GB1330932A - Phenolic resin condensation product and light-sensitive compositions containing it - Google Patents
Phenolic resin condensation product and light-sensitive compositions containing itInfo
- Publication number
- GB1330932A GB1330932A GB4324871A GB4324871A GB1330932A GB 1330932 A GB1330932 A GB 1330932A GB 4324871 A GB4324871 A GB 4324871A GB 4324871 A GB4324871 A GB 4324871A GB 1330932 A GB1330932 A GB 1330932A
- Authority
- GB
- United Kingdom
- Prior art keywords
- resin
- hcho
- light
- tetrahydroxy
- prepared
- 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
Links
- 239000007859 condensation product Substances 0.000 title abstract 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title abstract 2
- 229920001568 phenolic resin Polymers 0.000 title abstract 2
- 239000005011 phenolic resin Substances 0.000 title abstract 2
- 229920005989 resin Polymers 0.000 abstract 10
- 239000011347 resin Substances 0.000 abstract 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 carboalkoxy Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 abstract 1
- 229940105324 1,2-naphthoquinone Drugs 0.000 abstract 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- 229930185605 Bisphenol Natural products 0.000 abstract 1
- MPGOFFXRGUQRMW-UHFFFAOYSA-N [N-]=[N+]=[N-].[N-]=[N+]=[N-].O=C1C=CC=CC1=O Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].O=C1C=CC=CC1=O MPGOFFXRGUQRMW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 229920003986 novolac Polymers 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
1330932 Phenolic resin KONISHIROKU PHOTO INDUSTRY CO Ltd 16 Sept 1971 [16 Sept 1970] 43248/71 Heading C3R [Also in Division G2] A condensation product is obtained by reacting (i) a sulphonyl chloride of o-benzoquinonediazide or o-naphthoquinonediazide with (ii) a bisphenol-formaldehyde resin selected from the formulae wherein x represents -CH 2 -, -O-, -S-, -SO-, or -SO 2 -, or a methylene group in which one or both hydrogen atoms are substituted by an alkyl or aryl group or a carboxyalkyl group whose carboxyl portion may be esterified or amidated, or a cyclic alkylene group; each of R 1 and R 2 which may be the same or different, represents a hydrogen atom or a C 1-4 alkyl, alkoxy, carboalkoxy, carboxy or hydroxy group, and n is at least 2. The resin can be prepared by condensing HCHO and the bisphenol preferably in a molar ratio of 0À85 to 1À0 mole, using an acid catalyst, e.g. HCl or oxalic acid or an alkaline catalyst, e.g. NaOH or NH 4 OH. In the examples resins are prepared in ethanol solution from HCHO and (1) 4,4<SP>1</SP>-isopropylidenediphenol and (2) 2,2<SP>1</SP>,4,4<SP>1</SP>-tetrahydroxy-6-6<SP>1</SP>- dimethyldiphenylethane; and condensation products are obtained by reacting 1,2-naphthoquinone - 2 - diazide - 4 - (or 5) - sulphonyl chloride with (i) resin (1), (ii) resin 2, (iii) 2,2<SP>1</SP>- 4,41 - tetrahydroxy - diphenylpropane (1,1)- HCHO resin, (iv) 2,2<SP>1</SP>,4,4<SP>1</SP>- tetrahydroxy-6,6<SP>1</SP>- dimethyldiphenylethane HCHO resin, (v) 4,4-<SP>1</SP> bis - (p - hydroxyphenyl) butyric acid-HCHO resin, (vi) 2,2<SP>1</SP>,4,4<SP>1</SP>-tetrahydroxydiphenyl-sulphide-HCHO resin, using dioxane as solvent in the presence of Na 2 CO 3 at a pH below 8. Light-sensitive compositions can be prepared by dissolving the product and optionally an alkaline soluble novolak resin in an organic solvent such as acetone, dioxane or methoxy- or ethoxy-ethanol. A dye such as Methyl Violet may also be added. Uses.-Light-sensitive materials for printing plates.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8050970A JPS505084B1 (en) | 1970-09-16 | 1970-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1330932A true GB1330932A (en) | 1973-09-19 |
