聚胺之實例為聚烯丙胺及聚乙晞胺。該聚亞胺 較佳為聚(C2v伸烷基亞胺)(下文中稱為PAI);尤佳為聚 乙二亞胺(下文中稱為PEI)。該聚亞胺可以呈支鏈或較佳 分支鏈。如’例如 ’ Takeo Saegusa等人在 Macromolecules, 1972,第5冊’第4470頁中所述,可以使聚(n -醯基)伸烷 基亞胺進行水解以製成直鏈pEl,s。該具不同分子量之分支 鍵PEls可購自BASF及Nihon Shokubai °具不同分子量之聚 晞丙胺及聚(N -烷基)烷基胺可購自Nitto Boseki。具不同 -9- 本紙張尺度適用中國國家標準<CNS) A4規格(210X 297公釐) 574061 A7 _B7 五、發明説明(7 ) 分子量之聚乙晞胺可購自Mitsubishi Kasei。聚(丙二亞胺) 樹枝狀聚合物可購自DSM Fine Chemicals,而聚(醯胺基胺) 樹枝狀聚合物係以”史達波斯特(Starburst)"樹枝狀聚合物 購自Aldrich化學公司。 當Z為酸基或含酸基之部份,且該分散劑呈鹽型式時, 該鹽較佳為驗金屬鹽,例如,麵鹽,钾鹽,銅鹽,並包括 其混合物;驗土金屬鹽,例如,詞鹽,錢鹽,鋇鹽,並包 括其混合物;或該氨,胺’第四銨陽離子之鹽。適合之胺 貫例為正-丁胺’乙醇胺,二乙醇胺,三乙醇胺,胺基丙 醇’三乙胺,二甲基胺基乙醇,二甲基胺基丙胺。 當Z為驗基或含驗基之部份時’式1該分散劑可以呈著 色fe之鹽型式。該名辭”著色酸"係意指含至少1種(較佳^ 至6種)酸基(特別為磺酸基,膦酸基及叛酸基)之有機顏料 或染料。較佳之著色酸為g太花青鋼或其它深色顏料及特別 為每分子平均含0.5至3個碳酸基之磺酸化酞花青銅。該鹼 基亦可以呈有機酸鹽之型式,例如,甲基硫酸鹽之型式, 或呈第四銨鹽之型式,其中該未具p〇AC鏈之聚胺或聚亞 胺中之任何基團可以與烷化劑(例如,二硫酸烷基酯,例 如,硫酸二甲酯)反應。 根據本發明第一方面係提供一種分散劑,其係為式2聚 酯之磷酸酯或硫酸酯·· R-X 丨-(A)m(B)nH 2 其中 R為視需要經取代之烴基; -10-
574061 A7 B7 五、發明説明(δ ) X1 為 _〇·,-S-,-NR1 或-CO-:且 A,B,R1,m及η如前述定義3 如前述,於某些條件下,在該羥基羧酸或其内酯與該環 狀伸烷基碳酸酯進行聚合反應時,會損失C〇2,因此根據 本發明該第一方面之分散劑可視為式2 a聚酯之該磷酸酯 或硫酸酯: R-Xl-(0C-Al-0)m(B1-0)I1H 2a 其中 R,X1,m及η如前述; 為視需要經取代之Cmu-伸烷基或C2_5G-伸烯基;且 B1為視需要經Cif烷基取化之伸丙基。 根據本發明第二方面,係提供一種分散劑,其含具有至 少兩個式3 P0AC鏈之聚胺或聚亞胺,該下式3之P0AC鏈 可經由醯胺及/或鹽鍵合物與該聚胺或聚亞胺連接 -(A)m(B)nRM 3 其中 A,B,m及η如前文定義;且 R11為氫,烷基,芳基或醯基。 同樣,如前述,於某些條件下,在該羥基羧酸或其内酯 與該環狀伸燒基碳酸酯進行聚合反應時,會損失C〇2,因 此,根據本發明該第二方面之分散劑可視為具至少兩個下 式3 a POAC鏈之聚胺或聚亞胺,該式3 a之POAC鏈可經由 醯胺及/或鹽鍵合物與該聚胺或聚亞胺連接。 -(CO-ALOUBIo),,11 3a -11- 本紙張尺度適用中國國家標準(CNS) A4規格(210 x 297公釐) 574061 A7 B7 五、發明説明(Q ) y 其中 A1,B 1.,R11,m及η如前文定義。 各P〇AC鏈可經由以下鍵合物與該聚胺或聚亞胺連接: 在該POAC鏈之羰基端基與該聚胺或聚亞胺之第一或第二 胺基之氮原子間所形成之共價键合物-CON= ’或在該 POAC鏈之竣酸根端基與該聚胺或聚亞胺之經取代銨基之 正電荷氮原子間所形成之離子鹽鍵合物-COCXNHi。由於 該分散劑含至少兩個P0AC鏈,所以根據其製法所使用該 反應條件之激烈性,該分散劑可含酸胺與鹽鍵合物之混合 物。 本發明該第二方面之分散劑亦最好由下式4表示:
其中 X-WX表示該聚胺或聚亞胺; Y表示P0AC鏈,其可經由醯胺及/或鹽鍵合物與該聚 胺或聚亞胺連接; q為2至2000 ;且 P0AC如前文定義。 q較佳不少於4,且尤佳不少於1 0。q亦較佳不超過 1000,且尤佳不超過500。 該以Y表示之P0AC鏈與該以X-WX表示之聚胺或聚亞 胺之重量比亦較佳為30」至1 :1,更佳為20·. 1至3 : 1,且尤 佳為1 7: 1至7 Μ。 -12- 本紙張尺度適用中國國家標準(CNS) Α4規格(210 X 297公釐) 574061 A7 B7 五、發明説明(1〇 ) 該聚亞胺較佳為PEI。 該聚胺或聚亞胺之數量平均分子量較佳為500至 600,000,更佳為1000至200,000,且尤佳為1,000至 100,000 °
