JP2002155171A - Rubber composition - Google Patents
Rubber compositionInfo
- Publication number
- JP2002155171A JP2002155171A JP2001194482A JP2001194482A JP2002155171A JP 2002155171 A JP2002155171 A JP 2002155171A JP 2001194482 A JP2001194482 A JP 2001194482A JP 2001194482 A JP2001194482 A JP 2001194482A JP 2002155171 A JP2002155171 A JP 2002155171A
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- Prior art keywords
- rubber
- plasticizer
- acid
- weight
- ester
- Prior art date
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- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、油性物質に抽出さ
れにくく、且つゴムの耐寒性を向上せしめるゴム用可塑
剤及びそれを含有するゴム組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a plasticizer for rubber which is hardly extracted by an oily substance and improves cold resistance of rubber, and a rubber composition containing the same.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来、
ゴムの耐寒性を向上させる技術として、フタル酸エステ
ル、アジピン酸エステルや、ポリエチレングリコール脂
肪酸エステル等の可塑剤を添加する方法が知られてい
る。しかし、これら従来の可塑剤ではグリース等の油性
物質に接触すると抽出されてしまい、また高温下では揮
発してしまい、当初の耐寒性が損なわれてしまうという
問題がある。さらにポリエステル系可塑剤等は抽出や揮
発が起こりにくいが、本来の耐寒性が劣るという問題も
ある。2. Description of the Related Art
As a technique for improving the cold resistance of rubber, a method of adding a plasticizer such as a phthalic acid ester, an adipic acid ester, or a polyethylene glycol fatty acid ester is known. However, these conventional plasticizers have the problem that they are extracted when they come in contact with oily substances such as grease and volatilized at high temperatures, thus impairing the initial cold resistance. Further, the extraction and volatilization of the polyester plasticizer and the like hardly occur, but there is a problem that the original cold resistance is inferior.
【０００３】これらの問題点を解決する技術が、特開昭
６１−１４５２３６号や特開平７−２９２２３５号に開
示されているが、これらの技術ではクロロプレンゴム系
で−３０℃〜０℃付近の温度でゴムが硬くなるという現
象が見られる。[0003] Techniques for solving these problems are disclosed in JP-A-61-145236 and JP-A-7-292235. In these techniques, a chloroprene rubber system having a temperature of around -30 ° C to 0 ° C is used. There is a phenomenon that the rubber becomes harder at the temperature.
【０００４】本発明の課題は、油性物質と接触しても抽
出されにくく、また高温下でも揮発しにくく、且つゴム
の耐寒性、特にクロロプレンゴム系で−３０℃〜０℃付
近の温度でのゴムの耐寒性を更に向上させることができ
るゴム用可塑剤及びゴム組成物を提供することにある。It is an object of the present invention to provide a rubber composition which is hardly extracted even when it comes into contact with an oily substance, hardly volatilized even at a high temperature, and has low cold resistance of rubber, especially chloroprene rubber at a temperature around -30 ° C to 0 ° C. An object of the present invention is to provide a rubber plasticizer and a rubber composition that can further improve the cold resistance of rubber.
【０００５】[0005]
【課題を解決するための手段】本発明は、数平均分子量
２００〜５０００のポリオキシテトラメチレングリコー
ルと炭素数６〜１６の分岐脂肪酸とのエステルからなる
ゴム用可塑剤、並びにこのゴム用可塑剤を、ゴム１００
重量部に対して３〜５０重量部含有するゴム組成物であ
る。SUMMARY OF THE INVENTION The present invention provides a rubber plasticizer comprising an ester of polyoxytetramethylene glycol having a number average molecular weight of 200 to 5000 and a branched fatty acid having 6 to 16 carbon atoms, and a plasticizer for the rubber. With rubber 100
It is a rubber composition containing 3 to 50 parts by weight with respect to parts by weight.
【０００６】[0006]
【発明の実施の形態】本発明の可塑剤は、水酸基価から
求めた、数平均分子量２００〜５０００のポリオキシテ
トラメチレングリコールと炭素数６〜１６の分岐脂肪酸
とのエステルであり、ジエステルを７５重量％以上含む
ものが好ましい。BEST MODE FOR CARRYING OUT THE INVENTION The plasticizer of the present invention is an ester of polyoxytetramethylene glycol having a number average molecular weight of 200 to 5000 and a branched fatty acid having 6 to 16 carbon atoms, obtained from a hydroxyl value. It is preferable that the content is at least 10 wt%.
