MXPA00004779A - Toner, developer compositions, process of imaging, polyester and process for preparation of polyester - Google Patents
Toner, developer compositions, process of imaging, polyester and process for preparation of polyesterInfo
- Publication number
- MXPA00004779A MXPA00004779A MXPA/A/2000/004779A MXPA00004779A MXPA00004779A MX PA00004779 A MXPA00004779 A MX PA00004779A MX PA00004779 A MXPA00004779 A MX PA00004779A MX PA00004779 A MXPA00004779 A MX PA00004779A
- Authority
- MX
- Mexico
- Prior art keywords
- organic pigment
- acid
- pigment composition
- composition according
- terephthalate
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 229
- 229920000728 polyester Polymers 0.000 title claims description 74
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 13
- 238000003384 imaging method Methods 0.000 title description 7
- 229920001225 Polyester resin Polymers 0.000 claims abstract description 75
- 239000004645 polyester resin Substances 0.000 claims abstract description 75
- 239000000654 additive Substances 0.000 claims abstract description 50
- 239000003086 colorant Substances 0.000 claims abstract description 38
- 230000002209 hydrophobic Effects 0.000 claims abstract description 38
- 230000000996 additive Effects 0.000 claims abstract description 20
- 239000000049 pigment Substances 0.000 claims description 262
- -1 alkaline earth metal salt Chemical class 0.000 claims description 126
- 229920005989 resin Polymers 0.000 claims description 55
- 239000011347 resin Substances 0.000 claims description 55
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000002245 particle Substances 0.000 claims description 32
- 230000035945 sensitivity Effects 0.000 claims description 29
- 239000004698 Polyethylene (PE) Substances 0.000 claims description 25
- 229920000573 polyethylene Polymers 0.000 claims description 25
- 239000011780 sodium chloride Substances 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 22
- 239000000178 monomer Substances 0.000 claims description 21
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 19
- 239000000969 carrier Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 16
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 14
- 150000002009 diols Chemical class 0.000 claims description 13
- 239000004743 Polypropylene Substances 0.000 claims description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 12
- 125000001165 hydrophobic group Chemical group 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 229920001155 polypropylene Polymers 0.000 claims description 12
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
- HTXMGVTWXZBZNC-UHFFFAOYSA-N 3,5-bis(methoxycarbonyl)benzenesulfonic acid Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(S(O)(=O)=O)=C1 HTXMGVTWXZBZNC-UHFFFAOYSA-N 0.000 claims description 10
- JFCQEDHGNNZCLN-UHFFFAOYSA-N Glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 10
- WLJVNTCWHIRURA-UHFFFAOYSA-N Pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 10
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 10
- 239000006229 carbon black Substances 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 claims description 10
- 229910052725 zinc Inorganic materials 0.000 claims description 10
- 239000011701 zinc Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000011068 load Methods 0.000 claims description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 8
- 229910052788 barium Inorganic materials 0.000 claims description 8
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052790 beryllium Inorganic materials 0.000 claims description 8
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium(0) Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 150000002430 hydrocarbons Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052744 lithium Inorganic materials 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 8
- TVFDJXOCXUVLDH-UHFFFAOYSA-N Cesium Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 229910052792 caesium Inorganic materials 0.000 claims description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 7
- 229910052791 calcium Inorganic materials 0.000 claims description 7
- 239000011575 calcium Substances 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- 239000011777 magnesium Substances 0.000 claims description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims description 7
- 150000004706 metal oxides Chemical class 0.000 claims description 7
- 238000006068 polycondensation reaction Methods 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N 1-Decanol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 6
- ZWRUINPWMLAQRD-UHFFFAOYSA-N 1-Nonanol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 6
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N 1-Tetradecanol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- OOCCDEMITAIZTP-QPJJXVBHSA-N Cinnamyl alcohol Natural products OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 claims description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N Dodecanol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N Isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- OYHQOLUKZRVURQ-IXWMQOLASA-N Linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N Oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 6
- QHGNHLZPVBIIPX-UHFFFAOYSA-N Tin(II) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-M palmitate Chemical group CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 6
- ZWPWUVNMFVVHHE-UHFFFAOYSA-N terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=C(C(O)=O)C=C1 ZWPWUVNMFVVHHE-UHFFFAOYSA-N 0.000 claims description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- KLZYRCVPDWTZLH-UHFFFAOYSA-N 2,3-dimethylbutanedioic acid Chemical compound OC(=O)C(C)C(C)C(O)=O KLZYRCVPDWTZLH-UHFFFAOYSA-N 0.000 claims description 5
- YLAXZGYLWOGCBF-UHFFFAOYSA-N 2-dodecylbutanedioic acid Chemical compound CCCCCCCCCCCCC(C(O)=O)CC(O)=O YLAXZGYLWOGCBF-UHFFFAOYSA-N 0.000 claims description 5
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Azelaic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 5
- WXUAQHNMJWJLTG-UHFFFAOYSA-N Methylsuccinic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 claims description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims description 5
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000001530 fumaric acid Substances 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000001294 propane Substances 0.000 claims description 5
- 239000001384 succinic acid Substances 0.000 claims description 5
- JZUMVFMLJGSMRF-UHFFFAOYSA-N 2-Methyladipic acid Chemical compound OC(=O)C(C)CCCC(O)=O JZUMVFMLJGSMRF-UHFFFAOYSA-N 0.000 claims description 4
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N Phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- PXGZQGDTEZPERC-UHFFFAOYSA-N cyclohexane-1,4-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002334 glycols Chemical class 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-M laurate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 4
- 229940070765 laurate Drugs 0.000 claims description 4
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 4
- 229960004889 salicylic acid Drugs 0.000 claims description 4
- UNVGBIALRHLALK-UHFFFAOYSA-N (±)-1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 claims description 3
- WNJKAUYCWGKTCD-UHFFFAOYSA-N 1,1-dihydroxy-2-methylpentane-3-sulfonic acid Chemical compound CCC(S(O)(=O)=O)C(C)C(O)O WNJKAUYCWGKTCD-UHFFFAOYSA-N 0.000 claims description 3
- MSECYUNQFUJMKR-UHFFFAOYSA-N 1,1-dihydroxybutane-2-sulfonic acid Chemical compound CCC(C(O)O)S(O)(=O)=O MSECYUNQFUJMKR-UHFFFAOYSA-N 0.000 claims description 3
- CTOBOPFPKGSNLQ-UHFFFAOYSA-N 1,1-dihydroxyethanesulfonic acid Chemical compound CC(O)(O)S(O)(=O)=O CTOBOPFPKGSNLQ-UHFFFAOYSA-N 0.000 claims description 3
- ADGYXODRVKLEFW-UHFFFAOYSA-N 1,1-dihydroxyhexane-2-sulfonic acid Chemical compound CCCCC(C(O)O)S(O)(=O)=O ADGYXODRVKLEFW-UHFFFAOYSA-N 0.000 claims description 3
- BIPKBRPARYQCCC-UHFFFAOYSA-N 1,1-dihydroxypentane-3-sulfonic acid Chemical compound CCC(S(O)(=O)=O)CC(O)O BIPKBRPARYQCCC-UHFFFAOYSA-N 0.000 claims description 3
- YNWJFLHCGNIJKI-UHFFFAOYSA-N 1,1-dihydroxypropane-2-sulfonic acid Chemical compound OC(O)C(C)S(O)(=O)=O YNWJFLHCGNIJKI-UHFFFAOYSA-N 0.000 claims description 3
- BMRWNKZVCUKKSR-UHFFFAOYSA-N 1,2-Butanediol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 3
- 229940058015 1,3-butylene glycol Drugs 0.000 claims description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-Butanediol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 3
- ALQSHHUCVQOPAS-UHFFFAOYSA-N 1,5-Pentanediol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N 1,6-Hexanediol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-Heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims description 3
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N 1-Hexanol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 3
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims description 3
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 3
- QLFXKDAOPACZTK-UHFFFAOYSA-N 2,3,3-trimethylhexan-1-ol Chemical compound CCCC(C)(C)C(C)CO QLFXKDAOPACZTK-UHFFFAOYSA-N 0.000 claims description 3
- AKNUHUCEWALCOI-UHFFFAOYSA-N 2-[ethyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 claims description 3
- RAADBCJYJHQQBI-UHFFFAOYSA-N 2-sulfoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(S(O)(=O)=O)=C1 RAADBCJYJHQQBI-UHFFFAOYSA-N 0.000 claims description 3
- DPBYXPSNKVDNCZ-UHFFFAOYSA-N 4-hydroxy-2-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1S(O)(=O)=O DPBYXPSNKVDNCZ-UHFFFAOYSA-N 0.000 claims description 3
- QVEFNWDGDYMNPU-UHFFFAOYSA-N 6-[3,5-bis(methoxycarbonyl)phenyl]naphthalene-2-sulfonic acid Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(C=2C=C3C=CC(=CC3=CC=2)S(O)(=O)=O)=C1 QVEFNWDGDYMNPU-UHFFFAOYSA-N 0.000 claims description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N Anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N Cetyl alcohol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 3
- MNWFXJYAOYHMED-UHFFFAOYSA-N Heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N Itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- FBUKVWPVBMHYJY-UHFFFAOYSA-N Nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N Oleyl alcohol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 3
- 235000021314 Palmitic acid Nutrition 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 3
- RINCXYDBBGOEEQ-UHFFFAOYSA-N Succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims description 3
- KJIOQYGWTQBHNH-UHFFFAOYSA-N Undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 claims description 3
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 3
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- VKWNTWQXVLKCSG-UHFFFAOYSA-N N-ethyl-1-[(4-phenyldiazenylphenyl)diazenyl]naphthalen-2-amine Chemical compound CCNC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 VKWNTWQXVLKCSG-UHFFFAOYSA-N 0.000 description 1
- 229940117969 NEOPENTYL GLYCOL Drugs 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N Phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 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
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical group N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N Triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N Trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N al2o3 Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000005227 alkyl sulfonate group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- VXLGWCOZCKOULK-UHFFFAOYSA-K aluminum;cerium(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[Al].[Ce+3] VXLGWCOZCKOULK-UHFFFAOYSA-K 0.000 description 1
- FHNWMAGGEATMIW-UHFFFAOYSA-N aluminum;oxotin Chemical compound [Al].[Sn]=O FHNWMAGGEATMIW-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000001588 bifunctional Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- LOGBRYZYTBQBTB-UHFFFAOYSA-N butane-1,2,4-tricarboxylic acid Chemical compound OC(=O)CCC(C(O)=O)CC(O)=O LOGBRYZYTBQBTB-UHFFFAOYSA-N 0.000 description 1
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 1
- LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 1
- 230000000254 damaging Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000004059 degradation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- PGZPBNJYTNQMAX-UHFFFAOYSA-N dimethylazanium;methyl sulfate Chemical compound C[NH2+]C.COS([O-])(=O)=O PGZPBNJYTNQMAX-UHFFFAOYSA-N 0.000 description 1
- CYUUZGXOQDCCGH-UHFFFAOYSA-N dodecyl dodecanoate Chemical compound CCCCCCCCCCCCOC(=O)CCCCCCCCCCC CYUUZGXOQDCCGH-UHFFFAOYSA-N 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000000989 food dye Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910000460 iron oxide Inorganic materials 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- LATKICLYWYUXCN-UHFFFAOYSA-N naphthalene-1,3,6-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 LATKICLYWYUXCN-UHFFFAOYSA-N 0.000 description 1
- KREXGRSOTUKPLX-UHFFFAOYSA-N octadecanoic acid;zinc Chemical compound [Zn].CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O KREXGRSOTUKPLX-UHFFFAOYSA-N 0.000 description 1
- CNRZQDQNVUKEJG-UHFFFAOYSA-N oxo-bis(oxoalumanyloxy)titanium Chemical compound O=[Al]O[Ti](=O)O[Al]=O CNRZQDQNVUKEJG-UHFFFAOYSA-N 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000000545 stagnation point adsorption reflectometry Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229960001663 sulfanilamide Drugs 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 1
- XOSXWYQMOYSSKB-UHFFFAOYSA-L water blue Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=C(N)C(C)=CC(C(=C2C=CC(C=C2)=NC=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S(O)(=O)=O)=CC=2)=C1 XOSXWYQMOYSSKB-UHFFFAOYSA-L 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Abstract
A toner composition comprised of a polyester resin with containing at least one hydrophilic group and hydrophobic end groups, colorant, optional wax, optional charge additive, and optional surface additives.
