JPH1088110A - Unsaturated fatty acid derivative and its use - Google Patents
Unsaturated fatty acid derivative and its useInfo
- Publication number
- JPH1088110A JPH1088110A JP26257696A JP26257696A JPH1088110A JP H1088110 A JPH1088110 A JP H1088110A JP 26257696 A JP26257696 A JP 26257696A JP 26257696 A JP26257696 A JP 26257696A JP H1088110 A JPH1088110 A JP H1088110A
- Authority
- JP
- Japan
- Prior art keywords
- unsaturated fatty
- fatty acid
- acid derivative
- composition
- acid
- 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.)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Sealing Material Composition (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、不飽和脂肪酸誘導
体ならびにこれらを含む接着剤、コーティング組成物お
よびシーラント組成物に関する。The present invention relates to unsaturated fatty acid derivatives and adhesives, coating compositions and sealant compositions containing them.
【０００２】[0002]
【従来の技術】天然ゴムに代表されるゴム系材料は二重
結合を有し、加硫することにより強靱性を向上させるこ
とができる。このとき、主鎖の不飽和二重結合が製品中
に残存すると耐候性などが悪くなるが、これらの現象を
無くすため全ての二重結合を架橋させるとゴム弾性を持
たないものとなり、実用に耐えない。2. Description of the Related Art Rubber-based materials represented by natural rubber have a double bond, and can be improved in toughness by vulcanization. At this time, if the unsaturated double bonds of the main chain remain in the product, the weather resistance and the like deteriorate, but if all the double bonds are crosslinked to eliminate these phenomena, the rubber will not have rubber elasticity and it will not be practical. I can't stand it.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、コーティン
グ組成物、シーラント組成物、粘着性組成物の構成要素
として用いることにより、それらの用途において高い架
橋密着と柔軟性とを両立させることのできる塗膜、シー
ラント、粘着剤となりうる化合物を提供することを目的
とする。DISCLOSURE OF THE INVENTION The present invention, by using it as a component of a coating composition, a sealant composition, or a tacky composition, can achieve both high crosslinking adhesion and flexibility in those applications. An object is to provide a compound that can be a coating film, a sealant, or an adhesive.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、かかる問
題を解決するために検討を行ったところ、特定構造の不
飽和脂肪酸誘導体を用いた各種用途の組成物、例えばコ
ーティング組成物で十分な可撓性を保持しながら高い強
度、密着性および耐熱性を有する硬化皮膜となることを
見い出し、本発明を完成するに至った。Means for Solving the Problems The inventors of the present invention have studied to solve the above-mentioned problems, and found that a composition for various uses using an unsaturated fatty acid derivative having a specific structure, for example, a coating composition, is sufficient. The inventors have found that a cured film having high strength, adhesion and heat resistance while maintaining excellent flexibility has been completed, and the present invention has been completed.
【０００５】すなわち本発明は、下記一般式（１）で表
される不飽和脂肪酸誘導体を提供するものである。ま
た、前記不飽和脂肪酸誘導体からなる粘着性組成物、コ
ーティング組成物およびシーラント組成物を提供するも
のである。以下、本発明を詳細に説明する。That is, the present invention provides an unsaturated fatty acid derivative represented by the following general formula (1). The present invention also provides an adhesive composition, a coating composition and a sealant composition comprising the unsaturated fatty acid derivative. Hereinafter, the present invention will be described in detail.
【０００６】[0006]
【化２】 Embedded image
【０００７】[0007]
【発明の実施の形態】本発明の不飽和脂肪酸誘導体は、
上記一般式（１）で表される。式中、Ｒ1は、炭素数１
〜１０のアルキル基であり、特に好ましくは炭素数２〜
５のアルキル基である。具体的には、メチル基、エチル
基、プロピル基、ブチル基、ペンチル基、ヘキシル基、
ヘプチル基、オクチル基、ノニル基、デシル基等が挙げ
られる。また、Ｒ2は、水酸基をｋ個（ｋは２以上の整
数）有する多価アルコールの残基（多価アルコール残
基）である。BEST MODE FOR CARRYING OUT THE INVENTION The unsaturated fatty acid derivative of the present invention comprises
It is represented by the general formula (1). In the formula, R 1 has 1 carbon atom
To 10 alkyl groups, particularly preferably having 2 to 2 carbon atoms.
