JPH0692463B2 - Copolymer for coating - Google Patents

Copolymer for coating

Info

Publication number
JPH0692463B2
JPH0692463B2 JP58087590A JP8759083A JPH0692463B2 JP H0692463 B2 JPH0692463 B2 JP H0692463B2 JP 58087590 A JP58087590 A JP 58087590A JP 8759083 A JP8759083 A JP 8759083A JP H0692463 B2 JPH0692463 B2 JP H0692463B2
Authority
JP
Japan
Prior art keywords
parts
copolymer
weight
acid
polymerizable monomer
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 - Lifetime
Application number
JP58087590A
Other languages
Japanese (ja)
Other versions
JPS59213713A (en
Inventor
正一郎 竹沢
親 田垣内
博夫 田中
陽一 村上
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DIC Corp
Original Assignee
Dainippon Ink and Chemicals Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dainippon Ink and Chemicals Co Ltd filed Critical Dainippon Ink and Chemicals Co Ltd
Priority to JP58087590A priority Critical patent/JPH0692463B2/en
Publication of JPS59213713A publication Critical patent/JPS59213713A/en
Publication of JPH0692463B2 publication Critical patent/JPH0692463B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Description

【発明の詳細な説明】 本発明は新規にして有用なる被覆用共重合体に関するも
のであり、さらに詳細には、長鎖の炭化水素基を含有す
る特定の重合性単量体と、スチレンとを必須の構成単位
として含んで成る共重合体に関するものである。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel and useful coating copolymer, more specifically, a specific polymerizable monomer containing a long-chain hydrocarbon group and styrene. The present invention relates to a copolymer containing as an essential constituent unit.

被覆用樹脂としては、現在、アクリル系樹脂が広く使用
されてはいるけれども、かかる系統の樹脂を用いたいわ
ゆるアクリル系塗料は耐候性および耐汚染性などがすぐ
れている一方で、塗装作業性、顔料分散性および肉持ち
感に劣るという欠点を有している。
As the coating resin, although acrylic resins are widely used at present, so-called acrylic paints using such resins are excellent in weather resistance and stain resistance, while coating workability, It has a drawback that it is inferior in pigment dispersibility and a feeling of longevity.

そこで、これらの欠点を解消せしめるという目的でアル
キド樹脂による変性やブレンドによる変性などの検討も
なされてきている。
Therefore, for the purpose of eliminating these drawbacks, modification with an alkyd resin or modification with a blend has been studied.

本発明者らも、こうしたアクリル系樹脂の欠点を解消す
べく鋭意検討を重ねた結果、特定の長鎖炭化水素基をも
った重合性単量体とスチレンとを特定の範囲で、必要に
よりさらに他の共重合性単量体をも共重合せしめること
から成る、被覆用として有用なる共重合体を見出して、
本発明を完成させるに到った。
The inventors of the present invention also conducted extensive studies to eliminate the drawbacks of the acrylic resin, and as a result, a polymerizable monomer having a specific long-chain hydrocarbon group and styrene in a specific range were further added if necessary. Finding a copolymer useful for coating, which consists of copolymerizing other copolymerizable monomers,
The present invention has been completed.

すなわち、本発明は一般式 で示される重合性単量体の20〜90重量%と、スチレンの
80〜10重量%と、その他の共重合性単量体の0〜60重量
%とを構成単位として含んで成る被覆用共重合体を提供
するものである。
That is, the present invention has the general formula 20 to 90% by weight of the polymerizable monomer represented by
It is intended to provide a coating copolymer containing 80 to 10% by weight and 0 to 60% by weight of other copolymerizable monomer as a constitutional unit.

本発明の共重合体の必須構成単位としての前掲一般式
〔I〕で示される重合性単量体としては、たとえば次の
ようにして得られるものである。
The polymerizable monomer represented by the above general formula [I] as an essential constituent unit of the copolymer of the present invention is obtained, for example, as follows.

