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The event-related potential and motor reaction time were simultaneously recorded in 35 patients with Parkinson's disease (26 nondemented and nine demented) and 15 age-matched neurologically normal control subjects during the performance of visual discrimination tasks. There were no significant differences in either the latency or amplitude of the P300 component between the nondemented patients and the control subjects, but the patients with nondemented Parkinson's disease had a significantly prolonged reaction time compared with the controls. In patients with demented Parkinson's disease, both P300 latency and reaction time were significantly prolonged compared with the normal controls. These results suggest that response selection and execution are impaired in patients with nondemented Parkinson's disease, although the stimulus evaluation process is largely preserved, whereas patients with demented Parkinson's disease have impairment of stimulus evaluation, go/no-go response selection, and execution.

Event-related potentials were recorded for 29 patients with multiple cerebral infarcts (MCI) (mean age, 65.7 years) during visual discrimination tasks to clarify the relationship between computed tomographic findings (CT) and P300 component. P300 latency in patients with MCI was significantly longer than that of 15 age-matched normal subjects (mean age, 65.4 years), although no significant difference was found in P300 amplitude between the two groups. There was a significant negative correlation between P300 latency and mental status as determined by the Hasegawa's Dementia Scale. Significant correlation was also found between P300 latency and the degree of ventricular dilatation or severity of periventricular lucency (PVL) on CT scan. P300 latency was not significantly correlated with the number of infarcts. P300 latency in patients with MCI thus appears related to the severity of PVLs and degree of ventricular dilatation in addition to mental status.

Cerebral blood flow and P300, a long-latency, positive component of the scalp-recorded, event-related potential (ERP), were measured in 26 patients with multiple cerebral infarcts (mean age, 65.0 years). Compared with age-matched normal subjects, patients with multiple cerebral infarcts had significantly lower cortical blood flow values and had prolongation of the P300 latency. There was a significant correlation between the P300 latency and the mean cortical blood flow values in patients with multiple cerebral infarcts. These results suggest that, in patients with multiple cerebral infarcts, the cognitive impairment associated with change of the ERP may be related to reduction of cortical blood flow.

The behavior of photofading of some anthraquinone, azo and quinophthalone disperse dyes, and coumarin derivatives on polyester or polyamide film hasbeen examined, The effect of Annellation on the fading and the mechanism of photofading reaction of these dyes and derivatives were discussed, 6, 7-Benzo(Annellation) derivatives of 1, 4-diamino- and 1, 4-dimethyl-amino-anthraqttinone were more resistant to photefading than the compounds that did not contain this configuration, 2-Hydroxy-1-naphthylazobenzene faded to light more rapid than the corresponding 2-hydrexyazobenzene. 3, 4-Benzo coumarin faded much less, and 5, 6-, 6, 7- and 7, 8-benzo derivatives faded more rapid than coumarin. The photofading of 5, 6- and 6, 7-benzoquinophthalones were more sensitive than that of quinophthalone. 5, 6-Benzo derivative faded much less and 6, 7-benzo derivative more rapid than the parent in hydroxyquinophthalone.

New trisazo dyes from 3,5-bis(p-aminophenyl)-1,2,4-triazole and 2,5-bis(p-aminophenyl)-1,3,4-oxadiazole which are found to have no toxicity and no carcinogenicity, and 2,5-bis(p-aminophenyl)imidazole have been prepared to replace benzidine type dye, Direct Deep Black EX. Dyeing with these dyes was carried out on cotton, silk, wool and 6-nylon. These dyes have been shown to have very good dye-ability and also to be very similar to benzidine type dye in colour and fastnesses to light and washing.

The behavior of photofading, of some azodisperse dyes containing nitr, group has been examined on polyester and o n polyamide films, The contributionof nitro group on the an, 4-nitro-4-hydroxy, malous photofading, of thesedyeswas discussed, 4rNitro-2 -hydroxy-4-, 4-nitro-2, , 4-dihydroxy-and 4-nitro-4-N-biscyan, ethyl in, az, benzenes, n p, lyamide fade It is observe thst there by light easier th he corresponding P ed deri is a correlation between the basicity of a dye and its sensitivity to the anomaleus photofading. Anomolous fading of a dye proceeds easily when it is less basic, and 4-nitro-4 -N, N-diethylaminoazobenzene dp. es not show the c, . haracter. The spec3. fioc anomqlous fading of 4-nitroazobenzenes on polyamide may be explained by the assumption that the nitro group can be photoreduced to amino group prior to photooxidation of azo group to azoxy group.2-Nitroazobenzenes on polyester and on polyamide fade by light much more easily than the corresponding 4-nitro derivatives. In anaerobic coRdition, 4-nitroazobenzenes are more resitant to fading than that in normal condition, however, the fading of 2-nitro-azobenzenes does not change practically in both conditions. The anomalous fading of 2-nitroazobenzenes is position specific and may be explained by the assumption that intramolecular photo-oxidation of azo group to azoxy group Proceeds exc usively by 2-nitro group. The behavior of fading of 2, 4-dinitroazobenZeneS has also been examined and discussed.