可以於5 0至250°C下,在惰性大氣中,視需要於聚合作 用終止化合物存在下,及於醋化作用催化劑存在下使一或 多種羥基羧酸,或其内酯與一或多種環狀脂肪族碳酸酯反 應以分別獲得該式2,2 a及3 / 3 a之POAC 。該溫度較佳不小於l〇(TC,且尤佳不小於 1 50°C。為了減少炭化之可能性,該溫度較佳不超過200 °C,且尤佳不超過180°C。雖然可根據門得列夫(Mendeleef) 元素週期表中之任何氣體提供該惰性大氣,但是其較佳為 氮。該酯化作用催化劑可以是鈦酸四烷基酯(例如,鈦酸 四丁酯),有機酸之鋅鹽(例如,醋酸鋅),脂肪族醇之錘 鹽(例如,丁酸結),甲苯績酸或強酸(例如,三氟醋酸或 硫酸)。根據該聚合作用終止化合物之性質,該酯化法之 產物為TPOAC醇或TPOAC酸。若該聚合作用終止化合物含 羥基,硫醇基,胺基或羧基,則該酯化法之產物為TPOAC S孚。 當在不使用聚合作用終止化合物之情況下,使用該環狀 伸烷基碳酸酯聚合該羥基羧酸或其内酯時,所形成該 POAC鏈兼含-OH及-C〇〇H端基。明顯可知,該-C〇〇H端基 可以與含-〇H,-SH或-NHR1-基團之聚合作用終止化合物 反應,得到一種TPOAC醇,但是更佳於該聚合作用終止化 -13- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) 574061 A7 B7 五、發明説明(U ) 合物存在下,經由使用該環狀伸坑基碳酸S旨聚合該輕基竣 酸或其内酯以形成該TPOAC醇。若該POAC鏈兼含-OH端基 及-COOH端基,則該-OH基亦可以與聚合作用終止化合物 (例如,叛酸)反應以形成一種TPOAC酸。作為另一種變 式,並就根據本發明第二方面之分散劑而言,該聚胺或聚 亞胺本身亦可作為該聚合作用終止化合物。 當該羥基羧酸及或其内酯與該環狀伸烷基碳酸酯反應 時,所形成該POAC鏈含醚,酯及碳酸根基團。自該環狀 伸烷基碳酸酯除去二氧化碳可產生該醚基,且該二氧化碳 之去除程度可受使所用任何酯化反應催化劑之性質影響。 該酯化反應催化劑可以是金屬鹽(例如,丁酸锆),或強有 機或無機酸,或路易斯(Lewis)酸。強酸之實例為三氟醋 酸,硫酸及鱗酸。當該聚合反應終止劑係衍生自輕基叛酸 時,則該酯化反應觸媒之選擇亦可影響該酯化反應是否經 由該羥基羧酸之該羥基或該羧基進行。當使用強酸催化劑 時,該酯化反應幾乎僅經由該經基進行。當使用金屬催化 劑時,該羥基羧酸之酯化反應可以經由該羥基端基及羧酸 端基進行。在這兩種情況下,可製成兼具羥基端基及羧基 端基之POAC鏈。 該可衍生B之環狀伸烷基碳酸酯之製法為在有機錫鹽 (例如,2 -乙基己酸亞錫)存在下,於120至200°C下使碳酸 二乙酯與該適合二元醇反應,得到一種視需要經取代之聚 (三亞甲基碳酸酯)。其可直接使用以製備根據本發明該分 散劑,其中該POAC鏈可組成嵌段共聚物。或者,可以使 -14- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) 574061 A7 B7 五、發明説明(12 )
該視需要經取代之聚(三亞甲基碳酸酯)經熱去聚合,並可 使用該視需要經取代之三亞甲基碳酸酯以製備無規P〇AC 鍵。 因此,根據本發明另一方面’係提供一種製備式1分散 劑之方法,其包括在惰性大氣中,視需要於聚合作用終止 化合物存在下,及在酯化作用催化劑存在下,使一或多種 經基竣酸或其内醋與一或多種環狀伸燒基碳酸醋反應。 該TPOAC酯可以與硫酸,氣磺酸或磷酸化劑(例如,聚 磷酸,P205或P0C13)反應,轉化成硫酸酯或磷酸酯。該反 應比該酯化反應更容易進行,且其通常於7 0至loot:溫度 下進行。如前述,根據所需該分散劑是否為單-,二-或三 磷酸酯或其混合物,或其是否含聚磷酸部份(例如,焦磷 酸跑)’該TPO AC醇與該磷酸化劑之各鱗原子之比率可以 自3 : 1至1 : 3不等。更佳為磷酸酯之混合物。 除了不需要該酯化反應催化劑外,可以於類似此等使用 以製備該TPOAC之條件下,使TPOAC與聚胺或聚亞胺反 應。 使用以製備根據本發明該第一方面之分散劑之該TPOAC 醇為新穎化合物。因此,根據本發明又另一方面,係提供 式2及2 a化合物。 根據本發明又另一方面,係提供式5及5 a之TPOAC酸 HO(A)m(B)n-R11 5 HO(CO-A,.〇)m(B1.〇)n.R11 5a 其中A,B,A1,B1,Ru,m及n如前文定義。r11較佳 ______-15- 本纸張尺度通用中國國家標準(CNS) A4規格(210 x 297公釐) 一 ~~ 13574061 典乙缔系不飽和基團。 如七迷’該分散劑特別可使用以將微粒狀固體分散在有 機介質中。 根據本發明另一方面,係提供一種含微粒狀固體及式1 分散劑之組合物。
根據本發明又另一方面,係提供一種含式1分散劑,微 粒狀固體及有機介質之分散劑。 存在於該分散液中之該固體可以是任何無機或有機固體 材質’其於相關溫度下,實質上不溶於該有機介質内,並 較佳於其内以微細緻型式安定化。 裝 訂 適合固體之實例為溶劑油墨之顏料;油漆及塑膠材質之 顏料,增量劑及填料;染料,特別為分散染料;溶劑染浴 油墨及其它溶劑應用系統之光學增亮劑及織物輔助劑;以 油為主並具逆乳性之鑽油之固體;乾洗流體之渣及固體顆 粒;微粒狀陶瓷材質;磁性材質及磁性記錄介質,防燃 劑,例如,此等可以以分散液之有機介質型式使用在塑膠 材質’殺生物劑,農業化學劑及藥劑者。 較佳固體為任何上述已知種類之顏料,例如,該丁
Edition of the Colour Index (1971)(及其後補增之修訂版)標 題為"Pigments”之章節中所述之顏料。無機顏料之實例為 一氧化鈦,氧化鋅,普魯士(Prusslan)藍,硫化鎘,氧化 鐵,銀朱,群青及該絡顏料,其包括絡酸鹽,銷酸鹽及混 合鉻酸鹽,與鉛,# ’鋇,鈣之硫酸鹽,及以名稱為鉻櫻 草色’絡檸檬色,中絡黃,鉻橘色,絡深紅色及鉻紅市售 -16-
574061 A7 B7