5 alkyl groups. Specifically, methyl, ethyl, propyl, butyl, pentyl, hexyl,
Examples include a heptyl group, an octyl group, a nonyl group, and a decyl group. R 2 is a polyhydric alcohol residue (polyhydric alcohol residue) having k hydroxyl groups (k is an integer of 2 or more).
【０００８】一般式（１）で表される不飽和脂肪酸誘導
体は、不飽和脂肪酸または不飽和脂肪酸エステルと多価
アルコールをエステル化反応またはエステル交換反応さ
せて得ることができる。The unsaturated fatty acid derivative represented by the general formula (1) can be obtained by subjecting an unsaturated fatty acid or an unsaturated fatty acid ester to a polyhydric alcohol to an esterification reaction or a transesterification reaction.
【０００９】一般式（１）の不飽和脂肪酸誘導体のＲ1
−（ＣＨ＝ＣＨ−ＣＨ2）m−（ＣＨ2）n−ＣＯ−基を提
供する原料化合物としては、不飽和脂肪酸の内、炭素数
が１６〜２２の範囲のものが好ましく、特に好ましくは
炭素数が２０〜２２ある。また、式中、ｍが４〜６、ｎ
が１〜７であることが好ましい。具体的には、炭素数１
６のヘキサデカトリエン酸（６，１０，１４−ヘキサデ
カトリエン酸、６，９，１２−ヘキサデカトリエン酸、
７，１０，１３−ヘキサデカトリエン酸）、ヘキサデカ
テトラエン酸、炭素数１８のオクタデカテトラエン酸
（４，８，１２，１５−オクタデカテトラエン酸）、炭
素数２１のヘンエイコサペンタエン酸（６，９，１２，
１５，１８−ヘンエイコサペンタエン酸）、炭素数２０
のエイコサテトラエン酸（５，８，１１，１４−エイコ
サテトラエン酸、４，８，１２，１６−エイコサテトラ
エン酸）、エイコサペンタエン酸（５，８，１１，１
４，１７−エイコサペンタエン酸、４，８，１２，１
５，１８−エイコサペンタエン酸）、炭素数２２のドコ
サテトラエン酸（１０，１３，１６，１９−ドコサテト
ラエン酸）、ドコサペンタエン酸（７，１０，１３，１
６，１９−ドコサペンタエン酸）、ドコサヘキサエン酸
（ＤＨＡとも略す。４，７，１０，１３，１６，１９−
ドコサヘキサエン酸、４，８，１２，１５，１８，２１
−ドコサヘキサエン酸、４，８，１１，１４，１７，２
０−ドコサヘキサエン酸）の各不飽和脂肪酸が例示され
る。なお、不飽和脂肪酸は、魚油等の天然油脂から得る
ことができ、高純度品、混合物、あるいはこれらの誘導
体を含有する蒸留残留物を原料として使用することがで
きる。R 1 of the unsaturated fatty acid derivative of the general formula (1)
As the raw material compound that provides a — (CH ＝ CH—CH 2 ) m — (CH 2 ) n —CO— group, among unsaturated fatty acids, those having a carbon number of 16 to 22 are preferable, and particularly preferable are It has 20 to 22 carbon atoms. In the formula, m is 4 to 6, n
Is preferably 1 to 7. Specifically, carbon number 1
6 hexadecatrienoic acid (6,10,14-hexadecatrienoic acid, 6,9,12-hexadecatrienoic acid,
7,10,13-hexadecatrienoic acid), hexadecatetraenoic acid, octadecatetraenoic acid having 18 carbon atoms (4,8,12,15-octadecatetraenoic acid), heneicosapentaene having 21 carbon atoms Acid (6,9,12,
15,18-heneicosapentaenoic acid), carbon number 20
Eicosatetraenoic acid (5,8,11,14-eicosatetraenoic acid, 4,8,12,16-eicosatetraenoic acid), eicosapentaenoic acid (5,8,11,1
4,17-eicosapentaenoic acid, 4,8,12,1
5,18-eicosapentaenoic acid), docosatetraenoic acid having 22 carbon atoms (10,13,16,19-docosatetraenoic acid), docosapentaenoic acid (7,10,13,1)
6,19-docosapentaenoic acid) and docosahexaenoic acid (abbreviated also as DHA. 4,7,10,13,16,19-
Docosahexaenoic acid, 4, 8, 12, 15, 18, 21
Docosahexaenoic acid, 4, 8, 11, 14, 17, 2
0-docosahexaenoic acid). In addition, unsaturated fatty acids can be obtained from natural fats and oils such as fish oil, and high-purity products, mixtures, or distillation residues containing these derivatives can be used as raw materials.
