JPH0517691A - Stabilized organic polymer composition - Google Patents
Stabilized organic polymer compositionInfo
- Publication number
- JPH0517691A JPH0517691A JP19360691A JP19360691A JPH0517691A JP H0517691 A JPH0517691 A JP H0517691A JP 19360691 A JP19360691 A JP 19360691A JP 19360691 A JP19360691 A JP 19360691A JP H0517691 A JPH0517691 A JP H0517691A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- organic polymer
- polymer composition
- phenolic compound
- Prior art date
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- Pending
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は非汚染性有機高分子組成
物に関するものであり、更に詳しくは式（１）BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a non-polluting organic polymer composition, and more particularly to formula (1)
【０００２】[0002]
【化３】
〔式（１）で、Ｒ1 及びＲ2 は同一又は相異なって、ハ
ロゲン原子、アルキル基、シクロアルキル基、アリール
基、アラルキル基又はアルケニル基を表わし、ｍ及びｎ
は０又は１〜４の整数を表わす。〕で示される環状有機
りん化合物と、式（２）[Chemical 3] [In the formula (1), R 1 and R 2 are the same or different and represent a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or an alkenyl group, and m and n
Represents 0 or an integer of 1 to 4. ] And a cyclic organophosphorus compound represented by the formula (2)
【０００３】[0003]
【化４】
〔式（２）で、Ｒは同一又は相異なって、ハロゲン原
子、アルキル基、シクロアルキル基、アリール基、ヒド
ロキシアリール基、ヒドロキシアルキルアリール基、ア
ルコキシ基、アリロキシ基、アラルキル基、ヒドロキシ
アラルキル基、ヒドロキシアルキルアラルキル基又はア
ルケニル基を表わし、ｍ′は０又は１〜５、ｎ′は１〜
２の整数を表わす。〕で示されるフェノール系化合物と
を含有せしめた汚染性の改良された安定化有機高分子組
成物に関する。[Chemical 4] [In the formula (2), R is the same or different and is a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, a hydroxyaryl group, a hydroxyalkylaryl group, an alkoxy group, an allyloxy group, an aralkyl group, a hydroxyaralkyl group, Represents a hydroxyalkylaralkyl group or an alkenyl group, m'is 0 or 1 to 5, n'is 1 to
Represents an integer of 2. ] The present invention relates to a stabilized organic polymer composition containing a phenolic compound represented by the following formula and having improved stain resistance.
【０００４】[0004]
【従来の技術】従来、有機高分子物質、特に合成又は半
合成樹脂にはその用途に応じて各種安定剤が添加され、
多くの場合、各安定剤の補完的組合せによりその効果を
発揮するような提案がなされ、又実施されている。2. Description of the Related Art Conventionally, various stabilizers have been added to organic polymer substances, particularly synthetic or semi-synthetic resins, depending on the use.
In many cases, it has been proposed and implemented that its effect is exhibited by the complementary combination of each stabilizer.
【０００５】式（１）で示される環状有機りん化合物に
ついても、特公昭４８−４１００９号、特公昭５１−４
７１７３号、特公昭６１−３６８５１号各公報等でその
安定剤としての有用性が提案され、実用化されている。The cyclic organic phosphorus compound represented by the formula (1) is also disclosed in Japanese Patent Publication Nos. 48-41009 and 51-4.
7173, JP-B-61-36851 and the like, their usefulness as stabilizers have been proposed and put to practical use.
【０００６】特に有機高分子物質の加工時に於ける劣化
に基因する汚染の防止効果は非常に優れており、各種有
機高分子物質に適用されている。In particular, the effect of preventing contamination due to deterioration during processing of organic polymer substances is very excellent, and it is applied to various organic polymer substances.
【０００７】[0007]
【発明が解決しようとする課題】しかしながら、加工時
の効果に比し、加工されたものの経時変化（貯蔵あるい
は使用環境）に於ける汚染の防止効果は不充分な場合が
多々あり、その改善が要望されていた。However, in many cases, the effect of preventing the contamination of the processed product over time (storage or use environment) is insufficient as compared with the effect at the time of processing. It was requested.
