US2477165A - Nondusting compositions containing stabilized diazo compounds - Google Patents

Nondusting compositions containing stabilized diazo compounds Download PDF

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US2477165A
US2477165A US71890646A US2477165A US 2477165 A US2477165 A US 2477165A US 71890646 A US71890646 A US 71890646A US 2477165 A US2477165 A US 2477165A
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carbonate
compounds
powder
stabilized
diazo
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Herman A Bergstrom
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GAF Chemicals Corp
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GAF Chemicals Corp
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033Blends of pigments; Mixtured crystals; Solid solutions
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0092Dyes in solid form
    • C09B67/0094Treatment of powders, e.g. antidusting

Description

Patented July 26, 1949 NONDUSTI NG COMPOSITIONS CONTAINING STABILIZED DIAZO COWOUNDS Herman A. Bergstrom, Albany, N. Y., assignor to General Aniline & Film Corporation, New York, N. Y., a. corporation of Delaware No Drawing. Application December 27, 1946,

Serial No. 718,906

7 Claims. (Cl. 260-1d1) This invention relates to a process for reducing dusting in powders, more particularly in powders of organic color compounds, chromogens and auxochromic compounds and to dustless compositions of the same.

It is customary in the manufacture oforganic color compounds, i. e., dyestuffs and or anic pigments, and of 'chromogens and auxochromic compounds to prepare these materials in powder form asin this way economy and convenience in shipping and handing of the products is to be obtained. These advantages in the powder form of the products are offset to some extent by the tendency of the products to become objectionably dusty in handling, a condition brought about by air-lifting of very fine product particles which are always present in the powders. The degree of the dusting will vary depending on the concentration of very fine particles in the powders and on the conditions surrounding the handling of the powders, such as the presence and magand measuring are difficult while in extreme cases accurate measurement is sometimes a practical impossibility due to loss of material.

I have now found that dustiness in pulverulent organic color compounds, chromogens' and auxichromic compounds may be overcome in an advantageous manner by incorporating therewith a minor proportion of a liquid dialkyl carbonate having at least 5 carbon atoms.

These dialkyl carbonates contain an aggregate of at least 4 carbon atoms in the alkyl groups and under normal pressure boil at a. temperature above 125 C. 'They exhibit toward the oragnic color compounds, chromogens and auxochromic compounds, non-reactivity, but a slight solvent action, non-interference with their use in the role of colorant, chromogen or auxochromic compound as the case may be, and a high degree of permanency in respect to the dust-binding effect. Among dialkyl carbonates which may be employed as dust-binding agents in the process of the invention may be mentioned, for example,

diethyl carbonate, methylpropyl carbonate, ethylpropyl carbonate, dipropyl carbonate, ethylisopropyl carbonate, dibutyl carbonate, ethyl-secbutyl carbonate, di-sec-butyl carbonate, di-isobutyl carbonate, methylisobutyl carbonate, ethylisobutyl carbonate, methyl-sec-n-amyl carbonate, si-lsoamyl carbonate, etc. a

The amount of the liquid dialkyl carbonates used in treating the powders in accordance with the invention may. b varied. Positive results in dust reduction may be obtained with as little as 0.5% of one of the dialkyl carbonates on the weight of the powder.- Optimum amounts range from about 1 to 3% by weight. although in some instances for best results up to about 5% by weight may be required. Where economically feasible. still larger amounts may be used with excellent results, for example between about 5 and 10% by weight. Amounts should not be employed, however, as would set up a continuous liquid phase in the powder bringing about separation of the dialkyl carbonate therefrom :by drainage. The incorporation of theliquid dialkyl carbonates with the powders may be accomplished in any suitable and convenient way,

for example, by the use of powder-blending ma chines having provision for spraying or otherwise distributing. the liquid uniformly; over the mass of the powder so as to avoid formation of pastes in the mass. For best results, a thorough mixing of the powder and liquid should be obtained.

The term chromogen is used herein in the customar sense of the term to mean those organic compounds which, in themselves not dyestufis, are capable of being converted to dyestuffs by anagency such as oxidation or by coupling with a compound containing one or more auxochrome Under the groups, i. e., auxochromic compounds. term chromogen as definedherein are included leuco vat dyestuffs and their derivatives such as the leuco sulfuric acid esters, which compounds on oxidation are converted to the vat dyestuffs, and the water-soluble stabilized diazo compounds which in aqueous medium, acid, neutral of alkaline as the case may be, couple with auxochromic compounds.