【００１０】前記不飽和脂肪酸またはそのエステルとエ
ステル化反応またはエステル交換反応させるｋ価の多価
アルコールとしては、２官能のアルコールであるエチレ
ングリコール、プロピレングリコール、１，３−ブチレ
ングリコール、１，４−ブチレングリコール、などが例
示できる。３官能型のアルコールとしてはトリメチロー
ルプロパンが、４官能型のアルコールとしてはペンタエ
リスリトール、ジトリメチロールプロパンが例示でき
る。The k-valent polyhydric alcohol to be subjected to an esterification reaction or transesterification reaction with the unsaturated fatty acid or an ester thereof is a bifunctional alcohol such as ethylene glycol, propylene glycol, 1,3-butylene glycol, 1,4 -Butylene glycol, and the like. Examples of the trifunctional alcohol include trimethylolpropane, and examples of the tetrafunctional alcohol include pentaerythritol and ditrimethylolpropane.
【００１１】不飽和脂肪酸またはそのエステルとｋ価の
多価アルコールとのエステル化反応またはエステル交換
反応方法は特に限定を受けないが、通常の酸触媒または
カルボン酸のクロル化剤を用いて酸クロライドを経由す
るエステル化法、エステル交換法が最も好ましく用いら
れる。The method of esterification or transesterification of the unsaturated fatty acid or its ester with a polyhydric alcohol having a valency of k is not particularly limited, but the acid chloride may be prepared using a conventional acid catalyst or a carboxylic acid chlorinating agent. Most preferably, an esterification method and a transesterification method are used.
【００１２】エステル化またはエステル交換触媒として
は、スズ化合物、チタン化合物、アルミニウム化合物、
亜鉛化合物、モリブデン化合物およびジルコニウム化合
物などが例示できるが、取り扱い易さ、低毒性、反応
性、無着色性、熱安定性などのバランスからスズ化合
物、チタン化合物、アンチモン化合物が好ましく用いら
れる。スズ化合物としては具体的には、例えば塩化第一
スズ、オクチル酸第一スズ、モノブチルスズオキシド、
モノブチルスズトリス（２−エチルヘキシルヘキサネー
ト）等のモノブチルスズ化合物、ジブチルスズオキシド
等のジブチルスズ化合物が挙げられる。また、チタン化
合物としては、テトラブチルチタネート、テトライソプ
ロピルチタネート、アンチモン化合物としては三酸化ア
ンチモン等が挙げられる。これらを各単独であるいは、
混合した触媒存在下に、常圧または減圧下、温度１００
〜３００℃、好ましくは１５０〜２２０℃でエステル化
またはエステル交換反応を行う。As the esterification or transesterification catalyst, tin compounds, titanium compounds, aluminum compounds,
A zinc compound, a molybdenum compound, a zirconium compound, and the like can be exemplified, but a tin compound, a titanium compound, and an antimony compound are preferably used in terms of balance between ease of handling, low toxicity, reactivity, non-coloring property, and thermal stability. As the tin compound, specifically, for example, stannous chloride, stannous octoate, monobutyltin oxide,
Monobutyltin compounds such as monobutyltin tris (2-ethylhexyl hexanate) and dibutyltin compounds such as dibutyltin oxide are exemplified. Examples of the titanium compound include tetrabutyl titanate and tetraisopropyl titanate, and examples of the antimony compound include antimony trioxide. Each of these alone or
In the presence of a mixed catalyst, at normal pressure or reduced pressure, temperature 100
The esterification or transesterification reaction is carried out at a temperature of 300 to 300C, preferably 150 to 220C.
【００１３】本発明の一般式（１）で表される不飽和脂
肪酸誘導体は、その分子末端に近い箇所に不飽和脂肪酸
部を有するため、分子内部に不飽和結合を持つ化合物に
比べ分子の末端部に近い二重結合が架橋するので、これ
を用いて接着剤、シーラント組成物やコーティング組成
物にした場合に架橋性が高くなり、強度及び耐熱性を向
上させることができる。Since the unsaturated fatty acid derivative represented by the general formula (1) of the present invention has an unsaturated fatty acid moiety near the molecular terminal, the terminal of the molecule is compared with a compound having an unsaturated bond inside the molecule. Since the double bond near the part is cross-linked, when the double bond is used as an adhesive, a sealant composition or a coating composition, the cross-linking property is increased, and the strength and heat resistance can be improved.
