EP0541631A1 - N-substituierte pyricliniumborate - Google Patents
N-substituierte pyricliniumborateInfo
- Publication number
- EP0541631A1 EP0541631A1 EP19910913878 EP91913878A EP0541631A1 EP 0541631 A1 EP0541631 A1 EP 0541631A1 EP 19910913878 EP19910913878 EP 19910913878 EP 91913878 A EP91913878 A EP 91913878A EP 0541631 A1 EP0541631 A1 EP 0541631A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- tetraphenylborate
- carbon atoms
- salt
- charge
- toner
- 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.)
- Withdrawn
Links
- -1 N-substituted pyridinium salts Chemical class 0.000 claims abstract description 89
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 30
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 239000000460 chlorine Chemical group 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Chemical group 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 229910052740 iodine Chemical group 0.000 claims abstract description 3
- 239000011630 iodine Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 239000004067 bulking agent Substances 0.000 abstract 1
- 239000002245 particle Substances 0.000 description 61
- 239000003795 chemical substances by application Substances 0.000 description 38
- 229920000642 polymer Polymers 0.000 description 24
- 238000000034 method Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
- 238000002411 thermogravimetry Methods 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000003086 colorant Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 6
- 229910000859 α-Fe Inorganic materials 0.000 description 6
- 239000011162 core material Substances 0.000 description 5
- 230000005291 magnetic effect Effects 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- YNJQKNVVBBIPBA-UHFFFAOYSA-M tetrabutylazanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCC[N+](CCCC)(CCCC)CCCC YNJQKNVVBBIPBA-UHFFFAOYSA-M 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000005686 electrostatic field Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- 229920005792 styrene-acrylic resin Polymers 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- HJNAJKBRYDFICV-UHFFFAOYSA-M 1-tetradecylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCCCCCCCC[N+]1=CC=CC=C1 HJNAJKBRYDFICV-UHFFFAOYSA-M 0.000 description 2
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920006370 Kynar Polymers 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- YCUVUDODLRLVIC-UHFFFAOYSA-N Sudan black B Chemical compound C1=CC(=C23)NC(C)(C)NC2=CC=CC3=C1N=NC(C1=CC=CC=C11)=CC=C1N=NC1=CC=CC=C1 YCUVUDODLRLVIC-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- VAABWZGRNKNTTQ-UHFFFAOYSA-M benzyl-dimethyl-octadecylazanium;2-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 VAABWZGRNKNTTQ-UHFFFAOYSA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007771 core particle Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 1
- KVBQNFMTEUEOCD-UHFFFAOYSA-M 1-butylpyridin-1-ium;bromide Chemical compound [Br-].CCCC[N+]1=CC=CC=C1 KVBQNFMTEUEOCD-UHFFFAOYSA-M 0.000 description 1
- PNXWPUCNFMVBBK-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+]1=CC=CC=C1 PNXWPUCNFMVBBK-UHFFFAOYSA-M 0.000 description 1
- ABFDKXBSQCTIKH-UHFFFAOYSA-M 1-ethylpyridin-1-ium;bromide Chemical compound [Br-].CC[N+]1=CC=CC=C1 ABFDKXBSQCTIKH-UHFFFAOYSA-M 0.000 description 1
- AMKUSFIBHAUBIJ-UHFFFAOYSA-N 1-hexylpyridin-1-ium Chemical compound CCCCCC[N+]1=CC=CC=C1 AMKUSFIBHAUBIJ-UHFFFAOYSA-N 0.000 description 1
- SZRSEFNUSHACPD-UHFFFAOYSA-M 1-hexylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCC[N+]1=CC=CC=C1 SZRSEFNUSHACPD-UHFFFAOYSA-M 0.000 description 1
- JDASKPRUFDKACZ-UHFFFAOYSA-M 1-octadecylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 JDASKPRUFDKACZ-UHFFFAOYSA-M 0.000 description 1
- JOEPKDCJDKHSFJ-UHFFFAOYSA-M 1-pentylpyridin-1-ium;bromide Chemical compound [Br-].CCCCC[N+]1=CC=CC=C1 JOEPKDCJDKHSFJ-UHFFFAOYSA-M 0.000 description 1
- SAORNRFCWXEYSW-UHFFFAOYSA-M 1-propylpyridin-1-ium;bromide Chemical compound [Br-].CCC[N+]1=CC=CC=C1 SAORNRFCWXEYSW-UHFFFAOYSA-M 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007900 aqueous suspension 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
- 239000011324 bead Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical compound CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 description 1
- DVBJBNKEBPCGSY-UHFFFAOYSA-M cetylpyridinium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 DVBJBNKEBPCGSY-UHFFFAOYSA-M 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000003302 ferromagnetic material Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000696 magnetic material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- UJJUJHTVDYXQON-UHFFFAOYSA-N nitro benzenesulfonate Chemical compound [O-][N+](=O)OS(=O)(=O)C1=CC=CC=C1 UJJUJHTVDYXQON-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 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