C8〜C21なる脂肪酸類とC2〜C4なるモノエポキシド類と
を付加反応せしめ、次いでこれにC4〜C8なる重合性不飽
和結合を有する酸無水物類を付加反応せしめたのち、さ
らにC2〜C4なるモノエポキシド類を反応せしめて重合性
単量体が得られるが、〔I〕式で示される当該構成単位
を共重合体に導入せしめるに当って使用できる上記した
C8〜C21なる脂肪酸類として代表的なものには大豆油、
トール油、あまに油、サフラワー油、ひまし油、脱水ひ
まし油、やし油、支那桐油もしくは米糖油などの如き天
然油脂類から得られる脂肪酸類;「パモリン(PAMOLY
N)200および300」(米国ハーキュレス社製品)、「ハ
イジエン」〔綜研化学(株)製品〕もしくは「バーサテ
ィック酸」(オランダ国シェル社製品)などの如き合成
脂肪酸類;またはオクチル酸、ラウリン酸もしくはステ
アリン酸などの如き飽和脂肪酸があるし、また使用でき
る前記モノエポキシド類の代表例としてはエチレンオキ
シド、プロピレンオキシドまたは1,4−ブチレンオキシ
ドなどが挙げられるし、さらに使用できる前記した重合
性不飽和結合を有する酸無水物(以下、これを不飽和酸
無水物という。)としては無水マレイン酸、無水イタコ
ン酸またはテトラヒドロ無水フタル酸などが代表的なも
のである。
After the C 8 to C 21 fatty acids and the C 2 to C 4 monoepoxides are subjected to an addition reaction, and then the C 4 to C 8 acid anhydrides having a polymerizable unsaturated bond are subjected to an addition reaction. Further, a C 2 -C 4 monoepoxide is reacted to obtain a polymerizable monomer, which can be used in introducing the constituent unit represented by the formula [I] into the copolymer.
Typical fatty acids such as C 8 to C 21 are soybean oil,
Fatty acids derived from natural fats and oils such as tall oil, linseed oil, safflower oil, castor oil, dehydrated castor oil, coconut oil, Chinese tung oil or rice sugar oil; "PAMOLY
N) 200 and 300 "(product of Hercules Inc., USA)," Hidiene "[product of Soken Chemical Industry Co., Ltd.] or" versatic acid "(product of Shell Co., Netherlands); or octyl acid, lauric acid Alternatively, there are saturated fatty acids such as stearic acid, and typical examples of the monoepoxides that can be used include ethylene oxide, propylene oxide, and 1,4-butylene oxide. Typical examples of the acid anhydride having a bond (hereinafter referred to as unsaturated acid anhydride) include maleic anhydride, itaconic anhydride, tetrahydrophthalic anhydride, and the like.

他方、前記した共重合性単量体として代表的なものを例
示すれば、C1〜C20なる飽和モノアルコールの(メタ)
アクリル酸エステル類、(メタ)アクリル酸、(メタ)
アクリルアミド、(メタ)アクリロニトリル、(β−メ
チル)グリシジル(メタ)アクリレート、β−ヒドロキ
シエチル(メタ)アクリレート、β−ヒドロキシプロピ
ル(メタ)アクリレート、ベンジル(メタノアグリレー
ト、N,N−ジメチルアミノエチル(メタ)アクリレート
もしくはN,N−ジエチルアミノエチル(メタ)アクリレ
ート;C1〜C12なる飽和モノアルコールとマレイン酸、
フマル酸もしくはイタコン酸とのモノないしはジエステ
ル酸;ビニルトルエンまたは酢酸ビニルなどである。
On the other hand, as a typical example of the above-mentioned copolymerizable monomer, C 1 to C 20 of a saturated monoalcohol (meth)
Acrylic esters, (meth) acrylic acid, (meth)
Acrylamide, (meth) acrylonitrile, (β-methyl) glycidyl (meth) acrylate, β-hydroxyethyl (meth) acrylate, β-hydroxypropyl (meth) acrylate, benzyl (methanoacrylate, N, N-dimethylaminoethyl ( (Meth) acrylate or N, N-diethylaminoethyl (meth) acrylate; saturated monoalcohol C 1 to C 12 and maleic acid,
Mono- or diester acids with fumaric acid or itaconic acid; vinyltoluene, vinyl acetate and the like.

