JPH0268126A - Nonaqueous dispersion stabilizer of fine powder - Google Patents
Nonaqueous dispersion stabilizer of fine powderInfo
- Publication number
- JPH0268126A JPH0268126A JP63217540A JP21754088A JPH0268126A JP H0268126 A JPH0268126 A JP H0268126A JP 63217540 A JP63217540 A JP 63217540A JP 21754088 A JP21754088 A JP 21754088A JP H0268126 A JPH0268126 A JP H0268126A
- Authority
- JP
- Japan
- Prior art keywords
- fine powder
- compd
- dispersion
- oxide
- dispersion stabilizer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 42
- 239000000843 powder Substances 0.000 title claims abstract description 39
- 239000003381 stabilizer Substances 0.000 title claims abstract description 22
- 229920000768 polyamine Polymers 0.000 claims abstract description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 11
- 229920000570 polyether Polymers 0.000 claims abstract description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000007788 liquid Substances 0.000 abstract description 13
- 229920002873 Polyethylenimine Polymers 0.000 abstract description 6
- 125000002947 alkylene group Chemical group 0.000 abstract description 4
- 150000002924 oxiranes Chemical class 0.000 abstract description 3
- 238000007259 addition reaction Methods 0.000 abstract description 2
- 230000002209 hydrophobic effect Effects 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- -1 polyethylene Polymers 0.000 description 18
- 239000000049 pigment Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000986 disperse dye Substances 0.000 description 3
- 239000002612 dispersion medium Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 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
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003827 glycol group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 239000011163 secondary particle Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- RNMDNPCBIKJCQP-UHFFFAOYSA-N 5-nonyl-7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-ol Chemical compound C(CCCCCCCC)C1=C2C(=C(C=C1)O)O2 RNMDNPCBIKJCQP-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 229920001342 Bakelite® Polymers 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Chemical class 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000012356 Product development Methods 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000010692 aromatic oil Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 239000004637 bakelite Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- BELZJFWUNQWBES-UHFFFAOYSA-N caldopentamine Chemical compound NCCCNCCCNCCCNCCCN BELZJFWUNQWBES-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000006258 conductive agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- 239000012948 isocyanate Chemical class 0.000 description 1
- 150000002513 isocyanates Chemical class 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
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000006247 magnetic powder Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 239000000088 plastic resin Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 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
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000004449 solid propellant Substances 0.000 description 1
- 229950004959 sorbitan oleate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Abstract
Description
本発明は、微粉末の非水系分散安定剤、更に詳しくは不
溶性の微粉末を非水系液体に短時間で分散させると共に
、長期間の分散安定性を与え、ハードケーキを生成しな
い微粉末の非水系分散安定剤に関するものである。The present invention provides a fine powder non-aqueous dispersion stabilizer, more specifically, a fine powder non-aqueous dispersion stabilizer that disperses an insoluble fine powder in a non-aqueous liquid in a short time, provides long-term dispersion stability, and does not produce a hard cake. This invention relates to an aqueous dispersion stabilizer.
微粉末の非水系分散安定剤は種々の産業分野で利用され
ている。例えば、塗料、顔料、印刷インキ分野での顔料
、塗料の分散は重要な基礎技術であり、また分散性を向
上するために分散剤と称される界面活性剤が用いられる
。顔料、樹脂類、溶剤類が多様化する中にあって、顔料
を微粉末化し、溶剤毎に各種の分散剤が用いられている
。
さらに、近年では潤滑剤、金属粉、研磨剤、充填剤、増
量剤、焼結剤、導電剤、燃料固体粒、農薬粉、分散染料
、殺菌剤等の微粉末を非水系液体に分散させた商品の開
発が進んでおり、いずれも分散安定剤が用いられる場合
が多い。Fine powder non-aqueous dispersion stabilizers are used in various industrial fields. For example, dispersion of pigments and paints in the field of paints, pigments, and printing inks is an important basic technology, and surfactants called dispersants are used to improve dispersibility. With the diversification of pigments, resins, and solvents, pigments are made into fine powders and various dispersants are used for each solvent. Furthermore, in recent years, fine powders such as lubricants, metal powders, abrasives, fillers, extenders, sintering agents, conductive agents, solid fuel particles, agricultural chemical powders, disperse dyes, and fungicides have been dispersed in non-aqueous liquids. Product development is progressing, and dispersion stabilizers are often used in all products.
