JPH0776556A - (meth)acrylic monomer - Google Patents
(meth)acrylic monomerInfo
- Publication number
- JPH0776556A JPH0776556A JP5220899A JP22089993A JPH0776556A JP H0776556 A JPH0776556 A JP H0776556A JP 5220899 A JP5220899 A JP 5220899A JP 22089993 A JP22089993 A JP 22089993A JP H0776556 A JPH0776556 A JP H0776556A
- Authority
- JP
- Japan
- Prior art keywords
- meth
- acrylic monomer
- compound
- sulfur
- present
- 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
- 239000000178 monomer Substances 0.000 title claims abstract description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000012990 dithiocarbamate Substances 0.000 claims description 8
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 3
- 125000005399 allylmethacrylate group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 150000004659 dithiocarbamates Chemical class 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 2
- 230000000087 stabilizing effect Effects 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 3
- 150000003464 sulfur compounds Chemical class 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- -1 2-ethylhexyl Chemical group 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004566 building material Substances 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
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 239000003973 paint Substances 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
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は安定化された（メタ）ア
クリル系モノマ−に関する。FIELD OF THE INVENTION This invention relates to stabilized (meth) acrylic monomers.
【０００２】[0002]
【従来の技術】（メタ）アクリル系モノマ−は建築材
料、光ファイバ−、レンズ等の樹脂原料、塗料、繊維、
接着剤等の原料、凝集剤、吸水性ポリマ−、土壌改質剤
原料として単独もしくはスチレン等、他のモノマ−との
共重合体として広く使用されている。これらのモノマ−
用安定剤として、ハイドロキノン類、フェノチアジン、
ヒンダ−ドフェノ−ル類、ヒンダ−ドアミン類、ニトロ
ソアミン類等が知られている。2. Description of the Related Art (Meth) acrylic monomers are used for building materials, optical fibers, resin raw materials for lenses, paints, fibers,
It is widely used as a raw material for adhesives and the like, a flocculant, a water-absorbing polymer, a soil modifier raw material alone or as a copolymer with other monomers such as styrene. These monomers
As stabilizers for hydroquinones, phenothiazine,
Hindered phenols, hindered amines, nitrosamines and the like are known.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、これら
の化合物を用いても充分な熱安定性を得ることはできな
い。本発明者らはこれらの問題点を解決するために検討
を行い、本発明に至った。However, even if these compounds are used, sufficient thermal stability cannot be obtained. The present inventors have conducted investigations to solve these problems and arrived at the present invention.
【０００４】[0004]
【課題を解決するための手段】本発明はこれらの問題点
を解決し、実質的に着色の無い（メタ）アクリル系モノ
マ−の安定化方法を提供することにある。即ち、イオウ
−錫結合を有する化合物またはイオウ化合物と錫化合物
と、ジチオカルバミン酸塩を併用して（メタ）アクリル
系モノマ−用安定剤として使用する事により、これらの
モノマ−を実質的に無着色で安定化することができる。SUMMARY OF THE INVENTION It is an object of the present invention to solve these problems and to provide a method for stabilizing a (meth) acrylic monomer which is substantially free of color. That is, by using a compound having a sulfur-tin bond or a sulfur compound and a tin compound in combination with a dithiocarbamate as a stabilizer for a (meth) acrylic monomer, these monomers are substantially non-colored. Can be stabilized with.
【０００５】即ち、本発明は、「イオウ−錫結合を有す
る化合物とジチオカルバミン酸塩を含有することを特徴
とする（メタ）アクリル系モノマ−」である。That is, the present invention is a "(meth) acrylic monomer containing a compound having a sulfur-tin bond and a dithiocarbamate".
【０００６】本発明の（メタ）アクリル系モノマ−はイ
オウ−錫結合を有する化合物とジチオカルバミン酸塩を
有する化合物を含有することにより無着色で安定性を有
する。 本発明において対象となる（メタ）アクリル系
モノマ−としては（メタ）アクリル酸メチル、（メタ）
アクリル酸エチル、（メタ）アクリル酸ブチル、（メ
タ）アクリル酸２−エチルヘキシル、（メタ）アクリル
酸シクロヘキシル、（メタ）アクリル酸アリル、（メ
タ）アクリル酸２−ヒドロキシエチル、（メタ）アクリ
ル酸シクロヘキセニルメチル、（メタ）アクリル酸メタ
リルなどがある。Since the (meth) acrylic monomer of the present invention contains a compound having a sulfur-tin bond and a compound having a dithiocarbamate, it is non-colored and stable. In the present invention, the target (meth) acrylic monomer is methyl (meth) acrylate, (meth)
Ethyl acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, allyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, cyclo (meth) acrylate Examples include hexenylmethyl and methallyl (meth) acrylate.
