US3139341A - Two component diazotype layers comprising a di-alkyl [piperazino-methyl]-phenol coupling compound - Google Patents
Two component diazotype layers comprising a di-alkyl [piperazino-methyl]-phenol coupling compound Download PDFInfo
- Publication number
- US3139341A US3139341A US156117A US15611761A US3139341A US 3139341 A US3139341 A US 3139341A US 156117 A US156117 A US 156117A US 15611761 A US15611761 A US 15611761A US 3139341 A US3139341 A US 3139341A
- Authority
- US
- United States
- Prior art keywords
- methyl
- piperazino
- phenol
- dimethyl
- parts
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B06—GENERATING OR TRANSMITTING MECHANICAL VIBRATIONS IN GENERAL
- B06B—METHODS OR APPARATUS FOR GENERATING OR TRANSMITTING MECHANICAL VIBRATIONS OF INFRASONIC, SONIC, OR ULTRASONIC FREQUENCY, e.g. FOR PERFORMING MECHANICAL WORK IN GENERAL
- B06B1/00—Methods or apparatus for generating mechanical vibrations of infrasonic, sonic, or ultrasonic frequency
- B06B1/10—Methods or apparatus for generating mechanical vibrations of infrasonic, sonic, or ultrasonic frequency making use of mechanical energy
- B06B1/16—Methods or apparatus for generating mechanical vibrations of infrasonic, sonic, or ultrasonic frequency making use of mechanical energy operating with systems involving rotary unbalanced masses
- B06B1/167—Orbital vibrators having masses being driven by planetary gearings, rotating cranks or the like
- B06B1/168—Rotary pendulum vibrators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/52—Compositions containing diazo compounds as photosensitive substances
- G03C1/58—Coupling substances therefor
Definitions
- This invention relates to two component diazotype coatings and more particularly to the coupler used therewith so that copies made with the two component diazotype material of the present invention will be satisfactory for intermediate masters in making further copies.
- the present invention relates to two-component diazotype coatings which are characterized in that they contain as coupler one or more compounds corresponding to the general formula R Ra where R and R represent branched and unbranched alkyl groups with up to five carbon atoms in a straight chain, where R is selected from the group consisting of hydrogen, alkyl, beta-hydroxyethyl, aralkyl, aryl, carboxyl, carbethoxy and carbpropoxy; and where R, is selected from the group consisting of hydrogen, branched and unbranched alkyl with up to five carbon atoms in a straight chain and carbethoxy.
- R Ra where R and R represent branched and unbranched alkyl groups with up to five carbon atoms in a straight chain, where R is selected from the group consisting of hydrogen, alkyl, beta-hydroxyethyl, aralkyl, aryl, carboxyl, carbethoxy and carbpropoxy; and where R, is selected from the group consisting of hydrogen,
- the couplers according to the present invention coat very well onto conventional support or supporting material e.g., transparent paper. Also, the coupling products have increased water-resistance and produce high-contrast lines with a high degree of covering power. Even weak and thin lines are clearly reproduced.
- the couplers according to the present invention are superior to the couplers used hitherto for similar purposes.
- the substituted hydroxy dialkyl benzenes used in accordance with the invention as couplers in diazotype reproduction coatings are prepared by the Mannich condensation process by the reaction of dialkyl phenols with equimolecular quantities of formaldehyde and substituted piperazines.
- Suitable hydroxydialkyl benzenes for this reaction are: 2,5-dimethylphenol, 2,3-dimethylphenol, 3,5- dimethylphenol, 2,6-dimethylphen0l, S-methyl-S-ethylphenol, 2-methyl-5-isopropylphenol, 5-methyl-2-isopropylphenol, 3-methyl-6-ethylphenol.
- N-substituted piperice azines for this reaction: N-methyl-piperazine, N-hydroxyethyl-piperazine, N-ethyl-piperazine, N-benzyl-piperazine, N-phenyl-piperazine, piperazine-l-carboxylic acid ethyl ester, and piperazine-l-carboxylic acid propyl ester.
