CN100542664C - 分散剂 - Google Patents
分散剂 Download PDFInfo
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- CN100542664C CN100542664C CNB2005800444853A CN200580044485A CN100542664C CN 100542664 C CN100542664 C CN 100542664C CN B2005800444853 A CNB2005800444853 A CN B2005800444853A CN 200580044485 A CN200580044485 A CN 200580044485A CN 100542664 C CN100542664 C CN 100542664C
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- 239000002270 dispersing agent Substances 0.000 title claims abstract description 81
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 31
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000002596 lactones Chemical class 0.000 claims abstract description 19
- 239000004202 carbamide Substances 0.000 claims abstract description 17
- 150000002466 imines Chemical class 0.000 claims abstract description 15
- 229920000768 polyamine Polymers 0.000 claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- -1 Imino group Chemical group 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 35
- 239000007787 solid Substances 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 24
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 claims description 20
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000002170 ethers Chemical class 0.000 claims description 8
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims description 7
- 239000004359 castor oil Substances 0.000 claims description 7
- 235000019438 castor oil Nutrition 0.000 claims description 7
- 238000000576 coating method Methods 0.000 claims description 7
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000007639 printing Methods 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 5
- 229920000083 poly(allylamine) Polymers 0.000 claims description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 58
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000003513 alkali Substances 0.000 description 20
- 239000006185 dispersion Substances 0.000 description 18
- 239000000376 reactant Substances 0.000 description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000000049 pigment Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000012265 solid product Substances 0.000 description 8
- 229910052726 zirconium Inorganic materials 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 229920002873 Polyethylenimine Polymers 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 229940070765 laurate Drugs 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 235000007466 Corylus avellana Nutrition 0.000 description 3