Description
COMPOSITIONS OF ORGANIC PIGMENT AND DEVELOPER
BACKGROUND OF THE INVENTION The present invention is directed generally to organic pigment and developer compositions, and more specifically, the present invention is directed to a developer composition comprised of carrier, and organic pigment containing a polyester with hydrophilic groups and hydrophobic and wherein the main chain of the resin contains a hydrophilic moiety, ie, for example, where the moiety refers to a group or groups on the polymer backbone in an amount of, for example, from about 0.5 to about 3. percent based on the amount of polyester polymer of organic pigment, or portions which, for example, impart or assist in imparting excellent triboelectric characteristics and with rapid mixing, and where the final groups of the polyester resin are modified with or contain hydrophobic portions, groups or segments, preferably two, present is in an amount of, for example, from about 0.5 to about 2 percent or parts based on the amount of polyester polymer to, for example, impart or assist in imparting excellent relative humidity sensitivity to the organic pigment. In the modalities, here provided in agreement
with the present invention organic pigment compositions comprised of dye particles, and resin particles comprised of a polyester resin containing hydrophilic portions such as a sodium sulfonate group or groups, in an amount for the portions, groups, or segments of, for example, from about 0.5 to about 3 weight percent of the polyester or polymer resin and preferably from about 1 to about 2 weight percent resin, and hydrophobic, ie, for example, non-polar groups, or which do not bind to water, such as alkyl, alkylene, such as, for example, from 6 to about 120 carbon atoms, such as hexyl, lauryl, stearyl, cetyl, polyethylene, polypropylene and the like. More specifically, in the embodiments of the present invention, there is provided an organic pigment comprised of a dye, especially pigment particles, optionally a bulking agent, optionally a waxy component, and a polyester resin containing a hydrophilic portion. on the main chain, and hydrophobic end groups, and a polyester which is illustrated by Formulas I through III.
p
neither
where R is an alkylene group, such as an ethylene, propylene, butylene, divalent ethylene oxyethylene or generally a hydrocarbon, wherein from about 2 to about 24 carbon atoms, from about 2 to about 22, and preferably from about 2 to about 20 carbon atoms, and more specifically, with 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 , 21 or 22 atoms of
| ff # ^ * '! _ carbon; a cycloalkylene such as cyclohexylene or a 1,4-dimethylcyclohexylene group; X is an aromatic group, such as arylene, with, for example, from about 6 to about 14 carbon atoms, such as the portions of phenylene, isophthallene, terephthalene, or phthalylene, or an olefinic group (or groups through it) ), such as vinylene, methylvinylene or an alkylene group such as ethylene, propylene, butylene, pentylene, hexylene, and the like; R 'is a hydrophobic group or groups, such as an alkyl group, for example, from about 2 to about 120 carbon atoms, such as hexyl, heptyl, octyl, lauryl, stearyl, alkylene, such as polyethylene or polypropylene; and m and n represent the number of random segments, such as a number from about 10 to about 100 for n and from about 20 to about 2,000 for m or 20 times n; S is a hydrophilic group, such as an alkaline earth metal salt of an arylene sulfonate or alkylene sulfonate, and more specifically, an alkaline earth metal such as lithium, sodium, potassium, cesium, beryllium, magnesium, calcium or barium, an arylene sulfonate. such as phenylene sulfonate, isophthalylene-5-sulfonate, terephthalene-sulfonate, phthalenesulfonate, or an alkylenesulfonate such as propylene sulfonate, butynesulfonate, pentylenesulfonate, hexylene sulfonate; And it can be X or S. The polyester resin can be branched or crosslinked using trifunctional or multifunctional reagents, such as trimethylolpropane or pyromellitic acid, in an amount, for example, from about 0.1 to about 6 mole percent based on the diacid. or initial diester selected to prepare the polyester resin, and branching agent which can be represented in Formulas I to III above incorporating the branching segments, p, q, ros as illustrated in the formulas
Ace
where R "is a multivalent aromatic radical with, for example, from about 6 to about 30 carbon atoms, or an aliphatic radical with from about 3 to about 20 carbon atoms, such as the tri or tetravalent derivatives of propane, butane, pentane, hexane, cyclohexane, heptane, octane, benzene, naphthalene, anthracene and the like, and p, q, rys represent the branching segments and in the embodiments each are from about 0.1 to about 6 mole percent based on the initial diacid or diester used to generate the resin and provided that the sum of the segments pyq, orys is 100 mole percent of the polyester resin In the embodiments, the present invention relates to the preparation of the polyester resin, and where the hydroxyl groups and the final acid of the resulting polyester were minimized and preferably avoided.Polyester resins are known to contain acids and hydroxyl of about 20 to about 1,000 milliequivalents per gram of polyester, usually present as end groups. It is believed that these final hydrophilic groups can cause the organic pigment compositions to have tribo-charge performance which is sensitive to moisture, where the triboelectric charge ratio of low moisture to high humidity organic pigment compositions is from about 2.8 to about 4.5, and usually from about 3.0 to about 3.5. To reduce
According to the sensitivity to relative humidity of polyester-based organic pigments, the present invention minimizes the final hydrophilic groups, such as the hydroxyl or acid portions on the polyester resin, by protecting the ends of the polyester with hydrophobic groups, such as alkyl portions, consequently resulting in organic pigments with low sensitivity to moisture in embodiments such as from about 1.0 to about 2.8 and preferably from about 1.0 to about 2.5. Another embodiment of the present invention relates to obtaining an organic pigment composition with excellent triboelectric stability and rapid mixing in less than about 1 minute and preferably less than about 30 seconds, for example from about 5 to about 15 seconds, organic pigment which contains a polyester resin with a hydrophilic portion, such as a sodium sulfonate group, present on the main chain of the resin. A further embodiment of the present invention relates to the preparation of a polyester resin with monofunctional monomers that protect the ends of the polyester resin to result in the polyester resin mentioned above with final hydrophobic groups, and where the concentration of the monofunctional hydrophobic monomers is from about 0.1 mole percent to about 4 mole percent based on the initial diacid or diester used to generate the resin, and therefore controls the weight average molecular weight of about 4,000 grams per mole to about 250,000 grams per mole, especially when monofunctional monomers are selected with a carbon chain length of from about 4 to about 24 or where larger monomers such as 1,2-naphthalene ethanol, or phenylmethanol are used; and wherein a hydrophilic portion such as a sodium sulfonate group is present in the main chain of the polyester resin, and wherein the concentration of the hydrophilic portion is from about 0.1 to about 5 weight percent of the resin, and so preferably from about 0.5 to about 2.5 weight percent of the resin. The organic pigment composition mentioned above and the developer thereof, ie the organic pigment mixed with a carrier, has a low sensitivity to relative humidity for organic pigments in the embodiments of the present invention, which is desirable since the triboelectric load remains stable with changes in humidity conditions environmental. Additionally, organic pigments possess rapid blending characteristics, such as less than about 60 seconds, and preferably less than 30 seconds, for example about 5 to about 15 seconds, and low minimum fixing temperatures, such as 130 ° C to about 145 ° C, with wide melting latitudes, such as from about 30 ° C to about 90 ° C. Copiers and printers equipped with two-component developers, ie, an organic pigment as a component mixed with the carrier as the other component, can exhibit a positive or negative triboelectric charge with a magnitude of about 5 microcuffs per gram to about 40 microcuffs per gram. gram. This triboelectric charge allows the organic pigment particles to be transferred to the latent image of the photoreceptor with an opposite charge, thereby forming an organic pigment image on the photoreceptor, which is subsequently transferred to a paper or a transparent substrate, and then it will be subjected to fusion or fixation processes. In those developing systems, it is important that the triboelectric charge be stable at different ambient humidity conditions so that the triboelectric charge does not change substantially more than about 5 to about 10 microcouples per gram. A change of more than about 5 microcuffs per gram to about 10 microcuffs per gram in the triboelectric charge of the organic pigment developer can produce non-uniform organic pigment images or result in deposition of organic pigment on the photoreceptor, thereby unbalancing the density or gray scale observed in the revealed images, or results in unrevealed images at all. Generally, moisture ranges can differ from less than about 20 percent in dry regions to more than about 80 percent in humid regions and some geographic regions can exhibit fluctuations in the level of up to about 50 percent to about 90 percent. humidity in the same day. In such climates, it is important that the developed triboelectric charge does not change more than about 5 microcoulumbios per gram to about 10 microcoulumbios per gram. Since the resins of the organic pigment generally represent from about 80 percent to about 98 percent by weight of the organic pigment, the sensitivity of the resin to moisture or moisture conditions should be minimized so as not to affect the adverse way the triboelectric charge of the same. In addition, the organic pigments should preferably possess rapid mixing characteristics, so that when the copiers and printers are replenished with fresh organic pigments, the developers can restore the necessary triboelectric charge within less than 1 minute, and preferably less than 30 minutes. seconds. A number of organic pigment polymer resins used as organic pigment compositions, such as for example styrene-acrylates, styrene-methacrylates, styrene-butadienes and especially polyesters, contain from about 0.1 to about 2 weight percent moisture, and in In some cases, the moisture content of the polyesters may change from about 0.1 to about 4 weight percent at moisture levels ranging from about 10 to about 100 percent, or more usually from about 20 percent to about 80. percent moisture These changes in the moisture content of the resin can have a dramatic adverse effect on the triboelectric charge of the organic pigment and revealing it. The sensitivity to relative humidity of the organic pigment is commonly measured by first making an organic pigment comprised of a pigment, an optional charge control agent and a resin, then mixing the organic pigment from about 3 weight percent to about 7 weight percent with a carrier. The developer composition is then balanced at various moisture levels in a sealed chamber at controlled temperatures of 60 ° F (15.55 ° C) to a 20% RH and 80 ° C to 80 ° F (26.66CC) for a period of time. period of approximately 48 hours. The triboelectric charge for the same developer composition is then measured at different moisture levels and the results are analyzed by various methods, such as plotting the tribo-electric charge as a function of the moisture level and observing the regions in which dramatic changes occur. Another measurement method comprises dividing the aforementioned graphical interpolation of the tribo against the moisture level in three regions, where the region A is from about 0 to about 30 percent moisture, the B region is from about 30 to about 65 percent of moisture, and region C is greater than about 65 percent moisture to about 100 percent. Since these measurements are embarrassing and time consuming, the triboelectric charge can be measured after subjecting the organic pigment developer composition to two moisture levels, such as a relative humidity of 20 percent and a relative humidity of 80 percent, and then calculating the relative sensitivity for the ratio of the triboelectric charge of relative humidity from 20 to 80 percent as follows Equation 1:
Tribo-electric load at RH of 20% at 60 ° F (15.55 ° C)
Sensitivity to Relative Humidity = Tribolectric Load to RH of 80% at 80 ° F (26.66 ° C)
where RH is the relative humidity. Thus, if the sensitivity of the relative humidity is about 1, the composition of organic pigment is considered insensitive to moisture, whereas if the sensitivity to moisture is greater than 3, the composition of organic pigment is considered sensitive to humidity. It is generally believed that organic pigments prepared with a number of polymeric materials exhibit a relative sensitivity greater than 1.0, and in general, organic pigments based on styrene and butadiene or styrene and acrylate have higher moisture sensitivities than 1.0 and less than about 2.5, while, in general, organic pigments based on polyester have a sensitivity to relative humidity greater than 2.5 and less than approximately 5. Consequently, an advantage of binder resins of the styrene type Acrylate or styrene-butadiene for organic pigments over polyester is its lower sensitivity to relative humidity. It is known that polyesters have advantages over styrene-based resins, such as low fixation temperatures of about 120 ° C to about 140 ° C, and deviating properties different from those of vinyl. Therefore, there is a need for organic pigment compositions comprised of a resin possessing many of the above-mentioned advantages, such as low fixation temperature of about 120 ° C to about 140 ° C, deviating properties different from those of vinyl , in addition to low sensitivity of the tribocharge as a function of relative humidity, so that the ratio of the triboelectric charge to a RH of 20 percent and 80 percent is from approximately 1.0 to approximately 2.5. These and other advantages are maintained in embodiments with the organic pigment compositions of the present invention comprised of a pigment, optionally a charge control agent, and a modified polyester resin where the final groups are hydrophobic portions, and the organic pigment exhibits a low fixing temperature of about 120 ° C to about 140 ° C, deviating properties different from those of vinyl, and low sensitivity to relative humidity, such as from about 1.0 to about 2.5. In addition, the presence of hydrophobic end groups provides an improved process for obtaining polyesters.
Specifically, the concentration of monomer and monofunctional groups provides control of the molecular weight of the polyester product, and its reproducibility. The process for the preparation of the polyester resins of the present invention is known as a gradual condensation or polymerization process. The condensation process involves the addition of bifunctional monomers, which results in dimers, followed by the reaction of the dimers with dimers to form tetramers, or dimers with monomers to form trimers. The reaction sequence then continues so that those dimers, trimers and tetramers react with each other to form multiples thereof, known in the art as oligomers, which in turn react with other oligomers to form the polyester. In this kinetic scheme, the degree of polymerization is achieved by terminating the reaction at the desired point, and therefore depends on time. It is known that obtaining a specific degree of polymerization depending on the time of polymerization of the polymerization process by gradual reaction is very difficult. One method for controlling the degree of polymerization is to adjust the composition of the reaction mixture away from the stoichiometric equivalence, adding a non-volatile monofunctional agent in an amount of about 0.1 mole percent to about 4 mole percent based on the diacid or diester initial used to produce the resin. In the present invention, the monofunctional monomers used are, for example, hydrophobic monomers. The degree of polymerization can be further controlled by the amount of monofunctional monomer used, thereby limiting the degree of polymerization as determined by its concentration, so that the total amount of final groups is to provide the amount of monofunctional monomer employed. . This helps the reproducibility of the product by adjusting the amount of monofunctional monomer to the limit of the desired degree of polymerization, thereby avoiding total dependence on polymerization time. Additionally, the organic pigment resin of the present invention contains a hydrophilic portion, such as an alkali salt of a sulfonate group, which group is believed to impart long-term triboelectric stability, such as from about 250,000 to about
1,000,000 impressions or copies, and whose function also allows rapid mixing in less than about 1 minute and preferably less than about 30 seconds. The organic pigment compositions of the present invention in the embodiments thereof have excellent characteristics as indicated herein, and maintain their triboelectric charge characteristics during a prolonged number of imaging cycles up to, for example, 1,000,000 in a number of modalities.
