JPH0461023B2 - - Google Patents
Info
- Publication number
- JPH0461023B2 JPH0461023B2 JP60119257A JP11925785A JPH0461023B2 JP H0461023 B2 JPH0461023 B2 JP H0461023B2 JP 60119257 A JP60119257 A JP 60119257A JP 11925785 A JP11925785 A JP 11925785A JP H0461023 B2 JPH0461023 B2 JP H0461023B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- weight
- crosslinking
- electron beam
- beam irradiation
- 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 - Lifetime
Links
- 229920000098 polyolefin Polymers 0.000 claims description 13
- 238000010894 electron beam technology Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 7
- 150000003751 zinc Chemical class 0.000 claims description 6
- CJKWEXMFQPNNTL-UHFFFAOYSA-N bis(prop-2-enyl) 1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylate Chemical compound C=CCOC(=O)C1C(C(=O)OCC=C)C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl CJKWEXMFQPNNTL-UHFFFAOYSA-N 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 description 16
- 230000032683 aging Effects 0.000 description 14
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 6
- 230000001737 promoting effect Effects 0.000 description 4
- 230000000740 bleeding effect Effects 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical group CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- UDQCDDZBBZNIFA-UHFFFAOYSA-N 4-methyl-1,3-dihydrobenzimidazole-2-thione Chemical compound CC1=CC=CC2=C1NC(=S)N2 UDQCDDZBBZNIFA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SHLNMHIRQGRGOL-UHFFFAOYSA-N barium zinc Chemical compound [Zn].[Ba] SHLNMHIRQGRGOL-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229920000092 linear low density polyethylene Polymers 0.000 description 1
- 239000004707 linear low-density polyethylene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
〔産業上の利用分野〕
この発明は電子線照射架橋ポリオレフイン組成
物に関するものである。
〔従来の技術〕
ポリオレフインは電気的特性、機械的特性等に
優れていることから広範囲にわたつて使用されて
いるが、使用環境によつては耐熱変形性、機械的
特性、耐薬品性等の向上がさらに要求されること
があり、そのために通常架橋が行なわれている。
このような架橋方法の一つに電子線照射法があ
り、特に機器内配線等の細物の絶縁電線のように
薄い被覆材料に対しては水素蒸気架橋法等に比較
して非常に効率が良いことから、少なくともこの
ような分野においては主として電子線照射法が採
用されている。
一般にポリオレフインを高温雰囲気下で使用す
るためには、架橋によつて耐熱変形性を向上させ
ると同時に、耐熱老化特性をも改善することが肝
要であることから、従来、電子線照射に供される
樹脂に対して架橋効率を上げるための架橋促進剤
と熱老化防止剤とが配合されて来た。その架橋促
進剤にはたとえばトリメチルロールプロパントリ
メタクリレート（以下、TMPTと略称する）、ま
た熱老化防止剤には４，4′−チオ−ビス（６−ｔ
−ブチル−ｍ−クレゾール）（以下、フエノール
系老化防と略称する）が使用されている。
〔発明が解決しようとする問題点〕
しかし、従来のこのような電子線照射架橋ポリ
オレフイン組成物には次のような問題点があつ
