US5614342A — Methods for preparing cocrystals of titanyl fluor…

Claim 1

Independent Claim 118 words

A method for preparing a cocrystallized titanyl phthalocyanine-titanyl fluorophthalocyanine composition comprising the steps of: admixing crude unsubstituted titanyl phthalocyanine and crude titanyl fluorophthalocyanine to provide a pigment mixture; increasing the amorphousness of said pigment mixture as determined by X-ray crystallography using X-radiation characteristic of Cu Kα at a wavelength of 1.541 Å of the Bragg angle 2θ to provide an amorphous pigment mixture; contacting said amorphous pigment mixture with organic solvent having a gamma c hydrogen bonding parameter of less than 8.0 so as to produce cocrystals of said phthalocyanine and fluorophthalocyanine; and prior to said contacting, substantially excluding said amorphous pigment mixture from contact with organic solvent having a gamma c hydrogen bonding parameter greater than 9.0.

Claim 2

Independent Claim 118 words

A method for preparing a cocrystallized titanyl phthalocyanine-titanyl fluorophthalocyanine composition comprising the steps of: admixing crude unsubstituted titanyl phthalocyanine and crude titanyl fluorophthalocyanine to provide a pigment mixture; increasing the amorphousness of said pigment mixture as determined by X-ray crystallography using X-radiation characteristic of Cu Kα at a wavelength of 1.541 Å of the Bragg angle 2θ to provide an amorphous pigment mixture; contacting said amorphous pigment mixture with organic solvent having a gamma c hydrogen bonding parameter of less than 8.0 so as to produce cocrystals of said phthalocyanine and fluorophthalocyanine; and prior to said contacting, substantially excluding said amorphous pigment mixture from contact with organic solvent having a gamma c hydrogen bonding parameter greater than 9.0.

Claim 3

Dependent Claim 18 words

The method of claim 1 wherein said increasing step further comprises milling said pigment mixture under shear conditions.

Claim 4

Dependent Claim 31 words

The method of claim 1 wherein said increasing step further comprises milling said pigment mixture under shear conditions in the substantial absence of solvent and in the substantial absence of salt.

Claim 5

Dependent Claim 42 words

The method of claim 1 wherein said cocrystallized composition has a first intensity peak at 7.4°±0.2° with respect to X-rays characteristic of Cu Kα at a wavelength of 1.541 Å of the Bragg angle 2θ and a second intensity peak at 28.6°0.2°.

Claim 6

Dependent Claim 44 words

The method of claim 1 wherein said cocrystallized composition exhibits peaks of the Bragg angle 2θ with respect to x-rays of Cu Kα at a wavelength of 1.541 Å at 7.4°, 10.1°, 12.6°, 13.1°, 15.0°, 16.0°, 17.2°, 18.4°, 22.4°, 24.3°, 25.4°, 28.6°, (all ±0.2°).

Claim 7

Independent Claim 220 words

A method for preparing a titanyl phthalocyanine-titanyl fluorophthalocyanine cocrystal comprising the steps of: admixing crude unsubstituted titanyl phthalocyanine and crude titanyl fluoropthalocyanine having the general structure; ##STR3## wherein each of k, l, m, and n is independently an integer from 0 to 4 and at least one of k, l, m, and n is an integer from 1 to 4: to provide a pigment mixture; milling said pigment mixture under shear conditions in the substantial absence of solvent and in the substantial absence of salt to provide a milled mixture; said milling increasing amorphousness of said milled mixture relative to said pigment mixture as determined by X-ray crystallography using X-radiation characteristic of Cu Kα at a wavelength 1.541 Å of the Brag angle 2θ wherein said milled mixture exhibits peaks of the Bragg angle 2θ with respect to x-rays of Cu Kα at a wavelength of 1.541 Å at 7.2°, 15.4°, and 25.5° (all ±0.2°); following said milling, contacting said milled mixture with solvent having a gamma c hydrogen bonding parameter of less than 8.0 so as to produce cocrystals of said phthalocyanine and fluorophthalocyanine; and prior to said contacting step and following said milling step, substantially excluding said pigment mixture and said milled mixture from contact with organic solvent having a gamma c hydrogen bonding parameter greater than 9.0.

