US5521271A — Liquid toners with hydrocarbon solvents

Claim 1

Independent Claim 36 words

A polymeric dye comprising a polymeric moiety, a chromophore moiety, a surface release-promoting moiety, and an optional charge-directing chelating moiety, said polymeric moiety comprising macromeric segment(s) that render said polymeric dye dispersible in a hydrocarbon solvent.

Claim 2

Dependent Claim 36 words

A polymeric dye comprising a polymeric moiety, a chromophore moiety, a surface release-promoting moiety, and an optional charge-directing chelating moiety, said polymeric moiety comprising macromeric segment(s) that render said polymeric dye dispersible in a hydrocarbon solvent.

Claim 3

Dependent Claim 63 words

The polymeric dye of claim 1, wherein said dye is represented by the formula {MAC} x {CCS} 1-x , wherein MAC represents macromeric segment(s) that render said polymeric dye dispersible in a hydrocarbon solvent, CCS represents chromophore-containing segment(s), x represents the weight fraction of said macromeric segment(s) in said polymeric dye, the value of x being greater than zero and less than one.

Claim 4

Dependent Claim 18 words

The polymeric dye of claim 2, wherein the value of x ranges from about 0.1 to about 0.9.

Claim 5

Dependent Claim 18 words

The polymeric dye of claim 2, wherein the value of x ranges from about 0.15 to about 0.3.

Claim 6

Dependent Claim 42 words

The polymeric dye of claim 2, wherein CCS comprises moieties derived from (a) at least one free radically polymerizable monomer containing a chromophore that is covalently linked to said monomer and (b) optionally, at least one essentially colorless free radically polymerizable monomer.

Claim 7

Dependent Claim 77 words

The polymeric dye of claim 5, wherein said monomer (a) is represented by the formula CHROMO--X.sub.1 --CO--CR═CH.sub.2 wherein CHROMO represents a dye moiety derived from a dye selected from the group consisting of hydrazone, anthraquinone, azo, metal-azo, azomethine, metalazomethine, aminostyryl, phthalocyanine, and indoaniline dyes; R represents hydrogen, alkyl group having from 1 to 18 carbon atoms, or aryl group having from 6 to 18 carbon atoms in the ring portion thereof; X 1 represents NH or O.

Claim 8

Dependent Claim 122 words

A polymeric dye comprising a polymeric moiety having macromeric segment(s), and a chromophore moiety, said polymeric dye is represented by the formula: {MAC}.sub.x {CCS}.sub.1-x wherein; MAC represents macromeric segment(s) that render said polymeric dye dispersible in a hydrocarbon solvent and is derived from the reaction of a free radically polymerizable monomer, a chain transfer agent, a free radical generating initiator, and a coupling agent; CCS represents chromophore-containing segment(s); and x represents the weight fraction of said macromeric segment(s) with respect to MAC and CCS portion of said polymeric dye, the value of x being greater than zero and less than one; said polymeric dye having attached thereto at least one of (a) a charge-directing chelating moiety or (b) a surface release-promoting moiety.

Claim 9

Dependent Claim 122 words

A polymeric dye comprising a polymeric moiety having macromeric segment(s), and a chromophore moiety, said polymeric dye is represented by the formula: {MAC}.sub.x {CCS}.sub.1-x wherein; MAC represents macromeric segment(s) that render said polymeric dye dispersible in a hydrocarbon solvent and is derived from the reaction of a free radically polymerizable monomer, a chain transfer agent, a free radical generating initiator, and a coupling agent; CCS represents chromophore-containing segment(s); and x represents the weight fraction of said macromeric segment(s) with respect to MAC and CCS portion of said polymeric dye, the value of x being greater than zero and less than one; said polymeric dye having attached thereto at least one of (a) a charge-directing chelating moiety or (b) a surface release-promoting moiety.

Claim 10

Dependent Claim 44 words

The polymeric dye of claim 7, wherein said free radically polymerizable monomer is selected from the group consisting of lauryl methacrylate, lauryl acrylate, iso-bornyl methacrylate, iso-bornyl acrylate, iso-octyl methacrylate, iso-octyl acrylate, iso-decyl acrylate, iso-decyl methacrylate, n-decyl acrylate, n-decyl methacrylate, n-octodecyl acrylate, and n-octodecyl methacrylate.