しかしながら、このような従来の微粉末の非水系分散剤
にあっては分散安定性などにいくつかの問題があり、例
えば、長期保存中に微粉末粒子が沈降分離するなど、い
まだ満足すべきものはなかなか見い出されていない、さ
らに、従来の分散剤にあっては分散系を調製した直後は
良好な分散系が得られ、系の粘度を低減できるといった
ような効果が認められる場合もあるが、長期間放置する
と微粉末粒子が沈降し、硬く再分散しにくい沈澱物、即
ちハードケーキをつくることが多い、一般に分散性が良
好なほど、強固なハードケーキを形成しやすい。However, such conventional fine powder non-aqueous dispersants have some problems such as dispersion stability, such as sedimentation and separation of fine powder particles during long-term storage. Furthermore, with conventional dispersants, it is possible to obtain a good dispersion immediately after preparing the dispersion, and in some cases, the effect of reducing the viscosity of the system is recognized, If left for a long period of time, the fine powder particles will settle, often forming a hard precipitate that is difficult to redisperse, that is, a hard cake. Generally, the better the dispersibility, the easier it is to form a strong hard cake.
【発明が解決しようとする：Ｊ！１１】本発明は分散性
が良好でかつ長期安定性に優れた不溶性微粉末の非水系
分散安定剤を提供することを目的としてなされたもので
ある。[Invention tries to solve: J! 11] The object of the present invention is to provide a non-aqueous dispersion stabilizer in the form of an insoluble fine powder which has good dispersibility and excellent long-term stability.
本発明者等は鋭意研究を重ねた結果、上記問題点を解決
できる分散安定剤を見出し１本発明に到達した。すなわ
ち本発明は窒素原子３〜２００個を有するポリアミン化
合物にエチレンオキサイドとブチレンオキサイドを付加
して得られる、好ましくはブチレンオキサイド・が末端
に付加して得られる分子、１１０００〜１００万のポリ
エーテル化合物を必須成分とすることを特徴とする不溶
性微粉末の非水系分散安定剤である。
（手段を構成する要件）
本発明に使用する分散安定剤の出発物質であるポリアミ
ン化合物は、分子内に窒素原子数３〜２００個有するポ
リエチレンイミン、ポリエチレンイミン誘導体、ポリア
ルキレンポリアミン又はポリアルキレンポリアミン誘導
体が挙げられる。
ポリアルキレンポリアミンとは、ジエチレントリアミン
、トリエチレンテトラミン、テトラエチレンペンタミン
、ペンタエチレンへキサミン、ジプロピレントリアミン
、テトラプロピレンペンタアミン又はポリエチレンポリ
アミンの製造工程において得られる蒸留残査物等が挙げ
られる。
またポリエチレンイミン誘導体及びポリアルキレンポリ
アミン誘導体とは、ポリエチレンイミン及びポリアルキ
レンポリアミンから誘導されるすべての化合物を含むも
ので、たとえばアルコール類、ポリオール類、フェノー
ル類、アミン類、ポリアミン類、チオール類、カルボン
酸類、ポリカルボン酸類などの活性水素を１個以上有す
る化合物を開始剤としたエチレンイミンの付加重合体や
、ポリエチレンイミン及びポリアルキレンポリアミンの
活性水素に対してアルデヒド類、ケトン類、アルキルハ
ライド類、アクリルアミド等の活性二重結合を有する化
合物類、イソシアネート類、チオシアネート類、エポキ
シ化合物、エピハロヒドリン類、カルボン酸類、酸無水
物、シアナマイト類、グアニジン類、尿素類などとの反
応生成物が挙げられる。
これらの出発物質は１種又は２種以上を使用することが
でき、通常の方法によりアルキレンオキサイド付加体を
容易に製造することができる。すなわち、出発物質のポ
リアミン化合物をアルカリ触媒下で１００〜１８０℃、
１−１０気圧でフルキレンオキサイドを付加反応するこ
とにより目的物が得られる。
アルキレンオキサイドは疎水基としてのブチレンオキサ
イドをベースに親木基であるエチレンオキサイドが加わ
る事が重要であり、この両者が必須成分である。他に１
０重量％以下の範囲でプロピレンオキサイド、炭素数６
〜２２のα−オレフィンエポキサイド、炭素数８〜２０
の脂肪族アルコール及びアルキルフェノールのグリシジ
ルエーテルの１種又は２種以上を付加しても良いが、こ