【０００８】[0008]
【課題を解決するための手段】本発明者らは、上記改善
を達成すべく鋭意検討を重ねた結果、式（１）で示され
る環状有機りん化合物と式（２）て示されるフェノール
系化合物とを組合せて有機高分子物質に添加することに
より、その加工時に於ける汚染の防止効果と、加工した
ものの経時の汚染の防止効果が共に優れた有機高分子組
成物が得られることを見出すに到り、本発明を完成し
た。Means for Solving the Problems As a result of intensive studies to achieve the above improvement, the present inventors have found that the cyclic organophosphorus compound represented by the formula (1) and the phenolic compound represented by the formula (2). It was found that an organic polymer composition excellent in both the effect of preventing contamination at the time of processing and the effect of preventing contamination over time of the processed product can be obtained by adding a combination of and to an organic polymer substance. At this point, the present invention has been completed.
【０００９】上記式（１）の環状有機りん化合物の具体
例は、９，１０−ジヒドロ−９−オキサ−１０−ホスフ
ァフェナンスレン−１０−オキサイド（以下ＨＣＡ；三
光化学株式会社商品名）、（以下ジフェニル骨核上の置
換基のみ記す。）、１−クロル（又はブロム、フルオ
ル）、１，３−ジクロル（又はジブロム、ジフルオ
ル）、１，３，７−トリクロル（又はトリブロム、トリ
フルオル）、１−メチル、１，３−ジメチル、１，３，
７−トリメチル、１−ターシャリーブチル、３−ターシ
ャリーブチル、１−シクロヘキシル、３−（α−メチル
ベンジル、１−フェニル、３−フェニル、１−（４−メ
チルフェニル）、３−シアノ、１−メチル−３−クロル
（又はブロム）、１−メチル−３，７−ジクロル（又は
ジブロム）、１，３，７−トリメチル−２，６−ジクロ
ル（又はジブロム）、１−フェニル−３−クロル（又は
ブロム）、１−クロル（又はブロム）−３−ベンジル、
１−クロル−３−ブロム、１，３−ジブロム−７−クロ
ル、などが挙げられる。Specific examples of the cyclic organophosphorus compound of the above formula (1) include 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (hereinafter referred to as HCA; Sanko Chemical Co., Ltd. trade name). , (Hereinafter, only the substituents on the diphenyl bone nucleus are described), 1-chloro (or bromo, fluoro), 1,3-dichloro (or dibromo, difluor), 1,3,7-trichloro (or tribromo, trifluoro). , 1-methyl, 1,3-dimethyl, 1,3
7-trimethyl, 1-tert-butyl, 3-tert-butyl, 1-cyclohexyl, 3- (α-methylbenzyl, 1-phenyl, 3-phenyl, 1- (4-methylphenyl), 3-cyano, 1 -Methyl-3-chloro (or bromo), 1-methyl-3,7-dichloro (or dibromo), 1,3,7-trimethyl-2,6-dichloro (or dibromo), 1-phenyl-3-chloro (Or bromo), 1-chloro (or bromo) -3-benzyl,
1-chloro-3-bromo, 1,3-dibromo-7-chloro, and the like.
【００１０】上記式（２）のフェノール系化合物の具体
例は、カテコール、（以下フェニル骨核の置換基のみ記
す。）３−アルキル（Ｃ1 〜Ｃ18）、４−アルキル（Ｃ
1 〜Ｃ18）、３−フェニル、４−フェニル、３，４−ジ
アルキル（Ｃ1 〜Ｃ18）、３，５−ジアルキル（Ｃ1 〜
Ｃ18）、３，６−ジアルキル（Ｃ1 〜Ｃ18）、３−クロ
ル（又はブロム）、４−クロル（又はブロム）、３，４
−ジクロル（又はジブロム）、３，５−ジクロル（ジブ
ロム）、３，６−ジクロル（又はジブロム）など、ハイ
ドロキノン、（以下フェニル骨核の置換基のみを記
す。）、２−アルキル（Ｃ1 〜Ｃ18）、２，５−ジアル
キル（Ｃ1 〜Ｃ18）、２−フェニル、２，５−ジフェニ
ル、２−クロル（又はブロム）、２，５−ジクロル（又
はジブロム）など、レゾルシン（以下フェニル骨核の置
換基のみ記す。）、２−アルキル（Ｃ1 〜Ｃ18）、４−
アルキル（Ｃ1 〜Ｃ18）、２，４−ジアルキル（Ｃ1 〜
Ｃ18）、４，６−ジアルキル（Ｃ1 〜Ｃ18）、２−クロ
ル（又はブロム）、４−クロル（又はブロム）、２，４
−ジクロル（又はジブロム）、４，６−ジクロル（又は
ジブロム）など、４，４′−ジヒドロキシジフェニル、
（以下ジフェニル骨核の置換基のみ記す）、２−アルキ
ル（Ｃ1 〜Ｃ18）、３−アルキル（Ｃ1 〜Ｃ18）、２，
２′−ジアルキル（Ｃ1 〜Ｃ18）、３，３′−ジアルキ
ル（Ｃ1 〜Ｃ18）、２，３′−ジアルキル（Ｃ1 〜
Ｃ18）、２−フェニル、３−フェニルなど、が挙げられ
る。Specific examples of the phenolic compound of the above formula (2) include catechol, (only the substituents of the phenyl bone nucleus are described below) 3-alkyl (C 1 -C 18 ), 4-alkyl (C).
