JPH0420172B2 - - Google Patents

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Publication number
JPH0420172B2
JPH0420172B2 JP58045699A JP4569983A JPH0420172B2 JP H0420172 B2 JPH0420172 B2 JP H0420172B2 JP 58045699 A JP58045699 A JP 58045699A JP 4569983 A JP4569983 A JP 4569983A JP H0420172 B2 JPH0420172 B2 JP H0420172B2
Authority
JP
Japan
Prior art keywords
group
general formula
formula
silver halide
alkyl group
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
JP58045699A
Other languages
Japanese (ja)
Other versions
JPS59171953A (en
Inventor
Toyoki Nishijima
Shun Takada
Kaoru Onodera
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 Minolta Inc
Original Assignee
Konica Minolta Inc
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
Application filed by Konica Minolta Inc filed Critical Konica Minolta Inc
Priority to JP4569983A priority Critical patent/JPS59171953A/en
Publication of JPS59171953A publication Critical patent/JPS59171953A/en
Publication of JPH0420172B2 publication Critical patent/JPH0420172B2/ja
Granted legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/3003Materials characterised by the use of combinations of photographic compounds known as such, or by a particular location in the photographic element
    • G03C7/3005Combinations of couplers and photographic additives
    • G03C7/3006Combinations of phenolic or naphtholic couplers and photographic additives

Description

〔処理工程〕[Processing process]

発色現像(33℃、3分)−漂白定着(33℃、1
分30秒)−水洗(33℃、2分) 〔発色現像液組成物〕 4−アミノ−3−メチル−N−エチル−N−
(β−メチルスルホンアミドエチル)−アニリン硫
酸塩 5.0g ベンジルアルコール 15ml ヘキサメタリン酸ナトリウム 2.5g 無水亜硫酸ナトリウム 2.0g 無水亜硫酸ナトリウム 2.0g 臭化カリウム 1.2g ホウ砂 38g 水を加えて1とし水酸化ナトリウムを用いて
PH10.30に調整する。 〔漂白定着液組成〕 エチレンジアミンテトラ酢酸鉄アンモニウム
60g エチレンジアミンテトラ酢酸2アンモニウム塩
5.0g チオ硫酸アンモニウム 120g メタ重亜硫酸ナトリウム 13g 無水亜硫酸ナトリウム 3.0g 水を加えて1とする。 処理後に得られた試料について分光吸収特性お
よび色素画像保存性の試験を以下の要領で行なつ
た。 (分光吸収特性) 反射分光光度計(日立カラーアナライザー607
型)を用いて反射濃度が極大となる波長(極大吸
収波長:〓〓max)を測定した。 (画像保存性試験) () 耐光性 各色素画像を45000ルツクスの照度のキセノ
ンフエードメーターを用いて初濃度1.0部分に
おける250時間曝射した後の、残存濃度を測定
した。 () 初濃度1.0部分における暗所での77℃におけ
る2週間保存後の残存濃度を測定した。 以上の試験結果を表1に示した。
Color development (33℃, 3 minutes) - Bleach fixing (33℃, 1 minute)
minutes 30 seconds) - Water washing (33°C, 2 minutes) [Color developer composition] 4-amino-3-methyl-N-ethyl-N-
(β-Methylsulfonamidoethyl)-aniline sulfate 5.0g Benzyl alcohol 15ml Sodium hexametaphosphate 2.5g Anhydrous sodium sulfite 2.0g Anhydrous sodium sulfite 2.0g Potassium bromide 1.2g Borax 38g Add water to 1 and add sodium hydroxide. make use of
Adjust to PH10.30. [Bleach-fix solution composition] Ethylenediaminetetraacetate iron ammonium
60g Ethylenediaminetetraacetic acid diammonium salt
5.0g Ammonium thiosulfate 120g Sodium metabisulfite 13g Anhydrous sodium sulfite 3.0g Add water to make 1. The samples obtained after the treatment were tested for spectral absorption characteristics and dye image storage stability in the following manner. (Spectral absorption characteristics) Reflection spectrophotometer (Hitachi Color Analyzer 607
The wavelength at which the reflection density becomes maximum (maximum absorption wavelength: 〓〓max) was measured using (Image storage stability test) () Light resistance After each dye image was exposed for 250 hours at an initial density of 1.0 using a xenon fademeter with an illuminance of 45,000 lux, the residual density was measured. () The residual concentration at the initial concentration of 1.0 was measured after storage for 2 weeks at 77°C in the dark. The above test results are shown in Table 1.