Claim 8

Independent Claim 220 words

A method for preparing a titanyl phthalocyanine-titanyl fluorophthalocyanine cocrystal comprising the steps of: admixing crude unsubstituted titanyl phthalocyanine and crude titanyl fluoropthalocyanine having the general structure; ##STR3## wherein each of k, l, m, and n is independently an integer from 0 to 4 and at least one of k, l, m, and n is an integer from 1 to 4: to provide a pigment mixture; milling said pigment mixture under shear conditions in the substantial absence of solvent and in the substantial absence of salt to provide a milled mixture; said milling increasing amorphousness of said milled mixture relative to said pigment mixture as determined by X-ray crystallography using X-radiation characteristic of Cu Kα at a wavelength 1.541 Å of the Brag angle 2θ wherein said milled mixture exhibits peaks of the Bragg angle 2θ with respect to x-rays of Cu Kα at a wavelength of 1.541 Å at 7.2°, 15.4°, and 25.5° (all ±0.2°); following said milling, contacting said milled mixture with solvent having a gamma c hydrogen bonding parameter of less than 8.0 so as to produce cocrystals of said phthalocyanine and fluorophthalocyanine; and prior to said contacting step and following said milling step, substantially excluding said pigment mixture and said milled mixture from contact with organic solvent having a gamma c hydrogen bonding parameter greater than 9.0.

Claim 9

Dependent Claim 64 words

The method of claim 6 wherein said milling steps render said pigment mixture substantially amorphous and said contacting step further comprises converting said amorphous pigment mixture to a cocrystalline material having a first intensity peak at 7.4°±0.2° with respect to X-rays characteristic of Cu Kα at a wavelength of 1.541 Å of the Bragg angle 2θ at and a second intensity peak at 28.6°±0.2°.

Claim 10

Dependent Claim 125 words

A composition of matter comprising cocrystals including unsubstituted titanyl phthalocyanine and titanyl fluorophthalocyanine having the general structure: ##STR4## where each of k, l, m, and n is independently an integer from 0 to 4 and at least one of k, l, m, and n is an integer from 1 to 4; said cocrystals exhibiting an x-ray diffraction spectrum differing tom the x-ray diffraction spectrum of a physical mixture of first crystals consisting essentially of said unsubstituted titanyl phthalocyanine and second crysts consisting essentially of said titanyl fluorophthalocyanine, wherein said cocrystal composition has a first intensity peak at 7.4°±0.2° with respect to X-rays characteristic of Cu Kα at a wavelength of 1.541 Å of the Bragg angle 2θ at and a second intensity peak at 28.6°±0.2°.

Claim 11

Dependent Claim 125 words

A composition of matter comprising cocrystals including unsubstituted titanyl phthalocyanine and titanyl fluorophthalocyanine having the general structure: ##STR4## where each of k, l, m, and n is independently an integer from 0 to 4 and at least one of k, l, m, and n is an integer from 1 to 4; said cocrystals exhibiting an x-ray diffraction spectrum differing tom the x-ray diffraction spectrum of a physical mixture of first crystals consisting essentially of said unsubstituted titanyl phthalocyanine and second crysts consisting essentially of said titanyl fluorophthalocyanine, wherein said cocrystal composition has a first intensity peak at 7.4°±0.2° with respect to X-rays characteristic of Cu Kα at a wavelength of 1.541 Å of the Bragg angle 2θ at and a second intensity peak at 28.6°±0.2°.

Claim 12

Dependent Claim 20 words

The composition of matter of claim 8 wherein said composition of matter is substantially free of salt and of acid.

Claim 13

Dependent Claim 45 words

The composition of matter of claim 8 wherein said composition exhibits peaks of the Bragg angle 2θ with respect to x-rays of Cu Kα at a wavelength of 1.541 Å at 7.4°, 10.1°, 12.6°, 13.1°, 15.0°, 16.0°, 17.2°, 18.4°, 22.4°, 24.3°, 25.4°, 28.6°, (all ±0.2°).