【０００７】本発明の可塑剤におけるポリオキシテトラ
メチレングリコールの数平均分子量は、油性物質に対す
る抽出されにくさ、高温下での揮発しにくさ、及び耐寒
性の観点から、２００〜５０００であり、好ましくは３
００〜３０００、更に好ましくは５００〜２０００であ
る。[0007] The number average molecular weight of polyoxytetramethylene glycol in the plasticizer of the present invention is 200 to 5000 from the viewpoints of difficulty in extracting oily substances, difficulty in volatilizing at high temperature, and cold resistance. Preferably 3
It is from 0.00 to 3,000, more preferably from 500 to 2,000.
【０００８】炭素数６〜１６の分岐脂肪酸としては、例
えば、イソヘキサン酸、イソヘプタン酸、２−エチルヘ
キサン酸、イソノナン酸、イソデカン酸、イソトリデカ
ン酸、イソミリスチン酸、イソパルミチン酸等が挙げら
れ、好ましくはイソヘプタン酸、２−エチルヘキサン
酸、イソノナン酸、特に好ましくは２−エチルヘキサン
酸、イソノナン酸である。これらは１種単独でも、２種
以上を併用してもよい。分岐脂肪酸の炭素数が６〜１６
の範囲にあることが、ゴム組成物のブリードなどの問題
が生じないため必須である。Examples of the branched fatty acid having 6 to 16 carbon atoms include isohexanoic acid, isoheptanoic acid, 2-ethylhexanoic acid, isononanoic acid, isodecanoic acid, isotridecanoic acid, isomyristic acid, and isopalmitic acid. Is isoheptanoic acid, 2-ethylhexanoic acid and isononanoic acid, particularly preferably 2-ethylhexanoic acid and isononanoic acid. These may be used alone or in combination of two or more. The branched fatty acid has 6 to 16 carbon atoms
Is essential because problems such as bleeding of the rubber composition do not occur.
【０００９】本発明の可塑剤は、公知の方法、例えばポ
リオキシテトラメチレングリコールと、分岐脂肪酸と、
ジブチルスズオキシド等の金属触媒を高温下で加熱脱水
することで容易に合成することができる。The plasticizer of the present invention can be prepared by a known method, for example, polyoxytetramethylene glycol, branched fatty acid,
It can be easily synthesized by heating and dehydrating a metal catalyst such as dibutyltin oxide at a high temperature.
【００１０】ゴム組成物中の本発明の可塑剤の含有量
は、耐寒性、ブリードや他物性への影響、更にコスト的
観点から、ゴム１００重量部に対して、３〜５０重量部
であり、好ましくは５〜４０重量部、さらに好ましくは
１０〜３０重量部である。[0010] The content of the plasticizer of the present invention in the rubber composition is 3 to 50 parts by weight based on 100 parts by weight of the rubber from the viewpoints of cold resistance, influence on bleeding and other physical properties, and cost. , Preferably 5 to 40 parts by weight, more preferably 10 to 30 parts by weight.
【００１１】本発明に係るゴムとしては、天然ゴム（Ｎ
Ｒ）、ブタジエンゴム（ＢＲ）、イソプレンゴム（Ｉ
Ｒ）、ブチルゴム（ＩＩＲ）、スチレンブタジエンゴム
（ＳＢＲ）、アクリロニトリルブタジエンゴム（ＮＢ
Ｒ）、エチレンプロピレンゴム（ＥＰＤＭ）、クロロプ
レンゴム（ＣＲ）、クロルスルホン化ポリエチレンゴム
（ＣＳＭ）、エピクロルヒドリンゴム（ＣＨＲ）等が挙
げられ、ＣＲ、ＣＳＭ、ＣＨＲが好ましく、ＣＲが特に
好ましい。As the rubber according to the present invention, natural rubber (N
R), butadiene rubber (BR), isoprene rubber (I
R), butyl rubber (IIR), styrene butadiene rubber (SBR), acrylonitrile butadiene rubber (NB
R), ethylene propylene rubber (EPDM), chloroprene rubber (CR), chlorosulfonated polyethylene rubber (CSM), epichlorohydrin rubber (CHR), and the like. CR, CSM, and CHR are preferable, and CR is particularly preferable.
