JPH0334788B2 - - Google Patents
Info
- Publication number
- JPH0334788B2 JPH0334788B2 JP61177137A JP17713786A JPH0334788B2 JP H0334788 B2 JPH0334788 B2 JP H0334788B2 JP 61177137 A JP61177137 A JP 61177137A JP 17713786 A JP17713786 A JP 17713786A JP H0334788 B2 JPH0334788 B2 JP H0334788B2
- Authority
- JP
- Japan
- Prior art keywords
- silicone rubber
- parts
- component
- primer composition
- group
- 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
Links
- 239000000203 mixture Substances 0.000 claims description 25
- -1 titanate ester Chemical class 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229920001296 polysiloxane Polymers 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001282 organosilanes Chemical class 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 claims description 2
- 229920002379 silicone rubber Polymers 0.000 description 25
- 239000004945 silicone rubber Substances 0.000 description 21
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 239000000057 synthetic resin Substances 0.000 description 7
- 229920003002 synthetic resin Polymers 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- 229920002292 Nylon 6 Polymers 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004944 Liquid Silicone Rubber Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910000906 Bronze Inorganic materials 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 239000010974 bronze Substances 0.000 description 3
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002075 main ingredient Substances 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- FDXAEDSUUCCDFG-UHFFFAOYSA-N 16-methylheptadecanoic acid;propan-2-ol;prop-2-enoic acid;titanium Chemical compound [Ti].CC(C)O.OC(=O)C=C.OC(=O)C=C.CC(C)CCCCCCCCCCCCCCC(O)=O FDXAEDSUUCCDFG-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- HJIKNAZVWYQXKZ-UHFFFAOYSA-N bis(2-ethoxyethoxy)silane Chemical compound C(C)OCCO[SiH2]OCCOCC HJIKNAZVWYQXKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- ZXPDYFSTVHQQOI-UHFFFAOYSA-N diethoxysilane Chemical compound CCO[SiH2]OCC ZXPDYFSTVHQQOI-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- CIOXFKGQNIJXKF-UHFFFAOYSA-N tris(2-methoxyethoxy)silane Chemical compound COCCO[SiH](OCCOC)OCCOC CIOXFKGQNIJXKF-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、プライマー組成物に関し、詳しく
は、シリコーンゴムと各種基材とを接着させるに
有効なプライマー組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a primer composition, and more particularly to a primer composition effective for adhering silicone rubber to various substrates.
［従来技術］
従来、シリコーンゴムとプラスチツク、ガラス
金属酸化物、金属などの各種基材とを接着するに
はプライマーが必須とされており、今までオルガ
ノフアンクシヨナルシランを主剤とする種々のプ
ライマーが提案されている。[Prior Art] Conventionally, a primer has been essential for adhering silicone rubber to various base materials such as plastics, glass metal oxides, and metals. is proposed.
［発明が解決しようとする問題点］
しかしながら、基材がプラスチツクのような不
活性な表面を有する場合には、通常のオルガノフ
アンクシヨナルシランを主剤とするプライマーで
は接着性が十分でなく満足できるものではなかつ
た。[Problems to be Solved by the Invention] However, when the base material has an inert surface such as plastic, the adhesion of a primer based on ordinary organofunctional silane is insufficient and is not satisfactory. It wasn't something.
本発明者らは上記の欠点を改良すべく検討した
結果、特定の有機チタン酸エステルを主剤とする
組成物がシリコーンゴムをプラスチツクに接着さ
せるために有効であることを見い出し、すでにこ
れを主成分とするプライマー組成物を提案した
が、しかし、この種のプライマーではシリコーン
ゴムを金属類に接着させるには十分満足できるも
のではなかつた。 As a result of studies to improve the above-mentioned drawbacks, the present inventors discovered that a composition containing a specific organic titanate ester as a main ingredient is effective for adhering silicone rubber to plastic, and has already used this composition as a main ingredient. However, this type of primer was not sufficiently satisfactory for adhering silicone rubber to metals.
