CN101198663B - 分散剂及其组合物 - Google Patents
分散剂及其组合物 Download PDFInfo
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- CN101198663B CN101198663B CN2006800214767A CN200680021476A CN101198663B CN 101198663 B CN101198663 B CN 101198663B CN 2006800214767 A CN2006800214767 A CN 2006800214767A CN 200680021476 A CN200680021476 A CN 200680021476A CN 101198663 B CN101198663 B CN 101198663B
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- alkyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 239000002270 dispersing agent Substances 0.000 title description 4
- 239000007787 solid Substances 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000003973 paint Substances 0.000 claims abstract description 15
- -1 N-oxide compound Chemical class 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000007788 liquid Substances 0.000 claims description 32
- 239000000049 pigment Substances 0.000 claims description 16
- 238000007639 printing Methods 0.000 claims description 16
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 11
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000004033 plastic Substances 0.000 claims description 8
- 229920003023 plastic Polymers 0.000 claims description 8
- 229920002367 Polyisobutene Polymers 0.000 claims description 7
- 150000002500 ions Chemical class 0.000 claims description 7
- 230000002209 hydrophobic effect Effects 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 150000008053 sultones Chemical class 0.000 claims description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 76
- 239000000976 ink Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 13
- 229920000768 polyamine Polymers 0.000 description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 229960002317 succinimide Drugs 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000000975 dye Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 6
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000003863 ammonium salts Chemical group 0.000 description 5
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 4
- 239000002904 solvent Substances 0.000 description 4
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000005263 alkylenediamine group Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 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 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- KFYRJJBUHYILSO-YFKPBYRVSA-N (2s)-2-amino-3-dimethylarsanylsulfanyl-3-methylbutanoic acid Chemical compound C[As](C)SC(C)(C)[C@@H](N)C(O)=O KFYRJJBUHYILSO-YFKPBYRVSA-N 0.000 description 2
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229920002368 Glissopal ® Polymers 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 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
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 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