ナフトールAS型の下づけ剤にピラゾロン環を有するものを合成し,その色調,および染色堅ろう度をしらべた。下づけ剤はいずれも,1-フェニル-3-メチル-5-ピラゾロンを出発原料とし,その4-位にジアゾ化した置換ニトロアニリン類をアルカリ性でカップリングし,ついで還元することにより合成したアミノ化合物とβ-オキシナフトエ酸との縮合により合成した。その中間体となるアミノ化合物は,4-(2'-アミノフェニルアゾ)-,4-(3'-アミノフェニルアゾ)-,4-(4'-アミノフェニルアゾ)-,4-(2'-クロル-5'-アミノフェニルアゾ)-,4-(2'-メチル-5-アミノフェニルアゾ)-,4-(4'-メトキシ-5'-アミノフェニルアゾ)-,4-(2'-アミノ-4'-メトキシフェニルアゾ)-1-フェニル-3-メチル-5-ピラゾロンである。これらをβ-オキシナフトエ酸と常法により縮合し,下づけ剤として木綿上で各種ナフトール染料顕色剤と組合わせて顕色した結果,特長ある色調として,4-(2'-アミノフェニルアゾ)-,4-(2'-クロル-5'-アミノフェニルアゾ)-1-フェニル-3-メチル-5-ピラゾロンより誘導される下づけ剤と,バリアミンブル-B,あるいはFGとの組合わせで緑色系に顕色した。

Differences in colors and their fastness have been investigated by changing the alkyl group to methyl, ethyl, n-propyl and n-butyl in Fast Blue RR type developing agent (2-benzoylamino-5-aminohydroguinone dialkyl ether) or by changing the alkyl group of Violet Base Chiba III type (having 2-p-cresoxyacetamino group in Fast Blue RR type).The result indicated that the coloration was in order of n-propyl

The partial molal volumes of methane-, benzene-, m-benzenedi-, tolyl- and p-toluenesulphonic acids in water solution have been determined by a buoyancy method. Since the concentration of sulphonic acids in water solution used in this experiment was extremly dilute, the partial molal volume _??_0 might be identical with the apparent molal volume φ. The latter can be determined from the specific gravities and concentrations of the sulphonic acid solutions from the following equation: φ=(V-n1V0)/n2 (1) where, V is the total volume of solution containing n1 moles of water and n2 moles of solutes, V0 the volume occupied by a mole of pure water.An attempt has been made to estimate the partial molal volume of imaginary ion, -SO3-, in water solution on the basis of simple model. The partial molal volume of imaginary ion, -SO3-, has been deduced to 35ml/mole from the experimental data.The deduced value for -SO3- is considerably larger, but lower than the calculated value, 52ml/mole, from the bond distance of S-O, and the van der Waals' radius of oxygen following the treatment of Mukerjee. This discrepancy has been explained in terms of an “effective charge”, which is higher than the formal charge. The considerably larger partial molal volume of -SO3-, deduced from the experimental data, indicates that the water structure surrounding the imaginary ion may be broken by the weak ion-dipole interaction.

Die Loslichkeiten folgender Verbindungen wurden in Wasser bei 5°-Intervallen von 0° bis 40° bestimmt; Anilin, Mtrobenzol, Chlorbenzol,β-Oxynaphthalin undα-Nitronaphthalin. Aus diesen Ergebnissen wurden die thermodynamischen Parameter fur den Losungsprozes der reinen flussigen Verbindungen in Wasser berechnet. Das Resultat wurde mit Hilfe des Begriffs der „Eisberge“ erklart. Beim Benzol, Anilin und Chlorbenzol waren die Losungswarmen negativ bei niedrigeren Temperaturen und wurden mit steigender Temperatur positiver. Dagegen traten beim Nitrobenzol,β-Oxynaphthalin undα-Nitronaphthalin stets die positiven Losungswarmen auf. Dies sollte auf die grosen intermolekularen Krafte in der reinen Flussigkeit zuruckzufuhren sein.

