SU349693A1 - METHOD OF OBTAINING UNDERTAINED MERCAPTOTHIAZOL ETHERS - Google Patents
METHOD OF OBTAINING UNDERTAINED MERCAPTOTHIAZOL ETHERSInfo
- Publication number
- SU349693A1 SU349693A1 SU1421356A SU1421356A SU349693A1 SU 349693 A1 SU349693 A1 SU 349693A1 SU 1421356 A SU1421356 A SU 1421356A SU 1421356 A SU1421356 A SU 1421356A SU 349693 A1 SU349693 A1 SU 349693A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- undertained
- mercaptothiazol
- ethers
- obtaining
- mercaptobenzthiazole
- Prior art date
Links
- -1 MERCAPTOTHIAZOL ETHERS Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- OCVLSHAVSIYKLI-UHFFFAOYSA-N 3H-1,3-thiazole-2-thione Chemical class SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KRXFTOUYGXMRRU-UHFFFAOYSA-N 3H-1,3-benzothiazole-2-thione;sodium Chemical compound [Na].C1=CC=C2SC(=S)NC2=C1 KRXFTOUYGXMRRU-UHFFFAOYSA-N 0.000 description 1
- SXWJKBPQVPUDID-UHFFFAOYSA-N 4-ethenyl-3H-1,3-benzothiazole-2-thione Chemical compound C=CC1=CC=CC2=C1NC(=S)S2 SXWJKBPQVPUDID-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N Ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N Triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing Effects 0.000 description 1
Description
Изобретение относитс к области получени новых непредельных эфиров меркаптотиазола, способных к реакци м полимеризации и сополимеризации , т. е. соединений, которые могут найти применение в синтезе полимеров или сополимеров с повышенной теплостойкостью.The invention relates to the field of the preparation of new unsaturated mercaptothiazole esters capable of polymerization and copolymerization reactions, i.e. compounds which can be used in the synthesis of polymers or copolymers with enhanced heat resistance.
Известен р д непредельных производных 2-меркаптобензтиазола общей формулыA number of unsaturated 2-mercaptobenzthiazole derivatives of the general formula are known.
где R - пропии-3-ил, бутен-2-ил, аллил и т. д.where R is propium-3-yl, buten-2-yl, allyl, etc.
Однако эти соединени либо имеют симметрично замещенную двойную св зь и поэтому не могут полимеризоватьс в обычных услови х, либо в случае, если R - аллил, эти соединени обладают выраженной способностью к реакции обрыва цепи и не образуют полимеров . Единственное соединение на основе 2-меркаптобензтиазола - винил-2 - меркаптобензтиазол полимеризуетс в основном нод вли нием ионных катализаторов, например триэтилбора.However, these compounds either have a symmetrically substituted double bond and therefore cannot polymerize under normal conditions, or if R is allyl, these compounds have a pronounced ability to break the chain and do not form polymers. The only compound based on 2-mercaptobenzthiazole, vinyl-2-mercaptobenzthiazole, is polymerized mainly by the action of ionic catalysts, for example, triethylboron.
Известен способ получени этилового эфира 2-тиазолмеркаптоуксусной кислоты путем алкилировани натриевой соли 2-меркаптобензтиазола этиловым эфиром хлоруксусной кислоты. Продукты выдел ют известным способом .A method of producing 2-thiazolmercaptoacetic acid ethyl ester is known by alkylation of 2-mercaptobenzthiazole sodium salt with chloroacetic acid ethyl ester. Products are isolated in a known manner.
Предложен основанный на известной реакции алкилированп способ получени непредельных эфиров меркаптотиазола общей формулыA method based on the known alkylation reaction for the preparation of unsaturated mercaptothiazole esters of the general formula
//
./v./v
с with
C7H4f fOCR CH2C7H4f fOCR CH2
где R - водород, метил,where R is hydrogen, methyl,
X - двойна св зь, фенил.X is a double bond, phenyl.
Способ заключаетс том, что щелочнометаллическую соль 2-меркаптотиазола или 2-меркаптобензтиазола подвергают взаимодействию с р-хлорэтиловым эфиром акриловой или метакриловой кислоты. Процесс ведут в среде органического растворител , например в ацетоне или спирте, преимущественно при температуре 70-90°С. Продукты выдел ют известньв способом.The method consists in that the alkali metal salt of 2-mercaptothiazole or 2-mercaptobenzthiazole is reacted with acrylic or methacrylic acid p-chloroethyl ester. The process is conducted in an environment of an organic solvent, for example in acetone or alcohol, preferably at a temperature of 70-90 ° C. Products are isolated by limestone.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU349693A1 true SU349693A1 (en) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7045558B2 (en) | 2003-08-29 | 2006-05-16 | General Electric Company | Method of making a high refractive index optical management coating and the coating |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7045558B2 (en) | 2003-08-29 | 2006-05-16 | General Electric Company | Method of making a high refractive index optical management coating and the coating |
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