JPS6327505A - Polymerizable composition - Google Patents
Polymerizable compositionInfo
- Publication number
- JPS6327505A JPS6327505A JP16959586A JP16959586A JPS6327505A JP S6327505 A JPS6327505 A JP S6327505A JP 16959586 A JP16959586 A JP 16959586A JP 16959586 A JP16959586 A JP 16959586A JP S6327505 A JPS6327505 A JP S6327505A
- Authority
- JP
- Japan
- Prior art keywords
- polymerizable composition
- long period
- adhesive
- color
- thiourea
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 12
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 9
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000013522 chelant Substances 0.000 claims abstract description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract 2
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 abstract description 10
- 239000000853 adhesive Substances 0.000 abstract description 8
- 230000001070 adhesive effect Effects 0.000 abstract description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 7
- 229920006305 unsaturated polyester Polymers 0.000 abstract description 4
- MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 abstract description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract description 2
- 238000005266 casting Methods 0.000 abstract description 2
- GMEGXJPUFRVCPX-UHFFFAOYSA-N butylthiourea Chemical compound CCCCNC(N)=S GMEGXJPUFRVCPX-UHFFFAOYSA-N 0.000 abstract 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 abstract 1
- -1 butylthiourea Chemical compound 0.000 abstract 1
- 208000024335 physical disease Diseases 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000000945 filler Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFFQABQEJATQAT-UHFFFAOYSA-N N,N'-dibutylthiourea Chemical compound CCCCNC(=S)NCCCC KFFQABQEJATQAT-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
Landscapes
- Polymerization Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
この発明はビニルモノマーを含有する重合性の二液混合
系接着剤、不飽和ポリエステル注型材等の重合性組成物
に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a polymerizable composition containing a vinyl monomer, such as a polymerizable two-component adhesive or an unsaturated polyester casting material.
アクリル酸エステル等のビニルモノマーヲ含有する接着
剤主剤や、スチレンモノマー等を含有する不飽和ポリエ
ステル等の重合性組成物を常温でラジカル重合せしめる
ためには過酸化物等のラジカル重合触媒のほかに重合促
進剤を添加する必要があった。従来重合促進剤としてア
ミン類、金属石鹸類を用いる多くの提案があるが、その
ほとんどが硬化後の時間の経過により発生する着色現象
の大きな原因となっている。In order to radically polymerize adhesive base materials containing vinyl monomers such as acrylic acid esters and polymerizable compositions such as unsaturated polyesters containing styrene monomers at room temperature, in addition to radical polymerization catalysts such as peroxides, it is necessary to use radical polymerization catalysts such as peroxides. It was necessary to add a polymerization accelerator. There have been many proposals to use amines and metal soaps as polymerization accelerators, but most of them are a major cause of coloring phenomena that occur over time after curing.
例えば、過酸化ベンゾイルとジメチルアニリンの組合せ
、あるいはメチルエチルケトンパーオキシドとナフテン
酸コバルトの組合せが汎用されているが、前者はジメチ
ルアニリンの添加量を減じると硬化体の着色は少なくな
るが、日光により変色し易い欠点があり、後者はコバル
トの影響で橙色に着色する欠点がある。For example, a combination of benzoyl peroxide and dimethylaniline, or a combination of methyl ethyl ketone peroxide and cobalt naphthenate is widely used, but with the former, reducing the amount of dimethylaniline added reduces the coloring of the cured product, but it changes color due to sunlight. The latter has the disadvantage of being colored orange due to the influence of cobalt.
この発明は上記問題点に着目しなされたものである。そ
の目的は重合体が着色し難く、パネル等の接着に用い目
地等に露出しても目地の違和感を感じない接着剤、ある
いは長期色彩が変化せず長期間美観を維持できる注型物
等に用い好適な重合性組成物を提案するにある。This invention has been made in view of the above-mentioned problems. The purpose of this is to create adhesives whose polymers are difficult to color and which are used to bond panels, etc. and do not cause any discomfort in the joints even when exposed to the joints, or cast products that do not change color over a long period of time and maintain their beauty over a long period of time. The purpose of the present invention is to propose a polymerizable composition suitable for use.
この重合性組成物は、ビニル単量体を含有する主材、ラ
ジカル重合触媒および重合促進剤を混合してなる重合性
組成物において、重合促進剤に金属キレート化合物およ
びチオ尿素類が配合してあることを特徴とする。This polymerizable composition is a polymerizable composition in which a main material containing a vinyl monomer, a radical polymerization catalyst, and a polymerization accelerator are mixed, and a metal chelate compound and a thiourea are blended into the polymerization accelerator. characterized by something.
この組成物においてラジカル重合触媒としては通常過酸
化物を用いる。金属キレート化合物は様々なものが用い
られるがバナジウムアセチルアセトネート等エノール型
化合物が好ましい。In this composition, a peroxide is usually used as the radical polymerization catalyst. Various metal chelate compounds can be used, but enol-type compounds such as vanadium acetylacetonate are preferred.
チオ尿素類としてはジブチルチオ尿素等その誘導体があ
る。Thioureas include dibutylthiourea and other derivatives thereof.