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
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- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 235000019239 indanthrene blue RS Nutrition 0.000 description 2
- 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 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
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- 239000011707 mineral Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
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- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical class NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
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- 239000005995 Aluminium silicate Substances 0.000 description 1
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- 229910052582 BN Inorganic materials 0.000 description 1
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- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
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- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
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- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
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Abstract
本发明提供组合物,包含:(i)颗粒状固体;(ii)有机介质;和(iii)烃基取代的丙烯酸酯化剂。本发明进一步提供所述组合物在各种应用,包括油漆、油墨或研磨基料中的用途。
Description
发明领域
本发明涉及包含分散剂的盐、颗粒状固体和有机介质的新型组合物。本发明进一步涉及所述分散剂在介质,如油墨、研磨基料、塑料和油漆中的用途。
发明背景
许多制剂如油墨、油漆、研磨基料和塑料材料需要有效的分散剂用以将颗粒状固体均匀地分布在有机介质中。有机介质可以为极性有机介质至非极性有机介质。含末端碱性基如聚(低级亚烷基)亚胺链的分散剂是为人熟知的并且通常通过使聚亚胺与含末端酸基的聚酯链反应来制备,该反应获得酰胺和其盐形式的混合物。然而,这些分散剂中的许多具有有限的对粘度和稳定性性能的表现,它们当引入到印刷油墨或油漆中时产生具有差流动特性的油墨和油漆。因此,仍需要能够对流动特性、粘度和稳定性性能中至少一项提供可接受性能的分散剂。
美国专利号5,721,358公开了一种酞菁铜的制备方法,该方法使用衍生自非盐化琥珀酰亚胺分散剂的分散剂。该琥珀酰亚胺分散剂衍生自亚烷基胺和聚异丁烯琥珀酸酐。
美国专利申请2003/0213410公开了一种聚合物改性的颜料,其包含:具有至少一个羧基或其盐的聚合物和至少一种偶联剂。该聚合物包括已经与酰化剂如乙酸或琥珀酸酐起反应的多胺的衍生物。
GB1,373,660公开了可通过使多羟基羧酸与二胺,尤其是亚烷基二胺和其盐反应获得的聚酯胺分散剂。
美国专利号5,000,792公开了可通过使2份多羟基羧酸与1份二亚烷基三胺反应获得的聚酯胺分散剂。
因此,具有一种具有可接受粘度和稳定性性能的分散剂将是有利的,该分散剂当引入到印刷油墨或油漆中时产生具有可接受流动特性的油墨和油漆。
发明概述
已经发现,某些分散剂显示出优异的在有机介质,尤其是非极性有机介质的范围中分散颗粒状固体的能力。另外,所述分散剂中的一些是新颖的。
因此,根据本发明,提供一种组合物,其包含:(i)颗粒状固体;(ii)有机介质;和(iii)烃基取代的酰化剂的盐。
在一个实施方案中,本发明提供分散剂,其包含烃基取代的酰化剂的烃基取代的碳酸盐。
在一个实施方案中,本发明提供一种组合物,其包含(i)颗粒状固体,(ii)有机介质;和(iii)通式(1)的化合物及其盐:
B-CO-Z-R 通式(1)
其中
B包括疏水性烷基链,该疏水性烷基链通常基于数均分子量为300-5000的聚异丁烯,该疏水性烷基链连同该-CO-基团是聚异丁烯琥珀酸酐的残基;
Z是二价桥连基,其经由氧或氮原子与该羰基连接并且可以由以下通式一般性表示:
-N(T)-A-或-O-A-;
其中
T是氢,或C1-18烃基,或由A表示的基团或聚异丁烯琥珀酸酐的残基;
A是含2-6个碳原子的亚烷基或羟基亚烷基;
R是由以下通式表示的季铵基团:
-N+(T2)(T3)(T4)W-
其中
T2、T3和T4各自独立地是氢,任选取代的烷基烷芳基或环烷基,或R是N-氧化物官能化的季铵基团;和
W-是无色或有色阴离子。
发明详述
本发明提供如上面所限定的组合物。
在一个实施方案中,烃基取代的酰化剂的盐包含琥珀酰亚胺官能团。通常,该琥珀酰亚胺官能团衍生自胺或其反应性等同物。
在一个实施方案中,烃基取代的酰化剂的盐可以是碱金属如锂、钾或钠的盐。或者,该盐可以形成有氨、胺、铵阳离子或季铵阳离子。在一个实施方案中,烃基取代的酰化剂的盐是铵盐。在一个实施方案中,烃基取代的酰化剂的盐包括琥珀酰亚胺烃基取代的酰化剂的铵盐和/或季铵盐。