ところで、本発明の共重合体を構成する一基本単位であ
る前掲一般式〔I〕で示される重合性単量体は、前述し
たようにして、予めモノマーとして合成しておいてから
他の共重合性単量体、つまり前記スチレンと、必要によ
り用いられる前掲の如き他の共重合性単量体と共重合せ
しめるようにしてもよいし、あるいはスチレンに、さら
に必要に応じて他の共重合性単量体とに前掲した如き不
飽和酸無水物を共重合させたのちに、またはこの共重合
の途中で、C8〜C21なる脂肪酸類とC2〜C4なるモノエポ
キシド類との付加物を反応せしめ、次いでさらにC2〜C4
なるモノエポキシド類を反応せしめるなどして、最終的
に得られる当該共重合体の構成単位として、前掲一般式
〔I〕で示される重合性単量体が導入され含有されてい
ればよい。
By the way, the polymerizable monomer represented by the above-mentioned general formula [I], which is one basic unit constituting the copolymer of the present invention, is previously synthesized as a monomer and then the other copolymer The polymerizable monomer, that is, the above-mentioned styrene, may be copolymerized with other copolymerizable monomer such as those mentioned above, which is optionally used, or with styrene, other copolymerization may be carried out if necessary. After copolymerizing the above-mentioned unsaturated acid anhydride with a polymerizable monomer, or in the course of this copolymerization, C 8 -C 21 fatty acids and C 2 -C 4 monoepoxides the adduct reacted, then further C 2 -C 4
It is sufficient that the polymerizable monomer represented by the above general formula [I] is introduced and contained as a constitutional unit of the copolymer finally obtained by reacting the following monoepoxides.

そして、本発明の共重合性を得るに当っては、前掲一般
式〔I〕なる重合性単量体を20〜90重量%なる範囲で用
い、他方、前記スチレンを80〜10重量%なる範囲で用い
るものではあるが、この重合性単量体の使用量が20重量
%未満であると塗装作業性も肉持ち感も改善し得なくな
るし、逆に90重量%を超えると耐汚染性が低下し易くな
るので好ましくなく、他方、このスチレンの使用量が10
重量%未満である場合には、耐汚染性が低下し易くなる
し、逆に80重量%を超える場合には、どうしても耐候性
が低下するようになるので好ましくない。
In obtaining the copolymerizability of the present invention, the polymerizable monomer represented by the general formula [I] is used in an amount of 20 to 90% by weight, while the styrene is added in an amount of 80 to 10% by weight. However, if the amount of the polymerizable monomer used is less than 20% by weight, neither the coating workability nor the feeling of keeping can be improved, and conversely, if it exceeds 90% by weight, the stain resistance becomes poor. This is not preferable because it tends to decrease.
If it is less than 80% by weight, stain resistance tends to decrease, and if it exceeds 80% by weight, weather resistance tends to decrease, which is not preferable.

また、本発明においては必要に応じて用いてもよい前掲
した如き共重合性単量体は、使用する場合には、60重量
%までてあるのが適当で、この使用量を超えて多くなる
と肉持ち感が悪くなる。
Further, in the present invention, the copolymerizable monomer as described above, which may be optionally used, is appropriately used in an amount of up to 60% by weight. The flesh feeling becomes worse.

本発明の共重合体の数平均分子量としては、得られる塗
料の塗装作業性と、そして塗膜の性能とを損なわないた
めにも、約1000〜30000程度のものが好ましい。
The number average molecular weight of the copolymer of the present invention is preferably about 1000 to 30,000 in order not to impair the coating workability of the resulting coating composition and the performance of the coating film.

また、本発明の共重合体を得るにさいして、共重合の方
法は特に限定されるものではなく、溶液重合や塊状重合
などの種々の公知慣用の重合方法が適用できる。
Further, in obtaining the copolymer of the present invention, the method of copolymerization is not particularly limited, and various known and commonly used polymerization methods such as solution polymerization and bulk polymerization can be applied.

かくして得られる本発明の被覆用共重合体には、アミノ
樹脂、エポキシ樹脂およびイソシアネート・プレポリマ
ーなどの公知慣用の各種添加剤を添加、混せしめること
ができるのは勿論である。
It is needless to say that the coating copolymer of the present invention thus obtained can be added and mixed with various known and commonly used additives such as amino resins, epoxy resins and isocyanate prepolymers.

本発明の被覆用共重合体は、アクリル系樹脂に特有の長
所を何ら損なうこともなく、さらに進んで顔料分散性、
塗装作業性および肉持ち感などの諸性能の向上をも果し
うるという利点を有するものである。
The coating copolymer of the present invention does not impair the advantages peculiar to acrylic resins at all, and further advances pigment dispersibility,
It has an advantage that it can also improve various performances such as coating workability and a feeling of keeping meat.

