JPH0358378B2 - - Google Patents
Info
- Publication number
- JPH0358378B2 JPH0358378B2 JP13634883A JP13634883A JPH0358378B2 JP H0358378 B2 JPH0358378 B2 JP H0358378B2 JP 13634883 A JP13634883 A JP 13634883A JP 13634883 A JP13634883 A JP 13634883A JP H0358378 B2 JPH0358378 B2 JP H0358378B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- epoxidized
- resins
- fatty acid
- flame
- 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
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- 239000004014 plasticizer Substances 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- -1 fatty acid ester Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003063 flame retardant Substances 0.000 description 10
- 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 9
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000002383 tung oil Substances 0.000 description 3
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- PYOALRBVGLCADY-UHFFFAOYSA-N bis(4-bromophenyl) hydrogen phosphate Chemical compound C=1C=C(Br)C=CC=1OP(=O)(O)OC1=CC=C(Br)C=C1 PYOALRBVGLCADY-UHFFFAOYSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明はプラスチツクの難撚化すると同時に可
塑性を付与するために使用される難撚性可塑剤に
関する。
フエノール樹脂、エポキシ樹脂、不飽和ポリエ
ステル樹脂等の熱硬化性樹脂は各種の用途に使用
され、特に電気、電子部品用途においては電気的
特性、耐湿性、難燃性、可塑性を同時に要する領
域が多い。例えば積層板（プリント配線基板を含
む）にこれらの樹脂を使用する場合、積層板の加
工工程の自動化、低温加工性、曲面加工性等の要
求に対応するための可塑剤としてリン酸エステ
ル、長鎖アルキルフエニルグリシジルエーテル、
桐油等が使用されており、低温パンチング、スル
ーホールのホール間短縮等の要求に対応するため
可塑剤の使用量の増大が見られる。
一方、積層板のうち、高電圧部に使用するもの
については難燃化が必須要件となつている。その
ため樹脂に難燃剤を添加しなければならないが、
可塑剤量の増大は難燃性を困難にし、また、難燃
剤の多量の使用は物性面での劣化が大きい。本発
明者らは、単一成分をもつて樹脂にバランスの取
れた難燃性と可塑性とを同時に付与することがで
きる難燃性可塑剤を開発し、上記の欠点を解消す
ることに成功した。すなわち、エポキシ化油また
はエポキシ化高級脂肪酸エステルと、下記一般式
（）で示される化合物とを反応させて得られる
リン含有化合物を主成分とすることを特徴とする
熱硬化性樹脂用難燃性可塑剤である。
〔式中、R1およびR2は、フエニル基、ハロゲン
化フエニル基または
The present invention relates to a twist-resistant plasticizer that is used to make plastics more difficult to twist and at the same time impart plasticity to them. Thermosetting resins such as phenolic resins, epoxy resins, and unsaturated polyester resins are used in a variety of applications, especially in electrical and electronic component applications, which often require electrical properties, moisture resistance, flame retardancy, and plasticity at the same time. . For example, when using these resins for laminates (including printed wiring boards), phosphate esters and long resins are used as plasticizers to meet requirements such as automation of the laminate processing process, low-temperature processability, and curved surface processability. chain alkyl phenyl glycidyl ether,
Tung oil and the like are used, and the amount of plasticizer used is increasing to meet the demands for low-temperature punching, shortening the distance between through holes, etc. On the other hand, flame retardancy is an essential requirement for laminates used in high voltage parts. Therefore, flame retardants must be added to the resin,
