JPH0388816A - Silicone-modified vinyl ester resin and production thereof - Google Patents
Silicone-modified vinyl ester resin and production thereofInfo
- Publication number
- JPH0388816A JPH0388816A JP18372689A JP18372689A JPH0388816A JP H0388816 A JPH0388816 A JP H0388816A JP 18372689 A JP18372689 A JP 18372689A JP 18372689 A JP18372689 A JP 18372689A JP H0388816 A JPH0388816 A JP H0388816A
- Authority
- JP
- Japan
- Prior art keywords
- vinyl ester
- ester resin
- formula
- acid
- silicone
- 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
- 229920005989 resin Polymers 0.000 title claims abstract description 29
- 239000011347 resin Substances 0.000 title claims abstract description 29
- 229920001567 vinyl ester resin Polymers 0.000 title claims description 25
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 10
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims abstract description 8
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims abstract description 8
- 229930016911 cinnamic acid Natural products 0.000 claims abstract description 8
- 235000013985 cinnamic acid Nutrition 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- -1 cinnamoyl group Chemical group 0.000 claims description 4
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003365 glass fiber Substances 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 239000011253 protective coating Substances 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
ビスフェノールＡ型ビニルエステル樹脂は、接着性にす
ぐれ、その硬化物は、耐熱性、耐薬品性、耐候性、電気
的性質、機械的性質がよいことから、接着剤、塗装材、
保護コーテイング材など、広い範囲に用いられている。[Detailed description of the invention] [Field of industrial application] Bisphenol A type vinyl ester resin has excellent adhesive properties, and its cured product has excellent heat resistance, chemical resistance, weather resistance, electrical properties, and mechanical properties. Because of its good properties, adhesives, coating materials,
It is used in a wide range of applications, including as a protective coating material.
シロキサン結合を有する化合物やシリコーン樹脂は、一
般に、可撓性、撥水性、耐熱性、気体透過性、耐ＲｒＥ
性などが、著しく向上する。Compounds and silicone resins having siloxane bonds generally have flexibility, water repellency, heat resistance, gas permeability, and RrE resistance.
Sexuality etc. are significantly improved.
本発明のシリコーン変性ビニルエステル樹脂は、新規な
化合物である。芳香環とシロキサン結合の両方を有する
ので、ビスフェノールＡ型ビニルエステル樹脂の性質と
シリコーン樹脂の特性とを兼ね備えている。よって、ビ
ニルエステル樹脂が用いられている分野への利用はもち
ろんのこと、さらに、シロキサン結合の特性をいかした
新規な用途への発展性をもっている。The silicone-modified vinyl ester resin of the present invention is a novel compound. Since it has both an aromatic ring and a siloxane bond, it has both the properties of bisphenol A vinyl ester resin and that of silicone resin. Therefore, it can be used not only in fields where vinyl ester resins are used, but also in new applications that take advantage of the characteristics of siloxane bonds.
ビニルエステル樹脂は、ソルダーレジスト（耐ハンダ塗
料）、絶縁塗料、保護コーテイング材をはじめとした多
くの分野で使用されている。−船釣に、本樹脂の要求性
能は、用途により多少異なるが、耐熱性、接着性、耐食
性、電気的性質の向上と、低硬化収縮などがあげられる
。Vinyl ester resins are used in many fields, including solder resists (solder-resistant paints), insulation paints, and protective coatings. - For boat fishing, the required performance of this resin varies somewhat depending on the application, but includes improvements in heat resistance, adhesiveness, corrosion resistance, electrical properties, and low curing shrinkage.
従来、光ファイバーの保護コーティングには、シリコー
ン樹脂を用いる熱硬化法によっておこなわれていた。し
かし、硬化時間が長く、生産性に乏しいという欠点があ
った。Conventionally, protective coatings for optical fibers have been applied using a thermosetting method using silicone resin. However, it has the drawbacks of long curing time and poor productivity.