そこで、本発明者らは上記の問題点を解消すべ
く検討した結果、特定の有機チタン酸エステルと
１分子中にケイ素原子に直接結合する水素原子を
含有するケイ素化合物からなる組成物が、プライ
マーとしてシリコーンゴムをプラスチツクだけで
はなく、各種金属類にも強固に接着させるに有効
であることを見い出し本発明を完成させた。 Therefore, the present inventors investigated to solve the above problems, and as a result, a composition consisting of a specific organic titanate ester and a silicon compound containing a hydrogen atom directly bonded to a silicon atom in one molecule was developed as a primer. They discovered that silicone rubber is effective in firmly adhering not only plastics but also various metals, and completed the present invention.
本発明の目的はシリコーンゴムと各種基材を接
着させるに有効なプライマー組成物を提供するに
ある。 An object of the present invention is to provide a primer composition that is effective for adhering silicone rubber to various substrates.
［問題点の解決手段とその作用］
上記目的は、
(イ) 一般式
［式中、R1，R2は水素原子またはアルキル
基、R3，R4はアルキル基またはアリール基を
示し、ｌ，ｍ，ｎは１≦ｌ＜４、０≦ｍ＜４、
０≦ｎ＜４、ｌ＋ｍ＋ｎ＝４の整数］
で表わされる有機チタン酸エステル
100重量部
(ロ) １分子中にけい素原子に結合する水素原子を
少なくとも１個有するオルガノシランまたはオ
ルガノポリシロキサン
１〜10000重量部
(ハ) 有機溶剤
任意量
からなるプライマー組成物によつて達成される。[Means for solving problems and their effects] The above objectives are: (a) General formula [In the formula, R 1 and R 2 are hydrogen atoms or alkyl groups, R 3 and R 4 are alkyl groups or aryl groups, and l, m, and n are 1≦l<4, 0≦m<4,
0≦n<4, an integer of l+m+n=4] Organic titanate ester represented by 100 parts by weight (b) Organosilane or organopolysiloxane having at least one hydrogen atom bonded to a silicon atom in one molecule 1 to This can be achieved with a primer composition consisting of an arbitrary amount of 10,000 parts by weight (c) of an organic solvent.
これを説明すると、本発明に使用される(イ)成分
の有機チタン酸エステルは、チタン系カツプリン
グ剤と呼ばれるものであり、接着性を付与するた
めの必須成分である。これは、上式中、R1，R2
が水素原子またはメチル基、エチル基、プロピル
基などで例示されるアルキル基であり、R3，R4
はメチル基、エチル基、プロピル基、イソプロピ
ル基、ブチル基などで例示されるアルキル基また
はフエニル基、トリル基などのアリール基であ
る。ｌ，ｍ，ｎは整数であり、これは１≦ｌ＜
４、０≦ｍ＜４、０≦ｎ＜４、ｌ＋ｍ＋ｎ＝４を
満足する整数である。かかる有機チタン酸エステ
ルとしては、イソプロピルジメタクリルイソステ
アロイルチタネート、イソプロピルジアクリルイ
ソステアロイルチタネート、ジブチルジアクリル
チタネート、ジブチルイソステアロイルメタクリ
ルチタネートが例示される。これらの有機チタン
酸エステルはそれぞれ単独あるいは２種以上混合
物としても使用できる。 To explain this, the organic titanate ester of component (a) used in the present invention is called a titanium-based coupling agent, and is an essential component for imparting adhesive properties. In the above formula, R 1 , R 2
is a hydrogen atom or an alkyl group exemplified by a methyl group, an ethyl group, a propyl group, etc., and R 3 , R 4
is an alkyl group such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, or an aryl group such as a phenyl group or a tolyl group. l, m, n are integers, which is 1≦l<
4, 0≦m<4, 0≦n<4, l+m+n=4. Examples of such organic titanate esters include isopropyl dimethacrylylisostearoyl titanate, isopropyl diacryl isostearoyl titanate, dibutyl diacryl titanate, and dibutyl isostearoyl methacrylic titanate. These organic titanate esters can be used alone or as a mixture of two or more.
