JPH064722B2 - Cold and heat resistant plasticizer for butadiene rubber - Google Patents
Cold and heat resistant plasticizer for butadiene rubberInfo
- Publication number
- JPH064722B2 JPH064722B2 JP61091536A JP9153686A JPH064722B2 JP H064722 B2 JPH064722 B2 JP H064722B2 JP 61091536 A JP61091536 A JP 61091536A JP 9153686 A JP9153686 A JP 9153686A JP H064722 B2 JPH064722 B2 JP H064722B2
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Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、ブタジエン系ゴム用耐寒耐熱性可塑剤に関す
る。更に詳しくは耐寒性の向上を図るばかりではなく、
耐熱性、特に低揮発性を特長とするブタジエン系ゴム用
耐寒耐熱性可塑剤に関する。TECHNICAL FIELD The present invention relates to a cold and heat resistant plasticizer for butadiene rubber. More specifically, it not only aims to improve cold resistance,
The present invention relates to a cold and heat resistant plasticizer for butadiene rubber, which is characterized by heat resistance, particularly low volatility.
近年、ゴム製品は用途の増加、使用範囲の拡大に伴い従
来以上に耐寒性及び耐熱性を向上させたものが望まれて
いる。従って、これらの改良対策は非常に積極的に行わ
れており、ゴム同士のブレンドによる改良、第三成分の
添加による改良が検討されており、かなりの成果は得ら
れているが、何れの方法においても長所、短所があり、
決定的な方法が見い出されていない。In recent years, rubber products have been desired to have improved cold resistance and heat resistance more than ever, with the increase of applications and expansion of use range. Therefore, these improvement measures are very positively taken, and improvement by blending rubbers and improvement by addition of a third component are being considered, and considerable results have been obtained, but either method There are advantages and disadvantages in
No definitive method has been found.
例えば、耐寒性が比較的良好とされている天然ゴム（以
下NRと略）やポリブタジエンゴム（以下BRと略）を耐寒
性の劣るアクリロニトリル−ブタジエンゴム（以下NBR
と略）やクロロプレンゴム（以下CRと略）にブレンドす
る事により、NBRやCRの耐寒性を改良しようという方法
があるが、充分に耐寒性を改良する為にはNRやBRを多量
にブレンドしなければならず、又、ゴム同士の相溶性に
も問題がある為、NBRやCRの物理的・化学的性質が損な
われる事が多い。For example, natural rubber (hereinafter abbreviated as NR) and polybutadiene rubber (hereinafter abbreviated as BR), which are considered to have relatively good cold resistance, are used for acrylonitrile-butadiene rubber (hereinafter NBR), which has poor cold resistance.
There is a method to improve the cold resistance of NBR and CR by blending it with chloroprene rubber (hereinafter abbreviated as CR), but in order to improve cold resistance sufficiently, blend a large amount of NR and BR. Since there is also a problem with the compatibility between rubbers, the physical and chemical properties of NBR and CR are often impaired.
又、第三成分の添加としては、NRやスチレン−ブタンジ
エンゴム（以下、SBRと略）に対して、ジオクチルセバ
ケート（以下DOSと略）、ジイソブチルアジペート（以
下DIBAと略）などが、又、CRやNBRに対してはジブチル
セバケート、DOSなどが公知であるが、これらは耐寒性
の向上はみられるものの、耐熱性については、極めて悪
い結果を示す。ぇた、ポリエステル系可塑剤は様々な種
類のものがみられ、耐熱性については向上しているが、
耐寒性が悪い。この傾向はトリメリット酸エステル系可
塑剤、ピロメリット酸エステル系可塑剤についても同様
であり、耐寒性、耐熱性の両者が優れた可塑剤というも
のは知られていなかった。In addition, as the addition of the third component, dioctyl sebacate (hereinafter abbreviated as DOS), diisobutyl adipate (hereinafter abbreviated as DIBA), etc. to NR and styrene-butanediene rubber (hereinafter abbreviated as SBR), Dibutyl sebacate, DOS, etc. are well known for CR, NBR, etc., but although they have improved cold resistance, they show extremely poor heat resistance. There are various types of polyester plasticizers, and they have improved heat resistance.
