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GB1272284A - Unsymmetrical azo and hydrazo compounds - Google Patents

Unsymmetrical azo and hydrazo compounds

Info

Publication number
GB1272284A
GB1272284A GB2111969A GB2111969A GB1272284A GB 1272284 A GB1272284 A GB 1272284A GB 2111969 A GB2111969 A GB 2111969A GB 2111969 A GB2111969 A GB 2111969A GB 1272284 A GB1272284 A GB 1272284A
Authority
GB
United Kingdom
Prior art keywords
give
reacted
alkyl
together form
coor
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
GB2111969A
Inventor
Ronald Edward Macleay
Chester Stephen Sheppard
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.)
US Filter Wallace and Tiernan Inc
Original Assignee
Wallace and Tiernan Inc
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 Wallace and Tiernan Inc filed Critical Wallace and Tiernan Inc
Priority to GB2111969A priority Critical patent/GB1272284A/en
Publication of GB1272284A publication Critical patent/GB1272284A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/06—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent
    • C08J9/10—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a chemical blowing agent developing nitrogen, the blowing agent being a compound containing a nitrogen-to-nitrogen bond
    • C08J9/102—Azo-compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/04—Azo-compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,272,284. Unsymmetrical azo and hydrazo compounds. WALLACE & TIERNAN Inc. 24 April, 1969, No. 21119/69. Heading C2C. [Also in Division C3] Novel compounds I in which R<SP>11</SP> is 1-13 C alkyl, phenyl-1-13 C alkyl, or phenyl, not more than one R<SP>11</SP> being phenyl; A and B are both H or together a further bond; X is a mono-, di- or tri-valent group and n is 1, 2 or 3, wherein (1) when A and B are both H and n is 1, X is -CONR 3 R 4 (R 3 and R 4 are H, 1-20 C aliphatic radicals, or cycloaliphatic radicals or together may form an alkylene biradical); (2) when A and B together form a bond and n is 1, X is (a) -COE where E is NR 3 R 4 , R 5 ,-N(R 3 )-R 13 -N(R 3 )-CO-N= N-C(R<SP>11</SP>) 3 , or -R 13 -CO-N=N-C(R<SP>11</SP>) 3 ; R 5 is a 1-20 C aliphatic, cycloaliphatic or aromatic radical; and R 13 is an aliphatic, cycloaliphatic or aromatic biradical; (b) -C(F)(R 1 )R 2 where R 1 and R 2 are 1-20 C aliphatic or cycloaliphatic radicals and together may be alkylene and R 2 may also be phenyl or substituted phenyl; F is -CN, -CONH 2 , -COOR 6 , -C(NH 2 )=NH, -C(OR 6 )=NH, -C(NH 2 )- NOH, Cl, Br, -OCOH, -OCOR 5 , -OCOOR 5 , -OCOOOR, -SCOR 5 , -SCSR 5 , -SCOOR 5 , -SCSOR 5 , -OR 5 , -SR 5 , -N 3 , -SCN, -OCN, -OOR, -OOCOR 5 , -OOH, -OH, -R 5 , -N(R 10 ) 2 , -NHN(R 5 ) 2 , -NHNHCOOR 6 , -N(COR 1 )COR 2 , -NO 2 , -NO 3 , -C#CR 10 , -O-N=C(R 5 ) 2 , -ON(R 10 ) 2 , -ON(#O) = CR 3 R 4 , -CR 14 (R 15 ) (R 10 ), -Y<SP>11</SP>-C(R 1 ) (R 2 )-N=N-C(R<SP>11</SP>) 3 , or R is -C(R<SP>11</SP>) 3 ; R 6 is 1-13 C alkyl; Y<SP>11</SP> is -S-S-, -NH-NH-, -X<SP>11</SP>-C(=X<SP>11</SP>)-R 13 -C( = X<SP>11</SP>)-X<SP>11</SP>-, X<SP>11</SP>-C( = X<SP>11</SP>)O-R 13 - O-C( = X<SP>11</SP>)-X<SP>11</SP>-, -X<SP>11</SP>-R 13 -X<SP>11</SP>-, -OO-CO-R 13 -CO-OO , -OO-C(R 1 )- (R 2 )-R 13 -C(R 1 ) (R 2 )-OO-,-C(R 14 ) (R 15 )-, or -00-; X<SP>11</SP>is O or S; R 10 is H, or a 1-20 C aliphatic, cycloaliphatic or aromatic radical; R 14 and R 15 are -COOR 10 , -CN, -COR 10 , -NO 2 , -CO-N(R 10 ) 2 , -C(R 10 ) 2 -OCOR 10 , -COOH, -COOM, -CH 3 , -C(R 10 ) 2 