本発明に使用される(ロ)成分のオルガノシランま
たはオルガノポリシロキサンは接着性を顕著に向
上させるための重要な成分である。かかる(ロ)成分
は平均単位式
（式中、R5は置換または非置換の一価炭化水
素基であり、これにはメチル基、エチル基、プロ
ピル基、オクチル基などのアルキル基、フエニル
基などのアリール基およびこれらの基の水素原子
をハロゲン原子、シアノ基などで置換したものが
例示される。R6はメチル基、エチル基、プロピ
ル基などのアルキル基；フエニル基などのアリー
ル基；２−メトキシエチル基、２−エトキシエチ
ル基などのアルコキシアルキル基から選択される
１価の有機基である。ｘは１≦ｘ＜３、ｙは０≦
ｙ＜３、ｚは０≦ｚ≦３、ただし０＜ｘ＋ｙ＋ｚ
≦４である。）で示される有機けい素化合物であ
る。これには、トリアルコキシシラン、ジアルコ
キシシランおよびこれらの部分加水分解縮合物、
オルガノハイドロジエンポリシロキサンなどが含
まれる。使用に際しては(ロ)成分の１種を使用する
か、または２種以上を混合して使用する。この配
合割合は(イ)成分100重量部に対して１〜10000重量
部の範囲、好ましくは１〜100重量部、さらに好
ましくは１〜20重量部である。 Component (b) organosilane or organopolysiloxane used in the present invention is an important component for significantly improving adhesiveness. This (b) component is an average unit equation (In the formula, R 5 is a substituted or unsubstituted monovalent hydrocarbon group, including alkyl groups such as methyl, ethyl, propyl, and octyl, aryl groups such as phenyl, and Examples include those in which a hydrogen atom is substituted with a halogen atom, a cyano group, etc. R 6 is an alkyl group such as a methyl group, an ethyl group, or a propyl group; an aryl group such as a phenyl group; a 2-methoxyethyl group or a 2-ethoxy group; It is a monovalent organic group selected from alkoxyalkyl groups such as ethyl group. x is 1≦x<3, y is 0≦
y<3, z is 0≦z≦3, but 0<x+y+z
≦4. ) is an organosilicon compound represented by This includes trialkoxysilanes, dialkoxysilanes and their partially hydrolyzed condensates,
These include organohydrodiene polysiloxanes, etc. When used, one type of component (b) may be used, or two or more types may be used in combination. The mixing ratio is in the range of 1 to 10,000 parts by weight, preferably 1 to 100 parts by weight, and more preferably 1 to 20 parts by weight, per 100 parts by weight of component (a).
(ロ)成分の具体例をあげると、例えばトリメトキ
シシラン、トリエトキシシラン、トリ（β−メト
キシエトキシ）シラン、メチルジメトキシシラ
ン、メチルジエトキシシラン、ジエトキシシラ
ン、ジ（β−エトキシエトキシ）シランおよびこ
れらのシランの部分加水分解縮合物、メチルハイ
ドロジエンポリシロキサン、メチルハイドロジエ
ンポリシロキサン・ジメチルポリシロキサン共重
合体が挙げられる。(ロ)成分は単独で使用してもよ
いし２種以上の混合物として使用してもよい。 Specific examples of component (b) include trimethoxysilane, triethoxysilane, tri(β-methoxyethoxy)silane, methyldimethoxysilane, methyldiethoxysilane, diethoxysilane, di(β-ethoxyethoxy)silane. and partially hydrolyzed condensates of these silanes, methylhydrodienepolysiloxane, and methylhydrodienepolysiloxane/dimethylpolysiloxane copolymers. Component (b) may be used alone or as a mixture of two or more.