五、發明説明(14 U混,物及修,,……黃色至紅色顏料) …為此等得自該偶氮,雙偶濃縮偶氛 :: 丹士林1陰丹士林’_酿,以昆,異二笨并: 三菲二十井’㈣同及嶋㈣,特別樹青銅及Α 核自化衍生物’以及酸性’驗性與媒染染料之色殿。雖: 嚴格來說’碳黑為無機物,但是就其分散性質而言,立: 用更像有機顏,斗。較佳之有機顏料為0太花青(特別為社花 青銅)’單偶氮,雙偶氮,陰丹士林,慈嵌慈§昆, 及碳黑。 其它較佳固體為:增量劑及填料,例如,滑石,高嶺 土,矽石,重晶石及白微粒狀陶究材f,例如1 土,石夕石,氧化锆,氧化鈦,氮化矽,氮化硼,碳化矽, 碳化硼,混合矽-鋁氮化物及金屬鈦酸鹽;微粒狀磁性材 % ,例如,過渡金屬(特別為鐵及鉻)之磁性氧化物(例 如,γ -Fe2〇3,FeW4),及鈷雜摻鐵氧化物,氧化鈣,鐵 酸鹽,特別為鐵酸鋇;及金屬顆粒,特別為金屬鐵,鎳, 姑及其合金;農業化學劑,例如,各該殺真菌劑:福催芬 (flutnafen),卡本達金(carbendaZ1m),克羅索尼 (chlorothalonil)及門可幾(mancozeb);及滯燃劑,例如,|呂 三水合物及氫氧化鎂。 存在於本發明該分散劑中之該有機介質較佳為極性有機 介貝或貫質上非極性芳香烴或卣化烴。該極性有機介質係 指如 Crowley 等人在 Journal of Paint Technology,第 38 冊, 1966年’第 269頁名稱為"A Three Dimensional Approach to -17- 本紙張尺度適用中國國家標準(CNS) A4規格(210X297公釐) 574061 A7 B7 五、發明説明(15 )
Solubility"中所述,可形成中至強鍵之有機液體或樹脂。 如上述文章所定義,此種有機介質之氫鍵結數通常為5或 更多。 適合極性有機液體之實例為胺,醚(特別為低碳醚),有 機酸,酯,酮,二醇,醇,醯胺。此種適當強度之氫鍵結 液體之許多特定實例示於由Ibert Delian著述之書(書名為 裝 "Compatibility and Solubility",1968 年由 Noyes Development
Corporation出版),書中第39-40頁,表2 14中,且這些液 體全部皆屬於如文中該名辭”極性有機液體"之範圍。
線 較佳極性有機液體為二燒基酮,垸烴幾酸之貌基酷,垸 醇’特別為此種含至高(且包括)總數6個碳原子之液體。 該較佳及更特佳液體實例為二烷基與環烷基酮,例如,丙 酮’甲基乙基酮,二乙基酮,二-異丙基酮,甲基異丁基 酮,二-異丁基酮,甲基異戊基酮,甲基正·戊基酮及環己 酮;烷基酯,例如,醋酸甲酯,醋酸乙酯,醋酸異丙酯, 醋酸丁酯,甲酸乙酯,丙酸甲酯,甲氧基醋酸丙酯及丁酸 乙酿’二醇與乙二醇g旨及乙二醇酸,例如,乙二醇,)乙 氧基乙醇,3 -甲氧基丙基丙醇,3 -乙氧基丙基丙醇,醋 2 - 丁氧基乙酯’醋酸3 -甲氧基丙酯,醋酸乙氧基丙 跑及醋酸2 -乙氧基乙酯;燒醇,例如,甲醇,乙醇, 丙醇,異丙醇,正-丁醇及異丁醇;與二烷基醚及環狀 醚,例如,二乙醚及四氫呋喃。 該可單獨使用或併用上述極性溶劑之實質上非極性有機 液體為芳香烴,例如,甲苯,二甲苯;脂肪烴,例如,己 -18-
574061 A7
恍,庚^…辛疙,癸烷,石油餾出物(例如,石油溶劑, 礦物油,蔬菜油)及_化脂肪烴及芳香烴例如三氣· 晞,四氯乙缔及氯笨,., 〃乙 之實例包括聚醯胺 可作為+ ^明邊分散液型式之介質之適合極性樹脂實 為成膜,樹脂,例如,適於製造可使用於各種應用、(例 如,油♦及油墨)又油墨,油漆及晶片之樹脂。此種樹脂 例如
V e 1 sam i d 及 W 〇 1 famid 丨 M 及 纖維素醚,例如,乙基纖維素及乙基羥乙基纖維素。油漆 樹脂之實例包捂短油性醇酸/三聚氰胺-甲醛,熱固性丙烯 酸/二聚氰-甲醛,長油性醇酸及多介質樹脂,例如,丙 缔酸及尿素/駿 該樹脂亦f以是塑膠材質’例如,不飽和聚酯樹脂,其 包括可以使用強化纖維及填料製成之所謂片狀成形材料及 預製整體成形材料。此種成形材料在德國專利3,643,007及 P F Biuins 著述〈論文,名稱為,,unsaturated p〇|yester Technology ? Gordon and Breach Science publishers, 1976 ^ 第2 1 1頁土 2 j 8頁中有描述。聚g旨樹脂之實例為此等樹脂, 其中不飽和聚酯樹脂經聚苯乙烯或苯乙烯-丁二烯共聚物 共聚化’及特別為此種含碳酸鈣,氧化鎂或氫氧化鋁之聚 醋樹脂。該樹脂亦可以是丙烯酸,笨乙烯-丙烯酸或胺基 甲酸酯-丙缔酸樹脂。 若需要,該分散劑可含有其它成份,例如,樹脂(其實 際上並不包含在該有機介質内)結合劑,流化劑(例如,此 等在GB-A-1508576及GB-A-2丨08143中所描述者),抗沉降 -19- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297命釐) 574061
劑,增塑劑,均染劑及防腐劑。 一 I而$,遠分散劑含5至9 5重量。/。該固體,該精確量 取決於該固體性質,且該含量取決於該固體之性質及該固 體及有機介質之相對密度1如,以該分散液總重為基準 計’其中該固體為有機材質(例如,有機顏料)之分散液含 1 d至6 0重量%該固體,然而’其中該固體為無機材質(例 如’典機顏料’填料或増量劑)之分散液含4 〇至9 〇重量% 該固體。 可經由已知用以製備分散液之任何習用方法獲得該分散 液。因此,可以以任何順序混合該固體,該有機介質及該 分散劑,然後使該混合物經機械處理(例如,球磨,珠 磨,砂礫磨或塑膠磨)以使該固體顆粒減至適合大小,直 到形成孩分散液為止。或者,該固體可以獨立或併用該有 機介質或該分散劑經處理以減少其大小,然後添加該其它 成份或各成份,並攪動該混合物,得到該分散液。 若而要遠組合物呈乾型式,則該液體介質較佳具揮發 ^生因此可經由簡單分離方法(例如,蒸發),自該顆粒固 fe勿地移除該液體介質。然而,該分散液較佳含該液體 介質。 若琢乾組合物本質上由該分散劑及該微粒狀固體組成, 則以孩微粒狀固體重量為基準計,該乾組合物含至少〇 2% (更佳主少〇,5%,尤佳至少i 〇%)分散劑。以該微粒狀固體 4重量為基準計,該乾組合物含不超過1 〇〇重量% (較佳不 超過重量50%,更佳不超過重量20%,尤佳不超過t 〇重量 -20- ί紙張尺度適财S S家標準(CNS)織格(21〇 X 297公釐) 裝 訂
