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Water-based pigmented inks

Assignee: 3M Co

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Filing: 1995-11-13

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Granted: 1998-11-24

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Expires: 2015-11-13

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Abstract

Abstract Water-based pigmented inks are disclosed. Such inks are formed from water-based dispersions of pigment particles having novel dispersants therein. The dispersions are formed from the reaction product of an alkenyl azlactone with an N-substituted amino acid compound. Subsequent to the reaction, the reaction product is ring-opened using an amine and, optionally, hydrolyzed. The resulting inks are well-suited for use in ink jet and other printing applications.

Inventors

👤 Larry R. Krepski
👤 Richard J. Kuo
👤 Prabhakara S. Rao
👤 Terrance P. Smith

Bibliographic Details

Application Number —

Jurisdiction US

Data Source google_patents

Last Synchronized 2026-10-26 08:23

CPC Classifications

C; C09; C09D; C09D11/00; C09D11/30; C09D11/38; C09D11/32; C09D11/324; C09D11/326; C09B; C09B67/00; C09B67/0071; C09B67/0084; C09B67/0085; C09K; C09K23/00; C09K23/28; C09K23/42

Claims Analysis

Total Claims: 34

Claim 1

Independent Claim 41 words

A water-based pigmented ink which comprises an suspension of: a) pigment particles, and b) a dispersant which comprises a reaction product of an alkenyl azlactone with an N-substituted amino acid compound which, subsequent to reaction, has been ring-opened using an amine.

Claim 2

Dependent Claim 41 words

Claim 3

Dependent Claim 39 words

A water-based pigmented ink as in claim 1 wherein the azlactone comprises an azlactone selected from the group consisting of 2-ethenyl-1,3-oxazolin-5-one; 2-ethenyl-4-methyl-1,3-oxazolin-5-one; 2-isopropenyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-1,3-oxazolin-5-one; 2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one; 2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one; 2-ethenyl-4-methyl-4-ethyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-4-butyl-1,3-oxazoline-5-one; 2-ethenyl4,4-dibutyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-4-dodecyl-1,3-oxazolin-5-one; 2-isopropenyl-4,4-diphenyl-1,3-oxazolin-5-one; 2-isopropenyl-4,4-pentamethylene-1,3-oxazolin-5-one; 2-isopropenyl-4,4-tetramethylene-1,3-oxazolin-5-one; 2-ethenyl-4,4-diethyl-1,3-oxazolin-5-one; 2-ethenyl-4-methyl-4-nonyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-4-phenyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-4-benzyl-1,3-oxzone-5-one; and 2-ethenyl-4,4-pentamethylene-1,3-oxazolin-5-one.

Claim 4

Dependent Claim 18 words

A water-based pigmented ink as in claim 1 wherein the N-substituted amino acid compound comprises an aspartic ester.

Claim 5

Dependent Claim 19 words

A water-based pigmented ink as in claim 3 wherein the aspartic ester comprises a mono- or bis- aspartic ester.

Claim 6

Dependent Claim 26 words

A water-based pigmented ink as in claim 1 wherein the amine is selected from the group consisting of polyether, butyl, octyl, dodecyl, phenethyl, and octadecyl amines.

Claim 7

Dependent Claim 19 words

A water-based pigmented ink as in claim 1 wherein, subsequent to ring opening, a hydrolysis reaction is carried out.

Claim 8

Dependent Claim 25 words

A water-based pigmented ink as in claim 6 wherein the hydrolysis is carried out using sodium hydroxide, lithium hydroxide, potassium hydroxide, or an ammonium hydroxide.

Claim 9

Dependent Claim 13 words

A water-based pigmented ink as in claim 1 which further comprises a surfactant.

Claim 10

Dependent Claim 14 words

A water-based pigmented ink as in claim 1 which further comprises a alcoholic polyol.

Claim 11

Dependent Claim 16 words

A water-based pigmented ink as in claim 9 wherein the alcoholic polyol comprises an ethylene glycol.

Claim 12

Dependent Claim 24 words

A water-based pigmented ink as in claim 1 wherein the pigment is selected from the group consisting of black, yellow, magenta, and cyan pigments.

Claim 13

Dependent Claim 17 words

A water-based pigmented ink as in claim 11 wherein the black pigment comprises a carbon black pigment.

Claim 14

Dependent Claim 18 words

A water-based pigmented ink as in claim 11 wherein the yellow pigment comprises a nickel azo yellow pigment.

Claim 15

Dependent Claim 17 words

A water-based pigmented ink as in claim 11 wherein the magenta pigment comprises a quinacridone magenta pigment.

Claim 16

Dependent Claim 17 words

A water-based pigmented ink as in claim 11 wherein the cyan pigment comprises a copper phthalocyanine pigment.

Claim 17

Dependent Claim 92 words

A water-based pigmented ink as in claim 1 wherein the dispersant comprises: ##STR6## wherein R is an alkyl, aryl, or aralkyl group; R 3 and R 4 are hydrogen or lower alkyl; R 5 is hydrogen or methyl; R 6 and R 7 are independently hydrogen, alkyl, or aryl; R 8 is an alkyl group, aryl group, oligomeric or fluorinated alkyl; R 9 and R 10 are independently alkyl, aryl, or aralkyl, respectively, or a cation; R 11 is H or R 8 m is 1-6; and n is 0 or 1.