た。すなわち、
TMPTの架橋促進効果があまり大きくない。
フエノール系老防がTMPTの架橋促進効果
を一層低下させる。
TMPTの親和性が悪くブリード現象（にじ
み出し現象）生じやすい。
である。
〔問題点を解決するための手段〕
上記の問題点を解決するために、この発明はポ
リオレフイン樹脂100重量部にジアリルクロレン
デート0.5〜５重量部および２−メルカブトベン
ゾイミダゾールの亜鉛塩または２−メルカブト−
メチル−ベンゾイミダゾールの亜鉛塩２−30重量
部を配合した組成物とする手段を採用したのであ
る。
〔実施例〕
この発明でいうポリオレフインとは、たとえば
C2〜C8のオレフインモノマーの１種または２種
以上の重合体、C2〜C8のジエンモノマーの重合
体、エチレン酢酸ビニル共重合体、エチレンエチ
ルアクリレート共重合体およびこれらの混合物を
いう。
また、この発明でいうジアリルクロレンデート
は、電子線照射時に、ポリマー鎖からの脱水素反
応を促進し、架橋反応を促す作用を有するもので
次の化学構造式で表わされる。
なお、ｎは１〜４程度のものが使用に供される
が、好ましくは１又は２のものである。このジア
リルクロレンデートは液体でポリオレフインには
きわめて親和性があつてよく分散する。そしてこ
の発明においては、ポリオレフイン100重量部に
対して、ジアリルクロレンデートの添加量を0.5
〜５重量部とすることが望ましい。なぜならば、
添加量が0.5重量部未満では、架橋促進効果が認
められず、逆に５重量部を越える場合には、架橋
促進効果の向上がないばかりでなく、ブリード現
象が生じ、商品価値を著しく低下させるからであ
る。
つぎにこの発明における熱老化防止剤として
は、前記の架橋促進剤を使用するうえで、２−メ
ルカプトベンゾイミダゾールの亜鉛塩
または２−メルカプト−メチル−ベンゾイミダ
ゾールの亜鉛塩
があげられ、これらの化合物は空気中における電
子線照射時の酸素によるポリオレフインの老化を
防ぎ、しかも架橋反応を阻害することなく、ブリ
ード現象もなく、耐熱老化特性にきわめて顕著な
効果を表わす。そしてこのような熱老化防止剤の
配合量はポリオレフイン100重量部に対して２〜
30重量部とすることが望ましい。なぜならば熱老
化防止剤が２重量部未満の少量では耐熱性の向上
に不充分であり、逆に、30重量部を越える場合に
は、増量による効果が期待できないばかりでな
く、機械的特性の低下が著しくなつて好ましくな
いからである。
いま、つぎの基準配合、すなわち
（重量部）
(1) 線状低密度ポリエチレン（日本ユニカ社製：
GS−650） ……80部
(2) エチレン−エチルアクリレート共重合体（同
社製：DPDJ−6182）
……20部に難燃剤および難燃助剤として、
(3) デカブロモジフエニルエーテル（三井フアイ
ンケミカル社製：プラネロンDB−102）
……50部
(4) 三酸化アンチモン
……20部さらに加工助剤として
(5) 亜鉛華 ……５部
(6) ステアリン酸亜鉛 ……２部
(7) バリウム−亜鉛系安定剤 ……３部
に第１表に示す割合で架橋促進剤および熱老化防
止剤を配合した（実施例１〜10）。これら各例の
諸原料はミキシングロールによつて150〜180℃に
加熱混練した後、ゲージ圧150Kg／cm2、180℃10分
間の条件でプレス成形し、0.5mm厚のシートを作
製し、加速電圧750keV、44mAの条件下、得ら
れたシートに対し空気中で電子線照射を行なつ
た。この際の電子線照射量はいずれも20Mradで
あり、その電子線照射後におけるシートの引張り
強さ（Kg／mm2）および伸び（％）を測定した。な
お、電子線照射後のシートについては特にUL規
格の125℃定格評価法に準じて158℃の空気熱老化
試験機中に７日間保持した熱老化試験後の引張り
強さおよび伸びとをこの熱老化試験前の値に対す
る残率（％）の形で求め、電子線照射後のゲル分
率（％）、ブリード現象の有無（”あり”を×
印、”なし”を○印で示す）などとともにえられ
た結果を第１表にまとめて併記した。ポリオレフ
インを架橋したものは架橋度が増すにつれゲル分
率は増加し、それと共に加熱変形性が減少すると
いう関係があり、第１表中のゲル分率（％）はキ
シレン溶液に120℃で24時間浸漬した後、120℃で
24時間乾燥し、
ゲル分率（％）＝乾燥後の重量／浸漬前の重量×100
によつて求めた。また同表中「TMPT」は前記
したとおりトリメチロールプロパントリメタクリ
レートである。
[Industrial Application Field] This invention relates to an electron beam irradiation crosslinked polyolefin composition. [Prior Art] Polyolefins are widely used due to their excellent electrical and mechanical properties. However, depending on the usage environment, their heat deformation resistance, mechanical properties, chemical resistance, etc. Further improvements may be required and crosslinking is usually carried out for this purpose.