Claim 14

Dependent Claim 33 words

The composition of matter of claim 8 wherein said composition of matter is substantially free of salt or acid and of organic solvent having a gamma c hydrogen bonding parameter greater than 9.0.

Claim 15

Dependent Claim 146 words

An electrophotographic element comprising an electrically conductive layer and a photogenerating layer overlaying said electrically conductive layer, said photogenerating layer including the composition of matter comprising cocrystals including unsubstituted titanyl phthalocyanine and titanyl fluorophthalocyanine having the general structure: ##STR5## where each of k, l, m, and n is independently an integer from 0 to 4 and at least one of k, l, m, and n is an integer from 1 to 4; said cocrystals exhibiting an x-ray diffraction spectrum differing from the x-ray diffraction spectrum of a physical mixture of first crystals consisting essentially of said unsubstituted titanyl phthalocyanine and second crystals consisting essentially of said titanyl fluorophthalocyanine, wherein said cocrystal composition has a first intensity peak at 7.4°±0.2° with respect to X-rays characteristic of Cu Kα at a wavelength of 1.541 Å of the Bragg angle 2θ at and a second intensity peak at 28.6°±0.2°.

Claim 16

Dependent Claim 146 words

An electrophotographic element comprising an electrically conductive layer and a photogenerating layer overlaying said electrically conductive layer, said photogenerating layer including the composition of matter comprising cocrystals including unsubstituted titanyl phthalocyanine and titanyl fluorophthalocyanine having the general structure: ##STR5## where each of k, l, m, and n is independently an integer from 0 to 4 and at least one of k, l, m, and n is an integer from 1 to 4; said cocrystals exhibiting an x-ray diffraction spectrum differing from the x-ray diffraction spectrum of a physical mixture of first crystals consisting essentially of said unsubstituted titanyl phthalocyanine and second crystals consisting essentially of said titanyl fluorophthalocyanine, wherein said cocrystal composition has a first intensity peak at 7.4°±0.2° with respect to X-rays characteristic of Cu Kα at a wavelength of 1.541 Å of the Bragg angle 2θ at and a second intensity peak at 28.6°±0.2°.

Claim 17

Dependent Claim 44 words

The electrophotographic element of claim 12 wherein said composition exhibits peaks of the Bragg angle 2θ with respect to x-rays of Cu Kα at a wavelength of 1.541 Å at 7.4°, 10.1°, 12.6°, 13.1°, 15.0°, 16.0°, 17.2°, 18.4°, 22.4°, 24.3°, 25.4°, 28.6°, (all ±0.2°).

Claim 18

Dependent Claim 32 words

The electrophotographic element of claim 12 wherein said composition of matter is substantially free of salt or acid and of organic solvent having a gamma c hydrogen bonding parameter greater than 9.0.

Claim 19

Dependent Claim 87 words

The electrophotographic element of claim 12 wherein said photogenerating layer has a red and near infrared photosensitivity; determined by electrostatically corona-charging to an initial potential of -700 volts and exposing to monochromatic light at a wavelength of 775 nm, in an amount sufficient to photoconductively discharge the initial potential down to a level of -350 volts; greater than photosensitivity, determined in the same manner, of a photogenerating layer having only unsubstituted titanyl phthalocyanine and of a photogenerating layer having only titanyl fluorophthalocyanine treated in the same manner.

Claim 20

Dependent Claim 77 words

The electrophotographic element of claim 15 wherein said photogenerating layer exhibits a dark decay; determined by electrostatically corona-charging to an initial potential of -700 volts and allowing spontaneous discharge in the dark for seven seconds and dividing the discharge by seven, that is less than the dark decay, determined in the same manner, of a photogenerating layer having a physical mixture of crystals of unsubstituted titanyl phthalocyanine and crystals of titanyl fluorophthalocyanine prepared in the same manner.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	2000-03-24	2000-09-23	2001-03-25	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2004-03-24	2004-09-23	2005-03-25	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2008-03-24	2008-09-23	2009-03-25	$7700.00	Window Closed / Lapsed

Methods for preparing cocrystals of titanyl fluorophthalocyanines and unsubstituted titanyl phthalocyanine, electrophotographic elements, and titanyl phthalocyanine compositions

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