- 229920001603 poly (alkyl acrylates) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- PEFYPPIJKJOXDY-UHFFFAOYSA-J potassium;tetrachloroalumanuide Chemical compound [Al+3].[Cl-].[Cl-].[Cl-].[Cl-].[K+] PEFYPPIJKJOXDY-UHFFFAOYSA-J 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09733—Organic compounds
- G03G9/0975—Organic compounds anionic
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/097—Plasticisers; Charge controlling agents
- G03G9/09733—Organic compounds
- G03G9/09758—Organic compounds comprising a heterocyclic ring
Definitions
- This invention relates to certain new N-substituted pyridinium salts which are useful as charge-control agents in dry electrostatographic toners and developers. More particularly, the new salts are thermally stable salts that can be well dispersed in typical toner binder materials to form toners having good charging properties and improved humidity insensitivit .
- an image comprising an electrostatic field pattern, usually of non-uniform strength, (also referred to as an electrostatic latent image) is formed on an insulative surface of an electrostatographic element by any of various methods.
- the electrostatic latent image may be formed electrophotographically (i.e., by i agewise photo-induced dissipation of the strength of portions of an electrostatic field of uniform strength previously formed on a surface of an electrophoto ⁇ graphic element comprising a photoconductive layer and an electrically conductive substrate), or it may be formed by dielectric recording (i.e., by direct electrical formation of an electrostatic field pattern on a surface of a dielectric material).
- the electrostatic latent image is then developed into a toner image by contacting the latent image with an electrostatographic developer. If desired, the latent image can be transferred to another surface before development.
- One well-known type of electrostatographic developer comprises a dry mixture of toner particles and carrier particles. Developers of this type are commonly employed in well-known electrostatographic development processes such as cascade development and magnetic brush development.
- the particles in such developers are formulated such that the toner particles and carrier particles occupy different positions in the triboelectric continuum, so that when they contact each other during mixing to form the developer, they become triboelectrically charged, with the toner particles acquiring a charge of one polarity and the carrier particles acquiring a charge of the opposite polarity. These opposite charges attract each other such that the toner particles cling to the surfaces of the carrier particles.
- the electrostatic forces of the latent image (sometimes in combination with an additional applied field) attract the toner particles, and the toner particles are pulled away from the carrier particles and become electrostatically attached imagewise to the latent image-bearing surface.
- the resultant toner image can then be fixed in place on the surface by application of heat or other known methods (depending upon the nature of the surface and of the toner image) or can be transferred to another surface, to which it then can be similarly fixed.
- the electrostatic attraction between the toner and carrier particles must be strong enough to keep the toner particles held to the surfaces of the carrier particles while the developer is being transported to and brought into contact with the latent image, but when that contact occurs, the electrostatic attraction between the toner particles and the latent image must be even stronger, so that the toner particles are thereby pulled away from the carrier particles and deposited on the latent image-bearing surface.
- the level of electrostatic charge on the toner particles should be maintained within an adequate range.
- the toner particles in dry developers often contain material referred to ' s a charge agent or charge-control agent, which helps to establish and maintain toner charge within an acceptable range.
- charge—control agents have been used and are described in the published patent literature.
- One general type of known charge-control agent comprises a quaternary ammonium salt. While many such salts are known, some do not perform an adequate charge-control function in any type of developer, some perform the function well in only certain kinds of developers, and some control charge well but produce adverse side effects.