One such crosslinking method is electron beam irradiation, which is much more efficient than hydrogen vapor crosslinking, especially for thin coating materials such as thin insulated wires used in equipment wiring. Because of its advantages, electron beam irradiation is mainly used, at least in this field. In general, in order to use polyolefins in high-temperature environments, it is important to improve their heat deformation resistance through crosslinking and at the same time improve their heat aging resistance. Crosslinking accelerators and heat aging inhibitors have been added to resins to increase crosslinking efficiency. The crosslinking accelerator is, for example, trimethylolpropane trimethacrylate (hereinafter abbreviated as TMPT), and the heat aging inhibitor is 4,4'-thio-bis(6-t
-butyl-m-cresol) (hereinafter abbreviated as phenolic anti-aging agent) is used. [Problems to be Solved by the Invention] However, such conventional electron beam irradiation crosslinked polyolefin compositions have the following problems. In other words, the crosslinking promoting effect of TMPT is not very large. Phenolic anti-aging agents further reduce the crosslinking promoting effect of TMPT. TMPT has poor affinity and tends to cause bleed phenomenon. It is. [Means for Solving the Problems] In order to solve the above problems, the present invention adds 0.5 to 5 parts by weight of diallyl chlorendate and a zinc salt of 2-mercabutobenzimidazole or 2-mercabutobenzimidazole to 100 parts by weight of a polyolefin resin. -Merkabuto-
They adopted a method of creating a composition containing 2-30 parts by weight of zinc salt of methyl-benzimidazole. [Example] The polyolefin referred to in this invention is, for example,
Refers to one or more polymers of C2 to C8 olefin monomers, polymers of C2 to C8 diene monomers, ethylene vinyl acetate copolymers, ethylene ethyl acrylate copolymers, and mixtures thereof. . Further, the diallyl chlorendate referred to in this invention has the effect of promoting dehydrogenation reaction from polymer chains and promoting crosslinking reaction during electron beam irradiation, and is represented by the following chemical structural formula. Note that n may be about 1 to 4, but preferably 1 or 2. This diallylchlorendate is a liquid and has an extremely high affinity for polyolefins and is well dispersed. In this invention, the amount of diallylchlorendate added is 0.5 parts by weight per 100 parts by weight of polyolefin.
It is desirable to set it as 5 parts by weight. because,
If the amount added is less than 0.5 parts by weight, no crosslinking promotion effect will be observed, and if it exceeds 5 parts by weight, not only will there be no improvement in the crosslinking promotion effect, but a bleeding phenomenon will occur, significantly reducing the commercial value. It is from. Next, as the heat aging inhibitor in this invention, when using the above-mentioned crosslinking accelerator, zinc salt of 2-mercaptobenzimidazole is used. or zinc salt of 2-mercapto-methyl-benzimidazole These compounds prevent the aging of polyolefins due to oxygen during electron beam irradiation in the air, do not inhibit the crosslinking reaction, do not cause any bleeding phenomenon, and exhibit extremely remarkable effects on heat aging resistance. The amount of such heat aging inhibitor added is 2 to 100 parts by weight of polyolefin.
The amount is preferably 30 parts by weight. This is because if the amount of heat aging inhibitor is less than 2 parts by weight, it is insufficient to improve heat resistance, and conversely, if it exceeds 30 parts by weight, not only can no effect be expected from increasing the amount, but also the mechanical properties may deteriorate. This is because the decrease becomes significant, which is undesirable. Now, the following standard composition, i.e. (parts by weight) (1) Linear low-density polyethylene (manufactured by Nippon Unica Co., Ltd.: GS-650) ...80 parts (2) Ethylene-ethyl acrylate copolymer (manufactured by the same company: DPDJ- 6182)
...20 parts as a flame retardant and flame retardant aid, (3) Decabromodiphenyl ether (Mitsui Fine Chemicals: Planelon DB-102)
...50 parts (4) Antimony trioxide
...20 parts and as a processing aid (5) Zinc white ...5 parts (6) Zinc stearate ...2 parts (7) Barium-zinc stabilizer ...3 parts cross-linked in the ratio shown in Table 1. Accelerators and heat aging inhibitors were formulated (Examples 1-10). The raw materials in each of these examples were heated and kneaded at 150 to 180°C using a mixing roll, then press-formed under the conditions of a gauge pressure of 150 kg/cm 2 and 180°C for 10 minutes to produce a 0.5 mm thick sheet. The obtained sheet was irradiated with an electron beam in air at a voltage of 750 keV and 44 mA. The amount of electron beam irradiation at this time was 20 Mrad in each case, and the tensile strength (Kg/mm 2 ) and elongation (%) of the sheet after the electron beam irradiation were measured. In addition, for sheets after electron beam irradiation, the tensile strength and elongation after a heat aging test held in an air heat aging tester at 158°C for 7 days in accordance with the UL standard's 125°C rating evaluation method are calculated based on the heat aging test. It is determined in the form of the residual rate (%) of the value before the aging test, and the gel fraction (%) after electron beam irradiation and the presence or absence of bleeding phenomenon (“Yes” is
The results obtained are summarized and listed in Table 1. In crosslinked polyolefins, as the degree of crosslinking increases, the gel fraction increases, and the heat deformability decreases. After soaking for an hour, at 120℃
It was dried for 24 hours and determined by gel fraction (%) = weight after drying/weight before immersion x 100. In addition, "TMPT" in the same table is trimethylolpropane trimethacrylate as described above.
【表】【table】
以上述べたように、この発明によつて、すぐれ
た架橋促進効果、引張り強さや伸び等の機械的性
質、耐熱老化特性および耐ブリード性などの諸点
で、従来見られなかつた良い結果を示す電子線照
射ポリオレフイン組成物が得られた。
As described above, the present invention has enabled electronics to exhibit previously unseen good results in terms of excellent crosslinking promotion effects, mechanical properties such as tensile strength and elongation, heat aging resistance, and bleed resistance. A radiation-irradiated polyolefin composition was obtained.
【表】【table】
【表】【table】
Claims (1)
ンデート0.5〜５重量部および２−メルカブトベ
ンゾイミダゾールの亜鉛塩または２−メルカブト
−メチル−ベンゾイミダゾールの亜鉛塩を２〜30
重量部配合したことを特徴とする電子線照射架橋
ポリオレフイン組成物。1 Add 0.5 to 5 parts by weight of diallylchlorendate and 2 to 30 parts by weight of a zinc salt of 2-mercabutobenzimidazole or a zinc salt of 2-mercabuto-methyl-benzimidazole to 100 parts by weight of a polyolefin.
An electron beam irradiation crosslinked polyolefin composition characterized in that it contains parts by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11925785A JPS61276838A (en) | 1985-05-31 | 1985-05-31 | Polyolefin composition crosslinked by electron ray irradiation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11925785A JPS61276838A (en) | 1985-05-31 | 1985-05-31 | Polyolefin composition crosslinked by electron ray irradiation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61276838A JPS61276838A (en) | 1986-12-06 |
| JPH0461023B2 true JPH0461023B2 (en) | 1992-09-29 |
Family
ID=14756850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11925785A Granted JPS61276838A (en) | 1985-05-31 | 1985-05-31 | Polyolefin composition crosslinked by electron ray irradiation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61276838A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57143A (en) * | 1980-05-31 | 1982-01-05 | Dainichi Nippon Cables Ltd | Polyethylene composition for high-expansion extrusion |
| JPS57197155A (en) * | 1981-05-11 | 1982-12-03 | Goodyear Tire & Rubber | Rubber composite material reinforced by metal |
| JPS61228043A (en) * | 1985-03-30 | 1986-10-11 | Tatsuta Electric Wire & Cable Co Ltd | Polyolefin composition crosslinked by irradiation with electron rays |
-
1985
- 1985-05-31 JP JP11925785A patent/JPS61276838A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57143A (en) * | 1980-05-31 | 1982-01-05 | Dainichi Nippon Cables Ltd | Polyethylene composition for high-expansion extrusion |
| JPS57197155A (en) * | 1981-05-11 | 1982-12-03 | Goodyear Tire & Rubber | Rubber composite material reinforced by metal |
| JPS61228043A (en) * | 1985-03-30 | 1986-10-11 | Tatsuta Electric Wire & Cable Co Ltd | Polyolefin composition crosslinked by irradiation with electron rays |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61276838A (en) | 1986-12-06 |
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