次に、本発明を参考例、実施例および比較例により具体
的に説明するが、部および%は特に断りのない限り、す
べて重量基準であるものとする。
Next, the present invention will be specifically described with reference to Reference Examples, Examples and Comparative Examples. All parts and% are based on weight unless otherwise specified.

参考例1(脂肪酸類−モノエポキシド類付加反応物の調
製例) 攪拌機および温度計を備えた、10気圧までの圧力に耐え
うる耐圧反応容器に、大豆油脂肪酸280部、プロピレン
オキシド60部および塩化リチウム0.1部を仕込んで密閉
し、130℃で3時間反応せしめて目的とする付加反応生
成物を得た。以下、これを(a−1)と略記するが、こ
のものの酸価は1.0であった。
Reference Example 1 (Preparation example of fatty acid-monoepoxide addition reaction product) In a pressure-resistant reaction vessel equipped with a stirrer and a thermometer and capable of withstanding pressures up to 10 atm, 280 parts of soybean oil fatty acid, 60 parts of propylene oxide and chloride Lithium (0.1 part) was charged, the mixture was sealed, and the reaction was carried out at 130 ° C. for 3 hours to obtain the desired addition reaction product. Hereinafter, this is abbreviated as (a-1), but the acid value of this was 1.0.

参考例2(前掲の一般式〔I〕で示される重合性単量体
の調製例) 参考例1と同様に反応容器にa−1の338部と無水マレ
イン酸の98部とを仕込んで120℃で2時間反応させ、次
いでプロピレンオキシドの60部を加えて130℃で3時間
反応せしめて目的とする重合性単量体を得た。以下、こ
れを(m−1)と略記するが、このものの酸価は2.1で
あった。
Reference Example 2 (Preparation Example of Polymerizable Monomer Shown by General Formula [I]) In the same manner as in Reference Example 1, 338 parts of a-1 and 98 parts of maleic anhydride were charged into a reaction vessel. The reaction was carried out at 0 ° C for 2 hours, then 60 parts of propylene oxide was added and the reaction was carried out at 130 ° C for 3 hours to obtain the objective polymerizable monomer. Hereinafter, this is abbreviated as (m-1), but the acid value of this was 2.1.

参考例3(脂肪酸類−モノエポキシド付加反応物の調製
例) 大豆油脂肪酸の280部の代わりに、やし油脂肪酸の205部
を使用するように変更した以外は、参考例1と同様にし
て、酸価が1.0なる付加反応物を得た。以下、これを
(a−2)と略記する。
Reference Example 3 (Preparation example of fatty acid-monoepoxide addition reaction product) Same as Reference Example 1 except that 205 parts of coconut oil fatty acid was used instead of 280 parts of soybean oil fatty acid. An addition reaction product having an acid value of 1.0 was obtained. Hereinafter, this is abbreviated as (a-2).

参考例4(同上) 大豆油脂肪酸の280部の代わりに、同量の脱水ひまし油
脂肪酸を使用するように変更した以外は、参考例1と同
様にして、目的とする付加反応物を得た。以下、これを
(a−3)と略記するが、このものの酸価は1.5であっ
た。
Reference Example 4 (same as above) A target addition reaction product was obtained in the same manner as in Reference Example 1 except that the same amount of dehydrated castor oil fatty acid was used instead of 280 parts of soybean oil fatty acid. Hereinafter, this is abbreviated as (a-3), but the acid value of this was 1.5.

参考例5(前掲の一般式〔I〕で示される重合性単量体
の調製例) 参考例1と同様の反応容器に、a−2の265部と、無水
イタコン酸の112部と、ハイドロキノンの0.1部とを仕込
んで、120℃で3時間のあいだ反応せしめ、次いで、プ
ロピレンオキサイドの60部を加えて、130℃で3時間の
あいだ反応せしめることにより、目的とする重合性単量
体を得た。以下、これを(m−2)と略記するが、この
ものの酸価は2.0であった。
Reference Example 5 (Preparation Example of Polymerizable Monomer Shown by General Formula [I]) In the same reaction vessel as in Reference Example 1, 265 parts of a-2, 112 parts of itaconic anhydride and hydroquinone were added. 0.1 part of was prepared and reacted at 120 ° C. for 3 hours, then 60 parts of propylene oxide was added and reacted at 130 ° C. for 3 hours to give the objective polymerizable monomer. Obtained. Hereinafter, this is abbreviated as (m-2), but the acid value of this was 2.0.