- some of the known quaternary ammonium salt charge agents lack thermal stability and, thus, totally or partially decompose during attempts to mix them with known toner binder materials in well-known processes of preparing toners by mixing addenda with molten toner binders. Such processes are often referred to as melt-blending or melt-compounding processes and are commonly carried out at temperatures ranging from about 120° to about 200 ⁇ C. Thus, charge agents that are thermally unstable at temperatures at or below 200 ⁇ C can exhibit this decomposition problem. Also, some known quaternary ammonium salt charge agents exhibit high sensitivity to changes in environmental relative humidity and/or temperature, which can lead to erratic performance of the charge agents under changing environmental conditions causing a reduction in the quality of the image developed. It would, therefore, be desirable to provide new N-substituted pyridinium salts that could perform the charge-controlling function well in dry electrographic toners and developers, while avoiding or minimizing the drawbacks noted above. The present invention does this.
- the invention provides new N-substituted pyridinium salts having the structure
- R is a straight or branched chain alkyl group having from 1 to 24 carbon atoms, aralkyl in which the alkyl group has 1 to 20 carbon atoms and the aryl group has from 6 to 14 carbon atoms, R is hydrogen or a straight or branched chain alkyl or alkoxy group having from 1 to 24 carbon atoms, aralkyl or alkaryl in which the alkyl group has 1 to 20 carbon atoms and the aryl group has from 6 to 14 carbon atoms, unsubstituted aryl having from 6 to 14 carbon atoms or aryl having from 6 to 14 carbon atoms substituted with one or more nitro, alkoxy or halo groups and X is hydrogen, chlorine, bromine, fluorine or iodine.
- the salts of the invention have advantageous utility as charge agents in dry, particulate electrostatographic toners and developers.
- Such toners comprise a polymeric binder and a charge—control agent chosen from the inventive salts defined above.
- Such developers comprise carrier particles and the particulate toner defined above.
- the new salts of the invention provide good charge control in toners and developers.
- the inventive salts do not exhibit unacceptably high environmental sensitivity and have decomposition points well above 200 ⁇ C.
- the new N-substituted pyridinium salts of the invention can be conveniently prepared from readily available starting materials, such as a halide salt of the appropriate N-substituted pyridinium and an alkali metal salt of a tetraphenylborate.
- the N-substituted pyridinium halide may be prepared from an appropriate organic halide and pyridine or a substituted pyridine.
- pyridine can be quaternized with 1-bromotetradecane in acetonitrile to give N-tetradecylpyridinium bromide.
- N-substituted pyridinium salts useful in the present invention include, for example, N-ethylpyridinium tetraphenylborate, N-propyl- pyridinium tetraphenylborate, N-butylpyridinium tetraphenylborate, N-hexylpyridinium tetraphenyl ⁇ borate, N-dodecylpyridinium tetraphenylborate, N-tetradecylpyridinium tetraphenylborate, N-hexadecyl- pyridini ⁇ m tetraphenylborate, N-octadecylpyridinium tetraphenylborate, N-ethylpyridinium tetra- (4-chlorophenyl)borate, N-(4-methoxybenzyl)pyridinium tetrapheny
- N—substituted pyridinium salt is N—dodecylpyridinium tetraphenylborate.
- the inventive N-substituted pyridinium salt is mixed in any convenient manner (as. for example, by melt—blending as described in U.S. Pat. Nos . 4,684,596 and 4,394,430) with an appropriate polymeric toner binder material and any other desired addenda, and the mix is then ground to desired size to form a free-flowing powder of toner particles containing the charge agent.
- suitable methods of preparing electrostatographic toners comprising the charge—control agents of the present invention include those well known in the art such as spray drying, melt dispersion and dispersion polymerization.
- Such toner particles can have an average diameter between about 0.1 ⁇ m and about 100 ⁇ m, a value in the range from about 1.0 to about 30 ⁇ m being preferable for many currently used machines .
- charge-control agent to be added will depend, in part, on the particular N-substituted pyridinium charge-control agent selected and the particular polymer to which it is added. However, the amounts specified hereinabove are typical of a useful range of charge-control agent utilized in conventional dry toner materials.
- the polymers useful as toner binders with the salts of the present invention can be used alone or in combination and include those polymers conventionally employed in electrostatic toners.
- Useful polymers generally have a glass transition temperature within the range of from 50" to 120 ⁇ C.
- toner particles prepared from these polymers have relatively high caking temperature, for example, higher than about 60 ⁇ C, so that the toner powders can be stored for relatively long periods of time at fairly high temperatures without having individual particles agglomerate and clump together.
