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
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- 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
- 150000001875 compounds Chemical class 0.000 title description 9
- 230000008878 coupling Effects 0.000 title description 5
- 238000010168 coupling process Methods 0.000 title description 5
- 238000005859 coupling reaction Methods 0.000 title description 5
- 150000001989 diazonium salts Chemical class 0.000 claims description 12
- 239000008199 coating composition Substances 0.000 claims description 11
- 238000006149 azo coupling reaction Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- -1 beta-hydroxyethyl Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- VXSCPERJHPWROZ-UHFFFAOYSA-N 2,4,5-trimethylphenol Chemical compound CC1=CC(C)=C(O)C=C1C VXSCPERJHPWROZ-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- PHNDZBFLOPIMSM-UHFFFAOYSA-N 4-morpholin-4-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCOCC1 PHNDZBFLOPIMSM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- FDLFJMALQUAPDM-UHFFFAOYSA-N 2-ethyl-1-phenylpiperazine Chemical compound CCC1CNCCN1C1=CC=CC=C1 FDLFJMALQUAPDM-UHFFFAOYSA-N 0.000 description 1
- LTRVUFFOMIUCPJ-UHFFFAOYSA-N 2-ethyl-5-methylphenol Chemical compound CCC1=CC=C(C)C=C1O LTRVUFFOMIUCPJ-UHFFFAOYSA-N 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- RECUKUPTGUEGMW-UHFFFAOYSA-N carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 description 1
- HHTWOMMSBMNRKP-UHFFFAOYSA-N carvacrol Natural products CC(=C)C1=CC=C(C)C(O)=C1 HHTWOMMSBMNRKP-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- OSDANZNEPXWSQQ-UHFFFAOYSA-N copper chromium(3+) oxygen(2-) Chemical compound [O--].[Cr+3].[Cu++] OSDANZNEPXWSQQ-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- IGXBNWXKQPCCCJ-UHFFFAOYSA-N propyl piperazine-1-carboxylate Chemical compound CCCOC(=O)N1CCNCC1 IGXBNWXKQPCCCJ-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
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-
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- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (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 (en(2012)) |
| BE (1) | BE611215A (en(2012)) |
| CH (1) | CH409627A (en(2012)) |
| DE (1) | DE1226878B (en(2012)) |
| FR (1) | FR1312138A (en(2012)) |
| GB (1) | GB955886A (en(2012)) |
| NL (1) | NL272342A (en(2012)) |
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
- NL NL272342D patent/NL272342A/xx unknown
- BE BE611215D patent/BE611215A/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 |
|---|---|
| CH409627A (de) | 1966-03-15 |
| GB955886A (en) | 1964-04-22 |
| DE1226878B (de) | 1966-10-13 |
| BE611215A (en(2012)) | |
| NL272342A (en(2012)) | |
| FR1312138A (fr) | 1962-12-14 |
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