There is a need for organic pigments with low sensitivity to relative humidity, such as from about 1 to about 2.8, and preferably from about 1 to about 2.5, as calculated by Equation 1, and where excellent stability is achieved triboelectric, such as from about 250,000 to 1,000,000 impressions or copies, with a rapid mixing time, such as less than about 1 minute and preferably less than about 10 seconds, and where low minimum fixing temperatures are obtained, such as from about 120 ° C to about 140 ° C with a wide melting latitude such as from about 30 ° C to about 45 ° C, where the melting latitude is considered the difference between the minimum fixing temperature and the temperature to which the organic pigment is diverted towards the fusion member. These and other needs can be met with the present invention in the modalities thereof. PREVIOUS TECHNIQUE Certain organic polyester pigment resins are known, by way of reference, for example U.S. Pat. 25 3,590,000 and 4,525,445, which illustrate a linear polyester preferably comprised of propoxylated bisphenol A
^ m i¿a £ iEjftfa »__ Ms.3H_ ££ s__ and fumaric acid, and available as SPAR II® from a number of sources such as Atlas Chemical Company. They are also described in the Japanese Laid Open Patents. In addition, they are described in U.S. Pat. 4,533,614, and more specifically, U.S. Pat. 4,957,774 and 4,533,614 linear polyester resins comprised of dodecyl succinic anhydride, terephthalic acid, alkyloxylated bisphenol A and trimellitic anhydride as chain extenders. Additionally, in U.S. Pat. 4,940,644, U.S. Pat. No. 5,047,305, U.S. Pat. No. 4,049,447, and Canadian Patent 1,032,804 discloses a linear polyester comprised of an amorphous aromatic polyester derived from an arylene radical and diol, and specifically resins such as poly (neopentyl terephthalate) comprised of the radical terephthalate and neopentyl glycol. Also, in U.S. Pat. No. 4,525,445 describes an organic pigment comprised of a linear polyester derived from fumaric acid, isophthalic acid and propoxylated dysphenol. In addition, other organic pigment compositions containing linear polyester resins, such as those described in U.S. Pat. 4,968,575 a linear polyester blocked with tar-to-tar compound; U.S. Pat. 5,004,664 a linear polyester prepared from the ring-opening polymerization of cyclic monomers; U.S. Patent 5,057,392 a mixture of reams comprised of crystalline and amorphous polyesters; and U.S. Patents 4,543,313 and 4,891,293 where linear thermotropic liquid crystalline polyester resins are described, the descriptions of which are hereby incorporated by reference in their entirety. Other U.S. Patents of interest describing, for example, linear polyesters are U.S. Pat. 4,052,325; 3,998,747 3,909,482; 4,4049,447; 4,288,516; 4,140,644; 4,489,150 4,478,423; 4,451,837; 4,446,302; 4,416,965; 4,866,158 5,153,301; 5,116,713; 5,043,242; 5,045,224; 5,049; 646 5,102,762; 5,110,977 and 4,837,394. Compositions containing polyester resins modified with a polybasic carboxylic acid are also known and are described in Japanese Laid Open Nos. 44836 (1975); 3753 (1982) and 109875 (1982); and also in U.S. Pat. 3,681,106, and more specifically branched or crosslinked polyesters derived from polyvalent acids or alcohols are illustrated in U.S. Pat. 4,298,672; 4,863,825; 4,863,824; 4,845,006 4,814,249; 4,693,952; 4,657,837; 5,143,809; 5,057,596 4,988,794; 4,981,939; 4,980,448; 4,960,664; 4,933,252 4,931,370; 4,917,983 and 4,973,539. In some of the aforementioned prior art references, polyester resins are described wherein the end groups are an acid group, where the acid indices are reported, and / or where hydroxyl groups are present.
Sat * '4.
Polyester-based resins comprised of hydrophilic portions such as alkyl sulfonate groups are known, and are described in U.S. Pat. 5,348,832; 5,593,807; 5,604,076; 5,648,193; 5,658,704; 5,660,965; 5,684,063; and 5,698,223, the disclosure of which is hereby incorporated by reference in its entirety. The polyester resins of the prior art, mentioned above, contain hydrophilic portions, preferably in an amount ranging from about 2 to about 7.5 weight percent resin, and are used so that dissipation, or emulsification, is obtained. of the resin in water. To prevent the melter roller from deviating and increasing the latitude of the organic pigments in the melter, various modifications to the organic pigment compositions have been proposed. For example, U.S. Pat. 4,513,074 discloses adding waxes, such as low molecular weight polyethylene, polypropylene, to organic pigments to increase their release properties. To sufficiently prevent the deviation, however considerable amounts of such materials may be required, resulting in the damaging effect of agglomeration of the organic pigment, degradation in the free-flowing properties, and destabilization of the charging properties.
In U.S. Pat. 5,168,028 illustrate a negatively chargeable organic pigment for developing electrostatic latent images, comprising a binder resin, a coloring agent and a charge control agent which comprises a quaternary ammonium salt comprising fluorine. In U.S. Pat. 5,324,613 organic pigments are illustrated with hydroxy bis (3,5-butyl dithioneal salicylic acid) aluminate monohydrate; U.S. Pat. 4,656,112 organic pigments with a zinc complex (E-84) of tertiary 3,5-butyl salicylate; and U.S. Pat. 4,845,003 organic pigments with hydroxy carboxylic acid. The descriptions of each of the aforementioned Patents are incorporated herein by reference in their entirety.
BRIEF DESCRIPTION OF THE INVENTION It is a feature of the present invention that it provides organic pigment and developer compositions, wherein the binder resin of the organic polyester pigment contains hydrophilic groups and hydrophobic end groups. Another feature of the present invention is that it provides negatively charged organic pigment compositions useful for developing latent electrostatic images, including color images.
Yet another feature of the present invention provides negatively charged or positively charged organic pigment compositions containing polyester with hydrophobic end groups such as a hydrocarbon or aromatic portion of about 4 carbon atoms to about 120 carbon atoms. Further, in a further feature of the present invention there are provided negatively charged organic pigment compositions containing polyester with hydrophilic portions or groups, such as an alkaline s of a sulfonate moiety such as sodium sulfonate, lithium sulfonate, sulfonate of potassium, beryllium sulfonate, masium sulfonate or barium sulfonate. Also, in another feature of the present invention, developer compositions are provided with negatively charged organic pigment particles, and carrier particles. Additionally, in a further feature of the present invention organic pigments are provided having triboelectric properties with low sensitivity to moisture such as, for example, from about 1.0 to about 2.5. In a further feature of the present invention, organic pigments with stability, such as, for example, from about 250,000 'to about 5,000,000 copies or impressions are provided in the 6180 printer of Xerox Corporation., and organic pigments with a rapid mixing time such as, for example, less than about 1 minute and preferably less than about 30 seconds, such as about 5 to about 30 seconds. Also, in another feature of the present invention organic pigments are provided which have triboelectric properties with low sensitivity to moisture, such as, for example, from about 1.0 to about 2.5, with desirable mixing properties of about 15 seconds to about 60 seconds. according to what is determined by the spectrograph, and preferably from about 15 to about 30 seconds. Further, in another feature of the present invention, organic pigments are provided which have triboelectric properties with low sensitivity to moisture with low minimum fixing temperatures such as from about 120 ° C to about 140 ° C. In another feature of the present invention organic pigments are provided with suitable triboelectric properties, low sensitivity to moisture, and wide latitude of fusion, such as from about 30 ° C to about 45 ° C. In another feature of the present invention there is provided a method for controlling the reproducibility of the degree of polymerization. In addition, in yet another feature of the present invention, organic pigment and developer compositions are provided that are useful in a variety of electrostatic imaging and printing processes, including color xerography, and wherein the mixing charge times are less than or equal to approximately 60 seconds. Those and other features of the present invention can be achieved in embodiments thereof by providing organic pigment compositions comprised of dye, such as pigment particles, and a polyester resin where the final groups are hydrophobic. The aspects of the present invention relate to an organic pigment composition comprised of a polyester resin with hydrophilic portions or groups and hydrophobic end groups, dye, optional wax, optional filler additive, and optional surface filler additives.; an organic pigment composition comprised of a polyester ream containing at least one hydrophilic group, at least one hydrophobic group, and dye; an organic pigment wherein the polyester resin is derived from at least one organic diol monomer, at least one organic diacid or diester monomer, and at least one monofunctional alcohol monomer or hydrophobic monofunctional acid, at least one alkali metal salt or alkaline earth of alkylene sulfonate, an arylene sulfonate diacid, or a diester monomer; an organic pigment composition containing a polyester resin of the formulas
p m where R is a hydrocarbon; X is arylene, an olefinic group or groups, an alkylene; R 'is alkyl or alkylene; m n represent the number of rm segments; S is a hydrophilic group, Y is equivalent to X or S, an organic pigment composition wherein R (for the polyester) is an alkylene; an organic pigment composition wherein R is an alkylene with from about 2 to about 20 carbon atoms; an organic pigment composition wherein the hydrocarbon possesses about 2 to about 22 carbon atoms; an organic pigment composition wherein the R of the polyester is cyclohexylene; the organic pigment composition wherein R is 1, -dimethylcyclohexylene; an organic pigment composition wherein the R of the polyester is ethylene, propylene, butylene or ethylene oxyethylene; an organic pigment composition wherein the arylene of X has from about 6 to about 30 carbon atoms; an organic pigment composition wherein the X of the polyester is phenylene; an organic pigment composition wherein X is phthalene; an organic pigment composition wherein X is terephthalene; an organic pigment composition wherein X is isophthalene; an organic pigment composition wherein the olefinic group of X has from about 2 to about 12 carbon atoms; an organic pigment composition wherein the olefinic group X is vinylene; an organic pigment composition wherein the olefinic group X is methylvinylene; an organic pigment composition wherein the alkylene of X possesses from about 2 to about 20 carbon atoms; an organic pigment composition wherein the alkylene of X is ethylene, propylene, butylene, pentylene or hexylene; an organic pigment composition wherein the alkyl of R 'contains from 1 to about 120 carbon atoms; an organic pigment composition wherein the R 'alkyl of the polyester contains from about 5 to about 30 carbon atoms; an organic pigment composition wherein the alkyl of R 'is hexyl, heptyl, octyl, lauryl, or stearyl; an organic pigment composition wherein the alkylene of R 'is polyethylene or polypropylene; an organic pigment composition wherein the polyester m is a number from about 20 to-about 2,000; an organic pigment composition wherein the polyester m is a number from about 50 to about 125; an organic pigment composition wherein the n of the polyester is a number from about 1 to about 100; an organic pigment composition wherein the n of the polyester is a number from about 50 to about 125; an organic pigment composition wherein the polyester m is a number from about 100 to about 500, n is a number from about 15 to about 25, where m is 20 times the value of n; an organic pigment composition wherein the S of the polyester is an alkaline earth metal salt of an arylene sulfonate; an organic pigment composition wherein S is an alkaline earth metal salt of an alkylene sulfonate; an organic pigment composition wherein S is an alkaline earth metal salt of an arylene sulfonate, wherein the metal is lithium, sodium, potassium, cesium, beryllium, magnesium, calcium or barium; an organic pigment composition wherein X is an alkaline earth metal salt of a phenylene sulfonate; an organic pigment composition wherein S is an alkali metal salt of isophthallene 5-sulfonate, terephthalene sulfonate, or alkylene sulfonate; an organic pigment composition wherein the R 'the X of the polyester are methylene, propylene, ethylene, butylene, pentylene, hexylene or ethylene; an organic pigment composition wherein the polyester resin is further comprised of an additional branching segment, p or q, or mixtures thereof, as illustrated by the formulas
Wherein R "is a trivalent aromatic or aliphatic radical with 3 to about 20 carbon atoms, and p and p represent the branching segment and are from about 0.1 to about 6 mole percent based on the initial diacid or diester used to prepare the resin, where the sum of p and q segments is 100 mole percent of the polyester resin, a composition of organic pigment where R "is trivalent derivative propane, butane, pentane, hexane, ciciohexano, heptane, octane, benzene, naphthalene or anthracene; an organic pigment composition wherein p and q are each from about 0.1 to about 6 mole percent based on the diacid or diester reagent selected for the preparation of the polyester; an organic pigment composition wherein the polyester resin is further comprised of an additional branching segment, r or s, or mixtures thereof as illustrated by the formulas