のエチレンオキサイドおよびブチレンオキサイド以外の
アルキレンオキサイドは付加した全フルキレンオキサイ
ドの１０重量％以上含有すると、凝集作用が強く働くた
め、分散安定性が損なわれ好ましくない、ブチレンオキ
サイドとエチレンオキサイドの付加モル数はポリアミン
化合物の活性水素１個当り２〜１５０モルで、ブチレン
オキサイド、エチレンオキサイドいずれを先に付加して
もよい、また、ブロック付加、ランダム付加の方法はど
ちらでも良好であるが、エチレンオキサイドを先に付加
し末端にブチレンオキサイドをブロック付加したものが
より好ましい、さらに、エチレンオキサイドとブチレン
オキサイドの重量比は８０／２０〜１０／９０ （ＥＯ
／ＢＯ）であり、好ましくは７０／３０〜２０／８０で
ある。ポリエーテルの平均分子量は１０００〜１００万
、より好ましくは５０００〜８０万である。平均分子量
が１０００未満であると、分散安定性が損なわれる。
さらに前記ポリエーテル化合物の水酸基の一部又は全部
をエステル化したポリエーテル誘導体も有効である。
この場合のポリエーテル誘導体であるエステル化物はア
ジピン酸、フタール醜、マレイン酸、コハク最などのジ
カルボン酸あるいはこれらの酸無水物やポリカルボン醜
との反応物であり、また、硫酸、モノクロルスルホン酸
、無水硫酸、無水リン酸等を使用して通常公知の方法で
ポリエーテルをエステル化した硫酸エステル化物、リン
酸エステル化物が挙げられる。このエステル化物は水酸
化ナトリウム、水酸化カリウム、水酸化カルシウム、水
酸化アンモニウム等のアルカリ性物質又はアルカノール
アミン、ポリエチレンポリアミン。
アルキルアミン等のアミ５ン類との中和物であってもよ
い。
また、本発明のポリエーテルで、窒素原子の一部又は全
部をカチオン化、または有！ａ厳か無機酸にて中和した
化合物を使用することが出来る。カチオン化に用いるカ
チオン化試薬としては塩化メチル、塩化エチル、臭化メ
チル、ヨウ化エチル等のアルキルハライド類やジメチル
１ｉ＆酸、ジエチル硫酸、エピクロルヒドリンベンジル
クロライド等を挙げることが出来る。さらに、有機酸と
しては酢酸、シュウ醜、クエン酸、乳酸、リンゴ酸等が
、また無機酸としては塩酸、硝酸、硫酸、リン酸等がい
ずれも使用出来るが、非水系液体の分散でより安定性の
好ましい有機酸塩を使用するのが望ましい。
前記した本発明の分散安定剤は分散液全体に対して０．
０１〜１５重酸％、好ましくはｏ、ｉ〜ｌＯ重量％の割
合で使用する。０．０１重量％より使用量が少ないと効
果が小さく、また１５重量％をこえても効果の改善が顕
著でなく経済的に不利である。
本発明の分散安定剤は無機及び有機のいずれの微粉末に
対しても有効であり、とくに限定しないが、例えば、無
機微粉末としてはカオリン、ケイ酸アルミニウム、クレ
ー、タルク、マイカ、アスベスト粉、ケイ酸カルシウム
、セリサイト、ベントナイト、群青、ケイ酸マグネシウ
ム等のケイ酸塩、炭酸カルシウム、炭酸マグネシウム、
炭酸バリウム、ドロマイト等の炭酸塩、硫酸カルシウム
、！酸バリウム、硫酸アルミニウム等の硫酸塩、ジルコ
ニア、マグネシア、アルミナ、三酸化アンチモン、酸化
チタン、ホワイトカーボン、けいそう土、酸化鉄、酸化
亜鉛等の金属酸化物、水酸化アルミニウム、水酸化鉄等
の水酸化物、そのほか紺青、炭化ケイ素、窒化ケイ素、
窒化ホウ素、チタン酸バリウム、カーボンブラック、黒
鉛、二硫化モリブデン、フッ化カーボン、焼結セラミッ
クス粉末、炭素繊維粉末、イオウ粉末、磁性粉、鉄粉、
アルミ粉、銅粉、ニッケル粉、銀粉、金粉等がまた有機
微粉末としては、不溶性アゾ顔料、アゾ系分散染料、ア
ントラキノン系分散染料、スレン染料、フタロシアニン
系顔料、レーキ顔料、ペリレン顔料、ジオキサジン顔料
、キナクリントン顔料等の着色材粉末、ポリエチレン樹
脂、ポリスチレン樹脂、ウレタン樹脂、ポリアミド樹脂
、アクリロニトリル樹脂、テフロン樹脂、メラミンイソ
シアヌレート樹脂、ベークライト樹１指等のプラスチッ
ク樹脂粉末、その他、固体パラフィン、石炭、農薬、殺
菌剤、酸化防止剤、紫外線吸収剤、難燃剤等の微粉末が
挙げられる。
これら微粉末の平均粒子径は１００ミクロン以下、一般
には０．Ｏ１〜５０ミクロン程度を使用するのがよい、
また分散系における微粉末の濃度は分散系が得られる濃
度であればいずれでもよいが、一般には１〜５０重量％
で使用する場合が多い。
また、上記固体微粉末を分散させる非水系液体の分散媒
はへキサン、ヘプタン、シクロヘキサン、ミネラルター
ペン、流動パラフィン、マシン油、スピンドル油等の脂
肪族炭化水素油、ベンゼン、トルエン、キシレンなどの
芳香族炭化水素油、灯油、軽油、重油などの燃料油、エ
タノール、インプロパツール、ブタノール、オクタツー
ル等の脂肪族アルコール、酢酸エチル、ジオクチルフタ
レート、大豆油、ヤシ油、牛脂等のエステル油、パーク
ロルエチレン、トリクロルエタンなどのハロゲン化炭化
水素油、さらにメチルイソブチルケトン、メチルエチル
ケトン、アセトン、塗料用液状樹脂やエチレングリコー
ル、プロピレングリコール、グリセリン、ポリエチレン
グリコール等の液状多価アルコール等であり、これらの
単独または２種以上の混合物が使用できる。
本発明の分散安定剤の使用に際しては、いずれの分散機
を使用してもよく１例えば、ボールミル、サンドミル、
ビスコミル、三木ロール、アトライター等を使用する。
さらに、分散安定剤の添加は前記分散機で、二次粒子を