【０００７】本発明の（メタ）アクリル系モノマ−に含
有させるイオウ化合物としては、チオグリコ−ル酸、α
−メルカプトプロピオン酸、β−メルカプトプロピオン
酸、及びそれらのエステル、エタンチオ−ル、メタンチ
オ−ル等のチオ−ル類。［（ＣＨ3）2ＮＣ（Ｓ）Ｓ］2
等のモノスルフィド、ポリスルフィド類。フェノチアジ
ン、チアゾ−ル等の含硫複素環式化合物、ＫＳＣ（Ｓ）
Ｎ（ＣＨ3）2等のチオ炭酸誘導体。ジメチルスルホキシ
ド等のスルホキシド類。スルホラン、パラトルエンスル
ホン酸等のスルホン、スルホン酸類及び、イオウ単体等
を使用することができる。The sulfur compound contained in the (meth) acrylic monomer of the present invention includes thioglycolic acid and α
-Mercaptopropionic acid, β-mercaptopropionic acid, and their esters, thiols such as ethanethiol and methanethiol. [(CH 3 ) 2 NC (S) S] 2
Monosulfides, polysulfides, etc. Sulfur-containing heterocyclic compounds such as phenothiazine and thiazole, KSC (S)
Thiocarbonic acid derivatives such as N (CH 3 ) 2 . Sulfoxides such as dimethyl sulfoxide. Sulfolane, sulfone such as paratoluenesulfonic acid, sulfonic acids, and sulfur alone can be used.
【０００８】本発明の（メタ）アクリル系モノマ−に含
有させるジチオカルバミン酸塩としては、ＫＳＣ（Ｓ）
ＮＨ2、Ｚｎ［ＳＣ（Ｓ）Ｎ（Ｃ4Ｈ9）2］2、Ｃｕ[ＳＣ
（Ｓ）Ｎ（ＣＨ3]2）2、Ｆｅ[ＳＣ（Ｓ）Ｎ（ＣＨ3）2]
3、Ｔｅ [ＳＣ（Ｓ）Ｎ（ＣＨ3）2]4等が例示され、置
換ジチオカルバミン酸塩も、無置換ジチオカルバミン酸
塩 も使用できる。The dithiocarbamate salt contained in the (meth) acrylic monomer of the present invention includes KSC (S)
NH 2, Zn [SC (S ) N (C 4 H 9) 2] 2, Cu [SC
(S) N (CH 3] 2) 2, Fe [SC (S) N (CH 3) 2]
3 , Te [SC (S) N (CH 3 ) 2 ] 4 and the like are exemplified, and a substituted dithiocarbamate or an unsubstituted dithiocarbamate can be used.
【０００９】また、ジチオカルバミン酸塩の金属イオン
は特に制限はない。The metal ion of dithiocarbamate is not particularly limited.
【００１０】本発明の（メタ）アクリル系モノマ−に含
有させる錫化合物としては、ＳｎＣｌ2、ＳｎＣｌ4、Ｂ
ｕＳｎ（Ｏ）ＯＨ、Ｂｕ2ＳｎＯ、（Ｍｅ3Ｓｎ）2Ｏ、
Ｂｕ2Ｓｎ（ＯＯＣＣＨ3）2等が例示され、有機錫、無
機錫のいずれも使用することができる。The tin compound contained in the (meth) acrylic monomer of the present invention includes SnCl 2 , SnCl 4 and B.
uSn (O) OH, Bu 2 SnO, (Me 3 Sn) 2 O,
Bu 2 Sn (OOCCH 3 ) 2 and the like are exemplified, and both organic tin and inorganic tin can be used.
【００１１】本発明の（メタ）アクリル系モノマ−に含
有させるイオウ−錫結合を有する化合物としては、その
イオウ−錫結合の形式は共有結合、イオン結合、配位結
合のいずれの形式でも良い。具体的には［Ｂｕ2Ｓｎ
（ＳＣＨ2ＣＯ2）］n、（Ｃ8Ｈ1 7）2Ｓｎ（ＳＣＨ2ＣＯ
2Ｃ8Ｈ17）2、ＣＨ3Ｓｎ（ＳＣＨ2ＣＯ2Ｃ8Ｈ17）3、Ｓ
ｎＳ、ＳｎＳ2等が例示され、このほかにも本発明にお
いて使用されるイオウ化合物と錫化合物を混合して得ら
れる化合物及び錯体等も本発明におけるイオウ−錫結合
を有する化合物である。As the compound having a sulfur-tin bond to be contained in the (meth) acrylic monomer of the present invention, the form of the sulfur-tin bond may be any of covalent bond, ionic bond and coordinate bond. Specifically, [Bu 2 Sn
(SCH 2 CO 2)] n , (C 8 H 1 7) 2 Sn (SCH 2 CO
2 C 8 H 17 ) 2 , CH 3 Sn (SCH 2 CO 2 C 8 H 17 ) 3 , S
Examples thereof include nS and SnS 2. In addition to these, compounds and complexes obtained by mixing the sulfur compound and the tin compound used in the present invention are also compounds having a sulfur-tin bond in the present invention.