An increase in the amount of plasticizer makes flame retardancy difficult, and the use of a large amount of flame retardant significantly deteriorates physical properties. The present inventors have succeeded in solving the above-mentioned drawbacks by developing a flame-retardant plasticizer that can simultaneously impart well-balanced flame retardancy and plasticity to resins using a single component. . That is, a flame retardant for thermosetting resin characterized in that the main component is a phosphorus-containing compound obtained by reacting an epoxidized oil or an epoxidized higher fatty acid ester with a compound represented by the following general formula (). It is a plasticizer. [In the formula, R 1 and R 2 are phenyl group, halogenated phenyl group, or
【式】を示す。 R3は炭素数１〜12のアルキル基を示す。 Ａは、[Formula] is shown. R 3 represents an alkyl group having 1 to 12 carbon atoms. A is
【式】【formula】
【式】 または【formula】 or
【式】を示す。
Ｘは、臭素原子を示す。
ｎは０〜５の整数を示す。〕
本発明において用いられるエポキシ化油として
は、例えばエポキシ化大豆油、エポキシ化桐油、
エポキシ化水添ヒマシ油、エポキシ化亜麻仁油等
が挙げられる。またエポキシ化高級脂肪酸エステ
ルとしては、例えばエポキシ化大豆油脂肪酸メチ
ル、エポキシ化亜麻仁油脂酸エチル、エポキシ化
桐油脂肪酸メチル等が挙げられる。一般式（）
で示される化合物（以下化合物（）という）と
しては、
例えば[Formula] is shown. X represents a bromine atom. n represents an integer of 0 to 5. ] Examples of the epoxidized oil used in the present invention include epoxidized soybean oil, epoxidized tung oil,
Examples include epoxidized hydrogenated castor oil and epoxidized linseed oil. Examples of the epoxidized higher fatty acid ester include epoxidized methyl soybean oil fatty acid, epoxidized ethyl linseed oil fatty acid, and epoxidized methyl tung oil fatty acid. General formula ()
As a compound represented by (hereinafter referred to as compound ()), for example,
【式】等のリン
酸モノハロデートとHO−Ａ−OHとを脱HCl剤
の存在下で公知の方法または加熱脱HCl反応させ
て得られるものが挙げられる。（R1、R2およびＡ
は上記と同じ）
リン酸モノハロデートとしては、例えばジ（フ
エニル）リン酸モノクロリデート、
ジ（モノブロモフエニル）リン酸モノクロリデ
ート、
ジ（ジモノブロモフエニル）リン酸モノクロリ
デート、
等が挙げられる。
HO−Ａ−OHとしては、例えば、
(a) ヒドロキノン、ビス（４−ヒドロキシフエニ
ル）メタン、２，２−ビス（４−ヒドロキシフ
エニル）プロパン
(b) (a)の化合物において、フエニル基の水素がハ
ロゲン原子で置換されたもの等が挙げられる。
エポキシ化油またはエポキシ化高級脂肪酸エス
テルと、化合物（）とを反応させる場合、二成
分の合計量の15％以下のカチオン活性剤の存在下
50〜130℃で行う。反応時間は、反応温度にもよ
るが、通常３〜15時間である。反応割合は、エポ
キシ化油またはエポキシ化公衆脂肪酸エステルの
エポキシ基１個当り、化合物（）１モルが適当
である。
カチオン活性剤としては、例えばＮ−オクチル
N.N.Nトリメチルアンモニウムクロライド、Ｎ
−ラウリル−N.N.Nトリメチルアンモニウムブ
ロマイド、N.N−ジステアリル−N.N−ジメチ
ルアンモニウムクロライド、N.N−ジステアリ
ルN.N−ジメチルアンモニウムラウレート、Ｎ
−オクチルフエノキシエチルN.N.Nトリメチル
アンモニウムクロライド、Ｎ−ラウリル−Ｎ−ベ
ンジル−N.N−ジメチルアンモニウムクロライ
ド、Ｎ−オクチル−N.N.N−トリエチルアンモ
ニウムブロマイド等が挙げられる。
本発明は上記のように、二成分を反応させて得
られるリン含有化合物を難燃性可塑剤とするもの
である。
本発明の難燃性可塑剤を適用する樹脂は、例え
ば熱硬化性樹脂、例えば不飽和ポリエステル樹
脂、エポキシ樹脂、フエノール樹脂、メラミン樹
脂等の積層板製造用樹脂に有用である。
本発明の難燃性可塑剤は、樹脂100部重量部に
対し５〜100重量部の割合で使用するのが好まし
い。
本発明に従つて得られる難燃性可塑剤を、とり
わけ積層板の製造に用いた場合、難燃性および可
塑性に優れた積層板が得られる。
以下、本発明の実施例を記載する。
実施例 １
エポキシ化油またはエポキシ化高級脂肪酸エス
テルに化合物（）を加え、これにカチオン活性
剤を加え、窒素ガスを通しつつ、温度100〜130℃
で５時間反応させた。
反応終了後、リン含有化合物を得た。
同様にして、各種リン含有化合物を得た。
それらを第１表に示す。
なお、リン含有化合物の性状における（ ）の
数字は理論値である。Examples include those obtained by subjecting a phosphoric acid monohalodate such as [Formula] and HO-A-OH to a de-HCl reaction in the presence of a de-HCl agent by a known method or by heating. (R 1 , R 2 and A
(same as above) Monohalodate phosphates include, for example, monochloridate di(phenyl) phosphate, monochloridate di(monobromophenyl) phosphate, monochloridate di(dimonobromophenyl) phosphate, etc. As HO-A-OH, for example, (a) hydroquinone, bis(4-hydroxyphenyl)methane, 2,2-bis(4-hydroxyphenyl)propane (b) in the compound (a), a phenyl group Examples include those in which hydrogen is replaced with a halogen atom. When reacting epoxidized oil or epoxidized higher fatty acid ester with compound (), in the presence of a cationic activator of 15% or less of the total amount of the two components.