【００１４】本発明の不飽和脂肪酸誘導体は、公知の方
法で混合・調整して、接着剤、コーティング剤、シーラ
ント剤とすることができる。なお、得られた組成物、特
に熱可塑性樹脂との組成物は、成形し成形品とすること
もできる。The unsaturated fatty acid derivative of the present invention can be mixed and adjusted by a known method to obtain an adhesive, a coating agent and a sealant. In addition, the obtained composition, especially a composition with a thermoplastic resin, can also be molded to form a molded article.
【００１５】本発明の粘着性組成物は前記一般式（１）
で表される不飽和脂肪酸誘導体を含むことを特徴とす
る。この不飽和脂肪酸誘導体は、接着性組成物中におい
て可撓性付与剤および強度付与剤として作用するもので
ある。粘着性組成物は、一般的には、粘着性付与樹脂や
柔軟性付与剤等の公知の粘着剤組成成分と一緒に不飽和
脂肪酸誘導体を配合した組成からなる。粘着性を上げる
ために使用の前後に粘着剤組成物を加熱することにより
硬化を促進してもよい。また、粘着剤使用の前後に放射
線を照射することによって硬化を促進してもよい。本発
明の粘着性組成物はホットメルト接着剤、溶剤溶解型接
着剤、積層接着剤、感圧タイプ接着剤などの多くの異な
る種類の接着剤として使用してもよい。The adhesive composition of the present invention has the general formula (1)
Characterized by containing an unsaturated fatty acid derivative represented by the formula: This unsaturated fatty acid derivative acts as a flexibility imparting agent and a strength imparting agent in the adhesive composition. The pressure-sensitive adhesive composition generally has a composition in which an unsaturated fatty acid derivative is blended together with a known pressure-sensitive adhesive composition component such as a tackifier resin or a softener. Curing may be promoted by heating the pressure-sensitive adhesive composition before and after use to increase tackiness. The curing may be promoted by irradiating radiation before and after the use of the pressure-sensitive adhesive. The adhesive composition of the present invention may be used as many different types of adhesives such as hot melt adhesives, solvent-soluble adhesives, laminating adhesives, pressure-sensitive adhesives, and the like.
【００１６】本発明のコーティング組成物は、前記一般
式（１）で表される不飽和脂肪酸誘導体を含むことを特
徴とする。この不飽和脂肪酸誘導体は、コーティング中
において可撓性付与剤および強度付与剤として作用する
ものである。本発明のコーティング組成物は、不飽和脂
肪酸誘導体、その他の塗料用樹脂、任意の硬化剤、硬化
助剤、顔料、溶媒、安定剤などの成分を様々に混合した
成分からなる。また、得られた組成物は既知の方法で塗
布することができる。塗布後に硬化性を上げるため加熱
焼き付けを行ってもよい。また、塗布後放射線を照射す
ることによって硬化を促進してもよい。コーティング剤
とする場合は、アルキッド樹脂等の塗料用樹脂１００部
に対し、不飽和脂肪酸誘導体を２０〜２００部配合する
ことが好ましい。組成物の混練などは、常法に従い、公
知の方法によって調製することができる。The coating composition of the present invention is characterized by containing the unsaturated fatty acid derivative represented by the general formula (1). This unsaturated fatty acid derivative functions as a flexibility imparting agent and a strength imparting agent during coating. The coating composition of the present invention is composed of components obtained by variously mixing components such as unsaturated fatty acid derivatives, other resins for coating materials, optional curing agents, curing aids, pigments, solvents, and stabilizers. Further, the obtained composition can be applied by a known method. After application, baking may be performed to enhance the curability. In addition, curing may be promoted by irradiating radiation after application. When it is used as a coating agent, it is preferable to add 20 to 200 parts of an unsaturated fatty acid derivative to 100 parts of a coating resin such as an alkyd resin. The kneading of the composition and the like can be prepared according to a conventional method by a known method.