- the softening point of useful polymers preferably is within the range of from about 65 ⁇ C to about 200 ⁇ C so that the toner particles can readily be fused to a conventional paper receiving sheet to form a permanent image.
- Especially preferred polymers are those having a softening point within the range of from about 65° to about 120 ⁇ C.
- other types of receiving elements for example, metal plates such as certain printing plates, polymers having a softening point and glass transition temperature higher than the values specified above can be used.
- polymers which can be employed in toner particles with the salts of the present invention are polycarbonates, resin-modified maleic alkyd polymers, polyamides, phenol—formaldehyde polymers and various derivatives thereof, polyester condensates, modified alkyd polymers, aromatic polymers containing alternating methylene and aromatic units such as described in U.S. Pat. No. 3,809,554 and fusible crosslinked polymers as described in U.S. Pat. Re. No. 31,072.
- Typical useful toner polymers include certain polycarbonates such as those described in U.S. Pat. No. 3,694,359, which include polycarbonate materials containing an alkylidene diarylene moiety in a recurring unit and having from 1 to about 10 carbon atoms in the alkyl moiety.
- Other useful polymers having the above-described physical properties include polymeric esters of acrylic and methacrylic acid such as poly(alkyl acrylate), and poly(alkyl methacrylate) wherein the alkyl moiety can contain from 1 to about 10 carbon atoms. Additionally, other polyesters having the aforementioned physical properties are also useful.
- polyesters prepared from terephthalic acid (including substituted terephthalic acid), a bis(hydrox alkoxy)ph ⁇ nylalkane having from 1 to 4 carbon atoms in the alkoxy radical and from 1 to 10 carbon atoms in the alkane moiety (which can also be a halogen-substituted alkane), and an alkylene glycol having from 1 to 4 carbon atoms in the alkylene moiety.
- terephthalic acid including substituted terephthalic acid
- a bis(hydrox alkoxy)ph ⁇ nylalkane having from 1 to 4 carbon atoms in the alkoxy radical and from 1 to 10 carbon atoms in the alkane moiety (which can also be a halogen-substituted alkane)
- alkylene glycol having from 1 to 4 carbon atoms in the alkylene moiety.
- polystyrene-containing polymers can comprise, e.g., a polymerized blend of from about 50 to about 100 percent by weight of styrene, from 0 to about 45 percent by weight of a lower alkyl acrylate or methacrylate having from 1 to about 4 carbon atoms in the alkyl moiety such as methyl, ethyl, isopropyl, butyl, etc. and from about 5 to about 40 percent by weight of another vinyl monomer other than styrene, for example, a higher alkyl acrylate or methacrylate having from about 6 to 20 or more carbon atoms in the alkyl group.
- Typical styrene-containing polymers prepared from a copolymerized blend as described hereinabove are copolymers prepared from a monomeric blend of 40 to 60 percent by weight styrene or styrene homolog, from about 20 to about 50 percent by weight of a lower alkyl acrylate or methacrylate and from about 5 to about 30 percent by weight of a higher alkyl acrylate or methacrylate such as ethylhexyl acrylate (e.g., styrene-butyl acrylate-ethylhexyl acrylate copolymer).
- ethylhexyl acrylate e.g., styrene-butyl acrylate-ethylhexyl acrylate copolymer.
- Preferred fusible styrene copolymers are those which are covalently crosslinked with a small amount of a divinyl compound such as divinylbenzene.
- a divinyl compound such as divinylbenzene.
- a variety of other useful styrene- containing toner materials are disclosed in U.S. Pat. Nos. 2,918,460; Re 25,316; 2,788,288; 2,638,416; 2,618,552 and 2,659,670.
- addenda e.g., colorants, release agents, etc.
- toners containing salts of the invention e.g., toners containing toners containing salts of the invention.
- colorant materials selected from dyestuffs or pigments can be employed in such toners. Such materials serve to color the toner and/or render it more visible.
- suitable toner materials having the appropriate charging characteristics can be prepared without the use of a colorant material where it is desired to have a developed image of low optical density.
- the colorants can, in principle, be selected from virtually any of the compounds mentioned in the Colour Index Volumes 1 and 2, Second Edition.
- toners containing salts of this invention can be mixed with a carrier vehicle.
- the carrier vehicles which can be used to form such developer compositions can be selected from a variety of materials. Such materials include carrier core particles and core particles overcoated with a thin layer of film—forming resin.