【表】 第1表の結果から明らかな様に、高沸点有機溶
媒として一般式〔〕又は一般式〔〕又は一般
式〔〕で表わされる化合物のみをそれぞれ単独
で用いた試料に比べて、本発明の試料である一般
式〔〕又は一般式〔〕の化合物と一般式
〔〕の化合物を組み合わせたものはシアン色素
画像の暗退色性を損なわず、耐光性が向上しか
つ、最大吸収波長が長波化し、分光吸収特性の良
好な発色色素画像が得られる。例えば高沸点有機
溶媒としてジブチルフタレート(−38)のみを
用いた場合、ジオクチルフタルート(−2)の
みを用いた場合より、吸収最大波長が長波化する
が、耐光性を劣化する。ところがジブチルフタレ
ートとフエノール計高沸点有機溶媒を併用すれば
吸収極大波長が長波化するだけでなく耐光性も向
上する。また、暗退色性も劣化しない。係る効果
は本発明に係る高沸点有機溶媒の組み合せで、は
じめて得られるものであり予期しえない相乗効果
によるものである。 実施例 2 第2表に示す種々のシアンカプラーと高沸点有
機溶媒の組合せで試料No.16乃至No.24を実施例1と
同様の方法で作致し、画像保存性および分光吸収
特性を測定した。
[Table] As is clear from the results in Table 1, compared to samples in which only the compound represented by general formula [] or general formula [] or general formula [] was used alone as a high-boiling organic solvent, this The invention sample, which is a combination of general formula [] or a compound of general formula [] and a compound of general formula [], does not impair dark fading properties of cyan dye images, improves light fastness, and has a maximum absorption wavelength. The wavelength becomes longer and a colored dye image with good spectral absorption characteristics can be obtained. For example, when only dibutyl phthalate (-38) is used as the high-boiling organic solvent, the maximum absorption wavelength becomes longer than when only dioctyl phthalate (-2) is used, but the light resistance deteriorates. However, if dibutyl phthalate and a phenolic high boiling point organic solvent are used together, not only the maximum absorption wavelength becomes longer but also the light resistance improves. Furthermore, the dark fading property does not deteriorate. Such an effect can only be obtained by combining the high boiling point organic solvents according to the present invention, and is due to an unexpected synergistic effect. Example 2 Samples No. 16 to No. 24 were prepared using the combinations of various cyan couplers shown in Table 2 and high-boiling organic solvents in the same manner as in Example 1, and the image storage properties and spectral absorption characteristics were measured. .