Claim 11

Dependent Claim 30 words

The polymeric dye of claim 7, wherein said free radically polymerizable monomer is selected from the group consisting of lauryl methacrylate, lauryl acrylate, iso-bornyl methacrylate, iso-bornyl acrylate and iso-octyl acrylate.

Claim 12

Dependent Claim 27 words

The polymeric dye of claim 7, wherein said chain transfer agent is selected from the group consisting of mercaptoalcohols, bromoalcohols, mercaptocarboxylic acids, and halogenated aliphatic carboxylic acids.

Claim 13

Dependent Claim 28 words

The polymeric dye of claim 10, wherein said chain transfer agent is selected from the group consisting of 3-mercapto-l,2-propanediol, 2-mercaptoethanol, 3-mercapto-2-butanol, 1-mercapto-2-propanol, 2-mercapto-3-pyridinol, mercaptophenol, bromethanol, and mercaptoacetic acid.

Claim 14

Dependent Claim 26 words

The polymeric dye of claim 7, wherein said coupling agent is selected from the group consisting of acryloyl halides, methacryloyl halides, isocyanatoalkyl methacrylates, and glycidyl methacrylates.

Claim 15

Dependent Claim 24 words

The polymeric dye of claim 12, wherein said coupling agent is selected from the group consisting of acyloyl chloride, methacryloyl chloride, and isocyanatoethyl methacrylate.

Claim 16

Dependent Claim 26 words

The polymeric dye of claim 7, wherein said free radical generating initiator is selected from the group consisting of 2,2'-azobis(2-methylpropionitrile), 4,4'-azobis(4-cyanopentoic) acid, 2,2'-azobis{2-methyl-N-[1,1-bis(hydroxyethyl)propionamide}, 2,2'-azobis{2-methyl-N-[1,1-bis(hydroxymethylethyl)propionamide}, and 2,2'-azobis{2-methyl-N-(2-hydroxyethyl)propionamide}.

Claim 17

Dependent Claim 14 words

The polymeric dye of claim 1, said dye including a charge directing chelating moiety.

Claim 18

Dependent Claim 29 words

The polymeric dye of claim 15, wherein said charge-directing chelating moiety is a bidentate chelating moiety capable of forming a 5- or 6-membered ring around a coordinated metal center.

Claim 19

Dependent Claim 37 words

The polymeric dye of claim 16 wherein said bidentate chelating moiety is derived from a member selected from the group consisting of 4-vinyl bipyridine, 4-vinyl-4'-methyl bipyridine, 3-vinylbenzylacetylacetone, 3-allylacetylacetone, acetoacetoxyethyl acrylate, acetoacetoxyethyl methacrylate, 5-methacryloxymethyl-8-hydroxyquinoline, N-vinylbenzyliminodiacetic acid, and 18-vinyl-5,6-benzo-4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexa-cos-2-ene.

Claim 20

Dependent Claim 17 words

The polymeric dye of claim 1, wherein said surface release-promoting moiety comprises at least two silicon atoms.

Claim 21

Dependent Claim 26 words

The polymeric dye of claim 18, wherein said surface release-promoting moiety is derived from a monomer selected from the group consisting of 3-methacryloxypropyltris(trimethylsiloxy)silane, 3-acryloxypropyltris(trimethylsiloxy)silane, vinyltris(trimethylsiloxy)silane, tris[tris(trimethylsiloxy)siloxylvinylsilane.

Claim 22

Dependent Claim 17 words

The polyrneric dye of claim 1, wherein said surface release-promoting moiety comprises at least two fluorine atoms.

Claim 23

Dependent Claim 30 words

The polymeric dye of claim 20, wherein said surface release-promoting moiety is derived from a monomer selected from the group consisting of perfluorooctyl acrylate, perfluorooctyl methacrylate, and perfluorooctyl ether acrylate.

Claim 24

Dependent Claim 49 words

A composition comprising a hydrocarbon solvent and a polymeric dye comprising a polymeric moiety, a chromophore moiety, and at least one of (a) a charge-directing chelating moiety or (b) a surface release-promoting moiety, said polymeric moiety comprising macromeric segment(s) that render said polymeric dye dispersible in a hydrocarbon solvent.

