DABCO effect on the photodegradation of photochromic compounds in spiro[indoline-pyran] and spiro[indoline-oxazine] series

Salemi, Christiane; Giusti, G.; Guglielmetti, R.

doi:10.1016/1010-6030(94)03926-l

Cited by 53 publications

(28 citation statements)

References 11 publications

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“…The photochromic nylon fabric deteriorated with exposure to the Xenotest in a similar way to the dyed polyester, although there remained some residual observable photochromism after 60‐h exposure. It has been reported that DABCO, a singlet oxygen quencher, can significantly increase the fatigue resistance of photochromic compounds [11]. In an attempt to promote the photostability of photochromic nylon, DABCO was used during the dyeing of nylon with the spirooxazines.…”

Section: Resultsmentioning

confidence: 99%

Direct coloration of textiles with photochromic dyes. Part 1: Application of spiroindolinonaphthoxazines as disperse dyes to polyester, nylon and acrylic fabrics^†

Billah

Christie

Shamey

2008

Coloration Technology

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1,3,3‐Trimethylspiroindoline‐2,3′‐3H‐naphth[2,1‐b][1,4]oxazine (1a) and 6′‐piperidino‐1,3,3‐trimethylspiroindoline‐2,3′‐3H‐naphth[2,1‐b][1,4]oxazine (1b) were applied as disperse dyes to polyester, nylon and acrylic fabrics. Under optimised dyeing conditions, photochromic fabrics were produced which, on irradiation with ultraviolet or exposure to sunlight, turned blue (1a) or blueish‐purple (1b). Dye 1a showed enhanced photochromic colour change performance compared with dye 1b. The photochromic colour build was highest on nylon and lowest on acrylic fabric. The colour change properties and the technical performance (wash fastness and photostability) of the photochromic fabrics were evaluated using specifically adapted colour measurement methods. The data were analysed in terms of variation of lightness, a*, b*, chroma, hue angle and ΔE, colour difference before and after exposure, and K/S curves as a function of irradiation time. The fabrics generally showed good wash fastness. Although the colour build‐up decreased with exposure to the Xenotest fadeometer, some residual photochromism remained after prolonged exposure.

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Section: Resultsmentioning

confidence: 99%

Direct coloration of textiles with photochromic dyes. Part 1: Application of spiroindolinonaphthoxazines as disperse dyes to polyester, nylon and acrylic fabrics^†

Billah

Christie

Shamey

2008

Coloration Technology

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“…Another limiting factor regarding the industrial application of spiropyran/spirooxazine photochromic compounds is the fatigue phenomenon after long-term use. Spiropyran derivatives exhibit worse fatigue resistance than spirooxazine derivatives [79][80][81][82]. The fatigue resistance of spiropyran/spirooxazine derivatives can be improved by adding appropriate antioxidants or hindered amine light stabilizers or UV stabilizers [83,84]; introducing antioxidant group into spiropyran/spirooxazine molecule structure [84,85]; or other methods [86].…”

Section: Fatigue Resistancementioning

confidence: 99%

Preparation and analysis of photochromic behavior of carboxymethyl chitin derivatives containing spiropyran moieties

Sun

Yao

et al. 2020

Designed Monomers and Polymers

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1ʹ-(2-Acryloxyethyl)-3,3ʹ-dimethyl-6-nitrospiro[2 H-1-benzopyran-2,2ʹ-indoline] (SPA) was synthesized and grafted onto a water-soluble carboxymethyl chitin (CMCH) macromolecule to prepare a photochromic copolymer (CMCH-g-SPA). The structure of CMCH-g-SPA was characterized by Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric (TG) analysis, X-ray diffraction (XRD) analysis, water-solubility evaluation, and UV-vis spectroscopy. XRD patterns of CMCH-g-SPA revealed that grafting copolymerization disrupts the CMCH semicrystalline structure, thus improving water solubility. UV-vis spectroscopy results supported the negative photochromic behavior of the merocyanine (MC) form of CMCH-g-SPA (CMCH-g-MCA) present in a water solution of the target copolymer. In addition to high solvent polarity, the intermolecular and intramolecular electrostatic attraction between the indolenine cation and the COO − anion were found to be influencing factors, which stabilize these MC form of spiropyran groups grafted onto CMCH. In a water solution, visible light bleaching was completed over a short period (8 minutes) under artificial visible light irradiation and the thermal coloration reaction, whose rate constant at 25 °C was 4.64 × 10 −4 s −1 , which fit the first-order reaction equation. After ten photochromic cycles in water solution, the relative absorption intensity of CMCH-g-MCA decreased by 7.92%.

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“…long-lived triplet state. 51 There are conflicting reports about whether the generation of singlet oxygen via this triplet state is responsible for photodegradation, 51,61,62 with perhaps more than one mechanism present. Although our experiments were performed under a nitrogen environment, we cannot rule out oxygen being trapped in the films during their preparation.…”

Section: P1 + P3 Pmma Filmmentioning

confidence: 99%

Photochrome-doped organic films for photonic keypad locks and multi-state fluorescence

Ritchie

Vamvounis

Soleimaninejad

et al. 2017

Phys. Chem. Chem. Phys.

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The spectroscopic properties of poly(methyl methacrylate) polymer films doped with two kinds of photochromic molecular switches are investigated. A green-fluorescent sulfonyl diarylethene (P1) is combined with either a non-fluorescent diarylethene (P2) or red-fluorescent spiropyran (P3). Photoswitching between the colorless and colored isomers (P1: o-BTFO4 ↔ c-BTFO4, P2: o-DTE ↔ c-DTE, P3: SP ↔ MC) enables the P1 + P2 and P1 + P3 films to be cycled through three distinct states. From the initial state (o-BTFO4 + o-DTE/SP), irradiation with UV light generates the second state (c-BTFO4 + c-DTE/MC), where c-BTFO4 → c-DTE/MC energy transfer is established. Irradiation with green light then generates the third state (c-BTFO4 + o-DTE/SP), where the energy transfer acceptor is no longer present. Finally, irradiation with blue light regenerates the initial state. For the P1 + P2 film, only one state is fluorescent, with the irradiation inputs required to be entered in the correct order to access this state, acting as a keypad lock. For the P1 + P3 film, the states emit either no fluorescence, red fluorescence, or green fluorescence, all using a common excitation wavelength. Additionally, once the fluorescence is activated with UV light, it undergoes a time-dependent color transition from red to green, due to the pairing of P-type and T-type photochromes. These multi-photochromic systems may be useful for security ink or imaging applications.

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DABCO effect on the photodegradation of photochromic compounds in spiro[indoline-pyran] and spiro[indoline-oxazine] series

Cited by 53 publications

References 11 publications

Direct coloration of textiles with photochromic dyes. Part 1: Application of spiroindolinonaphthoxazines as disperse dyes to polyester, nylon and acrylic fabrics^†

Direct coloration of textiles with photochromic dyes. Part 1: Application of spiroindolinonaphthoxazines as disperse dyes to polyester, nylon and acrylic fabrics^†

Preparation and analysis of photochromic behavior of carboxymethyl chitin derivatives containing spiropyran moieties

Photochrome-doped organic films for photonic keypad locks and multi-state fluorescence

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DABCO effect on the photodegradation of photochromic compounds in spiro[indoline-pyran] and spiro[indoline-oxazine] series

Cited by 53 publications

References 11 publications

Direct coloration of textiles with photochromic dyes. Part 1: Application of spiroindolinonaphthoxazines as disperse dyes to polyester, nylon and acrylic fabrics†

Direct coloration of textiles with photochromic dyes. Part 1: Application of spiroindolinonaphthoxazines as disperse dyes to polyester, nylon and acrylic fabrics†

Preparation and analysis of photochromic behavior of carboxymethyl chitin derivatives containing spiropyran moieties

Photochrome-doped organic films for photonic keypad locks and multi-state fluorescence

Contact Info

Product

Resources

About

Direct coloration of textiles with photochromic dyes. Part 1: Application of spiroindolinonaphthoxazines as disperse dyes to polyester, nylon and acrylic fabrics^†

Direct coloration of textiles with photochromic dyes. Part 1: Application of spiroindolinonaphthoxazines as disperse dyes to polyester, nylon and acrylic fabrics^†