【表】 第2表から明らかな様に、シアンカプラーとし
て一般式〔〕で示される化合物を用い、高沸点
有機様媒として一般式〔〕又は〔〕で示され
る化合物と一般式〔〕の化合物を組み合せた試
料は、シアン色素画像の暗退色性を損なわず耐光
性が向上しかつ最大吸収波長が長波化し分光吸収
特性の良好な発色色素画像が得られた。かかる画
像保存性および分光吸収特性に関する効果は、本
発明に係るシアンカプラーと高沸点有機溶媒の組
合せにおいてはじめて達成されるものである。 実施例 3 ポリエチレン被覆紙からなる支持体上に下記の
各層を支持体側より順次塗設し、カラー写真感光
材料を作成し試料番号27とした。 第1層…黄色カプラー(Y−4)を付量0.8g/
m2、2,4−ジ−t−アミルフエニル−3′,
5′−ジ−t−ブチル−4′−ヒドロキシベンゾエ
ートを付量0.3g/m2、2,5−ジ−オクチル
ハイドロキノンを付量0.02g/m2、青感性塩臭
化銀乳剤(銀に換算して)0.3g/m2、高沸点
溶媒(−2)を付量0.6ml/m2、及びゼラチ
ンを付量1.6g/m2となるように塗設した。 第2層…2,5−ジオクチルハイドロキノンを付
量80ml/m2、及びゼラチンを0.4g/m2となる
ように塗設した中間層。 第3層…マゼンタカプラー(M−4)を0.4g/
m2、縁感性縁臭化銀乳剤(銀に換算して)0.4
g/m2、1,4−ジ−オクトキシ−2,5−ジ
−t−アシルベンゼンを0.2g/m2、高沸点溶
媒(−2)を付量0.3ml/m2、2,5−ジ−
オクチルハイドロキノンを付量0.1g/m2とな
るように塗設した。 第4層…2−(2′−ヒドロキシ−3′,5′−(t−ア
ミル)−フエニル)ベンゾトリアゾールを0.7
g/m2、2,5−ジオクチルハイドロキノンを
付量40mg/m2となるように塗設した中間層。 第5層…シアンカプラー(−20)を付量0.4
g/m2高沸点溶媒(P−6)を付量0.2ml/m2
高沸点溶媒(−38)を付量0.2ml/m2、赤感
性塩臭化銀(銀に換算して)0.3g/m2ゼラチ
ンを付量1.7g/m2となるように塗設した。 第6層…2−(2′−ヒドロキシ−3′,5′−ジ−(t
−アミル)−フエニル)−ベンゾトリアゾールを
付量0.3g/m2となるように塗設した中間層。 第7層…ゼラチンを付量0.9g/m2となるように
塗設した保護層。 次に第5層の高沸点有機溶媒として−38のみ
を使用した以外は試料番号27の試料と同様の構成
によつてカラー写真感光材料を作成し試料番号28
とした。 さらにシアンカプラーとして比較シアンカプラ
ー1高沸点有機溶媒として−38のみを使用した
以外は試料番号27と同様の構成によつて試料を作
成し試料番号29とした。 以上の試料を、実施例1と同様にして露光、現
像処理し、分光吸収特性および画像保存性を測定
した。その結果を第3表に示す。
[Table] As is clear from Table 2, the compound represented by the general formula [] is used as the cyan coupler, and the compound represented by the general formula [] or [] and the compound represented by the general formula [] are used as the high-boiling organic modifier. In the sample in which the cyan dye image was combined, the light resistance was improved without impairing the dark fading property of the cyan dye image, and the maximum absorption wavelength was extended to a longer wavelength, and a colored dye image with good spectral absorption characteristics was obtained. Such effects regarding image storage stability and spectral absorption characteristics are achieved for the first time in the combination of the cyan coupler and high boiling point organic solvent according to the present invention. Example 3 The following layers were sequentially coated on a support made of polyethylene-coated paper from the support side to prepare a color photographic material designated as Sample No. 27. 1st layer...Yellow coupler (Y-4) applied amount 0.8g/
m 2 , 2,4-di-t-amyl phenyl-3',
5'-di-t-butyl-4'-hydroxybenzoate was added in an amount of 0.3 g/m 2 , 2,5-di-octylhydroquinone was added in an amount of 0.02 g/m 2 , a blue-sensitive silver chlorobromide emulsion (on silver) The high boiling point solvent (-2) was applied in an amount of 0.6 ml /m 2 , and the gelatin was applied in an amount of 1.6 g/m 2 . Second layer: an intermediate layer coated with 2,5-dioctylhydroquinone in an amount of 80 ml/m 2 and gelatin in an amount of 0.4 g/m 2 . 3rd layer...Magenta coupler (M-4) 0.4g/
m 2 , edge-sensitive edge silver bromide emulsion (in terms of silver) 0.4
g/m 2 , 1,4-di-octoxy-2,5-di-t-acylbenzene at 0.2 g/m 2 , high boiling point solvent (-2) at 0.3 ml/m 2 , 2,5- G
Octylhydroquinone was applied in an amount of 0.1 g/m 2 . 4th layer...2-(2'-hydroxy-3',5'-(t-amyl)-phenyl)benzotriazole at 0.7
An intermediate layer coated with 2,5 -dioctylhydroquinone at an amount of 40 mg/m 2 . 5th layer...Additional amount of cyan coupler (-20): 0.4
g/m 2 high boiling point solvent (P-6) in an amount of 0.2 ml/m 2 ,
A high boiling point solvent (-38) was applied in an amount of 0.2 ml/m 2 and a red-sensitive silver chlorobromide (in terms of silver) was applied in an amount of 0.3 g/m 2 gelatin was applied in an amount of 1.7 g/m 2 . . 6th layer...2-(2'-hydroxy-3',5'-di-(t
-Amyl)-phenyl)-benzotriazole coated in an amount of 0.3 g/ m2 . 7th layer...Protective layer coated with gelatin at a coating weight of 0.9g/ m2 . Next, a color photographic material was prepared using the same structure as Sample No. 27 except that only -38 was used as the high boiling point organic solvent in the fifth layer.
And so. Comparative Cyan Coupler 1 As a cyan coupler, a sample was prepared in the same manner as Sample No. 27, except that only -38 was used as a high boiling point organic solvent, and designated as Sample No. 29. The above samples were exposed and developed in the same manner as in Example 1, and the spectral absorption characteristics and image storage properties were measured. The results are shown in Table 3.

【表】 第3表から明らかな様に、本発明の試料におい
ては、シアン色素画像の暗退色性、退光性が良好
でありかつ吸収極大波長が長波化し分光吸収特性
の良好な発色色素画像が得られた。 またマクベスカラーチヤートの色再現性を調べ
たところ本発明の試料27では試料28に比べ緑色の
色再現性が良く、鮮明な色素画像が得られた。
[Table] As is clear from Table 3, in the sample of the present invention, the cyan dye image has good dark fading property and light fading property, and the absorption maximum wavelength is longer, and the colored dye image has good spectral absorption characteristics. was gotten. Further, when the color reproducibility of the Macbeth color chart was examined, sample 27 of the present invention had better green color reproducibility than sample 28, and a clear pigment image was obtained.

Claims (1)

【特許請求の範囲】 1 支持体上に少なくとも1層のハロゲン化銀乳
剤層を有するハロゲン化銀写真感光材料におい
て、前記ハロゲン化銀乳剤層中に下記一般式
[]で示される2,5−ジアシルアミノフエノ
ール型シアンカプラーの少なくとも1つが、フエ
ノール系高沸点有機溶媒の少なくとも1つと下記
一般式[]または[]で示される高沸点有機
溶媒の少なくとも1つとを組合せて用いて分散さ
れて含有されていることを特徴とするハロゲン化
銀写真感光材料。 一般式[] [式中、R1はアルキル基を表わし、R2はアルキ
ル基、ヒドロキシル基、アミノスルホンアミド
基、アルキルスルホンアミド基又はアリールスル
ホンアミド基を表わし、R3は水素原子、ハロゲ
ン原子、アルキル基、ヒドロキシル基、シアノ
基、ニトロ基、アルコキシ基、アルキルスルホン
アミド基、アリールスルホンアミド基、アルキル
スルフアモイル基、アリールスルフアモイル基、
アルキルオキシカルボニル基又はアリールオキシ
カルボニル基を表わし、n1は1又は2を表わし、
n2は1〜5の整数を表わし、Zは水素原子または
芳香族第1級アミン系発色現像主薬の酸化体との
反応により離脱し得る基を表わす。] 一般式[] [式中、R4およびR5は、それぞれアルキル基、
アルケニル基、シクロアルキル基、またはアリー
ル基を表わす。] 一般式[] [式中、R6、R7およびR6は、それぞれアルキル
基、アルケニル基、シクロアルキル基、またはア
リール基を表わす。] 2 フエノール系高沸点有機溶媒が、下記一般式
[]で示される化合物である特許請求の範囲第
1項記載のハロゲン化銀写真感光材料。 一般式[] [式中、R9、R10、R11、R12、及びR13は、それ
ぞれ水素原子、アルキル基、シクロアルキル基、
またはアリール基を表わす。] 3 フエノール系高沸点有機溶媒が、下記一般式
[]で示される化合物である特許請求の範囲第
2項記載のハロゲン化銀写真感光材料。 一般式[] [式中、R14およびR15は、それぞれ水素原子ま
たは炭素原子数1〜20個のアルキル基を表わす。
R16は炭素原子数1〜20個のアルキル基またはシ
クロアルキル基を表わす。但し、R14、R15およ
びR16で表わされるる基の炭素原子数の総和は6
乃至24個である。]
[Scope of Claims] 1. A silver halide photographic material having at least one silver halide emulsion layer on a support, in which a 2,5- compound represented by the following general formula [] is present in the silver halide emulsion layer. At least one diacylaminophenol type cyan coupler is dispersed and contained using a combination of at least one phenolic high-boiling organic solvent and at least one high-boiling organic solvent represented by the following general formula [] or []. A silver halide photographic material characterized by: General formula [] [In the formula, R 1 represents an alkyl group, R 2 represents an alkyl group, a hydroxyl group, an aminosulfonamide group, an alkylsulfonamide group, or an arylsulfonamide group, and R 3 represents a hydrogen atom, a halogen atom, an alkyl group, Hydroxyl group, cyano group, nitro group, alkoxy group, alkylsulfonamide group, arylsulfonamide group, alkylsulfamoyl group, arylsulfamoyl group,
represents an alkyloxycarbonyl group or an aryloxycarbonyl group, n 1 represents 1 or 2,
n 2 represents an integer from 1 to 5, and Z represents a hydrogen atom or a group capable of being separated by reaction with an oxidized product of an aromatic primary amine color developing agent. ] General formula [] [In the formula, R 4 and R 5 are each an alkyl group,
Represents an alkenyl group, a cycloalkyl group, or an aryl group. ] General formula [] [In the formula, R 6 , R 7 and R 6 each represent an alkyl group, an alkenyl group, a cycloalkyl group, or an aryl group. 2. The silver halide photographic material according to claim 1, wherein the phenolic high-boiling organic solvent is a compound represented by the following general formula []. General formula [] [In the formula, R 9 , R 10 , R 11 , R 12 , and R 13 are each a hydrogen atom, an alkyl group, a cycloalkyl group,
Or represents an aryl group. ] 3. The silver halide photographic material according to claim 2, wherein the phenolic high-boiling organic solvent is a compound represented by the following general formula []. General formula [] [In the formula, R 14 and R 15 each represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
R 16 represents an alkyl group or a cycloalkyl group having 1 to 20 carbon atoms. However, the total number of carbon atoms in the groups represented by R 14 , R 15 and R 16 is 6.
There are 24 to 24 pieces. ]
JP4569983A 1983-03-18 1983-03-18 Silver halide photosensitive material Granted JPS59171953A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP4569983A JPS59171953A (en) 1983-03-18 1983-03-18 Silver halide photosensitive material

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP4569983A JPS59171953A (en) 1983-03-18 1983-03-18 Silver halide photosensitive material

Publications (2)

Publication Number Publication Date
JPS59171953A JPS59171953A (en) 1984-09-28
JPH0420172B2 true JPH0420172B2 (en) 1992-03-31

Family

ID=12726619

Family Applications (1)

Application Number Title Priority Date Filing Date
JP4569983A Granted JPS59171953A (en) 1983-03-18 1983-03-18 Silver halide photosensitive material

Country Status (1)

Country Link
JP (1) JPS59171953A (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
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JPS61167953A (en) * 1985-01-21 1986-07-29 Fuji Photo Film Co Ltd Silver halide color photosensitive material
JPS6287961A (en) * 1985-10-14 1987-04-22 Konishiroku Photo Ind Co Ltd Silver halide color photographic sensitive material
JPH0673009B2 (en) * 1986-04-16 1994-09-14 コニカ株式会社 Method of forming dye image
JPS62247365A (en) * 1986-04-21 1987-10-28 Konika Corp Silver halide color photogrpahic sensitive material
US5178991A (en) * 1986-09-29 1993-01-12 Fuji Photo Film Co., Ltd. Process for forming a color image employing a color developing solution free from benzyl alcohol
JPS6385547A (en) * 1986-09-29 1988-04-16 Fuji Photo Film Co Ltd Silver halide color photographic sensitive material
JPH06105341B2 (en) * 1987-03-04 1994-12-21 富士写真フイルム株式会社 Silver halide photographic light-sensitive material
JP3431296B2 (en) 1994-08-02 2003-07-28 富士写真フイルム株式会社 Silver halide color photographic materials
US6004738A (en) * 1997-10-30 1999-12-21 Eastman Kodak Company Photographic elements containing cyan dye-forming coupler, coupler solvent and bisphenol derivative
JP4922999B2 (en) * 2008-05-19 2012-04-25 東芝テック株式会社 Printer

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JPS5655945A (en) * 1979-10-15 1981-05-16 Fuji Photo Film Co Ltd Color photographic material
JPS5680045A (en) * 1979-12-05 1981-07-01 Fuji Photo Film Co Ltd Color photographic material
JPS5719739A (en) * 1980-07-11 1982-02-02 Konishiroku Photo Ind Co Ltd Formation of dye image
JPS57136650A (en) * 1981-02-18 1982-08-23 Konishiroku Photo Ind Co Ltd Formation of cyan dye image
JPS57136649A (en) * 1981-02-18 1982-08-23 Konishiroku Photo Ind Co Ltd Formation of cyan dye image
JPS59166956A (en) * 1983-03-14 1984-09-20 Fuji Photo Film Co Ltd Silver halide color photosensitive material

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JPS5680045A (en) * 1979-12-05 1981-07-01 Fuji Photo Film Co Ltd Color photographic material
JPS5719739A (en) * 1980-07-11 1982-02-02 Konishiroku Photo Ind Co Ltd Formation of dye image
JPS57136650A (en) * 1981-02-18 1982-08-23 Konishiroku Photo Ind Co Ltd Formation of cyan dye image
JPS57136649A (en) * 1981-02-18 1982-08-23 Konishiroku Photo Ind Co Ltd Formation of cyan dye image
JPS59166956A (en) * 1983-03-14 1984-09-20 Fuji Photo Film Co Ltd Silver halide color photosensitive material

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JPS59171953A (en) 1984-09-28

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