Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2000-04-14
2002-10-15
Sanders, Kriellion A. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C252S389230, C252S389210, C524S119000, C524S120000, C524S141000, C524S153000, C524S291000
Reexamination Certificate
active
06465548
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a stabilized organic polymer material composition wherein the organic polymer material susceptible to degradation due to oxidation, heat or light has become hardly degraded in qualities, such as physical properties, appearance and the like, even after thermal hysteresis during processing and in use. The present invention also relates to a stabilizer composition for organic polymer material, which is an additive used for obtaining a stabilized organic polymer material composition.
BACKGROUND ART
An organic polymer material comprising organic compounds, such as natural polymer, synthetic polymer, fats and oils, lubricant oil, working oil and the like, is susceptible to degradation by oxidation, heat, light and the like, and loses utility. Therefore, various stabilizers called antioxidants are added to organic polymer materials to give organic polymer material compositions that are not easily degraded.
A compound of the formula
wherein R
1
is alkyl having 1 to 18 carbon atoms or alkenyl having 2 to 18 carbon atoms, R
2
is alkyl having 1 to 5 carbon atoms, R
3
, R
4
and R
5
are the same or different and each is hydrogen atom or alkyl having 1 to 4 carbon atoms, and R
6
is hydrogen atom or alkyl having 1 to 5 carbon atoms, is widely known as an antioxidant for fats and oils and polyolefin.
For example, compounds of the formula (1), wherein R
1
and R
2
are both methyl, are disclosed in JP-B-42-11064, U.S. Pat. No. 3,476,772, Chemical Abstracts, vol. 70, 2500, ibid., vol. 50, 15104 and ibid., vol. 72, 13900, German Patent No. 114916 and JP-A-49-72338, as antioxidants. However, since marked coloring of organic polymer materials containing these 6-hydroxychroman compounds has not been overcome, these 6-hydroxychroman compounds have not been widely used as antioxidants.
Meanwhile, vitamin E (tocopherol), wherein R
1
is alkyl having 16 carbon atoms and R
2
is methyl, is a natural substance and is widely used for the prevention of oxidation of foodstuffs.
In 1940s, a phosphorus compound was studied as an antioxidant and some phosphorus antioxidants have since been used in an extremely broad range.
For example, JP-A-1-254744 discloses tetrakis(2,4-di-tert-butylphenyl)-4,4′-biphenylenediphosphonite.
JP-A-5-178870 discloses tetrakis(2,4-di-tert-butyl-5-methylphenyl)-4,4′-biphenylenediphosphonite and a composition containing this compound.
JP-A-8-231568 discloses (2,4-di-tert-butylphenoxy)bis[4′-[bis(2,4-di-tert-butylphenoxy)phosphino]biphenyl-4-yl]phosphine, (2,4-di-tert-butyl-5-methylphenoxy)bis[4′-[bis(2,4-di-tert-butyl-5-methylphenoxy)phosphino]biphenyl-4-yl]phosphine and the like and the compositions containing these compounds.
JP-A-9-238490 discloses 2,4-di-tert-butylphenyl(biphenyl-4-yl)[4′-bis(2,4-di-tert-butylphenoxy)phosphanylbiphenyl-4-yl]phosphinite, 2,4-di-tert-butyl-5-methylphenyl(biphenyl-4-yl)[4′-bis(2,4-di-tert-butyl-5-methylphenoxy)phosphanylbiphenyl-4-yl]phosphinite and the like and the compositions containing these compounds.
The above-mentioned publications teach that these compounds and the compositions containing these compounds are effective stabilizers for organic polymer materials.
Besides these, aryl phosphite compounds such as tris(2,4-di-tert-butylphenyl)phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, triphenyl phosphite, diphenyl alkyl phosphite, phenyl dialkyl phosphite, tris(nonylphenyl)phosphite, trilauryl phosphite, trioctadecyl phosphite, bis(2,4-di-tert-butyl-6-methylphenyl) methyl phosphite and the like have been used as antioxidants.