在一个实施方案中,琥珀酰亚胺烃基取代的酰化剂的铵盐和/或季铵盐是分散剂。
烃基取代的酰化剂
烃基取代的酰化剂通常具有在数个实施方案中数均分子量为300-5000,450-4000,500-3000或550-2500的烃基基团。在数个实施方案中,烃基基团具有大约550,或大约750,或950-1000,或大约1600或大约2300的数均分子量。
在一个实施方案中,烃基基团包括聚合物。适合的聚合物的实例包括聚烯烃或聚氧化烯。
在一个实施方案中,聚合物可以衍生自至少一种烯烃或烯烃的结合物。
在数个实施方案中,聚合物衍生自含2-8个碳原子或3-6个碳原子的烯烃。适合的烯烃的实例包括丙烯、异丁烯、戊烯或己烯。通常,聚合物衍生自异丁烯以形成聚异丁烯。
在一个实施方案中,聚合物具有末端C=C双键基团,即亚乙烯基基团。通常,存在的亚乙烯基基团的量不是重要的,因为琥珀酸酯化聚合物(尤其是琥珀酸酯化聚异丁烯)可以通过氯路线或由无氯路线制备。
亚乙烯基基团的含量通常为该聚合物分子的至少2wt%,或至少40%,或至少50%,或至少60%,或至少70%。通常,亚乙烯基基团的含量为大约75%,大约80%或大约85%。
所述聚合物可以按商品名称Glissopal1000或Glissopal2300(可从BASF商购),TPC555、TPC575或TPC595(可从Texas Petroleum Chemicals商购)商业上获得。
酰化剂
本发明的酰化剂可以是具有一个或多个酸官能团的化合物,如羧酸或其酸酐。酰化剂的实例包括α,β-不饱和一元羧酸或多元羧酸,它们的酸酐酯或衍生物。酰化剂的实例包括(甲基)丙烯酸、(甲基)丙烯酸甲酯、马来酸或马来酸酐、富马酸、衣康酸或衣康酸酐,或它们的混合物。
胺
胺是本领域中已知的胺并且包括环状(芳族和/或非芳族)胺如取代的单胺、多胺或其混合物。本领域技术人员将了解能够形成季铵盐的适合的胺化合物。
在一个实施方案中,胺具有至少一个反应性N-H键(氮-氢键)。胺可以包含一个或多个伯和仲胺官能团。或者,胺可以包含一个或多个伯和叔胺官能团。任选地,胺还可以进一步被其它官能团,如羟基取代。
在一个实施方案中,取代的单胺具有1-22个碳原子并且进一步取代有能够与所述烃基取代的酰化剂反应的基团。通常,单胺将包含仲或叔胺官能团。
季铵阳离子可以是季铵阳离子或苄烷铵阳离子如吡啶阳离子。在一个实施方案中,季铵阳离子包含一个或两个含6-20个碳原子的烷基。
适合的胺的实例包括N,N-二甲基-氨基丙胺、N,N-二乙基-氨基丙胺、N,N-二甲基-氨基乙胺亚乙基二胺、1,2-亚丙基二胺、1,3-亚丙基二胺、异构化的亚丁基二胺、戊烷二胺、己烷二胺、庚烷二胺、二亚乙基三胺、二亚丙基三胺、二亚丁基三胺、三亚乙基四胺、四亚乙基五胺、五亚乙基六胺、六亚甲基四胺和双(六亚甲基)三胺、二氨基苯、二氨基吡啶或它们的混合物。
其它适合的季铵阳离子的实例包括四乙基铵、N-十八烷基-N,N,N-三甲基铵;N,N-二(十二烷基)-N,N-二甲基铵、N-苄基-N,N,N-三甲基铵和N-苄基-N-十八烷基-N,N-二甲基铵阳离子。
在一个实施方案中,多胺包括亚烷基二胺或取代的亚烷基二胺,如亚乙基二胺和N-甲基亚丙基二胺,聚烯烃多胺,例如,四亚乙基五胺和多亚乙基多胺底部流出物,含一个或多个羟基的链烷醇胺如2-(2-氨基乙氨基)乙醇,氨基烷基取代的杂环化合物如1-(3-氨基丙基)咪唑和4-(3-氨基丙基)吗啉,1-(2-氨乙基)哌啶,3,3-二氨基-N-甲基二丙胺,3′,3-氨基双(N,N-二甲基丙胺),多胺与多羟基化合物的缩合物如美国专利号5,653,152中描述的多亚乙基多胺与三(羟甲基)氨基甲烷的缩合物,或它们的混合物。在一个实施方案中,胺是四亚乙基五胺。
其它有用类型的多胺混合物是通过将上述多胺混合物气提以留下通常称作“多胺底部流出物”的残余物获得的那些。一般而言,亚烷基多胺底部流出物可能表现在具有少于两种,通常少于1%(wt)沸点小于大约200℃的材料。从Dow Chemical Company ofFreeport,Texas获得的名称为“E-100”的此种亚乙基多胺底部流出物的典型样品具有1.0168的在15.6℃下的比重、33.15wt%的含氮量和121厘沱的在40℃下的粘度。此种样品的气相色谱法分析包含大约0.93%“轻馏分”(非常可能是DETA)、0.72%TETA、21.74%四亚乙基戊胺和76.61%五亚乙基六胺和更高级(按重量)。这些亚烷基多胺底部流出物包括环状缩合产物如哌嗪和二亚乙基三胺或三亚乙基四胺的更高级类似物。
在一个实施方案中,铵盐和/或季铵盐具有阴离子型季化抗衡离子,包括卤离子、氢氧根、磺酸根、烷基硫酸根、磺酸内酯、磷酸根、C1-12烷基磷酸根、二C1-12烷基磷酸根、硼酸根、C1-12烷基硼酸根、亚硝酸根、硝酸根、碳酸根、碳酸氢根、烷羧酸根、O,O-二C1-12烷基二硫代磷酸根和它们的混合物。
在一个实施方案中,所述季化抗衡离子可以衍生自二烷基硫酸酯如硫酸二甲酯,N-氧化物,磺酸内酯如丙烷和丁烷磺酸内酯,烷基或芳烷基卤化物如甲基和乙基氯化物、溴化物或碘化物或苄基氯化物,和烃基(或烷基)取代的碳酸酯如碳酸二甲酯或二乙酯。
在一个实施方案中,所述分散剂包含烃基取代的酰化剂的烃基取代的碳酸盐。
在其它实施方案中,季铵抗衡离子可以衍生自盐酸、硫酸、乙酸、丙酸、甲酸、甲烷磺酸、苯磺酸、对甲苯磺酸、苯甲酸或含至少一个磺酸或羧酸基的有机染料,尤其是含至少一个磺酸或羧酸基偶氮、蒽醌或酞菁染料例如1971年出版的颜色指数第三版中描述的那些。
烃基取代的酰化剂的适合的盐的实例包括:
(a)美国专利号4,253,980和/或美国专利号3,778,371中描述和要求的分散剂,即吡啶盐的聚异丁烯琥珀酰亚胺酯内酯;
(b)美国专利号4,326,973和/或美国专利号4,338,206中描述和要求的分散剂,即吡啶盐的聚异丁烯琥珀酰亚胺;和
(c)美国专利号5,254,138中描述和要求的分散剂,即聚烷基琥珀酸酐与聚氨基羟烷基季铵盐的反应产物。
(a)、(b)和(c)中的烃基取代的酰化剂的铵盐和/或季铵盐的制备方法还在每个专利的实施例中进行了公开。
琥珀酰亚胺的适合的季铵盐的其它实例包括碘化聚异丁烯基(335)-N,N,N-三甲基-丙-1,3-二胺琥珀酰亚胺季铵、碘化聚异丁烯基(335)-N-甲基-N-(3-氨基丙基)吗啉基琥珀酰亚胺季铵、碘化聚异丁烯基(1200)-N,N,N-三甲基丙-1,3-二氨基琥珀酰亚胺季铵、碘化聚异丁烯基(850)-N,N,N-三甲基乙-1,2-二氨基琥珀酰亚胺季铵、溴化聚丙烯基(700)-N,N,N-三乙基-丙-1,3-二氨基琥珀酰亚胺季铵、碘化聚异丁烯基(335)-N-甲基-N-(3-氨基丙基)哌嗪基琥珀酰亚胺季铵和氯化聚丙烯基(800)-N-甲基-N-(2-氨乙基)哌嗪基琥珀酰亚胺季铵。碘季铵盐的制备方法在美国专利号4,171,959中进行了描述。