- 240000003211 Corylus maxima Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 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 3
- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 description 3
- 229950004531 hexyldecanoic acid Drugs 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 235000019239 indanthrene blue RS Nutrition 0.000 description 3
- 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 3
- 239000003112 inhibitor Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
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- LMHJFKYQYDSOQO-SECBINFHSA-N (5r)-5-hydroxydecanoic acid Chemical compound CCCCC[C@@H](O)CCCC(O)=O LMHJFKYQYDSOQO-SECBINFHSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N 12-hydroxylauric acid Chemical compound OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-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
- QQAVZEYXLCYOKO-UHFFFAOYSA-N 4-Hydroxycapric acid Chemical compound CCCCCCC(O)CCC(O)=O QQAVZEYXLCYOKO-UHFFFAOYSA-N 0.000 description 2
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- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
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- 229920000180 alkyd Polymers 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 description 2
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- 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
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 2
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- 239000011651 chromium Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
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- 125000001072 heteroaryl group Chemical group 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
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- 239000002245 particle Substances 0.000 description 2
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- 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 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- LXNOENXQFNYMGT-UHFFFAOYSA-N xi-5-Hydroxydodecanoic acid Chemical compound CCCCCCCC(O)CCCC(O)=O LXNOENXQFNYMGT-UHFFFAOYSA-N 0.000 description 2
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Abstract
本发明提供了一种式(1)的分散剂:T-V-(A)m-U-Z-Wx,式(1),其中,T是聚合末端基团;V是直接键或二价连接基团;A是羟基羧酸或内酯的残基;U是直接键或二价连接基团;Z是多胺或多亚胺的残基;W是氧化物或脲的残基;m是2-2000;和x是1至不带基团T-V-(A)m-U-的Z中可以利用的氨基和/或亚氨基的最大数值。
