JPS6139341B2 - - Google Patents
Info
- Publication number
- JPS6139341B2 JPS6139341B2 JP6630677A JP6630677A JPS6139341B2 JP S6139341 B2 JPS6139341 B2 JP S6139341B2 JP 6630677 A JP6630677 A JP 6630677A JP 6630677 A JP6630677 A JP 6630677A JP S6139341 B2 JPS6139341 B2 JP S6139341B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pentene
- carbon atoms
- poly
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 12
- -1 triazole compound Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- 229910052802 copper Inorganic materials 0.000 description 12
- 239000010949 copper Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 7
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- USCSRAJGJYMJFZ-UHFFFAOYSA-N 3-methyl-1-butyne Chemical compound CC(C)C#C USCSRAJGJYMJFZ-UHFFFAOYSA-N 0.000 description 1
- NJIDLJRHMJCJIV-UHFFFAOYSA-N C.C(CC)(=O)O Chemical compound C.C(CC)(=O)O NJIDLJRHMJCJIV-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- 241000156978 Erebia Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- AAQUCXJJDQZZOJ-UHFFFAOYSA-N bis(2-ethylhexyl) phenyl phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OC1=CC=CC=C1 AAQUCXJJDQZZOJ-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940088516 cipro Drugs 0.000 description 1
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000000615 nonconductor Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- VCAFTIGPOYBOIC-UHFFFAOYSA-N phenyl dihydrogen phosphite Chemical compound OP(O)OC1=CC=CC=C1 VCAFTIGPOYBOIC-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- MEFOHEIWDBDKLR-UHFFFAOYSA-N tris[2-(2,4,4-trimethylpentan-2-yl)phenyl] phosphite Chemical compound CC(C)(C)CC(C)(C)C1=CC=CC=C1OP(OC=1C(=CC=CC=1)C(C)(C)CC(C)(C)C)OC1=CC=CC=C1C(C)(C)CC(C)(C)C MEFOHEIWDBDKLR-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Organic Insulating Materials (AREA)
Description
本発明は、酸化安定性の優れたポリ−４−メチ
ル−１−ペンテン組成物に関する。さらに詳しく
は、銅の接触的劣化に対する抵抗力の高められた
ポリ−４−メチル−１−ペンテン組成物に関す
る。
ポリ−４−メチル−１−ペンテンは、融点が高
く、耐薬品性、電気特性が優れているため、高温
又は高温になる可能性のある部位に使用される電
線・ケーブルの被覆用樹脂として注目される。こ
の用途に使用されるには、単なる耐熱性が良好で
あるのみならず、銅の接触による劣化に対しても
充分大きな抵抗力を有していなければならない。
従来、ポリオレフインの銅害防止処方に関して
数多くの提案がなされているが、その多くは専ら
ポリエチレンやポリプロピレンに関するものであ
つて、それらに有効な処方であつてもポリ−４−
メチル−１−ペンテンに適用してみると、必ずし
も実際に使用しうる水準に達しているとは言い難
かつた。
本発明は、とくにポリ−４−メチル−１−ペン
テンに適した銅害防止処方を提供するものであつ
て、その要旨は、ポリ−４−メチル−１−ペンテ
ンに
(A) 式
（上式において、Ｘは水素または炭素数１ない
し18のアルキル基、Ｒは炭素数１ないし18のア
ルキル基、水酸基、ハロゲンを示す。０≦ｎ≦
３、ｎ個のＲは同一でも異なるものでもよい）
で示されるトリアゾール化合物
および
（上式において、R1は炭素数１ないし12のアル
キル基、R2は水素または炭素数１ないし12の
アルキル基、R3は水素、炭素数２ないし18の
アルカノイル基、または
The present invention relates to a poly-4-methyl-1-pentene composition with excellent oxidative stability. More particularly, the present invention relates to poly-4-methyl-1-pentene compositions with increased resistance to catalytic degradation of copper. Poly-4-methyl-1-pentene has a high melting point, excellent chemical resistance, and electrical properties, so it is attracting attention as a coating resin for electric wires and cables used in areas that are or may be exposed to high temperatures. be done. In order to be used for this purpose, it must not only have good heat resistance but also a sufficiently high resistance to deterioration due to contact with copper. In the past, many proposals have been made regarding formulations for preventing copper damage in polyolefins, but most of them relate exclusively to polyethylene and polypropylene, and even if formulations are effective for polyolefins, poly-4-