粉砕する工程の前又は、後に加えればよいが、一般には
工程前に添加する方が分散が良好となり二次粒子の粉砕
が早まるので好ましい。
尚、本発明の分散安定、剤は単独で用いてもよく、他の
非水系分散剤、たとえば、ポリオキシエチレンノニルフ
ェノールエーテル、ソルビタンオレイン酸エステル、レ
シチン、ポリオキシエチレンオクチルエーテルホスフェ
ート、ドデシルベンゼンスルホン酸カルシウム塩、石油
スルホン酸カルシウム塩、脂肪酸金属石鹸等と併用して
もよい。さらに５重量％以下の少量の水を分散系に添加
してもよい。As a result of extensive research, the present inventors have discovered a dispersion stabilizer that can solve the above problems and have arrived at the present invention. That is, the present invention is a molecule obtained by adding ethylene oxide and butylene oxide to a polyamine compound having 3 to 200 nitrogen atoms, preferably adding butylene oxide to the terminal, and a polyether compound having 11,000 to 1,000,000 atoms. This is an insoluble fine powder non-aqueous dispersion stabilizer characterized by containing as an essential component. (Requirements constituting the means) The polyamine compound that is the starting material of the dispersion stabilizer used in the present invention is polyethyleneimine, a polyethyleneimine derivative, a polyalkylene polyamine, or a polyalkylene polyamine derivative having 3 to 200 nitrogen atoms in the molecule. can be mentioned. Examples of polyalkylene polyamines include diethylene triamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, dipropylene triamine, tetrapropylene pentamine, and distillation residues obtained in the process of producing polyethylene polyamine. Furthermore, polyethyleneimine derivatives and polyalkylenepolyamine derivatives include all compounds derived from polyethyleneimine and polyalkylenepolyamines, such as alcohols, polyols, phenols, amines, polyamines, thiols, and carboxyl compounds. Addition polymers of ethyleneimine using a compound having one or more active hydrogens such as acids and polycarboxylic acids as an initiator, and active hydrogens of polyethyleneimine and polyalkylenepolyamines such as aldehydes, ketones, alkyl halides, Examples include reaction products with compounds having active double bonds such as acrylamide, isocyanates, thiocyanates, epoxy compounds, epihalohydrins, carboxylic acids, acid anhydrides, cyanamites, guanidines, ureas, and the like. One or more of these starting materials can be used, and the alkylene oxide adduct can be easily produced by a conventional method. That is, the polyamine compound as a starting material was heated at 100 to 180°C under an alkali catalyst.
