JP5265858B2 - Snow-sliding coating - Google Patents
Snow-sliding coating Download PDFInfo
- Publication number
- JP5265858B2 JP5265858B2 JP2006163656A JP2006163656A JP5265858B2 JP 5265858 B2 JP5265858 B2 JP 5265858B2 JP 2006163656 A JP2006163656 A JP 2006163656A JP 2006163656 A JP2006163656 A JP 2006163656A JP 5265858 B2 JP5265858 B2 JP 5265858B2
- Authority
- JP
- Japan
- Prior art keywords
- polymerizable
- snow
- polyester
- coating film
- acrylate
- 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 - Fee Related
Links
- 239000011248 coating agent Substances 0.000 title claims abstract description 25
- 238000000576 coating method Methods 0.000 title claims abstract description 25
- -1 polydimethylsiloxane Polymers 0.000 claims abstract description 54
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims abstract description 44
- 239000004205 dimethyl polysiloxane Substances 0.000 claims abstract description 43
- 229920000728 polyester Polymers 0.000 claims abstract description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 229920000570 polyether Polymers 0.000 claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 16
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 16
- 239000000178 monomer Substances 0.000 claims abstract description 16
- 238000010894 electron beam technology Methods 0.000 claims abstract description 12
- 239000012948 isocyanate Substances 0.000 claims abstract description 9
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 25
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 125000002348 vinylic group Chemical group 0.000 abstract 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 40
- 239000000047 product Substances 0.000 description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000003973 paint Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011120 plywood Substances 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- ORFPMGWJDWEAAQ-UHFFFAOYSA-N (4-ethenylphenyl)-triethoxysilane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(C=C)C=C1 ORFPMGWJDWEAAQ-UHFFFAOYSA-N 0.000 description 1
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
- OZCRKDNRAAKDAN-IWQZZHSRSA-N (z)-but-1-ene-1,4-diol Chemical compound OCC\C=C/O OZCRKDNRAAKDAN-IWQZZHSRSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- SZBXTBGNJLZMHB-UHFFFAOYSA-N 1-chloro-2,4-diisocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1N=C=O SZBXTBGNJLZMHB-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 1
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- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
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- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
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Landscapes
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Abstract
Description
本発明は積もった雪が滑落するような表面を有する滑雪性塗膜に関するものである。 The present invention relates to a snow-sliding coating film having a surface on which accumulated snow slides.
この種の滑雪性塗膜の材料としては、重合性不飽和結合を有するポリオルガノシロキサンが提供されている（例えば特許文献１〜４参照）。 As a material for this type of snow slidable coating film, polyorganosiloxane having a polymerizable unsaturated bond is provided (see, for example, Patent Documents 1 to 4).
上記滑雪性塗膜は比較的分子量が小さく、したがって耐久性に劣り、かつ基材との接着性も充分でない、という問題がある。 The snow slidable coating film has a problem that it has a relatively small molecular weight, is inferior in durability, and is not sufficiently adhesive to the substrate.
本発明は上記従来の課題を解決するための手段として、重合性（メタ）アクリル基含有ポリジメチルシロキサンと、重合性ポリエステルおよび／またはポリエーテル（メタ）アクリレートと、水酸基含有ポリジメチルシロキサンと、多価イソシアネートとの混合物を電子線照射によって硬化させた硬化物からなり、雪が滑落するような表面を有することを特徴とする滑雪性塗膜を提供するものである。
上記混合物には更に重合性ビニル単量体を添加してもよい。
As means for solving the above conventional problems, the present invention provides a polymerizable (meth) acryl group-containing polydimethylsiloxane, a polymerizable polyester and / or polyether (meth) acrylate, a hydroxyl group-containing polydimethylsiloxane, the mixture of the valence isocyanate Ri Do a cured product obtained by curing by electron beam irradiation, there is provided a Namerayuki coating film, characterized in Rukoto that have a surface, such as snow to slide off.
The above mixture but it may also be added to further polymerizable vinyl monomer.