Description
相关申请的交叉引用
本申请是按照2004年12月23日提交的临时申请60/638,634提交的。
发明领域
本发明涉及将颗粒固体分散于有机介质中的分散剂,并涉及研磨料、涂料和油墨,包括喷墨打印用的油墨。
发明背景
许多专利文献公开了由聚(C2-4-烷撑亚胺)(下面的PAI)例如聚乙烯亚胺(下面的PEI)获得的聚酯胺分散剂,其中结合有聚酯链。该聚酯链可得自如US 4,224,212中公开的12-羟基硬脂酸或者它可得自两种或多种不同的羟基羧酸或其内酯,如US 5,700,395和US6,197,877中公开的。现已发现可以进一步改进,由此将聚烷撑亚胺中的任意氨基和/或亚氨基与氧或脲反应。改进包括如下至少一种:颜料分散体的优异的流动性;用于酸催化的、环氧和异氰酸酯涂布过程;和当暴露于紫外线下时耐变色。
发明内容
因此,根据本发明,提供了式(1)的分散剂:
T-V-(A)m-U-Z-Wx
式(1)
其中
T是聚合末端基团;
V是直接键或二价连接基团;
A是一个或多个不同羟基羧酸或其内酯的残基;
U是直接键或二价连接基团;
Z是多胺或多亚胺的残基;
W是氧化物或脲的残基;
m是2-2000;和
x是1至不带基团T-V-(A)m-U-的Z中可以利用的氨基和/或亚氨基的最大数值(Z的未取代价)。
发明详述
本发明提供了一种如上所述的组合物。
在一个实施方式中,有至少两个基团T-V-(A)m-与Z相连并且它们可以相同或不同。
V是二价连接基团并且在一个实施方式中是-CO-。
当T是聚合末端基团时,它包括羧酸R-COOH或醇R-OH的残基,并且其中R是任选取代的C1-50-烃基。
在一个实施方式中,R含有不大于40、或者不大于30或者不大于20个碳原子。
R可以是芳基、芳烷基、杂芳基、环烷基或烷(烯)基,它们可以是直链或支链。在一个实施方式中,R是烷基。
当R是芳基时,它包括苯基或萘基,可以用C1-20-烷基、C1-20-烷氧基、卤素、腈或苯氧基任选取代。R-COOH的具体实例有苯甲酸或萘-2-甲酸。R-OH的具体实例有苯酚、2-萘酚、4-辛基苯酚和4-壬基苯酚。
当R是芳烷基时,它包括苯基乙酸、萘氧基乙酸、苯甲醇或2-羟基乙基苯基。
当R是杂芳基时,它可以是噻吩基。
当R是环烷基时,它包括C3-8-环烷基,其合适实例有环丙基或环己基,它们可以用一个或多个C1-6-烷基任选取代。
如上所述,R是任选取代的烷基,例如,含一个或多个醚基的烷基。R-COOH的合适实例有甲氧基乙酸、丙酸、丁酸、己酸、辛酸、月桂酸、正十二烷酸、硬脂酸、2-乙基丁酸、2-乙基己酸、2-丁基辛酸、2-己基癸酸、2-辛基正十二烷酸和2-癸基正十四烷酸。这类支链烷基羧酸可以商品名Isocarb(得自Condea GmbH)获得并且具体实例有Isocarb 12、16、20、28、32、34T和36。许多羧酸可以混合物商购获得。
当R经取代时,R-COOH内可以含有一个或多个醚基或者至少两个醚基。这些醚基可以构成含丙氧基、乙氧基或丁氧基(包括其混合物)的聚C1-4-亚烷氧链。在一个实施方式中,混合物包括丙氧基/乙氧基聚醚链。在该聚醚链含有多于一个的不同亚烷氧基单元的情况下,通常亚乙氧基的量不小于聚醚链重量的50%、不小于70%或不小于90%。在一个实施方式中,聚醚链完全由亚乙氧单元构成。
当R-COOH含有聚醚链时,它包括聚烷撑氧基单C1-24-烷基醚。一个实施方式中该聚亚乙氧基单烷基醚的重均分子量不大于2000、不大于1000或不大于600。式R1O-(CH2CH2O)qCH2COOH的单烷基醚羧酸可以商品名Akypo从Kao Chemicals GmbH获得。具体实例有Akypo LF1(R1是C8、q=5)、Akypo LF2(R1是C8、q=8)、Akypo RLM 25(R1是C12/C14、q=2.5)、Akypo RLM 45 CA(R1是C12/C14、q=4.5)、AkypoRO 20 VG(R1是C16/C18、q=2)和Akypo RO 50 VG(R1是C16/C18、q=5)。
R-OH的实例有甲醇、乙醇、正丁醇、正己醇、正辛醇、正癸醇、正十二烷醇、正十四烷醇、正十六烷醇、正十八烷醇、油醇、异丙醇、异丁醇、叔丁醇、2-乙基丁醇、3-庚醇、2-乙基己醇、3,5,5-三甲基己醇、3,7-二甲基辛醇和所谓的Guerbet醇例如可以商品名Isofol获得的(得自Condea GmbH)(包括其混合物)。Guerbet醇的具体实例有Isofol 12、14T、16、18T、18E、20、24、28、32、32T和36。
在一个实施方式中,R-OH中的R是取代的烷基并且它含有一个或多个醚基,并且在另一实施方式中含有不小于两个醚基。醚基可以构成含丙氧基、亚乙基氧基或亚丁基氧基重复单元(包括其混合物)的聚C1-4-烷撑氧基链。在聚醚链含有多于一个不同烷撑氧基重复单元的情况下,在一个实施方式中亚乙基氧基可以不小于聚醚链重量的50%存在,在另一实施方式中可以不小于70%存在,并且在另一实施方式中可以不小于90%存在。在一个实施方式中,聚醚链只含亚乙氧基单元。在一个实施方式中,这类醇是聚亚乙基氧基单C1-24-烷基醚,例如C1-12-单烷基醚或C1-6-单烷基醚。典型地,由于单甲基醚容易获得而使用它们。一个实施方式中聚亚烷基氧基单烷基醚的重均分子量不大于2000,在另一实施方式中不大于1000。聚亚乙氧基单甲基醚的具体实例具有350、550和750的重均分子量。聚醚单烷基醚的其它实例有与环氧乙烷反应的Guerbet醇,包括重均分子量为250-750的那些。
