JPS627230B2 - - Google Patents
Info
- Publication number
- JPS627230B2 JPS627230B2 JP56183675A JP18367581A JPS627230B2 JP S627230 B2 JPS627230 B2 JP S627230B2 JP 56183675 A JP56183675 A JP 56183675A JP 18367581 A JP18367581 A JP 18367581A JP S627230 B2 JPS627230 B2 JP S627230B2
- Authority
- JP
- Japan
- Prior art keywords
- acrylate
- meth
- weight
- butyl
- butyl methacrylate
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 12
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003973 paint Substances 0.000 claims description 7
- 229920002678 cellulose Polymers 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 3
- -1 2-ethylhexyl Chemical group 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 claims description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 3
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000004923 Acrylic lacquer Substances 0.000 description 2
- 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
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000006223 plastic coating Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明はアクリルラツカーに関し、さらに詳細
には、特定量のｔ−ブチルメタクリレートを用い
て得られる特定の共重合体を必須の成分として用
いることから成る、耐摩耗性および耐アルコール
性にすぐれたプラスチツク塗装用ラツカーに関す
る。
繊維素系化合物を含むラツカー型塗料は乾燥性
および耐溶剤性などの性能面に加えて使用面での
簡便さから、その用途も多方面に亘つている。
就中、アクリル樹脂と繊維素系化合物とから成
る塗料は、プラスチツク成型品の塗装に多量に使
用されている。
しかしながら、従来のプラスチツク塗装物は梱
包時のスリ傷や素地の露出などの、いわゆる耐摩
耗性の点で十分ではない、というのが実状であ
る。
しかるに、本発明者らは上述した如き従来技術
における種々の欠点の存在に鑑みて鋭意検討した
結果、ｔ−ブチルメタクリレート(1)の５〜95重量
％と、(2)このｔ−ブチルメタクリレート(1)と共重
合しうる、後記する如き特定の単量体の５〜95重
量％とを重合させて得られる、数平均分子量が
5000〜50000であつて、かつ、ガラス転移点が60
〜95℃なる共重合物が、さらには該共重合体に対
し、公知慣用の顔料、塗料用添加剤および／また
は繊維素系化合物を含有せしめたものをプラスチ
ツク成型品に塗装されたさいに、すぐれた耐摩耗
性および耐アルコール性の塗膜を与えることを見
出して、本発明を完成させるに到つた。
ここにおいてｔ−ブチルメタクリレート(1)と共
重合可能な単量体(2)とは、メチル（メタ）アクリ
レート、エチル（メタ）アクリレート、ｎ−ブチ
ル（メタ）アクリレート、２−エチルヘキシル
（メタ）アクリレート、ラウリル（メタ）アクリ
レート、ステアリル（メタ）アクリレート、ｉ−
ブチルアクリレート、トリデシルメタクリレート
またはスチレンの都合15の化合物を指称するもの
であり、これらは単独で、あるいは二種以上を混
合して用いることができる。
そして、前記ｔ−ブチルメタクリレート(1)の使
用量は得られる共重合物中に５〜95重量％、好ま
しくは10〜90重量％であり、他方、前記した共重
合性単量体(2)の使用量は５〜95重量％、好ましく
は10〜90重量％である。
このｔ−ブチルメタクリレートの使用量が５重
量％未満では耐摩耗性および耐アルコール性の点
で十分ではなく、逆に、95重量％を超えるときは
クラツク発生の虞れがあり、いずれも好ましくな
い。
かかる単量体組成をもつて得られる共重合物
は、まずそのガラス転移点が60〜95℃なる範囲内
であることが必要であり、単量体の選択も、こう
した点からなされるべきであり、60℃よりも低い
ものでは耐摩耗性の点で十分ではなく、逆に95℃
よりも高いものではクラツク発生が見られ易くな
るので、いずれも好ましくない。
そして、当該共重合物はその数平均分子量が
5000〜50000なる範囲内にあることも必要であ
り、好ましくは15000〜35000なる範囲である。
5000よりも低分子量のものでは耐摩耗性の点で
十分ではなく、逆に50000よりも高分子量のもの
ではスプレー作業性の点で十分なものが得難くな
るので、いずれも好ましくない。
当該共重合物を得るには公知慣用の重合法が採