The term auxochromic compound is used herein in the customary sense of the term to mean those organic compoundswhich contain one or more auxochromes which principally are hydroxy, amino and substituted amino groups. Compounds of this kind are for example, resorcinol,

The water-soluble stabilized diazo compounds may be prepared by reacting the diazonium salt in aqueous solution with metal salts such as zinc chloride, cadmium chloride and 'tin chloride or with compounds such as the alkali metal fluoroborates, alkyl or aryl sulfonic acids, e. g., naphthalene-1,5-disulfonic acid, and acid sulfates. These stabilized diazo. compounds exhibit the properties of true salts in that they ionize immediately in neutral or acid solution and show the reaction of diazo ions. Amines which carry one or more water-solubilizing groups such as the sulfonic or carboxylic acid groups to render the stabilized compound'soluble in water may also be used for the preparation of stabilized diazo compounds. Amines of this character are, for example, sarcosine, methyl taurine, N-ethyl or N- methyl-5-suifo-'anthranilic acid, proline and N- methyl glucamine. Depending on whether the amine employed is primary or secondary, the resulting stabilized compound'is' a diazo-amino or a diazo-imino compound. In the art and herein also, these stabilized diazo-amino and diazoimino compounds are contained under the generic or collective term, water-soluble stabilized diazoamino compounds.

The invention and the application of the process thereof to the preparation of dustless powders of organic color compounds, chromogens and auxochromic compounds is illustrated in more detail in the following examples, to which, however, it is not intended that the invention be limited. Parts are by weight.

Example 1 50 parts of a powder of a stabilized diazo compound constituted by the zinc chloride double salt of diazotised 5-nitro-o-anisidine and 1 part of diethyl carbonate are thoroughly mixed by milling together in a small mixing device. The treated powder is non-dusting and has excellent storage stability. 1

Example 2 50 parts of a powder of the azo dye prepared by coupling diazotised p-nitroaniline with dihydroxyethyl-m-toluidine is mixed as in Example 1 with 1 part of diethyl carbonate. The composition is a non-dusting powder.

Example 3 50 parts of a powder of dimethoxy dibenzanthrone is mixed in the manner of the preceding examples with 1 part of diethyl carbonate. The product is outstanding in non-dusting character.

Example 4 50 parts of a powder of diazotised 5-nitro-oanisidine which is stabilized with N-ethyl-5-sulfoanthranilic acid is mixed as before with 1 part of diethyl carbonate. The product is characterized by oustanding non-dusting character.

Example 5 50 parts of a powder of a stabilized diazo compound which is the zinc chloride double salt of diazotised i-chloro-o-nitroanillne is milled in a small mixing device with 2.5 parts of dlethyl carbonate. The product is'of excellent non-dusting character.

Example 6 50 parts of a powder of an azoic dye mixture comprising Naphthol AS--G (bisacetoacet-otoluidide) and diazotised 5-chioro-o-anisidine stabilized with sarcosine is well mixed with 2.5 parts of di-isopropyl carbonate. The composition is a non-dusting powder.

In like manner, the process may be applied for the reduction of dusting in powders of chromogens,-auxochromic compounds and dyestuffs generally, and for the preparation of non-dusting powders of organic pigments, such as azo pigments per se, metal complexes of azo dyestuffs such as the copper or cobalt complexes of the azo dyestuffs obtained by coupling tetrazotised dianisidine or tetrazotised benzidine with 2-naphthol-G-sulfonic acid (Schaefiers salt), phthalocyanine pigments, and color lakes such as those prepared by the deposition on water-insoluble substratum such as barium sulfate of azo dyestuffs, for example, the yellow pigment from the coupling of diazotised o-nitro-p-chloro-aniline with acetoacet-o-chloroanilide. Non-dusting powders of dyestuffs such as methyl violet, crystal violet and the rhodamines, acridine dyestuffs and vat dyestuffs, for example indanthrories, pyranthrones, flavanthrones, dibenzanthrones, anthranthrones, dibenzpyrenequinones, anthrimidecarbazoles, naphthacridones, indigo, thioindigo, indirubin, etc., and their leuco and leuco ester derivaties.

The invention is applicable to the preparation of dustless powder compositions which contain a water-soluble stabilized diazo compound in admixture with a Naphthol-AS type coupler. In its broader aspect the process may be applied in many instances to the binding of dust in powder mixtures of organic color compounds, chromogens or auxochromic compounds which contain other powdered materials useful in the coloring art, such' as dyeing or printing assistants, for example, surface-active agents, e. g., aliphatic acid condensation products of taurine. The same relative proportions of the liquid dialkyl carbonates are applicable in such cases, the total quantity thereof being taken on the weight of the powder mixture.

I claim:

1. A composition of matter comprising a pulw verulent water-soluble stabilized diazo compound which is a salt admixed with an amount of an at least 5 carbon atom liquid dialkyl carbonate, which is not below about 0.5% by weight but is less than would result in liquid separation by drainage.

2. A composition of matter comprising a powder of a water-soluble stabilized diazo compound which is a salt admixed with from about 1 to 5% by weight of an at least 5 carbon atom liquid dialkyl carbonate.

3. A composition of matter comprising a powder of a water-soluble stabilized diazo compound which is a salt admixed with from about 1 to 5% by weight of diethyl carbonate.

4. A composition of matter comprising a powder of a water-soluble double salt of a metal salt and a diazo compound admixed with from about 1 to 5% by weight of an at least 5 carbon atom liquid dialkyl carbonate.

5% by weight of an at least 5 carbon atom liquid dialkyl carbonate.

6. A composition of matter comprising a, pulverulent water-soluble stabilized diazo compound which is a salt of an aryl sulfonic acid admixed with from about 1 to 5 per cent by weight of an at least 5 carbon atom liquid dialkyl carbonate. 7. A composition of matter as defined in claim 6, wherein the liquid dialkyl carbonate is diethyl carbonate.

HERMAN A. BERGSTROM.

REFERENCES CITED The following referenlces are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 1,572,715 Gunther Feb. 9, 1926 2,090,511 Crossley Aug. 17, 1937 10 2,138,572 Etzelmiller Nov. 29, 1938 FOREIGN PATENTS Number Country Date 274,642 Germany May 22, 1914

US2477165A 1946-12-27 1946-12-27 Nondusting compositions containing stabilized diazo compounds Expired - Lifetime US2477165A (en)

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Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2628959A (en) * 1953-02-17 Process for making stabilized
FR2388027A1 (en) * 1977-04-18 1978-11-17 Ciba Geigy Ag Process for the preparation of granules of dyes or optical brighteners without dust
US5616443A (en) * 1993-08-05 1997-04-01 Kimberly-Clark Corporation Substrate having a mutable colored composition thereon
US5643356A (en) * 1993-08-05 1997-07-01 Kimberly-Clark Corporation Ink for ink jet printers
US5645964A (en) * 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US5681380A (en) * 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5700850A (en) * 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US5709955A (en) * 1994-06-30 1998-01-20 Kimberly-Clark Corporation Adhesive composition curable upon exposure to radiation and applications therefor
US5721287A (en) * 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5733693A (en) * 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US5739175A (en) * 1995-06-05 1998-04-14 Kimberly-Clark Worldwide, Inc. Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer
US5747550A (en) * 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5773182A (en) * 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US5782963A (en) * 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5786132A (en) * 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US5798015A (en) * 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
US5811199A (en) * 1995-06-05 1998-09-22 Kimberly-Clark Worldwide, Inc. Adhesive compositions containing a photoreactor composition
US5837429A (en) * 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US5849411A (en) * 1995-06-05 1998-12-15 Kimberly-Clark Worldwide, Inc. Polymer film, nonwoven web and fibers containing a photoreactor composition
US5855655A (en) * 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5865471A (en) * 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5885337A (en) * 1995-11-28 1999-03-23 Nohr; Ronald Sinclair Colorant stabilizers
US5891229A (en) * 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6008268A (en) * 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US6017471A (en) * 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6017661A (en) * 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6033465A (en) * 1995-06-28 2000-03-07 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6071979A (en) * 1994-06-30 2000-06-06 Kimberly-Clark Worldwide, Inc. Photoreactor composition method of generating a reactive species and applications therefor
US6099628A (en) * 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US6228157B1 (en) 1998-07-20 2001-05-08 Ronald S. Nohr Ink jet ink compositions
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
US6265458B1 (en) 1998-09-28 2001-07-24 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6277897B1 (en) 1998-06-03 2001-08-21 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6294698B1 (en) 1999-04-16 2001-09-25 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
US6368396B1 (en) 1999-01-19 2002-04-09 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same
US6503559B1 (en) 1998-06-03 2003-01-07 Kimberly-Clark Worldwide, Inc. Neonanoplasts and microemulsion technology for inks and ink jet printing
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE274642C (en) *
US1572715A (en) * 1926-02-09 Rhine
US2090511A (en) * 1935-04-18 1937-08-17 Calco Chemical Co Inc Colloidized vat dye
US2138572A (en) * 1936-08-06 1938-11-29 Du Pont Dyeing and printing compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE274642C (en) *
US1572715A (en) * 1926-02-09 Rhine
US2090511A (en) * 1935-04-18 1937-08-17 Calco Chemical Co Inc Colloidized vat dye
US2138572A (en) * 1936-08-06 1938-11-29 Du Pont Dyeing and printing compositions