本発明に使用される(ハ)成分は、(イ)成分および(ロ)
成分を溶解させるための有機溶剤であり、これは
(イ)成分および(ロ)成分の溶解性およびプライマーの
塗布作業の蒸発性を考慮して選択されるが、例え
ば、トルエン、キシレン、ベンゼンなどの芳香族
炭化水素、ヘキセンやシクロヘキサンなどの低級
パラフイン類、メチルエチルケトン、アセトンな
どのケトン類、エタノールやイソプロピルアルコ
ールなどのアルコール類、トリクロルエチレンな
どの塩素系溶剤が例示される。これらの有機溶剤
は単独もしくは２種以上の混合溶剤として使用す
ることも可能である。 Component (c) used in the present invention includes component (a) and (b)
An organic solvent for dissolving ingredients;
They are selected taking into consideration the solubility of components (a) and (b) and the evaporability of the primer application process, but examples include aromatic hydrocarbons such as toluene, xylene, and benzene, and lower paraffins such as hexene and cyclohexane. Examples include ketones such as methyl ethyl ketone and acetone, alcohols such as ethanol and isopropyl alcohol, and chlorinated solvents such as trichlorethylene. These organic solvents can be used alone or as a mixed solvent of two or more.
(ハ)成分の配合割合は特に限定されないが、(イ)お
よび(ロ)成分の溶解性および溶解物の粘度、塗布作
業性を考慮して適宜選択すればよい。一般には、
(イ)および(ロ)成分100重量部に対して100重量部〜
2000重量部の範囲内にあることが好ましい。 The blending ratio of component (c) is not particularly limited, but may be appropriately selected in consideration of the solubility of components (a) and (b), the viscosity of the dissolved product, and coating workability. In general,
100 parts by weight or more per 100 parts by weight of components (a) and (b)
It is preferably within the range of 2000 parts by weight.
本発明のプライマー組成物は、(イ)成分、(ロ)成分
および(ハ)成分を単に均一に混合するだけで容易に
得られる。 The primer composition of the present invention can be easily obtained by simply uniformly mixing components (a), (b), and (c).
また、本発明のプライマー組成物においては、
必要に応じて(イ)〜(ハ)成分以外に各種の添加物、例
えばオルガノフアンクシヨナルシラン、珪酸エス
テル、オルガノポリシロキサンなどの有機けい素
化合物、フユームドシリカ、沈降法シリカ、石英
粉末、けいそう土、炭酸カルシウム、ベンガラ、
アルミナなどの無機質充填剤、各種耐熱剤、有機
過酸化物とは、着色剤を添加配合することは、本
発明の目的を損わない限り任意とされる。 Furthermore, in the primer composition of the present invention,
If necessary, various additives may be added in addition to components (a) to (c), such as organosilicon compounds such as organofunctional silanes, silicate esters, and organopolysiloxanes, fumed silica, precipitated silica, quartz powder, and silica. soil, calcium carbonate, red iron,
Inorganic fillers such as alumina, various heat resistant agents, and organic peroxides may optionally be mixed with colorants as long as the purpose of the present invention is not impaired.
本発明のプライマー組成物は、使用にあたつて
被着体に塗布後、30分間またはそれ以上周乾を行
なつてからシリコーンゴム組成物を適用すること
が好ましく、場合によつてはプライマー組成物の
被着体に対する接着性を確実にするため加熱下で
乾燥することもできる。 In use, the primer composition of the present invention is preferably applied to an adherend and then allowed to dry for 30 minutes or more before applying the silicone rubber composition. It can also be dried under heat to ensure adhesion of the article to the adherend.