When applied to methyl-1-pentene, it was difficult to say that it had reached a level that could be used in practice. The present invention provides a copper damage prevention formulation particularly suitable for poly-4-methyl-1-pentene. (In the above formula, X represents hydrogen or an alkyl group having 1 to 18 carbon atoms, and R represents an alkyl group having 1 to 18 carbon atoms, a hydroxyl group, or a halogen. 0≦n≦
3. n R's may be the same or different)
Triazole compound represented by and (In the above formula, R 1 is an alkyl group having 1 to 12 carbon atoms, R 2 is hydrogen or an alkyl group having 1 to 12 carbon atoms, R 3 is hydrogen, an alkanoyl group having 2 to 18 carbon atoms, or
【式】
で示される基、０≦ｍ≦５）で示されるヒドラ
ジン化合物から選ばれる少なくとも一種の化合
物
(B) テトラキス〔メチレン−３−（３・５−ジ−
tert−ブチル−４−ヒドロキシフエニル、）プ
ロピオネート〕メタン
および
(C) 亜リン酸化合物
を配合してなるポリ−４−メチル−１−ペンテン
組成物である。
本発明に用いられる前述の化合物（A1）や
（A2）が、ポリプロピレンの銅害防止剤として使
用されうることは公知である。一般にはA1又は
A2のみの使用は充分な効果をあげることができ
ないので、チオジアルカン酸エステルのような含
硫黄化合物との併用が推奨されている。ところが
ポリ−４−メチル−１−ペンテンの場合において
は、このような併用処方でも銅害に対する安定化
効果は充分とは言えずその改良が望まれていた。
そこで本発明者らは化合物（A1）および（A2）を
基にしたポリ−４−メチル−１−ペンテンの銅害
防止処方につき鋭意研究した結果、本発明に到達
したものである。
本発明においてポリ−４−メチル−１−ペンテ
ンは、４−メチル−１−ペンテンの単独重合体の
みならず、４−メチル−１−ペンテンと少割合の
他のα−オレフイン、例えばエチレン、プロピレ
ン、１−ブテン、３−メチル−１−ブチン、３−
メチル−１−ペンテン、１−ヘキセン、１−オク
テン、１−デセン、１−ウンデセン、１−ヘキサ
デセン、１−オクタデセンなどのランダム共重合
体あるいはブロツク共重合体であつてもよい。さ
らに上述の重合体に他の熱可塑性樹脂たとえばポ
リオレフインやゴムたとえばオレフイン共重合ゴ
ムが配合されたものであつてもよい。
式（A1）で表わされる化合物の代表例を示す
と、At least one compound selected from the group represented by [Formula] and hydrazine compounds represented by 0≦m≦5) (B) Tetrakis [methylene-3-(3,5-di-
This is a poly-4-methyl-1-pentene composition containing tert-butyl-4-hydroxyphenyl, (propionate) methane, and (C) a phosphorous acid compound. It is known that the aforementioned compounds (A 1 ) and (A 2 ) used in the present invention can be used as copper damage inhibitors for polypropylene. Generally A 1 or
Since the use of A 2 alone cannot produce sufficient effects, it is recommended to use it in combination with a sulfur-containing compound such as a thiodialkanoic acid ester. However, in the case of poly-4-methyl-1-pentene, even with such a combination formulation, the stabilizing effect against copper damage was not sufficient, and an improvement was desired.
Therefore, the present inventors conducted intensive research on a copper-damage prevention formulation of poly-4-methyl-1-pentene based on compounds (A 1 ) and (A 2 ), and as a result, they arrived at the present invention. In the present invention, poly-4-methyl-1-pentene is not only a homopolymer of 4-methyl-1-pentene, but also 4-methyl-1-pentene and a small proportion of other α-olefins, such as ethylene and propylene. , 1-butene, 3-methyl-1-butyne, 3-
It may be a random copolymer or block copolymer of methyl-1-pentene, 1-hexene, 1-octene, 1-decene, 1-undecene, 1-hexadecene, 1-octadecene and the like. Furthermore, other thermoplastic resins such as polyolefins and rubbers such as olefin copolymer rubbers may be blended with the above-mentioned polymers. Typical examples of compounds represented by formula (A 1 ) are:
【式】【formula】
【式】【formula】
【式】【formula】
【式】【formula】
【式】などを挙げるこ
とができる。
式（A2）で表わされる化合物の代表例として
は、
などを例示することができる。
本発明の(c)成分として用いる亜リン酸化合物と
しては、トリアルキルホスフアイト、トリアリー
ルホスフアイト、多価アルコールの亜リン酸エス