- N-substituted piperazines can also be used: l-phenyl-Z- methyl-piperazine, 1-phenyl-2-ethyl-piperazine, l-phenyl- 3-ethyl-pipcrazine.
- the couplers of the present invention couple with all the usual diazo components.
- the yellow to greenish yellow dyestuffs formed by the coupling of the couplers according to the invention with certain diazo compounds, in particular para-amino-diazo compounds, absorb light rays of so favourable a wave-length range that they have an exceptionally good covering power when used for further copying processes on light-sensitive materials.
- the copies formed are very high in contrast as a result of this increased covering power and are therefore particularly suitable for the preparation of intermediate originals. For example, drawings with weak lines can be reproduced with considerably greater clarity by the employment of the process according to the present invention than if intermediate originals prepared with previously known couplers were used.
- couplers in accordance with the invention are very suitable as adjuvants to other couplers for the production of brown and black tones.
- the crude product contains 74 parts by weight of pure 2,5-dimethyl- 4- [4-phenyl-piperazino-(1')-methyl]-phenol with a melting point of 184-185 C.
- Impure 2,5-dimethyl-6-[4- phenyl-piperazino-(1')-methyl] phenol crystallizes from the ethyl acetate mother liquor as a by-product; this melts at 133-134 C. after recrystallization from ethanol.
- the constitution of the two isomers can be checked by catalytic hydrogenation with copper chromoxide catalyst at about atmospheres and C.
- the condensation product with a melting point of 184-185 C. gives 2,4,5-trimethyl phenol (melting point: 71-72 C.) while the product with a melting point of 133-134 C. gives 2,3,6-trimethyl-phenol (melting point: 63-64" C.).
- Couplers which form dyestuffs of most favorable opacity are 2,5-dimethyl-4-[4'-phenyl-piperazino-(1)-methyl]-phe not and those compounds which in the above list are numbered 1, 3, ll, 14, 15, and 17.
- Example 1 An acetyl cellulose foil was coated with a solution of the following composition: 45 parts by volume of ethylene glycol monomethylether, 45 parts by volume of methyl ethyl ketone, 10 parts by volume of Water, 1.5 parts by weight of citric acid, 1.6 parts by weight of boric acid, a 0.6 part by weight of sulphosalicylic acid, 4.5 parts by weight of 3,5-dimethyl-2-[4'-methylpiperazino-(l')-methyl]-phenol and 4.0 parts by weight of the diazo compound from 1-amino-3-methyl-4-N-ethylaminobenzene in the form of the fluoborate. After the coating was dried, it was exposed behind a master to a 12-amp. arc lamp and developed with ammonia gas in the usual manner. The prints obtained had a yellow shade and were suitable as intermediate originals.
- Example 2 a A solution of 4.5 parts by weight of 2,6-dimethyl-4-[4'- carbethoxy-piperazino-(1)-rnethyl]-phenol, 1 part by volume of concentrated pure hydrochloric acid, 6 parts by weight of citric acid, 3 parts by weight of boric acid, 2 parts by weight-of aluminum sulphate and 4 parts by weight of the diazo compound from 1-amino-4-morpholino benzene in the form of the zinc chloride double salt in 100 parts by volume of Water was coated in the normal manner upon transparent paper and the coating dried. After the material had been exposed behind a master to a 12-amp. carbon arc lamp, it was developed with ammonia gas. The prints, which were yellow in colour, were used as intermediate originals for the preparation of further copies.
- Example 3 The procedure described in Example 1 was followed but the 4.5 parts by weight of 3,5-dimethyl 2-[4' methylpiperazino-(l)-methyl]-phenol were replaced by 4 parts by weight of 2,5-dimethyl-4-[4'-ethyl-piperazino-(1')- methyl]-phenol-hydrochloride. The resulting prints had good properties for further copying purposes.