Family
ID=13720268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4324871A Expired GB1330932A (en) | 1970-09-16 | 1971-09-16 | Phenolic resin condensation product and light-sensitive compositions containing it |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS505084B1 (en) |
| DE (1) | DE2146166A1 (en) |
| GB (1) | GB1330932A (en) |
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1981000772A1 (en) * | 1979-09-05 | 1981-03-19 | Minnesota Mining & Mfg | Single sheet color proofing diazo oxide system |
| US4306011A (en) * | 1979-06-16 | 1981-12-15 | Konishiroku Photo Industry Co., Ltd. | Photosensitive composite and photosensitive lithographic printing plate |
| US4306010A (en) * | 1979-06-16 | 1981-12-15 | Konishiroku Photo Industry Co., Ltd. | Photosensitive o-quinone diazide composition and photosensitive lithographic printing plate |
| US4424270A (en) | 1981-01-03 | 1984-01-03 | Hoechst Aktiengesellschaft | Light-sensitive mixture comprising a naphthoquinonediazidesulfonic acid ester and process for preparing said ester |
| US4439511A (en) * | 1981-07-14 | 1984-03-27 | Hoechst Aktiengesellschaft | Light-sensitive mixture based on O-naphthoquinone diazide ester of condensate of bisphenol and formaldehyde and light-sensitive copying material prepared therefrom |
| US4632900A (en) * | 1984-03-07 | 1986-12-30 | Ciba-Geigy Corporation | Process for the production of images after electrodeposition of positive photoresist on electrically conductive surface |
| US4632891A (en) * | 1984-10-04 | 1986-12-30 | Ciba-Geigy Corporation | Process for the production of images |
| US4681923A (en) * | 1985-03-02 | 1987-07-21 | Ciba-Geigy Corporation | Modified quinone-diazide group-containing phenolic novolak resins |
| US4839253A (en) * | 1984-12-01 | 1989-06-13 | Ciba-Geigy Corporation | Photosensitive and electrodepositable phenolic resin with quinone diazide sulfonyloxy group |
| US4873169A (en) * | 1986-08-27 | 1989-10-10 | Hoechst Aktiengesellschaft | Process for the preparation of an o-naphthoquinonediazide sulfonic acid ester and photosensitive mixture containing same |
| EP0565006A2 (en) | 1992-04-06 | 1993-10-13 | Fuji Photo Film Co., Ltd. | Method for preparing PS plate |
| EP0713143A2 (en) | 1994-11-18 | 1996-05-22 | Fuji Photo Film Co., Ltd. | Photosensitive planographic printing plate |
| EP0780730A2 (en) | 1995-12-22 | 1997-06-25 | Fuji Photo Film Co., Ltd. | Positive-type light-sensitive lithographic printing plate |
| WO2004035687A1 (en) * | 2002-10-15 | 2004-04-29 | Agfa-Gevaert | Polymer for heat-sensitive lithographic printing plate precursor |
| EP1640173A1 (en) | 2004-09-27 | 2006-03-29 | Fuji Photo Film Co., Ltd. | Planographic printing plate precursor |
| EP1690685A2 (en) | 2005-02-09 | 2006-08-16 | Fuji Photo Film Co., Ltd. | Planographic printing plate precursor |
| EP1705004A1 (en) | 2005-03-22 | 2006-09-27 | Fuji Photo Film Co., Ltd. | Planographic printing plate precursor |
| EP1925447A1 (en) | 2002-09-17 | 2008-05-28 | FUJIFILM Corporation | Image forming material |
| EP2036721A1 (en) | 2000-11-30 | 2009-03-18 | FUJIFILM Corporation | Planographic printing plate precursor |
| EP2042340A2 (en) | 2007-09-27 | 2009-04-01 | Fujifilm Corporation | Lithographic printing plate surface protective agent and platemaking method for lithographic printing plate |
| EP2042305A2 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Planographic printing plate precursor |
| EP2042308A2 (en) | 2007-09-27 | 2009-04-01 | FUJIFILM Corporation | Planographic printing plate precursor |
| EP2042306A2 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Planographic printing plate precursor and method of producing a copolymer used therein |