在一个实施方案中,上面通式(1)是所述分散剂。从通式(1),由A表示的基团的实例包括亚乙基、亚丙基、四亚甲基、六亚甲基和2-羟基三亚甲基。
从通式(1),由T表示的基团的实例包括甲基、乙基、正丙基、正丁基、己基、辛基和十八烷基。
从通式(1),由T2、T3和T4表示的基团的实例包括烷基如甲基、乙基、正丙基、正丁基、己基、辛基和十八烷基,羟基低级烷基如2-羟乙基,和环己基。
从通式(1),与胺基形成盐或含有阴离子W-的酸的实例可以是任何无机酸或无色或有色有机酸,如盐酸、硫酸、硫酸二甲酯、乙酸、丙酸、甲酸、甲烷磺酸、苯磺酸、对甲苯磺酸、苯甲酸或含至少一个磺酸或羧酸基的有机染料,尤其是含至少一个磺酸或羧酸基的偶氮、蒽醌或酞菁染料,例如1971年出版的颜色指数第三版本中描述的那些。
存在于组合物中的颗粒状固体可以是任何基本上不溶于有机介质的无机或有机固体材料。在一个实施方案中,所述颗粒状固体是颜料。
适合的固体的实例是用于溶剂油墨的颜料;用于油漆和塑料材料的颜料、增量剂和填料;分散染料;用于溶剂染浴、油墨和其它溶剂应用体系的荧光增白剂和织物助剂;用于油基和反相-乳液钻孔泥的固体;干洗液中的尘土和固体颗粒;颗粒状陶瓷材料;磁性材料和磁记录介质;用于复合材料的纤维如玻璃,钢,碳和硼,和在有机介质中用作分散体的杀生物剂、农用化学品和药物。
在一个实施方案中,所述固体是来自任何公认类别的颜料的有机颜料,所述公认类别的颜料例如在颜色指数(1971)的第三版以及随后的修订版和对其的增补版中在段头“颜料”下进行了描述。有机颜料的实例是选自偶氮、二偶氮、缩合偶氮、硫靛、靛蒽醌、异靛蒽醌、蒽嵌蒽醌、蒽醌、异二苯并蒽酮、三苯二恶嗪、喹吖啶酮和酞菁系列,尤其是铜酞菁及其核卤化衍生物,以及酸的色淀、碱性和酸性媒介染料。炭黑虽然严格来说是无机的,但是其分散性能方面的表现更像有机颜料。在一个实施方案中,有机颜料是酞菁尤其是铜酞菁,单偶氮,二偶氮,靛蒽醌,二苯并吡二酮,喹吖啶酮和炭黑。
无机固体包括:增量剂和填料如滑石、高岭土、二氧化硅、重晶石和白垩;颗粒状陶瓷材料如氧化铝、二氧化硅、氧化锆、氧化钛、氮化硅、氮化硼、碳化硅、碳化硼、混合氮化硅-铝和金属钛酸盐;颗粒状磁性材料如过渡金属尤其是铁和铬的磁性氧化物,例如γ-Fe2O3、Fe3O4,和钴掺杂的氧化铁、氧化钙、铁酸盐尤其是铁酸钡;和金属颗粒,尤其是金属铁、镍、钴、铜和它们的合金。
其它有用的固体材料包括农用化学品如杀真菌剂、flutriafen、多菌灵、百菌清和代森锰。
在一个实施方案中,存在于本发明组合物中的有机介质是塑料材料,在另一个实施方案中,是有机液体。有机液体可以是非极性或极性的有机液体。
可以用作极性有机液体的有机液体的实例是成膜树脂,如适合于制备油墨、油漆和用于各种应用如油漆和油墨的屑片的成膜树脂。此类树脂的实例包括聚酰胺如VersamidTM和WolfamidTM,和纤维素醚如乙基纤维素和乙基羟乙基纤维素,硝化纤维素和乙酸丁酸纤维素树脂,包括它们的混合物。油漆树脂的实例包括短油醇酸树脂/蜜胺-甲醛或长油醇酸树脂。
在一个实施方案中,非极性有机液体是含脂族基、芳族基或其混合物的化合物。非极性有机液体包括未卤化芳族烃(例如,甲苯和二甲苯)、卤化芳族烃(例如,氯苯、二氯苯、氯甲苯)、未卤化脂族烃(例如,含6个或更多碳原子的线性和支化脂族烃,都是完全饱和和部分饱和的)、卤化脂族烃(例如,二氯甲烷、四氯化碳、氯仿、三氯乙烷)和天然非极性有机物(例如,植物油、向日葵油、亚麻子油、萜烯和甘油酯)。
在一个实施方案中,基于总有机液体,该有机液体包含至少0.1wt%,或1wt%或更多极性有机液体。在一个实施方案中,有机液体不含水。
塑料材料可以热固性树脂或热塑性树脂。在本发明中有用的热固性树脂包括当加热、催化或经历UV辐射时发生化学反应并变得相对不熔的树脂。热固性树脂中的典型反应包括不饱和双键的氧化,涉及环氧基/胺、环氧基/羰基、环氧基/羟基、聚异氰酸酯/羟基、氨基树脂/羟基结构部分的反应,聚丙烯酸酯的自由基反应,环氧树脂和乙烯基醚的阳离子聚合,硅醇的缩合。
在一个实施方案中,热塑性树脂包括聚烯烃、聚酯、聚酰胺、聚碳酸酯、聚氨酯、聚苯乙烯系树脂、聚(甲基)丙烯酸酯、纤维素和纤维素衍生物。所述组合物可以按许多方法制备但是典型的方法是熔融混合和干固体共混。
如果需要的话,组合物可以包含其它成分,例如,树脂(当这些还没有构成有机介质时)、粘结剂、流化剂、抗沉降剂、增塑剂、表面活性剂、消泡剂、流变性改进剂、流平剂、光泽改进剂和防腐剂。
组合物通常包含1-95wt%颗粒状固体,其中精确的量取决于固体的性质并且该量取决于固体的性质和固体的相对密度和极性有机液体。例如,基于组合物的总重量,在一个实施方案中,其中固体是有机材料,如有机颜料的组合物包含15-60wt%所述固体,而在一个实施方案中,其中固体是无机材料,如无机颜料、填料或增量剂的组合物包含40-90wt%所述固体
组合物可以通过任何已知用于制备分散体的常规方法来制备。因此,可以按任何次序将固体、有机介质和分散剂混合,然后让该混合物经受机械处理以将固体的颗粒减小到合适的尺寸,例如通过球磨、珠磨、石磨或塑料研磨,直到形成分散体。或者,可以将固体独立地或以有机介质或分散剂的混合物形式进行处理以减小其颗粒尺寸,然后添加其它成分并搅拌该混合物以提供组合物。
本发明的组合物尤其适合于液体分散体。在一个实施方案中,此种分散体组合物包含:
a)0.5-30份颗粒状固体;
b)0.5-30份通式(1)的化合物和/或烃基取代的酰化剂的盐;和
c)40-99份有机液体;
其中所有份数按重量计并且数量(a)+(b)+(c)=100。
在一个实施方案中,组分a)包含0.5-30份颜料并且此类分散体作为(液体)油墨、油漆和研磨基料是有用的。
如果需要包含颗粒状固体和呈干燥形成的通式(1)的分散剂和/或烃基取代的酰化剂的盐的组合物,则有机液体通常是挥发性的,使得可以通过简单的分离手段如蒸发容易地将它从颗粒状固体中除去。在一个实施方案中,组合物包含有机液体。
如果干燥组合物主要由通式(1)的分散剂和/或烃基取代的酰化剂的盐和颗粒状固体构成,则基于所述颗粒状固体的重量,所述组合物通常包含至少0.2%,至少0.5%或至少1.0%通式(1)的分散剂和/或烃基取代的酰化剂的盐。在一个实施方案中,基于颗粒状固体的重量,干燥组合物包含不大于100wt%,不大于50wt%,不大于20wt%,或不大于10wt%通式(1)的分散剂和/或烃基取代的酰化剂的盐。
