US3619239A - Pressure sensitive copying paper - Google Patents

Pressure sensitive copying paper Download PDF

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Publication number
US3619239A
US3619239A US3619239DA US3619239A US 3619239 A US3619239 A US 3619239A US 3619239D A US3619239D A US 3619239DA US 3619239 A US3619239 A US 3619239A
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United States
Prior art keywords
pressure sensitive
alkyl group
sensitive copying
beta
copying paper
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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Inventor
Chiaki Osada
Hisatake Ono
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Fujifilm Corp
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Fujifilm Corp
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Priority to JP9035168 priority Critical
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Publication of US3619239A publication Critical patent/US3619239A/en
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Application status is Expired - Lifetime legal-status Critical

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Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41MPRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00Duplicating or marking methods; Sheet materials for use therein
    • B41M5/124Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
    • B41M5/132Chemical colour-forming components; Additives or binders therefor
    • B41M5/136Organic colour formers, e.g. leuco dyes
    • B41M5/15Spiro-pyrans
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02Making microcapsules or microballoons
    • B01J13/025Applications of microcapsules not provided for in other subclasses
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00Stock material or miscellaneous articles
    • Y10S428/914Transfer or decalcomania
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31844Of natural gum, rosin, natural oil or lac
    • Y10T428/31848Next to cellulosic

Abstract

WHEREIN N IS AN INTEGER OF 1 TO 4; R1 and R2 represent an alkyl group having 1 to 4 carbon atoms or a phenyl group; R3 represents a hydrogen atom, an alkoxyl group wherein the alkyl group is an alkyl group having 1 to 4 carbon atoms, an alkoxycarbonyl group wherein the alkyl group is an alkyl group having 1 to 4 carbon atoms or a halogen atom.
A novel color forming material used in a pressure sensitive copying paper comprises

Description

United States Patent [72] Inventors Chlaki Osada:

Hisatake Ono. both of Asaka-shi, Japan [21] Appl. No 884,006

[22] Filed Dec. 10. I969 [45] Patented Nov. 9, I971 [73 Assignee Fuji Photo Film Co.. Ltd.

Kanagawa, Japan [32] Priority Dec. 10. 1968 [33] Japan [54] PRESSURE SENSITIVE COPYING PAPER 4 Claims, No Drawings [52] U.S. Cl .4 1l7/36.2, ll7/36.8. 260/326 [Sl] lnt.Cl 841m 5/22 [50] Field of Search 1 17/362. 36.8, 36.9; Zoo/326.11

[56] References Cited UNITED STATES PATENTS 3,231,584 1/1966 Berman et al ll7/36.8 3,239 366 3/1966 Miller etal. 117/362 $293,060 l2/l966 Harbort.... ll7/36.2 3,445,261 5/l969 Talvalkar 1 17/369 3.451338 6/l969 Baum ll7/36.8

Primary Examiner-Murray Katz A!r0rne \'-Sughrue. Rothwell, Mion Zinn & Macpeak ABSTRACT: A novel color forming material used in a pressure sensitive copying paper comprises wherein n is an integer of l to 4; R and R represent an alkyl group having 1 to 4 carbon atoms or a phenyl group; R represents a hydrogen atom, an 'alkoxyl group wherein the alkyl group is an alkyl group having I to 4 carbon atoms. an alkoxycarbonyl group wherein the alkyl group is an alkyl group having l to 4 carbon atoms or a halogen atom.

PRESSURE SENSITIVE COPYING PAPER BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a pressure sensitive copying paper.

2. Description of the Prior Art A pressure sensitive copying paper, as herein defined, is one wherein an electron donative, color reactive colorless organic substance (hereinafter referred to as a color former) reacts (usually) with an electron accepting substance in a nonpolar oily solvent medium to thereby assume a color.

As a color former, there are leuco methylene blue, crystal violet lactone, Rhodamine B lactam, acid Rhodamine B sultone, etc., as an electron accepting substance there are acid clay, active earth, attapulgite, aluminum sulfate, natural zeolite, kaolin, bentonite, silica gel, feldspar, pyrophylite, halloysite, magnesium trisilicate, zinc sulfate, zinc sulfide calcium fluoride, and organic acids and salts thereof such as calcium citrate, tannic acid, benzoic acid, etc.

In general, a pressure sensitive copying paper comprises a combination of a sheet of paper the surface of which is coated with the above color former which is dissolved in a nonpolar solvent such as benzene, toluene, trichlorodiphenyl, etc. and then microencapsulated; and a sheet of paper the surface of which is coated with the electron acceptive substance together with a binder. In certain cases, a further sheet, one side of which is coated with the microcapsule and other side of which is coated with the electron accepting substance, may be used between the above two sheets. Also, a sheet coated with the microcapsules and the electron accepting substance on the same surface can occasionally be employed. ln either case, the microcapsules are ruptured by writing or printing pressure and the color former solution contained therein is contacted with an electron accepting substance to give a colored copying image. The principles and preparation processes described above are well known. (Refer to the specifications of U.S. Pat. Nos. 2,548,366; 2,711,375; 2,730,256; 2,812,507; 2,800,457 and 2,800,458).

However, the above pressure sensitive copying papers must be preserved for long periods of time in some uses, and conventional color formers have not sufficiently satisfied the necessary requirements because the color formers have been poor in their weather-proofing qualities and limited in their color shade.

SUMMARY OF THE lNVENTlON The present invention provides an improved pressure sensitive copying paper using a novel color'forming compound represented by the formula:

wherein n is an integer of 1 to 4; R and R represent an alkyl group having one to four carbon atoms or a phenyl group; R represents a hydrogen atom, an alkoxyl group wherein the alkyl group is an alkyl group having one to four carbon atoms an alkoxycarbonyl group wherein the alkyl group is an alkyl group having one to four carbon atoms or a halogen atom.

Typically used in combination with an electron acceptive material, the above color-forming compound yields a lasting color.

lt is thus one object of this invention to provide an improved pressure sensitive copying paper.

It is a further object of the invention to provide an improved color-forming compound.

These and other objects will become clear upon a reading of the following material.

DETAILED oEsgntP oN or THE PREFERRED EM D NTS The 5, of the present invention is to provide a pressure sensitive copying paper using a compound represented by the for- (CHZMCOOH mula:

wherein n is an integer of l to 4, each of hand R is analltyl group having one toffour carbon atoms ora phenyl group, and R3 is a ydr e a n a y ha in il is bu carb n atoms, an alltoitylgroup, an alltoxycarbonyl group wherein. the

alkyl groupis an alll yl group having one tofour carbon atoms, I

or a halogen atom, as a color former.

ltis sufficient if the abovecompounds are dissolvedinasolvent such as benzene, toluene, diotylphthialate, chlorinated of the above compound andthe electron acceptive substance,

maybe simultaneously coated on the surface of the same sheet ofpaper.

Microcapsules of a color former solution can be prepared according to the specifications of U.S. Pat. No. 2,800,457, or British Pat. Nos. 1,091,076; l,09l,077;or 1,091,078.

Compounds represented by the above formula can, in general, be synthesized by the following process: R ,C,,H, NH-NH and R R CHCOCH are reacted .inthe absenceof a solvent to synthesize a phenyl hydrazone derivative Next. the above phenyl-hydrazone derivative is refluxed in the presence of ZnCl, in ethyl alcohol to synthesizethecorresponding indolenine derivative. The indolenine derivative and BR(CH ),.CO0H are then reacted either in the absence of solvent or using an appropriate solvent at to C. to thereby quatenarize The quatenary salt thus obtained and aformyl-B-naphthol can be refluxed together with triethylamine added in a calculated amount in absolute ethanolto obtain a compound represented by the above formula. These reactions are as shown in the following equations:

R. R CHO OH R: Ca3+ i l (COmCoOH i i :O- r

COOH

The pressure sensitive copying paper of the present invention is excellent in its preservability before and after use because the compound represented by the above formula has excellent solubility and stability, and. therefore. it is better in its weather-proofing qualities in comparison with conventional pressure sensitive copying papers. Further, the above compound yields an excellent color shade.

EXAMPLE 1 In 50 ml. of ethanol, 6.2 g. of l-fi-carboxyethyl-2.3.3- trimethyl-indolenium bromide and 3.4 g. of a-formyl-B- naphthol were dissolved and. after adding 2 g. of triethylamine. refluxed at 78 C. for 2 hours. After reaction. the ethanol was distilled out to obtain a white crystal which was then recrystallized from ethanol to obtain 3.6 g. of the white crystals of l-[3-carboxyethyl-3.3-dimethyl spiro-(indoline-2,2-2'H-fl-naphthopyrane). The melting point of this compound was 203 to 208 C. A piece of paper. the surface of which was coated with a solution of the present compound in ethanol and which was combined with a paper coated with acid clay and a binder was typed with a typewriter. whereby the place where pressure was applied immediately colored red. Encapsulation was by the procedure of US. Pat. No. 2,800,457.

EXAMPLE 2 To 100 g. ofa l percent aqueous solution of methyl cellulose, l0 g. of a solution of 1 percent of compound obtained in example 1 in chlorinated diphenyl was added and vigorously stirred to form an emulsion. Next, the emulsion was coated on a paper surface and dried. The thickness of the coated layer was about 100 t. When this color-forming paper was superposed on a clay-coated paper as in example 1 and subjected to local pressure. the area wherein pressure was applied immediately colored to red.

EXAMPLE 3 In the same manner as example 1, 3.3 g. of l-B-carboxyethyl-2,3.3,S-tetramethylindolenium bromide and 1.7 g. of aformyl-B-carboxethyl-3,3,S-tetramethylindoenium bromide and 1.7 g. of a-formyl-fl-naphol were reacted to obtain 2.0 g. of the white crystals of l-B-carboxyethyl-3,3,5-trimet.hyl spiro(indoline-2,2'-2'H-fl-naphthopyrane). The melting point of this compound was 196 to 197 C. When pressure was cally applied, as by writing in example 2, the areas where pressure was applied colored red.

EXAMPLE 4 By the same procedure, as in example I, 3.5 g. of l-B-carboxyethyl-2,3,3-trimethyl5-chloroindolenium bromide and 1.7 g. of a-formyl-B-naphtol were reacted to obtain L?! g. of

the white crystals of l-B-carboxyethyl-3.3-dimethyl-5-chloro spiro (indoline-2.2'-2'H-B-naphthopyrane). The melting point of this compound was 206 to 208 C. A solution of this compound in chlorinated diphenyl was coated on a paper surface which was then superposed on the surface of clay-coated paper and subjected to the pressure. The area where pressure was applied immediately colored red.

EXAMPLE 5 The compound obtained in example 4 was microencapsulated according to the process described in the specification of Japanese Pat. No. 493,064. The microcapsules were coated on a paper and dried. The color-forming paper obtained was superposed on a clay-coated paper and subjected to local pressure, whereupon it immediately colored red.

What is claimed is:

l. A pressure sensitive copying paper having a coating layer of microcapsules containing a compound capable of causing a color-forming reaction with an electron acceptive material. said compound being represented by the general formula wherein n is an integer of l to 4; R and R represent an alkyl group having one to four carbon atoms or a phenyl group; R represents a hydrogen atom, an alkoxyl group wherein the alkyl group is an alkyl group having one to four carbon atoms. an alkoxycarbonyl group wherein the alkyl group is an alkyl group having one to four carbon atoms or a halogen atom.

2. The pressure sensitive copying paper as claimed in claim 1 wherein said compound is from the group consisting of I43- carboxyethyl-3 .3-dimethyl-spiro(lndollne-Z ,2 '-2 'H-B- naphthopyrane). l-B-carboxyethyl3.3.5-trimethylspiro(indoline-2.2'-2'H-B-naphthopyrane) or l-B-carboxyethyl-B,3- dimethyl-5-chlorospiro(indoline-Z.2'-2'H-B-naphthopyrane).

3. The pressure sensitive copying paper as claimed in claim 1 wherein said electron acceptive material is from the group consisting of acid clay. active clay, attapulgite. zeolite. Roline, bentonite, silica gel. aluminum sulfate. feldspar, pyrophyllite. halloysite, magnesium trisilicate. zinc sulfate. zinc sulfide, calcium fluoride. calcium citrate. tannic acid or benzoic acid.

4. A coloring-forming compound represented by the formu-

Claims (2)

  1. 2. The pressure sensitive copying paper as claimed in claim 1 wherein said compound is from the group consisting of 1- Beta -carboxythyl-3,3-dimethyl-spiro(indoline-2,2''-2''H- Beta -naphthopyrane), 1- Beta -carboxyethyl3,3,5-trimethylspiro(indoline-2,2''-2''H- Beta -naphthopyrane) or 1- Beta -carboxyethyl-3,3-dimethyl-5-chlorospiro(indoline-2,2''-2''H- Beta -naphthopyrane). 3. The pressure sensitive copying paper as claimed in claim 1 wherein said electron acceptive material is from the group consisting of acid clay, active clay, attapulgite, zeolite, Roline, bentonite, silica gel, aluminum sulfate, feldspar, pyrophyllite, halloysite, magnesium trisilicate, zinc sulfate, zinc sulfide, calcium fluoride, calcium citrate, tannic acid or benzoic acid.
  2. 4. A coloring-forming compound represented by the formula:
US3619239D 1968-12-10 1969-12-10 Pressure sensitive copying paper Expired - Lifetime US3619239A (en)

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DE (1) DE1961921B2 (en)
FR (1) FR2025804A1 (en)
GB (1) GB1245079A (en)
IE (1) IE33875B1 (en)

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4220356A (en) * 1976-08-24 1980-09-02 Fuji Photo Film Co., Ltd. Recording materials containing chromenoindoles
US4223060A (en) * 1976-01-19 1980-09-16 Wiggins Teape Limited Pressure-sensitive copying paper
US5488114A (en) * 1992-08-20 1996-01-30 Matsushita Electric Industrial Co., Ltd. Labelling color, method of preparing the same and method for detecting methamphetamine with the color
US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
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
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
US5837429A (en) 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5858586A (en) 1993-08-05 1999-01-12 Kimberly-Clark Corporation Digital information recording media and method of using same
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
US6017661A (en) 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
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
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same
US6368396B1 (en) 1999-01-19 2002-04-09 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
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same

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US3231584A (en) * 1959-07-16 1966-01-25 Ncr Co 1-phenyl-3, 3-dimethylspiro[(2'h-1'-benzopyran)-2', 2'-indoline] compound
US3239366A (en) * 1961-11-21 1966-03-08 Ncr Co Thermotransfer sheet material and copying systems utilizing same
US3293060A (en) * 1956-02-06 1966-12-20 Wagner Guenter Writing and manifolding material
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US3293060A (en) * 1956-02-06 1966-12-20 Wagner Guenter Writing and manifolding material
US3231584A (en) * 1959-07-16 1966-01-25 Ncr Co 1-phenyl-3, 3-dimethylspiro[(2'h-1'-benzopyran)-2', 2'-indoline] compound
US3239366A (en) * 1961-11-21 1966-03-08 Ncr Co Thermotransfer sheet material and copying systems utilizing same
US3451338A (en) * 1964-05-11 1969-06-24 Ncr Co Thermographic recording system
US3445261A (en) * 1965-10-23 1969-05-20 Ncr Co Heat-sensitive record material

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4223060A (en) * 1976-01-19 1980-09-16 Wiggins Teape Limited Pressure-sensitive copying paper
US4220356A (en) * 1976-08-24 1980-09-02 Fuji Photo Film Co., Ltd. Recording materials containing chromenoindoles
US5488114A (en) * 1992-08-20 1996-01-30 Matsushita Electric Industrial Co., Ltd. Labelling color, method of preparing the same and method for detecting methamphetamine with the color
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
US6054256A (en) 1993-08-05 2000-04-25 Kimberly-Clark Worldwide, Inc. Method and apparatus for indicating ultraviolet light exposure
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US6127073A (en) 1993-08-05 2000-10-03 Kimberly-Clark Worldwide, Inc. Method for concealing information and document for securely communicating concealed information
US6120949A (en) 1993-08-05 2000-09-19 Kimberly-Clark Worldwide, Inc. Photoerasable paint and method for using photoerasable paint
US5858586A (en) 1993-08-05 1999-01-12 Kimberly-Clark Corporation Digital information recording media and method of using same
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US6060200A (en) 1993-08-05 2000-05-09 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms and methods
US5721287A (en) 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
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
US6342305B1 (en) 1993-09-10 2002-01-29 Kimberly-Clark Corporation Colorants and colorant modifiers
US6090236A (en) 1994-06-30 2000-07-18 Kimberly-Clark Worldwide, Inc. Photocuring, articles made by photocuring, and compositions for use in photocuring
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
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
US6063551A (en) 1995-06-05 2000-05-16 Kimberly-Clark Worldwide, Inc. Mutable dye composition and method of developing a color
US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US5837429A (en) 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US6033465A (en) 1995-06-28 2000-03-07 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6168655B1 (en) 1995-11-28 2001-01-02 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5885337A (en) 1995-11-28 1999-03-23 Nohr; Ronald Sinclair Colorant stabilizers
US6099628A (en) 1996-03-29 2000-08-08 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
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5782963A (en) 1996-03-29 1998-07-21 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
US6277897B1 (en) 1998-06-03 2001-08-21 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6503559B1 (en) 1998-06-03 2003-01-07 Kimberly-Clark Worldwide, Inc. Neonanoplasts and microemulsion technology for inks and ink jet printing
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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DE1961921B2 (en) 1971-12-23
IE33875B1 (en) 1974-11-27
IE33875L (en) 1970-06-10
DE1961921A1 (en) 1970-08-27
BE742809A (en) 1970-05-14
FR2025804A1 (en) 1970-09-11
GB1245079A (en) 1971-09-02

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