最近、ビニルエステル樹脂をもちいた、光硬化による高
速コーティング法が注目されているが、硬化時の収縮が
大きいことや、親水性が高いという欠点があった。Recently, high-speed photo-curing coating methods using vinyl ester resins have been attracting attention, but they have drawbacks such as large shrinkage during curing and high hydrophilicity.
本発明は、芳香環とシロキサン結合を有する新規なシリ
コーン変性ビニルエステル樹脂とその製造方法を提供す
る０本発明の化合物は、ビスフェノールＡ型ビニルエス
テル樹脂の性質と、シロキサン結合を有する化合物特有
の性質の両方を兼ね備えたものであり、従来のビニルエ
ステル樹脂の用途分野はもとより、より高性能なビニル
エステル樹脂として、新規な分野への発展性を有するも
のである。The present invention provides a novel silicone-modified vinyl ester resin having an aromatic ring and a siloxane bond, and a method for producing the same. It has the potential to be used not only in conventional vinyl ester resin application fields, but also in new fields as a higher performance vinyl ester resin.
本発明は、−数式（１）で示される新規なビニルエステ
ル樹脂及びその製造方法に関するものである。The present invention relates to a novel vinyl ester resin represented by formula (1) and a method for producing the same.
３
「
式（１）中、Ｒ＋およびＲ３は、水素、メチル基、Ｃｔ
またはＢｒであり、相互に同一であっても異なってもよ
い、Ｒ１は、水素もしくはメチル基であるａＲ４は、ア
クリル基、メタクリル基もしくはシンナモイル基である
。ｎは、０もしくはｌ−２０の整数である。3 "In formula (1), R+ and R3 are hydrogen, methyl group, Ct
or Br, which may be the same or different, R1 is hydrogen or a methyl group, and aR4 is an acrylic group, a methacrylic group, or a cinnamoyl group. n is an integer of 0 or 1-20.
本発明は、−数式（２）で示されるエポキシ樹脂を原料
として、アクリル酸、メタクリル酸もしくはケイ皮酸と
反応させることにより、目的とするシリコーン変性ビニ
ルエステル樹脂を得るものである。The present invention uses an epoxy resin represented by formula (2) as a raw material and reacts it with acrylic acid, methacrylic acid, or cinnamic acid to obtain the desired silicone-modified vinyl ester resin.
−数式（２）中、Ｒ１およびＲ２は、水素、メチル基、
ＣＩまたはＢｒであり、相互に同一であっても異なって
もよい。Ｒ３は、水素もしくはメチル基である。ｎは、
０もしくは１−２０の整数である。- In formula (2), R1 and R2 are hydrogen, methyl group,
CI or Br, which may be the same or different. R3 is hydrogen or a methyl group. n is
It is 0 or an integer from 1-20.
一般式（２）のエポキシ樹脂の合成は、種々の方法が考
えられるが、本発明者らによる特願昭６３−２６９３３
６および特願平１−２３７３２に開示されている一連の
方法が実用的である。合成方法の詳細については、上記
特許に記載されている。Although various methods can be considered for the synthesis of the epoxy resin of general formula (2), Japanese Patent Application No. 63-26933 by the present inventors
6 and Japanese Patent Application No. 1-23732 are practical. Details of the synthesis method are described in the above patents.
次に、シリコーン変性エポキシ樹脂を原料として、アク
リル酸、メタクリル酸もしくはケイ皮酸と反応させるこ
とによる、本発明であるシリコーン変性ビニルエステル
樹脂の合成方法について説明する。Next, a method for synthesizing a silicone-modified vinyl ester resin according to the present invention will be described by using a silicone-modified epoxy resin as a raw material and reacting it with acrylic acid, methacrylic acid, or cinnamic acid.