（削除） ( Delete )
（削除） ( Delete )
〔作用〕
請求項１の発明
重合性（メタ）アクリル基含有ポリジメチルシロキサンと、重合性ポリエステルおよび／またはポリエーテル（メタ）アクリレートと、水酸基含有ポリジメチルシロキサンと、多価イソシアネートとを添加した混合物に電子線照射すると、該混合物中の重合性（メタ）アクリル基含有ポリジメチルシロキサンと重合性ポリエステルおよび／またはポリエーテル（メタ）アクリレートとが迅速に共重合して巨大高分子化し、更に水酸基含有ポリジメチルシロキサンと多価イソシアネートとは重縮合することによって巨大高分子化する。上記混合物の硬化は電子線照射によって低温、低エネルギー状態で行われ、そして水酸基含有ポリジメチルシロキサンと多価イソシアネートとの重縮合反応も室温で行われるから加熱の必要もなく、エネルギーを節約することが出来、かつ耐熱性のない基材表面にも硬化物塗膜を容易に形成することができる。そして該硬化物は上記したように分子量の大きな巨大高分子となり、該巨大高分子中に含まれるポリジメチルシロキサン部分によって該硬化物塗膜には滑雪性が与えられ、そして該硬化物塗膜は上記したように巨大高分子からなるので、耐候性、耐汚染性、耐磨耗性に優れている。
[Action]
Invention of Claim 1
When a mixture containing a polymerizable (meth) acrylic group-containing polydimethylsiloxane, a polymerizable polyester and / or polyether (meth) acrylate, a hydroxyl group-containing polydimethylsiloxane, and a polyvalent isocyanate is irradiated with an electron beam, the mixture The polymerizable (meth) acrylic group-containing polydimethylsiloxane and the polymerizable polyester and / or polyether (meth) acrylate are rapidly copolymerized into a large polymer, and further, the hydroxyl group-containing polydimethylsiloxane and the polyvalent isocyanate Becomes a large polymer by polycondensation. Curing of the above mixture is performed at low temperature and low energy by electron beam irradiation, and polycondensation reaction of polydimethylsiloxane containing hydroxyl group and polyvalent isocyanate is also performed at room temperature, so there is no need for heating and energy saving. Thus, a cured coating film can be easily formed on the surface of a substrate having no heat resistance. The cured product becomes a macromolecule having a large molecular weight as described above, and the cured film is provided with a snow slidability by the polydimethylsiloxane portion contained in the macromolecule. As described above, it is composed of a large polymer, so it has excellent weather resistance, stain resistance, and wear resistance.
請求項２の発明
上記混合物に更に重合性ビニル単量体を添加し、電子線照射によって共重合させ硬化させると、該重合性ビニル単量体の種類によって硬化物塗膜の硬度の調節や基材に対する接着性を改良することができる。
Invention of Claim 2 When a polymerizable vinyl monomer is further added to the mixture and copolymerized by electron beam irradiation and cured, the hardness of the cured coating film can be adjusted depending on the type of the polymerizable vinyl monomer. The adhesion to the material can be improved.
〔効果〕
本発明にあっては、上記混合物を低温低エネルギー状態で迅速に硬化させることが出来るから、塗膜形成のために要するエネルギーが節約され、かつ硬化物は巨大高分子となるから滑雪性、耐候性、耐汚染性、耐磨耗性、に優れた塗膜を得ることが出来る。
〔effect〕
In the present invention, since the mixture can be rapidly cured at a low temperature and low energy, the energy required for forming a coating film is saved, and the cured product becomes a giant polymer, so that it is snow slidable and weather resistant. It is possible to obtain a coating film having excellent properties, stain resistance, and abrasion resistance.
以下に本発明を詳細に説明する。
〔重合性（メタ）アクリル基含有ポリジメチルシロキサン〕
本発明において使用する重合性（メタ）アクリル基含有ポリジメチルシロキサンは、片末端または両末端に水酸基を有するポリジメチルシロキサンにアクリル酸および／またはメタクリル酸をエステル化反応によって結合することによって製造される。上記片末端または両末端に水酸基を有するポリジメチルシロキサンの水酸基は、該ポリジメチルシロキサンの片末端または両末端に存在するシラノール基に由来するものでもよいが、電子線照射による硬化性を高め、かつ硬化物の分子量を高めるためには、該ポリジメチルシロキサンの片末端または両末端をポリエステルおよび／またはポリエーテルで変性したポリエステルおよび／またはポリエーテル変性ポリジメチルシロキサンの片末端または両末端に存在する水酸基にアクリル酸および／またはメタクリル酸をエステル化反応によって結合したポリエステルおよび／またはポリエーテル変性（メタ）アクリル基含有ポリジメチルシロキサンを選択することが好ましい。
The present invention is described in detail below.
[Polymethylsiloxane containing polymerizable (meth) acrylic group]
The polymerizable (meth) acrylic group-containing polydimethylsiloxane used in the present invention is produced by bonding acrylic acid and / or methacrylic acid to a polydimethylsiloxane having a hydroxyl group at one or both ends by an esterification reaction. . The hydroxyl group of the polydimethylsiloxane having a hydroxyl group at one end or both ends may be derived from a silanol group present at one end or both ends of the polydimethylsiloxane. In order to increase the molecular weight of the cured product, a hydroxyl group present at one or both ends of the polyester and / or polyether-modified polydimethylsiloxane obtained by modifying one end or both ends of the polydimethylsiloxane with polyester and / or polyether. It is preferable to select a polyester and / or a polyether-modified (meth) acrylic group-containing polydimethylsiloxane in which acrylic acid and / or methacrylic acid are bound to each other by an esterification reaction.