【００１２】本発明のゴム組成物は通常の混練機、例え
ばバンバリーミキサー、ロール、インテンシブミキサー
等で容易に製造することができる。また、カーボンブラ
ック、シリカ等の補強剤や加硫促進剤、加硫剤等、通常
ゴムに配合される薬剤はもちろん、必要に応じて炭酸カ
ルシウム、タルク、クレー等の充填剤や着色剤、紫外線
吸収剤、汎用の可塑剤（フタル酸系、トリメリット酸
系、リン酸系、エポキシ系等）等を適宜添加することが
できる。The rubber composition of the present invention can be easily produced by a usual kneading machine, for example, a Banbury mixer, a roll, an intensive mixer or the like. In addition, carbon black, silica and other reinforcing agents, vulcanization accelerators, vulcanizing agents, etc., as well as chemicals usually compounded in rubber, as required, fillers and coloring agents such as calcium carbonate, talc, clay, etc. An absorbent, a general-purpose plasticizer (phthalic acid type, trimellitic acid type, phosphoric acid type, epoxy type, and the like) and the like can be appropriately added.
【００１３】[0013]
【実施例】例中の％は特記しない限り重量％である。EXAMPLES In the examples,% is% by weight unless otherwise specified.
【００１４】合成例１ 数平均分子量８５０のポリオキシテトラメチレングリコ
ールを５１０ｇと２−エチルヘキサン酸２０７ｇ、触媒
としてジブチルスズオキシド０．７ｇを１リットル四つ
口フラスコに秤取り、窒素吹き込みで２２５℃で脱水し
ながら、エステル化反応を５〜６時間行った後、過剰の
２−エチルヘキサン酸を留去して、エステル（ＰＴＧ８
５０２ＥＨ、組成：ジエステル９５％、モノエステル５
％）を得た。Synthesis Example 1 510 g of polyoxytetramethylene glycol having a number average molecular weight of 850, 207 g of 2-ethylhexanoic acid, and 0.7 g of dibutyltin oxide as a catalyst were weighed into a one-liter four-necked flask, and the mixture was blown with nitrogen at 225 ° C. After performing the esterification reaction for 5 to 6 hours while dehydrating, excess 2-ethylhexanoic acid was distilled off, and the ester (PTG8
502EH, composition: 95% of diester, monoester 5
%).
【００１５】合成例２ 数平均分子量８５０のポリオキシテトラメチレングリコ
ールを４２５ｇとイソパルミチン酸３０７ｇ、ジブチル
スズオキシド０．７ｇを合成例１と同様の方法で反応さ
せて、エステル（ＰＴＧ８５０ｉＰ、組成：ジエステル
８２％、モノエステル１８％）を得た。Synthesis Example 2 425 g of polyoxytetramethylene glycol having a number average molecular weight of 850, 307 g of isopalmitic acid, and 0.7 g of dibutyltin oxide were reacted in the same manner as in Synthesis Example 1 to obtain an ester (PTG850iP, composition: diester 82). %, Monoester 18%).
【００１６】合成例３ 数平均分子量２０００のポリオキシテトラメチレングリ
コール５００ｇと２−エチルヘキサン酸８６ｇ、ジブチ
ルスズオキシド０．６ｇを合成例１と同様の方法で反応
させて、エステル（ＰＴＧ２０００２ＥＨ、組成：ジエ
ステル７６％、モノエステル２４％）を得た。Synthesis Example 3 500 g of polyoxytetramethylene glycol having a number average molecular weight of 2,000, 86 g of 2-ethylhexanoic acid and 0.6 g of dibutyltin oxide were reacted in the same manner as in Synthesis Example 1 to obtain an ester (PTG20002EH, composition: diester). 76%, monoester 24%).