- Example 4 The coating solution had the same composition as that described in Example 2, but the coupler was replaced by 4.2 parts by weight of 2,5-dimethyl-4-[4'-phenylpiperazino( 1' -methyl] -phenol.
- Example 5 A solution of the following composition was coated upon an opaque paper: 6 parts by weight of citric acid, 3 parts by weight of boric acid, 4.5 parts by weight of thiourea, 15 parts by volume of isopropyl alcohol, 2 parts by weight of 2,5-dimethyl-4-[4-methyl-piperazino-(1)- methy1]-phenol, a 0.6 part by weight of 2-hydroxynaphthalene-3,6-disulphonic acid (sodium salt), and 2 parts by weight of the diazo compound from 1-amino-4- morpholino-benzene in the form of the zinc chloride double salt in parts by volume of water.
- a two-component diazotype coating comprising a light-sensitive diazonium compound and an azo coupling component, said coupling component being 2,5-dimethyl- 4-4'-phenyl-piperazino- 1' -methyl-phenol.
- a two-component diazotype coating composition comprising a light-sensitive diazonium compound and an azo coupling component having the general formula:
- R1 R2 R4 CHE-N N-R3 where R and R are alkyl groups having up to five carbon atoms in a straight chain, R is a member selected from the group consisting of hydrogen, methyl, ethyl, phenyl, benzyl, beta-hydroxyethyl, carbethoxy, and carbpropoxy, and R is selected from the group consisting of hydrogen and methyl.
- a two-component diazotype coating composition comprising light-sensitive diazonium compound and 2,6- dimethyl-4- [4'-phenyl-piperazino-( 1')-methyl] -phenol.
- a two-component diazotype coating composition comprising light-sensitive diazonium compound and 3,5- dimethyl-2- [4-mefihyl-piperazino-(l)-methyl] phenol.
- a two-component diazotype coating composition comprising light-sensitive diazonium compound and 2,5- dimethyl-4- [4'-methyl-piperazino-(l )-methyl] phenol.
- a two-component diazotype coating composition comprising light-sensitive diazonium compound and 2,3- dimethyl-6- [4'-phenyl-piperazino-(1)-methyl] -phenol.
- a two-component diazotype coating composition comprising light-sensitive diazonium compound and 2,5- dimethyl 4- [4 beta hydroxyethyl piperazino (1), methyH-phenol.
- a two-component diazotype coating composition comprising light-sensitive diazonium compound and 2,5- dimethy1-4- [4-ethyl-piperazino-( 1 -methyl] -pheno1.
- a two-component diazotype coating composition comprising light-sensitive diazonium compound and 2,6- dimethyl 4 [4 carbethoxy piperazino-(1')-methyl]- phenol.
- a two-component diazotype coating composition comprising light-sensitive diazonium compound and 2,5- dimethyl 4-[4' carbethoxy piperazino (1')-methyl]- phenol.
