JPS63250347A - Novel acrylic acid ester and production thereof - Google Patents
Novel acrylic acid ester and production thereofInfo
- Publication number
- JPS63250347A JPS63250347A JP8532087A JP8532087A JPS63250347A JP S63250347 A JPS63250347 A JP S63250347A JP 8532087 A JP8532087 A JP 8532087A JP 8532087 A JP8532087 A JP 8532087A JP S63250347 A JPS63250347 A JP S63250347A
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- methyl
- methylethyl
- acrylate
- parts
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000005396 acrylic acid ester group Chemical group 0.000 title description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001253 acrylic acids Chemical class 0.000 claims abstract description 4
- -1 acrylic ester Chemical class 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 abstract description 9
- 238000006116 polymerization reaction Methods 0.000 abstract description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 8
- 238000005886 esterification reaction Methods 0.000 abstract description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 6
- SFIQHFBITUEIBP-UHFFFAOYSA-N 5-methyl-2-propan-2-ylhexan-1-ol Chemical compound CC(C)CCC(CO)C(C)C SFIQHFBITUEIBP-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000003085 diluting agent Substances 0.000 abstract description 4
- 239000003377 acid catalyst Substances 0.000 abstract description 3
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 239000012778 molding material Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 6
- BJTMOUSJDICYJK-UHFFFAOYSA-N (5-methyl-2-propan-2-ylhexyl) prop-2-enoate Chemical compound CC(C)CCC(C(C)C)COC(=O)C=C BJTMOUSJDICYJK-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- MVWPVABZQQJTPL-UHFFFAOYSA-N 2,3-diphenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MVWPVABZQQJTPL-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- AODAQIOEZVDQLS-UHFFFAOYSA-N 3,4-ditert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1C(C)(C)C AODAQIOEZVDQLS-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229960003505 mequinol Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、新規なアクリル酸エステルおよびその製造法
に関し、詳しくは、５−メチル−２−（１−メチルエチ
ル）へキシルアクリレートおよびその製造法に関するも
のである。Detailed Description of the Invention (Industrial Application Field) The present invention relates to a novel acrylic acid ester and a method for producing the same, and more particularly, 5-methyl-2-(1-methylethyl)hexyl acrylate and a method for producing the same. It is about law.
アルコール成分に５−メチル−２−（＋−メヂルエチル
）ヘキサン−１−オールを用いたアクリル酸エステルは
いまだに知られていない。Acrylic acid esters using 5-methyl-2-(+-methylethyl)hexan-1-ol as the alcohol component are still unknown.
（従来の技術）
これまでに５反応性希釈剤として種々のアクリル酸エス
テルが提案されている０例えば、２−エチルへキシルア
クリレートが知られている。(Prior Art) Various acrylic esters have been proposed as reactive diluents. For example, 2-ethylhexyl acrylate is known.
（発明が解決しようとする問題点）
しかしながら、２−エチルへキシルアクリレートは、催
涙性さらには刺激性の強い臭気を有しているため取扱い
難いという欠点がある。(Problems to be Solved by the Invention) However, 2-ethylhexyl acrylate has a drawback that it is difficult to handle because it has lachrymatory properties and a strong irritating odor.
（問題点を解決するための手段）
本発明者らが鋭意検討した結果、催涙性および臭気の改
良された新規なアクリル酸エステルを見出し、本発明を
完成するに至った。すなわち本発明は、構造式、
で表わされる新規なアクリル酸エステルおよびその製造
法を提供するものである。(Means for Solving the Problems) As a result of intensive studies, the present inventors discovered a new acrylic ester with improved lachrymatory properties and odor, and completed the present invention. That is, the present invention provides a novel acrylic ester represented by the structural formula: and a method for producing the same.
本発明の化合物は、５−メチル−２−（１−メチルエチ
ル）ヘキサン−Ｉ−オールとアクリル酸類を反応させる
ことにより得ることができる。The compound of the present invention can be obtained by reacting 5-methyl-2-(1-methylethyl)hexane-I-ol with acrylic acids.
アクリル酸類としては、アクリル酸、アクリル酸低級ア
ルキルエステル、アクリル酸ハライド等が挙げられる。Examples of acrylic acids include acrylic acid, acrylic acid lower alkyl esters, acrylic acid halides, and the like.