The desired product is obtained by addition reaction with fullylene oxide at 1-10 atm. It is important that alkylene oxide has ethylene oxide as a parent group added to the base of butylene oxide as a hydrophobic group, and both of these are essential components. 1 other
Propylene oxide in the range of 0% by weight or less, carbon number 6
~22 α-olefin epoxide, carbon number 8-20
One or more types of aliphatic alcohols and glycidyl ethers of alkylphenols may be added, but if alkylene oxides other than ethylene oxide and butylene oxide are contained in an amount of 10% by weight or more of the total added fullylene oxide, agglomeration may occur. The number of moles of butylene oxide and ethylene oxide added is 2 to 150 moles per active hydrogen of the polyamine compound, and it is not preferable to add butylene oxide or ethylene oxide first because the action is strong and dispersion stability is impaired. Also, both block addition and random addition methods are good, but it is more preferable to add ethylene oxide first and block add butylene oxide to the terminal.Furthermore, the weight of ethylene oxide and butylene oxide The ratio is 80/20 to 10/90 (EO
/BO), preferably 70/30 to 20/80. The average molecular weight of the polyether is 1,000 to 1,000,000, more preferably 5,000 to 800,000. If the average molecular weight is less than 1000, dispersion stability will be impaired. Furthermore, polyether derivatives obtained by esterifying some or all of the hydroxyl groups of the polyether compounds are also effective. In this case, the esterified product, which is a polyether derivative, is a dicarboxylic acid such as adipic acid, phthalate, maleic acid, or succinic acid, or a reaction product with these acid anhydrides or polycarboxylic acid, and also sulfuric acid, monochlorosulfonic acid, etc. Examples include sulfuric acid esterified products and phosphoric acid esterified products in which polyether is esterified by a commonly known method using sulfuric anhydride, phosphoric acid anhydride, and the like. This esterified product is an alkaline substance such as sodium hydroxide, potassium hydroxide, calcium hydroxide, ammonium hydroxide, or alkanolamine, polyethylene polyamine. It may also be a neutralized product with amines such as alkyl amines. In addition, in the polyether of the present invention, some or all of the nitrogen atoms may be cationized or present! (a) Compounds neutralized with an inorganic acid can be used. Examples of cationizing reagents used for cationization include alkyl halides such as methyl chloride, ethyl chloride, methyl bromide, and ethyl iodide, dimethyl 1i&acid, diethyl sulfate, and epichlorohydrin benzyl chloride. Furthermore, as organic acids, acetic acid, citric acid, lactic acid, malic acid, etc. can be used, and as inorganic acids, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, etc. can be used, but they are more stable when dispersed in non-aqueous liquids. It is desirable to use organic acid salts of preferred nature. The above-mentioned dispersion stabilizer of the present invention has a content of 0.0% with respect to the entire dispersion.