| EP2042310A2 (en) | 2007-09-27 | 2009-04-01 | FUJIFILM Corporation | Planographic printing plate precursor |
| WO2009063824A1 (en) | 2007-11-14 | 2009-05-22 | Fujifilm Corporation | Method of drying coating film and process for producing lithographic printing plate precursor |
| EP2105690A2 (en) | 2008-03-26 | 2009-09-30 | Fujifilm Corporation | Method and apparatus for drying |
| EP2106907A2 (en) | 2008-04-02 | 2009-10-07 | FUJIFILM Corporation | Planographic printing plate precursor |
| EP2161129A2 (en) | 2008-09-09 | 2010-03-10 | Fujifilm Corporation | Photosensitive lithographic printing plate precursor for infrared laser |
| EP2236293A2 (en) | 2009-03-31 | 2010-10-06 | FUJIFILM Corporation | Lithographic printing plate precursor |
| WO2011037005A1 (en) | 2009-09-24 | 2011-03-31 | 富士フイルム株式会社 | Lithographic printing original plate |
| EP2381312A2 (en) | 2000-08-25 | 2011-10-26 | Fujifilm Corporation | Alkaline liquid developer for lithographic printing plate and method for preparing lithographic printing plate |
| EP2641738A2 (en) | 2012-03-23 | 2013-09-25 | Fujifilm Corporation | Method of producing planographic printing plate and planographic printing plate |
| EP2644379A1 (en) | 2012-03-30 | 2013-10-02 | FUJIFILM Corporation | Method of producing a planographic printing plate |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2015721A1 (en) * | 1989-05-12 | 1990-11-12 | Karen Ann Graziano | Method of using highly branched novolaks in photoresists |
| DE3935876A1 (en) * | 1989-10-27 | 1991-05-02 | Basf Ag | RADIATION-SENSITIVE MIXTURE |
| WO2008114766A1 (en) * | 2007-03-12 | 2008-09-25 | Tohto Kasei Co., Ltd. | Novel polyvalent hydroxy compound, method for producing the compound, epoxy resin and epoxy resin composition each using the compound, and cured product of the composition |
| TW201815738A (en) * | 2016-07-21 | 2018-05-01 | 日商三菱瓦斯化學股份有限公司 | Method for forming compound, resin, composition and resist pattern, and circuit pattern forming method |
-
1970
- 1970-09-16 JP JP8050970A patent/JPS505084B1/ja active Pending
-
1971
- 1971-09-15 DE DE19712146166 patent/DE2146166A1/en active Pending
- 1971-09-16 GB GB4324871A patent/GB1330932A/en not_active Expired
Cited By (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4306011A (en) * | 1979-06-16 | 1981-12-15 | Konishiroku Photo Industry Co., Ltd. | Photosensitive composite and photosensitive lithographic printing plate |
| US4306010A (en) * | 1979-06-16 | 1981-12-15 | Konishiroku Photo Industry Co., Ltd. | Photosensitive o-quinone diazide composition and photosensitive lithographic printing plate |
| WO1981000772A1 (en) * | 1979-09-05 | 1981-03-19 | Minnesota Mining & Mfg | Single sheet color proofing diazo oxide system |
| US4260673A (en) * | 1979-09-05 | 1981-04-07 | Minnesota Mining And Manufacturing Company | Single sheet color proofing system |
| US4424270A (en) | 1981-01-03 | 1984-01-03 | Hoechst Aktiengesellschaft | Light-sensitive mixture comprising a naphthoquinonediazidesulfonic acid ester and process for preparing said ester |
| US4555469A (en) * | 1981-01-03 | 1985-11-26 | Hoechst Aktiengesellschaft | Process of preparing light-sensitive naphthoquinonediazidesulfonic acid ester |
| US4439511A (en) * | 1981-07-14 | 1984-03-27 | Hoechst Aktiengesellschaft | Light-sensitive mixture based on O-naphthoquinone diazide ester of condensate of bisphenol and formaldehyde and light-sensitive copying material prepared therefrom |
| US4632900A (en) * | 1984-03-07 | 1986-12-30 | Ciba-Geigy Corporation | Process for the production of images after electrodeposition of positive photoresist on electrically conductive surface |