由其获得A的羟基羧酸通常是羟基-C2-20-亚烯基羧酸或羟基-C1-20-亚烷基羧酸。该亚烷(烯)基可以是直链或支链。羟基羧酸的实例有蓖麻油酸、12-羟基硬脂酸、6-羟基己酸、5-羟基戊酸、12-羟基十二烷酸、5-羟基十二烷酸、5-羟基癸酸、4-羟基癸酸、10-羟基十一烷酸、乳酸和乙醇酸。
如上所述,A可以得自内酯。合适的内酯的实例有β-丙内酯、任选烷基取代的ε-己内酯和任选烷基取代的δ-戊内酯。一个实施方式中ε-己内酯和δ-戊内酯中的烷基取代基包括C1-6-烷基或C1-4-烷基并且可以是直链或支链。合适的内酯的实例有ε-己内酯及其7-甲基-、3-甲基-、5-甲基-、6-甲基-、4-甲基-、5-叔丁基-、4,4,6-三甲基-和4,6,6-三甲基-类似物。
可以使用羟基羧酸和/或内酯的混合物。
当A得自任选取代的ε-己内酯和一个或多个其它内酯时,ε-己内酯在一个实施方式中以不小于内酯总重量的50%、不小于70%或不小于90%存在。在一个实施方式中,A得自ε-己内酯本身。
R-COOH和羟基羧酸或内酯的选择可以在很大范围内变化并且取决于颗粒固体和颗粒状有机介质的性质。当有机介质为非极性的时,羟基羧酸经常含有不小于8个碳原子(不包括羧酸基)。非极性有机介质的有用的分散剂可以由12-羟基十二烷酸、5-羟基十二烷酸、5-羟基癸酸、4-羟基癸酸获得。在一个实施方式中,非极性有机介质用的分散剂可以由12-羟基硬脂酸或蓖麻油酸获得。在为非极性有机介质的情况下,含有8个或更多碳原子的这些羟基羧酸也可以与含有高达6个碳原子(不包括羧酸基)的羟基羧酸或其内酯混合。在一个实施方式中,以羟基羧酸或内酯的总量为基础,该混合物中含有高达6个碳原子的羟基羧酸的量不大于50%或不大于30%。含羟基羧酸的混合物的非极性介质的有用的分散剂是A可得自12-羟基硬脂酸和ε-己内酯的混合物的那些和可得自蓖麻油酸和ε-己内酯的混合物的那些。
当有机介质为极性或树脂复合物时,A在一个实施方式中可得自含高达6个碳原子(不包括羧酸基)的羟基羧酸或其内酯。因此,极性有机介质和树脂复合物用的分散剂的一个重要分类是A可得自ε-己内酯,它可以混合有C1-6-烷基取代的ε-己内酯、C1-6-烷基取代的δ-戊内酯或δ-戊内酯本身。在一个实施方式中,ε-己内酯的量不小于羟基羧酸或内酯的总量的50%或不小于70%。
在另一实施方式中,这类分散剂,T-V-(A)m-U-代表的不同聚酯链可以与Z相连,其中一个聚酯链可得自含不小于8个碳原子(不包括羧酸基)的羟基羧酸,第二个聚酯链可得自含高达6个碳原子(不包括羧酸基)的羟基羧酸或其内酯。这种分散剂在极性和非极性有机介质中具有较大的效用,但是比针对各个有机介质专门设计的效用低。
当U是二价键时,它包括烯化不饱和基团的残基,此时Z是碱性基团或者含碱性基团的部分。在一个实施方式中,含烯化不饱和基团的残基含有羟基并且得自(甲基)丙烯酸(申请人使用(xxxx)代表任选存在的取代基(在这种情况下,甲基在丙烯酰基的β碳上))。含烯化不饱和基团和羟基的化合物的实例有(甲基)丙烯酸羟基乙酯、(甲基)丙烯酸羟基丙酯、(甲基)丙烯酸羟基丁酯、聚亚乙基单(甲基)丙烯酸酯、聚丙二醇单(甲基)丙烯酸酯、聚乙二醇聚四亚甲基二醇单(甲基)丙烯酸酯和聚丙二醇聚四亚甲基二醇单(甲基)丙烯酸酯(例如Blemmer PE、Blemmer PP,得自Nihon Yushi Co Ltd)。在一个实施方式中,烯化不饱和基团可得自(甲基)丙烯酸羟基乙酯。
本领域技术人员清楚,也可以由式3的TPOAC酸,由醇ROH开始并通过与可以接着与胺、多胺或多亚胺反应的二元酸或酐反应将其转变成羧酸末端的聚合物,制备分散剂。这些分散剂是式1的那些,其中V或U是二元酸或酐的残基。
Z代表的多胺的实例有聚乙烯胺和聚烯丙胺。
多亚胺在一个实施方式中是聚(C2-6-烷撑亚胺)和或聚乙烯亚胺(下面的PEI)。多亚胺可以是直链或支链。直链聚乙烯亚胺可以通过水解聚(N-酰基)烷撑亚胺制得,如Takeo Saegusa等在Macromolecules,1972,Vol:5,4470页中所述。不同分子量的支链聚乙烯亚胺可以从BASF和Nihon Shokubai商购获得。不同分子量的聚烯丙胺和聚-(N-烷基)烯丙基胺可以从Nitto Boseki商购获得。不同分子量的聚乙烯胺可以从Mitsubishi Kasai商购获得。聚(丙烯亚胺)枝聚物可以从DSM Fine Chemicals商购获得,聚(酰氨基胺)枝聚物可以"Starburst"枝聚物从Aldrich Chemical Co商购获得。
多胺或多亚胺在一个实施方式中的数均分子量在500-600,000或1,000-200,000或1,000-100,000或1200-约20,000或100,000的范围内。
在一个实施方式中,m不大于1000或不大于100,例如,不大于50或不大于20。
当W是脲的残基时,当与脲反应时Z中的自由亚氨基或氨基数可以在很大范围内变化,高达不带基团T-V-(A)m-U的最大可用氮原子。
当W是氧化物的残基时,不带基团T-V-(A)m-U的Z中的任意氨基或亚氨基可以经过与氧(包括空气)或过氧化物例如过氧化氢或过硫酸铵反应转变成N-氧化物。
当T是酸R-COOH的残基并且V是直接键时,分散剂在一个实施方式中可以得自式2的酸:
R-CO(A)m-OH
式(2)
这在下面称之为TPOAC酸。
本发明的分散剂典型地具有两个或多个与聚铵或多亚胺相连的式(3)的链:
T-V-(A)m-U
式(3)
其中T、V、A、U和m如上面定义的。
式(3)代表的每一链可以与多胺或多亚胺通过在TPOAC酸的末端羰基和多胺或多亚胺的伯或仲氮原子之间形成的共价酰胺键-CON<相连,或者通过在TPOAC酸的末端-COOH基团和多胺或多亚胺中取代铵基的带正电的氮原子之间形成的离子键-COO-HN+=相连。由于分散剂含有两个或多个链T-V-(A)m-U,因此它可以含有酰胺和盐键的混合物,这取决于其制备所用的反应条件。