【００１７】合成例４ 数平均分子量８５０のポリオキシエチレンテトラメチレ
ングリコール５１０ｇとイソノナン酸２０８ｇ、ジブチ
ルスズオキシド０．７ｇを合成例１と同様の方法で反応
させて、エステル（ＰＴＧ８５０ｉＮ、組成：ジエステ
ル９１％、モノエステル９％）を得た。Synthesis Example 4 510 g of polyoxyethylene tetramethylene glycol having a number average molecular weight of 850, 208 g of isononanoic acid, and 0.7 g of dibutyltin oxide were reacted in the same manner as in Synthesis Example 1 to obtain an ester (PTG850iN, composition: 91% diester). , Monoester 9%).
【００１８】比較合成例１ 数平均分子量６００のポリプロピレングリコール４００
ｇと２−エチルヘキサン酸２３０ｇ、ジブチルスズオキ
シド０．６ｇを合成例１と同様の方法で反応させて、エ
ステル（ＰＰＧ２ＥＨ、組成：ジエステル９６％、モノ
エステル４％）を得た。Comparative Synthesis Example 1 Polypropylene glycol 400 having a number average molecular weight of 600
g, 230 g of 2-ethylhexanoic acid and 0.6 g of dibutyltin oxide were reacted in the same manner as in Synthesis Example 1 to obtain an ester (PPG2EH, composition: diester 96%, monoester 4%).
【００１９】比較合成例２ 数平均分子量８５０のポリオキシテトラメチレングリコ
ール４２５ｇとカプリル酸１７３ｇ、ジブチルスズオキ
シド０．６ｇを合成例１と同様の方法で反応させて、エ
ステル（ＰＴＧ８５０ＣＰ、組成：ジエステル９５％、
モノエステル５％）を得た。Comparative Synthesis Example 2 425 g of polyoxytetramethylene glycol having a number average molecular weight of 850, 173 g of caprylic acid and 0.6 g of dibutyltin oxide were reacted in the same manner as in Synthesis Example 1 to obtain an ester (PTG850CP, composition: 95% of diester). ,
Monoester 5%) was obtained.
【００２０】比較合成例３ 数平均分子量８５０のポリオキシテトラメチレングリコ
ール４２５ｇとイソステアリン酸３４０ｇ、ジブチルス
ズオキシド０．７ｇを合成例１と同様の方法で反応させ
て、エステル（ＰＴＧ８５０ｉＳｔ、組成：ジエステル
８６％、モノエステル１４％）を得た。Comparative Synthesis Example 3 425 g of polyoxytetramethylene glycol having a number average molecular weight of 850 was reacted with 340 g of isostearic acid and 0.7 g of dibutyltin oxide in the same manner as in Synthesis Example 1 to give an ester (PTG850iSt, composition: 86% of diester). , Monoester 14%).
【００２１】比較合成例４ アジピン酸３２１ｇ、１，４−ブタンジオール１８０
ｇ、ｎ−オクタノール５８ｇ及びジブチルスズオキシド
０．５５ｇを合成例１と同様の方法でエステル化を行
い、脱アルコールして、仕込み値より計算した平均分子
量約２５００のポリエステルＡを得た。Comparative Synthesis Example 4 Adipic acid 321 g, 1,4-butanediol 180
g, 58 g of n-octanol and 0.55 g of dibutyltin oxide were esterified in the same manner as in Synthesis Example 1 and dealcoholized to obtain a polyester A having an average molecular weight of about 2500 calculated from the charged values.
【００２２】比較合成例５ 数平均分子量１０００のポリオキシテトラメチレングリ
コール５１３ｇとラウリン酸２００ｇ、ジブチルスズオ
キシド０．７ｇを合成例１と同様の方法で反応させて、
エステル（ＰＴＧ１０００Ｌ、組成：ジエステル８７
％、モノエステル１３％）を得た。Comparative Synthesis Example 5 513 g of polyoxytetramethylene glycol having a number average molecular weight of 1,000, 200 g of lauric acid, and 0.7 g of dibutyltin oxide were reacted in the same manner as in Synthesis Example 1,
Ester (PTG1000L, composition: diester 87
%, Monoester 13%).