where R "is a multifunctional radical, and where the sum of the segments r and s is 100 mole percent of the polyester resin; an organic pigment composition wherein R "is a polyvalent or tetravalent aromatic or aliphatic radical with from about 3 to about 20 carbon atoms for the aliphatic, and from about 6 to about 30 for the aromatic; and r and s represent the branching segment and are from about 0.1 to about 6 mole percent based on the initial diacid or diester; an organic pigment composition wherein the hydrophobic groups of the polyester are final groups of poly (1,2-propylene-terephthalate-diethylene co-terephthalate) finally blocked with an alkyl group of stearyl or stearate, poly (1, 2-terephthalate) propylene-co-terephthalate of diethylene-co-terephthalate 1,1,1-trimethylene propane) finally blocked with an alkyl group of stearyl or stearate, poly (1, 2-propylene terephthalate) finally blocked with an alkyl group such as stearyl or stearate, poly (terephthalate 1, 2-propylene-co-diethylene terephthalate) finally blocked with an alkyl group or lauryl laurate, poly (1,2-propylene terephthalate-co-diethylene terephthalate) finally blocked with an alkyl group cetyl or palmitate, poly (terephthalate 1, 2-propylene-co-terephthalate diethylene) finally blocked with octoate, poly (terephthalate 1, 2-propylene-co-terephthalate diethylene) finally blocked with group alkyl or of the palmitate, stearyl, lauryl, palmitate, stearate or laurate; and mixtures thereof; a composition of organic pigment wherein the polyester S is an ionic salt of a difunctional monomer sulfonated where the ion is an alkali metal or alcal-inotérreo metal lithium, sodium, potassium, cesium, rubidium, magnesium, barium, calcium or beryllium, and sulfonated dysfunctional or moneno function is selected from the group consisting of dimethyl-5-sulfo isophthalate, dialkyl anhydride-sulfo- isophthalate-5-sulfo-l-4, 8-naphthalic acid, 4-sulfophthalic, 4- sulfofenil- 3, 5-dicarboximetoxibenceno, 6-sulfo-2-naphthyl-3, 5-dicarbomethoxybenzene, sulfoterephthalic acid, dimethyl-sulfo terephthalate, dialquilsulfo terephthalate, sulfo-ethanediol, 2-sulfo-propanediol, 2-sulfobutandiol, 3-sulfopentandiol, 2 -sulfo-hexandiol, 3-sulfo-2-methylpentanediol, sulfonate of N, N-bis (2-hydroxyethyl) -2-aminoethane, 2-sulfo-3, 3-dimethylpentanediol, sulfo-p-hydroxybenzoic acid and mixtures thereof, the same; an organic pigment composition wherein the polyester resin has a number average molecular weight of about 2,000 grams per mole to about 100,000 grams per mole, a weight average molecular weight of about 4,000 grams per mole to about 250,000 grams per mole, and a polydispersity of from about 1.8 to about 17; an organic pigment composition with a sensitivity to the relative humidity of the triboelectric charge of about 1.0 to about 2.8.; an organic pigment composition with a sensitivity to the relative humidity of the triboelectric charge of about 1 to about 2.5; an organic pigment composition wherein the additive that increases the charge was further included and is present in an amount of, for example, from about 0.05 to about 5 weight percent, and results in a positively or negatively charged organic pigment; an organic pigment composition wherein the additive which increases the charge was incorporated into the organic pigment, or is present on the surface of the organic pigment composition, and results in a positively or negatively charged organic pigment; an organic pigment composition further comprising a wax component with an average molecular weight of, for example, from about 1,000 to about 20,000; an organic pigment composition wherein the wax component is selected from the group consisting of polyethylene and polypropylene; an organic pigment composition further containing as external additives metal salts of a fatty acid, colloidal silicas, metal oxides, or mixtures thereof; an organic pigment composition wherein the colorant is carbon black, cyan, magenta, yellow, red, blue, green, brown, or mixtures thereof; a developer composition comprised of the organic pigment composition containing polyester and carrier particles; a method for forming images which comprises formulating a latent electrostatic image on a negatively charged photoreceptor, effecting the development thereof with the polyester containing organic pigment composition illustrated herein, and subsequently transferring the developed image to a suitable substrate; a process for the preparation of a polyester resin with at least one hydrophilic portion and at least one hydrophobic end group, and preferably two end groups, which comprises the polyesterification of a diester or diacid with a diol or mixtures of diols, a polycondensation catalyst, a polyfunctional reagent, and a monofunctional hydrophobic end group monomer; a process where the diester or diacid is a malonic acid, succinic acid, 2-methylsuccinic acid, 2,3-dimethyl succinic acid, dodecyl succinic acid, glutaric acid, adipic acid, 2-methyl adipic acid, pimelic acid, azelaic acid, acid sebasic, terephthalic acid, isophthalic acid, phthalic acid, 1,2-cyclohexanedioic acid, 1,3-cyclohexanedioic acid, 1,4-cyclohexanedioic acid, glutaric anhydride, succinic anhydride, dodecyl succinic anhydride, maleic anhydride, fumaric acid, maleic acid , itaconic acid, 2-methylitaconic acid, dialkyl esters, wherein the alkyl comprises from about one carbon atom to about f 5 carbon atoms and are diesters of malonic acid, succinic acid, 2-methyl succinic acid, 2,3-acid dimethylsuccinic acid, dodecyl succinic acid, glutaric acid, adipic acid, 2-methyl adipic acid, pimelic acid, azelaic acid, sebasic acid, acid tere phthalic acid, isophthalic acid, phthalic acid, 1,2-cyclohexanedioic acid, acid
1,3-cyclohexanedioic acid, 1,4-cyclohexanedioic acid, mixtures thereof; and diesters, or diacids which are optionally selected in effective amounts of about 45 to about 55 mole percent of the polyester resin; where the diol or glycol is diethylene glycol, ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 1 , 2-pentylene glycol, 1,3-pentylene glycol, 1,4-pentylene glycol,
1,5-pentylen glycol, 1,2-hexylene glycol, 1,3-hexylene glycol,
1,4-hexylene glycol, 1,5-hexylene glycol, 1,6-hexylene glycol, heptylene glycols, octylene glycols, decylene glycol, dodecylene glycol, 2,2-dimethyl propanediol, propoxylated bisphenol A, ethoxylated bisphenol A, 1, 4-c-clohexandiol, 1,3-cyclohexandil, 1,2-c-clohexandol, 1,2-cyclohexanedimethanol, or mixtures thereof; and glycols which are optionally selected in effective amounts of about 45 to about 55 mole percent of the polyester resin; where it is selected for the reaction of a catalyst of the polycondensation of tetraalkyl titanates, dialkyl tin oxide, tetraalkyl tin, alkyl tin oxide hydroxide, aluminum alkoxides, alkyl zinc, dialkyl zinc, zinc oxide, stannous oxide, or mixtures thereof, and catalysts which are optionally selected in effective amounts of about 0.01 mole percent to about 5 mole percent based on the initial diacid or diester used to prepare the resin, and where the monomer of the monofunctional hydrophobic end group is hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol and other alcohols derived from about 6 to about 24 carbon atoms, oleyl alcohol, linoleic alcohol, cinnamyl alcohol, substituted alcohols with alkyl such as 2-methylexanol, 2, 3, 3-trimethyl hexanol, 2-me t-loctanol and 3.7-dimethyl-l, 6-octadien-3-ol, and benzyl alcohol; monofunctional acids such as butyric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, stearic acid, lauric acid, palmitic acid, oleic acid, linoleic acid, cinnamic acid, higher alkylated acids derived from about 4 to about 24 carbon atoms, benzoic acid, naphthoic acid, or mixtures thereof; Y;'? TO -- ' ' . : 3 A'- - groups which are optionally present in effective amounts of about 0.1 mole percent to about 4 mole percent based on the initial diacid or diester used to prepare the resin; a process wherein the polycondensation is carried out at a temperature from about 165 ° C to about 190 ° C for a duration of about 360 minutes to about 8 hours, followed by the temperature increase from about 180 ° C to about 220 ° C and reducing the pressure of atmospheric pressure to about 0.1 millibars to about 100 millibars for a duration of about 60 minutes to about 720 minutes, followed by discharge of the polyester product and cooling to room temperature; an organic pigment composition further containing an additive that increases the charge of a quaternary ammonium compound; an organic pigment composition further containing a loading additive of hydroxy bis (3,5-butyl salicylic acid diter) monohydrate, aluminate, 3,5-butyl di-tertiary salicylate, an aluminum compound of a hydroxycarboxylic acid, acetyl pyridinium halide, or diesteryl dimethyl ammonium methyl sulfate, wherein the surface additives are comprised of metal salts of a fatty acid, colloidal silicas, metal oxides or mixtures thereof, and wherein each surface additive is present in an amount of about 0.1 to about 5 percent by weight; an organic pigment composition wherein in the portion or group is present on the polymer backbone, or is present as a pendant group; an organic pigment composition "wherein the polyester is generated from at least one multifunctional branching monomer; an organic pigment comprised of a polyester resin containing at least one hydrophilic segment, hydrophobic segments, and dye; an organic pigment that also contains a wax; an organic pigment that also contains surface additives; an organic pigment wherein the surface additives are comprised of silicas, metal oxides, fatty acid metal salts, or mixtures thereof; an organic pigment wherein each of the surface additives is present in an amount of about 0.5 to about 3 weight percent or parts; an organic pigment composition which also contains wax, additive to increase the filler and surface additives; an organic pigment where the R 'of the polyester represents the hydrophobic group, and S represents the hydrophilic group; an organic pigment where at least one is two for the final hydrophobic group; an organic pigment wherein at least one is from about 2 to about 10 for the hydrophilic portion; an organic pigment where at least 1 for the hydrophobic group is 4; and organic pigment compositions comprised of pigment or dye, and a polyester having chemically bonded thereto a hydrophilic portion such as an alkyl sulfonate, especially an alkaline earth metal such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium , calcium, barium or hydrophobic end groups, such as an alkyl portion comprised of a hydrocarbon, especially alkyl, preferably from about 4 carbon atoms to about 120 carbon atoms. Examples of polyester resins with hydrophobic end groups, preferably two, and hydrophilic groups that can be selected include polyesters with alkyl end groups of the formulas illustrated herein such as copoly (sodium salt of 1,2-propylene-5-) sulfoisophthalate) -copoly (1, 2-propylene-2-co-diethylene terephthalate terephthalate) finally blocked with stearate, copoly (sodium salt of 1,2-propylene-5-sulfoisophthalate) -copoly (terephthalate of 1, 2- propylene) finally blocked with stearate, copoly (sodium salt of 1, 2-propylene-5-sulfoisophthalate) -copoly (1, 2-propylene-co-diethylene terephthalate terephthalate) finally blocked with laurate, copoly (sodium salt of 1 , 2-propylene-5-sulfoisophthalate) -copoly (1, 2-propylene-co-diethylene terephthalate terephthalate) finally blocked with polyethylene, copoly (sodium salt of diethylene-5-sulfoisophthalate) -copoly (1, 2-terephthalate) -propylene-co-diethylene terephthalate) blocked finally with octoate, copoly (lithium salt of 1, 2-propylene-5-sulfoisophthalate) -copoly (1, 2-propylene-diethylene terephthalate terephthalate) finally blocked with a hexyl group, copoly (potassium salt of 1, 2-propylene-5-sulfoisophthalate) -poly (1, 2-propylene-diethylene terephthalate terephthalate) finally blocked with a dodecyl group, copoly (magnesium salt of 1,2-propylene-5-sulfoisophthalate) -co -poly (1, 2-propylene-diethylene-terephthalate terephthalate) finally blocked with a decyl group, copoly (sodium salt of 1,2-propylene-5-sulfoisophthalate) - copoly (1,2-propylene- terephthalate) diethylene co-terephthalate) finally blocked with a benzyl group, mixtures thereof, and the like; and polyesters which possess, for example, a number average molecular weight of about 2,000 grams per mole to about 100,000 or about 20,000 to about 75,000 grams per mole, a weight average molecular weight, or from about 25,000 to about 125,000 with about 4,000 grams per mole to approximately 250, 000 grams per mole, and a polydispersity of approximately 1.8 to approximately 17, all measured by gel permeation chromatography. The polyester resin with the hydrophilic portions and the hydrophobic end groups selected for the organic pigment and developer compositions of the present invention, such as copoly (sodium salt of 1,2-propylene-5-sulfoisophthalate) -copoly (terephthalate 1,2-propylene-co-diethylene terephthalate) finally blocked with a final polyethylene group of approximately 45 carbon atoms, can be prepared by charging a Parr 1-liter reactor equipped with a mechanical stirrer and a side condenser, with a mixture from about 0.9 to about 0.095 mol of diester, such as dimethyl terephthalate, from about 0.025 to about 0.05 mol of sulfonate monomer, such as the sodium salt of dimethyl-5-sulfo-isophthalate, from about 1.75 moles to about 1.85. moles of a diol, such as 1,2-propandiol or diethylene glycol or a mixture of the diols, containing from about 0.15 to about 0.3 mol of diethylene glycol, from about 0.01 to about US Pat. No. 4,883,736, the disclosure of which is hereby fully incorporated by reference (available from Petrolite Chemicals), and from about 0.001 mole to about 0.05 of a condensation catalyst such as the butyl tin oxide hydroxide. The reactor is subsequently heated, for example, to 170 ° C for a suitable duration of, for example, about 360 minutes to about 720 minutes with stirring at, for example, about 10 revolutions per minute to about 200 revolutions per minute. During this time, from about 1.7 moles to about 1.9 moles of methanol product can be collected through the condenser. The temperature of the reactor is then raised to about 220 ° C and the pressure is reduced to about 1 Torr over the period from about 2 hours to about 3 hours. The polymeric resin comprised of copoly (sodium salt of 1,2-propylene-5-sulfoisophthalate) -poly (1,2-propylene-diethylene co-terephthalate terephthalate) finally blocked with a polyethylene group of about 45 carbon atoms, it is then discharged through the bottom of the reactor and collected at room temperature. The organic pigments prepared with the polyester resins of the present invention can be obtained by mixing and heating the polyester resin particles such as copoly (1, 2-propylene-5-sulfoisophthalate potassium salt) -poly (1, 2-terephthalate) propylene-co-diethylene terephthalate) finally blocked with a polyethylene group of about 45 carbon atoms, and dye particles such as magnetites, carbon black or mixtures thereof, and preferably from about 0.20 percent to about 5%. percent additives to increase the optional fillers, or mixtures of filler additives, and optionally wax in a melt mixing device, such as the ZSK53 extruder available from Werner Pfleiderer. After cooling, the composition of the organic pigment is subjected to grinding using, for example, a Sturtevant micronizer for the purpose of achieving organic pigment particles with an average diameter and a volume of less than about 25 microns, and preferably about 6 to approximately 12 microns, as determined by a Coulter Counter. The organic pigment particles can be classified using, for example, a Donaldson Model B classifier for the purpose of removing fine particles, ie particles of organic pigment of at least about 4 microns in average diameter in volume. Specific examples of diols used in the preparation of the polyesters of the present invention include diols or glycols such as ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 1,2-pentylene glycol, 1,3-pentylene glycol, 1,4-Pentylene glycol, 1,5-pentylene glycol, 1,2-hexylene glycol, 1,3-hexylene glycol, 1,4-hexylene glycol, 1,5-hexylene glycol, 1,6-hexylene glycol, heptylene glycols, octylene glycols, decylene glycols, dodecylene glycols, 2,2-dimethyl propandyl, propoxylated bisphenol A, ethoxylated bisphenol A, 1-cyclohexanediol, 1,3-cyclohexanediol, 1,2-cyclohexanediol, 1,2-cyclohexanedimethanol , mixtures thereof, and the like; and those glycols are employed in various effective amounts of, for example, from about 45 to about 55 mole percent of the polyester product resin. Specific examples of diacids or diesters used in the preparation of the polyesters include malonic acid, succinic acid, 2-methylsuccinic acid, 2,3-dimethyl succinic acid, dodecyl succinic acid, glutaric acid, adipic acid, 2-methyladic acid, acid pimelic acid, azelaic acid, sebacic acid, terephthalic acid, isophthalic acid, phthalic acid, 1,2-cyclohexanedioic acid, 1,3-cyclohexanedioic acid, 1,4-cyclohexanedioic acid, glutaric anhydride, succinic anhydride, dodecyl succinic anhydride, anhydride maleic, fumaric acid, maleic acid, itaconic acid, 2-methyl itaconic acid, and dialkyl esters of those diacids and dianhydrides, wherein the alkyl groups of the dialkyl ester are from one carbon atom to about 5 carbon atoms and mixtures thereof , and the like, and component which is employed, for example, in amounts of about 45 to about 55 mole percent. e the res a. Examples of polycondensation catalysts include tetraalkyl titanates, dicalkyltin oxide such as dibutyltin oxide, tetraalkyltin such as dibutyltin dilaurate, dialkyltin hydroxide, such as butyltin hydroxide, aluminum alkoxides, zinc alkyl , dialkyl zinc, zinc oxide, stannous oxide, or mixtures thereof; and catalysts which are selected in effective amounts of about 0.01 mole percent to about 5 mole percent based on the diacid or diester used to generate the polyester resin. The monofunctional hydrophobic