アクリル酸とのエステル化反応の場合、５−メチル−２
−（］−メチルエチル）ヘキサン−１−オール１モルと
、アクリル酸０．５〜１．５モル、好ましくは１〜１．
３モルとを、重合禁止剤存在下、酸触媒を用い、５０〜
＋５０’Ｃ１好ましくは８０〜＋２０’ｃの温度でエス
テル化反応することにより得られる。In the case of esterification reaction with acrylic acid, 5-methyl-2
1 mol of -(]-methylethyl)hexan-1-ol and 0.5 to 1.5 mol, preferably 1 to 1.5 mol, of acrylic acid.
3 mol, using an acid catalyst in the presence of a polymerization inhibitor, 50 ~
It is obtained by esterification reaction at a temperature of +50'C1, preferably 80 to +20'C.
上記重合禁止剤としては、例えばラジカル重合禁止剤の
ハイドロキノン、ハイドロキノン千ツメチルエーテル、
ベンゾキノン、ジフェニルベンゾキノン、フェノチアジ
ン、ジ−ｔ−ブチルカテコール、銅塩などが挙げられる
０重合禁止剤は、１１独で用いてもよいし、また、２種
以上を併用してもかまわない、前記重合禁止剤は、理論
エステル生成１ｎｌｏｏ重量部に対し、０．０１〜３重
量部の割合で用いられる。Examples of the polymerization inhibitor include radical polymerization inhibitors such as hydroquinone, hydroquinone methyl ether,
The polymerization inhibitors, which include benzoquinone, diphenylbenzoquinone, phenothiazine, di-t-butylcatechol, copper salt, etc., may be used alone or in combination of two or more. The inhibitor is used in a proportion of 0.01 to 3 parts by weight per 1 nloo parts by weight of theoretical ester production.
また、酸触媒としては、硫酸、パラトルエンスルホン酸
、燐酸のような酸が挙げられる。Further, examples of the acid catalyst include acids such as sulfuric acid, para-toluenesulfonic acid, and phosphoric acid.
１″ｒｌｌ Ｅエステル化反応はベンゼン、トルエン、
キシレン、ｎ−ヘキサン、シクロヘキサン等の溶媒中で
行なうこともできる。1″rll E esterification reaction uses benzene, toluene,
It can also be carried out in a solvent such as xylene, n-hexane, or cyclohexane.
反応は４時間から８時間で終了し、室温まで冷却後、ア
ルカリ水溶液で中和し、さらに塩水で洗浄後、水層を分
離除去し、溶媒を減圧上除去して５−メチル−２−（ｌ
−メチルエチル）へキシルアクリレートを得る。また、
このようにして得られた５−メチル−２−（１−メチル
エチル）へキシルアクリレートを蒸留によって植刃する
ことができる。The reaction was completed in 4 to 8 hours, and after cooling to room temperature, it was neutralized with an alkaline aqueous solution, washed with brine, the aqueous layer was separated and removed, and the solvent was removed under reduced pressure to give 5-methyl-2-( l
-methylethyl)hexyl acrylate is obtained. Also,
The 5-methyl-2-(1-methylethyl)hexyl acrylate thus obtained can be implanted by distillation.
アクリル酸低級アルキルエステルとエステル交換反応を
行う場合には、５−メチル−２−（＋−メチルエチル）
ヘキサン−１−オール１モルに対してアクリル酸の低級
アルキルエステル１〜５モル、重合禁止剤、触媒を仕込
み、沸騰下で反応により生成するアルコールを留去しな
がら行うことができる。When performing a transesterification reaction with acrylic acid lower alkyl ester, 5-methyl-2-(+-methylethyl)
The reaction can be carried out by adding 1 to 5 moles of a lower alkyl ester of acrylic acid, a polymerization inhibitor, and a catalyst to 1 mole of hexan-1-ol, and distilling off the alcohol produced by the reaction at boiling.
エステル交換反応に用いられるアクリル酸低級アルキル
エステルとしては、アクリル酸メチル、アクリル酸エチ
ル、アクリル酸プロピル、アクリル酸ブチルなどが挙げ
られる。Examples of lower alkyl acrylates used in the transesterification reaction include methyl acrylate, ethyl acrylate, propyl acrylate, and butyl acrylate.
上記重合禁止剤は、エステル化反応と同様のものを同ｊ
１程度加えれば良い。The above polymerization inhibitor is the same as that used in the esterification reaction.
Just add about 1.
また、触媒としては、通常のエステル交換反応に使用す
る酸、アルカリならいずれても使用できる。Further, as the catalyst, any acid or alkali used in ordinary transesterification reactions can be used.
生成物を取り出す方法については、エステル化反応と同
様の処理で得ることができる。The product can be obtained by the same treatment as the esterification reaction.
