New! View global litigation for patent families

US3502476A - Light-sensitive photographic materials - Google Patents

Light-sensitive photographic materials Download PDF

Info

Publication number
US3502476A
US3502476A US3502476DA US3502476A US 3502476 A US3502476 A US 3502476A US 3502476D A US3502476D A US 3502476DA US 3502476 A US3502476 A US 3502476A
Authority
US
Grant status
Grant
Patent type
Prior art keywords
photographic
light
material
sensitive
sulfone
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
Application number
Inventor
Kohei Itano
Masashi Nakano
Shoichiro Hoshino
Akira Kato
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Konica Corp
Original Assignee
Konica Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Grant date

Links

Images

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/675Compositions containing polyhalogenated compounds as photosensitive substances

Description

United States Patent 01 lice 3,502,476 Patented Mar. 24, 1970 US. C]. 9690 7 Claims ABSTRACT OF THE DISCLOSURE A composition contains a compound capable of producing .free radicals upon exposure to light and an organic compound which reacts with the said free radicals to produce a color change. The free radicals progenitors are halogenated organic sulfoxides or sulfone compounds.

This invention relates to light-sensitive, photographic materials including both the printing-out and bleachingout types. More particularly, this invention relates to a light-sensitive, photographic material comprising a photoactivator capable of generating a free radical by the action of light and a color modifier capable of showing a visible color change by the action of said free radical, said photo-activator being a halogenated organic sulfoxide or sulfone compound of the below-mentioned general formula. It is a principal object of the invention to provide a light-sensitive, photographic material having good stability, non-toxic processibility, excellent sensitiveness and good tone quality.

In the known light-sensitive, photographic material of the above-indicated type, halogenated hydrocarbons are commonly used as photo-activators, among which carbon tetrabromide and aroyl trihalogenated hydrocarbons are particularly preferred. The photographic material made of carbon tetrabromide, however, suifers from a serious disadvantage, that is, very poor stability because of the dissipation of the carbon tetrabromide from the material due to its high volatility. For example, such photographic material as made of carbon tetrabromide is so unstable that it may become useless within several days after its preparation. Furthermore, carbon tetrabromide vapor is very toxic and so that environment for workers should be kept below 1 ppm. of the carbon tetrabromide (cf. F.M. Turner, Atomic Energy Res. Estab. Great Brit. MED/M-Zl, 1958). Accordingly, it is necessary to take a special care for avoiding respiration of the toxic vapor during handling of the material. Aroyl halogenated hydrocarbons are less volatile than carbon tetrabromide. However, they have severe lachrymatorines and so it is necessary to take a care in order to avoid inhalation of the resulting vapor during thermal fixing.

In accordance with the present invention, a halogenated organic sulfoxide or sulfone compound of the general formula (wherein X is hydrogen, chlorine or bromine; Y is hydrogen, chlorine or bormine; Z is chlorine or bromine; and

R is non-substituted or substituted aryl group, heterocyclic group or a group in which R R and R individually are hydrogen, chlorine or bromine) is employed as a photo-activator thereby overcoming all the disadvantages encountered in the prior art.

All the compounds represented by the above-indicated general formula are crystalline and do not show such volatility as carbori tetrabromide has. Therefore, a light-sensitive photographic material of the present invention which contains the above-specified compound is very stable because of its being free from dissipation of the photoactivator. Further, this material is entirely non-toxic and does not raise any lachrymatory vapor, and so it can be handled without any special care. The light-sensitive photographic material advantageously has high sensitiveness and good tone quality in comparison with those of any known photographic material. For instance, the photographic material of the present invention can give more sharp color tone even when the same color modifier as in the known photographic material is used.

Typical compounds useful as photo-activators in the present invention will be listed below. It is, however, to be noted that they are merely illustrative and do not limit the scope of the invention.

( 1) Hexabromodimethyl-sulfoxide M.P. C:

M.P. 117 C.

1'8 (4) Trichloromethyl-phenyl-sulfone (5) Tribr0momethyl-phenyl-sulfone (6) Trichloromethyl-p-chlorophenyl-sulfone (7) Tribrmomethyl-p-nitrophenyl-sulfone Tetrabromodimethyl-sulfone O CHBrz (decomp) (1 l) 2,4-dichlorophenyl-trichloromethyl-sulfone 12) 2-methyl-4-chlorophenyl-trichloromethyl-sulfone Cl CH M.P.100 o.

( l3) 2,S-dimethyl-4-chlorophenyl-trichloromethylulfone S-COl; I g M.P. 150C. 01

(14) 2,4-dichlorophenyl-tribromomethyl-sulfone M.P. 132C.

( 15) Bromomethyl-dibromomethyl-sulfone O OHzBr s M.P. 67C. 0 CHBrz These compounds can be obtained with ease by bringng the corresponding thioglycolic acid derivative into 'eaction with an aqueous sodium hypochlorite or hypo- )romite solution at a temperature of to 40 C. The :tarting material to be used is rather cheap and the abovenentioned procedures for preparation are simple. The :ompounds thus prepared can generate an active halogen free radical which will cause a visible color change in *espect to a color modifier, when these compounds are exaosed to light, particularly ultraviolet ray. Those which :ontain a nitrophenyl or chlorophenyl group in their tructure are particularly advantageous, because they are :ensitive over the broad range of spectrum covering light )f a long wave length.

M.P. 201 C.