本発明のプライマー組成物は、シリコーンゴム
組成物を硬化させつつそれと接触している基材に
接着させるためのプライマーとして使用すると、
ナイロン６樹脂、ナイロン66樹脂、ABS樹脂、
ポリカーボネート樹脂、ポリアセタール樹脂、ポ
リエステル樹脂、アクリル樹脂、フエノール樹脂
等の合成樹脂材料および、鉄、ステンレス、ニツ
ケル、アルミニウム、りん青銅等の金属材料の表
面にシリコーンゴムを強固に接着させることがで
きる。 When the primer composition of the present invention is used as a primer for curing a silicone rubber composition and adhering it to a substrate that is in contact with the silicone rubber composition,
Nylon 6 resin, nylon 66 resin, ABS resin,
Silicone rubber can be firmly adhered to the surfaces of synthetic resin materials such as polycarbonate resin, polyacetal resin, polyester resin, acrylic resin, and phenol resin, and metal materials such as iron, stainless steel, nickel, aluminum, and phosphor bronze.
［実施例］
次に実施例により本発明を説明する。実施例中
部とあるのは重量部を示す。[Example] Next, the present invention will be explained with reference to Examples. "Example Middle" indicates parts by weight.
実施例 １
イソプロピルジアクリルイソステアロイルチタ
ネート〔味の素(株)製プレンアクト11〕10部および
メチルハイドロジエンポリシロキサン20部をトル
エン90部に溶解させプライマー組成物を調整し
た。このプライマー組成物をナイロン６樹脂、ナ
イロン66樹脂、ポリカーボネート樹脂および
ABS樹脂の４種の合成樹脂板および、鉄、ステ
ンレス、アルミニウム、りん青銅の４種の金属板
にそれぞれ塗布し、室温にて60分間放置して風乾
させた。次いで、このプライマーを塗布した合成
樹脂板および金属板を金型に入れ、その上から付
加反応型液状シリコーンゴム〔トーレ・シリコー
ン(株)製SE6706〕を流し込み、圧力25Kg／cm2、温
度100℃の条件下で10分間加圧加熱し、液状シリ
コーンゴムを硬化させたところ、シリコーンゴム
と合成樹脂板およびシリコーンゴムと金属板が強
固に接着した試験板が得られた。得られた試験板
についてJIS−Ｋ−6744の方法に従つて180度剥離
試験を行ない接着状態を調べたところ、いずれも
完全に接着しており、剥離試験後の破断面の状態
は100％凝集破壊（シリコーンゴム部分で破断）
であつた。Example 1 A primer composition was prepared by dissolving 10 parts of isopropyl diacrylic isostearoyl titanate (Plenact 11, manufactured by Ajinomoto Co., Inc.) and 20 parts of methylhydrodiene polysiloxane in 90 parts of toluene. This primer composition is applied to nylon 6 resin, nylon 66 resin, polycarbonate resin and
It was applied to four types of synthetic resin plates (ABS resin) and four types of metal plates (iron, stainless steel, aluminum, and phosphor bronze), and left to air dry at room temperature for 60 minutes. Next, the synthetic resin plate and metal plate coated with this primer were placed in a mold, and an addition reaction type liquid silicone rubber (SE6706 manufactured by Toray Silicone Co., Ltd.) was poured onto the mold at a pressure of 25 kg/cm 2 and a temperature of 100°C. When the liquid silicone rubber was cured by heating under pressure for 10 minutes, a test plate was obtained in which the silicone rubber and the synthetic resin plate and the silicone rubber and the metal plate were firmly adhered. The obtained test plates were subjected to a 180 degree peel test according to the method of JIS-K-6744 to examine the adhesion state, and both were found to be completely adhered, and the state of the fractured surface after the peel test was 100% cohesive. Destruction (breakage at silicone rubber part)
It was hot.