本发明第一方面的分散剂可以方便地用式(4)表示:
式(4)
其中,
X-*-*-X代表多胺或多亚胺;
Y代表链T-V-(A)m-U,它们可以相同或不同并且经酰胺和/或盐键相连;和
r是2-2000;并且
T、A、B.和m以及W如上面定义的。
在一个实施方式中,r不小于10。在另一实施方式中,r不大于1000或不大于500。
在一个实施方式中,Y与X-*-*-X的重量比是30:1-1:1,或者20:1-2:1。
在一个实施方式中,X-*-*-X代表聚(C2-4-烷撑亚胺)(PAI)或聚乙烯亚胺(PEI)。
PAI在一个实施方式中具有500-600,000或1,000-200,000或1,000-100,000,例如1,200-70,000的数均分子量。
本发明第一方面的分散剂典型地通过预先形成的TPOAC酸与聚烯丙胺、聚乙烯胺或PAI在100-150℃的温度下(通常在惰性环境下)反应制得。
TPOAC酸在一个实施方式中是通过一种或多种(a)羟基羧酸、(b)内酯、(c)氨基羧酸或(d)其混合物反应制得的。在一个实施方式中,TPOAC酸是两种或多种(a)-(c)的混合物。
Y代表的链可以相同或不同。
TPOAC酸在一个实施方式中是在50-250℃的温度下,任选在有羧酸R-COOH的情况下并任选在有酯化催化剂的情况下制得的。在一个实施方式中,该温度不小于100℃或不小于150℃。为了使最终产物的任意碳化最小化,温度通常不大于200℃。惰性环境可以通过周期表的任意惰性气体提供,但是通常是氮。
酯化催化剂可以是本领域任意已知的并且包括钛酸四烷基酯,例如钛酸四丁酯、有机酸的锌盐,例如,乙酸锌、脂族醇的锆盐,例如,异丙醇锆、苯磺酸或强有机酸例如三氟乙酸。
在本发明的另一实施方式中,提供了式(4)的分散剂,其中U代表式(5)的链残基:
式(5)
其中
A、R和m如上面定义的;
R2是氢或C1-4-烷基;和
R3是含有高达10个碳原子的脂族或芳族残基,它任选含有可由环氧丙烷和/或环氧乙烷获得的聚醚残基。
当R2是C1-4烷基;并且在一个实施方式中是甲基。
R3是C2-6-亚烷基;并且在一个实施方式中是C2-4-亚烷基。
含有式(6)的链残基的分散剂可以通过多胺或多亚胺与式(6)的化合物的Michael加成反应方便地制得:
式(6)
其中A、R、R2、R3和m如上面定义的。
式(6)的化合物可以通过含羟基的(烷基)丙烯酸衍生物与预制的式2的TPOAC酸在50℃-150℃或80℃-120℃的温度下,在有空气或氧的情况下反应方便地制得。在一个实施方式中,该反应是在有酯化催化剂例如钛酸四烷基酯,例如,钛酸四丁酯、金属醇盐例如钛酸四异丙基酯、锡催化剂例如氯化亚锡、辛酸亚锡或单丁基氧化锡或酸催化剂例如甲苯磺酸或三氟乙酸的情况下进行的。该反应在一个实施方式中是在有抑制式8的化合物或(烷基)丙烯酸衍生物的自聚合反应的聚合抑制剂的情况下进行的。聚合抑制剂的实例有(甲基)对苯二酚和酚噻嗪。氧也起聚合抑制剂的作用。
多胺或多亚胺和式7的化合物之间的反应可以通过在10-130℃或20-100℃之间加热进行。
式(5)的化合物和多胺或多亚胺之间的反应可以任选在有对反应物为惰性的溶剂的情况下进行。合适的溶剂的实例有烃例如甲苯、二甲苯和solvesso(芳香石油烃)、酮类例如丙酮、甲基乙基酮和甲基异丁基酮、烷醇例如正丁醇和异丙醇和酯类例如乙酸丁酯、己二酸二甲酯、琥珀酸二甲酯和戊二酸二甲酯。
如上所述,分散剂中的自由氨基和/或亚氨基然后与氧化剂或脲反应。
如上所述,分散剂特别用于将颗粒固体分散于有机介质或极性有机介质中。
根据本发明的另一方面,提供了一种含颗粒固体和式1的分散剂的组合物。
根据本发明的另一方面,提供了一种分散体,它含式1的分散剂、颗粒固体和有机介质。
存在于分散体中的固体可以是在所述温度下基本上不溶于有机介质中并且希望以细分形式稳定于其中的任意无机或有机固体材料。
合适的固体的实例有溶剂油墨用颜料;涂料和塑料材料用的颜料、增量剂和填料;染料,例如,分散染料;溶剂染料浴、油墨和其它溶剂应用体系用的光学增亮剂和纺织辅料;油基和转化乳胶钻探泥浆用固体;干洗液中的污垢和固体颗粒;颗粒陶瓷材料;磁性材料和磁性记录介质、阻燃剂例如用于塑料材料中的阻燃剂和用作有机介质中分散体的生物杀虫剂、农用化学品和医药品。
在一个实施方式中,固体是例如在第三版the Colour Index(1971)和随后的修订版及其增刊中在章节标题“Pigments”中所述的任意已知类别的颜料。无机颜料的实例有二氧化钛、氧化锌、普鲁士蓝、硫化镉、铁氧化物、朱红、群青和铬颜料,包括铅、锌、钡、钙的铬酸盐、钼酸盐和混合铬酸盐和硫酸盐及其混合物和改性物,它们可以浅绿色-黄色到红色颜料以名称樱草色、柠檬色、中间色、橙色、猩红色和红色铬商购获得。有机颜料的实例有偶氮、双偶氮、缩合偶氮、硫靛、阴丹酮、异阴丹酮、三苯并芘-5,10-二酮、蒽醌、异二苯并蒽酮、三苯并二噁嗪、喹吖啶酮和酞菁系列,例如,铜酞菁及其核卤代衍生物,以及酸性、碱性和媒染染料的沉淀色料。炭黑,严格地讲是无机物,在其分散性能方面更象有机颜料。在一个实施方式中,有机颜料是酞菁,例如,铜酞菁、单偶氮、双偶氮、阴丹酮、三苯并芘-5,10-二酮、喹吖啶酮和炭黑。
其它适用的固体包括增量剂和填料例如滑石粉、高岭土、二氧化硅、重晶石和白垩;颗粒陶瓷材料例如氧化铝、二氧化硅、氧化锆、二氧化钛、氮化硅、氮化硼、碳化硅、碳化硼、混合氮化硅-氮化铝和金属钛酸盐;颗粒磁性材料例如过渡金属,例如,铁和铬的磁性氧化物,例如γ-Fe2O3、Fe3O4和钴掺杂铁氧化物、氧化钙、铁氧体,例如,钡铁氧体;和金属颗粒,例如,金属铁、镍、钴及其合金;农用化学品例如杀真菌剂flutriafen、多菌灵、百菌清和代森锰锌和阻燃剂例如三水合铝和氢氧化镁。
