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Azoamide Compounds and Their Use As Initiators for Producing Block

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Azoamide Compounds and Their Use As Initiators for Producing Block Europäisches Patentamt *EP000818440B1* (19) European Patent Office Office européen des brevets (11) EP 0 818 440 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: C07C 245/04, C08K 5/23, of the grant of the patent: C08F 4/04 24.10.2001 Bulletin 2001/43 (21) Application number: 97305061.0 (22) Date of filing: 09.07.1997 (54) Azoamide compounds and their use as initiators for producing block copolymers Azoamid Verbindungen und ihre Verwendung zur Herstellung von Blockcopolymeren Composés azo-amides et leur utilisation comme initiateurs pour la préparation de polymères séquencés (84) Designated Contracting States: (74) Representative: Wotherspoon, Hugh Robert BE DE FR GB IT NL c/o Langner & Parry, 52-54 High Holborn (30) Priority: 11.07.1996 JP 20127896 London WC1V 6RR (GB) 11.07.1996 JP 20127996 (56) References cited: (43) Date of publication of application: EP-A- 0 356 026 DE-A- 4 207 558 14.01.1998 Bulletin 1998/03 JP-A- 4 202 283 (73) Proprietor: WAKO PURE CHEMICAL • CHEMICAL ABSTRACTS, vol. 88, no. 5, 30 INDUSTRIES, LTD January 1978 Columbus, Ohio, US; abstract no. Chuo-ku Osaka (JP) 37278q, XP002064013 & SU 569 561 A (ACADEMY OF SCIENCES, UKRAINIAN S.S.R) (72) Inventors: 25 August 1977 • Maesawa, Tsuneaki, Tokyo Kenkyusho Kawagoe-shi (JP) Remarks: • Shiraki, Kazuo, Tokyo Kenkyusho The file contains technical information submitted Kawagoe-shi (JP) after the application was filed and not included in this • Shimamura, Nobutaka, Tokyo Kenkyusho specification Kawagoe-shi (JP) Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 0 818 440 B1 Printed by Jouve, 75001 PARIS (FR) EP 0 818 440 B1 Description [0001] The present invention relates to an azoamide compound excellent in the solubility in various solvents and useful as a polymerization initiator and to a novel macroazo compound having in one molecule two types of azo groups 5 different from each other in the decomposition activity. [0002] In the recent years, polymeric compounds have progressed from general purpose polymer to functional pol- ymer, and block polymers which can be expected to manifest various functions effectively are being watched with interest. In such a state of things, an attempt to prepare a block polymer by the use of an azo compound was proposed, and a straight chain high-polymeric azo compound having a plurality of azo groups on the main chain obtained through 10 an alternating polycondensation of an azo compound and a bifunctional compound was reported in JP-A-64-62318. However, the polymeric azo compounds reported in the above-mentioned patent gazette were made of a single azo compound, and therefore the azo groups existing on the main chain are all identical with each other in the decomposition activity. Thus, in order to leave a desired portion of the azo groups undecomposed in the first step of polymerization and to use the undecomposed portion of azo group in the second step of polymerization, it was necessary to control 15 the temperature and time of polymerization strictly in the first step of polymerization. Further, the starting azo compound was inferior in solubility, so that no sufficient function as a polymerization initiator could be exhibited. [0003] With the aim of solving these problems, an azo compound obtained by subjecting two kinds of azo compounds different in decomposition activity to a condensation reaction was reported (US Patent No. 3,763,129, No. 3,868,359, No. 3,649,614, No. 3,956,269, etc.). Such azo compounds, however, had at most 2 or 3 azo groups in one molecule, 20 and therefore when such an azo compound was used as a polymerization initiator, the following difficulties arose: (1) a polymer of high molecular weight was difficult to obtain, (2) when the number of azo groups was 2, only an AB type polymer could be obtained, while when the number of azo group was 3, only an ABA type polymer could be obtained (A is a segment derived from a monomer A and B is a segment derived from a monomer B, hereinafter the same), (3) a number of radicals derived from the initiator, not participating in the polymerization, were formed, and (4) the kind of 25 monomer which can be polymerized by this method was limited, because the azo compound was low in solubility in itself. [0004] Chem. Abstr. 