実施例 ２
イソプロピルジメタクリルイソステアロイルチ
タネート〔味の素(株)製プレンアクト７〕10部およ
びトリエトキシシラン40部とをトルエン80部に溶
解させプライマー組成物を調整した。このプライ
マー組成物をナイロン６樹脂、ナイロン66樹脂、
ポリカーボネート樹脂およびABS樹脂の４種の
合成樹脂板および鉄、ステンレス、アルミニウ
ム、りん青銅の４種の金属板にそれぞれ塗布し、
室温にて60分間放置して風乾させた。次いで、こ
の合成樹脂板および金属板を金型に入れ、その上
から付加反応型液状シリコーンゴム〔トーレ・シ
リコーン(株)製SE6706〕を流し込み、圧力25Kg／
cm2、温度100℃の条件下で10分間加圧加熱し、液
状シリコーンゴムを硬化させたところ、シリコー
ンゴムと合成樹脂板およびシリコーンゴムと金属
板が強固に接着した試験板が得られた。得られた
試験板についてJIS−Ｋ−6744の方法に従つて180
度剥離試験を行ない接着状態を調べたところ、い
ずれも完全に接着しており、剥離試験後の破断面
の状態は100％凝集破壊（シリコーンゴム部分で
破断）であつた。Example 2 A primer composition was prepared by dissolving 10 parts of isopropyl dimethacrylylisostearoyl titanate (Plenact 7, manufactured by Ajinomoto Co., Inc.) and 40 parts of triethoxysilane in 80 parts of toluene. This primer composition is applied to nylon 6 resin, nylon 66 resin,
It is applied to four types of synthetic resin plates: polycarbonate resin and ABS resin, and four types of metal plates: iron, stainless steel, aluminum, and phosphor bronze.
It was left to air dry for 60 minutes at room temperature. Next, the synthetic resin plate and metal plate were placed in a mold, and an addition reaction type liquid silicone rubber (SE6706 manufactured by Toray Silicone Co., Ltd.) was poured over the mold, and the pressure was 25 kg/
When the liquid silicone rubber was cured by heating under pressure for 10 minutes at a temperature of 100° C., a test plate was obtained in which the silicone rubber and the synthetic resin plate and the silicone rubber and the metal plate were firmly adhered. The obtained test plate was subjected to 180% according to the method of JIS-K-6744.
When a peel test was performed to examine the adhesion state, all were completely adhered, and the state of the fractured surface after the peel test was 100% cohesive failure (breakage at the silicone rubber part).
実施例 ３
実施例２で得たプライマー組成物をナイロン６
樹脂板および鉄、ステンレス、アルミニウムの金
属板に塗布し、室温にて60分間放置し風乾させ
た。次いで架橋剤として0.5％の２，５ジメチル
２，５ジ（ｔ−ブチルパーオキシ）ヘキサンを添
加したシリコーンゴムコンパウンド〔トーレ・シ
リコーン(株)製SH52U〕の厚さ４mmの未加硫成形
物を上記プライマー塗布面に密着させ、圧力25
Kg／cm2、温度120℃の条件下で10分間加圧加熱し、
シリコーンゴムを硬化させたところ、シリコーン
ゴムとナイロン６樹脂板およびシリコーンゴムと
金属板が強固に接着した試験板が得られた。Example 3 The primer composition obtained in Example 2 was coated with nylon 6
It was applied to resin plates and metal plates made of iron, stainless steel, and aluminum, and left to air dry at room temperature for 60 minutes. Next, a 4 mm thick unvulcanized molded product of a silicone rubber compound [SH52U manufactured by Toray Silicone Co., Ltd.] to which 0.5% of 2,5 dimethyl 2,5 di(t-butylperoxy)hexane was added as a crosslinking agent was molded. Closely apply the primer to the surface coated with the above primer, and apply pressure 25.
Kg/cm 2 and heated under pressure for 10 minutes at a temperature of 120°C.
When the silicone rubber was cured, test plates were obtained in which the silicone rubber and the nylon 6 resin plate and the silicone rubber and the metal plate were firmly adhered to each other.