参考例6(同上) a−3の338部と、テトラヒドロ無水フタル酸の152部と
を仕込み、次いで、エチレンオキサイドの44部を加える
ように変更した以外は、参考例5と同様にして、目的重
合性単量体を得た。以下、これを(m−3)と略記する
が、このものの酸価は1.9であった。
Reference Example 6 (Same as above) The same procedure as in Reference Example 5 was repeated except that 338 parts of a-3 and 152 parts of tetrahydrophthalic anhydride were charged, and then 44 parts of ethylene oxide was added. A polymerizable monomer was obtained. Hereinafter, this is abbreviated as (m-3), but the acid value of this was 1.9.

実施例1 攪拌機、温度計、還流冷却器および窒素導入管を備えた
四つ口フラスコに、キシレンの400部およびm−1の360
部を仕込んで120℃に昇温し、そこにスチレン234部、メ
タクリル酸6部および過酸化ベンゾイル6部からなる混
合物を3時間に亘って滴下させ、その後も同温に10時間
保持せしめて、25℃におけるガードナー粘度(以下、こ
れを「粘度」と略記する。)がW−Xなる共重合体の溶
液を得た。
Example 1 In a four-necked flask equipped with a stirrer, a thermometer, a reflux condenser and a nitrogen inlet tube, 400 parts of xylene and 360 of m-1 were added.
Then, the mixture was heated to 120 ° C., a mixture of 234 parts of styrene, 6 parts of methacrylic acid and 6 parts of benzoyl peroxide was added dropwise thereto over 3 hours, and then the mixture was kept at the same temperature for 10 hours. A solution of a copolymer having a Gardner viscosity at 25 ° C. (hereinafter, abbreviated as “viscosity”) of W—X was obtained.

実施例2 スチレンの使用量を120部に変更する代わりに、その残
余である114部をn−ブチルアクリレートに変更して使
用した以外は、実施例1と同様にして粘度がS−Tなに
共重合体の溶液を得た。
Example 2 In the same manner as in Example 1, except that the amount of styrene used was changed to 120 parts and the remaining 114 parts was changed to n-butyl acrylate, the viscosity was ST. A solution of the copolymer was obtained.

実施例3 実施例1と同様に反応容器に、キシレンの400部と無水
マレイン酸の300部とを仕込んで120℃に昇温し、そこに
スチレンの105部とa−1の339部と過酸化ベンゾイルの
6部とからなる混合物を3時間に亘って滴下し、同温に
10時間保持して反応を続行させたのち、プロピレンオキ
シドお58部を1時間かけて滴下し、その後も同温に2時
間保持して反応を続行せしめて、粘度がQ−Rなる共重
合体の溶液を得た。
Example 3 As in Example 1, the reaction vessel was charged with 400 parts of xylene and 300 parts of maleic anhydride and heated to 120 ° C., and 105 parts of styrene and 339 parts of a-1 were added to the reaction vessel. A mixture consisting of 6 parts of benzoyl oxide was added dropwise over 3 hours at the same temperature.
After maintaining for 10 hours to continue the reaction, 58 parts of propylene oxide was added dropwise over 1 hour, and after that, the reaction was continued for 2 hours at the same temperature to continue the reaction, and a copolymer having a viscosity of QR was obtained. A solution of

実施例4 使用すべき単量体類として、m−2の180部、スチレン
の134部、メタクリル酸メチルの100部、メタクリル酸n
−ブチルの180部およびアクリル酸の6部からなる混合
物を用いるように変更した以外は、実施例1と同様にし
て、粘度がYなる共重合体の溶液を得た。
Example 4 As the monomers to be used, 180 parts of m-2, 134 parts of styrene, 100 parts of methyl methacrylate, n methacrylate
A copolymer solution having a viscosity of Y was obtained in the same manner as in Example 1 except that a mixture of 180 parts of butyl and 6 parts of acrylic acid was used.

実施例5 単量体類の組成として、m−3の300部、スチレンの134
部、メタクリル酸メチルの200部、メタクリル酸シクロ
ヘキシルの80部およびアクリル酸4−ヒドロキシエチル
の6部からなる混合物を用いるように変更した以外は、
実施例1と同様にして、粘度がSなる共重合体の溶液を
得た。
Example 5 As the composition of monomers, 300 parts of m-3 and 134 of styrene were used.
Parts, 200 parts of methyl methacrylate, 80 parts of cyclohexyl methacrylate and 6 parts of 4-hydroxyethyl acrylate, except that a mixture is used.
In the same manner as in Example 1, a copolymer solution having a viscosity of S was obtained.