存在于本发明分散体之中的有机介质在一个实施方式中是极性有机介质或者基本上非极性的芳香烃或者卤代烃。与有机介质有关的术语“极性”是指能够形成中等到强结合的有机液体或者树脂,如Crowley等在Journal of Paint Technology,卷38,1966,269页中的论文“A Three Dimensional Approach to Solubility”所描述的。这类有机介质通常具有5或以上的氢键合数目,如在上述论文中定义的。
适合的极性有机液体的例子是胺、醚(例如,低级烷基醚)、有机酸、酯、酮、二醇、醇和酰胺。这类中等强度氢键合液体的众多特定的例子在Ibert Mellan的“Compatibility and Solubility”(1968Noyes Development Corporation出版)中39-40页表2.14中给出,所有这些液体都在本申请中术语极性有机液体的范围内。
在一个实施方式中,极性有机液体是二烷基酮、链烷羧酸和链烷醇的烷基酯,例如,包含最多(包括)总共6个碳原子的这类液体。有机液体的合适实例包括二烷基和环烷基酮,例如丙酮、甲基乙基酮、二乙基酮、二异丙酮、甲基异丁基酮、二异丁酮、甲基异戊酮、甲基正戊基酮和环己酮;烷基酯例如乙酸甲酯、乙酸乙酯、乙酸异丙酯、乙酸丁酯、甲酸乙酯、丙酸甲酯、甲氧基丙基乙酸酯和丁酸乙酯;二醇和二醇酯和醚,例如乙二醇、2-乙氧基乙醇、3-甲氧基丙基丙醇、3-乙氧基丙基丙醇、乙酸2-丁氧基乙酯、乙酸3-甲氧基丙酯、乙酸3-乙氧基丙酯和乙酸2-乙氧基乙酯;链烷醇例如甲醇、乙醇、正丙醇、异丙醇、正丁醇和异丁醇和二烷基和环醚例如二乙醚和四氢呋喃。
基本上非极性的有机液体,其可以单独或者与上述的极性溶剂混合使用,是芳香烃例如甲苯和二甲苯、脂肪族烃例如己烷、庚烷、辛烷、癸烷、石油蒸馏物例如石油溶剂、矿物油、植物油和卤代脂肪族和芳香族烃例如三氯乙烯、全氯乙烯和氯苯。
作为用于本发明分散体形式介质的适合的极性树脂的例子是成膜性树脂例如适合于制备油墨、涂料的那些和用于各种应用例如涂料和油墨的切片。这类树脂的例子包括聚酰胺,例如VersamidTM和WolfamidTM,和纤维素醚例如乙基纤维素和乙基羟乙基纤维素。涂料树脂的例子包括短油醇酸树脂/蜜胺-甲醛、聚酯/蜜胺-甲醛、热固性丙烯酸类/蜜胺-甲醛、长油醇酸树脂和多重介质树脂例如丙烯酸类和脲/醛。
所述树脂也可以是不饱和聚酯树脂,包括所谓的片材模塑化合物和整体模塑化合物,其可以与增强纤维和填料配合。这类模塑化合物描述于DE3,643,007和PF Bruins题为“Unsaturated PolyesterTechnology”的专题论文,Gordon and Breach Sciencepublis hers,1976,211到238页。
如果需要,所述分散体可以包含其它成分,例如树脂(其中这些还没有构成有机介质)粘结剂、流体化试剂(例如描述于GB-A-1508576和GB-A-2108143中的那些)、抗沉降剂、增塑剂、均化剂和防腐剂。
所述分散体通常包含5到95重量%的固体,精确的量取决于固体的性质和用量取决于固体的性质和固体和有机介质的相对密度。例如,基于分散体的总重量,其中固体是有机材料例如有机颜料的分散体,通常包含15到60重量%的固体,而其中固体是无机材料例如无机颜料、填料或者增量剂的分散体,通常包含40到90重量%的固体。
所述分散体可以通过任何制备分散体的已知常规方法获得。因此,可以任何次序混合所述固体、有机介质和分散剂,然后对混合物进行机械处理,以降低固体的粒子至适当的尺寸,例如通过球磨研磨、珠研磨、卵石研磨或者塑料研磨,直到形成所述分散体。可选择地,可以对所述固体进行单独处理或在与有机介质或者分散剂的混合物中进行处理以降低其粒度,然后加入其它成分,并且搅拌所述混合物以提供所述分散体。
如果所述组合物需要为干燥形式,所述液体介质可以是挥发性的,以便可以容易地通过简单的分离手段例如蒸发从所述颗粒固体除去。在一个实施方式中,分散体包含液体介质。
如果干燥组合物主要由所述分散剂和颗粒固体组成,在一个实施方式中,基于所述颗粒固体的重量,其包含至少0.2%,或者至少0.5%或者至少1.0%的分散剂。在一个实施方式中,干燥组合物包含不高于100重量%或者不高于50重量%或不高于20重量%或不高于10重量%的所述颗粒固体。
如上所述,本发明分散剂尤其适用于制备研磨料,其中颗粒固体在液体介质中在颗粒固体和成膜性树脂粘结剂两者存在下进行研磨。
因此,按照本发明更进一步的方面,提供了研磨料,其包含颗粒固体、分散剂和成膜性树脂。
通常,基于所述研磨料的总重量,所述研磨料包含20到70重量%的颗粒固体。在一个实施方式中,所述颗粒固体占所述研磨料不低于30或不低于50重量%。
实施例
实施例1
研磨基料中树脂的量可以在很大范围内变化,但是通常是不小于研磨基料的连续/液相重量的10%,或不小于20%。在一个实施方式中,树脂的量不大于研磨基料的连续/液相重量的50%或不大于40%。
将硬脂酸(9.2份,32mmol,得自Aldrich)和ε-己内酯(51.1份,448mmol,得自Aldrich)在氮气、120℃下搅拌。然后加入钛酸四丁酯(0.3份)并在200℃下继续搅拌反应16小时。然后将温度降低至120℃并加入聚乙烯亚胺(7.5份,SP 200,MW 10,000,得自NipponShokubai)并在氮气、120℃下将反应物搅拌6小时。冷却至200℃之后,获得一种硬、蜡状固体产物。其是分散剂A。碱当量是1675。
80℃下将分散剂A(56份)溶解在甲苯(57.45份)中得到一澄清液。加入脲(1.45份)并在氮气、120℃下将反应物搅拌18小时。蒸发除去溶剂并在冷却至20℃之后,获得米色固体产物(56份)。其是分散剂1。碱当量是2210。