冷却装置と攪拌装置のついた反応容器に、アクリル酸、
メタクリル酸もしくはケイ皮酸の一種又は混合物、式（
２）のシリコーン変性エポキシ樹脂、触媒、そして安定
剤を所定の比率で仕込み、攪拌しながら所定の温度で所
定の時間反応させた。Acrylic acid,
One or a mixture of methacrylic acid or cinnamic acid, formula (
The silicone-modified epoxy resin of 2), catalyst, and stabilizer were added in a predetermined ratio, and reacted at a predetermined temperature for a predetermined time with stirring.
アクリル酸、メタクリル酸もしくはケイ皮酸はエポキシ
基に対して０．１−２０モル等量の比で加える。１モル
等量以下では、エポキシ基の残存したビニルエステル樹
脂となる。触媒は、３級アミン、４級アンモニウム塩、
及びハロゲン化リチウムのようなルイス酸などを用いる
ことができるが、特に限定されるものではない。触媒の
使用量は、反応物の０．０１−１０重量％、好ましくは
ｏ、 ｉ −５重量％である。安定剤は、重合を禁止す
るもので、多価フェノール類、キノン類、銅塩、フェノ
チアジンなどを用いることができるが、特に限定される
ものではない０反応温度は、室温から１５０℃ぐらいま
での範囲がよく、あまり高温にしすぎると、熱重合する
可能性があるので注意が必要である０反応時間は、０．
５− Ｌ Ｏ時間程度が適当である。また、長時間加熱
すると熱重合する可能性があるので注意が必要である。Acrylic acid, methacrylic acid or cinnamic acid is added in a ratio of 0.1 to 20 molar equivalents to epoxy groups. If the amount is less than 1 molar equivalent, the resin will be a vinyl ester resin with residual epoxy groups. The catalyst is a tertiary amine, a quaternary ammonium salt,
Lewis acids such as lithium halides and the like can be used, but are not particularly limited. The amount of catalyst used is 0.01-10% by weight of the reactants, preferably o,i-5% by weight. The stabilizer inhibits polymerization, and polyhydric phenols, quinones, copper salts, phenothiazine, etc. can be used, but the zero reaction temperature is not particularly limited, from room temperature to about 150°C. The reaction time is within a good range, and care must be taken because if the temperature is too high, there is a possibility of thermal polymerization.The reaction time is 0.
Approximately 5-LO time is appropriate. Also, care must be taken as heating for a long time may cause thermal polymerization.
次に反応系を室温まで冷却してから、反応物を溶媒に溶
解し、アルカリ水溶液、蒸留水の順で３回ずつ洗浄する
。その後、溶媒を十分に除去して、目的とする本発明の
シリコーン変性ビニルエステル樹脂を得ることができる
。溶媒は、水や無機塩類を溶解せず、シリコーン変性ビ
ニルエステル樹脂を溶解するものであれば特に限定され
ない、アルカリ水溶液は、特に限定されないが、できれ
ば強アルカリ水溶液はさけたほうがよい。Next, the reaction system is cooled to room temperature, and then the reactants are dissolved in a solvent and washed three times in the order of aqueous alkaline solution and distilled water. Thereafter, the solvent can be sufficiently removed to obtain the desired silicone-modified vinyl ester resin of the present invention. The solvent is not particularly limited as long as it does not dissolve water or inorganic salts but dissolves the silicone-modified vinyl ester resin. Alkaline aqueous solutions are not particularly limited, but strong alkaline aqueous solutions should be avoided if possible.
以下、実施例により本発明を説明する。 The present invention will be explained below with reference to Examples.
実施例１
１００Ｍ１の２ツロフラスコに、式（２）で示されるシ
リコーン変性エポキシ樹脂（Ｒ＋：Ｈ，Ｒｚ：Ｈ，Ｒ，
：Ｈ，ｎ＝０．エポキシ当量２２３）５ｇ。Example 1 A silicone-modified epoxy resin represented by formula (2) (R+:H, Rz:H, R,
:H, n=0. Epoxy equivalent weight 223) 5g.