［発明の効果］
本発明では、(イ)成分の特定の有機チタン酸エス
テルおよび(ロ)成分の１分子中にけい素原子に結合
する水素原子を少なくとも１個有するオルガノシ
ランまたはオルガノポリシロキサンおよび(ハ)成分
の有機溶剤からなるプライマー組成物なのでシリ
コーンゴム用プライマーとして使用した場合には
プラスチツク、金属等各種基材に対して強固に接
着させることができるという特徴を有する。[Effects of the Invention] In the present invention, component (a) is a specific organic titanate ester, component (b) is an organosilane or organopolysiloxane having at least one hydrogen atom bonded to a silicon atom in one molecule, and Since the primer composition is composed of an organic solvent as component (c), it has the characteristic that when used as a primer for silicone rubber, it can firmly adhere to various base materials such as plastics and metals.
Claims (1)
基、R3，R4はアルキル基またはアリール基を
示し、ｌ，ｍ，ｎは１≦ｌ＜４、０≦ｍ＜４、
０≦ｎ＜４、ｌ＋ｍ＋ｎ＝４の整数］ で表わされる有機チタン酸エステル 100重量部 (ロ) １分子中にけい素原子に結合する水素原子を
少なくとも１個有するオルガノシランまたはオ
ルガノポリシロキサン １〜10000重量部 (ハ) 有機溶剤 任意量 からなるプライマー組成物。 ２ (イ)成分のR1およびR2が水素原子である特許
請求の範囲第１項記載のプライマー組成物。 ３ (イ)成分のR1が水素原子でR2がメチル基であ
る特許請求の範囲第１項記載のプライマー組成
物。[Claims] 1 (a) General formula [In the formula, R 1 and R 2 are hydrogen atoms or alkyl groups, R 3 and R 4 are alkyl groups or aryl groups, and l, m, and n are 1≦l<4, 0≦m<4,
0≦n<4, an integer of l+m+n=4] Organic titanate ester represented by 100 parts by weight (b) Organosilane or organopolysiloxane having at least one hydrogen atom bonded to a silicon atom in one molecule 1 to 10,000 parts by weight (c) A primer composition consisting of an arbitrary amount of organic solvent. 2. The primer composition according to claim 1, wherein R 1 and R 2 of component (a) are hydrogen atoms. 3. The primer composition according to claim 1, wherein R 1 of component (a) is a hydrogen atom and R 2 is a methyl group.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61177137A JPS6333474A (en) | 1986-07-28 | 1986-07-28 | Primrer composition |
| US07/029,123 US4749741A (en) | 1986-04-07 | 1987-03-23 | Primer composition |
| DE8787302974T DE3769836D1 (en) | 1986-04-07 | 1987-04-06 | PRIMER COMPOSITION. |
| EP87302974A EP0244952B1 (en) | 1986-04-07 | 1987-04-06 | Primer composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61177137A JPS6333474A (en) | 1986-07-28 | 1986-07-28 | Primrer composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6333474A JPS6333474A (en) | 1988-02-13 |
| JPH0334788B2 true JPH0334788B2 (en) | 1991-05-23 |
Family
ID=16025827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61177137A Granted JPS6333474A (en) | 1986-04-07 | 1986-07-28 | Primrer composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6333474A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10520695B2 (en) | 2013-12-18 | 2019-12-31 | CommScope Connectivity Belgium BVBA | Cable fixation devices and methods |
| US11314030B2 (en) | 2017-10-09 | 2022-04-26 | CommScope Connectivity Belgium BVBA | Cable fixation devices and methods |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2945754A1 (en) | 2009-05-20 | 2010-11-26 | Total Raffinage Marketing | NEW ADDITIVES FOR TRANSMISSION OILS |
-
1986
- 1986-07-28 JP JP61177137A patent/JPS6333474A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10520695B2 (en) | 2013-12-18 | 2019-12-31 | CommScope Connectivity Belgium BVBA | Cable fixation devices and methods |
| US11073673B2 (en) | 2013-12-18 | 2021-07-27 | CommScope Connectivity Belgium BVBA | Cable fixation devices and methods |
| US11314030B2 (en) | 2017-10-09 | 2022-04-26 | CommScope Connectivity Belgium BVBA | Cable fixation devices and methods |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6333474A (en) | 1988-02-13 |
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