实施例2
将己酸(10份,86mmol,得自Aldrich)和ε-己内酯(112份,981mmol,得自Aldrich)在氮气、120℃下搅拌。然后加入钛酸四丁酯(0.5份)并在200℃下继续搅拌反应18小时。然后将温度降低至120℃并加入聚乙烯亚胺(12份,SP 050,MW 5,000,得自Nippon Shokubai)并在氮气、120℃下将反应物搅拌8小时。冷却至200℃之后,获得一种硬、蜡状固体产物。其是分散剂B。碱当量是1557。
80℃下将分散剂B(50份)溶解在甲苯(57.45份)中得到一澄清液。加入脲(1.6份)并在氮气、120℃下将反应物搅拌18小时。蒸发除去溶剂并在冷却至20℃之后,获得米色固体产物(56份)。其是分散剂2。碱当量是2730。
实施例3
将蓖麻油酸(300份,得自Fluka)和丁醇锆(1份)在200℃下搅拌直至达到50mgKOH/g的酸值,相应地MW为1120。然后将该混合物的温度降低至120℃并加入聚乙烯亚胺(28.5份,SP 200,MW 10,000,得自Nippon Shokubai)并在氮气、120℃下将反应物搅拌6小时。冷却至室温之后,获得一种金色液体产物。其是分散剂C。碱当量是2136。
80℃下将分散剂C(40份)和脲(1.31份,得自Fisher)在一起于80℃、氮气环境下搅拌18小时。获得一褐色、粘性液体(40份)。其是分散剂3。碱当量是3839。
实施例4
将蓖麻油酸(100份,得自Fluka)、12-羟基硬脂酸(100.67份)和丁醇锆(1份)在200℃下搅拌直到获得35mg KOH/g的酸值,相应地MW是1600。然后,将该混合物的温度降低至120℃并加入聚乙烯亚胺(13.5份,SP 200,MW 10,000,得自Nippon Shokubai)并将这些反应物于氮气、120℃下搅拌6小时。冷却至20℃之后,获得一金色液体产物。其是分散剂D。碱当量是1376。
将分散剂D(40份)和35wt%的过氧化氢水溶液(1.06份,得自Fisher)一起在80℃、氮气环境下搅拌直到该过氧化物基本上反应,用淀粉碘化物试纸证实为阴性结果。获得一褐色粘性液体(40份)。其是分散剂4。碱当量是1845。
实施例5
将月桂酸(10份,49mmol,得自Aldrich)、ε-己内酯(44.7份,392mmol,得自Aldrich)和7-甲基己内酯(25份,196mmol)在氮气、120℃下搅拌。然后加入异丙醇锆(0.45份)并在200℃下搅拌继续反应6小时。然后将温度降低至120℃并加入聚乙烯亚胺(5.5份,SP 200,MW 10,000,得自Nippon Shokubai)并将这些反应物于氮气、120℃下搅拌6小时。冷却至20℃之后,获得淡褐色液体产品。其是分散剂E。碱当量是1407。
将分散剂E(40份)和35wt%的过氧化氢水溶液(1.1份,得自Fisher)一起在80℃、氮气环境下搅拌直到该过氧化物基本上反应,用淀粉碘化物试纸证实为阴性结果。获得一褐色粘性液体(40份)。其是分散剂5。碱当量是1801。
实施例6
将Isocarb 16(7份,27mmol,得自Sasol)、ε-己内酯(27.7份,243mmol,得自Aldrich)和7-甲基己内酯(10.4份,81mmol)在氮气、120℃下搅拌。然后加入丁醇锆(0.3份)并在200℃下搅拌继续反应6小时。然后将温度降低至120℃并加入聚乙烯亚胺(6.4份,SP 030,MW 3,000,得自Nippon Shokubai)并将这些反应物于氮气、120℃下搅拌6小时。冷却至20℃之后,获得淡褐色液体产品。其是分散剂F。碱当量是833。
将分散剂F(40份)和35wt%的过氧化氢水溶液(4.5份,得自Fisher)一起在80℃、氮气环境下搅拌直到该过氧化物基本上反应,用淀粉碘化物试纸证实为阴性结果。获得一褐色粘性液体(41份)。其是分散剂6。碱当量是1228。
实施例7
将Isocarb 16(7份,27mmol,得自Sasol)、ε-己内酯(27.7份,243mmol,得自Aldrich)和7-甲基己内酯(10.4份,81mmol)在氮气、120℃下搅拌。然后加入丁醇锆(0.3份)并在200℃下搅拌继续反应6小时。其是中间体1。
将蓖麻油酸(35份,得自Fluka)、ε-己内酯(18.7份,得自Aldrich)、Isocarb 12(9.4份,得自Sasol)和丁醇锆(0.3份)在200℃下搅拌直到获得30mg KOH/g的酸值,相应地MW是1820。其是中间体2。
将中间体1(18份)和中间体2(6份)在120℃下搅拌并加入聚乙烯亚胺(2份,SP 200,MW 10,000,得自Nippon Shokubai)并将这些反应物于氮气、120℃下搅拌6小时。冷却至20℃之后,获得淡褐色液体产品。其是分散剂G。碱当量是1312。
将分散剂G(24份)和35wt%的过氧化氢水溶液(2.5份,得自Fisher)一起在80℃、氮气环境下搅拌直到该过氧化物基本上反应,用淀粉碘化物试纸证实为阴性结果。获得一褐色粘性液体(41份)。其是分散剂7。碱当量是2217。
实施例8
将月桂酸(5份)、δ-戊内酯(7.5份)和ε-己内酯(34.2份)在氮气、120℃下搅拌。然后加入丁醇锆(0.3份)并在200℃搅拌继续反应8小时。然后将温度降低至120℃并加入聚乙烯亚胺(3.6份,SP 200,MW10,000,得自Nippon Shokubai)并将这些反应物于氮气、120℃下搅拌6小时。在冷却至200℃之后,获得一软、蜡状固体产物。其是分散剂H。碱当量是1710。