上記ポリエステル変性アクリル基含有ポリジメチルシロキサンは、例えば下記の構造を有する。
上記ポリエーテル変性アクリル基含有ポリジメチルシロキサンは、例えば下記の構造を有する。
上記ポリエステル変性アクリル基含有ポリジメチルシロキサンの市販品としては、ＢＹＫ−３７１（商品名；ＢＹＫケミー社製）がある。 As a commercially available product of the polyester-modified acrylic group-containing polydimethylsiloxane, there is BYK-371 (trade name; manufactured by BYK Chemie).
上記重合性（メタ）アクリル基含有ポリジメチルシロキサンとして更に望ましいのは、該ポリジメチルシロキサンの片末端または両末端に多価イソシアネートとポリエステルおよび／またはポリエーテルを重縮合させることによって製造される末端ポリエステルおよび／または末端ポリエーテルポリウレタン変性ポリジメチルシロキサンのポリエステルおよび／またはポリエーテル末端の水酸基にアクリル酸および／またはメタクリル酸をエステル化反応によって結合したポリウレタン変性（メタ）アクリル基含有ポリジメチルシロキサンである。 More desirable as the polymerizable (meth) acrylic group-containing polydimethylsiloxane is a terminal polyester produced by polycondensation of a polyisocyanate and a polyester and / or a polyether at one or both ends of the polydimethylsiloxane. And / or a polyurethane-modified (meth) acrylic group-containing polydimethylsiloxane in which acrylic acid and / or methacrylic acid is bonded to a polyester of a terminal polyether polyurethane-modified polydimethylsiloxane and / or a hydroxyl group of a polyether terminal by an esterification reaction.
上記ポリウレタン変性アクリル基含有ポリジメチルシロキサンは、例えば下記の構造を有する。
上記ポリウレタン変性アクリル基含有ポリジメチルシロキサンの市販品としては、ＢＹＫ−ＵＶ−３５７０（商品名；ＢＹＫケミー社製）がある。 As a commercial item of the polyurethane-modified acrylic group-containing polydimethylsiloxane, there is BYK-UV-3570 (trade name; manufactured by BYK Chemie).
〔重合性ポリエステルおよび／またはポリエーテル（メタ）アクリレート〕
本発明において使用する重合性ポリエステルおよび／またはポリエーテル（メタ）アクリレートは、ポリエステルおよび／またはポリエーテルの両末端および／または側鎖の水酸基にアクリル酸および／またはメタクリル酸をエステル化反応によって結合したものである。例えば２官能ポリエステルアクリレートは下記の構造を有し（〔化４〕）、３官能以上のポリエステルアクリレートは下記の構造を有する。（〔化５〕）。
[Polymerizable polyester and / or polyether (meth) acrylate]
In the polymerizable polyester and / or polyether (meth) acrylate used in the present invention, acrylic acid and / or methacrylic acid are bonded to hydroxyl groups at both ends and / or side chains of the polyester and / or polyether by an esterification reaction. Is. For example, the bifunctional polyester acrylate has the following structure ([Chemical Formula 4]), and the trifunctional or higher functional polyester acrylate has the following structure. ([Chemical Formula 5]).
上記２官能ポリエステルアクリレートの市販品としては、Ｍ−６２５０（商品名；チッソ株式会社製）があり、上記多官能ポリエステルアクリレートの市販品としては、Ｍ−７１００（商品名；チッソ株式会社製）がある。 As a commercially available product of the bifunctional polyester acrylate, there is M-6250 (trade name; manufactured by Chisso Corporation), and as a commercially available product of the polyfunctional polyester acrylate, M-7100 (trade name; manufactured by Chisso Corporation) is available. is there.
〔水酸基含有ポリジメチルシロキサン〕
本発明において使用する水酸基含有ポリジメチルシロキサンとしては、片末端または両末端にシラノール基を有するポリジメチルシロキサンがあるが、電子線照射による硬化性を高めるためには、片末端または両末端をポリエステルおよび／またはポリエーテルによって変性したポリエステルおよび／またはポリエーテル変性ポリジメチルシロキサンを選択することが好ましい。ポリエステルとして２価アルコールと２塩基酸とを原料としたものは、片末端または両末端に水酸基を有し（〔化６〕）、多価アルコールと多塩基酸とを原料としたものは、片末端または両末端と側鎖とに水酸基を有する（〔化７〕）。
[Hydroxyl-containing polydimethylsiloxane]
As the hydroxyl group-containing polydimethylsiloxane used in the present invention, there is a polydimethylsiloxane having a silanol group at one end or both ends. In order to improve the curability by electron beam irradiation, one end or both ends are polyester and Preference is given to selecting polyesters and / or polyether-modified polydimethylsiloxanes modified with polyethers. Polyesters using dihydric alcohols and dibasic acids as raw materials have hydroxyl groups at one or both ends (Chemical Formula 6), and those using polyhydric alcohols and polybasic acids as raw materials are It has a hydroxyl group at the terminal or both terminals and side chain ([Chemical Formula 7])
更にポリエーテル−ポリエステル変性水酸基含有ポリジメチルシロキサンとしては、〔化８〕に示す構造のものがある。 Further, the polyether-polyester-modified hydroxyl group-containing polydimethylsiloxane has a structure shown in [Chemical Formula 8].
