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  • 1
    Electronic Resource
    Electronic Resource
    Photochemical addition reaction of a polymer-bearing pendant vinyl ether with various thiol compounds (1993)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 31 (1993), S. 91-97 
    Details
    ISSN: 0887-624X
    Keywords: photochemical addition reaction ; pendant vinyl ether group ; thiol compound ; photosensitizer ; benzophenone ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Photochemical addition reaction of the pendant vinyl ether group in the polymer (P-1), which was synthesized by the alternate ring-opening copolymerization of glycidyl vinyl ether with phthalic anhydride, with various thiol compounds such as benzenethiol, phenylmethanethiol, 2-mercaptoacetic acid, ethyl 2-mercaptoacetate, N-acetyl-L-cysteine (AcCys), and 1,4-phenylenedi(methylthiol) was carried out using benzophenone (BP) as the photosensitizer in the THF solution. Each reaction proceeded very smoothly to give the corresponding polymers with high conversion, although the degree of reaction of the pendant vinyl ether group in P-1 was affected by the molar ratio between the thiol compounds and the vinyl ether group, and the amounts of photosensitizer BP added. Furthermore, it was also found that optically active polymer containing pendant N-acetyl-L-cysteine residue was synthesized by the photochemical addition reaction of P-1 with AcCys. The reactions of P-1 with dithiol or bisazide compounds occurred effectively to give gel products in the film state, and it was found that the polymer film containing P-1 and those compounds can be applied as negative-type photoresists with high practical photosensitivity. © 1993 John Wiley & Sons, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1993.080310111
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  • 2
    Electronic Resource
    Electronic Resource
    Polyaddition of bisoxetane with diacyl chlorides using quaternary ammonium salts: A novel synthesis of polymers carrying pendant chloromethyl group (1993)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 31 (1993), S. 1639-1641 
    Details
    ISSN: 0887-624X
    Keywords: bisoxetane ; diacyl chloride ; polyaddition ; quaternary ammonium salt ; pendant chloromethyl group ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1993.080310636
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  • 3
    Electronic Resource
    Electronic Resource
    Insoluble polystyrene-bound quaternary onium salt catalysts for the synthesis of cyclic carbonates by the reaction of oxiranes with carbon dioxide (1993)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 31 (1993), S. 939-947 
    Details
    ISSN: 0887-624X
    Keywords: polymer-supported onium salt catalyst ; catalytic effect ; synthesis of cyclic carbonate ; oxirane ; carbon dioxide ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The addition reaction of oxiranes (26a - e) with carbon dioxide (CO2) was performed using insoluble polystyrene beads containing pendant quaternary ammonium or phosphonium salts as catalysts under atmospheric pressure. The reaction of 26a - e with CO2 proceeded smoothly catalyzed by 1-2 mol % of the polymer-supported quaternary onium salts to give the corresponding cyclic carbonates (27a - e) in high yields at 80-90°C. In this reaction system, the catalytic activity of the polymer-supported quaternary onium salts was strongly affected by the following factors: degree of ring substitution (DRS) of the onium salt residues to the polymer, degree of crosslinking (DC) of the polystyrene beads, chain length of the alkylene spacer between the polymer back-bone and the onium salt, hydrophobicity of the alkyl group on the onium salts, and kind of onium salts. That is, the polymer-supported quaternary phosphonium salts with low DRS and DC and with long alkylene spacer chain were found to have higher catalytic activity than low molecualr weight quaternary onium salts. The above polymer-supported catalysts can easily be separated at the end of a reaction by filtration and can be reused for at least seven runs. It was also found that the rate of reaction was proportional to the products of catalyst concentration and oxirane concentration. © 1993 John Wiley & Sons, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1993.080310412
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis and thermal crosslinking reaction of polymers containing pendant carboxyl and epoxy groups (1996)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 34 (1996), S. 1951-1957 
    Details
    ISSN: 0887-624X
    Keywords: p-vinylbenzyl glycidyl ether ; itaconic acid monomethyl ester ; radical polymerization ; polymer yield ; gel fraction ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Polymers containing both pendant carboxyl and epoxy groups were synthesized by the radical copolymerization of p-vinylbenzyl glycidyl ether (VBGE) and itaconic acid monomethyl ester (IAME). The copolymerization proceeded smoothly under various conditions, and polymer soluble in 1,4-dioxane with no gel fraction was obtained. However, the carboxyl-epoxy addition reaction between VBGE and IAME was observed, when DMSO or DMF were used as polymerization solvents. The IR and 1H-NMR spectrum of copolymers of VBGE and IAME showed the corresponding structure. The thermal crosslinking reaction of the resulting copolymers was examined under various conditions. Tetrabutylammonium bromide (TBAB) showed catalytic activity for the reaction. However, a 100% gel fraction of polymer was achieved after only 15 min without any catalyst, when the crosslinking reaction was performed at 150°C. © 1996 John Wiley & Sons, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis of new hybrid monomers and oligomers containing cationic and radical polymerizable vinyl groups and their photoinitiated polymerization (1996)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 34 (1996), S. 217-225 
    Details
    ISSN: 0887-624X
    Keywords: hybrid monomer ; hybrid oligomer ; photoinitiated cationic polymerization ; photoinitiated radical polymerization ; vinyl ether moiety ; acrylate moieties ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New hybrid vinyl monomers with both cationic- and radical-polymerizable vinyl groups were synthesized by the reaction of bis[1(chloromethyl)-2-(vinyloxy)ethyl]terephthalate (3) with unsaturated carboxylic acids using 1,8-diazabicyclo[5.4.0]-undecene-7 (DBU) as a base. The reaction of 3 with methacrylic acid 4a was carried out using DBU in DMSO at 70°C for 24 h to give an 86% yield of the hybrid vinyl monomer (5a). Polycondensation of 3 with unsaturated dicarboxylic acids was also performed using DBU to give hybrid vinyl oligomers with radical polymerizable C (DOUBLE BOND) C groups (VR) in the main chain and cationic polymerizable vinyl ether moieties (VC) on the side chain. The photopolymerization of these hybrid vinyl compounds proceeded smoothly in bulk using either a cationic photoinitiator such as a sulfonium salt or a radical photoinitiator such as acyl phosphine oxide under UV irradiation. © 1996 John Wiley & Sons, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesis of polysulfonates containing reactive pendant chloromethyl groups by the polyaddition of bisepoxides with disulfonyl chlorides (1998)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 36 (1998), S. 249-256 
    Details
    ISSN: 0887-624X
    Keywords: polysulfonate ; reactive chloromethyl groups ; polyaddition ; bisepoxide ; disulfonyl chloride ; quaternary onium salt ; catalyst ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Polysulfonates with reactive pendant chloromethyl groups were synthesized by polyadditions of bisepoxides with disulfonyl chlorides. The polyaddition of bisphenol A diglycidyl ether (BPGE) with m-benzene disulfonyl chloride (m-BDSC) occurred in anisole without any catalyst at 130°C for 24 h. However, polymer with high molecular weight was not obtained. On the other hand, the polyadditions of BPGE with m-BDSC proceeded very smoothly with high yield (81-91%) to give polymers with relatively high molecular weights in anisole at 130°C for 24 h when quaternary phosphonium salts were used as catalysts. The polyaddition was also enhanced by the addition of certain crown ether complexes. However, the catalytic activity of these compounds was less than those of quaternary phosphonium salts. Furthermore, polyadditions of certain bisepoxides with disulfonyl chlorides were also carried out to produce the corresponding polymers under the same reaction conditions. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 249-256, 1998
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis of polymers with pendant hydroxyl groups by polyaddition of bis(oxetane)s with dithiols (1998)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 36 (1998), S. 2873-2880 
    Details
    ISSN: 0887-624X
    Keywords: polyaddition ; bis(oxetane) ; aromatic dithiol ; catalyst ; quaternary onium salt ; crown ether complex ; new reactive polymer ; pendant primary hydroxyl group ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Addition reaction of (3-methyl-3-oxetanyl)methyl acetate (MOMA) with bis(4-mercaptophenyl) sulfide (BMPS) was examined in certain organic solvents. When the reaction of MOMA with BMPS was performed without any catalyst in hexamethylphosphoric triamide (HMPA) and N-methyl-2-pyrrolidone (NMP) at 130°C for 24 h, conversions of the corresponding adduct were 96 and 36%, respectively, which was confirmed by 1H-NMR spectra. On the other hand, when the reaction was carried out using tetraphenylphosphonium bromide (TPPB) as a catalyst under the same conditions, conversions of the adduct were 96 and 81% in HMPA and NMP, respectively. This result shows that although the addition reaction of oxetane compound with aromatic dithiol proceeds without any catalyst in HMPA, the reaction was strongly enhanced by adding TPPB in NMP. On the basis of the above results, polyadditions of bis((3-methyl-3-oxetanyl)methyl) terephthalate (BMOT) and bis((3-ethyl-3-oxetanyl)methyl) terephthalate with BMPS were performed using TPPB as the catalyst in NMP at 130°C for 24 h. As a result, the corresponding high molecular weight polymers 1 (Mn = 22,400) and 2 (Mn = 12,800) with pendant primary hydroxyl groups were obtained in 83 and 89% yields without any gel products, respectively. Furthermore, a low molecular weight oligomer was obtained from the polyaddition of BMOT with aliphatic dithiol, bis(mercaptomethyl)benzene, under the same reaction conditions. The catalytic activity on the polyaddition of BMOT with BMPS was also examined, and it was found that thermally stable TPPB and crown ether complexes at the reaction temperature (130°C) have higher catalytic activity than tetrabutylammonium bromide and tetrabutylphosphonium bromide to produce polymer 1 with high molecular weight. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 2873-2880, 1998