この重合体組成物のビニル単量体を含有する主材とは、
ビニル単量体単体または２種以上の単体混合物溶液、ビ
ニル重合体あるいは不飽和ポリエステル重合体のビニル
単量体溶液等であり、必要に応じ充填剤、顔・染料、あ
るいは安定剤等が添加される。ビニル単量体としては通
常、アクリル酸エステル類、ヌクアクリル酸エステル類
、アクリロニトリル、スチレン等の常温で液相のものが
主として用いられる。The main material containing the vinyl monomer of this polymer composition is:
A solution of a single vinyl monomer or a mixture of two or more monomers, a vinyl monomer solution of a vinyl polymer or an unsaturated polyester polymer, etc., and fillers, pigments, dyes, or stabilizers may be added as necessary. Ru. As vinyl monomers, those that are liquid at room temperature, such as acrylic esters, nucleated acrylic esters, acrylonitrile, and styrene, are generally used.
〔作用〕
この組成物は常温でラジカル重合反応を開始し重合体と
なる。この重合体は着色しがたく、長期にわたり変色を
起さない。[Function] This composition starts a radical polymerization reaction at room temperature and becomes a polymer. This polymer is resistant to staining and does not change color over a long period of time.
主 材：メチルメタクリレート単量体 ６９ 重量部
スチレン単量体 ３．８〃
ステアリン酸処理した水酸化
マグネシウム（充填剤） ２７．２ ｇ重合
触媒： クメンハイド０／マーオキサイド ３ 重量
部（７３％アセトン溶ｉ）
重合促進剤：バナジウムアセチルアセトネートｏ、ｏｏ
ａｓ重量部ジブチルチオ尿素 ２．６ 重量部
上記主材１００重量部に重合促進剤（２，６０８５重量
部）を予め添加混合して混合物をつくり、この混合物に
重合触媒（３重量部）を添加、攪拌した。この組成物は
常温で重合を開始し重合体が得られた。Main material: Methyl methacrylate monomer 69 parts by weight Styrene monomer 3.8 Stearic acid-treated magnesium hydroxide (filler) 27.2 g Polymerization catalyst: Cumenhide 0/mer oxide 3 parts by weight (73% acetone solution) i) Polymerization accelerator: vanadium acetylacetonate o, oo
as parts by weight dibutylthiourea 2.6 parts by weight A polymerization accelerator (2,6085 parts by weight) is added and mixed in advance to 100 parts by weight of the above main material to prepare a mixture, and a polymerization catalyst (3 parts by weight) is added to this mixture. Stirred. This composition started polymerization at room temperature and a polymer was obtained.
この重合体はパネルの目地接着剤として用い、充分高い
接着強度（平均１３０Ｋｇ／、２）を発揮し、着色しが
たく、長期にわたり目地の違和感を感ぜず、壁面の美粧
性を維持した。なお、この実施例で用いた充填剤は重合
体に均質に分散しアイポリの色調を出し、パネル色調と
マツチした目地を形成するのに寄与した。This polymer was used as a joint adhesive for panels, and exhibited sufficiently high adhesive strength (average 130 kg/2), was resistant to staining, did not cause discomfort at the joints over a long period of time, and maintained the aesthetic appearance of walls. The filler used in this example was homogeneously dispersed in the polymer, contributing to the creation of an eye-polished color tone and the formation of joints that matched the panel color tone.
この発明は以上の通りである。この重合性組成物は常温
で重合し、重合体は着色ｓ色を起し難い。従ってこの組
成物はパネル、タイル等の目地接着剤、あるいはパネル
その他の注型重合成形物等原料に用い美粧性を高める上
で効果が犬である。This invention is as described above. This polymerizable composition polymerizes at room temperature, and the polymer is hardly colored. Therefore, this composition can be used as a joint adhesive for panels, tiles, etc., or as a raw material for panels and other cast-polymerized molded products, and can be used to improve cosmetic properties.
Claims (1)
および重合促進剤を混合してなる重合性組成物において
、重合促進剤に金属キレート化合物およびチオ尿素類が
配合してあることを特徴とする重合性組成物。(1) A polymerizable composition formed by mixing a main material containing a vinyl monomer, a radical polymerization catalyst, and a polymerization accelerator, characterized in that the polymerization accelerator contains a metal chelate compound and a thiourea. A polymerizable composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16959586A JPS6327505A (en) | 1986-07-18 | 1986-07-18 | Polymerizable composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16959586A JPS6327505A (en) | 1986-07-18 | 1986-07-18 | Polymerizable composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6327505A true JPS6327505A (en) | 1988-02-05 |
Family
ID=15889400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16959586A Pending JPS6327505A (en) | 1986-07-18 | 1986-07-18 | Polymerizable composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6327505A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2233544A1 (en) * | 2009-03-25 | 2010-09-29 | GC Corporation | Polymerizable composition |
| EP2425808A1 (en) * | 2010-09-03 | 2012-03-07 | GC Corporation | Polymerizable composition |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53139690A (en) * | 1977-05-11 | 1978-12-06 | Denki Kagaku Kogyo Kk | Curing accelerator |
-
1986
- 1986-07-18 JP JP16959586A patent/JPS6327505A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53139690A (en) * | 1977-05-11 | 1978-12-06 | Denki Kagaku Kogyo Kk | Curing accelerator |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2233544A1 (en) * | 2009-03-25 | 2010-09-29 | GC Corporation | Polymerizable composition |
| US8247470B2 (en) | 2009-03-25 | 2012-08-21 | Gc Corporation | Polymerizable composition |
| EP2425808A1 (en) * | 2010-09-03 | 2012-03-07 | GC Corporation | Polymerizable composition |
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