在80℃将分散剂H(49份)溶解在甲苯(50.5份)中得到一澄清液。加入脲(1.5份)并将这些反应物于氮气、120℃下搅拌18小时。蒸发除去溶剂并在冷却至20℃之后获得一米色固体产物(56份)。其是分散剂8。碱当量是2872。
实施例9
将月桂酸(10份)、δ-戊内酯(5份)和ε-己内酯(22.8份)在氮气、120℃下搅拌。然后加入丁醇锆(0.3份)并在200℃搅拌继续反应8小时。然后将温度降低至120℃并加入聚乙烯亚胺(5.4份,SP 018,MW1,800,得自Nippon Shokubai)并将这些反应物于氮气、120℃下搅拌6小时。在冷却至200℃之后获得一软、蜡状固体产物。其是分散剂I。碱当量是1128。
将分散剂I(40份)和脲(2份)一起在氮气、120℃下搅拌18小时。获得一琥珀色粘性液体产物(40份)。其是分散剂9。碱当量是1503。
将IsocarbTM 16(25份,97mmol,得自Sasol)和亚硫酰氯(13.9份,117mmol)在甲苯(30ml)中于125℃搅拌8小时,然后在减压下除去溶剂和过量的亚硫酰氯,得到褐色液体IsocarbTM 16酰氯产物(24.5份)。IR显示1794cm-1下酰氯羰基峰。将IsocarbTM 16酰氯(10.7份,38.8mmol)、ε-己内酯(13.3份,116mmol,得自Aldrich)和12-羟基硬脂酸(35份,116mmol)在氮气、150℃下搅拌。然后加入丁醇锆(0.3份)并在185℃下搅拌继续反应24小时。然后将温度降低至120℃,将40份的该混合物和聚乙烯亚胺(4份,SP 075,MW 7,500,得自Nippon Shokubai)在氮气、120℃下搅拌6小时。冷却至20℃之后,获得一褐色粘性液体产物。其是分散剂J。碱当量是1133。
80℃下将分散剂J(33份)溶解在甲苯(50份)中得到一澄清液。加入脲(0.96份)并将这些反应物于氮气、120℃下搅拌18小时。蒸发除去溶剂并在冷却至20℃之后获得一米色固体产物(56份)。其是分散剂10。碱当量是1599。
研磨试验
根据需要,在加温下,将分散剂(0.45份)溶于溶剂(7.55份)中。冷却至25℃之后,加入3mm直径玻璃珠(16份)和红色颜料(2份,Monolite Rubine 3B,得自Avecia)。将该颜料在水平振荡器上振荡研磨16小时。使用任意标度A到E(好到坏)评价得到的分散体的粘性。结果示于下表1,它清楚地描述了与在和脲、分散剂A反应之前的分散剂相比,该脲分散剂,分散剂1,在极性和非极性溶剂中都产生优异的分散体。
表1
Monastral Blue BG的研磨配方和方法
颜料是Monastral Blue BG(得自Heubach,Pigment Blue 15.1),研磨料是30%颜料和颜料重量的12.6%试剂,Solsperse 5000是可以从Noveon Specialty Additives获得的增效剂(流化剂)。与上述相似地评价研磨料。使用Monastral Blue BG获得的结果示于表2。
表2
分散剂 | 甲苯 |
1 | A/B |
2 | A |
3 | A |
4 | B |
5 | B |
6 | B |
7 | A/B |
8 | B |
9 | C |
10 | A |
B | B |
E | B |
F | B/C |
上面提及的每一文献都通过引用加入本文。除了实施例中或其它明确指示之外,本说明书中描述材料量、反应条件、分子量、碳原子数等的所有数量,都应理解为用词语“约”修饰。除非另有说明,本文所述的每一化学成分或组合物应解释为工业级材料,它可以含有异构体、副产物、衍生物、和其它通常理解为存在于工业级中的材料。然而,每一化学成分的存在量(不包括任何溶剂或稀释油)可以是工业材料的常规存在量,除非另有说明。应理解本文所述的上限和下限、范围、和比例限制可以独立组合。类似地,本发明每一要素的范围和量可以与任意其它要素的范围或量一起使用。本文所用的短语“基本上由...组成”可以包括本质上不影响考虑的组合物的基本和新特征的物质。
尽管就其优选实施方式解释了本发明,但是应理解的是在阅读本说明书之后其各种改进对本领域技术人员来说是显而易见的。因此,应理解的是本文公开的本发明意欲包括落入附加权利要求书的范围内的这些改进。
Claims (15)
2、如权利要求1所述的分散剂,其中T是羧酸R-C00H的残基,其中R是任选取代的C1-50烃基。
3、如权利要求2所述的分散剂,其中R是任选取代的烷基,它可以是直链或支链。
4、如权利要求2所述的分散剂,其中R含有一个或多个醚基。
5、如权利要求1所述的分散剂,其中A是羟基-C2-20-亚烯基羧酸或羟基-C1-20-亚烷基羧酸或其内酯的残基。
6、如权利要求5所述的分散剂,其中A是12-羟基硬脂酸或蓖麻油酸的残基。
7、如权利要求5所述的分散剂,其中内酯是ε-己内酯。
8、如权利要求1所述的分散剂,其中m不大于20。
9、如权利要求1所述的分散剂,它包括带有至少两个式(3)链的聚乙烯胺、聚烯丙胺或聚(C2-4-烷撑亚胺):
T-V-(A)m-U-
式(3)
其中,
T、V、A、U和m如权利要求1定义的。
10、如权利要求1所述的分散剂,其中,在式(4)中,X-*-*-X与Y的重量比是20:1-2:1。
12、式1的分散剂的制备方法,其中W是脲残基,该方法包括使不带基团T-V-(A)m-U-的Z中的亚氨基或氨基与脲在100℃-150℃的温度下反应。
13、组合物,包括颗粒固体和权利要求1所述的分散剂。
14、如权利要求13所述的组合物,还包括有机液体。
15、研磨料、涂料或油墨,包括颗粒固体、有机液体、成膜粘合剂树脂和如权利要求1所述的分散剂。
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