実施例6 360部のm−1の代わりに、180部のm−1と、180部の
m−2とを用いるように変更した以外は、実施例1と同
様にして、粘度がVなる共重合体の溶液を得た。
Example 6 In the same manner as in Example 1 except that 180 parts of m-1 and 180 parts of m-2 were used instead of 360 parts of m-1, the viscosity was V. A polymer solution was obtained.

比較例1 実施例1と同様の反応容器に、キシレンの400部を仕込
んで120℃に昇温し、そこにスチレンの300部、n−ブチ
ルアクリレートの168部、β−ヒドロキシエチルメタク
リレートの120部、メタクリル酸の12部および過酸化ベ
ンゾイルの6部からなる混合物を3時間に亘って滴下
し、その後も10時間同温に保持して反応を続行させて、
粘度がZ1−Z2なるアクリル系樹脂の溶液を得た。
Comparative Example 1 A reactor similar to that used in Example 1 was charged with 400 parts of xylene and heated to 120 ° C., where 300 parts of styrene, 168 parts of n-butyl acrylate and 120 parts of β-hydroxyethyl methacrylate were added. , A mixture of 12 parts of methacrylic acid and 6 parts of benzoyl peroxide was added dropwise over 3 hours, and then the temperature was kept at the same temperature for 10 hours to continue the reaction.
An acrylic resin solution having a viscosity of Z 1 -Z 2 was obtained.

以上のようにして得られたそれぞれの共重合体(樹脂)
の70部に、各別に、「スーパーベッカミンJ−820−6
0」〔大日本インキ化学工業(株)製のメラミン樹脂〕
の30部および「タイペークR−680」〔石原産業(株)
製のルチル型酸化チタン〕の60部を混ぜた混合物を三本
ロールで練肉せしめて焼付型塗料を得た。
Each copolymer (resin) obtained as described above
70 parts of each, "Super Beckamine J-820-6
0 "[Melamine resin manufactured by Dainippon Ink and Chemicals, Inc.]
30 copies and "Taipeque R-680" [Ishihara Sangyo Co., Ltd.]
Of rutile-type titanium oxide] was mixed and kneaded with a three-roll to obtain a baking-type paint.

次いで、各種の塗料を用いて140℃で20分間焼き付けて
得られたそれぞれの塗膜について性能試験を行った処、
第1表に示すような結果が得られた。
Then, after performing a performance test on each coating film obtained by baking at 140 ° C. for 20 minutes using various paints,
The results shown in Table 1 were obtained.

実施例7および比較例2 「タイペークR−680」を用いて、PWC(顔料重量濃度)
が35%となるようにし、しかも、6%ナフテン酸コバル
トおよび24%ナフテン酸鉛をそれぞれ、実施例1の共重
合体および「スチレゾールM−1156」〔大日本インキ化
学工業(株)製のアクリル化アルキド樹脂〕に対して、
0.4%および0.8%ずつ各別に配合して塗料化し、次いで
この2種の塗料を常温(25℃)で乾燥せしめて得られた
それぞれの塗膜についても性能試験を行った処、第2表
に示すような結果が得られた。
Example 7 and Comparative Example 2 Using "Taypaque R-680", PWC (pigment weight concentration)
Of 35%, and 6% cobalt naphthenate and 24% lead naphthenate, respectively, were used to prepare the copolymer of Example 1 and "Styresol M-1156" [acrylic resin manufactured by Dainippon Ink and Chemicals, Inc.]. Alkyd resin],
A performance test was also conducted on each coating film obtained by mixing 0.4% and 0.8% separately into a paint, and then drying these two kinds of paint at room temperature (25 ° C). The results shown were obtained.

なお、第1表中に表示されている性能の判定基準は下記
によったものである。
The criteria for the performance shown in Table 1 are as follows.

○……良好、×……不良 なお、第2表中に表示されている性能の判定基準は下記
によったものである。
○ …… Good, × …… Poor The performance criteria shown in Table 2 are as follows.