monomers that can be used for the preparation of the polyesters include monofunctional alcohols such as hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, and other alcohols, such as those derived from components with from about 6 to about 24 carbon atoms, oleyl alcohol, linoleic alcohol, cinnamyl alcohol, alkyl-substituted alcohols, such as 2-methylhexanol, 2,3,3-trimethylhexanol, 2-methyloctanol, , 7-dimethyl-l, 6-octadien-3-ol and the like, hydrophobic aromatic monomers such as benzyl alcohol, monofunctional acids such as hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, stearic acid, acid lauric, palmitic acid, oleic acid, linoleic acid, cinnamic acid, and other alkyl acids, polyethylene-alcohols or propylene alcohols such as Unilin 350, Unilin 550, Unilin 700 and the like, such as those derived from components with from about 20 to about 120 carbon atoms; and monomers which may be selected in effective amounts of about 0.1 mole percent to about 4.0 mole percent based on the initial diacid or diester used to make the resin. Examples of hydrophilic monomers, which can be used for the preparation of the polyester resin, include the ionic salts of dysfunctional monomers suifonados where the ion is an alkaline or alkaline earth metal such as lithium, sodium, potassium, cesium, rubidium, magnesium , barium, calcium or beryllium and the like, and the sulfonated dysfunctional moiety is selected from the group including dimethyl-5-sulfo-isophthalate, dialkyl-5-sulfoisophthalate-4-sulfo-1, 8-naphthalic anhydride, 4-sulphonic acid phthalic, 4-sulfophenyl-3, 5-dicarbomethoxybenzene, 6-sulfo-2-naphthyl-3, 5-dicarbomethoxybenzene, sulfo-terephthalic acid, dimethyl-sulfo-terephthalate, dialkyl-sulfo-terephthalate, sulfo-ethanediol, 2-sulfo -propanediol, 2-sulfo-butanediol, 3-sulfopentanediol, 2-sulfo-hexandiol, 3-sulfo-2-methylpentanediol, sulfonate of N, N-bis (2-hydroxyethyl) -2-aminoethane, 2-sulfo-3, 3-dimethylpentanediol, sulfo-p-hydroxybenzoic acid, mixtures of 16 'and the same and the like. Hydrophilic amounts of, for example, from about 0.1 to about 2 weight percent of the resin can be selected. Additionally, crosslinking or branching agents may be used, such as trifunctional or multifunctional monomers, agents which usually increase the molecular weight and polydispersity of the polyester, and agents which are selected from the group consisting of glycerol, trimethylol ethane, trimethylol propane, pentaerythritol, sorbitol, diglycerol, trimellitic acid, trimellitic anhydride, pyromellitic acid, pyromellitic anhydride, 1,2-cyclohexanetricarboxylic acid, 2, 5, 7-naphthalenetricarboxylic acid, 1,2,4-butanetricarboxylic acid, mixtures thereof, and Similar; and agents which can be selected in effective amounts of about 0.1 mole percent to about 6.0 mole percent based on the initial diacid or diester used to make the resin. Numerous well-known suitable colorants, such as pigments or dyes, can be selected, such as the colorant for the organic pigment including, for example, cyano, magenta, yellow, ro, blue, green, carbon black such as REGAL 330®, dye of nigrosine, aniline blue, phthalocyanamines, magnetite, or mixtures thereof. A number of carbon black available from, for example, Cabot Corporation can be selected. The dye, which is preferably carbon black, should be present in an amount sufficient to color the organic pigment composition. Generally, the colorant is present in amounts of about 1 weight percent to about 20 weight percent, and preferably about 2 to about 10 weight percent based on the total weight of the organic pigment composition, and where the total of all the components of the organic pigment is approximately 100 percent. The colorant includes dyes, pigments, mixtures thereof, mixtures of pigments, mixtures of dyes, and other suitable dyes that will impart a desired color to the organic pigment. Examples of dye include known suitable dyes, such as food dyes. When the dye particles are comprised of magnetites, thereby allowing organic single-component magnetic pigments in some cases, which are a mixture of iron oxides (FeO * Fe20) which include
those commercially available as MAPICO BLACK® are present in the organic pigment composition in an amount of about 10 percent by weight to about 80 percent by weight, and preferably in an amount of about 10 percent by weight. weight up to about 50 weight percent. The blends of carbon black and magnetite are from about 1 to about 15 weight percent of carbon black, and preferably from about 2 to about 6 weight percent of carbon black, and magnetite, such as MALPICO BLACK®, in an amount of, for example, from about 5 to about 60 and preferably from about 10 to about 50 weight percent can be selected. Examples of filler additive include those illustrated in U.S. Patent 4,338,390, the disclosure of which is hereby incorporated by reference in its entirety, additives which preferably impart a positive charge to the organic pigment composition; alkyl pyridinium compounds such as those described in U.S. Patent 4,298,672, the disclosure of which is hereby incorporated by reference in its entirety, charge control additives such as those illustrated in U.S. Patent 3,944,493; 4,007,293; 4,079,014; 4,394,430 and 4,560,635, which illustrate an organic pigment with a filler additive of distearyl methyl ammonium sulfate, bisulphates, silicas and other known organic pigment loading additives. Negatively charged additives, such as zinc or aluminum complexes, such as the aluminum compound of a hydroxycarboxylic acid (BONTRON E-88® from Orient Chemical Company), the zinc complex of 3,5-butyl salicylate can also be selected. diteriarium (BONTRON E-84® from East Chemical Company) and hydroxy bis (3,5-butyl salicylic acid diter) monohydrate (Alohas), and the like. Compatibilizers may be included in the organic pigment compositions of the present invention, such as those illustrated in U.S. Pat. 5,229,242, the disclosure of which is hereby incorporated herein by reference, waxes, or mixtures thereof, such as polypropylenes and polyethylenes such as the commercial EPOLENE N-15MR available from Eastman Chemical Products, Inc., VISCOL 550-PMR, a polypropylene low molecular weight molecular weight available from Sanyo Kasei KK, and similar materials. It is believed that the commercially available polyethylenes selected have a molecular weight Mw of from about 1,000 to about 3,000, such as those obtainable from Petrolite Corporation, although it is believed that the commercially available polypropylenes used for the organic pigment compositions of the present invention possess a weight molecular M from about 4,000 to about 5,000. Many of the alkylanes such as the polyethylene and polypropylene compositions are illustrated in British Patent No. 1,442,835, the disclosure of which is hereby incorporated by reference in its entirety. The wax is present in the organic pigment composition of the present invention in various amounts; Generally wax is present in the organic pigment composition in an amount of about 1 weight percent to about 15 weight percent, and preferably in an amount of about 2 weight percent to about 10 percent in weigh. Organic pigment additives, such as external additive particles including additives to aid flow, additives which are usually present on the surface thereof can also be admixed with the organic pigment compositions of the present invention. Examples of such additives include metal oxides, such as aluminum oxide, titanium oxide, tin oxide, cerium oxide and mixtures thereof, and the like, colloidal fumed silicas, such as AEROSIL®, or Cabosil®, coated silicas, as a reference, for example, U.S. Patent Application Ser. Serial No. 08 / 131,188 and U.S. Patent Application. No. 08 / 132,623, the descriptions of which are hereby incorporated by reference in their entirety, metal salts and metal salts of fatty acids, including zinc stearate, magnesium stearate, polymeric components such as polyvinylidene fluoride which can be obtained from ATOCHEM North America, Inc, polytetrafluoroethylene available from ICI Advanced Materials, or polymeric microspheres from 0.1 to 2.0 microns, such as those available from Nippon Paint, Osaka, Japan, and mixtures thereof, additives which are each generally present in an amount of about 0.1 weight percent to about 5 weight percent, and preferably in an amount of about 0.1 weight percent to about 3 weight percent. A number of organic pigment additives are illustrated in U.S. Pat. 3,590,000 and 3,800,588, the descriptions of which are fully incorporated herein by reference. In addition to the present invention, colloidal silicas, such as AEROSIL®, can be surface treated with known filler additives, such as DDAMS (distearyldimethyl ammonium methyl sulfate), in an amount of about 1 to about 30 per cent. percent by weight and preferably 10 percent by weight, followed by the addition thereof to the organic pigment in an amount of 0.1 to 10, and preferably 0.1 to 1 percent by weight. Covered within the scope of the present invention are organic colored pigment and developer compositions comprised of organic pigment polyester resin particles, and as colorants red, blue, green, brown, magenta, cyan and / or yellow particles, as well as mixtures from the same. More specifically, with respect to the generation of color images, illustrative examples of magentas that can be selected include, for example, quinacridone substituted with dimethyl in positions 2.9 identified in the Color index as Cl 73915, Pigment Red 122, anthraquinone dye identified in the Color Index as Cl 60710, Disperse Red Cl 15, diazo dye identified in the Color Index as Cl 26050, Red Solvent Cl 19, and the like; examples of cians that can be selected include copper tetra-4- (octadecylsulfonamido) phthalocyanine, copper phthalocyanine pigment beta in the Color Index as Blue Pigment Cl 74160 15.3 and Anthratren Blue, identified in the Color Index as Cl 69810, Special Blue X-2137, and the like; and illustrative examples of yellows that can be selected are diarylide yellow, 3, 3-dichlorobenzidene, acetoacetanides, a monoazo pigment identified in the Color Index as Cl 12700, Solvent Yellow 16, nitrophenyl amino sulfonamide identified in the Color Index as Yellow Foron SE / GLN, Scattered Yellow Cl 33, 2, 5-dimethoxy-4-sulfanilido phenylazo-4'-chloro-2,5-dimethoxy acetanilide, and Permanent Yellow FGL. These dyes are incorporated into the organic pigment composition in various suitable effective forms such as from about 2 weight percent to about 15 weight percent calculated on the weight of the organic pigment resin particles. For the formulation of the developer compositions, they are mixed with the carrier components of the organic pigment particles, particularly those which are capable of triboelectrically assuming a polarity opposite to that of the organic pigment composition. Accordingly, the carrier particles of the present invention are selected to be of a negative or positive polarity by allowing the organic pigment particles, which are oppositely charged, to adhere to and around the carrier particles. Illustrative examples of the carrier particles include iron powder, steel, nickel, iron, ferrites, include copper and zinc ferrites, strontium ferrites, and the like. Additionally they can be selected as nickel milling carrier particles according to that illustrated in U.S. Pat. 3,847,604, the description of which is fully incorporated herein by reference. The selected carrier particles can be used with or without a coating, the coating generally contains styrene terpolymers, < methyl methacrylate, and a silane, such as triethoxysilane, as reference U.S. Pat. 3,526,533 and 3,467,634, the descriptions of which are hereby fully incorporated by reference;
polymethyl methacrylates, other known coatings; and similar. The carrier particles may also be included in the coating, which coating may be / present in the embodiments in an amount of from about 0.1 to about 3 weight percent, conductive substances, such as carbon black, in an amount of, per example, about 5 to about 30 weight percent. Polymeric coatings not very close to the triboelectric series can also be selected, as reference U.S. Pat. 4,937,166 and 4,935,326 the descriptions of which are fully incorporated herein by reference, including, for example, KYNAR® and polymethylmethacrylate mixtures such as 40/60. The coating weights may vary as indicated herein, generally, however, from about 0.3 to about 2, and preferably from about 0.5 to about 1.5 weight percent, of coating are selected. In addition, the diameter of the carrier particles, preferably spherical in shape, is generally from about 35 microns to about 1,000, and preferably from about 50 to about 200 microns in diameter, thereby enabling them, for example, to possess sufficient density and inertia to avoid 5S adhesion to electrostatic images during the development process. The carrier component can be mixed with the organic pigment composition in various suitable combinations, such as from about 1 to 5 parts by organic pigment "up to about 100 parts up to about 200 parts by weight of carrier, selected. of the present invention can be selected for use in electrostatic image forming apparatus containing photoconductive imaging members therein, such as those illustrated in US Patents 5,534,376, 5,456,998, 5,466,796, 5,563,261, 5,645,965, metal phthalocyanines, metal-free phthalocyamins, perylenes, titanyl phthalocyanines, and the like Thus, the organic pigment and developer compositions of the present invention can be used with stratified photoreceptors that are capable of being negatively charged, or positively, such as those written in US Patents 4,265,990; 4,585,884; 4,584,253; 4,563,408, the descriptions of which are fully incorporated herein by reference. Illustrative examples of inorganic photoreceptors that can be selected for imaging and printing processes include selenium; ST selenium alloys, such as selenium-arsenic, selenium-tellurium and the like; selenium substances adulterated with halogen; and selenium alloys adulterated with halogen. Other suitable photoreceptor or photoconductor image forming members can be selected. The organic pigment compositions are usually distributed and further classified for preparation to allow organic pigment particles with a preferred average diameter of about 5 to about 25 microns, and more preferably about 6 to about 12 microns. Also, the organic pigment compositions of the present invention preferably have a triboelectric charge of about 5 to 40 microcoulombs per gram in modalities thereof as determined by the known charge spectrograph. The mixing times for the organic pigments of the present invention are preferably from about 15 seconds to 1 minute, and more specifically from about 15 to about 30 seconds in modalities thereof as determined by the known charge spectrograph. These organic pigment compositions with rapid mixing characteristics allow, for example, the development of latent electrostatic images in electrophotographic imaging apparatuses, with the images revealed having no substantial background deposits therein, even at high pigment distribution speeds. organic in some cases, for example exceeding 20 grams per minute; and further, such organic pigment compositions can be selected for high-speed electrophotographic apparatuses, ie those exceeding 70 copies per minute. The weight percent in the modalities refers to the total amount of components, especially solids, divided into the specific component and multiplied by 100. For example, the weight percent of colorant, such as the pigment can be calculated by subtracting the amount of pigment of the amount of pigment and resin and dividing the result by the amount of resin and pigment, and then multiplying by 100. The following Examples are provided to better define various aspects of the present invention, it should be noted that those Examples are intended to illustrate and do not limit the scope of the present invention. The parts and percentages are by weight unless otherwise indicated.