如上文中所公开的那样,本发明的组合物适合于制备研磨基料,其中在通式(1)的化合物和/或烃基取代的酰化剂的盐存在下在有机液体中研磨颗粒状固体。
因此,根据本发明的又一个方面,提供包含颗粒状固体、有机液体和通式(1)的化合物和/或烃基取代的酰化剂的盐的研磨基料。
通常,基于研磨基料的总重量,所述研磨基料包含20-70wt%颗粒状固体。在一个实施方案中,颗粒状固体不少于研磨基料的10wt%或不少于20wt%。此类研磨基料可以任选地包含在研磨之前或之后添加的粘结剂。
粘结剂是当使有机液体挥发时能够束缚该组合物的聚合物材料。
研磨基料中的分散剂的量取决于颗粒状固体的量但是通常为研磨基料的0.5-5wt%。
由本发明的组合物制成的分散体和研磨基料尤其适合用于涂料和油漆,尤其是高固含量油漆;油墨,尤其是苯胺印刷、凹版印刷和丝网印刷油墨,包括用于无接触印刷的油墨,尤其是在按需供墨(Drop-on-Demand)印刷机的情况下,其中通常通过热或压电装置将油墨从孔口喷出;无水陶瓷加工,尤其是带涂、刮刀-叶片、挤出和注射模塑型加工;复合材料、化妆品、粘合剂和塑料材料。
将通过以下实施例进一步说明本发明,其中对数量的所有引用以重量份为单位,除非表示与此相反。
实施例
中间体1:用3-二甲基氨基丙胺合成琥珀酰亚胺
在缓慢的氮气流下在100℃下搅拌数均分子量为950-1000(和平均1.3个马来酸酐/聚异丁烯链)的聚异丁烯琥珀酸酐(203.7g),然后缓慢地逐滴添加3-二甲基氨基丙胺(还称为DMAPA)(31.22g),并在100℃下搅拌该混合物3小时。然后在185℃下在氮气气氛下搅拌该混合物3小时,在这一阶段除去过量的DMAPA。获得了褐色粘性液体(216g)。产物的基料当量测量为1093mg。这是中间体1。
中间体2-14
通过与中间体1相同的方法制备中间体2-14,不同在于聚异丁烯琥珀酸酐的特征如下:
中间体 | 基于PIBSA的聚异丁烯的数均分子量 | PIBSA的制备方法 | PIBSA与马来酸酐的比例 |
2 | 550 | DA | 1∶1.2 |
3 | 1000 | DA | 1∶1.6 |
4 | 1550 | DA | 1∶1.3 |
5 | 1000 | DA | 1∶1.3 |
6 | 1000 | CL | 1∶1.6 |
7 | 1550 | DA | 1∶2.24 |
8 | 2300 | DA | 1∶1.2 |
9 | 2000 | CL | 1∶1.6 |
10 | 2000 | CL | 1∶1.7 |
11 | 2000 | CL | 1∶1.9 |
12 | 1100 | DA | 1∶1.2 |
13 | 1400 | DA | 1∶1.2 |
14 | 1600 | DA | 1∶1.2 |
脚注:
通过直接烷基化方法或“烯”反应制备DA PIBSA。该“烯”反应在Maleic Anhydride,147-148页中进行了概括,由B.C.Trivedi和B.C.Culbertson所编并由Plenum Press在1982年出版。
CL限定通过美国专利6,440,905或6,165,235或3,172,892或4,234,435中描述的Diels Alder方法制备的PIBSA。
中间体15-21
按与中间体1相同的方法制备中间体15-21,不同在于下面指出的差异:
中间体 | 基于PIBSA的聚异丁烯的数均分子量 | PIBSA的制备方法 | 胺 |
15 | 1100 | DA | 3,3’-亚氨基双(二丙胺) |
16 | 1400 | DA | 3,3’-亚氨基双(二丙胺) |
17 | 1600 | DA | 3,3’-亚氨基双(二丙胺) |
18 | 1100 | DA | N,N,N’-三甲基亚乙基二胺 |
19 | 1400 | DA | N,N,N’-三甲基亚乙基二胺 |
20 | 1600 | DA | N,N,N’-三甲基亚乙基二胺 |
21 | 1000 | DA1∶1.3 | 四亚乙基五胺 |
分散剂1
在缓慢的氮气流下在甲苯(110.96g)中在90℃下搅拌中间体1(100g)15分钟,然后添加硫酸二甲酯(10.96g)。然后在90℃下再搅拌所得的混合物4小时而获得褐色液体(220g)。这是分散剂1。
分散剂2-11
通过与为分散剂1描述的相同方法制备分散剂2-11,不同在于分别使用中间体2-11。
对比实施例1是在没有分散剂的情况下制备的研磨基料。
分散剂12
将中间体1(200g,1当量)加入500ml凸缘烧瓶。
搅拌内容物并加热到90℃。在35分钟内逐滴添加苄基氯(13.5g,0.11mol,0.95当量)并搅拌该混合物70小时。所得的产物是褐色粘性液体,产量为204g(96%)。
分散剂13
将中间体1(200g,1当量)、碳酸二甲基酯(19.91g,0.22mol,2当量)和甲醇(35.56g,1.11mol,10当量)加入600ml高压釜。用氮气吹扫该容器三次并且将内容物加热到140℃在145psi下保持20小时。然后冷却内容物并通过真空蒸馏除去过量的碳酸二甲基酯和甲醇。所得的产物是褐色粘性液体,产量为246g(97%)。
分散剂14
将中间体1(10g,1当量)和甲苯(11.02g)加入50ml烧瓶。搅拌内容物并加热到90℃。在35分钟内逐滴添加1,3-丙烷磺酸内酯(1.02g,0.0083mol,0.95当量)并搅拌该混合物1小时。所得的产物是淡黄色的液体,产量为22g(96%)。
分散剂15-24
通过与为分散剂1描述的相同方法制备分散剂15-24,不同在于分别使用中间体12-21。
分散剂25
通过在容器中预先混合516.5g按与中间体1类似的方式制备的产物与192.7g甲醇、27.4g乙酸和109.8g氧化苯乙烯制备分散剂25。在70℃下将容器的内容物回流4小时。使用Dean Stark设备将产物加热到100℃以蒸馏甲醇,接着除去过量的氧化苯乙烯。将所得的产物冷却到环境温度。
研磨基料的制备
使用分散剂1-24和对比实施例1制备一系列紫红色研磨基料。通过将分散剂1-11(0.38g)溶解在6.47g甲苯的溶剂混合物中制备研磨基料。添加玻璃珠(3mm,17份)和Monastral Blue BG(得自Heubach,颜料蓝,15.1份)、0.15g Solsperse5000(流化剂)并在水平摇动器上将该混合物摇动16小时。然后使用A-E(好-差)的任意等级评价所得的分散体的流动性。分散剂2-11获得的研磨级别在下表2中示出。对比实施例1具有研磨级别E。