Claim 25

Dependent Claim 49 words

A composition comprising a hydrocarbon solvent and a polymeric dye comprising a polymeric moiety, a chromophore moiety, and at least one of (a) a charge-directing chelating moiety or (b) a surface release-promoting moiety, said polymeric moiety comprising macromeric segment(s) that render said polymeric dye dispersible in a hydrocarbon solvent.

Claim 26

Dependent Claim 11 words

The composition of claim 22, wherein said composition is a latex.

Claim 27

Dependent Claim 13 words

The composition of claim 22, wherein said polymeric dye bears an electrostatic charge.

Claim 28

Dependent Claim 17 words

The composition of claim 22, wherein said electrostatic charge is effected by complexation with a multivalent ion.

Claim 29

Dependent Claim 13 words

The composition of claim 25, wherein said multivalent ion is Zr 4+ .

Claim 30

Dependent Claim 11 words

The composition of claim 22, wherein said composition is a toner.

Claim 31

Dependent Claim 26 words

A polymeric dye comprising a polymeric moiety, a chromophore moiety, and at least one of (a) a charge-directing chelating moiety or (b) a surface release-promoting moiety.

Claim 32

Dependent Claim 26 words

A polymeric dye comprising a polymeric moiety, a chromophore moiety, and at least one of (a) a charge-directing chelating moiety or (b) a surface release-promoting moiety.

Claim 33

Dependent Claim 13 words

The polymeric dye of claim 28, said dye including a charge-directing chelating moiety.

Claim 34

Dependent Claim 29 words

The polymeric dye of claim 28, wherein said charge-directing chelating moiety is a bidentate chelating moiety capable of forming a 5- or 6-membered ring around a coordinated metal center.

Claim 35

Dependent Claim 37 words

The polymeric dye of claim 30, wherein said bidentate chelating moiety is derived from a monomer selected from the group consisting of 4-vinyl bipyridine, 4-vinyl-4'-methyl bipyridine, 3-vinylbenzylacetylacetone, 3-allylacetylacetone, acetoacetoxyethyl acrylate, acetoacetoxyethyl methacrylate, 5-methacryloxymethyl-8-hydroxyquinoline, N-vinylbenzyliminodiacetic acid, and 18-vinyl-5,6-benzo-4,7,13,16,21,24-hexaoxa-1,10diazabicyclo[8.8.8]hexa-cos-2-ene.

Claim 36

Dependent Claim 13 words

The polymeric dye of claim 28, said dye including a surface release-promoting moiety.

Claim 37

Dependent Claim 17 words

The polymeric dye of claim 32, wherein said surface release-promoting moiety comprises at least two silicon atoms.

Claim 38

Dependent Claim 26 words

The polymeric dye of claim 33, wherein said surface relese-promoting moiety is derived from a monomer selected from the group consisting of 3-methacryloxypropyltris(trimethylsiloxy)silane, 3-acryloxypropyltris(trimethylsiloxy)silane, vinyltris(trimethylsiloxy)silane, tris[tris(trimethylsiloxy)siloxylvinylsilane.

Claim 39

Dependent Claim 17 words

The polymeric dye of claim 32, wherein said surface release-promoting moiety comprises at least two fluorine atoms.

Claim 40

Dependent Claim 30 words

The polymeric dye of claim 35, wherein said surface release-promoting moiety is derived from a monomer selected from the group consisting of perfluorooctyl acrylate, perfluorooctyl methacrylate, and perfluorooctyl ether acrylate.

Claim 41

Dependent Claim 43 words

A composition comprising a hydrocarbon solvent and a polymeric dye comprising a polymeric moiety, a chromophore moiety, a surface release-promoting moiety, and an optional charge-directing chelating moiety, said polymeric moiety comprising macromeric segment(s) that render said polymeric dye dispersible in a hydrocarbon solvent.

Claim 42

Dependent Claim 43 words

A composition comprising a hydrocarbon solvent and a polymeric dye comprising a polymeric moiety, a chromophore moiety, a surface release-promoting moiety, and an optional charge-directing chelating moiety, said polymeric moiety comprising macromeric segment(s) that render said polymeric dye dispersible in a hydrocarbon solvent.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1999-05-28	1999-11-27	2000-05-28	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2003-05-28	2003-11-27	2004-05-28	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2007-05-28	2007-11-27	2008-05-28	$7700.00	Window Closed / Lapsed

Liquid toners with hydrocarbon solvents

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