また、アクリル酸ハライドを用いたエステル化反応を行
う場合には、５−メチル−２−（１−メチルエチル）ヘ
キサン−１−オール１モルに対し、アクリル酸ハライド
１〜２モル、重合禁止剤、溶媒、脱ハロゲン化水素剤を
仕込み、０〜８０℃で反応させれば良い。In addition, when performing an esterification reaction using acrylic acid halide, 1 to 2 mol of acrylic acid halide and a polymerization inhibitor per 1 mol of 5-methyl-2-(1-methylethyl)hexan-1-ol. , a solvent, and a dehydrohalogenating agent may be added, and the reaction may be carried out at 0 to 80°C.
溶媒としては、テトラヒドロフラン、ｎ−ヘキサン簿が
挙げられる。Examples of the solvent include tetrahydrofuran and n-hexane.
また、脱ハロゲン化水素剤としては、ピリジン、トリエ
チルアミン等が挙げられる。Further, examples of the dehydrohalogenating agent include pyridine and triethylamine.
本発明における新規なアクリル酸エステルは、常温にお
いて５ ｃｐｓ以下の低粘度の液体で、催涙性がなく臭
気もほとんどなく、また重合速度が速いため、単独ある
いは他の重合性ポリマー、オリ好適に使用される。The novel acrylic acid ester of the present invention is a liquid with a low viscosity of 5 cps or less at room temperature, has no lacrimatory properties, has almost no odor, and has a fast polymerization rate, so it can be used alone or with other polymerizable polymers. be done.
かかる重合性ポリマー、オリゴマー、千ツマー等の具体
例としては下記に示すようなものが挙げられる。Specific examples of such polymerizable polymers, oligomers, polymers, etc. include those shown below.
り２〜８価の多価アルコールおよびポリアルキレングリ
コールのポリ（メタ）アクリレート：例えばジエチレン
グリコール、ネオペンチルグリコール、トリメチロール
プロパン、ペンタエリスリトール、ジペンタエリスリト
ール、トジペンタエリスリトール、ジトリメヂロールブ
ロバンなどのポリ（メタ）アクリレート２）分子中にア
クリロイル基を有するビニル又はジエン共重合体：
例えば末端水酸基をもつポリブタジェンの（メタ）アク
リレート
３）ポリエステル（メタ）アクリレート：例えば無水マ
レイン酸とエチレングリコールとのポリエステルのジ（
メタ）アクリレート、アジピン酸とネオペンチルグリコ
ールとのポリエステルのジ（メタ）アクリレート
４）エポキシポリ（メタ）アクリレート：例えばビスフ
ェノールＡジグリシジルエーテルの（メタ）アクリル酸
付加物
５）ポリウレタンポリ（メタ）アクリレート：例えばペ
ンタエリスリトールトリアクリレートとトリレンジイソ
シアネートとの付加物以下、実施例をもって、本発明を
さらに具体的に説明する。例中、部は全て重量部基準で
ある。Poly(meth)acrylates of di- to octavalent polyhydric alcohols and polyalkylene glycols, such as diethylene glycol, neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol, todipentaerythritol, ditrimedylolbroban, etc. (meth)acrylate 2) Vinyl or diene copolymer having an acryloyl group in the molecule: For example, (meth)acrylate of polybutadiene with a terminal hydroxyl group 3) Polyester (meth)acrylate: For example, a polyester of maleic anhydride and ethylene glycol Ji(
meth)acrylate, di(meth)acrylate of polyester of adipic acid and neopentyl glycol 4) Epoxy poly(meth)acrylate: for example, (meth)acrylic acid adduct of bisphenol A diglycidyl ether 5) Polyurethane poly(meth)acrylate :For example, an adduct of pentaerythritol triacrylate and tolylene diisocyanate.The present invention will be explained in more detail with reference to Examples below. In the examples, all parts are based on parts by weight.