574061
%)分散劑
質内磨碎該微粒狀固體 液特別適於用以製備磨基劑,其 型樹脂結合劑存在下,在液體介
樹:*1狀固體。該微粒狀固體較佳不小於該 磨基刎重量之30重量%,尤佳不小於5〇重量%。 雖然3磨基劑中該樹脂之用量可以廣泛不同,但是其較 佳不小於邊磨基劑之連續/液相重量之丨〇%,且尤佳不小 於20重ΐ 〇/。。孩樹脂用量較佳不超過該磨基劑之連續/液 相重量之50%,且尤佳不超過4〇重量%。 雖然該磨基劑中該分散劑之用量取決於該微粒狀固體之 用量’但疋其較佳佔該磨基劑重量之〇 5至5 〇/〇。 含本發明該分散劑之分散液及磨基劑特別適於使用在以 下應用中:油漆,尤其高固體油漆;油墨,特別為快墨油 墨,凹板油墨及網板油墨;非水性陶瓷方法,特別為磁帶 塗佈法,刮刀法,擠製法及射出成形法。 亦可以使用該分散劑將微粒狀固體分散在塑膠材質(特 別為熱固性塑膠材質)内。適合之塑膠材質實例為聚晞 烴,聚Si胺’聚胺基甲酸醋,聚丙浠酸酯及聚自旨。 本發明該分散劑優於衍生自e -己内酯之已知分散劑。 更詳細地說’其在有機介肓(例如,溶劑)中具有優異溶解 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) 574061 A7 B7
五、發明說明(19 ) 性,且當於4 t下貯存長時間時不會分離或晶化。去貯存 於低溫時,於-24°C下可發生分離現象,但是〜曰二 < *溫或> 4-10°C時,該分散劑很容易再溶解。當併入油漆及冷、泰油 墨内時,本發明該分散劑可以使所形成油漆及油黑彳^到更 高光澤讀數,較佳混濁度,較低黏度及/或改良之絮疑棟 f ° 糸" 可經由以下實例進一步說明本發明,除非另有指定,其 中全部有關數量之參考值係以重量份數表示。 根據 T. Endo 等人在 Macromolecules 1997,30, 737 中所述 之方法製備該環伸烷基碳酸酯。 三亞甲基碳酸5,5-二甲酯 於〇 °C下以3 0分鐘在氮大氣中一滴滴添加三乙胺(24 56 份,242毫莫耳濃度ex Fisher)至2,2-二甲基-1,3-丙二醇(1 2 份,1 15毫莫耳濃度ex Aldrich)及氯甲酸乙酯(24.91份,230 毫莫耳濃度ex Aldrich)之四氫咬喃(260毫升)攪拌溶液内。 然後於2 0 t下攪拌各該反應物,並過濾以移除該三乙胺 鹽酸鹽。然後移除該溶劑,得到一種白色固體,並於0 °C 下使其在二乙醚(1〇〇毫升)内漿化,然後過濾(9.50份),熔 點 85-87°C。 經由使用等量所指定該二醇取代該2,2-二甲基-1,3_丙二 醇,以類似方法製備下述該環狀伸烷基碳酸酯。 碳酸酯 二醇一 · 三亞甲基碳酸5-甲酯 2-f基-1,3-丙二醇 5,5-環己-3-烯基三亞甲基碳酸酯 3-環己烯-1,丨-二甲醇 -22- 本紙張尺度適用中國國家標準(CNS) A4規格(210X297公爱) 574061 A7 __B7 五、發明説明(2〇 ) 三亞甲基碳酸5-乙基-5-烯丙氧基甲酯 三羥甲基丙烷單烯丙醚 三亞甲基碳酸5-甲基〇-丙酯 2-甲基-2-丙基-1,3·丙二醇 三亞甲基碳酸5-乙基-5-丁酯 2-乙基-2-丁基-1,3-丙二醇 三亞甲基碳酸5,5-二乙酯 2,2-二乙基-1,3-丙二醇 酸分散劑
實例 1 Dol, cap 12, DTC 6 ; 3:1P 於140°C下在氮大氣中,以攪掉添加丁酸錘(0.3份,呈 80% (w/w)之正-丁醇溶液型式,ex ABCR)至ε -己内酯(37.14 份,326毫莫耳濃度ex Aldrich),正-十二醇(5份,2 7毫莫 耳濃度ex Aldrich)及5,5-二甲基三亞甲基碳酸酯(21.18份, 163 φ莫耳濃度ex Lancaster)之混合物内。然後使該溫度上 升至180°C,並於該溫度下,在氮氣中再攪拌該反應物6小 時。冷卻後,獲得呈無色液體之該TPOAC醇(5 8份)。 於80-85 °C下在氮大氣中,以攪拌添加聚磷酸(2.44份, 含83% (w/w) p2〇5,毫莫耳濃度ex Fluka)至上述TPOAC醇 (5 0份,21.4毫莫耳濃度)内。然後使該溫度上升至90-95 t:,並於氮大氣中再攪拌該反應物6小時。冷卻後,獲得 如淡黃色黏狀油之該產物(4 5份)。其係為分散劑1。
實例 2 Is 14T1, cap 10? DTC 2.5; 1.5:1 P; DEA 於140°C下在氮大氣中以攪摔添加正-丁酸化锆(0.3份ex Fluka)至分支鏈醇類(5份,2 3毫莫耳濃度,Isofol 14T ex (:〇11心&(:1^11116〇11113^[),8-己内酯(26.29份’230 毫莫耳濃 度ex Aldrich)及5,5-二甲基三亞甲基碳酸酯(7.5份,57.6亳 莫耳濃度ex Lancaster)之混合物内。然後使該溫度上升至 -23- 本纸張尺度適用中國國家樣準(CNS) A4規格(210X297公釐) 574061 A7 B7 五、發明説明(21 ) I 80 °C,並持續該反應6小時。一整份顯示每亳克〇毫克 KOH/克之酸值,其表示聚合反應完成。 冷卻至9 0 t:後,添加聚磷酸(2.59份,18·3亳莫耳濃度, 83% (w/w) P2〇5 ex Fluke),並於9CTC下在氮大氣中攪拌各該 反應物6小時。