ポリエステル変性水酸基含有ポリジメチルシロキサンの市販品としては、ＢＹＫ−３７０（商品名；ＢＹＫケミー社製）があり、ポリエーテル変性水酸基含有ポリジメチルシロキサンの市販品としては、ＢＹＫ−３７３（商品名；ＢＹＫケミー社製）があり、ポリエーテル−ポリエステル変性水酸基含有ポリジメチルシロキサンの市販品としては、ＢＹＫ−３７５（商品名；ＢＹＫケミー社製）がある。 A commercially available product of polyester-modified hydroxyl group-containing polydimethylsiloxane is BYK-370 (trade name; manufactured by BYK Chemie), and a commercially available product of polyether-modified hydroxyl group-containing polydimethylsiloxane is BYK-373 (product name: BYK). As a commercially available product of polyether-polyester-modified hydroxyl group-containing polydimethylsiloxane, there is BYK-375 (trade name; manufactured by BYK Chemie).
本発明において、上記水酸基含有ポリジメチルシロキサンと反応して巨大高分子を形成するために使用される多価イソシアネートとしては、例えばトリレンジイソシアナート、パラフェニレンジイソシアナート、２，４−トルエンジイソシアナート、２，６−トルエンジイソシアナート、ヘキサメチレンジイソシアナート、１，４−ナフタレンジイソシアナート、４，４’−ジフェニルジイソシアナート、４，４’−ジフェニルメタンジイソシアナート、３，３’−ジメチル−４，４’−ジフェニルジイソシアナート、３，３’−ジメチル−４，４’−ジフェニルメタンジイソシアナート、３，３’−ジメトキシ−４，４’−ジフェニルジイソシアナート、２−クロロ−１，４−フェニルジイソシアナート、１−クロロ−２，４−フェニレンジイソシアナート、ｍ−フェニレンジイソシアナート、ｐ−フェニレンジイソシアナート、２，２’、５，５’−テトラメチル−４，４’−ｍ−キシリレンジイソシアナート、ω−キシリレンジイソシアナート、ω’−キシリレンジイソシアナート等のジイソシアネート、あるいは該ジイソシアネートとポリエチレンアジペート、ポリテトラヒドロフラン、１，４−ブタンジオール、１，４−シスブテンジオール、１，５−ジヒドロキシエトキシナフタリン、１，４−ブチンジオール、ポリエステル、ポリ（オキシエチレン−プロピレン）ポリオール、アクリルポリオール、ヒマシ油ダイマー、トール油ダイマー等の活性水酸基含有化合物とを反応させたイソシアネート単量体のアダクト体等が使用される。 In the present invention, examples of the polyvalent isocyanate used to form a macromolecule by reacting with the hydroxyl group-containing polydimethylsiloxane include, for example, tolylene diisocyanate, paraphenylene diisocyanate, and 2,4-toluene diisocyanate. Narate, 2,6-toluene diisocyanate, hexamethylene diisocyanate, 1,4-naphthalene diisocyanate, 4,4'-diphenyl diisocyanate, 4,4'-diphenylmethane diisocyanate, 3,3 ' -Dimethyl-4,4'-diphenyl diisocyanate, 3,3'-dimethyl-4,4'-diphenylmethane diisocyanate, 3,3'-dimethoxy-4,4'-diphenyl diisocyanate, 2-chloro -1,4-phenyl diisocyanate, 1-chloro-2,4-phenylene Isocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 2,2 ′, 5,5′-tetramethyl-4,4′-m-xylylene diisocyanate, ω-xylylene diisocyanate, ω Diisocyanates such as' -xylylene diisocyanate, or the diisocyanate and polyethylene adipate, polytetrahydrofuran, 1,4-butanediol, 1,4-cisbutenediol, 1,5-dihydroxyethoxynaphthalene, 1,4-butynediol, An adduct of an isocyanate monomer obtained by reacting an active hydroxyl group-containing compound such as polyester, poly (oxyethylene-propylene) polyol, acrylic polyol, castor oil dimer, tall oil dimer or the like is used.