- a two-component diazotype coating composition comprising light-sensitive diazonium compound and 2,6-
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Mechanical Engineering (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEK42354A DE1226878B (de) | 1960-12-09 | 1960-12-09 | Lichtempfindliche Diazoschicht |
Publications (1)
Publication Number | Publication Date |
---|---|
US3139341A true US3139341A (en) | 1964-06-30 |
Family
ID=7222720
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US156117A Expired - Lifetime US3139341A (en) | 1960-12-09 | 1961-11-30 | Two component diazotype layers comprising a di-alkyl [piperazino-methyl]-phenol coupling compound |
Country Status (7)
Country | Link |
---|---|
US (1) | US3139341A (sv) |
BE (1) | BE611215A (sv) |
CH (1) | CH409627A (sv) |
DE (1) | DE1226878B (sv) |
FR (1) | FR1312138A (sv) |
GB (1) | GB955886A (sv) |
NL (1) | NL272342A (sv) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3404005A (en) * | 1963-10-01 | 1968-10-01 | Ind Dyestuff Company | Diazo light-sensitive composition and element |
US3791832A (en) * | 1968-05-15 | 1974-02-12 | Ricoh Kk | Diazotype photoprinting material |
US3976491A (en) * | 1974-11-26 | 1976-08-24 | Scott Paper Company | Diazo compositions and diazotype materials prepared from same |
US4108664A (en) * | 1976-11-01 | 1978-08-22 | Gaf Corporation | Light-sensitive negative-working film containing a diazo oxide sensitizer and a p-toluenesulfonyl halide or a 2,4-dihalo-S-triazine |
WO2009078394A1 (ja) * | 2007-12-19 | 2009-06-25 | Dow Corning Toray Co., Ltd. | 4-ヒドロキシフェニルアルキルアミン誘導体 |
CN102633749A (zh) * | 2012-03-22 | 2012-08-15 | 浙江大学 | 1-[4-(2-甲氧乙氧基)苯基]哌嗪盐酸盐的制备方法 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2415786A (en) * | 1944-01-06 | 1947-02-11 | Burroughs Wellcome Co | Unsymmetrically substituted piperazines |
US2467358A (en) * | 1946-06-15 | 1949-04-12 | Gen Aniline & Film Corp | Preparation of diazo prints utilizing resorcinol carbonamides as coupling components |
US2537106A (en) * | 1946-10-18 | 1951-01-09 | Gen Aniline & Film Corp | Poly-acetoacetyl derivatives of polyamines as azo components in diazotype photoprinting material |
US2767186A (en) * | 1956-10-16 | Quaternary ammonium salts of substi- | ||
US2882271A (en) * | 1959-04-14 | Xcixcxh | ||
US2946684A (en) * | 1958-06-14 | 1960-07-26 | Keuffel & Esser Co | Diazotype copying processes |
US3028240A (en) * | 1958-01-18 | 1962-04-03 | Keuffel & Esser Co | Light sensitive diazotype materials |
-
0
- BE BE611215D patent/BE611215A/xx unknown
- NL NL272342D patent/NL272342A/xx unknown
-
1960
- 1960-12-09 DE DEK42354A patent/DE1226878B/de active Pending
-
1961
- 1961-11-20 CH CH1346361A patent/CH409627A/de unknown
- 1961-11-30 US US156117A patent/US3139341A/en not_active Expired - Lifetime
- 1961-12-01 GB GB43009/61A patent/GB955886A/en not_active Expired
- 1961-12-08 FR FR881383A patent/FR1312138A/fr not_active Expired
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2767186A (en) * | 1956-10-16 | Quaternary ammonium salts of substi- | ||
US2882271A (en) * | 1959-04-14 | Xcixcxh | ||
US2415786A (en) * | 1944-01-06 | 1947-02-11 | Burroughs Wellcome Co | Unsymmetrically substituted piperazines |
US2467358A (en) * | 1946-06-15 | 1949-04-12 | Gen Aniline & Film Corp | Preparation of diazo prints utilizing resorcinol carbonamides as coupling components |
US2537106A (en) * | 1946-10-18 | 1951-01-09 | Gen Aniline & Film Corp | Poly-acetoacetyl derivatives of polyamines as azo components in diazotype photoprinting material |