【００２３】実施例１〜７及び比較例１〜９ 合成例１〜４及び比較合成例１〜５で得られたエステ
ル、あるいは耐寒性向上に一般的に使われるジ２−エチ
ルヘキシルアジペートを可塑剤として用い、表１に示す
各種ＣＲ系ゴムで下記配合のゴム組成物を調製し、１７
０℃、１０分加硫を行い、厚さ２ｍｍのテストピースを
作製した。このテストピースについて、下記方法で耐寒
性、対グリース抽出性、耐熱性及びブリードを評価し
た。結果を表１に示す。Examples 1 to 7 and Comparative Examples 1 to 9 The ester obtained in Synthesis Examples 1 to 4 and Comparative Synthesis Examples 1 to 5 or di-2-ethylhexyl adipate, which is generally used for improving cold resistance, is used as a plasticizer. The following rubber compositions were prepared from the various CR rubbers shown in Table 1 and
Vulcanization was performed at 0 ° C. for 10 minutes to produce a test piece having a thickness of 2 mm. The test piece was evaluated for cold resistance, extractability with respect to grease, heat resistance and bleed by the following methods. Table 1 shows the results.
【００２４】＜ゴム組成物＞ ＣＲ系ゴム １００．０重量部 ＳＲＦカーボン*1 ６０．０重量部 老防ＰＡ*2 ５．０重量部 酸化マグネシウム ４．０重量部 酸化亜鉛 ５．０重量部 ステアリン酸 ２．０重量部 加硫促進剤２２*3 ０．５重量部 可塑剤 ３０．０重量部 *1 ＳＲＦカーボン:カーボンブラックＳＲＦ *2 老防ＰＡ:Ｎ−フェニル−α−ナフチルアミン *3 加硫促進剤２２:エチレンチオ尿素 ＜耐寒性＞ＪＩＳ Ｋ−６３０１（新ＪＩＳ Ｋ−６２
６１）の方法で、ゲーマン捻り試験で耐寒性の評価を行
った。Ｔ１００、Ｔ１０、Ｔ５、Ｔ２はそれぞれ、常温
（２３℃）に比べ捻りモジュラスが１００倍、１０倍、
５倍、２倍になる温度で、数字が低いほど耐寒性が良好
なことを示す。<Rubber composition> CR rubber 100.0 parts by weight SRF carbon * 1 60.0 parts by weight Anti-aging PA * 2 5.0 parts by weight Magnesium oxide 4.0 parts by weight Zinc oxide 5.0 parts by weight Stearin Acid 2.0 parts by weight Vulcanization accelerator 22 * 3 0.5 parts by weight Plasticizer 30.0 parts by weight * 1 SRF carbon: carbon black SRF * 2 Anti-aging PA: N-phenyl-α-naphthylamine * 3 Vulcanization Accelerator 22: ethylene thiourea <cold resistance> JIS K-6301 (new JIS K-62)
According to the method of 61), the cold resistance was evaluated by the Gehman twist test. Each of T100, T10, T5, and T2 has a twist modulus of 100 times, 10 times, and a normal temperature (23 ° C.).
At a temperature of 5 times and 2 times, the lower the number, the better the cold resistance.
【００２５】＜対グリース抽出性＞１０×１０ｃｍに切
断したテストピースに厚さ２０ｍｍになるようにグリー
スを塗布し、１２０℃の恒温機で５０時間放置した。そ
の後、室温でグリースを拭き取り、テストピースをＪＩ
Ｓ Ｋ−６３０１（新ＪＩＳ Ｋ−６２６１）の方法で
評価した。対グリース抽出後の耐寒性が良好なほど、グ
リースに抽出されにくいと言える。<Grease Extractability> Grease was applied to a test piece cut into a size of 10 × 10 cm so as to have a thickness of 20 mm, and the test piece was allowed to stand in a thermostat at 120 ° C. for 50 hours. After that, grease is wiped off at room temperature, and the test piece is
The evaluation was performed according to the method of SK-6301 (new JIS K-6261). It can be said that the better the cold resistance after extracting the grease, the more difficult it is to extract the grease.
【００２６】＜耐熱性＞テストピースを３号ダンベル型
に切断し、１２０℃、１００時間恒温機で放置して重量
変化から揮発分を測定した。揮発分が少ないほど耐熱性
が良好である。<Heat Resistance> The test piece was cut into a No. 3 dumbbell mold, left standing in a thermostat at 120 ° C. for 100 hours, and the volatile content was measured from the change in weight. The lower the volatile content, the better the heat resistance.
【００２７】＜ブリード＞テストピースを４０℃の雰囲
気下で７日間保存し、その表面状態を肉眼で観察し、下
記基準で評価した。<Bleed> The test pieces were stored in an atmosphere at 40 ° C. for 7 days, and the surface condition was visually observed and evaluated according to the following criteria.
【００２８】 ○：可塑剤のブリードが見られない △：若干のブリードがある ×：表面のブリードが激しい：: No bleeding of the plasticizer was observed. Δ: Slight bleeding ×: Severe bleeding on the surface
【００２９】[0029]
【表１】 [Table 1]
【００３０】[0030]
【発明の効果】本発明のゴム組成物は、低温における柔
軟性、特にＴ２、Ｔ５での柔軟性に優れ、且つグリース
等の油性物質による抽出が少なく、さらに高温下で揮発
しにくいため耐寒性の保持に優れている。The rubber composition of the present invention is excellent in flexibility at low temperatures, especially in T2 and T5, has little extraction by oily substances such as grease, and hardly volatilizes at high temperatures, and thus has low cold resistance. Excellent retention.
Claims (4)
キシテトラメチレングリコールと炭素数６〜１６の分岐
脂肪酸とのエステルからなるゴム用可塑剤。1. A rubber plasticizer comprising an ester of polyoxytetramethylene glycol having a number average molecular weight of 200 to 5,000 and a branched fatty acid having 6 to 16 carbon atoms.
ソノナン酸又はこれらの混合物である請求項１記載のゴ
ム用可塑剤。2. The rubber plasticizer according to claim 1, wherein the branched fatty acid is 2-ethylhexanoic acid, isononanoic acid or a mixture thereof.
００重量部に対して３〜５０重量部含有するゴム組成
物。3. The plasticizer according to claim 1 or 2,
A rubber composition containing 3 to 50 parts by weight based on 00 parts by weight.
記載のゴム組成物。4. The rubber according to claim 3, wherein the rubber is chloroprene rubber.
The rubber composition as described in the above.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001194482A JP4596405B2 (en) | 2000-09-07 | 2001-06-27 | Rubber composition |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000-271868 | 2000-09-07 | ||
| JP2000271868 | 2000-09-07 | ||
| JP2001194482A JP4596405B2 (en) | 2000-09-07 | 2001-06-27 | Rubber composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002155171A true JP2002155171A (en) | 2002-05-28 |
| JP4596405B2 JP4596405B2 (en) | 2010-12-08 |
Family
ID=26599449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001194482A Expired - Fee Related JP4596405B2 (en) | 2000-09-07 | 2001-06-27 | Rubber composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4596405B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011046175A1 (en) * | 2009-10-16 | 2011-04-21 | ダイソー株式会社 | Composition for semiconductive rubber, crosslinked rubber product, and semiconductive parts |
| EP3074489A1 (en) * | 2013-11-26 | 2016-10-05 | Basf Se | The use of polyalkylene glycol esters in lubricating oil compositions |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61145236A (en) * | 1984-12-19 | 1986-07-02 | Kao Corp | Chloroprene rubber composition |
| JPH07292235A (en) * | 1994-04-20 | 1995-11-07 | Sanyo Chem Ind Ltd | Low-temperature plasticizer |
-
2001
- 2001-06-27 JP JP2001194482A patent/JP4596405B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61145236A (en) * | 1984-12-19 | 1986-07-02 | Kao Corp | Chloroprene rubber composition |
| JPH07292235A (en) * | 1994-04-20 | 1995-11-07 | Sanyo Chem Ind Ltd | Low-temperature plasticizer |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011046175A1 (en) * | 2009-10-16 | 2011-04-21 | ダイソー株式会社 | Composition for semiconductive rubber, crosslinked rubber product, and semiconductive parts |
| US8735503B2 (en) | 2009-10-16 | 2014-05-27 | Daiso Co., Ltd. | Composition for semiconductive rubber, crosslinked rubber product, and semiconductive parts |
| JP5601478B2 (en) * | 2009-10-16 | 2014-10-08 | ダイソー株式会社 | Composition for semiconductive rubber, crosslinked rubber and semiconductive part |
| EP3074489A1 (en) * | 2013-11-26 | 2016-10-05 | Basf Se | The use of polyalkylene glycol esters in lubricating oil compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4596405B2 (en) | 2010-12-08 |
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