The equilibrium adsorption of Orange II by Vinylon has been investigated over a wide range of the dye concentration in the dyebath. The internal adsorption isotherms have been calculated from the results. They differ considerably from the linear form assumed in the formulation of the dyeing theory and far from a Langmuir or a Freundlich relation.Taking into consideration a heterogeneity of the fibre, it has been assumed the Vinylon surface to be composed of three groups of dyeing sites having the different affinities for dye. The internal adsorption isotherms may be represented by the following equation-assuming a Langmuir adsorption of the dye on each group of dyeing sites-.The amount of dye adsorbed on the fibre surface was calculated using the equation (1). There was good agreement between the observed and the calculated values.The saturation values [S] for each group of dyeing sites was independent of the concentration of salt in the dyebath but K for each group considerably dependent of that.The heat of dyeing for each group of dyeing sites was calculated. It was found that there were large differences in the heat of dyeing between the groups dyeing sites.

ω-ジメチルアミノプロピオフェノン基を有する各種染料を合成し,これらの,6-ナイロン(アミラン),絹,ピスコースレーヨンに対する反応性を検討した。さらにカシミロンFに対してカチオン染料としての適用性も調べた。本染料の合成は,アセトフェノン型アゾ染料,あるいは,アントラキノン染料(母体染料)をさきに合成し,これらをMannich反応によってジメチルアミン塩酸塩およびパラホルムアルデヒドと縮合させることによった。本染料を用いて6-ナイロン,絹を酸性染色,ビスコースレーヨン,絹を中性染色し,アルカリ処理によって固着させた。なお繊維と未結合の染料はソーピングおよびピリジン,アセトン抽出によって除去した。染料の固着はすべて良好であったが,6-ナィロンではとくにすぐれていた。スルホン酸基を有する染料の方が染着,固着がよかった。このほかカシミロンFに対するカチオン染料としての染色では,スルホン酸基を有する両性の染料での固着はおとっていた。これらの判定は肉眼によるもののほか,Kubelka-Munk式のK/S値より固着率を計算で求めた。色調は黄,だいだい,赤,紫,青色系統であり,堅ロウ度は日光,洗タク,摩擦ともすぐれていた。染料-繊維間の共有結合生成の証拠およびその反応形式は既報と同様の方法で確かめた。

Isotherms were measured for the distribution of dioxyethylaminoazobenzene (as a model of disperse dye) between water and benzene in the presence and absence of urea or sodium chloride at 10°, 20° and 30°C. From the results the thermodynamic parameters were calculated for the following process which consists of the transfer of one mole of the dye from a water environment to a benzene one.Dye in water (mole fraction Xw)→dye in benzene (mole fraction XB) (A)The changes in the enthalpy and in the unitary free energy and entropy were zero, -3280 cal. (20°C) and +11 e. u.. respectively. It is seen that the process is nearly athermal and accompanied by a considerably large increase in the entropy. It is therefore clear that the affinity of the dye for benzene (negative unitary free energy change for the process (A)) is not caused by an energetic situation. It is associated entirely with a positive unitary entropy change.The positive unitary entropy change for the process (A) strongly indicates the formation of so called “iceberg” water structure in the vicinity of the dye molecule in a water environment. The concept of “iceberg formation” can offer account for the origin of the positive unitary entropy change. When the dye leaves a water environment and enters a benzene one, the “iceberg” around the dye molecule will melt. For this “melt” of “iceberg” again in entropy may be expected.The approximate number of water molecules in the “iceberg” around the dye estimated from the thermodynamic parameters was 20.The thermodynamic parameters for the process (B) were culculated also.Dye in water (mole fraction XW)→dye in urea or sodium chloride solution (mole fraction XS01) (B)The unitary free energy change in the transfer of the dye from a pnre water to the 5 mole urea aqueous solution was -840 cal. The negative unitary free energy change indicates that the urea acts to stabilize the dye molecule in an aqueous environment It has been said that the urea breaks the “iceberg”, perhaps by some favourable interaction with the “iceberg” regions or by formation of structures similar to urea-hydrocarbon clathrates. According to this hypothesis the transfer of the dye molecule to the urea solution may be caused by an entropic situation.The unitary free energy change corresponding to the transfer of the dye to the 1 mole sodium chloride aqueous solution was +480 cal. The positive unitary free energy change indicates that the salt acts to unstabilize the dye molecule in an aqueous environment. Kauzmann's assumption that the salt has an effect in promoting the “iceberg formation” can be used to account for this result. The low affinity of the dye for the salt solution may be caused by a large entropy loss resulting from an increase in the extent of the “iceberg” around the dye molecule in the salt solution.From the results of this study it is reasonable to assume the “iceberg formation” in the vicinity of disperse dyes in a water environment, and there is a possibility that the “hydrophobic bond” may play some imprortant role in the interaction between disperse dyes and hydrophobic fibre.