M.P. 142 C.

M.P. 150 C.

M. P. 160-162 C.

M.P. 98 C.

Color modifiers, which can provide a visible color change by the action of a free radical resulting from a photo-activator, can be classified in two types. Those of the first type are such inherently colorless materials which can be converted to the colored state by the action of a free radical. Those of the second type are such inherently colored materials whose color can be changed to another color or can be decolorized by the action of a free radical. A light-sensitive photographic material using a color modifier of the former type can be employed in so-called nega-posi system since said material which is originally colorless develops color on the action of light. On the other hand, a light-sensitive photographic material using a color modifier of the latter type is using in so-called posi-posi system. Typical color modifiers of the first type include aryl amines. In addition to simple aryl amines, socalled Leuco dyes which are aminoor substituted aminobearing dyes in reduced form can be used. Typically are included the following: Diphenyl amine, dibenzyl amine, triphenyl amine, N,N-diethyl aniline, N,N-dimethyl aniline, N-hydroxy-N-ethyl aniline, dibenzyl aniline, oaminodiphenyl amine, p hydroxydiphenyl amine, N- vinyl carbazole, 2-phenyl indolidine, N,N-dihydroxyethyl aniline, N,N-diphenyl-p-phenylene diamine, N,N-dihydroXyethyl-m-toluidine, oz-naPhthYl amine, p-dimethylamino-benzaldehyde, 3-aminoquinoline, indole, salicylidene-p-toluidine, salicylidene-p-chloroaniline, cyanomethylene 4 quinolyl-Z-naphthalene, 3-phenyl-indole, a-diethylamino-pyridine, p,p-methylene bis-aniline, p,p'- methylene bis (N,N-dimethylaniline), p,p'-benxylidine bis-(N,N-dimethylaniline), p,p',p-methylidine tris-(N, N diethylaniline), p,p hydroxymethylene bis(N,N-dimethylaniline), p,p' (dimethylamino) diphenyl amine, p,p-aminomethylene-bis (N,N-dimethylaniline p,p- (0"- chlorobenzylidene) bis(N,N-dimethylaniline), p,p'-(p"- aminobenzylidene) bis aniline, p,p' (p" amino-m"- methylbenzylidene) bis (N-phenylaniline) 1,1-bis(p-dimethylaminophenol)-p-dimethylaminophthalein, 3,6-bis (diethylamino) spiro(phthalein-1,9-Xanthene) 3,6-bis diethylamino) 9 (p dimethylaminophenol)Xanthene, 1,1 bis(p dimethylaminophenol) p dimethylaminophthalane, 1,1 bis(p aminophenol) p aminophenolphthalane, 10 benzoyl 3,7-di(p-dimethylamino) -phenothiazine, 10 cinnamoyl-3,7-di(p-dimethylamino)-phenothiazine, 3-diethylamino-7-aminophenoxazine, etc. Other color modifiers effective for use in the nega-poSi system are the quarternary salts and N-oxides of nitrogen-containing heterocyclic compounds. Typical examples include the quarternary salts of Z-methylbenzthiazole methyl iodide, 2-methylbenzthiazole ethyl bromide, quinardine methyl iodide, 2,S-dimethyl-benzthiazole methyl-p-tolnenesulfonate and 2,5,6-trimethylbenzthiazole butyl iodide, as well as 4-methylquinoline N-oxide, 2,2-dipyridine N- oxide disulfide and quinoline N-oxide. Sometimes these N-oxide compounds are preferable used because they can show some sensitizing efi'ect.

Color modifiers which can be effectively used in the posi-posi system include a variety of dyes, e.g. diphenyl methane dyes, triphenyl methane dyes, thiazine dyes, oxazine dyes, Xanthene dyes, anthraquinone dyes, iminonaphthoquinone dyes, azomethine dyes, etc. Typical examples are Orlamin (Cl. 41000), Victoria Blue (Cl. 44045), Victoria Blue R (Cl. 44040), Brilliant Lowdurine Blue (CI. 42565), Benzoyl Methylene Blue, Cinnamoyl Methylene Blue, p-Anisoyl Methylene Blue, New Methylene Blue (C.I. 51195), Nile Blue A (CI. 51180), Ephitenew Blue (CI. 51185), Rhodamine B (C.I. 45170), Rhodamine 3B (-C.I. 45175), Rhodamine 12 GM (CI. 45310), Sudan Brau G (CI. 61525), Sudan Blue GN (C.I. 61520), Celliton Blue (CI. 64500), 4-p-diethylaminophenylimino naphthoquinone, 2 carboxyanilino 4 pdiethylaminophenylimino-naphthoquinone, Z-carbostearylamino 4 p dihydroxyethylaminophenylimino naphmethylphenylimino acetanilide, cyano p diethylaminothoquinone, p methoxybenzoyl p diethylamino ophenylimino acetanilide, 1 phenyl 3 methyl 4 pdiethylaminophenylimino 5 pyrazolone, 1 8 naphthyl 3 methyl 4 p diethylaminophenylimino 5- pyrazolone, etc.