1 -C 18), 3- phenyl, 4-phenyl, 3,4-dialkyl (C 1 ~C 18), 3,5- dialkyl (C 1 ~
C 18), 3,6-dialkyl (C 1 -C 18), 3- chloro (or bromo), 4-chlorophenyl (or bromine), 3,4
-Dichloro (or dibromo), 3,5-dichloro (dibromo), 3,6-dichloro (or dibromo), etc., hydroquinone, (hereinafter, only the substituents of the phenyl bone nucleus are described), 2-alkyl (C 1- ). C 18 ), 2,5-dialkyl (C 1 -C 18 ), 2-phenyl, 2,5-diphenyl, 2-chloro (or bromo), 2,5-dichloro (or dibromo), etc., resorcin (hereinafter phenyl). Only the substituents of the bone nucleus are shown), 2-alkyl (C 1 -C 18 ), 4-
Alkyl (C 1 ~C 18), 2,4- dialkyl (C 1 ~
C 18), 4,6-dialkyl (C 1 -C 18), 2-chloro (or bromo), 4-chlorophenyl (or bromine), 2,4
-Dichloro (or dibromo), 4,6-dichloro (or dibromo), etc., 4,4'-dihydroxydiphenyl,
(Hereinafter, only the substituents of the diphenyl bone nucleus will be described), 2-alkyl (C 1 -C 18 ), 3-alkyl (C 1 -C 18 ), 2,
2'-dialkyl (C 1 ~C 18), 3,3'- di (C 1 ~C 18), 2,3'- di (C 1 ~
C 18 ), 2-phenyl, 3-phenyl and the like.
【００１１】有機高分子物質としては天然、半合成、合
成高分子物質、特にポリエチレン、ポリプロピレン、ポ
リブタジエン、ポリスチレン、ポリビニルクロライド、
ポリアクリルニトリル、ポリアミド、ポリビニルアルコ
ール、ポリイミド、ポリカーボネート、ポリフェニレン
オキシド、ポリウレタン、ポリフェニレンスルフィド、
ポリエーテルサルホン、エポキシ樹脂、フェノール樹
脂、ポリエステル、不飽和ポリエステルなどが挙げられ
る。Organic high molecular substances include natural, semi-synthetic and synthetic high molecular substances, especially polyethylene, polypropylene, polybutadiene, polystyrene, polyvinyl chloride,
Polyacrylonitrile, polyamide, polyvinyl alcohol, polyimide, polycarbonate, polyphenylene oxide, polyurethane, polyphenylene sulfide,
Examples thereof include polyether sulfone, epoxy resin, phenol resin, polyester, unsaturated polyester and the like.
【００１２】[0012]
【作用】式（１）の環状有機りん化合物と式（２）のフ
ェノール系化合物との組合せ（以下本安定剤という）の
添加量はそれらの合計量として、被安定化物質１００部
（重量部以下同じ）当り０．００５〜１０部、好ましく
は０．０１〜２部程度である。The amount of the combination of the cyclic organophosphorus compound of the formula (1) and the phenolic compound of the formula (2) (hereinafter referred to as the present stabilizer) is 100 parts by weight of the substance to be stabilized (part by weight). The same shall apply hereinafter) is 0.005 to 10 parts, preferably 0.01 to 2 parts.
【００１３】式（１）で示される環状有機りん化合物と
式（２）で示されるフェノール系化合物との割合は、モ
ル比で前者１：後者０．１〜２であり、好ましくは１．
０：０．２〜０．５である。The molar ratio of the cyclic organophosphorus compound represented by the formula (1) to the phenolic compound represented by the formula (2) is the former 1: the latter 0.1 to 2, preferably 1.