〔重合性ビニル単量体〕
本発明において、特に重合性ビニル単量体として使用されるのは、ポリオキシプロピレングリコール、ポリオキシプロピレン−ポリオキシエチレングリコール、ポリオキシブチレングリコール、ポリオキシヘキシレングリコール、ポリオキシノニレングリコール等の２価アルコールのアクリル酸および／またはメタクリル酸エステル、トリメチロールプロパン、ヘキサントリオール、グリセリン等の３価アルコールのアクリル酸および／またはメタクリル酸エステルである。上記多価アルコールのアクリル酸および／またはメタクリル酸エステルに加えて、あるいは上記多価アルコールのアクリル酸および／またはメタクリル酸エステルに代えて、ポリエーテルおよび／またはポリエステルと多価イソシアネートとの反応物である片末端または両末端に水酸基を有するポリウレタンにアクリル酸および／またはメタクリル酸をエステル化したポリウレタン（メタ）アクリレートを使用してもよく、更に他の重合性ビニル単量体としては、例えばメチルアクリレート、エチルアクリレート、ｎ−プロピルアクリレート、ｉｓｏ−プロピルアクリレート、ｎ−ブチルアクリレート、ｉｓｏ−ブチルアクリレート、ｔ−ブチルアクリレート、２−エチルヘキシルアクリレート、シクロヘキシルアクリレート、テトラヒドロフルフリルアクリレート、メチルメタクリレート、エチルメタクリレート、ｎ−プロピルメタクリレート、ｉｓｏ−プロピルメタクリレート、ｎ−ブチルメタクリレート、ｉｓｏ−ブチルメタクリレート、２−エチルヘキシルメタクリレート、シクロヘキシルメタクリレート、テトラヒドロフルフリルメタクリレート、ステアリルメタクリレート、ラウリルメタクリレート等の脂肪族または環式アクリレート及び／またはメタクリレート、メチルビニルエーテル、エチルビニルエーテル、ｎ−プロピルビニルエーテル、ｎ−ブチルビニルエーテル、ｉｓｏ−ブチルビニルエーテル等のビニルエーテル類、スチレン、α−メチルスチレン等のスチレン類、アクリロニトリル、メタクリロニトリル等の二トリル系単量体、酢酸ビニル、プロピオン酸ビニル等の脂肪酸ビニル、塩化ビニル、塩化ビニリデン、弗化ビニル、弗化ビニリデン等のハロゲン含有単量体、エチレン、プロピレン等のオレフィン類、イソプレン、クロロプレン、ブタジエン等のジエン類、アクリル酸、メタクリル酸、イタコン酸、マレイン酸、クロトン酸、アトロパ酸、シトラコン酸等のα，β−不飽和カルボン酸、２−ヒドロキシエチルアクリレート、２−ヒドロキシエチルメタクリレート、２−ヒドロキシプロピルアクリレート、２−ヒドロキシプロピルメタクリレート、アリルアルコール等の水酸基含有単量体、アクリルアミド、メタクリルアミド、ジアセトンアクリルアミド等のアミド類、ジメチルアミノエチルアクリレート、ジメチルアミノエチルメタクリレート、ジメチルアミノプロピルアクリレート、ジメチルアミノプロピルメタクリレート等のアミノ基含有単量体、グリシジルアクリレート、グリシジルメタクリレート、グリシジルアリルエーテル等のエポキシ基含有単量体、その他ビニルピロリドン、ビニルピリジン、ビニルカルバゾール等の水溶性単量体、またγ−メタクリロキシプロピルトリメトキシシラン、ビニルトリアセトキシシラン、ｐ−トリメトキシシリルスチレン、ｐ−トリエトキシシリルスチレン、ｐ−トリメトキシシリル−α―メチルスチレン、ｐ−トリエトキシシリル−α−メチルスチレン、γ−アクリロキシプロピルトリメトキシシランン、ビニルトリメトキシシラン、Ｎ−β（Ｎ−ビニルベンジルアミノエチル−γ−アミノプロピル）トリメトキシシラン・塩酸塩等が例示される。
(Polymerizable vinyl monomer)
In the present invention, polyoxypropylene glycol, polyoxypropylene-polyoxyethylene glycol, polyoxybutylene glycol, polyoxyhexylene glycol, polyoxynonylene glycol, etc. are particularly used as the polymerizable vinyl monomer. Acrylic acid and / or methacrylic acid ester of trihydric alcohol such as acrylic acid and / or methacrylic acid ester of dihydric alcohol, trimethylolpropane, hexanetriol, glycerin. In addition to the polyhydric alcohol acrylic acid and / or methacrylic acid ester, or in place of the polyhydric alcohol acrylic acid and / or methacrylic acid ester, a reaction product of a polyether and / or polyester and a polyvalent isocyanate. A polyurethane (meth) acrylate obtained by esterifying acrylic acid and / or methacrylic acid to a polyurethane having a hydroxyl group at one end or both ends may be used, and as another polymerizable vinyl monomer, for example, methyl acrylate , Ethyl acrylate, n-propyl acrylate, iso-propyl acrylate, n-butyl acrylate, iso-butyl acrylate, t-butyl acrylate, 2-ethylhexyl acrylate, cyclohexyl acrylate, tetrahydro Such as rufuryl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, iso-propyl methacrylate, n-butyl methacrylate, iso-butyl methacrylate, 2-ethylhexyl methacrylate, cyclohexyl methacrylate, tetrahydrofurfuryl methacrylate, stearyl methacrylate, lauryl methacrylate, etc. Aliphatic or cyclic acrylates and / or methacrylates, vinyl ethers such as methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, n-butyl vinyl ether, iso-butyl vinyl ether, styrenes such as styrene and α-methyl styrene, acrylonitrile, methacrylate Nitrile monomers such as ronitrile, vinyl acetate, propionic acid