Hydroxybenzophenone

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Jan Szymanowski - One of the best experts on this subject based on the ideXlab platform.

Jerzy Zakrzewski - One of the best experts on this subject based on the ideXlab platform.

Hiroyuki Nakazawa - One of the best experts on this subject based on the ideXlab platform.

Norman S. Allen - One of the best experts on this subject based on the ideXlab platform.

  • Interactions in the thermal and light stabilising action of novel aromatic phosphites with a 2-Hydroxybenzophenone and hindered piperidine stabiliser in polyolefin films
    Polymer Degradation and Stability, 1995
    Co-Authors: Norman S. Allen, Ricardo Acosta Ortiz, Graeme J. Anderson
    Abstract:

    Abstract The interactions of two novel phosphite stabilisers with a commercial polymeric hindered piperidine stabiliser, Chimassorb 944, and a 2-hydroxy-4-n-ctoxybenzophenone stabiliser, Cyasorb UV 531, have been examined in the thermal and photooxidation of polypropylene and high density polyethylene films using FTIR spectroscopy. The two structures are based on a bis-hindered phenolic moiety coupled to a 2-Hydroxybenzophenone and a 4-amino-tetramethylpiperidine (3) chromophore. Thermal oven ageing and photooxidation of the polyolefin films showed that the hindered piperidine phosphite (phosphoramide) is synergistic over a wide concentration ratio with both commercial stabilisers. The only exception is in polyethylene with the Chimassorb 944, wherein the latter shows poor solubility in polyethylene. Generally, the phosphoramide is found to be more effective as a thermal antioxidant than as a UV antioxidant. The 2-Hydroxybenzophenone phosphite was generally ineffective as a light stabiliser and exhibited unusual S-shaped profiles in combination with both the commercial stabilisers, suggesting the involvement of two distinct processes. With Cyasorb UV 531 the antagonistic/synergistic patterns were reversed from polypropylene to polyethylene. With Chimassorb 944 strong synergism is observed at high phosphite ratios while antagonism is prevalent at low ratios. In general, one interesting feature of the results is that the thermal and UV effects often exhibit a similar behaviour.

  • Comparison of the thermal and light stabilising action of novel aromatic phosphites substituted with 2-Hydroxybenzophenone and hindered piperidine moieties in polyolefins
    Polymer Degradation and Stability, 1994
    Co-Authors: Norman S. Allen, Ricardo Acosta Ortiz, Graeme J. Anderson, Manji Sasaki
    Abstract:

    Abstract Three novel phosphite stabilisers have been synthesised and characterised and their thermal and photochemical effectiveness examined in polyethylene and polypropylene films. Two structures are based on a bis-hindered phenolic moiety coupled to a 2-Hydroxybenzophenone (2) and a 4-amino-tetramethylpiperidine (3) chromophore. The third is a tris-2-Hydroxybenzophenone based phosphite (4). Thermal oven aging and thermal analysis on the polymer films showed that the hindered piperidine phosphite is an effective primary and secondary antioxidant compared with the 2-Hydroxybenzophenone derivatives. These results are consistent with its ability to inhibit the formation of hydroperoxides during thermal aging. The 4-aminopiperidine phosphite compound is also an effective light stabiliser for polypropylene. The 2-Hydroxybenzophenone derivative (2) was ineffective as a light stabiliser in all cases and antagonised the effectiveness of a commercial polymeric hindered piperidine stabiliser (Chimassorb 944). The tris-2-Hydroxybenzophenone phosphite compound (4), however, was more effective as a light stabiliser in polypropylene than in polyethylene. Both mass spectrometry and thermal analysis indicated initial fragmentation resulting in the loss of the 2-Hydroxybenzophenone and 4-aminopiperidine stabiliser moieties from the phosphorus atom. the importance of combining different stabiliser moieties within the same structure in terms of performance is discussed.

  • Thermal and photooxidative behaviour of novel 4-substituted alicyclic amino-2-Hydroxybenzophenone stabilizers in polypropylene and high density polyethylene films
    Polymer Degradation and Stability, 1992
    Co-Authors: Norman S. Allen, Michele Edge, S. Conway, D.a. Doyle, E.m. Howells, K. Kikkawa, M. Minagawa, T. Sekiguichi
    Abstract:

    The thermal and photooxidative stabilization activities of four light stabilizers based on 2-Hydroxybenzophenone with alicyclic amine groups substituted in the 4-position have been examined and compared with those of 2-hydroxy-4-n-octoxybenzophenone (HOBZ) in polypropylene and high density polyethylene (HDPE) films at 0·1% w/w concentration infra-red absorption spectroscopy. From both carbonyl index and embrittlement times, both alkylpiperazine derivatives were found to be ineffective on exposure to QUV irradiation, whereas the propoxymorpholinyl and the hindered piperidine compounds were found to be more effective than HOBZ. All the stabilizers were synergistic with the commercial hindered phenolic antioxidant, Irganox 1010, especially the HOBZ. On the thermal ageing all the light stabilizers behaved as antioxidants, including the HOBZ. However, the hindered piperidine derivative was the most effective, exhibiting a stabilizing effect close to that of the Irganox 1010. In the presence of the Irganox 1010 weak antagonism was observed, with the HOBZ exhibiting the most effective stabilization. In HDPE the effects were different on irradiation, with all the 4-substituted amino benzophenones being effective. In this case the 4-amino hindered piperidine stabilizer was more effective than HOBZ. In the presence of Irganox 1010 strong synergism is common except for the bis-N,N-octylpiperazine derivative. On oven ageing all the stabilizers exhibited antioxidant behaviour with the 4-amino-piperidine derivative being the most effective. The antioxidant effect of Irganox 1010 was not impaired in HDPE apart from that with the propoxy-morpholino derivative. The steric hindrance, molecular size and oxygen scavenging ability of the cyclic amine are all concluded to be important factors in controlling the antioxidant behaviour of the stabilizer with hydroperoxides playing a key role in the latter case. The results also demonstrate the importance of the ortho hydrogen bonded hydroxyl group in 2-Hydroxybenzophenones as an active chain-breaking donor in photostabilization and not UV absorption. It is further concluded that the results show the potential for the development of a single stabilizer entity which will behave as an effective photothermal antioxidant.

  • Synthesis and thermal and photo-oxidative behaviour of novel 4-substituted alicyclic amino-2-Hydroxybenzophenone stabilizers in polypropylene films
    European Polymer Journal, 1991
    Co-Authors: Norman S. Allen, Michele Edge, S. Conway, D.a. Doyle, E.m. Howells, K. Kikkawa, M. Minagawa, T. Sekiguichi
    Abstract:

    Abstract Four light stabilizers have been synthesized and characterized, based on the substitution of an alicyclic amine group into the 4-position of 2-Hydroxybenzophenone. The compounds prepared were bis-N,N′-alkylpiperazines, N-propoxymorpholinyl and 4-amino-2,2,6,6-tetramethylpiperidinyl derivatives. The thermal and photo-oxidative stabilization activities of the three compounds have been examined and compared with those of 2-hydroxy-4-n-octoxybenzophenone (HOBZ) in polypropylene film at 0.1% w/w concentration using i.r. absorption spectroscopy, hydroperoxide analysis and yellowness index. Through both carbonyl index and embrittlement times, both alkylpiperazine derivatives were found to be ineffective on exposure to QUV irradiation but both the propoxymorpholinyl and the hindered piperidine compounds were found to be more effective than HOBZ. These stabilizing effects followed closely their ability to inhibit hydroperoxide formation before and during oven ageing. With the commercial hindered phenolic antioxidant, Irganox 1010, all the stabilizers were synergistic, especially HOBZ. On thermal ageing, all the light stabilizers including HOBZ behaved as antioxidants. The hindered piperidine derivative was the most effective, exhibiting a stabilizing effect close to that of the Irganox 1010. In the presence of Irganox 1010, weak antagonism was observed with HOBZ exhibiting the most effective stabilization. Both piperazine derivatives discoloured markedly on irradiation while the alkylmorpholinyl exhibited an initial photobleaching effect. The steric hindrance, molecular size and oxidizability of the cyclic amine are all concluded to be important factors in controlling the antioxidant behaviour of the stabilizer, with hydroperoxides playing a key role in the latter case. The results also demonstrate the importance of the ortho hydrogen bonded hydroxy group in 2-Hydroxybenzophenones as an active chain-breaking donor and not the extinction coefficients. It is further concluded that the results show the potential for the development of a single stabilizer entity which will behave as an effective photothermal antioxidant.

Mark E Light - One of the best experts on this subject based on the ideXlab platform.