【００１７】本発明のシーラント組成物は前記一般式
（１）で表される不飽和脂肪酸誘導体を含むことを特徴
とする。この不飽和脂肪酸誘導体は、シーラント組成物
中において可撓性付与剤、強度付与剤および相容化剤と
して作用するものである。本発明のシーラント組成物
は、ブロックポリマー、およびアスファルトなどの瀝青
質、亜麻仁油、魚油などの脂肪油、天然ゴム、クロロプ
レンゴム、ブチルゴム、ポリブタジエンなどのゴム、ポ
リ酢酸ビニル、ポリ塩化ビニル、エポキシ樹脂、不飽和
ポリエステル樹脂などの合成樹脂、ポリウレタン、ポリ
サルファイド、シリコンラバー、ＳＢＳなどのエラスト
マー等のシーラント主剤、更には有機または及び無機質
の充填剤を含むものである。シーラント剤とする場合
は、前記シーラント主剤１００部に対し、不飽和脂肪酸
誘導体を１０〜５０部配合することが好ましい。The sealant composition of the present invention is characterized by containing the unsaturated fatty acid derivative represented by the general formula (1). The unsaturated fatty acid derivative functions as a flexibility-imparting agent, a strength-imparting agent, and a compatibilizer in the sealant composition. The sealant composition of the present invention includes block polymers, bituminous substances such as asphalt, linseed oil, fatty oils such as fish oil, natural rubber, chloroprene rubber, butyl rubber, rubbers such as polybutadiene, polyvinyl acetate, polyvinyl chloride, and epoxy resin. , A synthetic resin such as an unsaturated polyester resin, a sealant base such as an elastomer such as polyurethane, polysulfide, silicone rubber, and SBS, and an organic or inorganic filler. When a sealant is used, it is preferable to add 10 to 50 parts of an unsaturated fatty acid derivative to 100 parts of the sealant main agent.
【００１８】本発明の不飽和脂肪酸誘導体は、熱可塑性
樹脂、任意の硬化剤、硬化助剤、粘着性付与剤、可塑
剤、溶媒、安定剤などの成分を様々に加えたり混合し、
接着剤、コーティング剤、シーラント組成物の他、常法
に従ってインキ、繊維、ＦＲＰ、ＳＭＣ、アスファル
ト、ポリマーアロイとしても使用することができる。The unsaturated fatty acid derivative of the present invention is prepared by adding or mixing various components such as a thermoplastic resin, an optional curing agent, a curing aid, a tackifier, a plasticizer, a solvent, and a stabilizer.
In addition to an adhesive, a coating agent, a sealant composition, it can be used as an ink, fiber, FRP, SMC, asphalt, or polymer alloy according to a conventional method.
【００１９】本発明の不飽和脂肪酸誘導体を用いた各用
途のおいては、様々な方法でそれらに含まれる前記不飽
和脂肪酸誘導体を架橋することができる。例えば、有機
過酸化物とスチレンモノマーを用いたスチレンモノマー
の付加架橋、コバルト、マンガンの有機酸塩等の金属ド
ライヤーによる酸化還元反応による自動酸化架橋、硫黄
系加硫剤を用いた架橋、ＵＶ・電子線およびγ線による
放射線架橋などが例示できる。In each application using the unsaturated fatty acid derivative of the present invention, the unsaturated fatty acid derivative contained therein can be crosslinked by various methods. For example, addition crosslinking of a styrene monomer using an organic peroxide and a styrene monomer, automatic oxidation crosslinking by a redox reaction with a metal dryer such as an organic acid salt of cobalt or manganese, crosslinking using a sulfur-based vulcanizing agent, UV / Examples include radiation crosslinking by electron beams and γ rays.
【００２０】[0020]
【実施例】以下、実施例により本発明を具体的に説明す
るが、本発明はこれらに限定されるものではない。なお
「％」は、特に示す場合を除くほか「重量％」を示す。
ＮＭＲは日本電子製「ＧＸＳ２７０ＷＢ」を、ＩＲはＪ
ＡＳＣＯ製「ＦＴ／ＩＲ−５３００」を、ＧＰＣは島津
製作所製「ＨＰＬＣ ＬＣ−６Ａ ＳＹＳＴＥＭ」（カ
ラム：ポリスチレンカラム，溶媒：ＴＨＦ）を用いた。EXAMPLES The present invention will now be described specifically with reference to examples, but the present invention is not limited to these examples. “%” Indicates “% by weight” unless otherwise indicated.
