JPS5945700B2 - 4,4↑Water-soluble azo dye derived from 1-diaminobenzanilide - Google Patents
4,4↑Water-soluble azo dye derived from 1-diaminobenzanilideInfo
- Publication number
- JPS5945700B2 JPS5945700B2 JP6931183A JP6931183A JPS5945700B2 JP S5945700 B2 JPS5945700 B2 JP S5945700B2 JP 6931183 A JP6931183 A JP 6931183A JP 6931183 A JP6931183 A JP 6931183A JP S5945700 B2 JPS5945700 B2 JP S5945700B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- water
- diaminobenzanilide
- azo dye
- soluble azo
- 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
- 239000000987 azo dye Substances 0.000 title claims description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 2
- 239000000975 dye Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000835 fiber Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 239000000982 direct dye Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 2
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000009120 camo Nutrition 0.000 description 2
- 235000005607 chanvre indien Nutrition 0.000 description 2
- 239000011487 hemp Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/64—Higher polyazo dyes, e.g. of the types
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
- C09B35/467—D being derived from diaminodiaryl linked through CON<, SO2N<, CSN<
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/24—Disazo or polyazo compounds
- C09B45/28—Disazo or polyazo compounds containing copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Polymerization Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は、亜麻、再生セルロース繊維、麻、大麻、黄麻
のような綿及び再生セルロース繊維や、さらには天然及
び合成ポリアミド系繊維並びにこれらの繊維の配合物、
皮革及びその他の類似材料を直接染色するのに適した一
連の新規なスルホン化アゾ染料に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to cotton and regenerated cellulose fibers such as flax, regenerated cellulose fibers, hemp, hemp, jute, as well as natural and synthetic polyamide fibers and blends of these fibers,
A series of new sulfonated azo dyes suitable for direct dyeing of leather and other similar materials.
本発明の目的は、次の一般式（Ｉ）
を有する水溶性アゾ染料の製造法を提供することである
。An object of the present invention is to provide a method for producing a water-soluble azo dye having the following general formula (I).
上記の直接染料は、ベンジジン系の従来の直接染料の適
用特性と類似の特性を示すが、しかしそれらの製造の過
程で何らの特別の毒物学上の危険を伴なわない。The above-mentioned direct dyes exhibit application properties similar to those of conventional direct dyes of the benzidine series, but do not involve any special toxicological risks in the process of their preparation.
事実、本発明の染料の構造と類似の構造を有する染料を
製造するために利用されるベンジジン及びその誘導体は
、その発がん性作用のために危険な化合物であつて、そ
の結果、これらの使用及び製造は厳格な衛生上及び安全
上の基準値を要求する。In fact, benzidine and its derivatives utilized to produce dyes with a structure similar to that of the dyes of the present invention are dangerous compounds due to their carcinogenic effects and, as a result, their use and Manufacturing requires strict hygiene and safety standards.
一般式（１）を有する直接染料は、業界で既知の方法に
類似の方法により製造し得る。Direct dyes having general formula (1) can be produced by methods analogous to those known in the industry.
これらの染料は、セルロース系繊維及び含窒素系繊維並
びに皮革を緑から褐色までの暗色系の色に染色させる。These dyes dye cellulosic fibers, nitrogen-containing fibers, and leather in dark colors ranging from green to brown.
一般式（１）の染料の染色作業は、直接ベンジジン系染
料に使用される場合と同じ方法に従つて、即ち、適量の
染料及び５〜２０（Ｌ（繊維の重量に関して）の無水Ｎ
ａ，ｓＯ４又はＮａＣｌを含有する水浴中で一般に５０
〜１００℃の間の温度で行なわれる。The dyeing operation of the dyes of general formula (1) follows the same method as used for direct benzidine dyes, i.e. an appropriate amount of dye and 5 to 20 L (relative to the weight of the fiber) of anhydrous N
Generally 50 in a water bath containing a, sO4 or NaCl.