該TPOAC磷酸酯之酸值為49.69 Ag K0H/ 克。然後經由添加二乙醇胺(3.5 8份’ 3 4亳莫耳濃度ex Aldnch)使該磷酸酯轉化成胺鹽,並於9 0 °C下攪拌該混合 物1小時。冷卻至2 5 °C後,獲得如黏狀樹膠之該產物(4 〇 份)。其係為分散劑2。 實例3至1 8 使用該指定原料醇,内酯及環狀伸烷基碳酸酯以類似製 備實例2,分散劑2之製法製備下表1中所列示各該分散 劑。欄内表示該醇内酯碳酸酯之圖說後之數字為莫耳量。 標題為”磷酸化劑”之欄中表示該磷酸化劑之圖說後之數字 為該TPOAC醇與該磷酸化劑之磷原子的莫耳比。應該注意 就實例1 7及1 8,分散劑1 7與1 8而言,該聚合作用終止基 團為脂肪族酸而非醇。 -24- 本纸張尺度適用中國國家標準(CNS) A4規格(210X297公釐) 574061 A7 B7 五、發明説明(22 ) 表1 實例 分散劑 TPOAC醇 磷酸化劑 酸值 MgKOH /克 胺 醇 内酯 碳酸酯 3 3 Do1 ε-cap 9 DTC3 PPA 1.5:1 48.33 DEA 4 4 〇c1 ε-cap 8 DTC4 PPA3:1 52.19 DEA 5 5 Is 18T 1 ε-cap 12 MPTC3 PPA 2.3:1 35.35 DEA 6 6 EtHe 1 ε-cap 8 DTC4 PPA 2.5:1 30.04 TEA 7 7 Is 24 1 ε-cap 10 DTC2 PPA 2.75:1 -25.41 DEA 8 8 Et Bu 1 ε-cap 9 MPTC3 PPA 2:1 35.52 DMAE 9 9 2-Bu 1 8-C3p 3 DTC 3.5 PPA 2.7:1 26.83 DEA 10 10 Is 36 1 ε-cap 8 DTC2 PPA 3:1 30.08 DEA 11 11 Is 16 1 ε-cap 4 DTC 1 PPA 2.25:1 - - 12 12 〇c1 ε-cap 6 MPTC PPA 2.5:1 - - 13 13 ls14T1 δ-val 10 1.5 PPA 2.5:1 37.38 DEA 14 14 TEGME1 ε-cap 3 MPTC PPA 3:1 - - 15 15 〇c De 1 ε-cap 8 2.5 PPA 2:1 DEA δ-val 2 DTC 1 16 16 〇c1 ε-cap 8 MPTC 2 PPA 3:1 DMAE δ-val 1 4-Mecap 1 DTC 2 17 17 LA 1 ε-cap 12 PPA 2.5:1 DEA 18 18 MAA1 ε-cap 10 PPA 2.25:1 DEA δ-val 2 DTC 3 MPTC 2.5 表1註腳 D 〇 為正-十二醇 ex Aldrich 〇c為正-辛醇ex Aldrich Is 18T為 Isofol 18T ex Condea Chemie GmbH Et He為2 -乙基己醇ex Aldrich -25- 本紙張尺度適用中國國家標準(CNS) A4規格(210X297公釐) 574061 A7 ___ B7_ 五、發明説明(23 )
装
is 24為 Isofol 24 ex Condea Chemie GmbH Et Bu為 2 -乙基丁醇 ex Aldnch 2-Bli為 2 - 丁醇 ex Fisher Is 36為 Isofol 36 ex Condea Chemie GmbH Is 16 為 Isofol 16 ex Condea Chemie GmbH O c為正-辛醇ex Aldrich Is 14T為[sofol 14T ex Condea Chemie GmbH TEGME為三乙二醇單甲醇ex Aldrich 〇c De為十八醇ex Aldrich L A為月桂酸ex Aldrich MAA為甲氧基醋酸ex Aldrich ε-cap為 ε -己内 g旨 ex Aldrich 5 -val為(5 -戊内酯 ex Fluka 4-Mecap為 4 -甲基-s-己内酯 ex WO 98/19784 DMAE為二甲基胺基乙醇ex Aldrich DTC為5,5-二甲基三亞甲基碳酸@旨ex Lancaster MPTC為5 -甲基-5 -丙基三亞甲基碳酸酷ex Sigma PPA為聚磷酸,其含83%(',%) P2〇5exFkika DEA為二乙醇胺 ex Aldrich TEA為三乙醇胺ex Aldrich 實例 1 9 DoaK cap 8, DTC 2; 2.25 S; DMEA 於150 °C在氮大氣中一起攪拌正-十二基胺(3.56份,‘ 0.0 192 莫耳濃度 ex Aldrich),ε -己内酯(17.54份,0. 154 莫耳 濃度ex Aldrich)及5二甲基三亞甲基碳酸酯(5份,0.0384 -26- 本紙張尺度適用中國國家標準(CNS) A4規格(210X 297公釐) 574061 A7 B7 五 、發明説明(24 ) 莫耳濃度ex Lancaster)。添加丁酸結(0.2份ex Fluka),並使 該溫度上升至1 75-1 80 :'C。於1 80 °C下在氮大氣中持續該反 應,費時6小時。冷卻至9 0 °C後,添加濃硫酸(0,83份), 並於9 0 °C下持續攪拌該反應6小時。該TPOAC醇之酸值為 3 8.15毫克KOHgm。添加二甲基胺基乙醇(1.5份ex Aldnch),並於9 0 °C下攪拌該反應混合物3小時。冷卻至 2 5 °C後,獲得如白色壌之該產物(2 4份)。其係為分散劑 19。 