In addition, pentaerythritol phosphite compounds such as bis(2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis(2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, distearyl pentaerythritol diphosphite, bis(2,4-di(1-phenyl-1,1-dimethylmethyl)phenyl) pentaerythritol diphosphite, (2,4,6-tri-tert-butylphenyl)-2-butyl-2-ethyl-1,3-propanediol phosphite, bisisodecyloxy pentaerythritol diphosphite, bis(2,4,6-tri-tert-butylphenyl)pentaerythritol diphosphite and the like have been used as antioxidants.
Moreover, bisarylalkyl phosphite (oxaphosphocin) compounds such as 2,2-methylenebis(4,6-di-tert-butylphenyl) 2-ethylhexyl phosphite, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenzo[d,g]-1,3,2-dioxaphosphocin, 2,2′,2″-nitrilo[triethyltris(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite] and the like have been used as phosphorus antioxidants.
In 1930s, a phenolic compound was studied as an antioxidant and some phenolic antioxidants have since been used in an extremely broad range.
For example, generally used phenolic antioxidants are exemplified by n-octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, and 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene and the like.
In addition, plural kinds of antioxidants have been widely used in combination to allow simultaneous expression of different effects or synergistic effect.
For example, JP-A-53-78248 teaches a method for preventing yellowing by the use of a polyolefin composition containing a 6-hydroxychroman compound and a phenolic antioxidant, such as 2,6-di-tert-butyl-4-methylphenol and tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyloxymethyl]methane. In this specification, 0.005-0.5 part by weight, preferably 0.01-0.2 part by weight, of a 6-hydroxychroman compound, and 0.005-1 part by weight, preferably 0.01-0.5 part by weight, of a phenolic antioxidant are added to 100 parts by weight of a resin.
JP-A-54-20056 discloses a thermoplastic polymer having an improved heat stability, which contains a 6-hydroxychroman compound. It is taught that a 6-hydroxychroman compound is added in a proportion of 0.005-0.2 part by weight, preferably 0.01-0.1 part by weight, per 100 parts by weight of a resin. When the content is less than 0.005 part by weight, the heat stabilizing effect is taught to be little.
JP-A-53-114852 teaches that a polyolefin having superior stability can be obtained by adding a 6-hydroxychroman compound and a phenolic antioxidant (e.g., 2,6-di-tert-butyl-4-methylphenol, 2,2-methylenebis(4-ethyl-6-tert-butyl)phenol and the like). This publication teaches the addition of 0.005-0.5 part by weight, preferably 0.01-0.2 part by weight, of a 6-hydroxychroman compound and 0.01-5 parts by weight, preferably 0.05-1.0 part by weight, of a phenolic antioxidant to 100 parts by weight of a resin.
Since a phenolic antioxidant and a phosphorus antioxidant show different actions, a combined use of these has been proposed. A phosphorus compound is used as a secondary antioxidant and a hindered phenol compound is used as a primary antioxidant during the processing of a synthetic resin, thereby to improve coloring of an organic polymer material.
For example, JP-B-4-69657 discloses a polyolefin composition containing a 6-hydroxychroman compound and tetrakis(2,4-di-tert-butylphenyl)-4,4′-biphenylenediphosphite, both in a proportion of 0.01-1 wt%.
JP-A-63-137941 discloses a composition containing vitamin E (0.005-0.5 part by weight, preferably 0.03-0.3 part by weight) and tetrakis(2,4-di-tert-butylphenyl)-4,4′-biphenylenediphosphite (0.005-0.5 part by weight, preferably 0.03-0.3 part by weight) per 100 parts by weight of a resin, as a polyolefin composition superior in heat stability and hue. It also teaches that a vitamin E content of less than 0.005 part by weight per 100 parts by weight of a resin results in improved hue but insufficient heat stabilizing effect during forming processing.
JP-A-62-86036 teaches that addition of a 6-hydroxychroman compound (0.005-0.5 part by weight, preferably 0.01-0.2 part by weight) and a phosphorus antioxidant of distearyl pentaerythritol phosphite or tris(2,4-di-tert-butylphenyl) phosphite (0.01-0.5 part by w
Horie Shoichi
Inoue Takeshi
Sanders Kriellion A.
Wenderoth , Lind & Ponack, L.L.P.
Yoshitomi Fine Chemicals, Ltd.
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