GB715663A - Improvements relating to photomechanical processes and light-sensitive diazotype materials therefor - Google Patents

Improvements relating to photomechanical processes and light-sensitive diazotype materials therefor

Info

Publication number
GB715663A
GB715663A GB14397/52A GB1439752A GB715663A GB 715663 A GB715663 A GB 715663A GB 14397/52 A GB14397/52 A GB 14397/52A GB 1439752 A GB1439752 A GB 1439752A GB 715663 A GB715663 A GB 715663A
Authority
GB
United Kingdom
Prior art keywords
diazide
acid
benzoquinone
phenyl
naphthoquinone
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
Application number
GB14397/52A
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.)
Kalle GmbH and Co KG
Original Assignee
Kalle GmbH and Co KG
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 Kalle GmbH and Co KG filed Critical Kalle GmbH and Co KG
Publication of GB715663A publication Critical patent/GB715663A/en
Expired legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/022Quinonediazides
    • G03F7/0223Iminoquinonediazides; Para-quinonediazides

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Abstract

Quinone-(1 : 4)-diazides are made by diazotizing the sulphonic and carboxylic acid amides of p-amino-phenols and p-amino-naphthols in a mineral acid medium, when the diazides are formed directly in most cases, or, if diazonium salts are first formed, these are converted by subsequent treatment with alkalis. Particular compounds are: Benzoquinone - (1 : 4) - diazide - (4) - 2 - sulphonanilide (example 1) made by reacting 1-chloro - 4 - nitrobenzene - 2 - sulphochloride with aniline in dioxane, heating the resulting 1-chloro - 4 - nitrobenzene - 2 - sulphonanilide with caustic potash to form 1-hydroxy-4-nitrobenzene - 2 - sulphonanilide, reducing this to the corresponding amino compound and diazotizing the latter. Benzoquinone - (1 : 4) - diazide - (4) - 2 - (N - b -naphthyl) - sulphonamide (example 2) made by procedure as that of example 1 using b -naphthylamine instead of aniline. N : N1 - di - (benzoquinone - (1 : 4) - diazide-(4) - 2 - sulphonyl) - p - phenylene - diamine (example 3) made by procedure as that of example 1 using p-phenylene-diamine instead of aniline. Benzoquinone - (1 : 4) - diazide - (4) - 2 -benzoic-acid anilide (example 4) made by diazotizing the (amino) reduction product of 1-hydroxy - 4 - nitro - 2 - benzoic - acid anilide. Benzoquinone-(1 : 4)-diazide-(4)-2-benzoic acid-N-ethyl-anilide (example 5) made by nitration, reduction and diazotization of salicylic-acid-N-ethyl anilide. Benzoquinone-(1 : 4)-diazide-(4)-2-benzoic acid-21 : 51-dimethyl anilide (example 6) made, similarly to example 6, from salicylic acid-2 : 5-dimethyl anilide. Benzoquinone-(1 : 4)-diazide-(4)-2-benzoic acid-b -naphthylamide (example 7) made by condensing 1 - chloro - 4 - nitrobenzene - 2 - carboxylic acid with b -naphthylamine, heating the product with sodium acetate and acetamide, dissolving with caustic soda, and acidifying to produce 1 - hydroxy - 4 - nitro - benzoic acid naphthylamide which is reduced and diazotized. 6 - Methyl - benzoquinone - (1 : 4) - diazide-(4) - 2 - benzoic - acid - b - naphthylamide (example 8) made by nitration, reduction and diazotization of 3-methyl-2-hydroxy-1-benzoic-acid-b -naphthylamide N : N - di - (benzoquinone - (1 : 4) - diazide- (4) - 2 - benzoyl) - p - phenylene - di-amine (example 9) made, similarly to example 8, from the reaction product of salicyclic acid and p-phenylene diamine. Benzoquinone - (1 : 4) - diazide - (4) - 2 - carboxylic - acid - phenyl - ester (example 10) made, similarly to example 8, from 5-nitro-salicylic-acid-phenyl ester. Benzoquinone - (1 : 4) - diazide - (4) - 2 - carboxylic acid - b - naphthyl ester (example 11) made, similarly from the naphthyl ester corresponding to the phenyl ester used in example 10. Benzoquinone - (1 : 4) - diazide - (4) - 2 - (N-dichlorophenyl) - sulphonamide (example 12) made, as in example 1, from 1-chloro-4-nitrobenzene - 2 - sulphochloride and 2 : 4 - dichloraniline. Benzoquinone - (1 : 4) - diazide - (4) - 2 - (N.a -naphthyl) - sulphonamide (example 13) made analogously to example 2. 2 - Chloro - benzoquinone - (1 : 4) - diazide - (4)-5 - (N - phenyl) - sulphonamide (example 14) made from the corresponding chlorsulphonic acid and aniline. 6 - Bromo - benzoquinone - (1 : 4) - diazide - (4)-2 - (N - phenyl) - sulphonamide (example 15) made by bromination of the sulphonanilide of example 1. Benzoquinone - (1 : 4) - diazide - (4) - 2 - sulphonic-acid-phenyl ester (example 16) made by heating 1 - chloro - 4 - nitrobenzene - 2 - sulphonic acid-phenyl ester with sodium acetate and acetamide, extracting the 1-hydroxy derivative produced with ether and reducing and diazotizing this. Benzoquinone - (1 : 4) - diazide - (4) - 2 - (N - 41-methoxy - phenyl) - sulphonamide (example 17) made as in example 1 using 4-amino-anisole in place of aniline. 2 - Phenyl - benzoquinone - (1 : 4) - diazide and benzoquinone - (1 : 4) - diazide - 2 - phenyl - sulphone (example 18) made as regards the former by diazotization of 2 - phenyl - 1 - hydroxy - 4-amino-benzene; and the latter by Friedel-Craft reaction between 1-chloro-4-nitro-benzene-2-sulphochloride and benzene to form the corresponding - 2 - phenyl - sulphone, which latter is converted to the 1-hydroxy derivative and then reduced and diazotized. Naphthoquinone - (1 : 4) - diazide - (4) - 2-sulphon - b - naphthylamine (example 19) made by heating b -naphthylamine with naphthoquinone - (1 : 4) - diazide - (4) - 2 - sulphochloride which is itself made by reacting 1-hydroxy - naphthalene - 2 - sulphonic acid with nitrous acid, reducing and then diazotizing the nitroso compound formed, and heating the product with chlorsulphonic acid. Naphthoquinone - (1 : 4) - diazide - (4) - 2-sulphon - 2 - amino fluorene compound (example 20) made analogously to example 19, using 2-amino-fluorene in place of b -naphthylamine. Naphthoquinone - (1 : 4) - diazide - (4) - 2-carboxylic acid anilide (example 21) made by diazotizing 4 - amino - 1 - naphthol - 2 - carboxylic acid anilide, which itself can be obtained by reducing the azo dye derived from diazotized aniline and 1-naphthol-2-carboxylic acid anilide. Naphthoquinone - (1 : 4) - diazide - (4) - 2-sulpho - p - tolyl ester (example 22) made by reacting the corresponding sulphochloride with p-cresol. The reaction product of 4 : 41-diamino-diphenylmethane and naphthoquinone - (1 : 4) - diazide - (4) - 2 - sulphochloride (example 23). The reaction product of 71-hydroxy-naphtho-2-ethyl - N - n - propyl - 11 : 21 : 4 : 5 - imidazole and naphthoquinone - (1 : 4) - diazide - (4) - 2 - sulphochloride (example 24). Naphthoquinone - (1 : 4) - diazide - (4) - 2-sulphon-benzylamide (example 26) made analogously to example 19. Naphthoquinone - (1 : 4) - diazide - (4) - 2-sulphon - N - n - butylamide (example 27) made analogously to example 19. Naphthoquinone - (1 : 4) - diazide - (4) - 2-sulphon - 2 - benzimidazolylamide (example 28) made analogously to example 19. Specification 633,796, [Group XVI], is referred to.ALSO:Diazotized aniline is coupled with 1-naphthol-2-carboxylic acid aniline. Specification 633,796, [Group XVI], is referred to.
GB14397/52A 1951-06-07 1952-06-06 Improvements relating to photomechanical processes and light-sensitive diazotype materials therefor Expired GB715663A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE307353X 1951-06-07

Publications (1)

Publication Number Publication Date
GB715663A true GB715663A (en) 1954-09-15

Family

ID=6121382

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14397/52A Expired GB715663A (en) 1951-06-07 1952-06-06 Improvements relating to photomechanical processes and light-sensitive diazotype materials therefor

Country Status (4)

Country Link
CH (1) CH307353A (en)
FR (1) FR1058067A (en)
GB (1) GB715663A (en)
NL (2) NL81221C (en)

Also Published As

Publication number Publication date
NL170133B (en)
NL81221C (en)
CH307353A (en) 1955-05-31
FR1058067A (en) 1954-03-12

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