Fatty acid vinyl such as vinyl, halogen-containing monomers such as vinyl chloride, vinylidene chloride, vinyl fluoride and vinylidene fluoride, olefins such as ethylene and propylene, dienes such as isoprene, chloroprene and butadiene, acrylic acid and methacrylic acid , Α, β-unsaturated carboxylic acids such as itaconic acid, maleic acid, crotonic acid, atropic acid, citraconic acid, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, Hydroxyl-containing monomers such as allyl alcohol, amides such as acrylamide, methacrylamide, diacetone acrylamide, dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, dimethylaminopropyl acrylate, di Amino group-containing monomers such as methylaminopropyl methacrylate, epoxy group-containing monomers such as glycidyl acrylate, glycidyl methacrylate, and glycidyl allyl ether, other water-soluble monomers such as vinyl pyrrolidone, vinyl pyridine, and vinyl carbazole, and γ -Methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, p-trimethoxysilylstyrene, p-triethoxysilylstyrene, p-trimethoxysilyl-α-methylstyrene, p-triethoxysilyl-α-methylstyrene, γ -Acryloxypropyltrimethoxysilane, vinyltrimethoxysilane, N- [beta] (N-vinylbenzylaminoethyl- [gamma] -aminopropyl) trimethoxysilane, hydrochloride, etc. are exemplified.
〔配合〕
上記重合性（メタ）アクリル基含有ポリジメチルシロキサンは、上記重合性ポリエステルおよび／またはポリエーテル（メタ）アクリレート１００質量部に対して、通常１０〜３０質量部添加される。また水酸基含有ポリジメチルシロキサンは、上記重合性ポリエステルおよび／またはポリエーテル（メタ）アクリレート１００質量部に対して通常７〜１４質量部添加される。更に上記重合性ビニル単量体を添加する場合には、上記重合性ポリエステルおよび／またはポリエーテル（メタ）アクリレート１００質量部に対して、通常５０〜９０質量部添加される。上記成分は通常メタノール、エタノール、ｉｓｏ−プロパノール、ブタノール、シクロヘキサノール等のアルコール系溶剤、アセトン、エチルメチルケトン、イソブチルメチルケトン、シクロヘキサノンのようなケトン系溶剤、酢酸エチル、酢酸ｎ−ブチル、酢酸アミル等のエステル系溶剤、ベンゼン、トルエン、キシレン等の芳香族系溶剤、セロソルブアセテート、メチルセロソルブ、エチルセロソルブ、ｎ−ブチルセロソルブ等のセロソルブ系溶剤、モノフェニルグリコール、プロピレングリコールモノメチルエーテル、ジプロピレングリコールモノメチルエーテル等の多価アルコールのアルキルエーテル等の有機溶剤に溶解され、滑雪性塗料が調整される。
〔塗膜〕
本発明の滑雪性塗料は、例えば合板、ハードボード、木質セメント板、ケイ酸カルシウム板、石膏板、セラミック板、プラスチック板などの表面に塗布され、電子線を照射することによって硬化せしめられ、該表面に滑雪性塗膜を形成する。
該塗膜の厚みは通常５０〜１５０μｍ程度とされ、電子線は通常３〜５ＭＲａｄの強度のものを０．１秒以下の短時間で照射される。
[Combination]
The polymerizable (meth) acryl group-containing polydimethylsiloxane is usually added in an amount of 10 to 30 parts by mass with respect to 100 parts by mass of the polymerizable polyester and / or polyether (meth) acrylate. The hydroxyl group-containing polydimethylsiloxane is added usually 7-14 parts by mass relative to the polymerizable polyester and / or polyether (meth) acrylate 100 parts by mass. Furthermore, when adding the said polymerizable vinyl monomer, 50-90 mass parts is normally added with respect to 100 mass parts of the said polymerizable polyester and / or polyether (meth) acrylate. The above components are usually alcohol solvents such as methanol, ethanol, iso-propanol, butanol, cyclohexanol, ketone solvents such as acetone, ethyl methyl ketone, isobutyl methyl ketone, cyclohexanone, ethyl acetate, n-butyl acetate, amyl acetate. Ester solvents such as benzene, toluene, xylene aromatic solvents, cellosolve acetate, methyl cellosolve, ethyl cellosolve, cellosolve solvents such as n-butyl cellosolve, monophenyl glycol, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether It is dissolved in an organic solvent such as an alkyl ether of a polyhydric alcohol such as a snow-sliding paint.