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 8
    Electronic Resource
    Electronic Resource
    Synthesis of polyethers containing viologen moiety and their application to electron-transfer catalyst (1990)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 28 (1990), S. 2509-2516 
    Details
    ISSN: 0887-624X
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Polyethers containing viologen moieties were prepared by the reaction of tosylated polyethers with bipyridine. Viologen moieties of these polymers having — ((CH2)2—O—)n — chains were reduced into the cation radicals by sodium dithionite in dichloromethane, methanol, and benzene. The reduction of vicinal dibromide, ethyl 2,3-dibromo-3-phenylpropionate using these polymers as electron-transfer catalyst (ETC) was performed in dichloromethane to obtain ethyl cinnamate in good yield.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1990.080280923
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  • 9
    Electronic Resource
    Electronic Resource
    Photogeneration of polyfunctional amines and novel thermal curing reactions of epoxy resin and polyurethane oligomer using these amines (1993)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 31 (1993), S. 3013-3020 
    Details
    ISSN: 0887-624X
    Keywords: polyfunctional amine ; photogeneration ; thermal curing reaction ; epoxy resin ; polyurethane oligomer ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Photochemical reactions of various blocked polyfunctional amines such as bis(4-formylaminophenyl)methane (FAPM), bis(4-acetylaminophenyl)methane (AAPM), bis(4-benzoylaminophenyl)methane (BAPM), 2,4-diformylaminotoluene (DFAT), m-xylene diformamide, and bis[[(2-nitrobenzyl)oxy]carbonyl]hexane-1.6-diamine were carried out to give the corresponding free amines in THF solution, in epoxy resin, or in polyurethane oligomer with terminal isocyanate groups. Photolysis of FAPM and DFAT to produce the corresponding polyfunctional amines such as 4,4'-methylenedianiline and 2,4-diaminotoluene proceeded with 80 and 75% conversions, respectively, in THF solution under UV irradiation at 5 h. AAPM and BAPM also produced the corresponding photo-Fries rearrangement products with 32 and 38% conversions, respectively, under the same irradiation conditions. The photolysis of those compounds also occurred with similar conversions in the epoxy resin and in the polyurethane oligomer under UV irradiation; and the thermal curing reactions of the epoxy resin and the polyurethane oligomer with photogenerated polyfunctional amines proceeded smoothly after heating at 140°C for 2 hrs. © 1993 John Wiley & Sons, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1993.080311217
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesis and photochemical properties of solar energy storage-exchange polymers containing pendant norbornadiene moieties (1994)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 32 (1994), S. 2765-2773 
    Details
    ISSN: 0887-624X
    Keywords: new photoresponsive polymer ; pendant NBD moiety ; photochemical reaction of NBD ; photosensitization ; catalytic reversion of QC ; stored thermal energy ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New photoresponsive polymers 1-4 containing pendant norbornadiene (NBD) moieties with N,N-disubstituted amide groups were synthesized with 97, 98, 92, and 94% conversions by the substitution reaction of poly (p-chloromethyl) styrene] with potassium salts of 3piperidyloxo-2,5-NBD-2-carboxylic acid, 3-(NN-dipropylcarbamoyl) -2,5-NBD-2-carboxylic acid, 3-(N-methyl-N-phenylcarbamoyl)-2,5-NBD-2-carboxylic acid, and 3-(N,N-dipheylcarbmoyl)-2,5-NBD-2-carboxylic acid, respectively, using tetrabutylammonium bromide as a phase transfer catalyst for all. Polymers 1-4 with N,N-disubstituted amide groups on the NBD moieties were sensitized by adding appropriate photosensitizers such as Michler's ketone and 4- (N,N-dimethylamino) benzophenone in the film state, although the reactivities of the polymers without photosensitizer were lower than that of our previously reported polymer 5 containing pendant 3- (N-phenylcarbamoyl) -2,5-NBD-2-carboxylate moiety. It was also found that the photo-irradiated retaining polymers 1-4 containing the corresponding QC moieties can be stored about 80-86 kJ/mol of their thermal energy. © 1994 John Wiley & Sons, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pola.1994.080321417
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