It is used in a proportion of 0.01 to 15% by weight, preferably o, i to 10% by weight. If the amount used is less than 0.01% by weight, the effect will be small, and if it exceeds 15% by weight, the improvement in the effect will not be significant, which is economically disadvantageous. The dispersion stabilizer of the present invention is effective for both inorganic and organic fine powders, and examples of inorganic fine powders include, but are not limited to, kaolin, aluminum silicate, clay, talc, mica, asbestos powder, Silicates such as calcium silicate, sericite, bentonite, ultramarine, magnesium silicate, calcium carbonate, magnesium carbonate,
Barium carbonate, carbonates such as dolomite, calcium sulfate,! Sulfates such as barium acid, aluminum sulfate, zirconia, magnesia, alumina, antimony trioxide, titanium oxide, white carbon, diatomaceous earth, metal oxides such as iron oxide, zinc oxide, aluminum hydroxide, iron hydroxide, etc. Hydroxide, other dark blue, silicon carbide, silicon nitride,
Boron nitride, barium titanate, carbon black, graphite, molybdenum disulfide, carbon fluoride, sintered ceramic powder, carbon fiber powder, sulfur powder, magnetic powder, iron powder,
Aluminum powder, copper powder, nickel powder, silver powder, gold powder, etc. Organic fine powders include insoluble azo pigments, azo disperse dyes, anthraquinone disperse dyes, threne dyes, phthalocyanine pigments, lake pigments, perylene pigments, and dioxazine pigments. , colorant powders such as cinchlin pigments, polyethylene resins, polystyrene resins, urethane resins, polyamide resins, acrylonitrile resins, Teflon resins, melamine isocyanurate resins, plastic resin powders such as Bakelite wood 1 finger, etc., solid paraffin, coal, Examples include fine powders of agricultural chemicals, fungicides, antioxidants, ultraviolet absorbers, flame retardants, and the like. The average particle diameter of these fine powders is 100 microns or less, generally 0. It is best to use about 01 to 50 microns.
The concentration of fine powder in the dispersion system may be any concentration as long as a dispersion system can be obtained, but generally it is 1 to 50% by weight.
It is often used in In addition, the non-aqueous liquid dispersion medium for dispersing the above-mentioned solid fine powder is an aliphatic hydrocarbon oil such as hexane, heptane, cyclohexane, mineral turpentine, liquid paraffin, machine oil, spindle oil, etc., or aromatic oil such as benzene, toluene, xylene, etc. Group hydrocarbon oils, fuel oils such as kerosene, light oil, and heavy oil; aliphatic alcohols such as ethanol, impropatol, butanol, and octatool; ester oils such as ethyl acetate, dioctyl phthalate, soybean oil, coconut oil, and beef tallow; These include halogenated hydrocarbon oils such as chloroethylene and trichloroethane, as well as methyl isobutyl ketone, methyl ethyl ketone, acetone, liquid resins for paints, and liquid polyhydric alcohols such as ethylene glycol, propylene glycol, glycerin, and polyethylene glycol. Alternatively, a mixture of two or more types can be used. When using the dispersion stabilizer of the present invention, any dispersing machine may be used. For example, a ball mill, a sand mill,
Use Visco Mill, Miki Roll, Attritor, etc. Furthermore, the dispersion stabilizer can be added before or after the process of pulverizing the secondary particles using the dispersion machine, but generally, adding it before the process will result in better dispersion and faster pulverization of the secondary particles. Therefore, it is preferable. The dispersion stabilizing agent of the present invention may be used alone, and other non-aqueous dispersants such as polyoxyethylene nonylphenol ether, sorbitan oleate, lecithin, polyoxyethylene octyl ether phosphate, dodecylbenzenesulfonic acid It may be used in combination with calcium salts, petroleum sulfonic acid calcium salts, fatty acid metal soaps, etc. Additionally, small amounts of water, up to 5% by weight, may be added to the dispersion.
本発明の分散安定剤が今までに類を見ない多種類の微粉
末物質と、広範囲の各種非水系液体の分散媒に対して優
れた分散性と安定性の効果が得られるのは、高分子琶で
かさぼりの大きい特殊な分子構造であり、さらに必須成
分である親水性の強いポリエチレングリコール鎖と、親
油性の強いポリブチレングリコール鎖が、微粉末粒子に
対しバランス良く効果的に強く吸着する為、微粉末粒子
に対する保護コロイド作用が高く、−成粒子への分散性
と再凝集を防止する力（作用）がより強力であるためと
考えられる。The reason why the dispersion stabilizer of the present invention has an unprecedented effect of excellent dispersibility and stability for a wide variety of fine powder substances and a wide variety of non-aqueous liquid dispersion media is due to its high quality. It has a special molecular structure with a large bulk, and the essential components, highly hydrophilic polyethylene glycol chains and highly lipophilic polybutylene glycol chains, effectively and strongly adsorb to fine powder particles in a well-balanced manner. This is thought to be due to the fact that the protective colloid has a strong effect on the fine powder particles, and has a stronger dispersibility into particles and a stronger force (effect) to prevent reagglomeration.