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Publication number Priority date Publication date Assignee Title
US2628959A (en) * 1953-02-17 Process for making stabilized
FR2388027A1 (en) * 1977-04-18 1978-11-17 Ciba Geigy Ag Process for the preparation of granules of dyes or optical brighteners without dust
US4227880A (en) * 1977-04-18 1980-10-14 Ciba-Geigy Corporation Process for the production of dustfree granules of dyes and optical brighteners
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US5643356A (en) * 1993-08-05 1997-07-01 Kimberly-Clark Corporation Ink for ink jet printers
US5643701A (en) * 1993-08-05 1997-07-01 Kimberly-Clark Corporation Electrophotgraphic process utilizing mutable colored composition
US5645964A (en) * 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US5616443A (en) * 1993-08-05 1997-04-01 Kimberly-Clark Corporation Substrate having a mutable colored composition thereon
US5683843A (en) * 1993-08-05 1997-11-04 Kimberly-Clark Corporation Solid colored composition mutable by ultraviolet radiation
US5700850A (en) * 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US6017471A (en) * 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US5721287A (en) * 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5733693A (en) * 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US5908495A (en) * 1993-08-05 1999-06-01 Nohr; Ronald Sinclair Ink for ink jet printers
US6066439A (en) * 1993-08-05 2000-05-23 Kimberly-Clark Worldwide, Inc. Instrument for photoerasable marking
US5773182A (en) * 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US5865471A (en) * 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US6060223A (en) * 1993-08-05 2000-05-09 Kimberly-Clark Worldwide, Inc. Plastic article for colored printing and method for printing on a colored plastic article
US6060200A (en) * 1993-08-05 2000-05-09 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms and methods
US6120949A (en) * 1993-08-05 2000-09-19 Kimberly-Clark Worldwide, Inc. Photoerasable paint and method for using photoerasable paint
US6054256A (en) * 1993-08-05 2000-04-25 Kimberly-Clark Worldwide, Inc. Method and apparatus for indicating ultraviolet light exposure
US6127073A (en) * 1993-08-05 2000-10-03 Kimberly-Clark Worldwide, Inc. Method for concealing information and document for securely communicating concealed information
US5858586A (en) * 1993-08-05 1999-01-12 Kimberly-Clark Corporation Digital information recording media and method of using same
US6342305B1 (en) 1993-09-10 2002-01-29 Kimberly-Clark Corporation Colorants and colorant modifiers
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
US5709955A (en) * 1994-06-30 1998-01-20 Kimberly-Clark Corporation Adhesive composition curable upon exposure to radiation and applications therefor
US6071979A (en) * 1994-06-30 2000-06-06 Kimberly-Clark Worldwide, Inc. Photoreactor composition method of generating a reactive species and applications therefor
US6090236A (en) * 1994-06-30 2000-07-18 Kimberly-Clark Worldwide, Inc. Photocuring, articles made by photocuring, and compositions for use in photocuring
US6008268A (en) * 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US6017661A (en) * 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6235095B1 (en) 1994-12-20 2001-05-22 Ronald Sinclair Nohr Ink for inkjet printers
US5849411A (en) * 1995-06-05 1998-12-15 Kimberly-Clark Worldwide, Inc. Polymer film, nonwoven web and fibers containing a photoreactor composition
US5837429A (en) * 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US5798015A (en) * 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
US5786132A (en) * 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US6063551A (en) * 1995-06-05 2000-05-16 Kimberly-Clark Worldwide, Inc. Mutable dye composition and method of developing a color
US5747550A (en) * 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5739175A (en) * 1995-06-05 1998-04-14 Kimberly-Clark Worldwide, Inc. Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer
US5811199A (en) * 1995-06-05 1998-09-22 Kimberly-Clark Worldwide, Inc. Adhesive compositions containing a photoreactor composition
US5681380A (en) * 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US6033465A (en) * 1995-06-28 2000-03-07 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US5885337A (en) * 1995-11-28 1999-03-23 Nohr; Ronald Sinclair Colorant stabilizers
US6168655B1 (en) 1995-11-28 2001-01-02 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5782963A (en) * 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6168654B1 (en) 1996-03-29 2001-01-02 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5891229A (en) * 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6099628A (en) * 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5855655A (en) * 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6503559B1 (en) 1998-06-03 2003-01-07 Kimberly-Clark Worldwide, Inc. Neonanoplasts and microemulsion technology for inks and ink jet printing
US6277897B1 (en) 1998-06-03 2001-08-21 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6228157B1 (en) 1998-07-20 2001-05-08 Ronald S. Nohr Ink jet ink compositions
US6265458B1 (en) 1998-09-28 2001-07-24 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6368396B1 (en) 1999-01-19 2002-04-09 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
US6294698B1 (en) 1999-04-16 2001-09-25 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same

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