EXAMPLE I Copolymer (1,2-propylene-co-diethylene terephthalate) -copoly (1,2-propylene-co-5-sulfo-isophthalate diethylene-5-sulfo-isophthalate) finally blocked with polyethylene, derivative of dimethyl terephthalate, 2 mole percent by weight of Unilin 700, and 1 mole percent by weight of sodium salt of dimethyl 5-sulfoisophthalate, was prepared as follows. A 2-liter Parr reactor equipped with a lower drain valve, double turbine agitator and distillation receiver with a cold water condenser was charged with 690 grams of dimethyl terephthalate, 8.6 grams of sodium salt of 5-sulfo isophthalate Dimethyl, 460 grams of 1,2-propanediol, 113 grams of diethylene glycol, 24.6 grams of Unilin 700 obtained from Petrolite, refer for example to US Pat. No. 4,883,736, the disclosure of which is hereby incorporated by reference, and 1.6 grams of butyl tin oxide catalyst obtained as FASCAT 4100MR from Elf Atochem North America, Inc. The reactor was then heated to 165 ° C with stirring at 150 revolutions per minute and then heated to 200 ° C for a duration of 6 hours, where a by-product of methanol (228 grams) was collected via the distillation receiver to a receiver, and by-product which was comprised of approximately 98 volume percent methane ol and 2 volume percent of 1,2-propandiol as measured by the ABBE refractometer available from American Optical Corporation. The reactor mixture was then maintained at 200 ° C, and the pressure was reduced from the atmospheric pressure to approximately 0.2 Torr for a duration of about 3 hours. During this time, 286.5 grams of glycol with approximately 97 volume percent 1,2-propanediol and 3 volume percent methanol were also collected at approximately 286.5 grams as measured by the ABBE refractometer. The reactor was then purged with nitrogen at atmospheric pressure and the polymer discharged through the bottom drainage into a vessel cooled with dry ice to give 1.13 kilograms of copoly (1,2-propylene-diethylene terephthalate-copol-terephthalate) ( 5-sulfo-1, 2-propylene-co-5-sulfo-isophthalate diethylene softalate) finally blocked with polyethylene derived from Unil 700. The glass transition temperature of the resulting resin product above was measured to be 59 ° C ( initially) using the Differential Scanning Calorimeter 910 available from El DuPont operating at a heating rate of 10 ° C per minute. The number average molecular weight of the resin of the polyester product was measured to be 4,100 grams per mole and the weight average molecular weight was measured to be 11,000 grams per mole using tetrahydrofuran as the solvent and obtained with the gel permeation chromatograph. 700 Satellite WISP available from Waters Company equipped with a styrogel column. For the polyester resin of this Example, a softening point of 130.9 ° C was obtained using the Mettler Flow Tester. It was found that the acid number of the polyester resin was 2.0 milliequivalents per gram of potassium hydroxide.
EXAMPLE II The copoly (1,2-propylene-diethylene-terephthalate terephthalate) -copoly (diethylene 1,2-propylene-5-sulfo-β-sophone-softalate 5-sulfo-isophthalate) finally blocked with polyethylene, derivative of terephthalic acid, 2 mole percent by weight of Unilin 700, and 1 mole percent by weight of sodium salt of dimethyl 5-sulfoisophthalate, was prepared as follows. A 2 liter Parr reactor equipped with a lower drain valve, double turbine agitator and distillation receiver with a cold water condenser was charged with 589 grams of terephthalic acid, 8.6 grams of sodium salt of 5-sulfo-? Softalate of dimethyl, 484 grams of 1,2-propandiol, 94.5 grams of diethylene glycol, 24.6 grams of Unil 700, and 1.7 grams of butyl tin oxide catalyst obtained as FASCAT 4100MR from Elf Atochem North America, Inc. The reactor was then pressurized to 300 kilopascals with nitrogen, and heated to 240 ° C with stirring at 150 revolutions per minute for a duration of 4 hours, where the reactor pressure was maintained from about 287 to about 314 kilopascals, and where the aqueous byproduct (93 grams) was collected via the distillation receiver into a vessel, and byproduct which was comprised of approximately 99 volume percent water and 1 volume percent 1,2-propandiol according to measured by the ABBE refractometer available from American Optical Corporation. The reaction temperature was then lowered to about 205 ° C, and the pressure was reduced to atmospheric pressure (about 101 kilopascals) for a duration of about 1 hour. During this time, approximately 5 grams of water were also collected. The reactor pressure was then reduced from atmospheric pressure to about 6 Torr for a period of 3 hours and where approximately 150 grams of glycol were collected. The polymeric product was then discharged through the lower drain onto a vessel cooled with dry ice to produce 1.05 kilograms of copoly (1, 2-propylene-diethylene-terephthalate terephthalate) -copoly (5-sulfo-isophthalate of 1). , 2-propylene-co-5-sulfo-isophthalate of diethylene) finally blocked with polyethylene derived from Unilm 700. The vitreous transition temperature of the resulting resin product was measured above was 62.9 ° C
(initially) using the Differential Scanning Calorimeter 910 available from E.l. DuPont operating at a heating rate of 10 ° C per minute. The number average molecular weight of the resin of the polyester product was measured, was 5.600 grams per mole and the weight average molecular weight was measured, was 12.700 grams per mole using tetrahydrofuran as the solvent and obtained with the permeation chromatograph in gel 700 Satellite WISP available from Waters Company equipped with a styrogel column. For the polyester resin of this Example, a softening point of 130.4 ° C was obtained using the Mettler Flow Tester. It was found that the acid number of the product of the polyester resin was 1.9 milliequivalents per gram of potassium hydroxide.
EXAMPLE III Copolymer (1,2-propylene-co-diethylene terephthalate) -copoly (diethylene 1,2-propylene-co-5-sulfo-isophthalate 5-sulfo-isophthalate) finally blocked with polyethylene, derivative of terephthalic acid, 2 mole percent by weight of Unilin 700, and 2 mole percent by weight of sodium salt of dimethyl 5-sulfoisophthalate, was prepared as follows. A 2 liter Parr reactor equipped with a lower drain valve, double turbine agitator and distillation receiver with a cold water condenser was charged with 583 grams of terephthalic acid, 17.2 grams of sodium salt of 5-sulfo-isophthalate from dimethyl, 484 grams of 1,2-propanediol, 94.5 grams of diethylene glycol, 24.6 grams of Unilin 700, and 1.7 grams of butyl tin oxide catalyst obtained as FASCAT 4100MR from Elf Atochem North America, Inc. The reactor was then pressurized to 300 kilopascals with nitrogen, and heated to 240 ° C with stirring at 150 revolutions per minute for a duration of 4 hours, where the reactor pressure remained from about 287 to about 314 kilopascals, and where the aqueous byproduct (93 grams) it was collected via the distillation receiver into a vessel, and was comprised of approximately 99 volume percent water and 1 volume percent 1,2-propanediol according to the edited by the ABBE refractometer available from American Optical Corporation. The reaction temperature was then lowered to about 205 ° C, and the pressure was reduced to atmospheric pressure (about 101 kilopascals) for a duration of about 1 hour. During this time, approximately 5 grams of water were also collected. The reactor pressure was then reduced from atmospheric pressure to about 6 Torr for a period of 3 hours and where approximately 150 grams of glycol were collected. The polymeric product was then discharged through the lower drain onto a vessel cooled with dry ice to produce 1.05 kilograms of copoly (1, 2-propylene-diethylene co-terephthalate terephthalate) -copoly (5-sulfo-isophthalate of 1 , 2-propylene-co-5-sulfo-isophthalate of diethylene) finally blocked with polyethylene derived from Unilin 700. The vitreous transition temperature of the resulting resin product was measured above, was 55.7 ° C (initially) using the Calorimeter of Differential Exploration 910 available from El DuPont operating at a heating rate of 10 ° C per minute. The number average molecular weight of the resin of the polyester product was measured, was 3,300 grams per mole and the weight average molecular weight was measured, was 10,500 grams per mole using tetrahydrofuran as the solvent and obtained with the permeation chromatograph in gel 700 Satellite WISP available from the Waters Company equipped with a styrogel column. For the polyester resin of this Example, a softening point of 134 ° C was obtained using the Mettler Flow Tester. It was found that the acid number of the product of the polyester resin was 2.5 milliequivalents per gram of potassium hydroxide.
EXAMPLE IV Copoly (terephthalate of 1, Diethylene 2-propylene-co-terephthalate) -copoly (1,2-propylene-co-5-sulfo-isophthalate diethylene) -3-poly (trimethylolpropane terephthalate) blocked with polyethylene , derivative of terephthalic acid, 2 mole percent by weight of Unilin 700, and 1 mole percent by weight of sodium salt of dimethyl 5-sulfoisophthalate, and 0.75 mole percent of trimethylolpropane as branching agent was prepared as follows . A 2-liter Parr reactor equipped with a lower drain valve, double turbine agitator and distillation receiver with a cold water condenser was charged with 778.7 grams of terephthalic acid, 11.4 grams of sodium salt of 5-sulfo-isophthalate from dimethyl, 638.9 grams of 1,2-propanediol, 124.7 grams of diethylene glycol, 32.5 grams of Unilin 700, 12.5 grams of trimethylolpropane, and 1.7 of butyl tin oxide catalyst obtained as FASCAT 4100MR from Elf Atochem North America, Inc. The reactor was then pressurized to 300 kilopascals with nitrogen, and heated to 240 ° C with stirring at 150 revolutions per minute for a duration of 4 hours, where the reactor pressure was maintained from about 287 to about 314 kilopascals, and where the aqueous by-product (179 grams) was collected via the distillation receiver into a vessel, and was comprised of approximately 99 volume percent water and 1 volume percent 1 , 2-propanediol according to what was measured by the ABBE refractometer available from American Optical Corporation. The reaction temperature was then lowered to about 205 ° C, and the pressure was reduced to atmospheric pressure (about 101 kilopascals) for a duration of about 1 hour. During this time, approximately 6 grams of water were also collected. The reactor pressure was then reduced from atmospheric pressure to about 6 Torr for a period of 3 hours and where approximately 264.5 grams of glycol was collected. The polymeric product was then discharged through the lower drain onto a vessel cooled with dry ice to produce 1.03 kilograms of copoly (1, 2-propylene-diethylene co-terephthalate) -copoly (5-sulfo-isophthalate of 1). , Diethylene 2-propylene-co-5-sulfo-isophthalate) -copoly (trimethylolpropane terephthalate) finally blocked with polyethylene derived from Unilin 700. The vitreous transition temperature of the resulting resin product above was measured to be 58.2 ° C. (initially) using the Differential Scan Calorimeter 910 available from El DuPont operating at a heating rate of 10 ° C per minute. The number average molecular weight of the resin of the polyester product was measured, was 3,500 grams per mole and the weight average molecular weight was measured, was 15,500 grams per mole using tetrahydrofuran as the solvent and obtained with the permeation chromatograph in gel 700 Satellite WISP € 7. available from Waters Company equipped with a styrogel column. For the polyester resin of this Example, a softening point of 132 ° C was obtained using the Mettler Flow Tester. It was found that the acid value of the product of the polyester resin was 2.2 milliequivalents per gram of potassium hydroxide.
EXAMPLE V Copolyol (1,2-propylene-diethylene-terephthalate terephthalate) -poly (diethylene 1,2-propylene-co-5-sulfo-isophthalate 5-sulfo-isophthalate) - copoly (t-methylpropane terephthalate) ) finally blocked with polyethylene, derivative of terephthalic acid, 2 mole percent by weight of Unil 700, and 1 mole percent by weight of sodium salt of dimethyl 5-sulfoisophthalate, and 1.5 mole percent of trimethylolpropane as an agent of Branch was prepared as follows. A 2-liter Parr reactor equipped with a lower drain valve, double turbine agitator and distillation receiver with a cold water condenser was charged with 778.7 grams of terephthalic acid, 11.4 grams of sodium salt of 5-sulfo-isophthalate dimethyl, 638.9 grams of 1,2-propanediol, 124.7 grams of diethylene glycol, 32.5 grams of Unilin 700, 25 grams of trimethylolpropane, and 1.7 of butyl tin oxide catalyst obtained as FASCAT 6 '8 4100MR from Elf Atochem North America, Inc. The reactor was then pressurized to 300 kilopascals with nitrogen, and heated to 240 ° C with stirring at 150 revolutions per minute for a duration of 4 hours, where the reactor pressure was maintained from about 287 to about 314 kilopascals, and where the aqueous byproduct (179 grams) was collected via the distillation receiver into a vessel, and was comprised of approximately 99 volume percent water and 1 volume percent n of 1,2-propandiol as measured by the ABBE refractometer available from American Optical Corporation. The reaction temperature was then lowered to about 205 ° C, and the pressure was reduced to atmospheric pressure (about 101 kilopascals) for a duration of about 1 hour. During this time, approximately 6 grams of water were also collected. The reactor pressure was then reduced from atmospheric pressure to about 6 Torr for a period of 3 hours and where approximately 264.5 grams of glycol was collected. The polymeric product was then discharged through the lower drain onto a vessel cooled with dry ice to produce 1.03 kilograms of copoly (1, 2-propylene-diethylene co-terephthalate) -copoly (5-sulfo-isophthalate of 1). , 2-propylene-co-5-sulfo-isophthalate diethylene) -copoly (trimethylolpropane terephthalate) finally blocked with polyethylene derived from Unilin 700. It was measured. the glass transition temperature of the resulting resin product above was 54.6 ° C (initially) using the Differential Scanning Calorimeter 910 available from E.l. DuPont operating at a heating rate of 10 ° C per minute. The number average molecular weight of the resin of the polyester product was measured, was 3,800 grams per mole and the weight average molecular weight was measured, was 18,900 grams per mole using tetrahydrofuran as the solvent and obtained with the permeation chromatograph in gel 700 Satellite WISP available from Waters Company equipped with a styrogel column. For the polyester resin of this Example, a softening point of 132 ° C was obtained using the Mettler Flow Tester. It was found that the Acid Index of the product of the polyester resin was 2.1 milliequivalents per gram of potassium hydroxide.
EXAMPLE VI Copolymer (1,2-propylene-co-diethylene terephthalate) -copoly (1,2-propylene-co-5-sulfo-isophthalate diethylene) -poly (trimethylolpropane terephthalate-5-sulfo-isophthalate) ) finally blocked with polyethylene, derivative of terephthalic acid, 2 mole percent by weight of Unilin 700, and 3 mole percent by weight of sodium salt of dimethyl 5-sulfo-isophthalate, and 1.5 mole percent of trimethylolpropane as an agent of Branch was prepared as follows. A 2 liter Parr reactor equipped with a lower drain valve, double turbine agitator and distillation receiver with a cold water condenser was charged with 754 grams of terephthalic acid, 34.2 grams of sodium salt of dimethyl 5-sulfoisophthalate, 638.9 grams of 1,2-propanediol, 124.7 grams of diethylene glycol, 32.5 grams of Unilin 700, 25 grams of trimethylolpropane, and 1.7 of butyl tin oxide catalyst obtained as FASCAT 4100MR from Elf Atoche North America, Inc. The reactor was then pressurized to 300 kilopascals with nitrogen, and heated to 240 ° C with stirring at 150 revolutions per minute for a duration of 4 hours, where the reactor pressure was maintained from about 287 to about 314 kilopascals, and where the aqueous byproduct (179 grams) was collected via the distillation receiver into a vessel, and was comprised of approximately 99 volume percent water and 1 volume percent 1, 2 -propandiol as measured by the ABBE refractometer available from American Optical Corporation. The reaction temperature was then lowered to about 205 ° C, and the pressure was reduced to atmospheric pressure (about 101. * 71 kilopasp) for a duration of about 1 hour. During this time, approximately 6 grams of water were also collected. The reactor pressure was then reduced from atmospheric pressure to about 6 Torr for a period of 3 hours and where approximately 264.5 grams of glycol was collected.