以下、本発明を実施例によって具体的に説明するが１本
発明はそれらによって何等限定されるものでない。
ここで、用いた各種分散安定剤を第１表に示した。さら
に、下記の試験により分散安定性能を評価した。この試
験結果を第２表と第３表に示した。
〈分散安定性試験〉
所定量の分散安定剤を含む非水系液体の分散媒１Ｋｇに
所定量の不溶性微粉末を加え、固体分１０〜４０重量％
とする。この混合液をビーズミルで３０分間粉砕混合し
分散液を得る０次にこの分散液を１０００ｍＭ目盛付シ
リンダーに入れ３０℃の恒温室に静置し、１日後と１０
日後の分散状態（評価＝１）及び１００日後に発生した
沈殿物の硬さと再分散性の容易さ（評価−２）を評価し
た。
（評価−１）
分散状態は微粒子が沈降せずに分散しているか否かを次
の項目の記号で評価する。
■、すべての粉末が液中に分散し、まったく底部に沈澱
が発生していない。
０、はとんどの粉末が液中に分散しているが、わずかに
底部に沈澱が発生する。
Δ、半分程度の粉末が底部に沈澱する。
Ｘ、はとんどの粉末が底部に沈澱する。
（評価−２）
沈澱物の硬さと再分散性の容易さは次の項目の記号で評
価する。
Ｏ０液の攪拌で、容易に沈澱物は分散する。
０、沈澱が柔く、ガラス棒攪拌で容易に再分散できる。
Δ、沈澱が硬い為、ガラス棒攪拌を強くしないと再分散
しない。
Ｘ、沈澱が非常に硬く再分散出来ない。
（以下余白）EXAMPLES The present invention will be specifically explained below with reference to Examples, but the present invention is not limited by these in any way. Here, the various dispersion stabilizers used are shown in Table 1. Furthermore, the dispersion stability performance was evaluated by the following test. The test results are shown in Tables 2 and 3. <Dispersion stability test> A predetermined amount of insoluble fine powder is added to 1 kg of a non-aqueous liquid dispersion medium containing a predetermined amount of a dispersion stabilizer, and the solid content is 10 to 40% by weight.
shall be. This mixture was pulverized and mixed in a bead mill for 30 minutes to obtain a dispersion.Next, this dispersion was placed in a cylinder with a 1000mM scale and left to stand in a constant temperature room at 30°C, and after 1 day and 10
The dispersion state after 100 days (evaluation = 1) and the hardness of the precipitate generated after 100 days and ease of redispersibility (evaluation -2) were evaluated. (Evaluation-1) The dispersion state is evaluated using the symbols in the following items to determine whether or not the fine particles are dispersed without settling. ■ All the powder was dispersed in the liquid, and no sediment was formed at the bottom. 0: Most of the powder is dispersed in the liquid, but a slight amount of precipitate occurs at the bottom. Δ, about half of the powder settles to the bottom. X, most of the powder settles to the bottom. (Evaluation-2) The hardness of the precipitate and the ease of redispersibility are evaluated using the following symbols. The precipitate is easily dispersed by stirring the O0 solution. 0. The precipitate is soft and can be easily redispersed by stirring with a glass rod. Δ: Because the precipitate is hard, it will not be redispersed unless the glass rod is strongly stirred. X: The precipitate was very hard and could not be redispersed. (Margin below)
本発明の分散剤は、疎水性と親水性のエポキサイドをバ
ランスよく効果的に構成する為、各種の非水系液体にお
いて、種類の異なる微粉末を短時間で分散でき、さらに
長期間の経時安定性に優れる分散液を得ることができる
。したがって、非水系の微粉末分散技術の進歩に対し、
広く寄与しうるものである。
特許出願人 第一工業製薬株式会社Since the dispersant of the present invention effectively comprises hydrophobic and hydrophilic epoxides in a well-balanced manner, it can disperse different types of fine powders in various non-aqueous liquids in a short time, and also has long-term stability. A dispersion liquid with excellent properties can be obtained. Therefore, with the progress of non-aqueous fine powder dispersion technology,
It can make a wide contribution. Patent applicant Daiichi Kogyo Seiyaku Co., Ltd.