実施例
攪拌装置、還流冷却器付き分留器、温度計、空気導入管
を備えた２１丸型フラスコ内に、アクリル酸１７０部、
５−メチル−２−（＋−メチルエチル）ヘキサン−１−
オール３００部、シクロヘキサン６５０部、硫酸５部、
ハイドロキノン１．２部、硫１％２８１．２部を仕込み
、空気を吹込みながら加熱攪拌し、８０〜９０℃で５時
間反応させ、反応終了後、室温まで冷却し、１０％水酸
化ナトリウム水溶ｉ（１６０ｍ ｌで中和し、さらに１
０％食塩水２５０ｍ１で２回生成物を洗浄した。Example In a 21 round flask equipped with a stirring device, a fractionator with a reflux condenser, a thermometer, and an air introduction tube, 170 parts of acrylic acid,
5-Methyl-2-(+-methylethyl)hexane-1-
300 parts of all, 650 parts of cyclohexane, 5 parts of sulfuric acid,
1.2 parts of hydroquinone and 281.2 parts of 1% sulfur were charged, heated and stirred while blowing air, reacted at 80 to 90°C for 5 hours, and after the reaction was completed, cooled to room temperature and dissolved in 10% sodium hydroxide aqueous solution. i (neutralized with 160 ml, then 1
The product was washed twice with 250 ml of 0% brine.
静置分液した油層に、無水硫酸マグネシウムを３０部加
え、３０分攪拌した後、脱水し、続いてハイドロキノン
４部を加え、減圧下、４０〜５０℃でシクロヘキサンを
除去した。30 parts of anhydrous magnesium sulfate was added to the oil layer separated by standing, and after stirring for 30 minutes, it was dehydrated. Then, 4 parts of hydroquinone was added, and cyclohexane was removed under reduced pressure at 40 to 50°C.
得た生成物４３０部は、低粘度な淡黄色液体の下記構造
式を示す５−メチル−２−（Ｉ−メチルエチル）へキシ
ルアクリレートを主成分（８５％）とするものであった
。430 parts of the obtained product was a low viscosity pale yellow liquid mainly composed of 5-methyl-2-(I-methylethyl)hexyl acrylate having the following structural formula (85%).
この生成物を減圧蒸留して、催涙性がなく且つ臭気のほ
とんどない、沸点９０．５〜９２．３’Ｃ／ ３ ｍ
ｍ ＨＨの無色液体３２５部（収率８０％）を得た。得
た生成物の物性を次に示す。This product is distilled under reduced pressure to produce a product that is non-lachrygenic and has almost no odor, with a boiling point of 90.5-92.3'C/3 m.
325 parts (yield: 80%) of a colorless liquid of mHH were obtained. The physical properties of the obtained product are shown below.
粘度
２．７ｃｐｓ （２５℃）
マススペクトル
［Ｍ”］ ２＋２
赤外線吸収スペクトル）ａｍ−’
＋６３８．１６２０．８１０ （νＣ＝Ｃ）１
７２９ （ｖ Ｃ＝ Ｏ）核磁気共鳴
スペクトル δ（ｐｐｍ）
０．８５〜０．９５． ｄｄ 、 Ｉ ２ Ｈ，Ｃ
Ｈ，−１，１６〜１．８３ 、 ｍ 、 ７Ｈ，−Ｃ
Ｈ＋。Viscosity 2.7 cps (25°C) Mass spectrum [M''] 2+2 Infrared absorption spectrum) am-' +638.1620.810 (νC=C)1
729 (v C=O) nuclear magnetic resonance spectrum δ (ppm) 0.85-0.95. dd, I2H,C
H, -1,16 to 1.83, m, 7H, -C
H+.
−ｃＨ，−
４，１０，ｄ 、 ２１（、’−ＣＨ，−０５，７２
〜６．５２．ｍ 、３Ｈ，ＣＨｍ ＝ＣＨ一応用例
実施例で得た５−メチル−２−（ｌ−メチルエチル）へ
キシルアクリレート１０部、ジペンタエリスリトールへ
キサアクリレート（新中村化学５１）ｔｏ部に、光増感
剤としてイルガキュア１８４（チバガイギー製）１部を
加えた組成物を、ＰＶＣ基村上に塗布し、メタルハライ
ドランプ（アイグラフィックス５３、＋ ２０ Ｗ ／
ｃ ｍ ）を用いて紫外線硬化させた。硬化時間と膜
の密着性を表１に示す。-cH,-4,10,d, 21(,'-CH,-05,72
~6.52. m, 3H, CHm = CH 1 Application Example To 10 parts of 5-methyl-2-(l-methylethyl)hexyl acrylate obtained in Example, to parts of dipentaerythritol hexaacrylate (Shin Nakamura Kagaku 51), A composition containing 1 part of Irgacure 184 (manufactured by Ciba Geigy) as a sensitizer was applied onto a PVC substrate, and a metal halide lamp (Eye Graphics 53, + 20 W/
cm). Table 1 shows the curing time and film adhesion.