Perform at 50-130℃. The reaction time is usually 3 to 15 hours, although it depends on the reaction temperature. The appropriate reaction ratio is 1 mole of compound () per epoxy group of the epoxidized oil or epoxidized public fatty acid ester. As a cationic activator, for example, N-octyl
NNN trimethylammonium chloride, N
-Lauryl-NNN trimethylammonium bromide, NN-distearyl-NN-dimethylammonium chloride, NN-distearylNN-dimethylammonium laurate, N
-Octylphenoxyethyl NNN trimethylammonium chloride, N-lauryl-N-benzyl-NN-dimethylammonium chloride, N-octyl-NNN-triethylammonium bromide, and the like. As described above, the present invention uses a phosphorus-containing compound obtained by reacting two components as a flame-retardant plasticizer. The resin to which the flame-retardant plasticizer of the present invention is applied is useful, for example, as a thermosetting resin, such as an unsaturated polyester resin, an epoxy resin, a phenolic resin, a melamine resin, and other resins for manufacturing laminates. The flame retardant plasticizer of the present invention is preferably used in an amount of 5 to 100 parts by weight per 100 parts by weight of the resin. When the flame-retardant plasticizer obtained according to the invention is used in particular for the production of laminates, laminates with excellent flame retardancy and plasticity are obtained. Examples of the present invention will be described below. Example 1 Compound () is added to epoxidized oil or epoxidized higher fatty acid ester, a cation activator is added thereto, and the temperature is 100 to 130°C while passing nitrogen gas.
The reaction was carried out for 5 hours. After the reaction was completed, a phosphorus-containing compound was obtained. Various phosphorus-containing compounds were obtained in the same manner. They are shown in Table 1. Note that the numbers in parentheses in the properties of phosphorus-containing compounds are theoretical values.
【表】【table】
【表】
実施例 ２
フエノール200ｇ、メタクレゾール228ｇ、37％
ホルマリン800ｇ、トリエチルアミン８ｇを60〜
70℃で６時間反応させ、減圧下で脱水した後、こ
の脱水物に実施例１で得た各種リン含有化合物を
難燃性可塑剤として400ｇ加え、メタノールで希
釈して樹脂分50％のワニスを得た。比較例とし
て、難燃性可塑剤無添加の樹脂分50％のワニスを
同様にして得た。
それらをそれぞれクラフト紙に含浸させ、樹脂
含量50％のプリプレグを製造した。
このようにして得たプリプレグをそれぞれ８枚
ずつ重ね、プレス１（160℃±５℃、150Kg／cm230
分）厚さ1.6mmの積層板を得た。それらの積層板
の諸特性を第２表に示す。[Table] Example 2 Phenol 200g, metacresol 228g, 37%
800g formalin, 8g triethylamine 60~
After reacting at 70°C for 6 hours and dehydrating under reduced pressure, 400g of various phosphorus-containing compounds obtained in Example 1 were added as a flame-retardant plasticizer to the dehydrated product, and diluted with methanol to make a varnish with a resin content of 50%. I got it. As a comparative example, a varnish with a resin content of 50% and no flame retardant plasticizer was obtained in the same manner. Each of these was impregnated into kraft paper to produce prepreg with a resin content of 50%. The prepregs obtained in this way were stacked 8 sheets each and pressed in press 1 (160℃±5℃, 150Kg/cm 2 30
) A laminate with a thickness of 1.6 mm was obtained. Table 2 shows the properties of those laminates.
Claims (1)
ステルと、下記一般式（）で示される化合物と
を反応させて得られるリン含有化合物を主成分と
することを特徴とする熱硬化性樹脂用難撚性可塑
剤。 〔式中、R1およびR2は、フエニル基、ハロゲン
化フエニル基または 【式】を示す。 R3は炭素数１〜12のアルキル基を示す。 Ａは、【式】 【式】 または【式】を示す。 Ｘは、臭素原子を示す。 ｎは０〜５の整数を示す。〕[Claims] 1. A thermosetting product characterized by containing as a main component a phosphorus-containing compound obtained by reacting an epoxidized oil or an epoxidized higher fatty acid ester with a compound represented by the following general formula (). A twist-resistant plasticizer for resins. [In the formula, R 1 and R 2 represent a phenyl group, a halogenated phenyl group, or [Formula]]. R 3 represents an alkyl group having 1 to 12 carbon atoms. A represents [Formula] [Formula] or [Formula]. X represents a bromine atom. n represents an integer of 0 to 5. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13634883A JPS6028440A (en) | 1983-07-25 | 1983-07-25 | flame retardant plasticizer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13634883A JPS6028440A (en) | 1983-07-25 | 1983-07-25 | flame retardant plasticizer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6028440A JPS6028440A (en) | 1985-02-13 |
| JPH0358378B2 true JPH0358378B2 (en) | 1991-09-05 |
Family
ID=15173089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13634883A Granted JPS6028440A (en) | 1983-07-25 | 1983-07-25 | flame retardant plasticizer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6028440A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118373950B (en) * | 2024-06-24 | 2024-09-20 | 苏州艾特斯环保设备有限公司 | Preparation method and application of anti-aging antistatic phenolic resin |
-
1983
- 1983-07-25 JP JP13634883A patent/JPS6028440A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6028440A (en) | 1985-02-13 |
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