NMR refers to JEOL “GXS270WB”, IR refers to J
"FT / IR-5300" manufactured by ASCO and "HPLC LC-6A SYSTEM" manufactured by Shimadzu (column: polystyrene column, solvent: THF) were used for GPC.
【００２１】［合成実施例１］ドコサヘキサエン酸エチ
ルエステル（ＧＣ純度７０％：魚油より有効成分蒸留後
の残渣／ヨウ素価３７３）３００ｇ、及びトリメチロー
ルプロパン３６．３ｇ、テトラブトキシチタン０．３４
ｇを脱水管付きフラスコに仕込み、２００℃で２４時間
反応させた。反応物の分子量分布をＧＰＣで測定する
と、スチレン換算で分子量が３５０付近のピークが消失
しており、ドコサヘキサエン酸のトリメチロールプロパ
ン付加物Ａ−１を３３３．４ｇ得た。得られた製品の性
状は、粘度１２０４ｃＰ／２５℃であった。Synthesis Example 1 300 g of docosahexaenoic acid ethyl ester (GC purity: 70%; residue after distilling active ingredient from fish oil / iodine value: 373), 36.3 g of trimethylolpropane, 0.34 of tetrabutoxytitanium
g was charged into a flask with a dehydrating tube and reacted at 200 ° C. for 24 hours. When the molecular weight distribution of the reaction product was measured by GPC, the peak at a molecular weight of around 350 in terms of styrene disappeared, and 333.4 g of a trimethylolpropane adduct of docosahexaenoic acid A-1 was obtained. The properties of the obtained product were a viscosity of 1204 cP / 25 ° C.
【００２２】［合成実施例２］ドコサヘキサエン酸エチ
ルエステル（ＧＣ純度７０％：魚油より有効成分蒸留後
の残渣／ヨウ素価３７３）３００ｇ、及びエチレングリ
コール２５．２ｇ、テトラブトキシチタン０．３２ｇを
脱水管付きフラスコに仕込み、２００℃で２４時間反応
させた。反応物の分子量分布をＧＰＣで測定すると、ス
チレン換算で分子量が３５０付近のピークが消失してお
り、ドコサヘキサエン酸のエチレングリコール付加物Ａ
−２を３２１．５ｇ得た。得られた製品の性状は、粘度
８６６ｃＰ／２５℃であった。[Synthesis Example 2] 300 g of ethyl docosahexaenoic acid ester (GC purity: 70%: residue after distilling an active ingredient from fish oil / iodine value: 373), 25.2 g of ethylene glycol, and 0.32 g of tetrabutoxytitanium were put into a dehydrating tube. The flask was charged and reacted at 200 ° C. for 24 hours. When the molecular weight distribution of the reaction product was measured by GPC, the peak at a molecular weight of around 350 in terms of styrene disappeared, and the ethylene glycol adduct A of docosahexaenoic acid was found.
-2 was obtained in an amount of 321.5 g. The properties of the obtained product were a viscosity of 866 cP / 25 ° C.
【００２３】［実施例１〜４］合成例１、２で合成した
ＤＨＡ誘導体をアルキッド樹脂（ベッコゾール ＥＳ−
５００３−５０：大日本インキ製）に表−１のような割
合で配合した。得られた塗料を金属板（ＳＰＴＥ：５０
×１５０×０．３ｍｍ）に塗布し、常温で４８時間乾燥
させた。塗膜性状の試験結果を表−２に示す。[Examples 1 to 4] The DHA derivative synthesized in Synthesis Examples 1 and 2 was converted to an alkyd resin (Veccosol ES-
5003-50: manufactured by Dainippon Ink) at a ratio as shown in Table 1. The obtained paint was applied to a metal plate (SPTE: 50
× 150 × 0.3 mm) and dried at room temperature for 48 hours. Table 2 shows the test results of the properties of the coating film.
【００２４】［比較例１］不飽和脂肪酸誘導体を使用せ
ず、表−１に記載の配合例に従って塗料を得、実施例１
と同様に試験した。試験結果を表−２に示す。Comparative Example 1 A coating material was obtained according to the formulation examples shown in Table 1 without using unsaturated fatty acid derivatives.
The same test was performed. Table 2 shows the test results.