It is carried out at temperatures between -100°C.
下記の例は、本発明を例示するために示すものであつて
、それを制限するものではない。The following examples are given to illustrate the invention without limiting it.
「部」は、特に示してなければ、重量として表わされて
いるものと理解されたい。It is to be understood that "parts" are expressed as weight, unless otherwise indicated.
例１
１７０部の水とＴ６．７部の２００Ｂｅ゛（３２．１４
重量（ｆｌ））ＨＣｌ中に懸濁させた１９．６部のスル
フアニル酸及び１００部の氷を、これに７．８部のＮａ
ＮＯ３（２０％溶液（部／容量）として）２０〜３０分
間で注入することによつてＯ℃でジアゾ化した。Example 1 170 parts of water and 6.7 parts of T200Be(32.14
weight (fl)) 19.6 parts of sulfanilic acid suspended in HCl and 100 parts of ice were added to 7.8 parts of Na
Diazotization was carried out at O<0>C by injection of NO3 (as a 20% solution (parts/volume)) for 20-30 minutes.
２時間攪拌し、過剰の亜硝酸をスルフアミン酸により除
去した。After stirring for 2 hours, excess nitrous acid was removed with sulfamic acid.
このジアゾ化体を、１２．２部のｍ−トリレンジアミン
を２００部の水、１００部の氷及び２２部の２０ンＢｅ
”（３２．１４重量％）ＨＣｌに溶解してなる溶液上に
１５分間で注入した。そのＰＨ値は、２０．７９のＮａ
ＨＣＯ３を２００部の水に溶解してなる溶液を１時間で
滴下することによつて５．５〜６とした。This diazotized product was mixed with 12.2 parts of m-tolylene diamine, 200 parts of water, 100 parts of ice, and 22 parts of 20% Be.
(32.14% by weight) dissolved in HCl for 15 minutes.The pH value was 20.79.
A solution of HCO3 dissolved in 200 parts of water was added dropwise over 1 hour to obtain a concentration of 5.5 to 6.
これを一夜攪拌した。翌朝、それを４０〜４５℃に加熱
し、１４０部の１０％Ｎａ２ｃＯ３水溶液（部／重量）
を混合するとＰＨ値は９〜９．５であつた。溶解が完了
したならば、これを氷で１０℃に冷却し、次いで、下記
のように４，４′−ジアミノベンズアニリドをサリチル
酸でカツプリングすることによつて別個に製造したジア
ゾ−モノアゾ体を混合した。温度は１０℃であり、ＰＨ
値は約８であつた。一夜攪拌した。翌朝、これを約７０
℃に加熱し、２８部の２０。Ｂｅ”（３２．１４重量％
）ＨＣｌで酸性化し、３００部の岩塩により１０％（部
／容量）で塩析させた。全体を真空済過し、１０％塩水
で洗浄した。次いでそれを十分に圧搾した。このように
して得られ、そして７０〜８０℃で２４時間乾燥した生
成物は、セルロース系繊維を黄褐色の色に染色した。得
られた染料の可視光での吸収極大波長は４３８ｍμ（Ｐ
Ｈ９の水溶液で測定）であつた。前記のジアゾ−モノア
ゾ体は下記のように製造した。１００部の水と５２部の
２０下Ｂｅ２（３２．１４重量％）塩酸中に懸濁させた
２２．７部の４，４′−ジアミノベンズアニリドを１０
０部の氷で冷却した後、これにＯ〜５℃において、１４
部のＮａＮＯ２を６０部の水に溶解してなる溶液を滴下
することによつてテトラゾ化した。This was stirred overnight. The next morning, heat it to 40-45 °C and add 140 parts of 10% Na2cO3 aqueous solution (parts/weight).