Poor cold resistance. This tendency also applies to trimellitic acid ester-based plasticizers and pyromellitic acid ester-based plasticizers, and plasticizers excellent in both cold resistance and heat resistance have not been known.
そこで、本発明者らは、ゴムの耐寒性及び耐熱性その他
の諸物性を向上せしめる可塑剤の開発すべく、鋭意検討
を行った結果、特定のグリコール成分と特定の脂肪酸成
分から導かれるエステルが、耐寒・耐熱の両特性を向上
せしめる事を見い出し、本発明に到達した。Therefore, the inventors of the present invention have conducted extensive studies in order to develop a plasticizer that improves cold resistance and heat resistance and other physical properties of rubber, and as a result, found that an ester derived from a specific glycol component and a specific fatty acid component was As a result, they have found that they can improve both cold resistance and heat resistance, and have reached the present invention.
即ち、本発明は、 分子量200〜5,000でアルキレン基の炭素数が２〜３の
ポリオキシアルキレングリコールと、炭素数14〜22の不
飽和脂肪酸もしくは（及び）炭素数２〜24の飽和脂肪酸
とを反応させて得られる分子量が600〜6,000のジエステ
ル、 分子量200〜5,000でアルキレン基の炭素数が２〜３の
ポリオキシアルキレングリコールと、炭素数14〜22の不
飽和脂肪酸もしくは（及び）炭素数２〜24の飽和脂肪酸
と、炭素数２〜10ノジカルボン酸もしくは（及び）ポリ
マー酸とを反応させて得られる分子量600〜6,000のポリ
エステル から選ばれる１種又は２種以上からなるブタジエン系ゴ
ム用耐寒耐熱性可塑剤を提供するものである。That is, the present invention provides a polyoxyalkylene glycol having a molecular weight of 200 to 5,000 and an alkylene group having 2 to 3 carbon atoms and an unsaturated fatty acid having 14 to 22 carbon atoms and / or a saturated fatty acid having 2 to 24 carbon atoms. A diester having a molecular weight of 600 to 6,000 obtained by the reaction, a polyoxyalkylene glycol having a molecular weight of 200 to 5,000 and an alkylene group having 2 to 3 carbon atoms, and an unsaturated fatty acid having 14 to 22 carbon atoms and / or 2 carbon atoms Cold resistance for butadiene rubber consisting of one or more selected from polyesters having a molecular weight of 600 to 6,000 obtained by reacting a saturated fatty acid having 24 to 24 with a nodicarboxylic acid having 2 to 10 carbon atoms and / or a polymer acid. A heat resistant plasticizer is provided.
本発明に用いられるアルキレン基の炭素数が２〜３のポ
リオキシアルキレングリコールとしては例えば、ポリエ
チレングリコール、ポリプロピレングリコール、エチレ
ンオキサイドとプロピレンオキサイドとのランダム又は
ブロック共重合体等が挙げられる。これらポリオキシア
ルキレングリコールの分子量は200〜5,000であることが
必要であり、特に500〜2,000のものが、耐寒、耐熱の両
特性が優れているので好ましい。Examples of the polyoxyalkylene glycol having an alkylene group having 2 to 3 carbon atoms used in the present invention include polyethylene glycol, polypropylene glycol, and random or block copolymers of ethylene oxide and propylene oxide. The molecular weight of these polyoxyalkylene glycols is required to be 200 to 5,000, and those having a molecular weight of 500 to 2,000 are particularly preferable because they have excellent cold resistance and heat resistance.
本発明においては、ポリオキシアルキレングリコール単
独では極性が強い為、ゴムとの相溶性に問題があり、脂
肪酸成分でエステル化を行い、これを改良した。In the present invention, since polyoxyalkylene glycol alone has a strong polarity, there is a problem in compatibility with rubber, and esterification with a fatty acid component was carried out to improve this.
本発明に用いられる脂肪酸成分のうち、炭素数14〜22の
不飽和脂肪酸としては、例えばミリストレイン酸、パル
ミトレイン酸、オレイン酸、エルカ酸、リノール酸、リ
ノレン酸等が挙げられる。炭素数２〜24の飽和脂肪酸と
しては、酢酸、酪酸、カプロン酸、カプリル酸、ラウリ
ン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ア
ラキン酸、ベヘニン酸等が挙げられる。Among the fatty acid components used in the present invention, examples of unsaturated fatty acids having 14 to 22 carbon atoms include myristoleic acid, palmitoleic acid, oleic acid, erucic acid, linoleic acid and linolenic acid. Examples of the saturated fatty acid having 2 to 24 carbon atoms include acetic acid, butyric acid, caproic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid and behenic acid.
又、炭素数２〜10のジカルボン酸としては、例えばシュ
ウ酸、コハク酸、アジピン酸、アゼライン酸、セバシン
酸等が挙げられ、ポリマー酸としては、上述の炭素数14
〜22の不飽和脂肪酸を２量体以上に多量化したものが挙
げられる。The dicarboxylic acid having 2 to 10 carbon atoms includes, for example, oxalic acid, succinic acid, adipic acid, azelaic acid, sebacic acid, and the like.
Examples of unsaturated fatty acids of up to 22 are dimerized or more.
本発明にかかるエステルは、一般公知のエステル化方法
により上記グリコール成分と脂肪酸成分をエステル化し
て得られる。得られるエステルの分子量は600〜6000の
範囲であり、好ましくは600〜2500の範囲である。The ester according to the present invention can be obtained by esterifying the glycol component and the fatty acid component by a generally known esterification method. The molecular weight of the resulting ester is in the range 600-6000, preferably in the range 600-2500.
本発明の前記〜から選ばれるエステル化合物からな
る耐寒耐熱性可塑剤の配合割合はブタジエン系ゴム100
重量部に対し、５〜60重量部、好ましくは10〜40重量部
である。５重量部未満の配合では充分な耐寒性は期待出
来ず、60重量部以上になるとゴム物性等への影響が大き
く、又、経済性への面でも好ましくない。The blending ratio of the cold and heat resistant plasticizer comprising an ester compound selected from the above items of the present invention is 100% butadiene rubber.
It is 5 to 60 parts by weight, preferably 10 to 40 parts by weight, based on parts by weight. If the amount is less than 5 parts by weight, sufficient cold resistance cannot be expected, and if the amount is more than 60 parts by weight, the physical properties of rubber and the like are greatly affected, and the economical efficiency is not preferable.
又、本発明にかかる耐寒耐熱性可塑剤はDOS、DOZ、DOA
等の一般の可塑剤と併用することができる。The cold and heat resistant plasticizer according to the present invention is DOS, DOZ, DOA.
Can be used in combination with general plasticizers such as
本発明き可塑剤が適用されるブタジエン系ゴムとしては
SBR、NBR等のブタジエン共重合ゴム及び天然ゴムが挙げ
られる。The butadiene rubber to which the plasticizer of the present invention is applied is
Examples thereof include butadiene copolymer rubber such as SBR and NBR and natural rubber.
尚、本発明のブタジエン系ゴム用耐寒耐熱性可塑剤の配
合であるが、通常のゴム混練法、例えばオープンロー
ル、バンバリーミキサー、ニーダーブレンダー等で行う
事が出来る。又、ゴム工業で通常、使用される配合剤、
例えば補強剤、加流剤、加流促進剤、充填剤、軟化剤、
老化防止剤、加工助剤等適宜添加する事が出来る。The cold- and heat-resistant plasticizer for butadiene rubber of the present invention can be compounded by a usual rubber kneading method such as an open roll, Banbury mixer, kneader blender or the like. Also, compounding agents normally used in the rubber industry,
For example, reinforcing agent, flow agent, flow accelerator, filler, softening agent,
Antiaging agents, processing aids and the like can be added as appropriate.
以下、実施例によって本発明を詳述するが、これらによ
って本発明が限定されるものではない。Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited thereto.
実施例１ ポリプロピレングリコール2000g（分子量2000，1.0モ
ル）にオレイン酸552g（2.0モル）、SnO1.3g（0.05重量
％）を加え、窒素ガスの存在下、230℃で６時間脱水反
応後、ポリプロピレングリコールジオレート（PPG20，
分子量約2550）を得た。Example 1 To 2,000 g of polypropylene glycol (molecular weight 2000, 1.0 mol), 552 g (2.0 mol) of oleic acid and 1.3 g (0.05% by weight) of SnO were added, and after dehydration reaction at 230 ° C. for 6 hours in the presence of nitrogen gas, polypropylene glycol Georate (PPG20,
A molecular weight of about 2550) was obtained.
実施例２ ポリエチレングリコール800g（分子量400，2.0モル）に
リノール酸のダイマー酸560g（1.0モル）、SnO0.68g
（0.05重量％）を加え、実施例１と同様の方法でエステ
ル化した後、無水酢酸306gを窒素ガスの存在下、90〜10
0℃で滴下し、アセチル化後、過剰の無水酢酸をトッピ
ングにて除去し、ポリエチレングリコールダイマー酸エ
ステルアセチル化物（PEGDA，分子量約1408）を得た。Example 2 Polyethylene glycol 800 g (molecular weight 400, 2.0 mol), dimer acid of linoleic acid 560 g (1.0 mol), SnO 0.68 g
(0.05% by weight) was added and esterification was carried out in the same manner as in Example 1, and then 306 g of acetic anhydride was added in the presence of nitrogen gas at 90 to 10%.
After dropwise addition at 0 ° C. and acetylation, excess acetic anhydride was removed by topping to obtain a polyethylene glycol dimer acid ester acetylated product (PEGDA, molecular weight about 1408).
試験例１ NBR100重量部に対し、実施例１〜２の化合物及び比較例
としてアゼライン酸ジオクチル（以下DOZと略）、ポリ
エステル系可塑剤（分子量700のプロピレングリコール
とアジピン酸とのエステル）を各々30重量部、下記の配
合物に添加し、オープンロールにて混練し、ゴム組成物
を作成した。Test Example 1 With respect to 100 parts by weight of NBR, 30 each of the compounds of Examples 1 and 2, dioctyl azelate (hereinafter abbreviated as DOZ), and a polyester plasticizer (ester of propylene glycol having a molecular weight of 700 and adipic acid) were used as comparative examples. Parts by weight were added to the following composition and kneaded with an open roll to prepare a rubber composition.
中高ニトリルNBR 100重量部 ステアリン酸 1 〃 カーボンブラックSRF 40 〃 亜鉛華三号 3 〃 促進剤DM 0.7 〃 イオウ 1.5 〃 当該ゴム組成物は温度160℃、時間20分間の条件で加硫
し、得られた加硫ゴム組成物について耐寒性試験、耐熱
性試験を行った。耐寒性試験はJISK-6301に準拠し、耐
熱性試験は120±１℃恒温槽に試験片を入れ、48時間及
び10日間での重量減を調べた。結果は表−１に示す。Medium-high nitrile NBR 100 parts by weight Stearic acid 1 〃 Carbon black SRF 40 〃 Zinc flower No. 3 〃 Accelerator DM 0.7 〃 Sulfur 1.5 〃 The rubber composition was obtained by vulcanizing at a temperature of 160 ° C for 20 minutes. The vulcanized rubber composition was subjected to a cold resistance test and a heat resistance test. The cold resistance test complies with JIS K-6301, and the heat resistance test was carried out by placing the test piece in a 120 ° C ± 1 ° C constant temperature bath and examining the weight loss after 48 hours and 10 days. The results are shown in Table-1.
試験例２ SBR100重量部に対し、実施例１〜２の化合物及び比較例
としてDOZ、ポリエステル系可塑剤（分子量700のプロピ
レングリコールとアジピン酸とのエステル）を各々20重
量部下記の配合物に添加し、オープンロールにて混練
し、ゴム組成物を作成した。 Test Example 2 To 100 parts by weight of SBR, 20 parts by weight of each of the compounds of Examples 1 and 2 and DOZ as a comparative example, a polyester plasticizer (ester of propylene glycol having a molecular weight of 700 and adipic acid) were added to the following composition. Then, the mixture was kneaded with an open roll to prepare a rubber composition.
SBR#1502 100重量部 ステアリン酸 1 〃 カーボンブラックHAF 65 〃 亜鉛華三号 3 〃 イオウ 1.75 〃 促進剤CZ 1 〃 当該ゴム組成物は温度160℃、時間10分間の条件で加流
し、得られた加硫ゴム組成物について耐寒性試験、耐熱
性試験を行った。試験方法は試験例１と同様の方法で行
った。結果は表−２に示す。SBR # 1502 100 parts by weight Stearic acid 1 〃 Carbon black HAF 65 〃 Zinc Huasan 3 〃 Sulfur 1.75 〃 Accelerator CZ 1 〃 The rubber composition was obtained by accelerating at a temperature of 160 ° C for 10 minutes. The vulcanized rubber composition was subjected to a cold resistance test and a heat resistance test. The test method was the same as in Test Example 1. The results are shown in Table-2.
試験例３ NBR100重量部に対し、ポリエチレングリコール（分子量
400)ジカプリレート(PEG(400)2K)、及び比較例として
１，６−ヘキサンジオールジオレエート(HD20)とポリエ
チレングリコール（分子量200)ジカプリレート(PEG(20
0)2K)を各々15重量部、下記の配合物に添加し、オープ
ンロールにて混練し、ゴム組成物を作成した。 Test Example 3 Based on 100 parts by weight of NBR, polyethylene glycol (molecular weight
400) dicaprylate (PEG (400) 2K), and as a comparative example, 1,6-hexanediol dioleate (HD20) and polyethylene glycol (molecular weight 200) dicaprylate (PEG (20
15 parts by weight of each of (0) 2K) was added to the following composition and kneaded with an open roll to prepare a rubber composition.
中高ニトリルNBR 100重量部 ステアリン酸 1 〃 カーボンブラックSRF 50 〃 亜鉛華三号 5 〃 促進剤DM 1 〃 イオウ 1.5 〃 BHT 2 〃 当該ゴム組成物は温度160℃、時間15分間の条件で加硫
し、得られた加硫ゴム組成物について耐寒性試験、耐熱
性試験を行った。耐寒性試験はJISK-6301に準拠し、耐
熱性試験は120±１℃恒温槽に試験片を入れ、200時間で
の重量減を調べた。結果は表−３に示す。Medium-high nitrile NBR 100 parts by weight Stearic acid 1 〃 Carbon black SRF 50 〃 Zinc Hua No. 3 5 〃 Accelerator DM 1 〃 Sulfur 1.5 〃 BHT 2 〃 The rubber composition is vulcanized at 160 ℃ for 15 minutes. A cold resistance test and a heat resistance test were performed on the obtained vulcanized rubber composition. The cold resistance test complied with JIS K-6301, and the heat resistance test was carried out by placing the test piece in a 120 ± 1 ° C. constant temperature bath and examining the weight loss after 200 hours. The results are shown in Table-3.
表−１〜表−３からわかる様に本発明の可塑剤は耐寒性
が優れ、且つ、高温時の揮発分も少なく、耐熱性が良好
である。 As can be seen from Table-1 to Table-3, the plasticizer of the present invention has excellent cold resistance, less volatile content at high temperature, and good heat resistance.
Claims (2)
が２〜３のポリオキシアルキレングリコールと、炭素数
14〜22の不飽和脂肪酸もしくは（及び）炭素数２〜24の
飽和脂肪酸とを反応させて得られる分子量が600〜6,000
のジエステル、1. A polyoxyalkylene glycol having a molecular weight of 200 to 5,000 and an alkylene group having 2 to 3 carbon atoms, and a carbon number.
The molecular weight obtained by reacting an unsaturated fatty acid having 14 to 22 or (and) a saturated fatty acid having 2 to 24 carbon atoms is 600 to 6,000.
The diester of
が２〜３のポリオキシアルキレングリコールと、炭素数
14〜22の不飽和脂肪酸もしくは（及び）炭素数２〜24の
飽和脂肪酸と、炭素数２〜10のジカルボン酸もしくは
（及び）ポリマー酸とを反応させて得られる分子量600
〜6,000のポリエステル から選ばれる１種又は２種以上からなるブタジエン系ゴ
ム用耐寒耐熱性可塑剤。2. A polyoxyalkylene glycol having a molecular weight of 200 to 5,000 and an alkylene group having a carbon number of 2 to 3, and a carbon number of
A molecular weight of 600, which is obtained by reacting an unsaturated fatty acid having 14 to 22 or (and) a saturated fatty acid having 2 to 24 carbon atoms with a dicarboxylic acid or (and) polymer acid having 2 to 10 carbon atoms.
A cold- and heat-resistant plasticizer for butadiene-based rubbers, which comprises one or more selected from polyesters of up to 6,000.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61091536A JPH064722B2 (en) | 1986-04-21 | 1986-04-21 | Cold and heat resistant plasticizer for butadiene rubber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61091536A JPH064722B2 (en) | 1986-04-21 | 1986-04-21 | Cold and heat resistant plasticizer for butadiene rubber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62253643A JPS62253643A (en) | 1987-11-05 |
| JPH064722B2 true JPH064722B2 (en) | 1994-01-19 |
Family
ID=14029182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61091536A Expired - Lifetime JPH064722B2 (en) | 1986-04-21 | 1986-04-21 | Cold and heat resistant plasticizer for butadiene rubber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH064722B2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2164306T3 (en) * | 1996-12-17 | 2002-02-16 | Bridgestone Corp | RUBBER COMPOSITION WITH IMPROVED TRANSFORMATION CAPACITY. |
| US6809137B2 (en) | 1998-06-08 | 2004-10-26 | Bridgestone Corporation | Rubber composition and pneumatic tire using said rubber composition |
| JP4515004B2 (en) * | 2001-09-14 | 2010-07-28 | 花王株式会社 | Rubber composition |
| KR20160097199A (en) * | 2013-12-10 | 2016-08-17 | 제온 코포레이션 | Vinyl chloride resin composition, vinyl chloride resin molded article, and laminate |
| EP3121228B1 (en) | 2014-03-18 | 2020-05-06 | Zeon Corporation | Vinyl chloride resin composition, vinyl chloride resin molded product, and laminate |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3489723A (en) * | 1966-12-06 | 1970-01-13 | Nopco Chem Co | Two-component castable polyurethane elastomer composition and use |
| JPS55142768A (en) * | 1979-04-18 | 1980-11-07 | Sanyo Chemical Ind Ltd | Treating oil agent for synthetic fiber |
| JPS59109553A (en) * | 1982-12-14 | 1984-06-25 | Sanyo Chem Ind Ltd | Polymer composition |
| JPS59109548A (en) * | 1982-12-16 | 1984-06-25 | Sanyo Chem Ind Ltd | Polymer composition |
| JPS60137945A (en) * | 1983-12-26 | 1985-07-22 | Yokohama Rubber Co Ltd:The | Rubber composition for tire tread |
| JPS60215403A (en) * | 1984-04-10 | 1985-10-28 | Bridgestone Corp | Low fuel consumption tire with all weather performance |
| JPS6140343A (en) * | 1984-08-01 | 1986-02-26 | Toyo Soda Mfg Co Ltd | Production of powdery rubber |
-
1986
- 1986-04-21 JP JP61091536A patent/JPH064722B2/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3489723A (en) * | 1966-12-06 | 1970-01-13 | Nopco Chem Co | Two-component castable polyurethane elastomer composition and use |
| JPS55142768A (en) * | 1979-04-18 | 1980-11-07 | Sanyo Chemical Ind Ltd | Treating oil agent for synthetic fiber |
| JPS59109553A (en) * | 1982-12-14 | 1984-06-25 | Sanyo Chem Ind Ltd | Polymer composition |
| JPS59109548A (en) * | 1982-12-16 | 1984-06-25 | Sanyo Chem Ind Ltd | Polymer composition |
| JPS60137945A (en) * | 1983-12-26 | 1985-07-22 | Yokohama Rubber Co Ltd:The | Rubber composition for tire tread |
| JPS60215403A (en) * | 1984-04-10 | 1985-10-28 | Bridgestone Corp | Low fuel consumption tire with all weather performance |
| JPS6140343A (en) * | 1984-08-01 | 1986-02-26 | Toyo Soda Mfg Co Ltd | Production of powdery rubber |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101702259B1 (en) * | 2016-01-11 | 2017-02-06 | 손상영 | Apparatus for generating droplets |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62253643A (en) | 1987-11-05 |
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