| US4632891A (en) * | 1984-10-04 | 1986-12-30 | Ciba-Geigy Corporation | Process for the production of images |
| US4839253A (en) * | 1984-12-01 | 1989-06-13 | Ciba-Geigy Corporation | Photosensitive and electrodepositable phenolic resin with quinone diazide sulfonyloxy group |
| US4681923A (en) * | 1985-03-02 | 1987-07-21 | Ciba-Geigy Corporation | Modified quinone-diazide group-containing phenolic novolak resins |
| US4873169A (en) * | 1986-08-27 | 1989-10-10 | Hoechst Aktiengesellschaft | Process for the preparation of an o-naphthoquinonediazide sulfonic acid ester and photosensitive mixture containing same |
| EP0565006A2 (en) | 1992-04-06 | 1993-10-13 | Fuji Photo Film Co., Ltd. | Method for preparing PS plate |
| EP0713143A2 (en) | 1994-11-18 | 1996-05-22 | Fuji Photo Film Co., Ltd. | Photosensitive planographic printing plate |
| EP0780730A2 (en) | 1995-12-22 | 1997-06-25 | Fuji Photo Film Co., Ltd. | Positive-type light-sensitive lithographic printing plate |
| EP2381312A2 (en) | 2000-08-25 | 2011-10-26 | Fujifilm Corporation | Alkaline liquid developer for lithographic printing plate and method for preparing lithographic printing plate |
| EP2036721A1 (en) | 2000-11-30 | 2009-03-18 | FUJIFILM Corporation | Planographic printing plate precursor |
| EP1925447A1 (en) | 2002-09-17 | 2008-05-28 | FUJIFILM Corporation | Image forming material |
| WO2004035687A1 (en) * | 2002-10-15 | 2004-04-29 | Agfa-Gevaert | Polymer for heat-sensitive lithographic printing plate precursor |
| EP1640173A1 (en) | 2004-09-27 | 2006-03-29 | Fuji Photo Film Co., Ltd. | Planographic printing plate precursor |
| EP1690685A2 (en) | 2005-02-09 | 2006-08-16 | Fuji Photo Film Co., Ltd. | Planographic printing plate precursor |
| EP1705004A1 (en) | 2005-03-22 | 2006-09-27 | Fuji Photo Film Co., Ltd. | Planographic printing plate precursor |
| EP2042340A2 (en) | 2007-09-27 | 2009-04-01 | Fujifilm Corporation | Lithographic printing plate surface protective agent and platemaking method for lithographic printing plate |
| EP2042308A2 (en) | 2007-09-27 | 2009-04-01 | FUJIFILM Corporation | Planographic printing plate precursor |
| EP2042310A2 (en) | 2007-09-27 | 2009-04-01 | FUJIFILM Corporation | Planographic printing plate precursor |
| EP2042305A2 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Planographic printing plate precursor |
| EP2042306A2 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Planographic printing plate precursor and method of producing a copolymer used therein |
| WO2009063824A1 (en) | 2007-11-14 | 2009-05-22 | Fujifilm Corporation | Method of drying coating film and process for producing lithographic printing plate precursor |
| EP2105690A2 (en) | 2008-03-26 | 2009-09-30 | Fujifilm Corporation | Method and apparatus for drying |
| EP2106907A2 (en) | 2008-04-02 | 2009-10-07 | FUJIFILM Corporation | Planographic printing plate precursor |
| EP2161129A2 (en) | 2008-09-09 | 2010-03-10 | Fujifilm Corporation | Photosensitive lithographic printing plate precursor for infrared laser |
| EP2236293A2 (en) | 2009-03-31 | 2010-10-06 | FUJIFILM Corporation | Lithographic printing plate precursor |
| WO2011037005A1 (en) | 2009-09-24 | 2011-03-31 | 富士フイルム株式会社 | Lithographic printing original plate |
| EP2641738A2 (en) | 2012-03-23 | 2013-09-25 | Fujifilm Corporation | Method of producing planographic printing plate and planographic printing plate |
| EP2644379A1 (en) | 2012-03-30 | 2013-10-02 | FUJIFILM Corporation | Method of producing a planographic printing plate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS505084B1 (en) | 1975-02-28 |
| DE2146166A1 (en) | 1972-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |