RU2012143203A - Способ получения циклического гуанидина из дициандиамида и содержащие его композиции покрытия - Google Patents
Способ получения циклического гуанидина из дициандиамида и содержащие его композиции покрытия Download PDFInfo
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- RU2012143203A RU2012143203A RU2012143203/04A RU2012143203A RU2012143203A RU 2012143203 A RU2012143203 A RU 2012143203A RU 2012143203/04 A RU2012143203/04 A RU 2012143203/04A RU 2012143203 A RU2012143203 A RU 2012143203A RU 2012143203 A RU2012143203 A RU 2012143203A
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- polyamine
- iii
- combinations
- cyanamide
- diglycidyl ether
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title claims abstract 12
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title claims abstract 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title claims abstract 6
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 title claims abstract 4
- 239000008199 coating composition Substances 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract 35
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract 11
- 239000002253 acid Substances 0.000 claims abstract 10
- 229920000768 polyamine Polymers 0.000 claims abstract 10
- 239000004593 Epoxy Substances 0.000 claims abstract 8
- 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 claims abstract 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract 8
- 239000002954 polymerization reaction product Substances 0.000 claims abstract 7
- 150000001412 amines Chemical class 0.000 claims abstract 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract 5
- 238000006243 chemical reaction Methods 0.000 claims abstract 5
- 125000004122 cyclic group Chemical group 0.000 claims abstract 5
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 claims abstract 4
- 229920000647 polyepoxide Polymers 0.000 claims abstract 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract 3
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims abstract 3
- 150000003573 thiols Chemical class 0.000 claims abstract 3
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 claims abstract 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims abstract 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims abstract 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000004615 ingredient Substances 0.000 claims abstract 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims abstract 2
- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000002952 polymeric resin Substances 0.000 claims abstract 2
- 229920003002 synthetic resin Polymers 0.000 claims abstract 2
- 238000006116 polymerization reaction Methods 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 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 abstract 2
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/02—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of guanidine from cyanamide, calcium cyanamide or dicyandiamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/02—Polyamines
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
- C09D5/4419—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications with polymers obtained otherwise than by polymerisation reactions only involving carbon-to-carbon unsaturated bonds
- C09D5/4461—Polyamides; Polyimides
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
- C09D5/4488—Cathodic paints
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- Medicinal Chemistry (AREA)
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- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Resins (AREA)
Abstract
1. Способ получения циклического гуанидина, включающий реакцию (i) цианамида, (ii) полиамина и (iii) слабой кислоты.2. Способ по п.1, в котором (i) цианамид включает дициандиамид.3. Способ по п.1, в котором (ii) полиамин включает дипропилентриамин.4. Способ по п.1, в котором способ дополнительно включает реакцию (iii) слабой кислоты с компонентами (i) и (ii).5. Способ по п.4, в котором (iii) кислота включает фенол, тиол, сульфид, бикарбонат, карбонат, продукты реакции полимеризации любого из вышеупомянутых соединений, или их комбинаций.6. Способ по п.5, в котором фенол включает бисфенол A, бутилфенол, нонилфенол, продукты реакции полимеризации любого из вышеупомянутых соединений или их комбинации.7. Способ по п.1, в котором продукт реакции компонента (i) дополнительно реагирует с эпоксидным соединением.8. Способ получения полимерной смолы, включающий реакцию следующих ингредиентов:(a) циклического гуанидина как продукта реакции: (i) цианамида; (ii) полиамина; и (iii) слабой кислоты;(b) амина; и(c) эпоксидного соединения.9. Способ по п.8, в котором (c) эпоксидное соединение включает оксид пропилена, бутилглицидиловый эфир, фенилглицидиловый эфир, глицидилнеодеканоат или их комбинации.10. Способ по п.8, в котором эпоксидное соединение (c) включает полиэпоксид.11. Способ по п.10, в котором полиэпоксид включает диглицидиловый эфир, продукты реакции полимеризации диглицидиловых эфиров или их комбинации.12. Способ по п.11, в котором диглицидиловый эфир включает диглицидиловый эфир бисфенола A, продукты реакции полимеризации диглицидилового эфира бисфенола A или их комбинации.13. Способ по п.8, в котором амином (ii) является монофункциональный амин.14. Способ по п.8, в которо�
Claims (20)
1. Способ получения циклического гуанидина, включающий реакцию (i) цианамида, (ii) полиамина и (iii) слабой кислоты.
2. Способ по п.1, в котором (i) цианамид включает дициандиамид.
3. Способ по п.1, в котором (ii) полиамин включает дипропилентриамин.
4. Способ по п.1, в котором способ дополнительно включает реакцию (iii) слабой кислоты с компонентами (i) и (ii).
5. Способ по п.4, в котором (iii) кислота включает фенол, тиол, сульфид, бикарбонат, карбонат, продукты реакции полимеризации любого из вышеупомянутых соединений, или их комбинаций.
6. Способ по п.5, в котором фенол включает бисфенол A, бутилфенол, нонилфенол, продукты реакции полимеризации любого из вышеупомянутых соединений или их комбинации.
7. Способ по п.1, в котором продукт реакции компонента (i) дополнительно реагирует с эпоксидным соединением.
8. Способ получения полимерной смолы, включающий реакцию следующих ингредиентов:
(a) циклического гуанидина как продукта реакции: (i) цианамида; (ii) полиамина; и (iii) слабой кислоты;
(b) амина; и
(c) эпоксидного соединения.
9. Способ по п.8, в котором (c) эпоксидное соединение включает оксид пропилена, бутилглицидиловый эфир, фенилглицидиловый эфир, глицидилнеодеканоат или их комбинации.
10. Способ по п.8, в котором эпоксидное соединение (c) включает полиэпоксид.
11. Способ по п.10, в котором полиэпоксид включает диглицидиловый эфир, продукты реакции полимеризации диглицидиловых эфиров или их комбинации.
12. Способ по п.11, в котором диглицидиловый эфир включает диглицидиловый эфир бисфенола A, продукты реакции полимеризации диглицидилового эфира бисфенола A или их комбинации.
13. Способ по п.8, в котором амином (ii) является монофункциональный амин.
14. Способ по п.8, в котором полиамин (ii) включает дипропилентриамин.
15. Способ по п.8, в котором кислота (iii) включает фенол, тиол, сульфид, бикарбонат, карбонат, продукты реакции полимеризации любого из вышеупомянутых соединений или их комбинации.
16. Способ по п.8, в котором способ дополнительно включает реакцию полиамина (d), в котором полиамин может быть тем же самым или отличным от (ii).
17. Способ по п.8, в котором цианамид (i) включает дициандиамид.
18. Способ получения циклического гуанидина, содержащего 6-членное кольцо, в котором способ включает реакцию (i) цианамида; (ii) полиамина; и (iii) слабой кислоты.
19. Композиция покрытия, содержащая продукт реакции по п.1.
20. Композиция покрытия, содержащая продукт реакции по п.18.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/720,971 US8288504B2 (en) | 2010-03-10 | 2010-03-10 | Method of making a cyclic guanidine from dicyandiamide and coating compositions containing same |
| US12/720,971 | 2010-03-10 | ||
| PCT/US2011/027567 WO2011112594A1 (en) | 2010-03-10 | 2011-03-08 | Method of making cyclic guanidine from dicyandiamide and coating compositions containing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012143203A true RU2012143203A (ru) | 2014-04-20 |
| RU2544238C2 RU2544238C2 (ru) | 2015-03-20 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012143203/04A RU2544238C2 (ru) | 2010-03-10 | 2011-03-08 | Способ получения циклического гуанидина из дициандиамида и содержащие его композиции покрытия |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8288504B2 (ru) |
| EP (1) | EP2545031B1 (ru) |
| KR (1) | KR101515273B1 (ru) |
| CN (1) | CN102892751B (ru) |
| CA (1) | CA2792261C (ru) |
| ES (1) | ES2556775T3 (ru) |
| MX (1) | MX2012010437A (ru) |
| RU (1) | RU2544238C2 (ru) |
| WO (1) | WO2011112594A1 (ru) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| NO2515648T3 (ru) | 2009-12-24 | 2018-01-13 | ||