[Coating]
The snow-sliding paint of the present invention is applied to the surface of, for example, plywood, hard board, wood cement board, calcium silicate board, gypsum board, ceramic board, plastic board, etc., and is cured by irradiation with an electron beam. A snow-sliding coating film is formed on the surface.
The thickness of the coating film is usually about 50 to 150 μm, and the electron beam is usually irradiated with an intensity of 3 to 5 MRad in a short time of 0.1 seconds or less.
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〔実施例１〕
下記の配合物を調整する。
ポリエステルジアクリレート ５８．０質量部
ポリエステル変性アクリル基含有ポリジメチルシロキサン ５．０質量部
ポリエステル変性水酸基含有ポリジメチルシロキサン ５．０質量部
ジプロピレングリコールジアクリレート １５．０質量部
ネオペンチルグリコールジアクリレート １５．０質量部
ヘキサメチレンジイソシアネート １．０質量部
紫外線吸収剤 １．０質量部
上記組成の滑雪性塗料を塗料ＮＯ．１とする。
[Example 1 ]
The following formulation is prepared.
Polyester diacrylate 58.0 parts by weight Polyester-modified acrylic group-containing polydimethylsiloxane 5.0 parts by weight Polyester-modified hydroxyl group-containing polydimethylsiloxane 5.0 parts by weight Dipropylene glycol diacrylate 15.0 parts by weight Neopentyl glycol diacrylate 15. 0 part by mass hexamethylene diisocyanate 1.0 part by mass UV absorber 1.0 part by mass Set to 1 .
〔実施例２〕
下記の配合物を調整する。
ポリエステルジアクリレート ５５．０質量部
ポリエーテル変性アクリル基含有ポリジメチルシロキサン ５．０質量部
ポリエステル変性水酸基含有ポリジメチルシロキサン ５．０質量部
ヘキサメチレンジイソシアネート １．０質量部
ヘキサメチレンジオールジアクリレート １８．０質量部
トリメチロールプロパントリアクリレート １５．０質量部
紫外線吸収剤 １．０質量部
上記組成の滑雪性塗料を塗料ＮＯ．２とする。
[Example 2 ]
The following formulation is prepared.
Polyester diacrylate 55.0 parts by weight Polyether-modified acrylic group-containing polydimethylsiloxane 5.0 parts by weight Polyester-modified hydroxyl group-containing polydimethylsiloxane 5.0 parts by weight Hexamethylene diisocyanate 1.0 part by weight Hexamethylenediol diacrylate 18.0 Parts by weight trimethylolpropane triacrylate 15.0 parts by weight UV absorber 1.0 part by weight 2 .
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上記塗料ＮＯ．１およびＮＯ．２を合板の表面に膜厚約１００μｍに塗布し乾燥した後、電子線回折装置によって３ＭＲａｄ〜５Ｍｒａｄの電子線を０．１秒間照射して該塗膜を硬化せしめた。各塗料の物性を表１に示す。 The above paint NO. 1 and NO. 2 was applied to the surface of the plywood to a thickness of about 100 μm and dried, and then the electron beam diffractometer was irradiated with an electron beam of 3 MRad to 5 Mrad for 0.1 seconds to cure the coating film. Table 1 shows the physical properties of each paint.
〔比較例〕
片末端メタクリル基含有ポリジメチルシロキサンと２−ヒドロキシエチルメタクリレートとの７０：３０質量比共重合体の４０質量％エチルメチルケトン溶液に上記共重合体に対し５質量％のヘキサメチレンジアミンを添加した滑雪性塗料を合板の表面に膜厚約１００μｍに塗布して乾燥後１５０℃１０分間の過熱により塗膜を硬化させた。このようにして作成した比較塗料の物性を表１に示す
[Comparative Example]
Snow sliding in which 5% by mass of hexamethylenediamine is added to a 40% by mass ethyl methyl ketone solution of a 70:30 mass ratio copolymer of dimethyl group-containing polydimethylsiloxane and 2-hydroxyethyl methacrylate. The coating film was hardened by overheating at 150 ° C. for 10 minutes after applying a functional paint to the surface of the plywood to a film thickness of about 100 μm and drying. Table 1 shows the physical properties of the comparative paint thus prepared.