實例2 0 使該分散劑(2份)溶解在甲苯(1 0份)内,並於進行下述 步驟處理後以目視方法測定溶解度:於2 5 °C下貯存1 6小 時,於4°C下貯存3天,於-10°C下貯存5天,並於-10°C下 貯存5天,然後溫熱至2 5 °C。結果示於下表2中。 -27- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) 574061 A7 B7 五、發明説明(25 ) 表2 分散劑 貯存於25°C下 於4°C下3天 於-丨o°c下5天 1 先後於-1:C及25 °C下5天 1 透明 透 明 透明 透 明 2 透明 透 明 透明 透 明 j 透明 透 明 透明 透 明 4 透明 透 明 透明 透 明 5 透明 透 明 透明 透 明 6 透明 透 明 透明 透 明 7 透明 透 明 f.結晶 透 明 8 s 1 .混濁 透 明 透明 透 明 9 透明 透 明 f.結晶 透 明 10 透明 透 明 混濁 透 明 13 透明 透 明 透明 透 明 15 透明 透 明 透明 透 明 16 透明 透 明 透明 透 明 17 透明 透 明 透明 透 明 18 透明 透 明 透明 透 明 19 透明 f.結晶 f.結晶 透 明 對照物 s 1 .混濁 結 晶 膠化 結 晶 表2註腳 s 1為些微,而f為很少 對照物為TPOAC醇(其係在月桂醇(例如’,歐洲專利 1 64,8 1 7)存在下,經由聚合ε -己内酯而製成)之磷酸酯。 -28- 本紙張尺度適用中國國家標準(CNS) Α4規格(210 X 297公釐) 574061 A7 B7 五、發明説明(26 ) 實例2 1 白色顏料磨粉 、 、 使該分散劑(0·2份)溶解在4: 1 (乂)之甲氧基丙基醋酸酯 及正-丁醇(7.5份)混合物内。一起添加二氧化鈦白色顏料 (7.5份,Ti oxide TR 92)及3毫米直徑玻璃珠(17份),並使 用臥式搖動器磨碎該混合物1 6小時。使用任意等級A至E (好至不好)評估所形成分散劑之流動性。結果示於下表3 中 〇 表3
分散劑 流動性 1 C 2 B 3 B 4 C 5 C 6 C 7 B/C 8 C 9 B 10 C 13 C 15 B 16 B 17 B 18 B 19 B/C 對照物 C/D -29- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) 574061 A7 B7 五、發明説明(27 ) 表3註腳 對照物為TPOAC醇(其係在月桂醇存在下,聚合ε -己内 酯而獲得)之磷酸酯。 實例2 2 紅色氧化鐵顏料磨粉 除了使用分散劑(0.25份),紅色氧化鐵顏料(3份, 51。〇仃3115尺£(1128170\8八$?)及溶劑混合物(6.75份)取代實 例1 7所示之數量不同外,重覆實例1 7之步騾。結果示於 下表4中。 表4 分散劑 流動性 1 B/C 2 Β 3 Β 4 C 5 C/D 6 C/D 7 C/D 8 C/D 9 C/D 10 D 13 C/D 1 5 C 16 C 17 C 18 B/C 19 D 對照物 D 表4註腳 -30- 本紙張尺度適用中國國家標準(CNS) Α4規格(210 X 297公釐) _ 裝 訂 拳 574061 A7 B7
五、發明説明(28 ) 對照物如表3之該註腳所述。 鹼性分散 ;r——3 Glv I, ε-cap ]〇, MTC 3, PEI (12:1)
於i〇〇t下,在氮大氣中一起攪拌羥基乙酸(i 67份, 0.022莫耳濃度ex Aldnch),卜己内酯(25份,〇 22莫耳農 度ex Aldrich)及三亞甲基碳酸5 _甲酯(7 63份,〇 〇66莫耳農 度)。添加正磷酸(〇.13份),並於100。(:.下在氮大氣中再攪 拌1 0小時以完成該聚合反應。獲得如淺黃色液體+ TPOAC酸。添加聚乙二亞胺sp 2〇〇 (2 78份,原子量1〇 〇⑽ ex Nippon Shokubai) ’並使該溫度上升至i2〇°C,然後於 120°C下在氮大氣中一起攪拌各該反應物,費時6小時。冷 裝 卻至2 0 °C後,獲得如米黃色蠟之該產物(3 5份)。其係為 分散劑2 0。 實例2 3至2 7 訂
線 重覆實例2 3之步驟以製備下表5所列示之各該分散劑, 其中標題為TP0AC酸之欄中該數字係表示所使用該原料之 莫耳量,且其中該TPOAC酸與聚胺/聚亞胺之比率係為重 量配合比。 表5 實例 分散劑 TPOAC酸 TPOAC酸與聚胺聚亞胺 之比率 23 21 Gly 1, cap 9, EAT 4 SP 050 10 1 24 22 Gly 1, cap 8, EBT 4 SP 300 15 1 25 23 Gly l, cap 8, EBT 4 PAA 15 1 26 24 Gly L cap 12. MPT 3 SP 030 17 1 27 25 HMP 1. cap 9. MTC 3 SP 050 13 1 -31- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) 574061 A7 B7 五 、發明説明(29 表5註腳:
Gly為輕基乙酸ex Aldrich cap為 ε -己内醋 ex Aldiich EAT為甲基三亞甲基碳酸5 -乙基-5-晞丙基氧酯 £BT為三亞甲基碳酸5_乙基-5-丁酯 ΗΜΡ為2,2-雙(羥甲基)丙酸ex Aldrich MPT為三亞甲基碳酸5 -甲基-5-丙酯 MTC為三亞甲基碳酸5 -甲酯 SP 050為聚(乙二亞胺)原子量 5,000 ex Nippon Shokubai 5? 300為聚(乙二亞胺)原子量20,00〇6\川卩口〇11511〇1〇^&1 5卩030為聚(乙二亞胺)原子量3,000 “犯口口〇11511〇1<1^&1 PAA為聚缔丙胺,分子量17,000 ex Aldrich 實例2 8 使該分散劑(0.45份)溶解在4:1之甲氧基丙基醋酸酯及 正-丁醇(7.55份)混合物内。添加3毫米直徑玻璃珠(1 6份) 及紅色顏料(2 份,Monolite Rubine 3B ex Avecia),並使用 队式搖動機磨碎該混合物,費時1 6小時。然後移除該 珠,並經由手搖動,使用A至E (好至不好)任意等級評估 所形成該分散液之黏性。結果示於下表6中。 -32- 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐)
裝 訂
缘 574061 A7 B7 五、發明説明( 表6 分散劑 黏度 2 0 C 2 1 C 22 C 2 3 —---------------—-- C 24 C 25 _1 -ίϋϋ. RLM 45 1,cap 9, CHT 2, 2.5:1 Ρ 於150 °C下在氮大氣中攪拌聚乙二醇單甲醚亞甲基羧酸 (10份,0.0217莫耳濃度八]^|3〇111^45以〖(^(:1161111(:山 〇讯紐),8-己内醋(22.33份,0.196莫耳濃度以八1(11^)及 三亞甲基碳酸5,5-環己-3-烯基酯(7·3份,〇 〇43莫耳濃度)。 添加丁酸锆(0.3份ex Fluka),並於175-180 QC下在氮大氣中 擅:拌各该反應物,費時1 0小時。冷卻至9 〇 _ 9 5。0後,添加 聚鱗酸(1.5 1份)’並於90-95 °C下持續攪掉反應,費時6小 時。冷卻至2 0 °C後,獲得如黃色黏狀樹膠之該產物(3 5 份)。其係為分散劑2 6。 -33- 本紙張尺度適用中國國家標準(CNS) A4規格(210X297公釐)
Claims (1)
- 1· 一種式1分散劑,並包括其鹽; T-X-(A)m-(B)n-Z 1 其中 T為氫或聚合作用終止基團之殘基; X為直接鍵或二價橋基; A為一或多種視需要經取代之Ci s()•伸烷基或伸 燒基羥基羧酸或其内酯之殘基; B為一或多種環狀伸烷基碳酸酯之殘基; Z為酸基或鹼基,或含一種酸基或鹼基之部份使 考于當Z為驗基或含驗基之部份時,該T_x(A)m(g) ·基 團可經由醯胺及/或鹽鍵合物與Z連接; m及η為正整數;且 m+n為 2 至 200 〇 2·根據申請專利範圍第!項之分散劑,其中τ含不超過3 〇 個碳原子。 3·根據申請專利範圍第1或2項之分散劑,其中τ為燒基 或烯基。 4·根據申請專利範圍第1或2項之分散劑,其中τ為經一 或多種醚基團取代之烷基。 5 ·根據申凊專利範圍第4項之分散劑,其中τ為聚伸燒基 二醇單烷基醚之殘基^ 6·根據申請專利範圍第1或2項之分散劑,其中χ為<〇_ 或·〇·, 7·根據申請專利範圍第1或2項之分散劑,其中Α含視需 本紙張尺度適用中國困家糠準《CNS) Α4規格(21〇χ 297公釐) 574061 A 8 B8 C8 __________ D8 六、申請專利範圍 要經Cn’j:完基取代之(^_6-伸燒基鏈。 8·根據申請專利範圍第丨或2項之分散劑,其中A為該ε -己内酯之殘基。 9·根據申請專利範圍第丨或2項之分散劑,其中β係為以 下各物之殘基:三亞基碳酸酯,5,5-二甲基三亞甲基碳 酸酯,5,5-二乙基三亞甲基碳酸酯,5 -乙基-5-甲基三 亞甲基碳酸酯,5-甲基-5-丙基三亞甲基碳酸酯,三亞 甲基碳酸5-甲酯,三亞甲基碳酸5,5-環己-3-缔基酯, 三亞甲基碳酸5 -乙基-5-婦丙氧基甲酯及三亞甲基碳酸 5 -甲基-5-丁酯。 !〇·根據申請專利範圍第1或2項之分散劑,其中該m : η之 比為6 : 1至1 : 6。 11·根據申請專利範圍第i或2項之分散劑,其中m+n不大 於20 〇 12·—種分散劑,其係為式2聚酯之硫酸酯或磷酸酯,並包 括其鹽; R-Xl-(A)m(B)nH 2 其中 R為視需要經取代之烴基; X1 為-0-,,-NR1 或-CO-; A為一或多種視需要經取代之Cns()·伸烷基或c2 5(r 伸缔基羥基羧酸或其内酯之殘基; B為一或多種環狀伸烷基碳酸酯之殘基; R為Η或〇1·2〇-燒基; -2- 本纸張尺度遴用中國β家揉準(CNS) Α4規格(210 X 297公釐) 574061 A8 B8 C8 _________ D8 ___ 六、申請專利範圍 η及m為正整數;且 n+m為 2 至 200 ° 13·根據申請專利範圍第1 2項之分散劑,其係為式2 a聚酯 之硫酸酯或磷酸酯 R-Xl-(0C-Al-0)m(Bl-0)nH 2a 其中 R為視需要經取代之烴基; X1 為-0-,-S-,-NR1 或-CO-; A 1為視需要經取代之CN5(r伸烷基或C2.5〇-伸烯 基; B1為視需要經Cl.6_烷基取代之伸丙基; R1為Η或Cuw烷基; m及η為正整數;且 n+m為 2 至 200。 14·根據申請專利範圍第1項之分散劑,其中該分散劑為 單-’二-或三-鱗酸g旨,或其混合物。 15·根據申請專利範圍第丨項之分散劑,其中該分散劑為一 種胺鹽。 16·根據申請專利範圍第!項之分散劑,其係如式4 X~*丁 *— X 4 (Y)q 其中 X—*一 * — X表示聚胺或聚亞胺; _ γ表示聚氧伸烷基羰基鏈(POAC),其可經由醯胺及/ -3- 本纸張尺度適用中理國家標準(CNS) A4规格(210 X 297公釐) 574061 Λ8 B8 C8 p-_______ D8 六、申請專利範圍 或鹽鍵合物與該聚胺或聚亞胺連接;且 q 為 2 至 2000 0 口·根據申請專利範圍第1 6項之分散劑,其中該以γ表示 之POAC鏈與該聚胺或聚亞胺之重量比為30:1至1:1。 