| US8148490B2 (en) | 2010-03-10 | 2012-04-03 | Ppg Industries Ohio, Inc. | Method of making a cyclic guanidine from a guanidinium salt and a weak acid and coating compositions containing the same |
| US9068089B2 (en) | 2013-03-15 | 2015-06-30 | Ppg Industries Ohio, Inc. | Phenolic admix for electrodepositable coating composition containing a cyclic guanidine |
| CN103172639B (zh) * | 2013-03-18 | 2015-08-12 | 惠州市莱佛士制药技术有限公司 | 一种基于盐酸胍的六元二环胍的制备方法 |
| US9688874B2 (en) | 2013-10-25 | 2017-06-27 | Ppg Industries Ohio, Inc. | Method of making a bicyclic guanidine-cured acrylic coating |
| CN106046948A (zh) * | 2016-07-28 | 2016-10-26 | 江苏昌悦重工科技有限公司 | 一种逆变器箱 |
| FI129024B (en) | 2017-11-08 | 2021-05-14 | Helsingin Yliopisto | Process for the preparation of bicyclic guanidine and its derivatives |
| CN112094273A (zh) * | 2020-08-07 | 2020-12-18 | 天津全和诚科技有限责任公司 | 一种的双环胍的合成方法 |
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| US4793867A (en) | 1986-09-26 | 1988-12-27 | Chemfil Corporation | Phosphate coating composition and method of applying a zinc-nickel phosphate coating |
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| US6894086B2 (en) | 2001-12-27 | 2005-05-17 | Ppg Industries Ohio, Inc. | Color effect compositions |
| US7438972B2 (en) | 2004-06-24 | 2008-10-21 | Ppg Industries Ohio, Inc. | Nanoparticle coatings for flexible and/or drawable substrates |
| US7842762B2 (en) * | 2007-08-08 | 2010-11-30 | Ppg Industries Ohio, Inc. | Electrodepositable coating composition containing a cyclic guanidine |
| US8039618B2 (en) * | 2008-05-09 | 2011-10-18 | Ppg Industries Ohio, Inc. | Method for producing bicyclic guanidines by use of a cyclic urea |
| US8334380B2 (en) * | 2008-05-09 | 2012-12-18 | Ppg Industries Ohio, Inc. | Method for producing bicyclic guanidines by use of a cyclic urea and a dehydrating agent |
| US8492542B2 (en) * | 2008-05-15 | 2013-07-23 | Ppg Industries Ohio, Inc. | Method for producing bicyclic guanidines by use of a cyclic thiourea |
| RU2381215C1 (ru) * | 2008-07-31 | 2010-02-10 | Государственное образовательное учреждение высшего профессионального образования "Ивановский государственный химико-технологический университет" (ИГХТУ) | Способ получения 2-имино-4-тиобиурета |
| NO2515648T3 (ru) | 2009-12-24 | 2018-01-13 |
-
2010
- 2010-03-10 US US12/720,971 patent/US8288504B2/en active Active
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- 2011-03-08 KR KR1020127026353A patent/KR101515273B1/ko not_active Expired - Fee Related
- 2011-03-08 RU RU2012143203/04A patent/RU2544238C2/ru active
- 2011-03-08 CN CN201180019234.5A patent/CN102892751B/zh active Active
- 2011-03-08 EP EP11712075.8A patent/EP2545031B1/en active Active
- 2011-03-08 CA CA2792261A patent/CA2792261C/en active Active
- 2011-03-08 ES ES11712075.8T patent/ES2556775T3/es active Active
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Also Published As
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|---|---|
| RU2544238C2 (ru) | 2015-03-20 |
| HK1181032A1 (zh) | 2013-11-01 |
| US20110224403A1 (en) | 2011-09-15 |
| ES2556775T3 (es) | 2016-01-20 |
| KR101515273B1 (ko) | 2015-04-24 |
| US8288504B2 (en) | 2012-10-16 |
| WO2011112594A1 (en) | 2011-09-15 |
| MX2012010437A (es) | 2013-06-18 |
| CN102892751B (zh) | 2016-04-06 |
| KR20120132543A (ko) | 2012-12-05 |
| EP2545031A1 (en) | 2013-01-16 |
| EP2545031B1 (en) | 2015-11-25 |
| CA2792261A1 (en) | 2011-09-15 |
| CN102892751A (zh) | 2013-01-23 |
| CA2792261C (en) | 2015-12-01 |
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