【００１２】これらの化合物は単独で使用しても良い
が、これまでに公知である安定剤、例えば、ハイドロキ
ノン、ハイドロキノンモノメチルエ−テル、３，５−ジ
タ−シャリ−ブチル−４−ヒドロキシトルエン等と併用
することもできる。These compounds may be used alone, but they are known stabilizers such as hydroquinone, hydroquinone monomethyl ether, 3,5-di-tert-butyl-4-hydroxytoluene. It can also be used together with.
【００１３】これら安定剤を使用する場合の濃度は１ｐ
ｐｍ〜10000ｐｐｍの範囲、好ましくは10ｐｐｍ〜1000
ｐｐｍの範囲である。When using these stabilizers, the concentration is 1 p
pm to 10,000 ppm range, preferably 10 ppm to 1000
It is in the ppm range.
【００１４】これらイオウ−錫結合を有する化合物とジ
チオカルバミン酸塩を有する化合物を使用する場合の使
用濃度は１〜10000ｐｐｍの範囲、好ましくは10〜1000
ｐｐｍの範囲である。使用濃度が１ｐｐｍ未満では充分
な熱安定性を得ることができず、10000ｐｐｍ以上では
逆に反応性が低下し、かつ、コストアップとなるので共
に好ましくない。When using the compound having a sulfur-tin bond and the compound having a dithiocarbamate, the concentration used is in the range of 1 to 10000 ppm, preferably 10 to 1000.
It is in the ppm range. When the concentration used is less than 1 ppm, sufficient thermal stability cannot be obtained, and when it is 10,000 ppm or more, the reactivity is decreased and the cost is increased.
【００１５】本発明において対象となる（メタ）アクリ
ル系モノマ−は通常、純度95％以上の従来から製品とし
て流通していたグレ−ドのものが対象となる。The (meth) acrylic monomer used in the present invention is usually a graded product having a purity of 95% or more, which has been conventionally distributed as a product.
【００１６】[0016]
【発明の効果】以下、実施例および比較例を用いて本発
明の効果を説明する。The effects of the present invention will be described below with reference to Examples and Comparative Examples.
【００１７】以下の化合物（化合物Ａ、Ｂ、Ｃ）をメタ
クリル酸アリルに添加して１２５℃におけるゲル化開始
時間（ｈｒ）を測定した。なお、使用したメタクリル酸
アリルにはハイドロキノンモノメチルエ−テルが２５０
ｐｐｍ添加されていた。The following compounds (Compounds A, B and C) were added to allyl methacrylate and the gelation onset time (hr) at 125 ° C. was measured. In addition, the allyl methacrylate used was 250 mg of hydroquinone monomethyl ether.
ppm was added.
【００１８】 化合物Ａ：（Ｃ4Ｈ9）2Ｓｎ（ＳＣＨ2ＣＯ2Ｃ8Ｈ17）2 化合物Ｂ：［（Ｃ4Ｈ9）2ＮＣＳ2］2Ｚｎ 化合物Ｃ：［（ＣＨ3）2ＮＣＳ2］2Ｚｎ 実施例１ 化合物Ａ 化合物Ｂ ゲル化開始時間 (ppm) (ppm) (hr) ０ ０ ２．５ ５ ５ ３．０ ２５ ５ ３．０ ５０ ５ ４．５ １００ ５ ４．５ ５ ２５ ３．５ ２５ ２５ ４．５ ５０ ２５ ５．０ １００ ２５ ６．５ ５ ５０ ４．５ ２５ ５０ ５．５ ５０ ５０ ５．５ １００ ５０ ６．５ ５ １００ ４．０ ２５ １００ ５．０ ５０ １００ ５．５ １００ １００ ５．５ 比較例１ Compound A: (C 4 H 9 ) 2 Sn (SCH 2 CO 2 C 8 H 17 ) 2 Compound B: [(C 4 H 9 ) 2 NCS 2 ] 2 Zn Compound C: [(CH 3 ) 2 NCS 2 ] 2 Zn Example 1 Compound A Compound B Gelation start time (ppm) (ppm) (hr) 0 0 2.5 5 5 5 3.0 3.0 25 5 3.0 3.0 50 5 4.5 4.5 100 5 4.5 5 25 3.5 25 25 25 4.5 50 50 25 5.0 100 25 6.5 5.5 50 4.5 25 25 50 5.5 5.5 50 50 5.5 100 50 6.5 5 100 100 4.0 25 100 5.0 50 100 5.5 100 100 5.5 Comparative Example 1
Claims (3)
カルバミン酸塩を含有することを特徴とする（メタ）ア
クリル系モノマ−。1. A (meth) acrylic monomer containing a compound having a sulfur-tin bond and a dithiocarbamate.
ンモノメチルエ−テル等）を含有する請求項１記載の
（メタ）アクリル系モノマ−。2. The (meth) acrylic monomer according to claim 1, which contains a polymerization inhibitor (hydroquinone, hydroquinone monomethyl ether, etc.).
ル酸アリルである請求項１記載の（メタ）アクリル系モ
ノマ−。3. The (meth) acrylic monomer according to claim 1, wherein the (meth) acrylic monomer is allyl methacrylate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5220899A JPH0776556A (en) | 1993-09-06 | 1993-09-06 | (meth)acrylic monomer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5220899A JPH0776556A (en) | 1993-09-06 | 1993-09-06 | (meth)acrylic monomer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0776556A true JPH0776556A (en) | 1995-03-20 |
Family
ID=16758280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5220899A Pending JPH0776556A (en) | 1993-09-06 | 1993-09-06 | (meth)acrylic monomer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0776556A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0845465A3 (en) * | 1996-11-28 | 1999-08-18 | Dow Corning Toray Silicone Company Ltd. | Method for the preparation of acryloxy-functional or methacryloxy-functional organosilicon compounds |
-
1993
- 1993-09-06 JP JP5220899A patent/JPH0776556A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0845465A3 (en) * | 1996-11-28 | 1999-08-18 | Dow Corning Toray Silicone Company Ltd. | Method for the preparation of acryloxy-functional or methacryloxy-functional organosilicon compounds |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20010044555A1 (en) | Thiol and sulfur-containing O-(meth)acrylate counpounds and use thereof | |
| KR940005582A (en) | Substituted phenylimidazolidines, methods for their preparation, uses as medicaments and pharmaceutical compositions containing them | |
| AU536132B2 (en) | Organutin mercaptoalkanol esters and alkoxides containing sulfide groups | |
| ATE13190T1 (en) | PROCESS FOR THE MANUFACTURE OF COATINGS. | |
| DE3571644D1 (en) | Use of peroxycarboxylic acid-containing suspensions as bleaching compositions, novel bleaching compositions and bleaching compositions in the packaged form | |
| DE68923308D1 (en) | Composition and use. | |
| AU777978B2 (en) | Method of preparing a sulfur-containing compound | |
| ATE199152T1 (en) | 1,2,3-THIADIAZOLE CARBOXYLIC ACID (THIO)ESTERS AND THE USE THEREOF AS PESTOPTIC OR MICROBICIDES | |
| JPH0776556A (en) | (meth)acrylic monomer | |
| ATE5877T1 (en) | GRANULATED COMPOSITIONS FOR GLASS MIXTURES, PROCESS FOR THEIR PRODUCTION AND THEIR USE. | |
| JPH0769984A (en) | (meth)acrylic monomer | |
| CN114105939B (en) | Transparent colorless liquid high-refractive-index monomer and application thereof | |
| ATE129491T1 (en) | METHOD FOR PRODUCING ACRYLIC COMPOUNDS CONTAINING SULFUR. | |
| KR890008114A (en) | Fungicides Azolyl- Derivatives | |
| US9187596B2 (en) | Bis-(hydroxyalkyl)mercaptosuccinates | |
| GB2017082A (en) | 5-Fluorouracil derivatives, process for their production and pharmaceuticals containing them | |
| DE59303640D1 (en) | Process for the preparation of thiol (meth) acrylates | |
| JP3223221B2 (en) | Purification method of allyl alcohols | |
| EP0149583A3 (en) | 3-alcoxy-2-(n-pyrrolidino)-n-pyridyl-n-furyl(or thienyl)-methyl propyl amines, their preparation and pharmaceutical compositions containing them | |
| Boduszek et al. | Reaction of thiolate, sulfite, and cyanide ions with cyclic aryl thiolsulfinates: dibenzo [ce]-1, 2-dithiin and naphtho [1, 8-cd]-1, 2-dithiole 1-oxides | |
| IL69066A0 (en) | Thiolphosphoric acid esters,their preparation and pesticidal compositions containing them | |
| KR840000235A (en) | Method for preparing ester of 2-renoyl mercaptopropionylglycine by substituted hydroxybenzenes and pharmaceutical composition containing same | |
| JPS57144230A (en) | Production of aliphatic iodide | |
| DK0491147T3 (en) | Process for the preparation of gold (I) mercaptides | |
| JP2024114237A (en) | Method for purifying aromatic thiol compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A977 | Report on retrieval |
Effective date: 20050308 Free format text: JAPANESE INTERMEDIATE CODE: A971007 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20050518 |
|
| A761 | Written withdrawal of application |
Effective date: 20050719 Free format text: JAPANESE INTERMEDIATE CODE: A761 |