The solubilities of the following compounds in water andp-toluenesulphonic acid aqueous solution were determined at 5, 25 and 40 ‡C: azobenzenep-aminoazobenzene,p-hydroxyazobenzene,p-N, N-dimethylaminoazobenzene and 1-phenylazo-4-aminonaphthalene. Prom the results the thermodynamic parameters for the transfer of one mole of the compound from water top-toluenesulphonic acid aqueous solution were calculated. It was found that the process was nearly athermal: furthermore, it was invariably accompanied by a positive unitary entropy change. The solubilizing mechanism of aromatic sulphonic acids was explained in terms of an adduct-formation with the compound to be dissolved by means of hydrophobic and nonpolarvan der Waals interactions.

Disperse dyes were synthesized from 1, 2, 3, 4-tetrachloroanthraquinone. They showed good dyeing properties for Tetoron through high pressure dyeing treatment, although their properties for Acetate were not satisfactory. The dyes containing aryl group showed sun-fastness of 6 grade or above and sublimation-fastness of 4-5 grade. Even the dyes without aryl group showed improved fastness against sunlight, abrasion, washing, and sublimation over the corresponding 1, 4-disubstituted anthraquinones.

合成繊維,特にポリアクリロニトリル系繊維に対する良好なケイ光増白染料をうるための一つの試みとして,イソニコチン酸-,α,α'-ジピコリン酸-またはα,β'-ジピコリン酸-クロリドとo-アミノフェノール誘導体を縮合したのち脱水閉環することにより,ピリジン環を有するオキサゾール化合物,すなわちγ-ベンズオキサゾリル-(2)-(I),α,α'-ビス(ベンズオキサゾリル-(2))-(III),α,β'-ビス(ベンズオキサゾリル-(2))-ピリジン(V),およびそれぞれ相当する5-メチル誘導体(II),(IV),(VI)を合成した。さらにIおよびIIをベンゼン中,ジメチル硫酸で処理してピリジニウム塩型の(VII)および(VIII)を得た。これらの化合物を用いてポリアクリロニトリル系繊維(カシミロン-F,ボンネル-W,エクスラン-L),アセテート,ビニロンおよびアミラン(ナイロン6)を増白した。III,IVを除いてすべて可視部にケイ光を有するがII,II,VIIおよびVIIIで処理したアクリル系繊維が最も良好に増白された。この場合IおよびIIはカチオン型のVIIおよびVIIIと同様に,アクリル系繊維に対して繊維中の酸性基と,イオン交換的に染着するが,他の繊維に対する染着挙動は分散染料の場合と同様である。このような染着挙動の相異は,吸着等温線の決定,増白布のケイ光スペクトルの測定および溶液に酢酸,硫酸およびベンゼンスルホン酸を添加した際の吸収およびケイ光スペクトルの変化からも認められた。増白布の日光堅ろう度は,総体的に十分ではないが,アクリル系繊維上におけるI,II,VII,VIIIが比較的良好であった。

アリール-β-クロルエチルスルホン類は対応するアリールメルカプタンにエチレンクロルヒドリンを作用せしめるか,あるいは活性ハロゲンを有する化合物にメルカプトエタノールを処理して得られるβ-オキシエチルスルフィドを塩化チオニルまたは五塩化リンで塩素化してクロルエチルスルフィドを得,更にこれを過酸化水素で酸化して得られる。また対応アリールスルフィン酸にエチレンクロルヒドリンを処理し, 後塩素化しても得られる。β-クロルエチルスルホンをアルカリ性で脱塩化水素化するとアリールビニルスルホン類が合成される。このように合成した置換フェニル-β-クロルエチルスルホンおよび置換フェニルビニルスルホン類はメタノール,エタノール,ブタノールなどのアルコール類と弱アルカリ性でミハエル様付加反応を行うことを確かめた。またアミンとしてモルホリンを用い,同様の付加反応がアミン類にも容易に行われることを確かめた。