表2
实施例 | 甲苯 | 实施例 | 甲苯 |
2 | C | 14 | B |
3 | B | 15 | A/B |
4 | B | 16 | A/B |
5 | B | 17 | A/B |
6 | C | 18 | B/C |
7 | B | 19 | B |
8 | A/B | 20 | B/C |
9 | C/D | 21 | C |
10 | C | 22 | B/C |
11 | C | 23 | B |
12 | A/B | 24 | C |
13 | B | 对照物 | E |
在此所使用的术语“烃基取代基”或“烃基基团”用于其普通意义,这是本领域技术人员熟知的。具体来说,它是指这样的基团,即其具有直接连接到分子其余部分的碳原子并具有基本上是烃的性质。烃基基团的实例包括:
(i)烃取代基,即,脂族(例如烷基或链烯基),脂环族(例如环烷基、环链烯基)取代基,和芳族-、脂族-、以及脂环族-取代的芳族取代基,以及环状取代基,其中该环经由该分子的另一部份来完成(例如两个取代基一起形成环);
(ii)取代的烃取代基,即,含有本发明上下文中不改变取代基烃主导地位的非烃基团的取代基(例如卤(尤其是氯和氟)、羟基、烷氧基、巯基、烷基巯基、硝基、亚硝基、和硫氧基);
(iii)杂取代基,即,在本发明上下文中仍具有突出烃性质的除了碳之外还含有不由碳原子组成的环或链的取代基。杂原子包括硫、氧、氮,并包括诸如吡啶基、呋喃基、噻嗯基和咪唑啉基的取代基。总的来说,对于烃基基团中的每十个碳原子存在至多两个,或至多一个非烃取代基;通常,在烃基基团中存在一个非烃取代基。
上面涉及的每篇文献在此引入作为参考。除了在实施例中,或当另有明确说明时,这一描述中规定材料数量、反应条件、分子量、碳原子数等的所有数值应理解由词语“大约”修饰。除非另有说明,本文涉及的每种化学物质或组合物应该解释为是商品级材料,它们可以包含异构体、副产物、衍生物和其它通常认为将以商品级存在的那些材料。然而,在不算任何溶剂或稀释油的情况下给出每种化学成分的量,所述溶剂或稀释油可以通常存在于该商业材料中,除非另有说明。应该理解的是,本文给出的任何上限和下限数量、范围和比例可以独立地结合。类似地,本发明每种要素的范围和数量可以与任何其它要素的范围或数量一起使用。
虽然仅在上面描述了本发明的少数实施方案,但是应该理解的是,在不脱离本发明精神和范围的情况下可以作出许多修改。所有这些修改应认为包括在本发明中,本发明仅由以下权利要求限制。
Claims (5)
1.组合物,包含:(i)颗粒状固体,其中颗粒状固体是颜料;(ii)有机介质,其中有机介质是有机液体或塑料材料;和(iii)通式(1)的化合物及其盐:
B-CO-Z-R 通式(1)
其中
B包括疏水性烷基链,该疏水性烷基链基于数均分子量为300-5000的聚异丁烯,该疏水性烷基链连同该-CO-基团是聚异丁烯琥珀酸酐的残基;
Z是二价桥连基,其经由氧或氮原子与该羰基连接并且由以下通式表示:
-N(T)-A-或-O-A-;
其中
T是氢,或C1-18烃基,或由A表示的基团或聚异丁烯琥珀酸酐的残基;
A是含2-6个碳原子的亚烷基或羟基亚烷基;
R是由以下通式表示的季铵基团:
-N+(T2)(T3)(T4)W-
其中
T2、T3和T4各自独立地是氢,任选取代的烷基烷芳基或环烷基,或R是N-氧化物官能化的季铵基团;和
W-是无色或有色阴离子。
2.权利要求1的组合物,其中所述季铵基团阴离子型季化抗衡离子选自卤离子、氢氧根、磺酸根、烷基硫酸根、磺酸内酯、磷酸根、C1-12烷基磷酸根、二C1-12烷基磷酸根、硼酸根、C1-12烷基硼酸根、亚硝酸根、硝酸根、碳酸根、碳酸氢根、烷羧酸根、O,O-二C1-12烷基二硫代磷酸根和它们的混合物。
3.根据权利要求1的组合物,其中所述有机液体包含至少0.1wt%极性有机液体,基于总有机液体。
4.含有权利要求1的组合物的油漆或油墨。
5.含有权利要求1的组合物的研磨基料。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US69115605P | 2005-06-16 | 2005-06-16 | |
US60/691,156 | 2005-06-16 | ||
PCT/US2006/022926 WO2006138269A2 (en) | 2005-06-16 | 2006-06-13 | Dispersants and compositions thereof |
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CN101198663A CN101198663A (zh) | 2008-06-11 |
CN101198663B true CN101198663B (zh) | 2011-01-19 |
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CN2006800214767A Expired - Fee Related CN101198663B (zh) | 2005-06-16 | 2006-06-13 | 分散剂及其组合物 |
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US (1) | US7683120B2 (zh) |
EP (1) | EP1896546B1 (zh) |
JP (1) | JP5164835B2 (zh) |
CN (1) | CN101198663B (zh) |
AT (1) | ATE477306T1 (zh) |
DE (1) | DE602006016125D1 (zh) |
ES (1) | ES2347686T3 (zh) |
TW (1) | TW200704711A (zh) |
WO (1) | WO2006138269A2 (zh) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101431899B (zh) * | 2006-03-15 | 2012-11-28 | 胡茨曼石油化学公司 | 用作农用分散剂的聚醚胺的梳状聚合物衍生物 |
WO2008024618A1 (en) * | 2006-08-22 | 2008-02-28 | Lubrizol Limited | Novel dispersants |
US20080113890A1 (en) * | 2006-11-09 | 2008-05-15 | The Lubrizol Corporation | Quaternary Ammonium Salt of a Polyalkene-Substituted Amine Compound |
US20080182927A1 (en) * | 2007-01-31 | 2008-07-31 | Air Products And Chemicals, Inc. | Polyisobutenyl containing dispersions and uses thereof |
US8460404B2 (en) | 2008-05-15 | 2013-06-11 | The Lubrizol Corporation | Quaternary salts for use as surfactants in dispersions |
DK2514807T4 (da) | 2009-05-15 | 2021-01-11 | Lubrizol Corp | Kvaternære ammoniumamidsalte |
SG177347A1 (en) | 2009-06-23 | 2012-02-28 | Rhodia Operations | Synergistic detergent and active metal compound combination |
JP5324013B2 (ja) | 2010-05-20 | 2013-10-23 | ルブリゾル アドバンスド マテリアルズ, インコーポレイテッド | 分散性組成物 |
US9017915B2 (en) | 2010-07-07 | 2015-04-28 | Hewlett-Packard Development Company, L.P. | Electrophotographic ink |
WO2012154515A1 (en) | 2011-05-06 | 2012-11-15 | Lubrizol Advanced Materials, Inc. | Polyester quaternary salt and compositions thereof |
KR102446080B1 (ko) * | 2012-10-23 | 2022-09-22 | 더루우브리졸코오포레이션 | 저분자량 불이익이 없는 디젤 청정제 |
CN103012023B (zh) * | 2012-12-14 | 2015-07-01 | 道毅新力(上海)环保科技有限公司 | 一种工业炸药用乳化剂及其制备方法 |
NL2012115C2 (en) * | 2014-01-21 | 2015-07-22 | Xeikon Ip Bv | Liquid toner dispersion and use thereof. |
KR101571520B1 (ko) | 2014-10-10 | 2015-11-24 | 한국화학연구원 | 폴리이소부테닐 숙신산-폴리아민 분산제 및 이를 포함하는 잉크 조성물 |
WO2016126408A1 (en) * | 2015-02-06 | 2016-08-11 | The Procter & Gamble Company | Amino modified hydrocarbons |
TW201840635A (zh) * | 2017-01-26 | 2018-11-16 | 美商盧伯利索先進材料有限公司 | 具有改良化學及熱安定性之含有一或二個四級胺錨定基的聚合分散劑 |
KR20210113613A (ko) | 2018-12-10 | 2021-09-16 | 솔레니스 테크놀러지스 케이맨, 엘.피. | 역상 유화 중합 공정에 사용하기 위한 안정화제 |
EP3927776A1 (en) | 2019-02-22 | 2021-12-29 | Byk-Chemie GmbH | Aqueous dispersant composition |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4171959A (en) * | 1977-12-14 | 1979-10-23 | Texaco Inc. | Fuel composition containing quaternary ammonium salts of succinimides |
WO2001014433A1 (en) * | 1999-08-20 | 2001-03-01 | The Lubrizol Corporation | Metal containing dispersant polymers from condensation of polymers containing acidic group with overbased compositions containing reactive nucleophilic group |
WO2003029309A2 (de) * | 2001-09-27 | 2003-04-10 | Basf Aktiengesellschaft | Hydrophile emulgatoren auf basis von polyisobutylen |
WO2004065430A1 (en) * | 2003-01-21 | 2004-08-05 | The Lubrizol Corporation | Low color polyisobutylene succinic anhydride-derived emulsifiers |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL255194A (zh) * | 1959-08-24 | |||
US3749695A (en) * | 1971-08-30 | 1973-07-31 | Chevron Res | Lubricating oil additives |
BE793279A (fr) | 1971-12-30 | 1973-06-22 | Ici Ltd | Agents dispersants |
US4253980A (en) * | 1979-06-28 | 1981-03-03 | Texaco Inc. | Quaternary ammonium salt of ester-lactone and hydrocarbon oil containing same |