用できるが、好ましくは溶液重合法が適当であ
り、前記した如き単量体を用い、溶剤としてたと
えばトルエンもしくはキシレンの如き芳香族炭化
水素、酢酸エチルもしくは酢酸ブチルの如きエス
テル類、メチルエチルケトンもしくはメチルイソ
ブチルケトンの如きケトン類またはｎ−ブタノー
ルもしくはｉ−ブタノールの如きアルコール類を
用い、アゾビスイソブチロニトリル（AIBN）、
ベンゾイルパーオキサイド（BPO）、ｔ−ブチル
パーベンゾエート（TBPB）またはｔ−ブチルパ
ーオクトエート（TBPO）などの如き公知慣用の
ラジカル発生剤の存在下に重合させるのがよい。
かくして得られる共重合物は適当なシンナーで
希釈してそのままクリヤー塗料として使用するこ
ともできるし、さらに必要に応じて顔料、塗料用
添加剤および／または繊維素系化合物を併用した
形でラツカーとして使用することもできる。
ここにおいて、耐シンナー性、乾燥性、硬度お
よび可撓性をレベルアツプさせる目的のためには
硝化綿やセルローズ・アセテート・ブチレートの
如き繊維素系化合物を、また機械的物性のレベル
アツプのためには可塑剤またはポリエステル樹脂
を、さらにハジキ防止、耐候性およびレベリング
性を一層向上せしめるためには消泡剤、レベリン
グ剤、紫外線吸収剤または酸化防止剤などの如き
公知慣用の塗料用添加剤を慣用量で使用すればよ
い。
また、塗装方法としてはハケ塗り、スプレー塗
装またはロール塗装などの如き公知慣用の方法が
採用できる。
本発明のラツカーは耐摩耗性および耐アルコー
ル性に特にすぐれたものであるが、かかる効果の
現出の理由については明確ではないが、単量体と
して用いられるｔ−ブチルメタクリレートに負う
ものであろうと思われる。
次に、本発明を実施例および比較例により具体
例に説明するが、以下において特に断りのない限
り、「部」は「重量部」を意味するものとする。
実施例１〜３および比較例１〜５
撹拌装置、不活性ガス導入口、温度計および冷
却器を付した４ツ口フラスコに、トルエン500ｇ
およびｎ−ブタノール500ｇを仕込んで昇温して
100℃になつた時点で、第１表に示されたような
混合物を各４時間を要して滴下させ、その後も同
温度に10時間保持して重合を行ない、目的とする
共重合物を得た。
ここに得られた各種の共重合物の数平均分子量
およびガラス転移点について測定した処を、同表
にまとめて示す。
次いで、これら各共重合物の100部に対して、
アルミペースト（不揮発分65重量％）の10部を各
別に加えて分散させたのち、酢酸エチル／ｎ−ブ
タノール／ブチルセロソルブ＝40／40／20（重量
比）なるシンナーで希釈して、ラツカーを調製し
た。
しかるのち、これをエアースプレーで膜厚が15
μとなるようにポリスチレン板に塗装し、60℃で
30分間焼付けを行なつた。
その後、常温に３日間放置して得られたそれぞ
れの塗膜について性能の評価を行なつた処を、同
表にまとめて示す。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an acrylic lacquer, and more particularly to an acrylic lacquer with abrasion resistance comprising the use as an essential component of a specific copolymer obtained with a specific amount of t-butyl methacrylate. and a lacquer for plastic coatings with excellent alcohol resistance. Lutker-type paints containing cellulose compounds have a wide range of uses because of their performance, such as drying properties and solvent resistance, as well as their ease of use. In particular, paints made of acrylic resins and cellulose compounds are widely used for coating plastic molded products. However, the reality is that conventional plastic coatings do not have sufficient wear resistance, such as scratches during packaging and exposure of the base material. However, as a result of intensive studies in view of the various drawbacks in the prior art as described above, the present inventors found that 5 to 95% by weight of t-butyl methacrylate (1) and (2) this t-butyl methacrylate ( The number average molecular weight obtained by polymerizing 5 to 95% by weight of a specific monomer as described below that can be copolymerized with 1).