テルなどの亜リン酸エステルを例示することがで
きる。具体的には、トリフエニルホスフアイト、
トリクレジルホスフアイト、トリデシルホスフア
イト、トリオクタデシルホスフアイト、トリ
（tert−オクチルフエニル）ホスフアイト、トリ
（tert−ノニルフエニル）ホスフアイト、フエニ
ル・ジ（２−エチルヘキシル）ホスフアイト、ト
リ〔４・4′−ｎ−ブチリデンビス（２−tert−ブ
チル−５−メチルフエノール）〕ホスフアイトな
どを挙げることができる。
本発明においては(A)(B)(C)の３種配合が必須であ
り、かかる複合配合の相乗作用により、顕著な銅
害防止効果が得られる。配合量は、ポリ−４−メ
チル−１−ペンテン10.0重量部に対し、通常(A)成
分0.05ないし１重量部、(B)成分0.05ないし１重量
部、(C)成分0.05ないし１重量部、好ましくは(A)成
分0.1ないし0.5重量部、(B)成分0.1ないし0.5重量
部、(C)成分0.1ないし0.5重量部程度である。この
他必要に応じ、金属石けん、酸化防止剤、紫外線
吸収剤、帯電防止剤、顔料、充填剤、防曇剤、多
価アルコールなどが配合されていてもよい。
本発明の組成物は、銅の存在下においても安定
性が良好であるので、電線、電気絶縁物などの用
途に使用することができる。
次に実施例を示す。
比較例 １
ポリ−４−メチル−１−ペンテン 100 部
ジラウリルチオジプロピオネート 0.5 部
テトラキス〔メチレン−３−（３・５−ジ−
tert−ブチル−４−ヒドロキシフエニル）プロ
ピオネート〕メタン 0.25部
比較例 ２
ポリ−４−メチル−１−ペンテン 100 部
ペンタエリスリチルテトラ−β−メルカプトラ
ウリルプロピオネート（Seenox412Sシプロ化
成社製） 0.5 部
テトラキス〔メチレン−３−（３・５−ジ−
tert−ブチル−４−ヒドロキシフエニル）プロ
ピオネート〕メタン 0.25部
比較例 ３
ポリ−４−メチル−１−ペンテン 100 部
ペンタエリスリチルテトラ−β−メルカプトラ
ウリルプロピオネート 0.5 部
テトラキス〔メチレン−３−（３・５−ジ−
tert−ブチル−４ヒドロキシフエニル）プロピ
オネート〕メタン 0.25部
0.5 部
実施例 １
ポリ−４−メチル−１−ペンテン 100 部
トリスノニルフエニルフオスフアイト
（Mark329、アデカアーガスス社製） 0.5 部
テトラキス〔メチレン−３−（３・５−ジ−
tert−ブチル−４−ヒドロキシフエニル）プロ
ピオネート〕メタン 0.25部Examples include [Formula]. Representative examples of compounds represented by formula (A 2 ) include: For example, Examples of the phosphorous acid compound used as component (c) of the present invention include phosphorous esters such as trialkyl phosphites, triarylphosphites, and phosphorous esters of polyhydric alcohols. Specifically, triphenyl phosphite,
Tricresyl phosphite, tridecyl phosphite, triotadecyl phosphite, tri(tert-octylphenyl) phosphite, tri(tert-nonylphenyl) phosphite, phenyl di(2-ethylhexyl) phosphite, tri[4.4' -n-butylidene bis(2-tert-butyl-5-methylphenol)] phosphite and the like. In the present invention, the combination of three types (A), (B), and (C) is essential, and the synergistic effect of such a composite combination provides a remarkable effect of preventing copper damage. The blending amount is usually 0.05 to 1 part by weight of component (A), 0.05 to 1 part by weight of component (B), 0.05 to 1 part by weight of component (C), to 10.0 parts by weight of poly-4-methyl-1-pentene. Preferably, the amount of component (A) is about 0.1 to 0.5 parts by weight, the component (B) is about 0.1 to 0.5 parts by weight, and the component (C) is about 0.1 to 0.5 parts by weight. In addition, metal soaps, antioxidants, ultraviolet absorbers, antistatic agents, pigments, fillers, antifogging agents, polyhydric alcohols, and the like may be blended as necessary. Since the composition of the present invention has good stability even in the presence of copper, it can be used for applications such as electric wires and electrical insulators. Next, examples will be shown. Comparative Example 1 Poly-4-methyl-1-pentene 100 parts dilaurylthiodipropionate 0.5 part Tetrakis [methylene-3-(3,5-di-
tert-Butyl-4-hydroxyphenyl) propionate] methane 0.25 parts Comparative example 2 Poly-4-methyl-1-pentene 100 parts Pentaerythrityl tetra-β-mercaptrauryl propionate (Seenox 412S manufactured by Cipro Kasei Co., Ltd.) 0.5 parts Tetrakis [methylene-3-(3,5-di-
tert-butyl-4-hydroxyphenyl) propionate] methane 0.25 parts Comparative Example 3 Poly-4-methyl-1-pentene 100 parts Pentaerythrityl tetra-β-mercaptrauryl propionate 0.5 parts Tetrakis [methylene-3-( 3・5-G-