【００２５】[0025]
【表１】 [Table 1]
【００２６】[0026]
【表２】 [Table 2]
【００２７】［測定項目］ （１）鉛筆硬度 ＪＩＳ Ｋ５４００ ８．４に従い、三菱ユニ（三菱鉛
筆（株）製）を用いて、塗膜が傷付き始める時点の鉛筆
の硬度をもって表示した。 （２）光沢 ＪＩＳ Ｋ５４００ ７．６に従い、６０度鏡面反射率
（％）をもって表示した。 （３）屈曲性 ＪＩＳ Ｋ５４００ ８．１に準じて、心棒の直径を２
ｍｍとして、塗膜を折り曲げたときの塗膜外観を目視で
観察し、割れ・はがれを認めない場合は○、認められる
場合は×と表示した。 （３）密着性 ＪＩＳ Ｋ５４００ ８．５の碁盤目テープ法に準じ
て、隙間間隔１ｍｍの切り傷を碁盤目状に付け、この碁
盤目の上に粘着テープをはり、はがした後の塗膜の付着
状態を目視で観察し１０段階の評価を行った。[Measurement Items] (1) Pencil Hardness According to JIS K5400 8.4, the hardness of the pencil at the time when the coating film starts to be scratched was indicated using Mitsubishi Uni (manufactured by Mitsubishi Pencil Co., Ltd.). (2) Gloss In accordance with JIS K5400 7.6, the gloss was indicated with a 60-degree specular reflectance (%). (3) Flexibility According to JIS K5400 8.1, the diameter of the mandrel is 2
mm, the appearance of the coating film when the coating film was bent was visually observed. When no cracking or peeling was observed, it was indicated by ○, and when it was observed, it was indicated by x. (3) Adhesion According to the grid tape method of JIS K5400 8.5, cuts with a gap of 1 mm are made in a grid pattern, and an adhesive tape is peeled off the grid and the coating film after peeling is removed. The adhered state was visually observed and evaluated on a 10-point scale.
【００２８】[0028]
【発明の効果】本発明の不飽和脂肪酸誘導体およびこれ
からなるコーティング組成物等は、金属などの基材表面
に塗布し、次いで加熱、乾燥または紫外線や電子線など
の活性エネルギー線の照射等により、優れた屈曲性と密
着性とを有する硬化被膜を得ることができる。The unsaturated fatty acid derivative of the present invention and a coating composition comprising the same are applied to the surface of a substrate such as a metal and then heated, dried or irradiated with an active energy ray such as ultraviolet rays or an electron beam. A cured film having excellent flexibility and adhesion can be obtained.
Claims (5)
酸誘導体。 【化１】 1. An unsaturated fatty acid derivative represented by the following general formula (1). Embedded image
トリメチロールプロパン、ジトリメチロールプロパン、
１，３−ブチレングリコール、１，４−ブチレングリコ
ールまたはペンタエリスリトールのいずれかである請求
項１記載の不飽和脂肪酸誘導体。2. The polyhydric alcohol is ethylene glycol,
Trimethylolpropane, ditrimethylolpropane,
The unsaturated fatty acid derivative according to claim 1, which is any one of 1,3-butylene glycol, 1,4-butylene glycol, and pentaerythritol.
導体を含む粘着性組成物。3. An adhesive composition comprising the unsaturated fatty acid derivative according to claim 1 or 2.
導体を含むコーティング組成物。4. A coating composition comprising the unsaturated fatty acid derivative according to claim 1.
導体を含むシーラント組成物。5. A sealant composition comprising the unsaturated fatty acid derivative according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26257696A JPH1088110A (en) | 1996-09-11 | 1996-09-11 | Unsaturated fatty acid derivative and its use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26257696A JPH1088110A (en) | 1996-09-11 | 1996-09-11 | Unsaturated fatty acid derivative and its use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH1088110A true JPH1088110A (en) | 1998-04-07 |
Family
ID=17377736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26257696A Pending JPH1088110A (en) | 1996-09-11 | 1996-09-11 | Unsaturated fatty acid derivative and its use |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH1088110A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008048983A2 (en) * | 2006-10-17 | 2008-04-24 | Lubrizol Advanced Materials, Inc. | Reactive carrier for air drying coatings |
-
1996
- 1996-09-11 JP JP26257696A patent/JPH1088110A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008048983A2 (en) * | 2006-10-17 | 2008-04-24 | Lubrizol Advanced Materials, Inc. | Reactive carrier for air drying coatings |
| WO2008048983A3 (en) * | 2006-10-17 | 2008-10-09 | Lubrizol Advanced Mat Inc | Reactive carrier for air drying coatings |
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