○……良好、×……不良○ …… Good, × …… Poor

Claims (1)

【特許請求の範囲】[Claims] 【請求項1】構成単位として、 一般式 〔ただし、式中のR1はC7〜C20なる飽和ないしは不飽和
の脂肪酸残基を、R2はC2〜C4なるアルキレン基を、R3
C2〜C6なる重合性不飽和結合を有するジカルボン酸残基
を、R4はC2〜C4なるアルキレン基を表すものとする。〕 で示される重合性単量体の20〜90重量%と、スチレンの
80〜10重量%と、その他の共重合性単量体の0〜60重量
%とを含んで成る、約1,000〜30,000程度の数平均分子
量を有する被覆用共重合体。
1. A general formula as a structural unit (However, in the formula, R 1 is a saturated or unsaturated fatty acid residue of C 7 to C 20 , R 2 is an alkylene group of C 2 to C 4 , and R 3 is
A dicarboxylic acid residue having a polymerizable unsaturated bond of C 2 to C 6 is represented, and R 4 is an alkylene group of C 2 to C 4 . ] 20 to 90% by weight of the polymerizable monomer represented by
A coating copolymer having a number average molecular weight of about 1,000 to 30,000, which comprises 80 to 10% by weight and 0 to 60% by weight of other copolymerizable monomers.
JP58087590A 1983-05-20 1983-05-20 Copolymer for coating Expired - Lifetime JPH0692463B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP58087590A JPH0692463B2 (en) 1983-05-20 1983-05-20 Copolymer for coating

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP58087590A JPH0692463B2 (en) 1983-05-20 1983-05-20 Copolymer for coating

Publications (2)

Publication Number Publication Date
JPS59213713A JPS59213713A (en) 1984-12-03
JPH0692463B2 true JPH0692463B2 (en) 1994-11-16

Family

ID=13919209

Family Applications (1)

Application Number Title Priority Date Filing Date
JP58087590A Expired - Lifetime JPH0692463B2 (en) 1983-05-20 1983-05-20 Copolymer for coating

Country Status (1)

Country Link
JP (1) JPH0692463B2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL8901490A (en) * 1989-06-13 1991-01-02 Stamicarbon RESIN COMPOSITION SUITABLE FOR VIRTUALLY SOLVENT-FREE PAINT COMPOSITIONS.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4920948A (en) * 1972-06-15 1974-02-23
JPS5928231B2 (en) * 1974-08-05 1984-07-11 関西ペイント株式会社 Thermosetting high solids paint
US4065423A (en) * 1976-05-03 1977-12-27 Uniroyal, Inc. Paper coating latex compositions containing copolymers of monovinylidene aromatic monomer, aliphatic conjugated diene and an aryloyloxycarboxylic acid monomer

Also Published As

Publication number Publication date
JPS59213713A (en) 1984-12-03

Similar Documents

Publication Publication Date Title
US4883899A (en) End carboxyl bearing reactive vinyl monomers and preparation thereof
EP0242235B1 (en) Composite acrylic resin particles
US4990572A (en) Composite resin particles and preparation thereof
US4066586A (en) Polyester-modified vinyl polymer and production method thereof
EP0310331B1 (en) Non-aqueous dispersion, method of manufacture and use thereof
JPH0692463B2 (en) Copolymer for coating
EP0249505A2 (en) A two component polyurethane coating
JPH11171953A (en) Water-dilutable resin, its production and its usage
JPS5920317A (en) Production of polyester-modified acrylic copolymer for paint
EP0263499B1 (en) Process for producing grafted alkyd resin
JP3023915B2 (en) High solid content room temperature drying non-aqueous dispersion type resin composition
JPH0144255B2 (en)
JPS6223990B2 (en)
JP3127445B2 (en) Non-aqueous dispersion type resin composition
JPH0345749B2 (en)
JP2924003B2 (en) Method for producing high solids room temperature drying non-aqueous dispersion resin
JPH07118548A (en) One-pack stable low-temperature-curing resin composition
JPS62197468A (en) High-solid resin composition having excellent low-temperature curability
JPH0311283B2 (en)
JP2670668B2 (en) Resin composition for powder coating
JP3242713B2 (en) Manufacturing method of resin for matte paint
JPH0672215B2 (en) Paint
JPH0261993B2 (en)
JP3143917B2 (en) Non-aqueous dispersion and non-aqueous dispersion type resin composition
JPS60166312A (en) Production of synthetic resin for coating