Claim 18

Dependent Claim 56 words

A water-based pigmented ink which comprises, a suspension of: a) pigment particles, and b) a dispersant made by a process which comprises i) reacting an alkenyl azlactone with an N-substituted amino acid compound to form a first reaction product, and ii) ring-opening the first reaction product using an amine, to thereby form a second reaction product.

Claim 19

Dependent Claim 56 words

Claim 20

Dependent Claim 39 words

A water-based pigmented ink as in claim 17 wherein the azlactone comprises an azlactone selected form the group consisting of 2-ethenyl-1,3-oxazolin-5-one; 2-ethenyl-4-methyl-1,3-oxazolin-5-one; 2-isopropenyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-1,3-oxazolin-5-one; 2-ethenyl-4,4-dimethyl-1,3-oxazolin-5-one; 2-isopropenyl-4,4-dimethyl-1,3-oxazolin-5-one; 2-ethenyl-4-methyl-4-ethyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-4-butyl-1,3-oxazoline-5-one; 2-ethenyl-4,4-dibutyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-4-dodecyl-1,3-oxazolin-5-one; 2-isopropenyl-4,4-diphenyl-1,3-oxazolin-5-one; 2-isopropenyl-4,4-pentamethylene-1,3-oxazolin-5-one; 2-isopropenyl-4,4-tetramethylene-1,3-oxazolin-5-one; 2-ethenyl-4,4-diethyl-1,3-oxazolin-5-one; 2-ethenyl-4-methyl-4-nonyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-4-phenyl-1,3-oxazolin-5-one; 2-isopropenyl-4-methyl-4-benzyl-1,3-oxzone-5-one; and 2-ethenyl-4,4-pentamenthylene-1,3-oxazolin-5-one.

Claim 21

Dependent Claim 18 words

A water-based pigmented ink as in claim 17 wherein the N-substituted amino acid compound comprises an aspartic ester.

Claim 22

Dependent Claim 19 words

A water-based pigmented ink as in claim 19 wherein the aspartic ester comprises a mono- or bis- aspartic ester.

Claim 23

Dependent Claim 26 words

A water-based pigmented ink as in claim 17 wherein the amine is selected from the group consisting of polyether, butyl, octyl, dodecyl, phenethyl, and octadecyl amines.

Claim 24

Dependent Claim 19 words

A water-based pigmented ink as in claim 17 wherein, subsequent to ring opening, a hydrolysis reaction is carried out.

Claim 25

Dependent Claim 25 words

A water-based pigmented ink as in claim 22 wherein the hydrolysis is carried out using sodium hydroxide, lithium hydroxide, potassium hydroxide, or an ammonium hydroxide.

Claim 26

Dependent Claim 13 words

A water-based pigmented ink as in claim 17 which further comprises a surfactant.

Claim 27

Dependent Claim 14 words

A water-based pigmented ink as in claim 17 which further comprises a alcoholic polyol.

Claim 28

Dependent Claim 16 words

A water-based pigmented ink as in claim 25 wherein the alcoholic polyol comprises an ethylene glycol.

Claim 29

Dependent Claim 24 words

A water-based pigmented ink as in claim 17 wherein the pigment is selected from the group consisting of black, yellow, magenta, and cyan pigments.

Claim 30

Dependent Claim 17 words

A water-based pigmented ink as in claim 27 wherein the black pigment comprises a carbon black pigment.

Claim 31

Dependent Claim 18 words

A water-based pigmented ink as in claim 27 wherein the yellow pigment comprises a nickel azo yellow pigment.

Claim 32

Dependent Claim 17 words

A water-based pigmented ink as in claim 27 wherein the magenta pigment comprises a quinacridone magenta pigment.

Claim 33

Dependent Claim 17 words

A water-based pigmented ink as in claim 27 wherein the cyan pigment comprises a copper phthalocyanine pigment.

Claim 34

Dependent Claim 92 words

A water-based pigmented ink as in claim 17 wherein the dispersant comprises: ##STR7## wherein R is an alkyl, aryl, or aralkyl group; R 3 and R 4 are hydrogen or lower alkyl; R 5 is hydrogen or methyl; R 6 and R 7 are independently hydrogen, alkyl, or aryl; R 8 is an alkyl group, aryl group, oligomeric or fluorinated alkyl; R 9 and R 10 are independently alkyl, aryl, or aralkyl, respectively, or a cation; R 11 is H or R 8 m is 1-6; and n is 0 or 1.

References Cited (Backward Citations)

US4304705A Cited

US4597794A Cited

US4485236A Cited

US4451619A Cited

US4699843A Cited

US5336742A Cited

US4931582A Cited

US5216084A Cited

US5236741A Cited

US5149806A Cited

US5268473A Cited

US5085698A Cited

US4988602A Cited

US5194623A Cited

US5091489A Cited

US5081197A Cited

US5284512A Cited

US5519085A Cited

US5243012A Cited

US5292514A Cited

US5424445A Cited

US5310778A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	2001-11-23	2002-05-25	2002-11-24	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2005-11-23	2006-05-25	2006-11-24	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2009-11-23	2010-05-25	2010-11-24	$7700.00	Window Closed / Lapsed

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