クマリン誘導体および関連化合物の光退色挙動がポリアミドあるいはポリエステルフィルム上において調べられた。そしてこの光退色における濃度依存性が退色特性曲線を用いて検討された。3-フェニル-4-メチルクマリンと2,6-ビスベンゾオキサゾリルナフタレン誘導体の日光堅ろう度はその染着濃度の増加とともに向上する。しかしながら, 4-メチル-7-メトキシクマリン, 4-メチル-7-ジエチルアミノクマリン, 3-フェニルクマリン, 3-フェニル-7-(3'-メチルピラゾリル)クマリンおよびベンゾオキサゾリルエチレン誘導体の場合には, 異常退色 (負勾配をもつ退色特性曲線), つまり染着濃度の増加とともに日光堅ろう度の低下がみられる。これらの知見と溶液状態におけるクマリンおよび関連化合物の光化学反応の結果から, 退色特性曲線が負の勾配をもつ現象と二量化反応の関係について考察した。

モルホリン環を置換基の一つとして有する種々の芳香族アミノ化合物を合成し, これをナフトール染料の顕色剤として利用してモメンを染色し,その色調および堅ろう度をしらべた。すなわち,塩素,臭素,ニトロ,メトキシ,エトキシ,ベンゾイルアミノの各基を一つあるいは二つ有する置換アミノフェニルモルホリン類を合成し,市販ナフトールAS類とモメン上で顕色し染色布について,その反射スペクトルから色度解析を行った結果,臭素基あるいは塩素基のみを有するアミノフェニルモルホリン類は茶色系に,臭素基あるいは塩素基とニトロ基を有するものは赤色に,エトキシ基,メトキシ基を有するものは紫系に,ベンゾイルアミノ基を有するものは紫～ 青色系にそれぞれ顕色することがわかった。臭素基およびニトロ基を有するものの一部をのぞいてはいずれも各種の堅ろう度はすぐれていた。

ピリジン環に活性メチル基を有する2-メチル-5-(5-メチルベンズオキサゾリル-(2))-ピリジン(MBP)と種々の置換基を持ったべンズアルデヒドおよびヘテロ環アルデヒドを無水酢酸中で縮合せしめ1 1 種の4 - ( 5 - メチルベンズオキサゾリル-(2))-スチルベン(A)のアザ同構体を合成した。また上記MBPを二酸化セレンで酸化し5-(5-メチルベンズオキサリゾリル-(2))-2-ピリジンアルデヒドとし, これを活性メチル基を有する2-メチル-5-エチルピリジンと縮合し同型の誘導体(12)を得た。これら誘導体のジオキサン溶液における吸収およびケイ光スペクトルの極大波長はAに比べて,一般に長波長側に移り, そのケイ光相対強度は吸光度が同程度であるにもかかわらず小さい。とくにサリチルアルデヒド, フルフラール,チオフェンアルデヒドからの誘導体のようにオキサゾール環の2-位に結合したピリジン環に対して電子供給性基を有する誘導体は深色移動ならびに強度の減少がいちじるしい。これらの化合物で各種合成繊維を染色した結果, カシミロンF上では黄色に着色しその増白効果は劣るが,一般にピリジン環に対して電子吸引的に働く置換基を有するものが良好であった。増白布をカーボンアーク灯退色試験機中で照射して布のケイ光強度の減少を測定することにより耐光堅ロウ性を試験した。増白結果とあわせてアミランに対しベンズアルデヒドおよび4-カルボキシベンズアルデヒドとの誘導体が, またテトロンに対してベンズアルデヒドおよび4-シアノベンズアルデヒドとの誘導体ならびに12がすぐれた結果を示す。

A. o-Anisidine diazotized is coupled with 2-naphthol, 3-hydroxy-2-naphthanilide, acetoacetanilide, or 1-phenyl-3-methyl-5-pyrazolone, to obtain azo-dyes. Each of the azo-dyes is chloromethylated in acetic acid solution by paraformaldehyde and dry hydrogen chloride gas in the presence of zinc chloride anhydride as a catalyst to obtain chloromethyl compounds.B. 2-Methoxy-5-hydroxymethylaniline synthesized by using o-nitroanisole as a starting material, is diazotized, it is coupled, with 2-naphthol, 3-hydroxy-2-naphthoanilide, acetoacetanilide, or 1-phenyl-3-methyl-5-pyrazolone, to obtain diazo-compounds. Each of the diazo-compounds is chlorinated in chlorobenzene solution by phosphorus pentachloride for conversion of the hydroxymethyl group into the chloromethyl group obtaining chloromethyl compounds.C. We confirmed that the chloromethyl compounds obtained by the method A and each of the corresponding compounds obtained by the method B are identical. We also succeeded to ccnfirm the positions of chloromethyl group obtained by the method A.