A light-sensitive, photographic material of the present invention can be prepared by coating a solvent solution comprising the above-mentioned photo-activator and color modifier together with an appropriate film-forming polymeric binder on a support (e.g. paper, film base, etc.) and then drying. Suitable binders include cellulose derivatives, e.g. acetyl cellulose, acetyl butyryl cellulose, ethyl cellulose, etc.; vinyl polymers or copolymers, e.g. polyvinyl chloride, polyvinylidene chloride, polyvinyl acetate, polyacrylic esters, polystyrenes, styrene-maleic anhydride copolymer, etc.; and synthetic rubbers, e.g. cyclized rubber, acryl rubber, butadiene copolymers, etc.

A light-sensitive photographic material of the invention can produce an image on its light-sensitive side through a visible color change caused by the action of a free radical resulting from the photo-activator when the said photographic material is subjected to imagewise exposure to light. Light sensitiveness of such photographic material can be increased by addition of a sensitizer. Suitable sensitizers can be classified into two groups, one of which belongs to so-called optical sensitizers capable of broadening the sensible wave length region of the light-sensitive photographic material to cover a visible light region and the other is a chemical sensitizer capable of increasing light sensitiveness independently from the sensible wave length region. The sensitizers of the former group may be sensitizing dyes known in the photographic arts, e.g. acridine dyes, cyanine dyes, mellocyanine dyes, styryl dyes, etc. Typical dyesutifs are Acridine Orange, Acridine Red, Rose Bengal, Methylene Blue, Pinacyanol, Pinacryptol Yellow, 1- 3 -ethyl-2 (3H) -benzothiazolidine) 4-butylidene-di-benzothiazolyl methane, 1-ethyl-4-( 1H quinolidene)-ethylidene-di-Z-benzothiazolyl methane, 5-2- (3 ethylbenzoxazolidene) ethylidene 2 phenylimido- 3 phenyl 4 keto tetrahydrothiazole, 1,3 diethylthia 4' carbocyanine iodide, 1,3 dimethyl oxa 2- carbocyanine p toluenesulfonate, 5 1 methyl 2(1H)- quinolidene 2 butylidene 3 ethyl 2 thio 2,4 oxazolidenedione, etc. Useful as the sensitizers of the second group are the following aldehydes: benzaldehyde, dimethylaminobenzaldehyde, ortho-phthaldialdehyde, salicylaldehyde, thiosalicylaldehyde, anisaldehyde, vanilline, phenylacetaldehyde, o-chlorobenzaldehyde, ascorbic acid, benzaldehyde sulfonate, etc. 4-Methylquinoline N-oxide, 2,2'-dipyridine N-oxide disulfide and quinoline N-oxide also are useful. By suitable use of these sensitizers, it is possible to have light sensitiveness increased by 2 to 20 times.

A thermal fixing agent is the preferred component to be compounded with a sensitizer. A light-sensitive, photographic material of the present invention is subjected to fixation by heating or solvent treatment after printing. In a case of thermal fixation being employed, incorporation of a thermal fixing agent will enhance fixing effect so as to provide a more stable image..Suitable thermal fixing agents are phthalic anhydride, maleic anhydride, succinic anhydride and other anhydrides, and benzoic acid, phenylacetic acid, phenoxyacetic acid, phthalaldehydic acid, palmitic acid, stearic acid and other organic acid. These thermal fixing agents may be added to a binder solution containing the photoactivator and color modifier. In addition to the above-specified acids or anhydrides, some salts including sodium diethyl-dithiocarbamate, sodium sulfite, sodium metaborate, sodium carbonate, sodium salicylate, sodium oxalate, etc. also are effective as thermal fixing agents. However, these salts can not be added directly to the binder solution and they should be prepared as a separate OJ-5% aqueous solution which is then overcoated onto the light-sensitive layer of a light-sensitive, photographic material of the present invention.

A light-sensitive, photographic material of the invention, as stated previously, can be prepared by dissolving the above-mentioned various ingredients into a binder solution and then applying the resulting solution to a suitable support in the manner known in the art. The weight proportions of these ingredients as required are as follows:

Parts Solvent 500-1,000 Film-forming binder 1 20-100 Photo-activator 1-50 Color modifier 10-100 Thermal fixing agent (optional) 5-10 Sensitizer (optional) l-5 The amount of binder should be as most 10% based on the Weight of solvent.

Papers, plastic film bases, glass plates, metal plates, etc. are usable as supports. However, photographic papers and plastic coated papers are preferred because the resulting light-sensitive photographic material can produce a clear image with high resolution and high density. A clear transparent image can be obtained by coating the solution onto a photographic film base. The amount of a lightsensitive layer to be coated on a support generally will be 23,u. in thickness. Higher light-sensitiveness and higher density can be obtained by increasing thickness of the said layer.

A light-sensitive, photographic material of the invention is subjected to printing operation by exposing through an image-bearing original to light, whereby a clear image is developed through color change or decolorization. Light sensitiveness of the material is several to several ten times high as compared with that of a commercially available diazotype copying sheet. If necessary, the enlarged image of an original can be obtained :by means of a suitable apparatus. The printed image is stable, but it should be fixed because said image can not be stored in a light place unless the light sensitiveness remaining at the nonexposed area is nullified. Fixation can be effected by heating, after printing, the light-sensitive, photographic material so to stabilize the residual photo-activator and color modifier. Alternatively, the said material can be treated with a solvent thereby to remove the above-said components. Thermal fixation is conveniently carried out by passing the photographic material between hot rolls having a surface temperature of to C. Solvent fixation can be made by using a suitable solvent which does not dissolve the remaining and resulting coloring components but dissolve the photo-activator. For example, an equal amount mixture of ethyl acetate and cyclohexanone is most preferred for a nega-posi type lightsensitive, photographic material in which the photoactivator is the compound (3) as mentioned before and the color modifier is diphenylamine. Trichlene, methanol, acetone and the like solvent are not suitable for the same photographic material because these solvents dissolve the coloring matters as formed. It should be noted that a solvent used for solvent fixation is properly selected depending on the components of a light-sensitive photographic material. If a suitable solvent is used, solvent fixation will be complete within 0.5-2 minutes.