18·根據申請專利範圍第1 6或1 7項之分散劑,其中該聚亞 胺為聚乙二亞胺。 19. 一種製備含聚氧伸烷基羰基(P〇AC)鏈之分散劑之方 法,其包括於50至250°C下,視需要於聚合作用終止化 合物存在下,在惰性大氣中及於酯化作用催化劑存在 下使一或多種羥基羧酸或其内酯與一或多種環狀伸烷 基碳酸酯反應。 20. —種式2化合物 R.X!-(A)m(B)nH 2 其中 R為視需要經取代之烴基; X1 為-0-,-S-,-NR1 或-CO-; A為一或多種視需要經取代之C 1.50·伸坑基或C2.50-伸缔基經基叛酸或其内酯之殘基; B為一或多種環狀伸烷基碳酸酯之殘基; R1為Η或Cwo-烷基; η及m為正整數;且 n+m為 2 至 200 〇 21. —種式2 a化合物 R-Xl.(OC.A1.〇)m(B,.〇)nH 2a -4- 本纸張尺度適用中《 *家搮準(CNS) A4規格<21Ώ X 297公釐) 574061 A 8 B8 C8 D8 六、申請專利範圍 其中 R為視需要經取代之烴基; X1 為-0-,-S·,-NR1 或-CO-; A 1為視需要經取代之Cwo-伸烷基或C2_5(r伸晞 基; B1為視需要經C!.6-烷基取代之伸丙基; R1為Η或Cu-烷基; η及m為正整數;且 n+m為 2 至 200 0 22. —種組合物,其含微粒狀固體及如申請專利範圍第1項 之分散劑β 23· —種組合物,其含微粒狀固體,有機介質及申請專利 範圍第1項之分散劑。 24· —種磨基劑、油漆或油墨,其含顏料,有機介質及如 申請專利範圍第1項之分散劑。 25· —種組合物,其含微粒狀固體,塑膠材質及如申請專 利範圍第1項之分散劑。 本紙張尺度適用中國國家搮準<CNS) Α4規格<210X297公釐)裝
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- 2002-03-15 US US10/474,306 patent/US7361692B2/en not_active Expired - Fee Related
- 2002-03-15 AT AT02714325T patent/ATE299044T1/de not_active IP Right Cessation
- 2002-03-15 JP JP2002583077A patent/JP2004537394A/ja active Pending
- 2002-03-15 WO PCT/GB2002/001266 patent/WO2002085507A2/en active IP Right Grant
- 2002-03-15 CN CNB028116658A patent/CN1309463C/zh not_active Expired - Fee Related
- 2002-03-15 EP EP02714325A patent/EP1383595B1/en not_active Expired - Lifetime
- 2002-03-15 AU AU2002246240A patent/AU2002246240A1/en not_active Abandoned
- 2002-03-15 DE DE60204956T patent/DE60204956T2/de not_active Expired - Lifetime
- 2002-03-22 TW TW91105671A patent/TW574061B/zh not_active IP Right Cessation
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2008
- 2008-02-01 US US12/024,388 patent/US8076378B2/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI393585B (zh) * | 2004-12-23 | 2013-04-21 | Lubrizol Ltd | 分散劑 |
Also Published As
Publication number | Publication date |
---|---|
EP1383595A2 (en) | 2004-01-28 |
AU2002246240A1 (en) | 2002-11-05 |
WO2002085507A3 (en) | 2002-12-19 |
EP1383595B1 (en) | 2005-07-06 |
US20080127857A1 (en) | 2008-06-05 |
DE60204956D1 (de) | 2005-08-11 |
GB0109708D0 (en) | 2001-06-13 |
JP2004537394A (ja) | 2004-12-16 |
ATE299044T1 (de) | 2005-07-15 |
US8076378B2 (en) | 2011-12-13 |
US20040112250A1 (en) | 2004-06-17 |
US7361692B2 (en) | 2008-04-22 |
DE60204956T2 (de) | 2006-04-27 |
CN1309463C (zh) | 2007-04-11 |
WO2002085507A2 (en) | 2002-10-31 |
CN1531457A (zh) | 2004-09-22 |
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