The polymeric product was then discharged through the lower drain onto a vessel cooled with dry ice to produce 1.03 kilograms of copoly (1, 2-propylene-diethylene co-terephthalate) -copoly (5-sulf or-isof) diethylene 2-propylene-co-5-sulfo-isoplacetalate) -copoly (trimethylolpropane terephthalate) finally blocked with polyethylene derived from Unilin 700. The vitreous transition temperature of the resulting resin product above was measured, It was 58. 7 ° C
(initially) using the Di fi erential 910 Exploration Calorimeter available from E. l. DuPont operating at a heating rate of 10 ° C per minute. The number average molecular weight of the resin of the polyester product was measured to be 3. 300 grams per mole and the weight average molecular weight was measured to be 14,700 grams per mole using tetrahydrofuran as the solvent and obtained with the 700 Satellite WISP gel permeation chromatograph available from the Waters Company equipped with a styrogel column. For the polyester resin of this Example, a softening point of 161 ° C was obtained using the Mettler flow tester. It was found that the acid index 3. & 72'-w * of polyester resin * r? > it was 2.0 milliequivalents per gram of potassium hydroxide.
COMPARATIVE EXAMPLE VII The sodium salt of copoly (1,2-propylene-diethylene) -copoly (1, 2-propylene-diatilen-5-), and without hydrophobic end groups present, was prepared as follows. A two-liter Parr drafter equipped with a lower drain valve, double turbine agitator and distillation receiver with a cold water condenser was charged with 690 grams of dimethyl terephthalate, 8.6 grams of sodium salt of 5-sulfo-isophthalate of dimethyl, 460 grams of 1,2-propandiol, 113 grams of diethylene gricot, and 1.6 grams of butyl tin oxide catalyst obtained as FASCAT 4100MR from Elf Atochem North America, Inc. The editor was then heated to 165 ° C with stirring at 150 revolutions per minute and then heating at 200 ° C for a duration of 6 hours, where methanolic byproduct (228 grams) was collected via the distillation receiver to the vessel, and by-product which was comprised of about 98 volume percent of methanol and 2 volume percent of 1,2-propandiol as measured by the ABBE refractometer available from American Optical Corporation. The mixture was then kept at 200 ° C, and the pressure was reduced from atmospheric
¿? ^^? & ^ íjrr.¿ ^ up to approximately 0.2 Torr for a duration of approximately 3 hours. During this time, 286.5 grams of glycol with approximately 97 volume percent of 1,2-propandiol and 3 volume percent of methanol were also collected as measured by the ABBE refractometer. The reactor was then purged with nitrogen at atmospheric pressure, and the polymer is charged through the lower drainage into a vessel cooled with dry ice to produce 1.13 kilograms of copoly (1,2-propylene terephthalate-diethylene co-terephthalate) -copoly - (diethylene 1,2-propylene-co-5-sulfo-isophthalate 5-sulfoisophthalate) and finally blocked with polyethylene derived from Unilin 700.
The vitreous transition temperature of the product of the previous resulting resin was measured, was 58 ° C
(initially) using the Exploration Calorimeter
Differential 910 available from E.l. Dupont operating at a heating speed of 10 ° C per minute. The number average molecular weight of the resin of the polyester product was measured, was 4,500 grams per mole and the weight average molecular weight was measured, was 10,000 grams per mole using tetrahydrofuran as the solvent and obtained with the permeation chromatograph in gel 700 Satellite WISP available from Waters Company equipped with a styrogel column. For the polyester resin of this example, a softening point of 130 ° C was obtained using the Mettler Flow Tester. It was found that the Acid Index of the polyester resin was 12 milequivalents per gram of potassium hydroxide.
COMPARATIVE EXAMPLE VIII The resin of copoly (1, 2-propylene-terephthalate-diethylene-co-terephthalate 1, 1, 1-trimethylene propane) resin without hydrophilic portions and / or hydrophobic end groups was prepared as follows. A 7.6 liter Parr reactor equipped with a lower drain valve, double turbine agitator and distillation receiver with a cold water condenser was charged with 3,250 grams of dimethyl terephthalate, 2,228.8 grams of 1,2-propandol ( 1 equivalent in excess), 443.1 grams of diethylene glycol, 44.8 grams of trimethylol propane and 4.7 grams of butyl tin catalyst obtained as FASCAT 4100MR from Elf Atochem North America, Inc. The reactor was then heated to 165 ° C with stirring at 150 revolutions per minute and then heated to
200 ° C for 6 hours, where the methanolic byproduct
(809 grams) was collected via the distillation receiver to a container comprised of approximately
98 percent by volume of methanol and 2 percent by volume of 1,2-propandiol as measured by the ABfiB refractometer available from American Optical Corporation. The reactor mixture was maintained at 200 ° C, and the pressure was reduced from atmospheric pressure to approximately 0.2 Torr for a duration of about 3 hours. During this time, approximately 1,240 grams of distillate were further collected in the distillate receiver comprised of approximately 97 volume percent 1,2-propandiol and 3 volume percent methanol as measured by the ABBE refractometer. The pressure was then further maintained at about 0.2 Torr and the temperature of the reaction mixture was increased to 210 ° C for two additional hours, where an additional 30 grams of 1,2-propandiol was collected. The reactor was then tested with nitrogen at atmospheric pressure, and the polymer discharged through bottom drainage over a vessel cooled with dry ice to produce 3.7 kilograms of poly (1, 2-propylene-diethylene terephthalate) resin. -co-terephthalate of 1, 1, 1-trimethylene propane). The glass transition temperature of the resin was measured to be 57.2 ° C (initially) using the Differential Scanning Calorimeter 910 available from E.l. Dupont operating at a heating rate of 10 ° C per minute, the number average molecular weight was measured, was 10,100 grams per mole and the weight average molecular weight was measured was 34,000 grams per mole using g * A; tetrahydrofuran as the solvent and obtained with the 700 WISP gel permeation chromatograph available from Waters Company equipped with a styrogel column. It was found that the melt index of the resin of this example was 17 grams for 10 minutes at 117 ° C with a load of 16.6 kilograms. It was found that the acid number of the polyester resin was 16 milliequivalents per gram of potassium hydroxide.
EXAMPLES IX TO XVI An organic pigment composition comprised of 95 weight percent of the polyester resin of Example I through Example VIII and 5 weight percent of the REGAL 330 pigment was prepared as follows. The polyester resin of Example I to Example
Comparative VIII was crushed to an average volume diameter of approximately 500 microns in a Fitzmill Model J equipped with a 850 micron sieve. After grinding, 950 grams (95 weight percent organic pigment) of the polyester polymer was mixed with 50 grams of black smoke pigment REGAL 330® (5 weight percent organic pigment). The two components were dry mixed first in a paint agitator and then in a roller mill. A given twin screw extruder was used to melt-mix the aforementioned mixture at a barrel temperature effe 14, * 'G, the screw rotational speed of 50 rpm and a feed rate of 20 grams per minute. The extruded strands were broken into coarse particles using a coffee mill available from 5 Black and Decker. An 8-inch Sturtevant micronizer (20.32 centimeters) was used to reduce the particle size even more. After crushing, the organic pigment was measured to see if it had a particle size with an average volume diameter of 9.1 microns with a geometric distribution of 1.43 according to that measured by the Coulter Counter. The resulting organic pigment was then used without further classification. A developer composition was prepared by grinding the prepared organic pigments in a roller mill.
above, 3 parts by weight, with 100 parts by weight of a ferrite-bearing core with a diameter of 90 microns with a coating, 0.55 percent by weight of a polymer of methyl methacrylate (80.4 percent), vinyl triethoxysilane
(5 percent) and styrene (14.1 percent). The data
triboelectrics were obtained using the known Faraday Cage blowing apparatus. The organic pigment / developer was subjected to a humidity of 80 percent in a chamber for 48 hours at 26.66 ° C (80 ° F) to obtain a triboelectric charge of -15.
microcoulombs per gram, and at a humidity level of 20 per
* ^ * '- * cent in a chamber for 48 hours at 15.55 ° C (60 ° F) to obtain a triboelectric charge of -33 microcoulombs per gram. It was measured that the ratio of the triboelectric charge corresponding to a RH of 20 percent to an RH of 80 percent calculated by Equation 1 was 2.2 for a number of organic pigments of the invention. Unmelted copies were then produced using a custom-made imaging apparatus similar to the image forming apparatus 9200 of Xerox Corporation with the fusion system deactivated. The unmelted copies were then melted in the 5090 melter. The triboelectric values, fusion data and other information are listed in Table 1.
TABLE 1
Continuation of TABLE 1
• MFT = Minimum Fixation Temperature • FL Fusion Latitude RH = Relative Humidity Sensitivity The organic pigments of Examples IX to XV were all derived from polyester reams comprised of hydrophilic portions and hydrophobic end groups, and organic pigment which allowed an excellent RH sensitivity such as from about 2.1 to 2.5, excellent mixing, such as less than about 30 seconds, minimum fixing temperature (MFT), low such as from about 135 ° C to about 140 ° C, and latitude of Wide fusion, such as from about 70 to 90 ° C. Comparative Example XV, where the polyester resin was derived from Comparative Example VII which does not contain hydrophobic end groups indicated a higher sensitivity to the RH of 2.8, and slow mixing of more than 60 seconds, and although an MFT of about 140 ° C, the melting latitude was about 55 ° C and narrower than in Examples IX to XIV of the invention of the present invention. Comparative Example XVI, where the polyester resin was derived from Comparative Example VIII which does not contain hydrophilic portions or hydrophobic end groups there was a higher sensitivity of the RH of 4.2, and a slow mixing of more than about 60 seconds. Although a low MFT of about 140 ° C was obtained, the melting latitude was about 50 ° C narrower than in Examples IX to XIV of the invention of the present invention. Other embodiments and modifications of the present invention may occur to those skilled in the art after reviewing the present application and the information presented herein; these modalities and modifications, as well as the equivalents thereof, were also included within the scope of this invention. It is noted that in relation to this date the best method known by the applicant to carry out the aforementioned invention is l > which is clear from the present description of the invention. "AJ _"__.to
Claims (78)
- Having described the invention as above, the content of the following claims is claimed as property. 1. An organic pigment composition, characterized in that it is comprised of a polyester resin with portions, or hydrophilic groups and hydrophobic end groups, colorant, optional wax, optional filler additive and optional surface additives.
- 2. An organic pigment composition, characterized in that it is comprised of a polyester resin containing at least one hydrophilic group, at least one hydrophobic group and dye.
- The organic pigment composition according to claim 2, characterized in that the polyester resin is derived from at least one organic diol monomer, at least one organic diacid or diester monomer, and at least one monofunctional hydrophobic alcohol or monomer of monofunctional acid, at least one alkali metal or alkaline earth metal salt of alkylene sulfonate, a diacid monomer or arylene sulfonate diester.
- 4. The organic pigment composition according to claim 2, characterized in that the polyester resin is of the formulas ? ^! »Jtefi!» ^ *, I,: f? p m where R is a hydrocarbon; X is arylene, an olefinic group or groups, an alkylene; R 'is alkyl or alkylene; and m and n represent the number of random segments; S is a hydrophilic group, Y is equivalent to X or S and at least one hydrophobic final group R 'is two.
- 5. The organic pigment composition according to claim 4, characterized in that R s is an alkylene. -?
- 6. The organic pigment composition according to claim 4, characterized in that R is alkylene with from about 2 to about 20 carbon atoms.
- 7. The organic pigment composition according to claim 4, characterized in that the hydrocarbon has from about 2 to about 22 carbon atoms.
- 8. The organic pigment composition according to claim 4, characterized in that R is cyclohexylene.
- 9. The organic pigment composition according to claim 4, characterized in that R is 1, -dimethylcyclohexylene.
- 10. The organic pigment composition according to claim 4, characterized in that R is ethylene, propylene, butylene or ethylene oxyethylene.
- 11. The organic pigment composition according to claim 4, characterized in that the arylene of X has from about 6 to about 30 carbon atoms.
- 12. The organic pigment composition according to claim 4, characterized in that X s phenylene.
- 13. The organic pigment composition according to claim 4, characterized in that X is phthalene.
- 14. The organic pigment composition according to claim 4, characterized in that X is terephthalene.
- 15. The organic pigment composition according to claim 4, characterized in that X is isophthallene.
- 16. The organic pigment composition according to claim 4, characterized in that the olefinic group X has from about 2 to about 12 carbon atoms.
- 17. The organic pigment composition according to claim 4, characterized in that the olefinic group X is vinylene.
- 18. The organic pigment composition according to claim 4, characterized in that the olefinic group X is methylvinylene.
- 19. The organic pigment composition according to claim 4, characterized in that the alkylene X has from about 2 to about 20 carbon atoms.
- 20. The organic pigment composition according to claim 4, characterized in that the i__t_ 8f alkylene X is ethylene, propylene, butylene, pentylene or hexylene.
- 21. The organic pigment composition according to claim 4, characterized in that the alkyl of R 'contains from 1 to about 120 carbon atoms.
- 22. The organic pigment composition according to claim 4, characterized in that the alkyl of R 'contains from about 5 to about 30 carbon atoms.
- 23. The organic pigment composition according to claim 4, characterized in that the alkyl of R 'is hexyl, heptyl, octyl, lauryl or stearyl.
- 24. The organic pigment composition according to claim 4, characterized in that the alkyl of R 'is polyethylene or polypropylene.