表１より本発明のアクリル酸エステルを反応性希釈剤と
して用いた塗膜は塩化ビニル樹脂に対する密着性に優れ
ることが理解される。It is understood from Table 1 that the coating film using the acrylic ester of the present invention as a reactive diluent has excellent adhesion to vinyl chloride resin.
表１
りメタルハライドランプ１０ｃｍ下で？［Ｉが指触乾燥
するまでの時間。Table 1 Under 10cm of metal halide lamp? [Time until I is dry to the touch.
２）セロテープによるゴバン目剥離テストによる。１０
０ケの桝目のうち残った桝目を分子に示す。2) Based on a cross-cut peeling test using Sellotape. 10
The remaining squares among the 0 squares are shown in the numerator.
（発明の効果）
以上説明したように、本発明の化合物は、催涙性がなく
さらに臭気もほとんど無いものであり、また、充分な重
合速度のある反応性希釈剤として用いることができるの
で、塗料、接着剤、成形材料などの分野で有用である。(Effects of the Invention) As explained above, the compound of the present invention has no lacrimatory properties and almost no odor, and can be used as a reactive diluent with a sufficient polymerization rate. It is useful in fields such as adhesives, molding materials, etc.
特許出願人 広栄化学工業株式会社 住友化学工業株式会社Patent applicant: Koei Chemical Industry Co., Ltd. Sumitomo Chemical Co., Ltd.
Claims (1)
１−オールとアクリル酸類とを反応させることを特徴と
する、構造式、 ▲数式、化学式、表等があります▼ で表わされるアクリル酸エステルの製造法。[Claims] 1. An acrylic ester represented by the structural formula ▲ Numerical formula, chemical formula, table, etc. ▼. 2,5-methyl-2-(1-methylethyl)hexane-
A method for producing acrylic esters represented by the structural formula, ▲numerical formula, chemical formula, table, etc.▼, which is characterized by reacting 1-ol with acrylic acids.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8532087A JPS63250347A (en) | 1987-04-07 | 1987-04-07 | Novel acrylic acid ester and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8532087A JPS63250347A (en) | 1987-04-07 | 1987-04-07 | Novel acrylic acid ester and production thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63250347A true JPS63250347A (en) | 1988-10-18 |
Family
ID=13855324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8532087A Pending JPS63250347A (en) | 1987-04-07 | 1987-04-07 | Novel acrylic acid ester and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63250347A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013048735A1 (en) | 2011-09-26 | 2013-04-04 | 3M Innovative Properties Company | Pressure-sensitive adhesives with (meth)acrylic-based elastomeric materials prepared using (2-isopropyl-5-methyl)hexyl (meth)acrylate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5461284A (en) * | 1977-10-25 | 1979-05-17 | Sumitomo Chem Co Ltd | Copolymer emulsion and pressure-sensitive adhesive containing the same |
| JPS59102914A (en) * | 1982-10-12 | 1984-06-14 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Silicone-containing polymer and use |
| JPS60200223A (en) * | 1984-03-24 | 1985-10-09 | Toyo Contact Lens Co Ltd | Oxygen permeable hard contact lens |
-
1987
- 1987-04-07 JP JP8532087A patent/JPS63250347A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5461284A (en) * | 1977-10-25 | 1979-05-17 | Sumitomo Chem Co Ltd | Copolymer emulsion and pressure-sensitive adhesive containing the same |
| JPS59102914A (en) * | 1982-10-12 | 1984-06-14 | チバ−ガイギ−・アクチエンゲゼルシヤフト | Silicone-containing polymer and use |
| JPS60200223A (en) * | 1984-03-24 | 1985-10-09 | Toyo Contact Lens Co Ltd | Oxygen permeable hard contact lens |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013048735A1 (en) | 2011-09-26 | 2013-04-04 | 3M Innovative Properties Company | Pressure-sensitive adhesives with (meth)acrylic-based elastomeric materials prepared using (2-isopropyl-5-methyl)hexyl (meth)acrylate |
| JP2014531497A (en) * | 2011-09-26 | 2014-11-27 | スリーエム イノベイティブ プロパティズ カンパニー | Pressure sensitive adhesive comprising (meth) acrylic elastomer material prepared using (2-isopropyl-5-methyl) hexyl (meth) acrylate |
| US9399724B2 (en) | 2011-09-26 | 2016-07-26 | 3M Innovative Properties Company | Pressure-sensitive adhesives with (meth)acrylic-based elastomeric materials prepared using (2-isopropyl-5-methyl)hexyl (meth)acrylate |
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