0: 0.2 to 0.5.
【００１４】これら本安定剤の有機高分子物質への添加
方法については特に制限はないが、２種（又はそれ以
上）の化合物をあらかじめ溶融混合して添加するのが便
利であり好ましい。The method of adding these stabilizers to the organic polymer substance is not particularly limited, but it is convenient and preferable to melt-mix and add two (or more) compounds in advance.
【００１５】本発明の安定剤以外の安定剤（例えばフェ
ノール系酸化防止剤、ホスファイト類、硫黄系安定剤、
紫外線吸収剤、紫外線安定剤など）や染料、顔料、充填
剤、可塑剤等の配合も勿論可能である。Stabilizers other than the stabilizer of the present invention (for example, phenolic antioxidants, phosphites, sulfur stabilizers,
Of course, it is also possible to mix (UV absorber, UV stabilizer, etc.), dye, pigment, filler, plasticizer and the like.
【００１６】[0016]
【実施例】次に本発明を更に具体的に説明するために実
施例を述べるが、これに限定されるものではない。EXAMPLES Examples will now be described in order to more specifically describe the present invention, but the present invention is not limited thereto.
【００１７】実施例１
ＡＢＳ樹脂（デンカＧＲ２０００）１００部と、４−タ
ーシャリブチルカテコールとＨＣＡとの混合物（モル比
０．３：１．０で前もって溶融混合したもの）０．３６
７部を取り、１５５℃の温度で６分間ロールで混練した
後、プレス成形（２００℃、４分間）して１ｍｍ厚の板
を作り、１２０℃ギヤーオーブン中で強制劣化させ変色
の程度を色差測定により判定した。その結果を表１に示
す。Example 1 100 parts of ABS resin (Denka GR2000), a mixture of 4-tertiarybutylcatechol and HCA (previously melt mixed in a molar ratio of 0.3: 1.0) 0.36
After taking 7 parts, kneading with a roll at a temperature of 155 ° C for 6 minutes, press molding (200 ° C, 4 minutes) to make a 1 mm thick plate, and forcibly deteriorating in a gear oven at 120 ° C to determine the degree of discoloration. It was judged by measurement. The results are shown in Table 1.
【００１８】[0018]
【表１】
実施例２
実施例１の４−ターシャリーブチルカテコールをハイド
ロキノンに替え、添加量を０．３４５部とした以外は実
施例１と同じく処理し、表２に示す結果を得た。[Table 1] Example 2 4-tertiary butyl catechol of Example 1 was replaced with hydroquinone, and the same treatment as in Example 1 was carried out except that the addition amount was 0.345 parts, and the results shown in Table 2 were obtained.
【００１９】[0019]
【表２】
実施例３
実施例１の４−ターシャリーブチルカテコールを２−メ
チル−ハイドロキノンに替え、添加量を０．３５１部と
した以外は実施例１と同じく処理し、表３に示す結果を
得た。[Table 2] Example 3 The same treatment as in Example 1 was carried out except that 4-tert-butylcatechol of Example 1 was replaced with 2-methyl-hydroquinone and the addition amount was 0.351 parts, and the results shown in Table 3 were obtained.
【００２０】[0020]
【表３】
比較例１
ＡＢＳ樹脂（デンカＧＲ−２０００）１００部を取り、
１５５℃の温度で６分間ロールで混練した後、プレス成
形（２００℃、４分間）して１ｍｍ厚の板を作り、１２
０℃ギヤーオーブン中で強制劣化させ変色の程度を色差
測定により判定した。その結果を表４に示す。[Table 3] Comparative Example 1 Take 100 parts of ABS resin (Denka GR-2000),
After kneading with a roll at a temperature of 155 ° C. for 6 minutes, press molding (200 ° C., 4 minutes) to make a 1 mm thick plate.
It was forcibly deteriorated in a 0 ° C gear oven and the degree of discoloration was judged by color difference measurement. The results are shown in Table 4.
【００２１】[0021]
【表４】
比較例２
比較例１のロール混練時にＨＣＡ０．３部を添加した以
外は比較例１と同じく処理した。その結果を表５に示
す。[Table 4] Comparative Example 2 The same treatment as in Comparative Example 1 was performed except that 0.3 part of HCA was added during roll kneading in Comparative Example 1. The results are shown in Table 5.
【００２２】[0022]
【表５】 [Table 5]
【００２３】[0023]
【発明の効果】以上説明した通り、有機高分子物質に式
（１）で示される環状有機りん化合物と式（２）で示さ
れるフェノール系化合物とを含有せしめることにより、
その加工時及び経時に於ける有機高分子物質の劣化に基
因する汚染を著しく改善することが可能になった。Industrial Applicability As described above, by incorporating the cyclic organic phosphorus compound represented by the formula (1) and the phenolic compound represented by the formula (2) into the organic polymer,
It has become possible to remarkably improve the pollution caused by the deterioration of the organic polymer material during the processing and the passage of time.
Claims (5)
ロゲン原子、アルキル基、シクロアルキル基、アリール
基、アラルキル基又はアルケニル基を表わし、ｍ及びｎ
は０又は１〜４の整数を表わす。〕で示される環状有機
りん化合物と、式（２） 【化２】 〔式（２）で、Ｒは同一又は相異なって、ハロゲン原
子、アルキル基、シクロアルキル基、アリール基、ヒド
ロキシアリール基、ヒドロキシアルキルアリール基、ア
ルコキシ基、アリロキシ基、アラルキル基、ヒドロキシ
アラルキル基、ヒドロキシアルキルアラルキル基又はア
ルケニル基を表わし、ｍ′は０又は１〜５、ｎ′は１〜
２の整数を表わす。〕で示されるフェノール系化合物と
を含有せしめた汚染性の改良された安定化有機高分子組
成物。1. Formula (1): [In the formula (1), R 1 and R 2 are the same or different and represent a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or an alkenyl group, and m and n
Represents 0 or an integer of 1 to 4. ] And a cyclic organophosphorus compound represented by the formula (2) [In the formula (2), R is the same or different and is a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, a hydroxyaryl group, a hydroxyalkylaryl group, an alkoxy group, an allyloxy group, an aralkyl group, a hydroxyaralkyl group, Represents a hydroxyalkylaralkyl group or an alkenyl group, m'is 0 or 1 to 5, n'is 1 to
Represents an integer of 2. ] A stabilized organic polymer composition containing a phenolic compound represented by the following formula and having improved stain resistance.
０−ジヒドロ−９−オキサ−１０−ホスファフェナンス
レン−１０−オキサイドである安定化有機高分子組成
物。2. The cyclic organophosphorus compound according to claim 1 is 9,1.
A stabilized organic polymer composition which is 0-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide.
ーシャリーブチルカテコールである安定化有機高分子組
成物。3. A stabilized organic polymer composition in which the phenolic compound of claim 1 is 4-tert-butylcatechol.
ロキノンである安定化有機高分子組成物。4. A stabilized organic polymer composition in which the phenolic compound of claim 1 is hydroquinone.
４′−ジヒドロキシジフェニルである安定化高分子組成
物。5. The phenolic compound according to claim 1 is 4,
A stabilized polymeric composition which is 4'-dihydroxydiphenyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19360691A JPH0517691A (en) | 1991-07-09 | 1991-07-09 | Stabilized organic polymer composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19360691A JPH0517691A (en) | 1991-07-09 | 1991-07-09 | Stabilized organic polymer composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0517691A true JPH0517691A (en) | 1993-01-26 |
Family
ID=16310746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19360691A Pending JPH0517691A (en) | 1991-07-09 | 1991-07-09 | Stabilized organic polymer composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0517691A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5804621A (en) * | 1995-11-27 | 1998-09-08 | Sumitomo Chemical Company, Limited | Polymeric composition |
| EP1016688A3 (en) * | 1998-12-22 | 2001-09-05 | Mitsubishi Gas Chemical Company, Inc. | Aromatic polycarbonate composition |
| JP2011202107A (en) * | 2010-03-26 | 2011-10-13 | Nippon Steel Chem Co Ltd | Phosphorus-containing phenol resin composition, curable composition including the composition as essential component and cured product |
-
1991
- 1991-07-09 JP JP19360691A patent/JPH0517691A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5804621A (en) * | 1995-11-27 | 1998-09-08 | Sumitomo Chemical Company, Limited | Polymeric composition |
| EP1016688A3 (en) * | 1998-12-22 | 2001-09-05 | Mitsubishi Gas Chemical Company, Inc. | Aromatic polycarbonate composition |
| JP2011202107A (en) * | 2010-03-26 | 2011-10-13 | Nippon Steel Chem Co Ltd | Phosphorus-containing phenol resin composition, curable composition including the composition as essential component and cured product |
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