US4326973A (en) * | 1981-01-13 | 1982-04-27 | Texaco Inc. | Quaternary ammonium succinimide salt composition and lubricating oil containing same |
US7576155B2 (en) * | 2002-12-18 | 2009-08-18 | Bridgestone Corporation | Method for clay exfoliation, compositions therefore, and modified rubber containing same |
DE602005023088D1 (de) * | 2004-03-26 | 2010-10-07 | Toyota Motor Co Ltd | Dispergiermittel oder ein die Beschichtungsfähigkeit verbesserndes Mittel |
US20090018040A1 (en) * | 2005-02-03 | 2009-01-15 | The Lubrizol Corporation | Dispersants from Condensed Polyamines |
-
2006
- 2006-06-13 AT AT06772993T patent/ATE477306T1/de not_active IP Right Cessation
- 2006-06-13 US US11/917,235 patent/US7683120B2/en not_active Expired - Fee Related
- 2006-06-13 ES ES06772993T patent/ES2347686T3/es active Active
- 2006-06-13 EP EP06772993A patent/EP1896546B1/en not_active Not-in-force
- 2006-06-13 JP JP2008517002A patent/JP5164835B2/ja not_active Expired - Fee Related
- 2006-06-13 CN CN2006800214767A patent/CN101198663B/zh not_active Expired - Fee Related
- 2006-06-13 DE DE602006016125T patent/DE602006016125D1/de active Active
- 2006-06-13 WO PCT/US2006/022926 patent/WO2006138269A2/en active Application Filing
- 2006-06-14 TW TW095121122A patent/TW200704711A/zh unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4171959A (en) * | 1977-12-14 | 1979-10-23 | Texaco Inc. | Fuel composition containing quaternary ammonium salts of succinimides |
WO2001014433A1 (en) * | 1999-08-20 | 2001-03-01 | The Lubrizol Corporation | Metal containing dispersant polymers from condensation of polymers containing acidic group with overbased compositions containing reactive nucleophilic group |
US6403725B1 (en) * | 1999-08-20 | 2002-06-11 | The Lubrizol Corporation | Metal containing dispersant polymers from condensation of polymers containing acidic group with overbased compositions containing reactive nucleophilic group |
WO2003029309A2 (de) * | 2001-09-27 | 2003-04-10 | Basf Aktiengesellschaft | Hydrophile emulgatoren auf basis von polyisobutylen |
WO2004065430A1 (en) * | 2003-01-21 | 2004-08-05 | The Lubrizol Corporation | Low color polyisobutylene succinic anhydride-derived emulsifiers |
Also Published As
Publication number | Publication date |
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JP5164835B2 (ja) | 2013-03-21 |
DE602006016125D1 (de) | 2010-09-23 |
EP1896546A2 (en) | 2008-03-12 |
JP2008544044A (ja) | 2008-12-04 |
WO2006138269A3 (en) | 2007-05-24 |
CN101198663A (zh) | 2008-06-11 |
WO2006138269A2 (en) | 2006-12-28 |
ATE477306T1 (de) | 2010-08-15 |
US20080207826A1 (en) | 2008-08-28 |
ES2347686T3 (es) | 2010-11-03 |
US7683120B2 (en) | 2010-03-23 |
TW200704711A (en) | 2007-02-01 |
EP1896546B1 (en) | 2010-08-11 |
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