〔試験方法〕
１．光沢保持率
光沢計グロスチェッカー（株式会社佐藤商事製）にて、試験前後の塗膜の光沢を測定し、その試験後の光沢を試験前の光沢で除して光沢保持率とする。
２．滑雪性
評価 ◎ 殆んど残存する
○ 若干残存する
□ 多少残存する
△ 殆んど残存しない
３．接触角
室温（２０±１℃）にて、塗膜上に蒸留水をマイクロシリンジで１滴落とし、光学鏡方式により接触角を測定する（協和界面科学製接触角計；ＤＭ−１００）。
４．着氷力
氷作成用のステンレスリングを試料表面に置き、所定の温度に十分冷却後、５℃の蒸留水を注ぎ、所定時間放置して、氷を凍結させた。その後、ステンレスリングにせん断方向に加重をかけ、材料と凍結面をはく離させる。その時の加重を付着面積で除した値を着氷力（ｋｇｆ／ｃｍ２）とする。
〔Test method〕
1. Gloss retention The gloss of the coating film before and after the test is measured with a gloss meter gloss checker (manufactured by Sato Shoji Co., Ltd.), and the gloss after the test is divided by the gloss before the test to obtain the gloss retention.
2. Snow sliding
Evaluation ◎ Almost remains
○ Some remaining
□ Some remaining
△ Almost no residue. Contact angle At room temperature (20 ± 1 ° C.), one drop of distilled water is dropped on the coating film with a microsyringe, and the contact angle is measured by an optical mirror method (contact angle meter manufactured by Kyowa Interface Science; DM-100).
4). Icing power A stainless steel ring for making ice was placed on the sample surface, cooled sufficiently to a predetermined temperature, distilled water at 5 ° C. was poured, and the ice was frozen by leaving it for a predetermined time. Thereafter, a load is applied to the stainless steel ring in the shearing direction to separate the material from the frozen surface. A value obtained by dividing the weight at that time by the adhesion area is defined as an icing force (kgf / cm 2 ).
表１によれば、本発明の滑雪性塗料は滑雪性に優れかつ耐久性の良好な塗膜を提供するが、比較塗料の塗膜は滑雪性に劣りかつ耐久性も充分ではないことが認められる。 According to Table 1, the snow-sliding paint of the present invention provides a coating film having excellent snow-sliding property and good durability, but the coating film of the comparative paint is inferior in snow-sliding property and insufficient in durability. It is done.
本発明は滑雪性塗膜を形成することが極めて短時間で容易かつ省エネルギー的に行われるので工程が短縮化、合理化され、かつ該塗膜の耐久性も良好であるから、産業上利用可能である。
Since the present invention can form a snow-sliding coating film in an extremely short time easily and energy-saving, the process is shortened and streamlined, and the durability of the coating film is good, so that it can be used industrially. is there.
Claims (2)
The mixture mixture was further added polymerizable vinyl monomer of claim 1 Ri Do a cured product obtained by curing by electron beam irradiation, Namerayuki coating film, characterized in Rukoto that have a surface, such as snow to slide off .
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| JP2006163656A JP5265858B2 (en) | 2006-06-13 | 2006-06-13 | Snow-sliding coating |
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| JP2006163656A JP5265858B2 (en) | 2006-06-13 | 2006-06-13 | Snow-sliding coating |
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| JP2013019007A Division JP5619927B2 (en) | 2013-02-01 | 2013-02-01 | Snow-sliding coating |
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| CN108383967B (en) * | 2018-03-21 | 2020-12-08 | 鲁东大学 | Polyurethane acrylate modified organic silicon prepolymer and preparation method thereof |
| JP7178227B2 (en) * | 2018-09-27 | 2022-11-25 | アイカ工業株式会社 | Photocurable resin composition |
| WO2023058383A1 (en) * | 2021-10-05 | 2023-04-13 | 信越化学工業株式会社 | Rubber particles, composite particles, and manufacturing methods therefor |
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| EP0159683A3 (en) * | 1984-04-23 | 1987-09-02 | DeSOTO, INC. | Electron beam-curable release coatings |
| JPH0696639B2 (en) * | 1988-12-29 | 1994-11-30 | 信越化学工業株式会社 | Organopolysiloxane compound |
| JPH08208773A (en) * | 1995-02-09 | 1996-08-13 | Sekisui Chem Co Ltd | Water-repellent composition |
| JP2002114941A (en) * | 2000-07-31 | 2002-04-16 | Nippon Paint Co Ltd | Curable resin composition for water repellent paint and coated material |
| JP2002256218A (en) * | 2001-03-02 | 2002-09-11 | Mitsunori Yoshida | Composition for preventing snow and ice accretion and member for preventing snow and ice accretion using the same |
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