Claims (1)
エチレンオキサイドとブチレンオキサイドを付加して得
られる分子量１０００〜１００万のポリエーテル化合物
を必須成分とすることを特徴とする不溶性微粉末の非水
系分散安定剤。 ２、ポリエーテル化合物がブチレンオキサイドを末端に
有する構造であることを特徴とする特許請求の範囲第１
項記載の不溶性微粉末の非水系分散安定剤。[Claims] 1. An insoluble product characterized by having as an essential component a polyether compound having a molecular weight of 1,000 to 1,000,000, obtained by adding ethylene oxide and butylene oxide to a polyamine compound having 3 to 200 nitrogen atoms. Fine powder non-aqueous dispersion stabilizer. 2. Claim 1, characterized in that the polyether compound has a structure having butylene oxide at the end.
A non-aqueous dispersion stabilizer of an insoluble fine powder as described in .
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63217540A JPH0268126A (en) | 1988-08-31 | 1988-08-31 | Nonaqueous dispersion stabilizer of fine powder |
| US07/398,208 US5034508A (en) | 1988-08-31 | 1989-08-24 | Dispersant for nonaqueous systems |
| DE68914368T DE68914368T2 (en) | 1988-08-31 | 1989-08-30 | Dispersant for non-aqueous systems. |
| EP89116024A EP0359034B1 (en) | 1988-08-31 | 1989-08-30 | Dispersant for nonaqueous systems |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63217540A JPH0268126A (en) | 1988-08-31 | 1988-08-31 | Nonaqueous dispersion stabilizer of fine powder |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0268126A true JPH0268126A (en) | 1990-03-07 |
Family
ID=16705856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63217540A Pending JPH0268126A (en) | 1988-08-31 | 1988-08-31 | Nonaqueous dispersion stabilizer of fine powder |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0268126A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996013555A1 (en) * | 1994-11-01 | 1996-05-09 | Daikin Industries, Ltd. | Fluoropolymer coating composition and coated article |
| JP2000185226A (en) * | 1998-12-22 | 2000-07-04 | Nof Corp | In-oil dispersing/stabilizing agent of organic or inorganic powder |
| JP2011500951A (en) * | 2007-11-09 | 2011-01-06 | ザ プロクター アンド ギャンブル カンパニー | Cleaning composition having an amphiphilic water-soluble polyalkyleneimine having an inner polyethylene oxide block and an outer polypropylene oxide block |
| KR20140090938A (en) | 2013-01-09 | 2014-07-18 | 니치유 가부시키가이샤 | Nonaqueous dispersant and nonaqueous dispersion composition |
| CN115397888A (en) * | 2020-05-29 | 2022-11-25 | 巴斯夫欧洲公司 | Amphoteric modified oligopropyleneimine ethoxylates for improving the detergency of laundry detergents |
| CN115698132A (en) * | 2020-06-17 | 2023-02-03 | 巴斯夫欧洲公司 | Amphiphilic alkoxylated polyethylene/propylene imine copolymers for use in multi-effect detergent formulations |
-
1988
- 1988-08-31 JP JP63217540A patent/JPH0268126A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996013555A1 (en) * | 1994-11-01 | 1996-05-09 | Daikin Industries, Ltd. | Fluoropolymer coating composition and coated article |
| US6124045A (en) * | 1994-11-01 | 2000-09-26 | Daikin Industries, Ltd. | Fluoropolymer coating composition and coated article |
| JP2000185226A (en) * | 1998-12-22 | 2000-07-04 | Nof Corp | In-oil dispersing/stabilizing agent of organic or inorganic powder |
| JP2011500951A (en) * | 2007-11-09 | 2011-01-06 | ザ プロクター アンド ギャンブル カンパニー | Cleaning composition having an amphiphilic water-soluble polyalkyleneimine having an inner polyethylene oxide block and an outer polypropylene oxide block |
| KR20140090938A (en) | 2013-01-09 | 2014-07-18 | 니치유 가부시키가이샤 | Nonaqueous dispersant and nonaqueous dispersion composition |
| CN115397888A (en) * | 2020-05-29 | 2022-11-25 | 巴斯夫欧洲公司 | Amphoteric modified oligopropyleneimine ethoxylates for improving the detergency of laundry detergents |
| CN115698132A (en) * | 2020-06-17 | 2023-02-03 | 巴斯夫欧洲公司 | Amphiphilic alkoxylated polyethylene/propylene imine copolymers for use in multi-effect detergent formulations |
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