塩基性基を有するナフタル酸イミド型ケイ光増白染料として,4-位にジエチルアミノおよびN-ピペリジル-アセチルアミノ基を有する誘導体,および4-アセチルアミノナフタル酸イミドのイミド成分に塩基性置換基を有するアミノ化合物を用いた誘導体を合成した。これらの化合物は溶液中で可視部に吸収を示さず460mμ 付近にケイ光の極大を示す。これら誘導体はカシミロンFに対して主としてイオン交換的に染着する。また4-位のアセチルアミノ基をジェチルアミノアセチルアミノ基に代えることによって加水分解に対する安定性の増すことを確かめた。種々の合成繊維(ビェロンアセテート, アミランおよびカシミロンF)に対する増白効果および耐光堅ロウ性を試験した。4-ジエチルアミノアセチルアミノナフタル酸-n-ブチルイミドおよびシクロヘキシルイミドをジメチル硫酸によって四級化した誘導体はカシミロンFに対してすぐれた増白効果を示し,その耐光性は良好であった。

ビニルスルホン基を有する染料を合成し,繊維と化学的に結合せしめ,堅ろう度良好な染色物をうるために,-p-およびm-アミノフエニルビニルスルホンをジアゾ成分としβ-オキシエチル基を有するアミン類をカップリング成分とする二,三の分散染料を合成し,ビニロン,アミラン,アセテートを染色せしめた。またこのアミンをナフトールベースとして用い,市販ナフトールAS類とともに常法によりモメン,ビニロン上で,さらにビニロン,アミラン,アセテートを一浴法により顕色した。これらの染色物を弱アルカリ性で処理すると大部分の染料は繊維と結合するようである。たとえばモメン染色物を煮沸100%ピリジン液で抽出を試みてもほとんど抽出されず,抽出前後の布についての測色値の検討からも,このことが確かめられた。期待されたようにモメンはナフトール染料で,ビニロン,アミラン,アセテートは分散染料によって,鮮明,かつ堅ろうな染色物が得られた。

The absorption isotherms of four disperse dyes for polypropylene fibers were determined at various temperatures. The affinity, heat of dyeing and entropy of dyeing were calculated from the thermodynamical treatment. The heasts of all four dyes investigated were all negative, so the binding process was exothermic. The affinity of the dye for polypropylene was found to increase with the increase in the hydrophobic character of the dye. The increase in the hydrophobic character of the dye, however, causes the decrease in the heat and entropy of dyeing. This result shows that the higher affinity of the hydrophobic dye comes from the decrease in the entropy of dyeing. From a consideration of the thermodynamical data, it is assumed that the breakdown of so called “iceberg” water structure in the vicinity of the hydrophobic dye takes place in the course of the binding process. The interaction between polypropylene fibre and disperse dye is explained by using the following concept that the binding process involves two main effects: (1) an exothermic interaction (may be dispersion force) (2) an entropic interaction (the formation of a so called. “hydrophobic bond”)

分散アゾ染料の光退色の反応機構に関連して, オキシアゾベンゼンとフェニルアゾピラゾロン誘導体の光退色挙動をナイロンとポリエステルフィルム上において検討した。そしてこれらアゾ染料の光退色速度におよぼす置換基の効果を調べた。オキシアゾベンゼン誘導体ではこれら光退色の容易さは水酸基の置換位置と数に依存し, その退色速度は 2,4-ジオキシアゾ>>2-オキシアゾ>4-オキシアゾの順位となる。また, フェニルアゾピラゾロン系染料においてポリエステル上の光退色相対速度定数の対数値と第1成分のフェニル核内の置換基の Hammett 定数との間には負の勾配をもつ良好な直線関係がえられる。そしてエトロ基を有する染料では両系列ともナイロン上においてみられる異常退色挙動はエトロ基の光還元反応に帰因し, 還元されたアミノ基がその退色を著るしく加速するものと思われる。これらの事実と以前の結果からアゾ染料の光退色反応はアゾ結合のアゾキシ結合への光酸化, 光 Wallach 転位による o-オキシアゾ誘導体の生成およびヒドラゾン互変異性体の光加水分解を経て進むと考えるのが妥当なようである。