When mixed, the pH value was 9 to 9.5. Once dissolution is complete, it is cooled to 10° C. with ice and then mixed with the diazo-monoazo compound prepared separately by coupling 4,4′-diaminobenzanilide with salicylic acid as described below. did. The temperature was 10℃, and the pH
The value was approximately 8. Stir overnight. The next morning, I added this to about 70
Heat to 20°C and 28 parts. Be” (32.14% by weight
) Acidified with HCl and salted out at 10% (parts/volume) with 300 parts of rock salt. The whole was vacuumed and washed with 10% brine. It was then thoroughly pressed. The product thus obtained and dried for 24 hours at 70-80° C. dyed the cellulosic fibers in a tan color. The absorption maximum wavelength of the obtained dye in visible light is 438 mμ (P
(measured with an aqueous solution of H9). The above diazo-monoazo compound was produced as follows. 22.7 parts of 4,4'-diaminobenzanilide suspended in 100 parts of water and 52 parts of 20 Be2 (32.14% by weight) hydrochloric acid were mixed with 10
After cooling with 0 parts of ice, it was added at 0 to 5°C for 14
Tetrazotization was carried out by dropping a solution prepared by dissolving 1 part of NaNO2 in 60 parts of water.
６０分間攪拌した後、過剰の亜硝酸をスルフアミン酸に
より除去した。After stirring for 60 minutes, excess nitrous acid was removed with sulfamic acid.
１５部のサリチル酸を１５０部の水と１４．６部の３６
のＢｅ゛（３０．３０重量％）ＮａＯＨ中に容解した。15 parts of salicylic acid, 150 parts of water and 14.6 parts of 36
Be (30.30% by weight) was dissolved in NaOH.
５部のＮａ２ＣＯ３（２０％溶液（部／容量）として）
を加え且つ５０部の氷でＯ〜２℃に冷却して得られた溶
液を上記のテトラゾ体と素早く混合した（約２１分間）
。5 parts Na2CO3 (as a 20% solution (parts/volume))
and cooled to 0~2°C with 50 parts of ice, the resulting solution was quickly mixed with the above tetrazo form (approximately 21 minutes).
.
１５部のＮａ２ｃＯ，を２０％溶演（部／容量）として
１時間で加えた。15 parts of Na2cO, as a 20% solution (parts/volume), were added in 1 hour.
Claims (1)
ラゾ化した４，４′−ジアミノベンズアニリドをアルカ
リ性媒質中でサリチル酸とカップリングさせ、得られた
ジアゾ−モノアゾ体を実質上アルカリ性媒質中で前記Ａ
の意味を有するカップリング要素とカップリングさせる
ことを特徴とするスルホン化アゾ染料の製造法。[Claims] 1. In producing a sulfonated azo dye having the following general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ "Where A = ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼"4,4'-diaminobenzanilide is coupled with salicylic acid in an alkaline medium, and the resulting diazo-monoazo compound is combined with the above A in a substantially alkaline medium.