5000 to 50000 and the glass transition point is 60
When a copolymer with a temperature of ~95°C and a copolymer containing a known and commonly used pigment, paint additive, and/or cellulose compound are applied to a plastic molded product, The present invention was completed based on the discovery that a coating film with excellent abrasion resistance and alcohol resistance can be provided. Here, the monomer (2) copolymerizable with t-butyl methacrylate (1) refers to methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate. , lauryl (meth)acrylate, stearyl (meth)acrylate, i-
It refers to 15 compounds such as butyl acrylate, tridecyl methacrylate, and styrene, and these can be used alone or in a mixture of two or more. The amount of the t-butyl methacrylate (1) used is 5 to 95% by weight, preferably 10 to 90% by weight in the resulting copolymer, while the amount of the above-mentioned copolymerizable monomer (2) The amount used is 5 to 95% by weight, preferably 10 to 90% by weight. If the amount of t-butyl methacrylate used is less than 5% by weight, the wear resistance and alcohol resistance will not be sufficient, whereas if it exceeds 95% by weight, there is a risk of cracks occurring, both of which are undesirable. . The copolymer obtained with such a monomer composition must first have a glass transition point within the range of 60 to 95°C, and the selection of monomers should also be made from this point of view. However, if the temperature is lower than 60℃, the wear resistance is not sufficient;
Anything higher than this is unfavorable because cracks are more likely to occur. The copolymer has a number average molecular weight of
It is also necessary that the number is in the range of 5,000 to 50,000, preferably in the range of 15,000 to 35,000. If the molecular weight is lower than 5,000, the abrasion resistance will not be sufficient, and if the molecular weight is higher than 50,000, it will be difficult to obtain sufficient spray workability, so both are not preferred. Although known and commonly used polymerization methods can be used to obtain the copolymer, a solution polymerization method is preferably used, using monomers such as those described above, and an aromatic hydrocarbon such as toluene or xylene as a solvent. Using esters such as ethyl acetate or butyl acetate, ketones such as methyl ethyl ketone or methyl isobutyl ketone, or alcohols such as n-butanol or i-butanol, azobisisobutyronitrile (AIBN),
The polymerization is preferably carried out in the presence of a known and commonly used radical generator such as benzoyl peroxide (BPO), t-butyl perbenzoate (TBPB) or t-butyl peroctoate (TBPO). The copolymer thus obtained can be diluted with an appropriate thinner and used as a clear paint, or it can be used as a lacquer in combination with pigments, paint additives, and/or cellulose compounds if necessary. You can also use Here, cellulose compounds such as nitrified cotton and cellulose acetate butyrate are used to increase the level of thinner resistance, drying properties, hardness and flexibility, and to increase the level of mechanical properties. Plasticizers or polyester resins are used, and in order to further improve anti-cissing properties, weather resistance and leveling properties, commonly known paint additives such as antifoaming agents, leveling agents, ultraviolet absorbers or antioxidants are used. It should be used in quantity. Further, as the coating method, known and commonly used methods such as brush coating, spray coating, or roll coating can be adopted. The lacquer of the present invention has particularly excellent abrasion resistance and alcohol resistance, but the reason for this effect is not clear, but it may be due to the t-butyl methacrylate used as a monomer. I think I'm deaf. Next, the present invention will be explained in detail with reference to Examples and Comparative Examples. In the following, "parts" mean "parts by weight" unless otherwise specified. Examples 1 to 3 and Comparative Examples 1 to 5 500 g of toluene was placed in a 4-necked flask equipped with a stirrer, an inert gas inlet, a thermometer, and a condenser.
Add 500g of n-butanol and raise the temperature.
When the temperature reached 100°C, the mixture shown in Table 1 was added dropwise over a period of 4 hours, and the same temperature was then maintained for 10 hours to carry out polymerization to produce the desired copolymer. Obtained. The number average molecular weight and glass transition point of the various copolymers obtained here are summarized in the same table. Next, for 100 parts of each of these copolymers,
Add 10 parts of aluminum paste (non-volatile content 65% by weight) to each and disperse them, then dilute with a thinner consisting of ethyl acetate/n-butanol/butyl cellosolve = 40/40/20 (weight ratio) to prepare a lacquer. did. Afterwards, air spray this to a film thickness of 15 mm.
Painted on a polystyrene plate so that it was μ, and heated at 60℃.