OH, -C(R 10 ) 2 -OCOCl, -C(R 10 ) 2 -OCOOR 10 , -C(R 10 ) 2 OCON(R 10 ) 2 , -COCl or -NH 2 ; and R 14 and R 15 can together form -CO-R 13 - CO-, -COOR 13 O-CO-, -CON(R 6 )-R 13 - N(R 6 )-CO-, -C(R 10 ) (OH)-R 13 -C(R 10 ). (OH)-, -C(R 10 )(OCOR 10 )-R 13 -C(R 10 )- (OCOR 10 )-, -C(R 10 ) (O-CO-NR 6 R 6 )-R 13 -C(R 10 ) (O-CO-NR 6 R 6 ), or and M is an alkali metal; (c)-C(R 1 ) (F)-R 13 - C(R 1 ) (F)-N=N-C(R<SP>11</SP>) 3 ; (d) -C(R 6 )= C(R 7 )R 8 where R 7 and R 8 are H or 1-13 C alkyl or together form an alkylene biradical and R 6 and R 8 may together form an alkylene biradical; (e) a radical where Z 1 is the residue of the heterocyclic ring; (3) when A and B together form a bond and n is 2, X is where Z 2 is the monovalent residue of the heterocyclic ring and (4) when A and B together form a bond and n is 3, X is where Z 3 is the divalent residue of the heterocyclic ring; are prepared by procedures given below:- (1) RNHNH 2 is reacted with R 1 COR 2 to give R-NHN = CR 1 R 2 and this is reacted with HCN to give RNHNH-C(R 1 )(R 2 )CN, which on oxidation gives R-N=N-C(R 1 )(R 2 )CN. (2) RNHN = C(R 1 )(R 2 ) is reacted with halogen to give R-N=N-C(R 1 )(R 2 )hal. (3) The product of (2) may be reacted with an appropriate alkaline earth or alkali metal compound M(Y) 1-2 or M 1-2 Y<SP>11</SP> to give R-N= N-C(R 1 )(R 2 )Y or [R-N=N-C(R 1 )(R 2 )] 2 Y<SP>11</SP> where Y is as defined above for F, but is not -CONH 2 , -COOR 6 , -C(NH 2 )=NH, -C(OR 6 )=NH, -(NH 2 )=NOH, Cl, Br or -Y<SP>11</SP>-C(R 1 )(R 2 )-N=N-C(R<SP>11</SP>) 3 . (4) R-N=N-COOR 9 is reacted with HNR 3 R 4 to give R-N=N-CONR 3 R 4 where R 9 is 1-13 C alkyl. (5) R-NHNH 2 is reacted with R 5 COhal to give R-NHNHCOR 5 which may be oxidized to give R-N=N-COR 5 . (6) RNHNH 2 is reacted with a compound where X<SP>1</SP> is halo and Z<SP>1</SP> is Z 1 , Z 2 or Z 3 , to give a compound which on oxidation gives a compound (7) RNHNH 2 .HX<SP>111</SP> is reacted with H 2 NCON(R 11 ) 2 to give R-NHNH-CON(R 11 ) 2 (X<SP>111</SP> is C1-, Br-, I-, SO 4 - or HSO 4 - and R 11 is H or 1-13 C alkyl). (8) R-NHNH 2 is reacted with M<SP>1</SP>CNO to give R-NH-NHCONH 2 (M is H or metal).
GB2111969A 1969-04-24 1969-04-24 Unsymmetrical azo and hydrazo compounds Expired GB1272284A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2111969A GB1272284A (en) 1969-04-24 1969-04-24 Unsymmetrical azo and hydrazo compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2111969A GB1272284A (en) 1969-04-24 1969-04-24 Unsymmetrical azo and hydrazo compounds

Publications (1)

Publication Number Publication Date
GB1272284A true GB1272284A (en) 1972-04-26

Family

ID=10157526

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2111969A Expired GB1272284A (en) 1969-04-24 1969-04-24 Unsymmetrical azo and hydrazo compounds

Country Status (1)

Country Link
GB (1) GB1272284A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998015512A2 (en) * 1996-10-09 1998-04-16 Rhone Poulenc Agrochimie Fungicides with hydroximic and hydrazonic groups

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998015512A2 (en) * 1996-10-09 1998-04-16 Rhone Poulenc Agrochimie Fungicides with hydroximic and hydrazonic groups
WO1998015512A3 (en) * 1996-10-09 1998-07-16 Rhone Poulenc Agrochimie Fungicides with hydroximic and hydrazonic groups

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Legal Events

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PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee