JPS63154760A - Fire-retardant ethylenic resin composition - Google Patents
Fire-retardant ethylenic resin compositionInfo
- Publication number
- JPS63154760A JPS63154760A JP30146386A JP30146386A JPS63154760A JP S63154760 A JPS63154760 A JP S63154760A JP 30146386 A JP30146386 A JP 30146386A JP 30146386 A JP30146386 A JP 30146386A JP S63154760 A JPS63154760 A JP S63154760A
- Authority
- JP
- Japan
- Prior art keywords
- ethylene
- anhydride
- acid
- weight
- resin composition
- 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.)
- Pending
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 17
- 239000011342 resin composition Substances 0.000 title claims description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 12
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 11
- 239000002184 metal Substances 0.000 claims abstract description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001530 fumaric acid Substances 0.000 claims abstract description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims abstract description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 4
- 239000011976 maleic acid Substances 0.000 claims abstract description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims abstract description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims abstract description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims abstract description 3
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 claims abstract 2
- 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 claims description 15
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- 229920001038 ethylene copolymer Polymers 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 7
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 abstract description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract description 2
- 229920006026 co-polymeric resin Polymers 0.000 abstract 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 abstract 1
- 239000005038 ethylene vinyl acetate Substances 0.000 abstract 1
- 229910001679 gibbsite Inorganic materials 0.000 abstract 1
- 235000012254 magnesium hydroxide Nutrition 0.000 abstract 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- -1 dicumyl peroxide Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920005672 polyolefin resin Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 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 description 1
- 239000011295 pitch Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は難燃性エチレン系樹脂組成物に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a flame-retardant ethylene resin composition.
（従来の技術）
一般にポリオレフィン系樹脂は機械的特性、電気的特性
、耐薬品性、加工性等に優れているものであるが、その
反面易燃性を有するという欠点がある。これを改善する
方法として該樹脂に難燃剤を添加せる組成物が出現され
ており、この難燃剤として燃焼時の脱水吸熱反応を利用
する金属水和物が広範囲に使用されている。然しなから
難燃剤を多量配合すると引張り強度等の機械的特性が著
しく低下するという問題を生ずるものであった。(Prior Art) Generally, polyolefin resins have excellent mechanical properties, electrical properties, chemical resistance, processability, etc., but on the other hand, they have the drawback of being easily flammable. As a method to improve this, a composition has been developed in which a flame retardant is added to the resin, and metal hydrates that utilize the endothermic reaction of dehydration during combustion are widely used as the flame retardant. However, when a large amount of flame retardant is added, a problem arises in that mechanical properties such as tensile strength are significantly reduced.
（発明が解決しようとする問題点）
本発明はエチレン系共重合樹脂に難燃剤を添加して難燃
性を付与するにおいて、何等機械的特性を低下せしめる
ことなく、難燃性を向上せしめ得た難燃性ポリオレフィ
ン系組成物を開発したものである。(Problems to be Solved by the Invention) The present invention provides flame retardance by adding a flame retardant to an ethylene copolymer resin, which improves the flame retardance without any deterioration of mechanical properties. The company has developed a flame-retardant polyolefin composition.
（問題点を解決するための手段）
本発明はエチレン系共重合樹脂１００重量部に対し不飽
和カルボン酸またはその無水物０．０５〜５．０重量部
をグラフトさせたグラフト化物１００重量部に対して金
属水和物１００〜２００重量部を添加したことを特徴と
するものである。(Means for Solving the Problems) The present invention provides 100 parts by weight of a grafted product obtained by grafting 0.05 to 5.0 parts by weight of an unsaturated carboxylic acid or anhydride thereof to 100 parts by weight of an ethylene copolymer resin. It is characterized by adding 100 to 200 parts by weight of a metal hydrate.
本発明においてエチレン系共重合樹脂としては、エチレ
ン、エチルアクリレート共重合体又はエチレン、酢酸ビ
ニル共重合体が好ましく、このエチレンエチルアクリレ
ート共重合体中のエチルアクリレート含有料又はエチレ
ン、酢酸ビニル共重合体中の酢酸ビニル含有量はそれぞ
れ５〜５０重量％が望ましく、特に１０〜３０重量％が
好ましいものである。In the present invention, the ethylene copolymer resin is preferably an ethylene, ethyl acrylate copolymer or an ethylene, vinyl acetate copolymer; The vinyl acetate content in each is preferably 5 to 50% by weight, particularly preferably 10 to 30% by weight.
又、本発明においてエチレン系共重合樹脂にグラフトさ
せる不飽和物カルボン酸またはその無水物としては、ア
クリル酸、マレイン酸、無水マレイン酸、フマル酸、メ
タクリル酸、シトラコン酸。In the present invention, examples of the unsaturated carboxylic acid or anhydride thereof to be grafted onto the ethylene copolymer resin include acrylic acid, maleic acid, maleic anhydride, fumaric acid, methacrylic acid, and citraconic acid.
無水シトラコン酸、イタコン酸、無水イタコン酸等を使
用するものであるが、特にアクリル酸、メタクリル酸、
マレイン酸、無水マレイン酸、フマル酸は安価であり且
つ良好な結果が得られるものである。It uses citraconic anhydride, itaconic acid, itaconic anhydride, etc., but especially acrylic acid, methacrylic acid,
Maleic acid, maleic anhydride, and fumaric acid are inexpensive and give good results.
この不飽和カルボン酸またはその無水物のグラフトｆｆ
ｉはエチレン系共重合樹脂１００重量部に対し０．０５
〜５．０重量部に限定したが、その理由は０．０５重量
部未満のものでは、本発明の目的とする機械的特性の低
下を防止することが出来ないものであり、又５．０重量
部を超えたものでは、不飽和カルボン酸またはその無水
物のグラフトによる効果が向上することなく、むしろ未
反応の不飽和カルボン酸またはその無水物により色相に
悪影響を及ぼすと共に気泡を発生して外観を阻害し且つ
性能を低下せしめるものである。Grafting of this unsaturated carboxylic acid or its anhydrideff
i is 0.05 per 100 parts by weight of ethylene copolymer resin
The content was limited to ~5.0 parts by weight, because if it is less than 0.05 parts by weight, it is impossible to prevent the deterioration of mechanical properties, which is the objective of the present invention. If the amount exceeds 1 part by weight, the effect of grafting the unsaturated carboxylic acid or its anhydride will not be improved, but rather the unreacted unsaturated carboxylic acid or its anhydride will adversely affect the hue and generate bubbles. This impairs the appearance and reduces performance.
又本発明における金属水和物は難燃剤として使用するも
のであり、難燃剤として使用されている金属水和物であ
れば何ずれのものでもよいが、特に水酸化マグネシウム
、水酸化アルミニウムが好ましい。その配合量において
エチレン系共重合樹脂１００重量部に対して１００〜２
００重量部を添加するものであり、その理由は１００重
量部未満の場合には難燃性を向上せしめることが出来ず
、又２００重量部を超えた場合には組成物の機械的特性
が低下する傾向を示すためである。Further, the metal hydrate in the present invention is used as a flame retardant, and any metal hydrate used as a flame retardant may be used, but magnesium hydroxide and aluminum hydroxide are particularly preferred. . The blending amount is 100 to 2 parts by weight per 100 parts by weight of ethylene copolymer resin.
The reason for this is that if the amount is less than 100 parts by weight, the flame retardance cannot be improved, and if it exceeds 200 parts by weight, the mechanical properties of the composition will deteriorate. This is to show the tendency to
（作用）
本発明においてポリオレフィン系樹脂を不飽和カルボン
酸又はその無水物によりグラフト化せしめる理由は、エ
チレン系共重合樹脂を金属水和物の難燃性剤との濡れ性
を良好にするためである。(Function) The reason why the polyolefin resin is grafted with an unsaturated carboxylic acid or its anhydride in the present invention is to improve the wettability of the ethylene copolymer resin with the metal hydrate flame retardant. be.
１よ
即ちエチレン系重合樹脂巻無極性のため極性を有する金
属水和物と均一に混和しがたいため、予め該エチレン系
共重合樹脂をカルボキシル基を有する不飽和カルボン酸
又はその無水物によりグラフト化せしめて該樹脂にて極
性を付与せしめるものである。1, that is, the ethylene copolymer resin is non-polar and difficult to mix uniformly with polar metal hydrates. This is to impart polarity to the resin.
なおエチレン系共重合樹脂をグラフト化せしめる方法と
しては、有機過酸化物例えばジクミルパーオキサイド、
ベンゾイルパーオキサイド等のラジカル発生剤を少量添
加し高温に加熱して行うものである。In addition, as a method for grafting the ethylene copolymer resin, an organic peroxide such as dicumyl peroxide,
This is done by adding a small amount of a radical generator such as benzoyl peroxide and heating to a high temperature.
（実施例）
第１表に示す如くエチレン系共重合体樹脂に不飽和カル
ボンサン、ベンゾイルパーオキサイド。(Example) As shown in Table 1, unsaturated carboxylic acid and benzoyl peroxide were added to the ethylene copolymer resin.
老化防止剤を夫々配合した混和物をＬ／Ｄ−３０゜Ｄ−
５５Ｍφ、ピッチ数５０のフルフライトスクリューを有
する押出機に供給し、温度１７０’Ｃ。A mixture containing anti-aging agents is L/D-30°D-
It was fed to an extruder with a full flight screw of 55 Mφ and 50 pitches, and the temperature was 170'C.
回転数１０ｒ、ρ＋ｌｌｌにて押出してグラフトポリマ
ーとした。このグラフトポリマーに金属水和物を配合し
オーブンロールにて混練を行って本発明組成物によるシ
ート及び比較例組成物によるシートをえた。A graft polymer was obtained by extrusion at a rotation speed of 10 r and ρ+1ll. A metal hydrate was blended with this graft polymer and kneaded using an oven roll to obtain a sheet of the composition of the present invention and a sheet of the comparative composition.
斯くして得たシートについて引張りの強さ、伸び及び酸
素指数を夫々測定した。その結果は第１表に詳記した通
りである。The tensile strength, elongation and oxygen index of the sheet thus obtained were measured. The results are detailed in Table 1.
注＊Ｉ ＤＰＤＪ−６１６９日本ユニカー社製＊２
ＤＱＤＪ−１８６９日本ユニカー社製本３ 日本チバ
ガイギー社製：ペンタエリスリチルーテトラキス［３−
（３，５−
ジ−ブチル−４−ヒドロキシフェニル）プロピオネート
］
＊４ キスマ５Ａ：協和化学工業社製（難燃剤）を９０
℃、９０Ｈｒ熱風乾燥して
使用
＊５ ハイシライトＨ−４２Ｍ：昭和軽金属社製（難燃
剤）を９０℃、９ＱＨｒ熱
風乾燥して使用
（効果）
以上詳述した如く本発明難燃性エチレン系樹脂組成物に
よれば機械的特性を低下せしめることなく、難燃性を著
しく向上せしめる等工業上極めてを用のものである。Note *I DPDJ-6169 Manufactured by Nippon Unicar *2
DQDJ-1869 Nippon Unicar Co., Ltd. Binding 3 Nippon Ciba Geigy Co., Ltd.: Pentaerythrityl Tetrakis [3-
(3,5-di-butyl-4-hydroxyphenyl)propionate] *4 Kisuma 5A: manufactured by Kyowa Chemical Industry Co., Ltd. (flame retardant) at 90%
Used after drying with hot air at 90°C for 90 hours *5 Hisilite H-42M: Manufactured by Showa Light Metal Co., Ltd. (flame retardant) used after drying with hot air at 90°C for 9Q hours (effect) As detailed above, the flame-retardant ethylene resin composition of the present invention According to the product, it is extremely useful in industry, as it significantly improves flame retardancy without deteriorating mechanical properties.
Claims (4)
和カルボン酸またはその無水物０．０５〜５．０重量部
をグラフトさせたグラフト化物に対して金属水和物１０
０〜２００重量部を添加したことを特徴とする難燃性エ
チレン系樹脂組成物。(1) 10 parts by weight of metal hydrate for a grafted product obtained by grafting 0.05 to 5.0 parts by weight of an unsaturated carboxylic acid or its anhydride to 100 parts by weight of ethylene copolymer resin.
A flame-retardant ethylene resin composition, characterized in that it contains 0 to 200 parts by weight.
ート共重合体又はエチレン、酢酸ビニル共重合体の群か
ら選ばれた１種又は２種以上からなることを特徴とする
特許請求の範囲第１項記載の難燃性エチレン系樹脂組成
物。(2) Claim 1, characterized in that the ethylene copolymer resin is composed of one or more selected from the group of ethylene ethyl acrylate copolymer or ethylene, vinyl acetate copolymer. flame-retardant ethylene resin composition.
、マレイン酸、無水マレイン酸、フマル酸、メタクリル
酸の内何れか１種からなることを特徴とする特許請求の
範囲第１項記載の難燃性エチレン系樹脂組成物。(3) The problem described in claim 1, characterized in that the unsaturated carboxylic acid or its anhydride consists of any one of acrylic acid, maleic acid, maleic anhydride, fumaric acid, and methacrylic acid. Flammable ethylene resin composition.
ニウムの何れか１種からなることを特徴と、する特許請
求の範囲第１項記載の難燃性エチレン系樹脂組成物。(4) The flame-retardant ethylene-based resin composition according to claim 1, wherein the metal anhydride is composed of one of magnesium hydroxide and aluminum hydroxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30146386A JPS63154760A (en) | 1986-12-19 | 1986-12-19 | Fire-retardant ethylenic resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30146386A JPS63154760A (en) | 1986-12-19 | 1986-12-19 | Fire-retardant ethylenic resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63154760A true JPS63154760A (en) | 1988-06-28 |
Family
ID=17897199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30146386A Pending JPS63154760A (en) | 1986-12-19 | 1986-12-19 | Fire-retardant ethylenic resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63154760A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5497744A (en) * | 1993-11-29 | 1996-03-12 | Toyota Jidosha Kabushiki Kaisha | Fuel injector with an integrated spark plug for a direct injection type engine |
| US6755175B1 (en) * | 1999-10-18 | 2004-06-29 | Orbital Engine Company (Australia) Pty Limited | Direct injection of fuels in internal combustion engines |
| JP2008208759A (en) * | 2007-02-26 | 2008-09-11 | Tomoki Yamazaki | Spark injector plug |
-
1986
- 1986-12-19 JP JP30146386A patent/JPS63154760A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5497744A (en) * | 1993-11-29 | 1996-03-12 | Toyota Jidosha Kabushiki Kaisha | Fuel injector with an integrated spark plug for a direct injection type engine |
| US6755175B1 (en) * | 1999-10-18 | 2004-06-29 | Orbital Engine Company (Australia) Pty Limited | Direct injection of fuels in internal combustion engines |
| JP2008208759A (en) * | 2007-02-26 | 2008-09-11 | Tomoki Yamazaki | Spark injector plug |
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