- 25. The organic pigment composition according to claim 4, characterized in that m is a number from about 20 to about 2,000.
- 26. The organic pigment composition according to claim 4, characterized in that m is a number from about 50 to about 125. ____
- 27. The organic pigment composition according to claim 4, characterized in that n is a number from about 1 to about 100.
- 28. The organic pigment composition according to claim 4, characterized in that n is a number from about 50 to about 125.
- 29. The organic pigment composition according to claim 4, characterized in that m is a number from about 100 to about 500, n is a number from about 15 to about 25, and where m is 20 times the value of n. .
- 30. The organic pigment composition according to claim 4, characterized in that S is an alkaline earth metal salt an arylene sulfonate.
- 31. The organic pigment composition according to claim 4, characterized in that S is an alkaline earth metal salt and an alkylene sulfonate.
- 32. The organic pigment composition according to claim 4, characterized in that S is an alkaline earth metal salt an arylene sulfonate and wherein the metal is lithium, sodium, potassium, cesium, beryllium, magnesium, calcium or barium.
- 33. The organic pigment composition according to claim 4, characterized in that X is an alkaline earth metal salt of phenylene sulfonate.
- 34. The organic pigment composition v according to claim 4, characterized in that S is an alkali metal salt of isophthallene 5-sulfonate, terephthalene sulfonate, or alkylene sulfonate.
- 35. The organic pigment composition according to claim 4, characterized in that R 'and X are methylene, propylene, ethylene, butylene, pentylene, hexylene or heptylene.
- 36. The organic pigment composition according to claim 4, characterized in that the polyester resin is also comprised of an additional branching segment, p or q, according to that illustrated in the formulas where R "is a trivalent aromatic or aliphatic radical with about 3 to about 20 carbon atoms, and p and p represent the branching segment and are about 0.1 to about 6 mole percent based on the initial diacid or diester used to prepare the resin, and where the sum of the segments p and q is 100 mol percent of the polyester resin
- 37. The organic pigment composition according to claim 36, characterized in that R "is trivalent derivative of propane, butane, pentane, hexane, cyclohexane, heptane, octane, benzene, naphthalene, or anthracene.
- 38. The organic pigment composition according to claim 36, characterized in that p and q are each from about 0.1 to about 6 mole percent based on the diacid or diester reagent selected for the preparation of the polyester.
- 39. The organic pigment composition according to claim 4, characterized in that the polyester ream is further comprised of an additional branching segment, r or s, according to that illustrated by the formulas •? where R "is a multifunctional radical, and where the sum of the segments rys is 100 mole percent of the polyester resin
- 40. The organic pigment composition according to claim 39, characterized in that R" is an aromatic radical. or polyvalent or tetravalent aliphatic with from about 3 to about 20 carbon atoms of the aliphatic, from about 6 to about 30 of the aromatic; and r and s represent the branching segment and are about 0.1 to about 6 mole percent based on the initial diacid or diester.
- 41. The organic pigment composition according to claim 2, characterized in that The hydrophobic groups are final groups of poly (1, 2-propylene-co-diethylene terephthalate terephthalate) finally blocked with an alkyl group of stearyl or stearate, poly (1, 2-propylene-diethylene terephthalate terephthalate). -co-terephthalate of 1, 1, 1-trimethylene Propane) finally blocked with an alkyl group of stearyl or stearate, poly (1,2-propylene terephthalate) finally blocked with an alkyl group such as stearyl or stearate, poly (1,2-propylene-co-terephthalate), diethylene terephthalate) blocked finally with an alkyl group of lauryl or laurate, & & 9 ~ 1 poly (1, 2-propylene-diethylene terephthalate terephthalate) finally blocked with an alkyl or cetyl or palmitate group, poly (1, 2-propylene-co-diethylene terephthalate terephthalate) finally blocked with octoate , poly (1, 2-propylene-co-diethylene terephthalate terephthalate) finally blocked with an alkyl group of palmitate, stearyl, lauryl, palmitate, stearate or laurate; and mixtures thereof.
- 42. The organic pigment composition according to claim 2, characterized in that S is an ionic salt of a sulphonated dysfunctional monomer where the ion is an alkali metal or alkaline earth metal of lithium, sodium, potassium, cesium, rubidium, magnesium, barium, Calcium or beryllium, and sulfonated or monone dysfunctional function is selected from the group consisting of dimethyl-5-sulfo-isophthalate, dialkyl-5-sulfo-isophthalate-4-sulfo-1, 8-naphthalic anhydride, 4-sulfophthalic acid , 4-sulfophenyl-3,5-dicarboxymethoxybenzene, 6-sulfo-2-naphthyl-3,5-dicarbomethoxybenzene, sulfoterephthalic acid, dimethyl sulfo terephthalate, dialkylsulfo terephthalate, sulfo-ethanediol, 2-sulfo-propanediol, 2-sulfobutanediol, 3-sulfopentanediol, 2-sulfo-hexanediol, 3-sulfo-2-methylpentanediol, sulfonate of N, N-bis (2-hydroxyethyl) -2-aminoethane, 2-sulfo-3-dimethylpentanediol, sulfo-p-hydroxybenzoic acid and mixtures thereof. -! 92
- 43. The organic pigment composition according to claim 2, characterized in that the polyester resin has an average molecular weight of one mole at about 2,000 grams per mole to about 100,000 grams per mole, a weight average molecular weight of about 4,000 grams per mole. mole to about 150,000 grams per mole, and a polydispersity of about 1.8 to about17.
- 44. The organic pigment composition of according to claim 2, characterized in that it has a sensitivity to the relative humidity of the triboelectric charge of about 1.0 to about2. 8.
- 45. The organic pigment composition with a sensitivity to the relative humidity of the triboelectric charge of about 1 to about 2.5.
- 46. The organic pigment composition according to claim 1, characterized in that the additive which increases the filler is additionally included and is present in an amount from about 0.05 to about 5 weight percent, and results in a charged organic pigment. positively or negatively
- 47. The organic pigment composition according to claim 46, characterized in that the additive which increases the charge is incorporated in the organic pigment, or is present on the surface of the organic pigment composition, and results in a pigment. organic charged positively or negatively.
- 48. The organic pigment composition according to claim 2, characterized in that it cons a wax component with a weight average molecular weight of from about 500 to about 20,000.
- 49. The organic pigment composition according to claim 48, characterized in that the wax component is selected from the group consisting of polyethylene and polypropylene.
- 50. The organic pigment composition according to claim 2, characterized in that it also cons as external additives metal salts of a fatty acid, colloidal silicas, metal oxides or mixtures thereof.
- 51. The organic pigment composition according to claim 2, characterized in that the dye is carbon black, cyan, magenta, yellow, red, blue, green, brown or mixtures thereof.
- 52. A developer composition, characterized in that it is comprised of the organic pigment composition according to claim 1 and carrier particles.
- 53. A developer composition, characterized in that it is comprised of the organic pigment composition according to claim 2 and carrier particles. 5
- 54. A method for forming images, characterized in that it comprises formulating a latent electrostatic image on a negatively charged photoreceptor, carrying out the development thereof with the organic pigment composition according to claim 1, and subsequently transferring the developed image to a suitable substrate.
- 55. A process for the preparation of a polyester resin with both at least one hydrophilic portion and at least hydrophobic end groups, characterized in that it comprises the polyesterification of a diester or diacid ^ - ~ 'with a diol or mixture of diols, a polycondensation catalyst, a polyfunctional reagent, and a monofunctional hydrophobic end group monomer.
- 56. The process according to claim 55, characterized in that the diester or diacid is an acid 20 malonic, succinic acid, 2-methylsuccinic acid, 2,3-dimethyl succinic acid, dodecyl succinic acid, glutaric acid, adipic acid, 2-methyl adipic acid, pimelic acid, azelaic acid, sebasic acid, terephthalic acid, isophthalic acid, acid phthalic, 1,2-cyclohexanedioic acid, 1,3-cyclohexanedioic acid, 1-cyclohexanedioic acid, glutaric anhydride, succinic anhydride, dodecyl succinic anhydride, maleic anhydride, fumaric acid, maleic acid, itaconic acid, 2-methylitaconic acid, dialkyl esters, wherein the alkyl comprises from about one carbon atom to about 5 carbon atoms and are diesters of malonic acid, succinic acid, 2-methyl succinic acid, 2,3-dimethylsuccinic acid, dodecyl succinic acid, glutaric acid, acid adipic, 2-methyl adipic acid, pimelic acid, azelaic acid, sebasic acid, terephthalic acid, isophthalic acid, phthalic acid, 1, 2-cyclohexanedioic acid, 1,3-cyclohexanedioic acid, 1,4-cyclohexanedioic acid, mixtures thereof; and diesters, or diacids which are optionally selected in effective amounts of about 45 to about 55 mole percent of the polyester resin; where the diol or glycol is diethylene glycol, ethylene glycol, 1,2-propylene glycol, 1,3-prolylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 1,2 -pentylene glycol, 1,3-pentylene glycol, 1,4-pentylene glycol, 1,5-pentylene glycol, 1,2-hexylene glycol, 1,3-hexylene glycol, 1,4-hexylene glycol, 1,5- hexylene glycol, 1,6-hexylene glycol, heptylene glycols, octylene glycols, decylene glycol, dodecylene glycol, 2,2-dimethyl propanediol, propoxylated bisphenol A, ethoxylated bisphenol A, 1,4-cyclohexanediol, 1,3-cyclohexanediol, , 2-cyclohexanediol, 1,2-cyclohexanedimethanol, or mixtures thereof; and glycols which are optionally selected in effective amounts of about 45 to about 55 mole percent of the polyester resin; where it is selected for the reaction of a catalyst of the polycondensation of tetraalkyl titanates, dialkyl tin oxide, tetraalkyl tin, alkyl tin oxide hydroxide, aluminum alkoxides, alkyl zinc, dialkyl zinc, zinc oxide, stannous oxide, or mixtures thereof, and catalysts which are optionally selected in effective amounts of about 0.01 mole percent to about 5 mole percent based on the initial diacid or diester used to prepare the resin, and where the monomer of the monofunctional hydrophobic end group is hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol and other alcohols derived from about 6 to about 24 carbon atoms, oleyl alcohol, linoleic alcohol, cinnamyl alcohol, substituted alcohols with alkyl such as 2-methylexanol, 2, 3, 3-trimethyl hexanol, 2-me tiloctanol and 3.7-d? methyl-1, 6-octad? en-3-ol, and benzyl alcohol; monofunctional acids such as butyric acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, stearic acid, lauric acid, palmitic acid, oleic acid, linoleic acid, cinnamic acid, higher alkylated acids derived from about 4 to about 24 carbon atoms, benzoic acid, naphthoic acid, or mixtures thereof; and groups which are optionally present in effective amounts of from about 0.1 mole percent to about 4 mole percent based on the initial diacid or diester used to prepare the resin.
- 57. The process according to claim 55, characterized in that the polycondensation is carried out 10 at a temperature of about 165 ° C to about 190 ° C for a duration of about 360 minutes to about 8 hours, followed by an increase in temperature from about 180 ° C to about 220 ° C and reduction of the pressure of the Pressure Atmospheric to about 0.1 millibars to about 100 millibars for a duration of about 60 minutes to about 720 minutes, followed by discharge of the polyester product and cooling to room temperature.
- 58. The organic pigment composition according to claim 2, characterized in that it also contains an additive that increases the charge and a quaternary ammonium compound.
- 59. The organic pigment composition of 25 according to claim 2, characterized in that ^ -s? -? ? it also contains a loading additive of hydroxy bis (3,5-butyl salicylic acid) aluminate, salicylate of 3,5-butyldiaryl, an aluminum compound of a hydroxycarboxylic acid, acetyl pyridinium halide, or distearyl dimethyl ammonium methyl sulfate, wherein the surface additives are comprised of metal salts of a fatty acid, colloidal silicas, metal oxides or mixtures thereof, and wherein each surface additive is present in an amount of about 0.1 to about 5 weight percent.
- 60. The organic pigment according to claim 1, characterized in that the group portion is present on the polymer backbone, or present as a pending group.
- 61. The composition of the organic pigment according to claim 3, characterized in that the polyester is generated from at least one multifunctional branching monomer
- 62. An organic pigment, characterized in that it is comprised of a polyester resin containing at least one segment hydrophilic, hydrophobic segments, and colorant.
- 63. The organic pigment according to claim 62, characterized in that it also contains a wax. A r,,
- 64. The organic pigment according to claim 63, characterized in that the wax is polypropylene, polyethylene, or mixtures thereof.
- 65. The organic pigment according to claim 63, characterized in that it also contains an additive that increases the load.
- 66. The organic pigment according to claim 62, characterized in that it also contains surface additives.
- 67. The organic pigment according to claim 66, characterized in that the surface additives are comprised of silica, metal oxides, metal salts of fatty acids or mixtures thereof.
- 68. An organic pigment according to claim 67, characterized in that each of the additives are present in an amount of about 0.5 to about 3 percent or parts.
- 69. The organic pigment composition according to claim 1, characterized in that it also contains wax, additive that increases the charge and surface additives.
- 70. A developer, characterized in that it is comprised of a carrier and the organic pigment according to claim 27.
- 71. The organic pigment according to claim 4, characterized in that R 'represents the hydrophobic group; and S represents the hydrophilic group.
- 72. The organic pigment according to claim 1, characterized in that at least one is two for the hydrophobic final group.
- 73. The organic pigment according to claim 2, characterized in that at least one is from about 2 to about 10 for the hydrophilic portion.
- 74. The organic pigment according to claim 2, characterized in that at least one for such hydrophobic is two.
- 75. The organic pigment according to claim 1, characterized in that it also contains surface additives.
- 76. The organic pigment according to claim 2, characterized in that it also contains surface additives.
- 77. The organic pigment according to claim 27, characterized in that it also contains wax and an additive that increases the load.
- 78. A polyester of the loi formulas DI characterized in that R is a hydrocarbon; X is arylene, an olefinic group or groups, or an alkylene; R 'is alkyl or alkylene; and m and n represent the number of random segments; S is a hydrophilic group, Y is equal to * X or S, and at least one hydrophobic final group R 'is two.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09317401 | 1999-05-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA00004779A true MXPA00004779A (en) | 2001-11-21 |
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