Now the following examples will be given to show the present invention in detail.

EXAMPLE 1 A photographic paper is coated with polyvinyl alcohol having a polymerization degree of about 600 at thickness of 1-1.5 g./m. To the photographic paper thus surfacetreated, a light-sensitive solution is coated at the amount of 20 cc./m. under safe yellow light, said solution having the following formulation:

Hexabromodimethyl sulfone-S g. Diphenyl amine-5 g.

Acetyl cellulose-10 g. Acetone-30 cc.

Benzene-70 cc.

EXAMPLE 2 A light-sensitive, printing-out type photographic maerial is prepared in the same manner as in Example 1, H112 using p,p'-benzylidene-bis (N,N-dimethyl aniline) (i.e. .euko compound of Malakite Green) instead of the diuhenylamine used in Example 1. The photographic maerial yields a clear bluish green image on White background by treating said material in the same manner as [1 Example 1. This photographic material is of the nega- IOSi type, and so it can provide either a positive image r a negative one depending on whether the used original s a photographic negative or positive respectively.

EXAMPLE 3 A light-sensitive solution containing a sensitizer is preared, the formulation of which is as follows:

exabromodimethyl sulfone-S g. Diphenyl aminel g. x-Dimethylaminobenzaldehyde-1 g. Dellulose acetate butyrate10 g. \cetone30 cc.

Benzene-J0 cc.

lhe light-sensitive solution is coated at the amount of 20 :c./m. onto a photographic cellulose triacetate film base )f 0.14 mm. thick under yellow safe light in the manner mown per se. The coated film base is then dried in a lark room at a temperature of less than 60 0., thereby o obtain a light-sensitive printing-out type photographic material which can produce a satisfactorily dense, clear :olor image by one-second exposure when printing is dfected by using the same light source as in Example 1.

EXAMPLE 4 To the same photographic paper as used in Example 1, a ight-sensitive solution is coated at the amount of 15 :c./m. the formulation of said solution being as follows:

['ribromomethylphenyl sulfone-S g.

LN-dihydroxyethylaniline5 g.

t/laleic anhydride1.5 g.

laran F 220 (vinyliden chlorideacrylonitrile copolymer resin)-5 g.

rcetone100 cc.

lfter drying, a desired light-sensitive, printing-out type thotographic material is obtained. This material is exosed in the same manner as in Example 1, whereby a lear blue image is developed on white background. By assing the material between hot rolls having a surface emperature of 150 C., the formed image is fixed. The mage is so stable that no appreciable change is observed :ven by exposure to intense ultraviolet irradiation.

EXAMPLE 5 A light-sensitive, printing-out type photographic mateial is prepared by coating a light-sensitive solution at the amount of 20 cc./m. onto a photographic paper, the formulation of said solution being as follows:

2,5-dimethyl 4 chlorophenyl-trichloromethyl sulfone- Diphenyl amine10 g.

Acridine Orange0.1 g.

Maleic anhydride1.5 g.

Polyvinyl acetate-2 g.

Acetone-1OO cc.

The photographic material which contains the dye as color sensitizer has a broad sensitivity to cover a visible light region and is more sensitive by ten times than the photographic material of Example 1. The photographic material of this example can provide a clear blue image when imagewise exposure is made at a distance of 30 cm. for 15-20 seconds by means of a slide projector bearing a photographic negative and using a tungsten lamp as light source. Fixation is achieved by passing the material between hot rolls having a surface temperature of C., thereby to give a stable image with good resolution.

EXAMPLE 6 A light-sensitive, bleaching-out type photographic material is prepared by coating a light-sensitive solution at the amount of 16 cc./m. onto a photographic paper, the formulation of said solution being as follows:

Hexabromodimethylsulfoxide10 g.

2 Carbostearylamino-4-pdihydroxyethylaminophenylimino-naphthoquinone1 g.

Cellulose acetate-5 g.

Acetone-7O cc.

Methanol-30 cc.

The photographic material is of the posi-posi type, and it can give a clear bluish green image when said material is exposed through an original to irradiation at a distance 30 cm. from a 300 watt-xenon lamp for 2 minutes. The resulting image can be fixed to a stable image with good resolution by immersion with an equal mixture of ethyl acetate and cyclohexane for one minute.

EXAMPLE 7 A light-sensitive printing-out type photographic material is prepared by coating a light-sensitive solution at the amount of 20 cc./m. onto a photographic paper, the formulation of said solution being as follows:

Pentabromodimethyl sulfoxide-IO g. N-vinyl carbazole10 g.

Cellulose acetate-5 g.

Acetone-50 cc.

Benzene-50 cc.

The photographic material when exposed to light gives a pale pellow image, the density of which can be remarkably increased by thermal fixation. For example, the photographic material after printing is passed between hot rolls having a surface temperature of 150 C. thereby to have a density increase up to five timeslf such density increase is taken into consideration, the photographic material of this example is more sensitive by about 50100 times than that of Example 1. Resolution of the resulted image also is excellent.