- the carrier core materials can comprise conductive, non—conductive, magnetic, or non-magnetic materials.
- carrier cores can comprise glass beads; crystals of inorganic salts such as aluminum potassium chloride; other salts such as ammonium chloride or sodium nitrate; granular zircon; granular silicon; silicon dioxide; hard resin particles such as poly(methyl methacrylate); metallic materials such as iron, steel, nickel, carborundum, cobalt, oxidized iron; or mixtures or alloys of any of the foregoing. See, for example, U.S. Pat. Nos. 3,850,663 and 3,970,571.
- iron particles such as porous iron particles having oxidized surfaces, steel particles, and other "hard” or “soft” ferromagnetic materials such as gamma ferric oxides or ferrites, such as ferrites of barium, strontium, lead, magnesium, or aluminum. See, for example, U.S. Pat. Nos. 4,042,518; 4,478,925; and 4,546,060.
- the carrier particles can be overcoated with a thin layer of a film-forming resin for the purpose of establishing the correct tribo ⁇ electric relationship and charge level with the toner employed.
- suitable resins are the polymers described in U.S. Pat. Nos. 3,547,822; 3,632,512; 3,795,618 and 3,898,170 and Belgian Patent No. 797,132.
- Other useful resins are fluorocarbons such as polytetrafluoroethylene, ⁇ oly(vinylidene fluoride), mixtures of these, and copolymers of vinylidene fluoride and tetrafluoroethylene. See, for example, U.S. Pat. Nos.
- Such polymeric fluorohydrocarbon carrier coatings can serve a number of known purposes.
- One such purpose can be to aid the developer to meet the electrostatic force requirements mentioned above by shifting the carrier particles to a position in the triboelectric series different from that of the uncoated carrier core material, in order to adjust the degree of triboelectric charging of both the carrier and toner particles.
- Another purpose can be to reduce the frictional characteristics of the carrier particles in order to improve developer flow properties.
- Still another purpose can be to reduce the surface hardness of the carrier particles so that they are less likely to break apart during use and less likely to abrade surfaces (e.g., photoconductive element surfaces) that they contact during use.
- Yet another purpose can be to reduce the tendency of toner material or other developer additives to become undesirably permanently adhered to carrier surfaces during developer use (often referred to as scumming).
- a further purpose can be to alter the electrical resistance of the carrier particles.
- a typical developer composition containing the above—described toner and a carrier vehicle generally comprises from about 1 to about 20 percent by weight of particulate toner particles and from about 80 to about 99 percent by weight carrier particles.
- the carrier particles are larger than the toner particles.
- Conventional carrier particles have a particle size on the order of from about 20 to about 1200 microns, preferably 30-300 microns .
- toners containing salts of the present invention can be used in a single component developer, i.e., with no carrier particles.
- Toner and developer compositions containing salts of this invention can be used in a variety of ways to develop electrostatic charge patterns or latent images .
- Such developable charge patterns can be prepared by a number of means and be carried for example, on a light sensitive photoconductive element or a non-light—sensitive dielectric—surfaces element such as an insulator—coated conductive sheet.
- One suitable development technique involves cascading the developer composition across the electrostatic charge pattern, while another technique involves applying toner particles from a magnetic brush. This latter technique involves the use of a magnetically attractable carrier vehicle in forming the developer composition. After imagewise deposition of the toner particles, the image can be fixed, e.g., by heating the toner to cause it to fuse to the substrate carrying the toner.
- the unfused image can be transferred to a receiver such as a blank sheet of copy paper and then fused to form a permanent image.
- a receiver such as a blank sheet of copy paper
- the unfused image can be transferred to a receiver such as a blank sheet of copy paper and then fused to form a permanent image.
- N-ethylpyridinium tetraphenylborate was characterized by a combination of elemental analysis, nuclear magnetic resonance spectroscopy, melting point and thermogravimetric analysis. Elemental analysis calculated for C 31 H 30 BN (437.40): 87.17. C, 7.17 « H, 2.57o B and 3.37. N. Found: 87.57. C, 7.07. H, 2.47. B, and 3.27. N. TGA (10 ⁇ C/min; air): stable to 24: . NMR (DMSO): 81.49 (t, 3H), 4.53 (q, 2H), 6.59-7.3D ( , 20H), 7.89-8.13 (m. 2H), 8.32-8.57 (m, 2H). The other salts within the scope of the invention are prepared similarly.
- Example 2 The general procedure of Example 1 was repeated except that a solution of N-propylpyridinium bromide (97.6 g; 0.48 mol) in 976 mL of water and a solution of sodium tetraphenylborate (165.3 g; 0.48 mol) in 1653 mL of water was used to prepare
- Example 2 The general procedure of Example 1 was repeated except that a solution of N—pentylpyridinium bromide (137.8g; 0.60 mol) in 1378 mL of water and a solution of sodium tetraphenylborate (204.9 g; 0.60 mol) in 2049 mL of water was used to prepare 207.0 g (73.47.) of N-pentylpy idinium tetraphenylborate: m.p. 170-172°C; TGA (10 ⁇ C/min; air): stable to 244 ⁇ C. Analysis calculated for C 34 H 36 BN (469.49); 87.07. C, 7.77. H, 2.37. B and 3.07. N. Found: 87.47. C, 7.77. H, 2.27. E and 3.07. N.
- Example 2 PYRIDINIUM TETRAPHENYLBORATE The general procedure of Example 1 was repeated except that a solution of N-dodecyl pyridinium bromide (50.0 g; 0.153 mol) in 500 mL of water and a solution of sodium tetraphenylborate (52.2 g; 0.153 mol) in 522 mL of water was used to prepare
- Example 8 PREPARATION OF N-HEXA- DECYLPYRIDINIUM TETRAPHENYLBORATE
- N-octadecylpyridinium bromide (50.0 g; 0.121 mol) in 500 mL of water and a solution of sodium tetraphenylborate (41.5 g; 0.121 mol) in 415 mL of water was used to prepare 40.5 g (51.3%) of
- N-octadecylpyridinium tetraphenylborate m.p. 88-90°C;
- Examples 1-9 were compared to quaternary ammonium salts outside the scope of the present invention in regard to decomposition point.
- Decomposition temperatures were determined by thermal gravimetric analysis (TGA) measured on a DuPont 1090 thermal analyzer equipped with a 951 thermal gravimetric analyzer (10 c C/min; air). A sample of known weight is placed in the thermal analyzer and its weight is monitored while the temperature is raised at a constant rate, in this case 10 ⁇ C/min. The temperature at which significant weight loss begins to occur is taken as the decomposition temperature. Results are presented in Table 1.
- VERSUS RELATIVE HUMIDITY CHANGES The following example compares a developer composition comprising a charge-control agent of the present invention to developer compositions of the prior art containing conventional quaternary ammonium salt charge—control agents with respect to the stability of the charge to mass ratio of the toner as a function of relative humidity.
- the toner of the present invention included, as a charge—control agent, N-dodecylpyridinium tetraphenylborate, prepared as described in Example 6 above, and the prior art toners contained, as a charge-control agent, N—octadecyl— ,N—dimethylbenzylammonium nitrobenzene sulfonate and tetrabutylammonium triflate.
- the toners were prepared by a polymer suspension process known to the art as the limited coalescence process as described in U.S. Pat. No. 4,833,060.
- the concentration of charge agent in the toner was 0.2494 percent by weight based on the total weight of the toner in all cases and each toner contained in addition to the charge agent, 12.469 percent by weight based on the total weight of toner of a cyan phthalocyanine pigment dispersed in a styrene-acrylic resin mixture. Specifically, 75 parts by weight of an 807. styrene — 207.
- butylacrylate copolymer sold by Hercules, Inc., under the trade name Piccotoner 1221 was dissolved together with 12.5 parts by weight of a cyan phthalocyanine pigment dispersed in 12.5 parts by weight of either a styrene-acrylic resin sold by Goodyear, Inc., under the trade name Pliotone 4003 or a styrene-acrylic resin sold by Goodyear, Inc., under the trade name Pliotone 2102 and 0.25 parts by weight of charge agent in about 400 parts by weight of ethyl acetate.
- the solution had a solids content of about 207. by weight, based on the total weight of the solution, the pigment content being about 12.469% by weight of the total solids content and the charge agent being about 0.2 ⁇ 94% by weight of the total solids content.
- aqueous solution buffered to a pH of about 4 (phthalate buffer) containing about 5 parts by weight of a particulate stabilizer comprising 50% silica having a particle size of about 20-25 nanometers, this material being sold under the designation Ludox TM by the duPont Company and about 1.5 parts by weight of a 10 percent solution of poly(adipic acid-co-methylaminoethanol).