1. A method for producing a sulfonated azo dye, which comprises coupling with a coupling element having the following meaning.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20381A/74 | 1974-02-11 | ||
| IT2038174A IT1007324B (en) | 1974-02-11 | 1974-02-11 | WATER-SOLUBLE AZO DYES DERIVED FROM 4.4 DIAMINOBENZANILIDE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58194955A JPS58194955A (en) | 1983-11-14 |
| JPS5945700B2 true JPS5945700B2 (en) | 1984-11-08 |
Family
ID=11166217
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1639375A Expired JPS5839181B2 (en) | 1974-02-11 | 1975-02-10 | 4,4'- diaminobenzanilide |
| JP6931283A Expired JPS5945701B2 (en) | 1974-02-11 | 1983-04-21 | 4,4↑Water-soluble azo dye derived from 1-diaminobenzanilide |
| JP6931183A Expired JPS5945700B2 (en) | 1974-02-11 | 1983-04-21 | 4,4↑Water-soluble azo dye derived from 1-diaminobenzanilide |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1639375A Expired JPS5839181B2 (en) | 1974-02-11 | 1975-02-10 | 4,4'- diaminobenzanilide |
| JP6931283A Expired JPS5945701B2 (en) | 1974-02-11 | 1983-04-21 | 4,4↑Water-soluble azo dye derived from 1-diaminobenzanilide |
Country Status (10)
| Country | Link |
|---|---|
| JP (3) | JPS5839181B2 (en) |
| BE (1) | BE825409A (en) |
| CA (1) | CA1037029A (en) |
| CH (1) | CH624424A5 (en) |
| DE (1) | DE2505188C2 (en) |
| ES (1) | ES434567A1 (en) |
| FR (1) | FR2260607B1 (en) |
| GB (1) | GB1486542A (en) |
| IT (1) | IT1007324B (en) |
| NL (1) | NL7501419A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05217083A (en) * | 1992-02-03 | 1993-08-27 | Adobitsuku:Kk | Alarm device with infrared-ray detector |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61203497U (en) * | 1985-06-10 | 1986-12-20 | ||
| JP5022744B2 (en) | 2007-03-13 | 2012-09-12 | 本田技研工業株式会社 | Vehicle assembly equipment |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH212995A (en) * | 1938-10-05 | 1940-12-31 | Geigy Ag J R | Process for the preparation of a hexakisazo dye. |
| US2204230A (en) * | 1939-03-29 | 1940-06-11 | Du Pont | Azo dyes |
| DE849287C (en) * | 1949-07-20 | 1952-09-15 | Ciba Geigy | Process for the preparation of trisazo dyes |
| CH313297A (en) * | 1953-01-30 | 1956-03-31 | Geigy Ag J R | Process for the production of a brown leather dye |
| BE795378A (en) * | 1972-02-15 | 1973-08-13 | Sandoz Sa | NEW POLYAZOIC DYES AND THEIR PREPARATION |
-
1974
- 1974-02-11 IT IT2038174A patent/IT1007324B/en active
-
1975
- 1975-02-06 NL NL7501419A patent/NL7501419A/en not_active Application Discontinuation
- 1975-02-07 DE DE19752505188 patent/DE2505188C2/en not_active Expired
- 1975-02-07 GB GB535575A patent/GB1486542A/en not_active Expired
- 1975-02-08 ES ES434567A patent/ES434567A1/en not_active Expired
- 1975-02-10 CA CA219,678A patent/CA1037029A/en not_active Expired
- 1975-02-10 FR FR7504026A patent/FR2260607B1/fr not_active Expired
- 1975-02-10 JP JP1639375A patent/JPS5839181B2/en not_active Expired
- 1975-02-10 CH CH166375A patent/CH624424A5/en not_active IP Right Cessation
- 1975-02-11 BE BE153254A patent/BE825409A/en not_active IP Right Cessation
-
1983
- 1983-04-21 JP JP6931283A patent/JPS5945701B2/en not_active Expired
- 1983-04-21 JP JP6931183A patent/JPS5945700B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05217083A (en) * | 1992-02-03 | 1993-08-27 | Adobitsuku:Kk | Alarm device with infrared-ray detector |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50110424A (en) | 1975-08-30 |
| DE2505188C2 (en) | 1984-02-16 |
| JPS5945701B2 (en) | 1984-11-08 |
| JPS58194955A (en) | 1983-11-14 |
| BE825409A (en) | 1975-08-11 |
| JPS58194956A (en) | 1983-11-14 |
| NL7501419A (en) | 1975-08-13 |
| ES434567A1 (en) | 1976-12-01 |
| DE2505188A1 (en) | 1975-08-14 |
| CA1037029A (en) | 1978-08-22 |
| JPS5839181B2 (en) | 1983-08-27 |
| FR2260607A1 (en) | 1975-09-05 |
| CH624424A5 (en) | 1981-07-31 |
| IT1007324B (en) | 1976-10-30 |
| GB1486542A (en) | 1977-09-21 |
| FR2260607B1 (en) | 1977-04-15 |
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