What is claimed is:

1. A light-sensitive, photographic material which comprises a support bearing a light-sensitive layer comprising a photo-activator capable of generating a free radical by the action of light and an organic compound which reacts with the said free radicals to produce a color change, said photo-activator being a compound the general formula (wherein is hydrogen, chlorine or bromine; Y is hydrogen, chlorine or bromine; Z is chlorine or bromine; and R 9 is non-substituted or substituted aryl group, heterocyclic group or a group R1 CR2 in which R R and R individually are hydrogen, chlorine or bromine.

2. A light-sensitive, photographic material as claimed in claim 1, further comprising an optical sensitizer selected from the group consisting of acridine dyes, cyanine dyes, mellocyanine dyes and styryl dyes.

3. A light-sensitive, photographic material as claimed in claim 1, further comprising a chemical sensitizer selected from the group consisting of benzaldehyde, dimethylaminobenzaldehyde, ortho-phthaldehyde, salicylaldehyde, thiosalicylaldehyde, anisaldehyde, vanilline, phenyle acetaldehyde, o-chlorobenzaldehyde, ascorbic acid, benzaldehyde sulfonate, 4-methylquinoline N-oxide, 2,2'-dipyridine N-oxide disulfide and quinoline N-oxide.

4. A light-sensitive, photographic material as claimed in claim 1, further comprising a thermal fixing agent selected from the group consisting of phthalic anhydride, malic anhydride, succinic anhydride, benzoic acid, phenylacetic acid, phenoxyacetic acid, phthalaldehydic acid, palmitic acid and stearic acid.

5. A light-sensitive photographic material as claimed in claim 1, wherein the photo-activator used is at least one compound selected from the group consisting of hexabromodimethyl-sulfoxide, pentabromodimethylsulfoxide, hexabromodimethyl sulfone, trichloromethylphenyl-sulfone, tribromomethyl-phenyl-sulfone, trichloromethyl-p-chloropheny1-sulfone, tribromomethyl pnitrophenyl-sulfone, 2-trichloromethyl-benzothiazolyl-sulfone- (2), 4,6 dimethylpyrimidyl 2 tribromomethyl-sulfone, tetrabromodimethyl-sulfone, 2,4-dichlorophenyl-trichloromethyl-sulfone, 2-methyl-4-ch10rophenyl-trichloromethylsulfone, 2,5 dimethyl 4 chlorophenyl-trichloromethyl sulfone, 2,4-dichlorop11enyl-tribromomethyl-sulfone and bromomethyl-dibromomethy1-sulfone.

6. A light-sensitive, photographic material as claimed in claim 1, wherein the photographic material is of the printing-out type (nega-posi system) and the organic compound used is a compound selected from the group consisting of diphenyl amine, dibenzyl amine, triphenyl amine, N,N-diethyl aniline, N,N-dimethyl aniline, N- hydroxy-N-ethyl aniline, dibenzyl aniline, o-aminodiphenyl amine, p-hydroxydiphenyl amine, N-vinyl carbazole, 2-pheny1 indolidine, N,N-dihydroxyethyl aniline, N,N-dipheny1-p-phenylene diamine, N,N-dihydroxyethylm-toluidine, a-naphthyl amine, p-dimethylamino-benzaldehyde, 3-aminoquinoline, indole, salicylidene-p-toluidine, salicyclidene p-chloroaniline, cyanomethylene-4-quinolyl- Z-naphthalene, 3-phenyl-ind0le, a-diethylaminopyridine, p,p-methylene bis-aniline, p,p'-methy1ene bis-(N,N-dimethylaniline), p,p' -benzylidine bis-(N,N-dimethylaniline), p,p',p-methylidine tris-(N,N-diethylaniline), p,p'- hydroxy-methylene bis(N,N-dimethylaniline), p,p'-(dimethylamino) diphenyl amino, p,p'-aminomethylene-bis (N,N-dimethylaniline), p,p'-(o"-chlorobenzylidene) bis (N,N-dimethylaniline), p,p'-(p"-aminobenzy1i dene) bisaniline, p,p-(p"-amino-m"-methylbenzylidene) bis(N- phenylaniline), 1,1 bis(p-dimethylaminophenol) p'-dimethylaminophthalein, 3,6 bis(diethylamino)spiro (phthalein 1,9 xanthene), 3,6 bis(diethylamino)-9-(pdimethylaminophenol)xanthene, 1,1-bis(p-dimethylaminophenol) p dimethylaminophthalane, 1,1 bis(p-aminophenol) p-aminophenol-phthalane, 10-benzoy1-3,7-di(pdimethylamino) phenothiazine, 10 cinnamoyl-3,7-di(pdimethylamino) phenothiazine and 3 diethylamino-7- aminophenoxazine; the quarternary salts of Z-methylbenzthiazole methyl iodide, 2-methylbenzthiazole ethyl bromide, quinardine methyl iodide, 2,5-dimethylbenzthiazole methyl-p-toluenesulfonate and 2,5,6-trimethylbenzthiazole butyl iodide; as well as 4-methylquinoline N- oxide, 2,2'-dipyridine N-oxide disulfide and quinoline N- oxide.

7. A light-sensitive photographic material as claimed in claim 1, wherein the photographic material is of the bleaching-out type (posi-posi system) and the organic compound used is a compound selected from the group consisting of Orlamin (C.I. 41000), Victoria Blue (0.1. 44045), Victoria Blue R (CI. 44040), Brilliant Lowdurine Blue (C.I. 42565), Benzoyl Methylene Blue, Cinnamoyl Methylene Blue, p-Anisoyl Methylene Blue, New Methylene Blue (CI. 51195), Nile Blue A (CI. 51180), Ephitenew Blue (01. 51185), Rhodamine B (CI. 45170), Rhodamine 3B (CI. 45175), Rhodamine 12 GM (CI. 45310), Sudan Brau G (01. 61525), Sudan Blue GN (CI. 61520), Celliton Blue (CI. 64500), 4-p-diethylaminophenylimino-naphthoquinone, 2-carboxyanilino-4- p diethylaminophenylimino naphthoquinone, 2 carbostearylamino 4-p dihydroxyethyl-aminopheny-liminonophthoquinone, p methoxybenzoyl p-diethylamino-omethylphenylimino acetanilide, cyano-p-diethylaminophenylimino-acetanilide, 1-phenyl-3-methyl 4-p-diethylaminophenylimino S-pyrazolone and l-B-naphthyl-B- methyl-4-p-diethylaminophenylimino-5-pyrazolone.

OTHER REFERENCES Soviet Inventions Illustrated, Preparation of Di-(Trichloro-methyl)-Sulphone, Pub. 3-1966, pp. 5, 16.

NORMAN G. TORCHIN, Pn'mary Examiner WON H. LOUIE, JR., Assistant Examiner US. Cl. X.R. 96-48

US3502476A 1965-10-20 1966-10-11 Light-sensitive photographic materials Expired - Lifetime US3502476A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP6406965 1965-10-20

Publications (1)

Publication Number Publication Date
US3502476A true US3502476A (en) 1970-03-24

Family

ID=13247420

Family Applications (1)

Application Number Title Priority Date Filing Date
US3502476A Expired - Lifetime US3502476A (en) 1965-10-20 1966-10-11 Light-sensitive photographic materials

Country Status (5)

Country Link
US (1) US3502476A (en)
BE (1) BE688466A (en)
DE (1) DE1572089A1 (en)
GB (1) GB1163324A (en)
NL (1) NL6614847A (en)

Cited By (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3765883A (en) * 1970-02-04 1973-10-16 Canon Kk Organic photoconductors sensitized with free radical liberators and organometallic compounds
US3767399A (en) * 1970-12-19 1973-10-23 Asahi Chemical Ind Photosensitive composition containing an aldol naphthylamine as color former and a halogenated hydrocarbon as photoactivator
US3775123A (en) * 1970-11-05 1973-11-27 Asahi Chemical Ind PHOTOSENSITIVE MATERIAL CONTAINING A p-PHENYLENEDIAMINE DERIVATIVE COLOR FORMER AND A HALOGENATED HYDROCARBON PHOTOACTIVATOR
US3847607A (en) * 1970-02-04 1974-11-12 Canon Kk Organic photoconductors sensitized by free radical liberators and organometallic compounds
US3907569A (en) * 1973-01-31 1975-09-23 Horizons Inc Ultraviolet holdback of nonsilver photosensitive systems by incorporating therein certain organic additives
US3923521A (en) * 1973-01-31 1975-12-02 Horizons Inc Ultraviolet holdback of nonsilver photosensitive systems by incorporating therein certain organic additives
US3935012A (en) * 1973-07-12 1976-01-27 Minnesota Mining And Manufacturing Company Photosensitive sheet materials
US3941598A (en) * 1972-07-10 1976-03-02 Agfa-Gevaert N.V. Complexing residual photosensitive polyhalogen compound with the tertiary amine
US3988159A (en) * 1967-07-28 1976-10-26 American Can Company Light-sensitive material containing nitrone for forming heat-fixed images
US4030926A (en) * 1974-07-11 1977-06-21 Agfa-Gevaert, A.G. Light-sensitive material containing a dye-forming combination of a heterocyclic compound and a cyclic dihalodicarbonyl compound in a polymeric binder
US4039332A (en) * 1973-09-20 1977-08-02 Agfa-Gevaert N.V. Stabilization of photosensitive recording material
US4042388A (en) * 1972-03-15 1977-08-16 Canon Kabushiki Kaisha Process for the preparation of sensitized material for electrophotography
WO1980001322A1 (en) * 1978-12-20 1980-06-26 Eastman Kodak Co Imaging composition featuring aromatic dialdehyde-retaining binders
US4251622A (en) * 1973-05-25 1981-02-17 Nippon Paint Co., Ltd. Photo-sensitive composition for dry formation of image
US4252884A (en) * 1979-08-14 1981-02-24 James River Graphics, Inc. Negative-working diazotype photoreproduction
US4263395A (en) * 1976-11-18 1981-04-21 Agfa-Gevaert N.V. High intensity photon-image recording
US4271251A (en) * 1978-10-19 1981-06-02 Fuji Photo Film Co., Ltd. Photosensitive compositions
US4368254A (en) * 1979-08-20 1983-01-11 Vannikov Anatoly V Non-silver light-sensitive composition
US4370401A (en) * 1979-12-07 1983-01-25 Minnesota Mining And Manufacturing Company Light sensitive, thermally developable imaging system
US4386154A (en) * 1981-03-26 1983-05-31 Minnesota Mining And Manufacturing Company Visible light sensitive, thermally developable imaging systems
US4460677A (en) * 1981-03-26 1984-07-17 Minnesota Mining And Manufacturing Company Visible light sensitive, thermally developable imaging systems
US4705729A (en) * 1984-11-19 1987-11-10 Hewlett-Packard Company Method for photochemically enhancing resolution in photolithography processes
US5312721A (en) * 1991-12-24 1994-05-17 E. I. Du Pont De Nemours And Company Bleachable antihalation system
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
US5685754A (en) * 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and polymer coating applications therefor
US5700850A (en) 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
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
US6486227B2 (en) 2000-06-19 2002-11-26 Kimberly-Clark Worldwide, Inc. Zinc-complex 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
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3907954A1 (en) * 1989-03-11 1990-09-13 Hoechst Ag A positive-working radiation-sensitive mixture and made therefrom, radiation-sensitive recording material for high-energy radiation
DE3907953A1 (en) * 1989-03-11 1990-09-13 Hoechst Ag The radiation-curable mixture prepared therefrom and radiation-sensitive recording material for high-energy radiation
DE3930086A1 (en) * 1989-09-09 1991-03-21 Hoechst Ag A positive-working radiation-sensitive mixture and made therefrom, radiation-sensitive recording material
DE3930087A1 (en) * 1989-09-09 1991-03-14 Hoechst Ag A positive-working radiation-sensitive mixture and made therefrom, radiation-sensitive recording material
DE4006190A1 (en) * 1990-02-28 1991-08-29 Hoechst Ag A negative-working radiation-sensitive mixture and made therefrom, radiation-sensitive recording material
DE4112968A1 (en) * 1991-04-20 1992-10-22 Hoechst Ag Acid-cleavable compounds, those containing positive working radiation-sensitive mixture and produced therefrom radiation-sensitive recording material
US5369000A (en) * 1993-04-29 1994-11-29 Minnesota Mining And Manufacturing Company Post-processing stabilizers for photothermographic articles

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3121633A (en) * 1962-07-25 1964-02-18 Horizons Inc Process of making print-out images with cyanine dye bases and styryl dye bases

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3121633A (en) * 1962-07-25 1964-02-18 Horizons Inc Process of making print-out images with cyanine dye bases and styryl dye bases

Cited By (81)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3988159A (en) * 1967-07-28 1976-10-26 American Can Company Light-sensitive material containing nitrone for forming heat-fixed images
US3847607A (en) * 1970-02-04 1974-11-12 Canon Kk Organic photoconductors sensitized by free radical liberators and organometallic compounds
US3765883A (en) * 1970-02-04 1973-10-16 Canon Kk Organic photoconductors sensitized with free radical liberators and organometallic compounds
US3775123A (en) * 1970-11-05 1973-11-27 Asahi Chemical Ind PHOTOSENSITIVE MATERIAL CONTAINING A p-PHENYLENEDIAMINE DERIVATIVE COLOR FORMER AND A HALOGENATED HYDROCARBON PHOTOACTIVATOR
US3767399A (en) * 1970-12-19 1973-10-23 Asahi Chemical Ind Photosensitive composition containing an aldol naphthylamine as color former and a halogenated hydrocarbon as photoactivator
US4042388A (en) * 1972-03-15 1977-08-16 Canon Kabushiki Kaisha Process for the preparation of sensitized material for electrophotography
US3941598A (en) * 1972-07-10 1976-03-02 Agfa-Gevaert N.V. Complexing residual photosensitive polyhalogen compound with the tertiary amine
US3907569A (en) * 1973-01-31 1975-09-23 Horizons Inc Ultraviolet holdback of nonsilver photosensitive systems by incorporating therein certain organic additives
US3923521A (en) * 1973-01-31 1975-12-02 Horizons Inc Ultraviolet holdback of nonsilver photosensitive systems by incorporating therein certain organic additives
US4251622A (en) * 1973-05-25 1981-02-17 Nippon Paint Co., Ltd. Photo-sensitive composition for dry formation of image
US3935012A (en) * 1973-07-12 1976-01-27 Minnesota Mining And Manufacturing Company Photosensitive sheet materials
US4039332A (en) * 1973-09-20 1977-08-02 Agfa-Gevaert N.V. Stabilization of photosensitive recording material
US4030926A (en) * 1974-07-11 1977-06-21 Agfa-Gevaert, A.G. Light-sensitive material containing a dye-forming combination of a heterocyclic compound and a cyclic dihalodicarbonyl compound in a polymeric binder
US4263395A (en) * 1976-11-18 1981-04-21 Agfa-Gevaert N.V. High intensity photon-image recording
US4271251A (en) * 1978-10-19 1981-06-02 Fuji Photo Film Co., Ltd. Photosensitive compositions
WO1980001322A1 (en) * 1978-12-20 1980-06-26 Eastman Kodak Co Imaging composition featuring aromatic dialdehyde-retaining binders
US4247625A (en) * 1978-12-20 1981-01-27 Eastman Kodak Company Imaging processes, elements and compositions featuring dye-retaining binders for reaction products of cobalt complexes and aromatic dialdehyde
US4252884A (en) * 1979-08-14 1981-02-24 James River Graphics, Inc. Negative-working diazotype photoreproduction
US4368254A (en) * 1979-08-20 1983-01-11 Vannikov Anatoly V Non-silver light-sensitive composition
US4370401A (en) * 1979-12-07 1983-01-25 Minnesota Mining And Manufacturing Company Light sensitive, thermally developable imaging system
US4386154A (en) * 1981-03-26 1983-05-31 Minnesota Mining And Manufacturing Company Visible light sensitive, thermally developable imaging systems
US4460677A (en) * 1981-03-26 1984-07-17 Minnesota Mining And Manufacturing Company Visible light sensitive, thermally developable imaging systems
US4705729A (en) * 1984-11-19 1987-11-10 Hewlett-Packard Company Method for photochemically enhancing resolution in photolithography processes
US5312721A (en) * 1991-12-24 1994-05-17 E. I. Du Pont De Nemours And Company Bleachable antihalation system
US5700850A (en) 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
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
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5683843A (en) * 1993-08-05 1997-11-04 Kimberly-Clark Corporation Solid colored composition mutable by ultraviolet radiation
US5908495A (en) 1993-08-05 1999-06-01 Nohr; Ronald Sinclair Ink for ink jet printers
US5858586A (en) 1993-08-05 1999-01-12 Kimberly-Clark Corporation Digital information recording media and method of using same
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
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
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of 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
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US6127073A (en) 1993-08-05 2000-10-03 Kimberly-Clark Worldwide, Inc. Method for concealing information and document for securely communicating concealed information
US6054256A (en) 1993-08-05 2000-04-25 Kimberly-Clark Worldwide, Inc. Method and apparatus for indicating ultraviolet light exposure
US6120949A (en) 1993-08-05 2000-09-19 Kimberly-Clark Worldwide, Inc. Photoerasable paint and method for using photoerasable paint
US5616443A (en) * 1993-08-05 1997-04-01 Kimberly-Clark Corporation Substrate having a mutable colored composition thereon
US6066439A (en) 1993-08-05 2000-05-23 Kimberly-Clark Worldwide, Inc. Instrument for photoerasable marking
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
US5686503A (en) * 1994-06-30 1997-11-11 Kimberly-Clark Corporation 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
US5685754A (en) * 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and polymer coating 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
US5798015A (en) * 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5747550A (en) * 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5849411A (en) * 1995-06-05 1998-12-15 Kimberly-Clark Worldwide, Inc. Polymer film, nonwoven web and fibers containing a photoreactor composition
US6063551A (en) 1995-06-05 2000-05-16 Kimberly-Clark Worldwide, Inc. Mutable dye composition and method 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
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
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable 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
US5782963A (en) 1996-03-29 1998-07-21 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
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
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
US6486227B2 (en) 2000-06-19 2002-11-26 Kimberly-Clark Worldwide, Inc. Zinc-complex photoinitiators and applications therefor

Also Published As

Publication number Publication date Type
BE688466A (en) 1967-04-19 grant
DE1572089A1 (en) 1970-12-23 application
GB1163324A (en) 1969-09-04 application
NL6614847A (en) 1967-04-21 application

Similar Documents

Publication Publication Date Title
US3666466A (en) Deactivating dual response photosensitive compositions with visible and ultraviolet light
US3536489A (en) Heterocyclic iminoaromatic-halogen containing photoinitiator light sensitive compositions
US3369905A (en) Photographic silver halide emulsions containing polyamine sensitizing agents
US3697280A (en) Hexaarylbiimidazole-selected aromatic hydrocarbon compositions
US3533794A (en) Color photographic light-sensitive material containing ultraviolet absorbing agents
US3595657A (en) Non-silver direct positive dye bleachout system using indigoid dyes and colorless activators
US3595655A (en) Non-silver direct positive dyes bleachout system using polymethine dyes and colorless activators
US3640718A (en) Spectral sentization of photosensitive compositions
US3579339A (en) Photopolymerizable dispersions and elements containing nonmigratory photoreducible dyes
US4306014A (en) Photo-sensitive and heat-sensitive composition and recording element using same
US3300314A (en) Nonsilver, light-sensitive photographic elements
US4311783A (en) Dimers derived from unsymmetrical 2,4,5,-triphenylimidazole compounds as photoinitiators
US4632895A (en) Diffusion or sublimation transfer imaging system
US3841880A (en) Silver halide emulsion containing ketomethylene photographic color-forming couplers
US5055373A (en) Multicolor recording material
US3832212A (en) Heat-sensitive copying systems
US3652275A (en) HEXAARYLBIIMIDAZOLE BIS (p-DIALKYL-AMINOPHENYL-{60 ,{62 -UNSATURATED) KETONE COMPOSITIONS
US3954475A (en) Photosensitive elements containing chromophore-substituted vinyl-halomethyl-s-triazines
US5314795A (en) Thermal-dye-bleach construction comprising a polymethine dye and a thermal carbanion-generating agent
US5258274A (en) Thermal dye bleach construction sensitive to ultraviolet radiation
US3390996A (en) Photosensitive composition comprising an organic nitrogen-containing color-generator, a photo-oxidant and a redox couple
US3140949A (en) Printout process and leuco bases of triphenyl methane dyes used therein
US3667959A (en) Photosensitive and thermosensitive element,compositions and process
US3383212A (en) Photographic process utilizing composition comprising an oxidatively activatable color generator, thermally activatable oxidant and a redox couple
US4395484A (en) Roomlight-stable ultraviolet-response photothermographic imaging material