- phthalate buffer containing about 5 parts by weight of a particulate stabilizer comprising 50% silica having a particle size of about 20-25 nanometers, this material being sold under the designation Ludox TM by the duPont Company and about 1.5 parts by weight of a 10 percent solution of poly(adipic acid-co-methylaminoethanol).
- the system Upon addition of the styrene butylacrylate copolymer/solvent organic phase to the aqueous suspension, the system was immediately subjected to shear using a Polytron sold by Brinkmann followed by a Microfluidizer sold by Microfluidics, Inc., to form droplets consisting of the polymer, charge agent and pigment dispersion. Upon exiting the Microfluidizer, the solvent was allowed to evaporate by stirring under a stream of nitrogen. The particles were then filtered and treated overnight in a 1 N aqueous potassium hydroxide solution followed by another overnight treatment in a 0.1 N potassium hydroxide solution to dissolve away the particulate stabilizer (i.e., the silica).
- a Polytron sold by Brinkmann
- Microfluidizer sold by Microfluidics, Inc.
- Particle size refers to median volume weighted diameter as measured by conventional diameter measuring devices such as the Coulter Multisizer, sold by Coulter, Inc.
- Median volume weighted diameter is the size at which one-half of the volume of the sample is composed of particles larger than the median size and one-half of the volume of the sample is composed of particles smaller than the median size.
- Developer ' compositions were then prepared by blending together 7 parts by weight of each of the toners thus prepared and 93 parts by weight of strontium ferrite carrier particles and (b) 10 parts by weight of each of the toners thus prepared and 90 parts by weight of the strontium ferrite carrier particles.
- the ferrite carrier particles were thinly coated with about 1.57. of a polymethylmethacrylate resin available from Soken, Inc. under the trade name Soken 1201 and 0.5% of a polyvinyJidene fluoride resin available from Pennwalt Co.
- Kynar 301F under the trade name Kynar 301F, except for the carrier particles present in the developer compositions containing tetrabutylammonium triflate as the charge—control agent in the toner in which case the ferrite carrier particles were coated with 2%, Kynar 301F alone.
- the developers were shaken for one minute and separately aged at low (about 157.) relative humidity at 82 ⁇ F, medium (about 507.) relative humidity at 72°F, and higher (about 82%) relative humidity at 72°F for one hour.
- the element was composed of, in sequence, a film support, an electrically conducting layer and the insulating layer.
- the test element was connected via the conducting layer to an electrometer and the charge was measured during the plating (i.e., toning) operation.
- the registered charge was divided by the weight of the toner plated onto the element to obtain the charge per mass of toner.
- Table II show the percentage decrease of the triboelectric charge from 15% to 82% relative humidity.
- N-dodecylpyridinium tetraphenylborate 3 0.25 7 6.9%
- c N-dodecylpyridinium tetraphenylborate 3 0.25 10 6.4% tetrabutylammonium triflate 3 0.25 7 40.0%
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US56071990A | 1990-07-31 | 1990-07-31 | |
US560719 | 2000-04-27 |
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EP19910913878 Withdrawn EP0541631A1 (de) | 1990-07-31 | 1991-07-24 | N-substituierte pyricliniumborate |
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JP (1) | JPH05509310A (de) |
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DE4416265A1 (de) * | 1994-05-07 | 1995-11-09 | Basf Ag | Elektrostatische Toner, enthaltend Phenacylverbindungen |
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DE932533C (de) * | 1953-05-30 | 1955-09-01 | Agfa Ag Fuer Photofabrikation | Empfindlichkeitssteigerung von Halogensilberemulsionen |
US3567453A (en) * | 1967-12-26 | 1971-03-02 | Eastman Kodak Co | Light sensitive compositions for photoresists and lithography |
US4033905A (en) * | 1975-11-05 | 1977-07-05 | Rca Corporation | Method for increasing the conductivity of electrically resistive organic materials |
DE58903604D1 (de) * | 1988-11-03 | 1993-04-01 | Hoechst Ag | Ammonium- und immoniumverbindungen und verfahren zu ihrer herstellung. |
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- 1991-07-24 JP JP51296991A patent/JPH05509310A/ja active Pending
- 1991-07-24 EP EP19910913878 patent/EP0541631A1/de not_active Withdrawn
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