Baking was carried out for 30 minutes. Thereafter, the performance of each coating film obtained by leaving it at room temperature for 3 days was evaluated, and the results are summarized in the same table. 【table】
Claims (1)
と、(2)メチル（メタ）アクリレート、エチル（メ
タ）アクリレート、ｎ−ブチル（メタ）アクリレ
ート、２−エチルヘキシル（メタ）アクリレー
ト、ラウリル（メタ）アクリレート、ステアリル
（メタ）アクリレート、ｉ−ブチルアクリレー
ト、トリデシルメタクリレートおよびスチレンよ
りなる群から選ばれる少なくとも１種の、上記ｔ
−ブチルメタクリレート(1)と共重合可能な単量体
の５〜95重量％とを合計して100重量％となるよ
うに重合させて得られる、数平均分子量が5000〜
50000で、かつガラス転移点が60〜95℃なる共重
合体を必須の成分として、さらに必要に応じて顔
料、塗料用添加剤および／または繊維素系化合物
を用いることを特徴とする、アクリルラツカー。1 (1) 5-95% by weight of t-butyl methacrylate
and (2) methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, i-butyl acrylate, At least one of the above t selected from the group consisting of tridecyl methacrylate and styrene.
- A number average molecular weight of 5000 to 5000, obtained by polymerizing butyl methacrylate (1) and 5 to 95% by weight of a copolymerizable monomer so that the total amount is 100% by weight.
50,000 and a glass transition point of 60 to 95°C as an essential component, and further contains pigments, paint additives, and/or cellulose compounds as necessary. car.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18367581A JPS5887160A (en) | 1981-11-18 | 1981-11-18 | Acrylic lacquer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18367581A JPS5887160A (en) | 1981-11-18 | 1981-11-18 | Acrylic lacquer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5887160A JPS5887160A (en) | 1983-05-24 |
| JPS627230B2 true JPS627230B2 (en) | 1987-02-16 |
Family
ID=16139951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18367581A Granted JPS5887160A (en) | 1981-11-18 | 1981-11-18 | Acrylic lacquer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5887160A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02134037U (en) * | 1989-04-17 | 1990-11-07 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4676656A (en) * | 1985-01-25 | 1987-06-30 | Syntex (U.S.A.) Inc. | Fluid handling apparatus and method |
| JPH0267380A (en) * | 1988-09-01 | 1990-03-07 | Nippon Shokubai Kagaku Kogyo Co Ltd | Acrylic lacquer composition |
| US8198377B2 (en) * | 2007-07-10 | 2012-06-12 | Mitsubishi Rayon Co., Ltd. | Thermal fluidity modifier for powder coating material, method for producing the same, and powder coating material |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS48101425A (en) * | 1972-04-05 | 1973-12-20 | ||
| JPS51122131A (en) * | 1975-04-18 | 1976-10-26 | Nagoya Yukagaku Kogyo Kk | Surface coating compound for plastics |
| JPS52153881A (en) * | 1976-06-17 | 1977-12-21 | Matsushita Electric Ind Co Ltd | Compositions for antistatic use |
| JPS559614A (en) * | 1978-07-06 | 1980-01-23 | Asahi Chem Ind Co Ltd | Acrylic resin having improved solvent resistance |
| JPS55151637A (en) * | 1979-05-15 | 1980-11-26 | Chiyou Lsi Gijutsu Kenkyu Kumiai | Radiation sensitive material and film forming method |
-
1981
- 1981-11-18 JP JP18367581A patent/JPS5887160A/en active Granted
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS48101425A (en) * | 1972-04-05 | 1973-12-20 | ||
| JPS51122131A (en) * | 1975-04-18 | 1976-10-26 | Nagoya Yukagaku Kogyo Kk | Surface coating compound for plastics |
| JPS52153881A (en) * | 1976-06-17 | 1977-12-21 | Matsushita Electric Ind Co Ltd | Compositions for antistatic use |
| JPS559614A (en) * | 1978-07-06 | 1980-01-23 | Asahi Chem Ind Co Ltd | Acrylic resin having improved solvent resistance |
| JPS55151637A (en) * | 1979-05-15 | 1980-11-26 | Chiyou Lsi Gijutsu Kenkyu Kumiai | Radiation sensitive material and film forming method |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02134037U (en) * | 1989-04-17 | 1990-11-07 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5887160A (en) | 1983-05-24 |
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