88(5), 1978, (AN 88:37278) discloses compounds having terminal amino groups which are not included within the scope of the present invention. The compounds of the present invention have superior solubility in various solvents described later in this application. [0005] WPI-abstract, (AN 92-295452 & JP-A-4202283) discloses azo compounds such as 2,2'-azobis[2-methyl-N- 30 (2-hydroxyethyl)propionamide]. These compounds are poorer solubility to those of the present invention. SUMMARY OF THE INVENTION [0006] In view of the above, it is an object of the present invention to provide a novel azo compound excellent in 35 solubility in various solvents, and to provide a novel macroazo compound obtained from said azo compound and excellent in solubility in various solvents, said macroazo compound being usable as a macroazo initiator for producing a block polymer easily and in a high efficiency without needing any strict control. [0007] The present invention provides an azoamide compound represented by the following formula: 40 45 wherein R1 to R4 are independently an alkyl group; X is an alkylene group; Y is O or NH provided that a plurality of Y may be the same or different; and n is an integer of 2 or more. [0008] The present invention also provides a process for producing the above-mentioned azoamide compound which 50 comprises reacting an azodicarboxylic acid diester compound represented by the following formula: 55 2 EP 0 818 440 B1 5 10 wherein R9 is a lower alkyl group; and R1 to R4 are as defined above, with an aminoalcohol or a diamine represented by the following formula: --H2N-(X-Y)n-1-X-OH-- [4] 15 wherein X, Y and n are as defined above. [0009] The present invention further provides a polymerization initiator comprising the above-mentioned azoamide compound, a polymerization process using said polymerization initiator, a macroazo compound obtained by said po- lymerization process, and a polymerization process of a monomer using said macroazo compound. 20 DESCRIPTION OF THE PREFERRED EMBODIMENTS [0010] The present invention relates to an azoamide compound represented by the following formula: 25 30 wherein R1 to R4 are independently an alkyl group; X is an alkylene group; Y is O or NH provided that a plurality of Y may be the same or different; and n is an integer of 2 or more. [0011] The present invention further relates to a process for producing the above-mentioned azoamide compound 35 which comprises reacting an azodicarboxylic acid diester compound represented by the following formula: 40 45 wherein R9 is a lower alkyl group; and R1 to R4 are as defined above, with an aminoalcohol or a diamine represented by the following formula: --H2N-(X-Y)n-1-X-OH-- [4] 50 wherein X, Y and n are as defined above. [0012] The present invention further relates to a polymerization initiator comprising the above-mentioned azoamide compound. [0013] The present invention further relates to a process for polymerization which comprises using the above-men- 55 tioned azoamide compound as a polymerization initiator. [0014] The present invention further relates to a macroazo compound constituted of repeating units represented by the following formula: 3 EP 0 818 440 B1 5 10 wherein R5 and R7 are independently an alkyl group; R6 and R8 are independently an alkyl group or a cyano group; T is an alkylene group; and R1 to R4, X, Y and n are as defined above; provided that the degree of polymerization of said 15 macroazo compound is 2 or more. [0015] The present invention further relates to a process for producing a macroazo compound which comprises reacting the above-mentioned azoamide compound with an azodicarboxylic acid compound represented by the fol- lowing formula: 20 25 wherein R5 and R7 are independently an alkyl group; R6 and R8 are independently an alkyl group or a cyano group; T is an alkylene group; and E is a hydroxyl group or Z; and Z is a halogen atom. 30 [0016] The present invention further relates to a macroazo initiator comprising the above-mentioned macroazo com- pound. [0017] The present invention further relates to a process for polymerization which comprises using the above-men- tioned macroazo initiator. [0018] The present invention further relates to a process for producing a block polymer which comprises using the 35 above-mentioned macroazo initiator. [0019] The alkyl group represented by R1 to R4 in the formulas [1], [2] and [3] and the alkyl group represented by R5 to R8 in the formulas [2] and [7] may be any of straight chain, branched chain and cyclic alkyl groups, of which examples are lower alkyl groups such as alkyl groups having 1-6 carbon atoms. Specific examples thereof include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl 40 group, a sec-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a 3,3-dimethyl- butyl group, a 1,1-dimethylbutyl group, a 1-methylpentyl group, a n-hexyl group, an isohexyl group, a cyclopropyl group, a cyclopentyl group or a cyclohexyl group.
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