tert-butyl-4-hydroxyphenyl)propionate methane 0.25 parts 0.5 parts Example 1 Poly-4-methyl-1-pentene 100 parts Trisnonyl phenyl phosphorite (Mark 329, manufactured by Adeka Argus) 0.5 parts Tetrakis [methylene-3-(3,5-di-
tert-butyl-4-hydroxyphenyl)propionate]methane 0.25 parts
【式】 0.5 部 実施例 ２[Formula] 0.5 part Example 2
【表】
上記配合物をヘンシエルミキサーで混合した
後、20mmφ押出機にてペレタイズしさらに0.5mm
のプレスシートに成形し、その耐熱老化性を180
℃ギヤオープン中でテストし、茶褐色に変色する
までの時間を調べた。又同様にして作つた0.3mm
プレスシートの間に銅板をはさんで、再プレス
し、150℃ギヤオーブン中でその耐銅害性をクラ
ツクが発生するまでの時間をみることにより評価
した。結果を表１に示す。
比較例２、３は耐熱老化時間を改良した優れた
処方であるが銅害防止性はほとんどみられない。
しかし実施例１、２に示す処方では銅害防止性が
飛躍的に伸びていることがわかる。[Table] After mixing the above compound with a Henschel mixer, pelletize it with a 20 mmφ extruder and further add 0.5 mm.
molded into a press sheet with heat aging resistance of 180
A test was conducted with the gear open, and the time required for the color to change to brown was determined. Another 0.3mm made in the same way
A copper plate was sandwiched between the press sheets and pressed again, and the copper damage resistance was evaluated by observing the time until cracks appeared in a gear oven at 150°C. The results are shown in Table 1. Comparative Examples 2 and 3 are excellent formulations with improved heat aging time, but almost no copper damage prevention properties are observed.
However, it can be seen that the formulations shown in Examples 1 and 2 have dramatically increased copper damage prevention properties.
【表】【table】
Claims (1)
し18のアルキル基、Ｒは炭素数１ないし18のア
ルキル基、水酸基、ハロゲンを示す、０≦ｎ≦
３、ｎ個のＲは同一でも異なるものでもよい）
で示されるトリアゾール化合物および （上式において、R1は炭素数１ないし12のアル
キル基、R2は水素または炭素数１ないし12の
アルキル基、R3は水素、炭素数２ないし18の
アルカノイル基、または 【式】 で示される基、ｍは０ないし５）で示されるヒ
ドラジン化合物から選ばれる少なくとも一種の
化合物、 (B) テトラキス〔メチレン−３−（３・５−ジ−
tert−ブチル−４−ヒドロキシフエニル）プロ
ピオネート〕メタン および (C) 亜リン酸化合物 を配合してなるポリ−４−メチル−１−ペンテン
組成物。[Claims] 1 Poly-4-methyl-1-pentene with the formula (A) (In the above formula, X represents hydrogen or an alkyl group having 1 to 18 carbon atoms, R represents an alkyl group having 1 to 18 carbon atoms, a hydroxyl group, or a halogen, 0≦n≦
3. n R's may be the same or different)
A triazole compound represented by and (In the above formula, R 1 is an alkyl group having 1 to 12 carbon atoms, R 2 is hydrogen or an alkyl group having 1 to 12 carbon atoms, R 3 is hydrogen, an alkanoyl group having 2 to 18 carbon atoms, or [Formula] (B) at least one compound selected from hydrazine compounds represented by the group shown above, m is 0 to 5), (B) tetrakis[methylene-3-(3,5-di-
A poly-4-methyl-1-pentene composition comprising tert-butyl-4-hydroxyphenyl)propionate]methane and (C) a phosphorous acid compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6630677A JPS541359A (en) | 1977-06-07 | 1977-06-07 | Poly-4-methyl-1-pentene composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6630677A JPS541359A (en) | 1977-06-07 | 1977-06-07 | Poly-4-methyl-1-pentene composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS541359A JPS541359A (en) | 1979-01-08 |
| JPS6139341B2 true JPS6139341B2 (en) | 1986-09-03 |
Family
ID=13311986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6630677A Granted JPS541359A (en) | 1977-06-07 | 1977-06-07 | Poly-4-methyl-1-pentene composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS541359A (en) |
-
1977
- 1977-06-07 JP JP6630677A patent/JPS541359A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS541359A (en) | 1979-01-08 |
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