Synthesis and properties of photosensitive rubbers. II. Photosensitivity of cyclized polydienes and polypentenamer with pendent cinnamate groups

Azuma, Chiaki; Sanui, Kohei; Ogata, Naoya

doi:10.1002/app.1982.070270619

Cited by 21 publications

(10 citation statements)

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“…The quality of curve fitting is conveyed in Figure 5, which also reveals the failure of simple first-and second-order reactions without exp(-t/τ) 40,41 to capture the asymptotic behavior in X. …”

Section: Chart 1 Polymers Monomers and Dimers I And Ii Synthesizedmentioning

confidence: 99%

New Insight into Photoalignment of Liquid Crystals on Coumarin-Containing Polymer Films

et al. 2006

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Polymers containing 6-and 7-substituted coumarin moieties were prepared as photoalignment films through linearly polarized UV irradiation to a varying fluence for an investigation of liquid crystal orientation. Model coumarin monomers and dimers were also synthesized and characterized as part of a novel approach to the interpretation of liquid crystal orientation in terms of monomer conversion. The experimental results for monomer conversion as a function of fluence were used to validate the first-order kinetics with an exponentially decaying rate constant as the reaction proceeds. A kinetic model was constructed to describe the evolutions of the orientational order on the parts of the reacted and the unreacted coumarin moieties. The model was instrumental to the visualization of liquid crystal orientation on photoalignment films at the early and the late stages of dimerization. Furthermore, the observed crossover in liquid crystal orientation on the polymer film comprising 7-substituted coumarin moieties was successfully interpreted by considering three factors: the relative abundance of the reacted and the unreacted coumarin moieties, the degrees of their orientational order predicted by the kinetic model, and the energetics of molecular interaction.

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Section: Chart 1 Polymers Monomers and Dimers I And Ii Synthesizedmentioning

confidence: 99%

New Insight into Photoalignment of Liquid Crystals on Coumarin-Containing Polymer Films

et al. 2006

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“…4,5 It has been found that chains and present some characteristics of microphase separation. small variations in the polymer structure may promote expressive changes in chain mobility, 17,18 In the solid state, the behavior to be expected 5268 / 8E45$$5268 05-16-98 10:56:03 polaal W: Poly Applied …”

Section: Resultsmentioning

confidence: 98%

“…The maleic residues were then esterified behavior with chemical structure. [3][4][5] One of the with glycol cinnamates, giving rise to half-esters, features required to improve reactivity seems to in which the cinnamate groups were separated be chain mobility. In this regard, polydienes have from the main chain by segments of different lengths.…”

Section: Introductionmentioning

confidence: 97%

“…4,6 To begin with, a continuous increase in the concentration of reactive Polymers sensitive to ultraviolet (UV) irradiation are widely used as photoresists, applied onto Cugroups improves reactivity only up to a certain value, after which any further increment does not covered plates in the manufacture of printed circuits. In the case of negative photoresists, irradiausually have a positive effect, due to mobility restrictions imposed by the crosslinks already tion promotes crosslinking of the photosensitive formed.…”

Section: Introductionmentioning

confidence: 99%

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UV-light induced crosslinking reaction of cinnamate natural rubbers: Effect of the spacer length, counter-ion nature, and content

Visconte¹,

Andrade²,

Azuma³

1998

J. Appl. Polym. Sci.

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“…We had revealed the dependence of the photosensitivity on the glass-transition temperature of the polymer theoretically and experimentally in the case of the cyclized polydiene rubbers and linear polydiene rubbers having cinnamate groups. [12][13][14][15] This paper describes the synthetic conditions of a new type of photoresist by means of the reaction of polybutadiene and polypentenamer with various chloroacetic acids, and also the influence of the polymer structure on the photosensitivity of chloroacetylated polybutadiene in terms of the glass transition temperature of the polymer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of photosensitive rubbers. III. Synthesis of chloroacetylated polybutadiene and its photosensitivity

Azuma

Hiramatsu

Tanaka

et al. 1984

J of Applied Polymer Sci

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SynopsisPolymers having chloroacetate groups were prepared by addition reaction of various chloroacetic acids, such as mono-, di-, and trichloroacetic acids, to cis-1,4-polybutadiene under nitrogen atmosphere for obtaining photosensitive rubbers. The structure of products obtained was identified as a cyclized polybutadiene having pendent chloroacetate groups. The amount of the incorporated substituent increased up to the maximum of around 20 mol %, and the amount of the residual unsaturated groups in the polymer backbone decreased due to the cyclization of the double bond. Chloroacetylated polybutadiene had higher photocrosslinkability by UV irradiation than chloroacetylated chitosan or PVA owing to the high reactivity of the chloroacetate groups and the double bonds in the polymer. The photosensitivity depends both on the amount of the incorporated chloroacetate groups and the residual double bonds in the polymer and also depends on the glass transition temperature (T,) of the polymer, and the dependence of the crosslinking reaction on Tg was interpreted to be due to diffusion controlled reaction between excited dichloroacetate groups and olefinic groups in the polymer. INTRODUCTIONWe had found that1 when a chitosan whi'ch can be obtained by the hydrolysis of chitin having N-acetylglucosamide units was chloroacetylated, the chitosan could easily be photocrosslinked by UV irradiation. The mechanism of the photocrosslinking reaction was investigated by using isopropyl chloroacetates as model compounds. Moreover, the photosensitive chloroacetate groups were incorporated into poly(viny1 alcohol) for obtaining a new type of photopolymer.2Poly(viny1 cinnamate) -type photoresists and cyclized polydienes rubbers used together with photocrosslinking reagents, such as bisazides, are already commercialized and are widely used as photoresists.3-5 It is known that6 carboxylic acids add to olefinic compounds to yield the corresponding esters in the presence of acid catalysts, such as p-toluenesulfonic acid or perchloric acid. It had been reported that saturated carboxylic acids including acetic acid add to polydienes to yield cyclized polydiene rubbers having pendent carboxylate group^.^.^ Therefore, we made an attempt in order to obtain cyclized polydiene rubbers having cinnamate groups by using the reaction of polydienes with cinnamic acid in the presence of acid catalysts, which was reported in a previous paper.g It is known thatlOJ1 the glass transition temperature of photosensitive polymers greatly influences the photosensitivity, because the photocrosslinking reaction takes place in a solid state, where the mobility of the polymer influences the photochemical reaction. We had revealed the dependence of the photosensitivity on the glass-transition temperature of the polymer theoretically and experimentally in the case of the cyclized polydiene rubbers and linear polydiene rubbers having cinnamate groups.12-15 This paper describes the synthetic conditions of a new type of photoresist by means of the reaction of polybutadi...

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Synthesis and properties of photosensitive rubbers. II. Photosensitivity of cyclized polydienes and polypentenamer with pendent cinnamate groups

Cited by 21 publications

References 1 publication

New Insight into Photoalignment of Liquid Crystals on Coumarin-Containing Polymer Films

New Insight into Photoalignment of Liquid Crystals on Coumarin-Containing Polymer Films

UV-light induced crosslinking reaction of cinnamate natural rubbers: Effect of the spacer length, counter-ion nature, and content

Synthesis and properties of photosensitive rubbers. III. Synthesis of chloroacetylated polybutadiene and its photosensitivity

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