US3028240A (en) * | 1958-01-18 | 1962-04-03 | Keuffel & Esser Co | Light sensitive diazotype materials |
US2946684A (en) * | 1958-06-14 | 1960-07-26 | Keuffel & Esser Co | Diazotype copying processes |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3404005A (en) * | 1963-10-01 | 1968-10-01 | Ind Dyestuff Company | Diazo light-sensitive composition and element |
US3791832A (en) * | 1968-05-15 | 1974-02-12 | Ricoh Kk | Diazotype photoprinting material |
US3976491A (en) * | 1974-11-26 | 1976-08-24 | Scott Paper Company | Diazo compositions and diazotype materials prepared from same |
US4108664A (en) * | 1976-11-01 | 1978-08-22 | Gaf Corporation | Light-sensitive negative-working film containing a diazo oxide sensitizer and a p-toluenesulfonyl halide or a 2,4-dihalo-S-triazine |
WO2009078394A1 (ja) * | 2007-12-19 | 2009-06-25 | Dow Corning Toray Co., Ltd. | 4-ヒドロキシフェニルアルキルアミン誘導体 |
US20100280188A1 (en) * | 2007-12-19 | 2010-11-04 | Takeaki Saiki | 4-hydroxyphenylalkylamine derivative |
CN101903332A (zh) * | 2007-12-19 | 2010-12-01 | 道康宁东丽株式会社 | 4-羟基苯基烷基胺衍生物 |
KR101214833B1 (ko) * | 2007-12-19 | 2012-12-24 | 다우 코닝 도레이 캄파니 리미티드 | 4-하이드록시페닐알킬아민 유도체 |
JP5159793B2 (ja) * | 2007-12-19 | 2013-03-13 | 東レ・ダウコーニング株式会社 | 4−ヒドロキシフェニルアルキルアミン誘導体 |
US8624064B2 (en) | 2007-12-19 | 2014-01-07 | Dow Corning Toray Company, Ltd. | 4-hydroxyphenylalkylamine derivative |
CN101903332B (zh) * | 2007-12-19 | 2015-01-14 | 道康宁东丽株式会社 | 4-羟基苯基烷基胺衍生物 |
CN102633749A (zh) * | 2012-03-22 | 2012-08-15 | 浙江大学 | 1-[4-(2-甲氧乙氧基)苯基]哌嗪盐酸盐的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
DE1226878B (de) | 1966-10-13 |
CH409627A (de) | 1966-03-15 |
BE611215A (sv) | |
GB955886A (en) | 1964-04-22 |
NL272342A (sv) | |
FR1312138A (fr) | 1962-12-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US3248220A (en) | Two-component diazotype material | |
US3028240A (en) | Light sensitive diazotype materials | |
US3139341A (en) | Two component diazotype layers comprising a di-alkyl [piperazino-methyl]-phenol coupling compound | |
US2946684A (en) | Diazotype copying processes | |
US3272630A (en) | Light-sensitive reproduction material containing unilaterally diazotized p-phenylene-diamine derivatives as the light sensitive substance | |
US3281245A (en) | Diazotype material | |
US4492749A (en) | Diazotype materials with 2-hydroxy-naphthalene having sulfonamide substituent as coupler | |
US3338713A (en) | Diazotype material | |
US3615575A (en) | Two-component black-line diazo-type material | |
US3615578A (en) | Light-sensitive diazo compounds and light-sensitive material containing them | |
US3294542A (en) | Photosensitive diazo compositions | |
US2532126A (en) | Diazotype photographic material | |
US2350843A (en) | Diazotype photographic material | |
US3255010A (en) | Two-component diazotype material | |
US2672418A (en) | Light-sensitive diazotype material | |
US3186845A (en) | Two-component diazotype material | |
US3499763A (en) | Bis phenols as high opacity diazotype couplers | |
US2212959A (en) | Photoprinting process | |
US3183093A (en) | Light sensitive diazotype material containing dibenzyl alkylamine coupling agents | |
US2063832A (en) | Light sensitive diazo layers | |
US3639421A (en) | Diazotype materials | |
US3281246A (en) | Diazotype reproduction material | |
US3758307A (en) | O)-3-substituted benzene diazonium salt diazotype light sensitive compositions containing a 4 - (n-pyrrolidin | |
US3868255A (en) | Diazonium salts and diazotype materials | |
US4590263A (en) | High speed diazonium salts useful in diazo type photoreproduction |