アクリル酸１６．１ｇ、ベンジルトリエチルアンモニウ
ムクロライド０．２ｇＳ ｔ−ブチルカテコール０．０
１ｇをとり、１００°Ｃで３時間攪拌しながら反応させ
た。Acrylic acid 16.1g, benzyltriethylammonium chloride 0.2gS t-butylcatechol 0.0
1 g was taken and reacted at 100°C for 3 hours with stirring.
反応終了後、室温に戻し、ベンゼンに溶解後、炭酸ナト
リウム水溶液、蒸留水の順に３回ずつ洗浄した。その後
、ベンゼンを十分に除去して、目的とする弐（１）で示
されるシリコーン変性ビニルエステル樹脂（Ｒ＋ ：
Ｈ、Ｒｚ ： Ｈ、Ｒｓ ： Ｈ、Ｒ−ニアクリル基、
ｎζ０）を６．５ｇ得た。After the reaction was completed, the temperature was returned to room temperature, and after dissolving in benzene, the solution was washed three times in the order of sodium carbonate aqueous solution and distilled water. Thereafter, benzene is sufficiently removed to obtain the desired silicone-modified vinyl ester resin (R+:
H, Rz: H, Rs: H, R-niacryl group,
6.5 g of nζ0) was obtained.
目的物の確認は、ＩＲおよび’Ｈ−ＮＭＲでおこなった
。The target product was confirmed by IR and 'H-NMR.
ｔ Ｒ： １７２０ｃｒ’ エステル基の吸収の出現
９１５Ｃ１１−’ エポキシ基の吸収の消失１０５０
ｃｍ＋ −’ シロキサン結合の吸収をｆｌＩ認エポ
キシ当量測定で、エポキシ基は検出されなかった。t R: 1720cr' Appearance of absorption of ester group 915C11-' Disappearance of absorption of epoxy group 1050
cm+-' The absorption of the siloxane bond was measured by flI epoxy equivalent, and no epoxy group was detected.
実施例２
アクリル酸の代りに、メタクリル酸１９．３ ｇを用い
た以外は、実施例１と同じ要領で行い、目的とする式（
１）で示されるシリコーン変性ビニルエステル樹脂（Ｒ
，：Ｈ，Ｒｚ：Ｈ，Ｒ３：Ｈ，Ｒ４：メタクリル基、ｎ
ξＯ）６．８ｇを得た。生成物の確認は、実施例１と同
様に行い、目的物であることをｌｉ！認した。Example 2 The procedure was repeated in the same manner as in Example 1, except that 19.3 g of methacrylic acid was used instead of acrylic acid, and the desired formula (
1) Silicone modified vinyl ester resin (R
, :H, Rz:H, R3:H, R4: methacrylic group, n
ξO) 6.8 g was obtained. The product was confirmed in the same manner as in Example 1, and confirmed to be the desired product. Approved.
実施例３
アクリル酸の代りにケイ皮酸３３．２ ｇを用いた以外
は、実施例１と同じ要領で行い、目的とする式（１）で
示されるシリコーン変性ビニルエステル樹脂（Ｒ＋：Ｈ
，ＲＺ：Ｈ，’Ｒ，：Ｈ，Ｒ４：シンナモイル基、ｎζ
０）を８．２ｇを得た。生成物の確認は、実施例１と同
様に行い、目的物であることを確認した。Example 3 The same procedure as Example 1 was carried out except that 33.2 g of cinnamic acid was used instead of acrylic acid, and the desired silicone-modified vinyl ester resin (R+:H
, RZ:H, 'R, :H, R4: cinnamoyl group, nζ
0) was obtained. The product was confirmed in the same manner as in Example 1, and was confirmed to be the desired product.
〔発明の効果］
本発明で合成したシリコーン変性ビニルエステル樹脂は
、■分子中に、芳香環とシロキサン結合を有する。その
ため、ビスフェノールＡ型ビニルエステル樹脂の性質と
、シロキサン結合を有する化合物特有の性質の両者を兼
ね備えている。硬化物中に、シロキサン結合を多く導入
できるため、ガラスファイバーやシリコンチップ等への
接着性が向上する。従来のビニルエステル樹脂の用途は
もとより、シロキサン結合の特性を生かした、他分野へ
の応用も考えられる。[Effects of the Invention] The silicone-modified vinyl ester resin synthesized in the present invention has an aromatic ring and a siloxane bond in the molecule. Therefore, it has both the properties of a bisphenol A type vinyl ester resin and the properties unique to a compound having a siloxane bond. Since many siloxane bonds can be introduced into the cured product, adhesion to glass fibers, silicon chips, etc. is improved. In addition to the conventional uses of vinyl ester resins, it is also possible to consider applications in other fields by taking advantage of the characteristics of siloxane bonds.
Claims (3)
ル樹脂。 ▲数式、化学式、表等があります▼−−−（１） 式（１）中、Ｒ＿１およびＲ＿２は、水素、メチル基、
ＣｌまたはＢｒであり、相互に同一であっても異なって
もよい。Ｒ＿３は、水素もしくはメチル基である。Ｒ＿
４は、アクリル基、メタクリル基もしくはシンナモイル
基である。ｎは、０もしくは１−２０の整数である。(1) A silicone-modified vinyl ester resin represented by formula (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼---(1) In formula (1), R_1 and R_2 are hydrogen, methyl group,
Cl or Br, which may be the same or different. R_3 is hydrogen or a methyl group. R_
4 is an acrylic group, a methacrylic group, or a cinnamoyl group. n is 0 or an integer of 1-20.
酸とを、エポキシ基に対して前記酸を、１モル当量以上
で反応させることを特徴とする式（１）で示される請求
項１記載のビニルエステル樹脂の製造方法。 ▲数式、化学式、表等があります▼−−−（２）(2) A claim represented by formula (1), characterized in that formula (2) is reacted with acrylic acid, methacrylic acid, or cinnamic acid in an amount of 1 molar equivalent or more of the acid relative to the epoxy group. 1. The method for producing a vinyl ester resin according to 1. ▲There are mathematical formulas, chemical formulas, tables, etc.▼---(2)
酸とを、エポキシ基に対して前記酸を０．１〜１モル当
量で反応させることを特徴とするビニルエステル樹脂の
製造方法。(3) A method for producing a vinyl ester resin, which comprises reacting formula (2) with acrylic acid, methacrylic acid, or cinnamic acid in an amount of 0.1 to 1 molar equivalent of the acid relative to the epoxy group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18372689A JPH0388816A (en) | 1989-07-18 | 1989-07-18 | Silicone-modified vinyl ester resin and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18372689A JPH0388816A (en) | 1989-07-18 | 1989-07-18 | Silicone-modified vinyl ester resin and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0388816A true JPH0388816A (en) | 1991-04-15 |
Family
ID=16140889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18372689A Pending JPH0388816A (en) | 1989-07-18 | 1989-07-18 | Silicone-modified vinyl ester resin and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0388816A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2756288A1 (en) * | 1996-11-28 | 1998-05-29 | Oreal | NOVEL SILICY FILTER DERIVATIVES ON THEIR ESTER PART, PHOTOPROTECTIVE COSMETIC COMPOSITIONS CONTAINING SAME AND USES THEREOF |
-
1989
- 1989-07-18 JP JP18372689A patent/JPH0388816A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2756288A1 (en) * | 1996-11-28 | 1998-05-29 | Oreal | NOVEL SILICY FILTER DERIVATIVES ON THEIR ESTER PART, PHOTOPROTECTIVE COSMETIC COMPOSITIONS CONTAINING SAME AND USES THEREOF |
| EP0845466A1 (en) * | 1996-11-28 | 1998-06-03 | L'oreal | Silicon containing filtering agents and cosmetic sunscreen compositions containing them |
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