RU2015136630A - POLYSULFIDE POLYOLS, THEIR PRODUCTION AND APPLICATION - Google Patents

POLYSULFIDE POLYOLS, THEIR PRODUCTION AND APPLICATION Download PDF

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Publication number
RU2015136630A
RU2015136630A RU2015136630A RU2015136630A RU2015136630A RU 2015136630 A RU2015136630 A RU 2015136630A RU 2015136630 A RU2015136630 A RU 2015136630A RU 2015136630 A RU2015136630 A RU 2015136630A RU 2015136630 A RU2015136630 A RU 2015136630A
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RU
Russia
Prior art keywords
reaction
sulfur
unsaturated alcohol
mol
alcohol
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RU2015136630A
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Russian (ru)
Inventor
БЛОК Марко БАЛЬБО
Кевин РУДИ
Кристоф ФЛЕККЕНШТАЙН
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Басф Се
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Publication of RU2015136630A publication Critical patent/RU2015136630A/en

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    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
    • C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3863—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms
    • C08G18/3865—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3863—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms
    • C08G18/3865—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms
    • C08G18/3868—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms the sulfur atom belonging to a sulfide group
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/69—Polymers of conjugated dienes
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0025—Foam properties rigid
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/0058—≥50 and <150kg/m3

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyurethanes Or Polyureas (AREA)

Claims (14)

1. Способ получения серосодержащих полиолов реакцией по меньшей мере одного ненасыщенного спирта А с элементарной серой, где ненасыщенный спирт А имеет только один ненасыщенный фрагмент на молекулу в виде двойной углерод-углеродной связи.1. A method for producing sulfur-containing polyols by reacting at least one unsaturated alcohol A with elemental sulfur, where unsaturated alcohol A has only one unsaturated fragment per molecule in the form of a carbon-carbon double bond. 2. Способ по п. 1, где ненасыщенный спирт А имеет 1-4 ОН-групп, предпочтительно 1-2 ОН-групп, особенно предпочтительно одну ОН-группу на молекулу.2. The method according to claim 1, wherein the unsaturated alcohol A has 1-4 OH groups, preferably 1-2 OH groups, particularly preferably one OH group per molecule. 3. Способ по п. 1, где ненасыщенный спирт А имеет молекулярную массу менее 300 г/моль.3. The method of claim 1, wherein the unsaturated alcohol A has a molecular weight of less than 300 g / mol. 4. Способ по п. 1, где по меньшей мере один ненасыщенный спирт А, предпочтительно каждый ненасыщенный спирт А, выбран из группы, состоящей из олеилового спирта, цитронеллола, 10-ундецен-1-ола, линалоола, гераниола, фарнезола, циннамилового спирта.4. The method according to claim 1, where at least one unsaturated alcohol A, preferably each unsaturated alcohol A, is selected from the group consisting of oleyl alcohol, citronellol, 10-undecene-1-ol, linalool, geraniol, farnesol, cinnamyl alcohol . 5. Способ по п. 1, где температура в ходе реакции находится в диапазоне от 100 до 200°С, предпочтительно от 120 до 180°С, особенно предпочтительно от 130° до 160°С.5. The method according to p. 1, where the temperature during the reaction is in the range from 100 to 200 ° C, preferably from 120 to 180 ° C, particularly preferably from 130 ° to 160 ° C. 6. Способ по п. 1, где реакция занимает от 0.5 до 20 часов, предпочтительно от 2 до 18 часов, особенно предпочтительно от 5 до 11 часов.6. The method according to p. 1, where the reaction takes from 0.5 to 20 hours, preferably from 2 to 18 hours, particularly preferably from 5 to 11 hours. 7. Способ по п. 1, где мольное соотношение серы и эквивалентов двойных связей в ненасыщенном спирте А находится в диапазоне от 1 до 9 моль серы на эквивалент двойных связей, предпочтительно от 2 до 6 моль серы на эквивалент двойных связей, особенно предпочтительно от 3 до 5 моль серы на эквивалент двойных связей.7. The method according to claim 1, where the molar ratio of sulfur to equivalents of double bonds in unsaturated alcohol A is in the range from 1 to 9 mol of sulfur per equivalent of double bonds, preferably from 2 to 6 mol of sulfur per equivalent of double bonds, particularly preferably from 3 up to 5 mol of sulfur per equivalent of double bonds. 8. Способ по п. 1, где реакцию проводят в отсутствие растворителя.8. The method according to p. 1, where the reaction is carried out in the absence of a solvent. 9. Способ по п. 1, где реакцию проводят в присутствии по меньшей мере одного растворителя, который предпочтительно имеет температуру кипения по меньшей мере 120°С и предпочтительно не содержит серу.9. The method according to p. 1, where the reaction is carried out in the presence of at least one solvent, which preferably has a boiling point of at least 120 ° C and preferably does not contain sulfur. 10. Способ по п. 1, где в реакционную смесь добавляют по меньшей мере одно аминное соединение, предпочтительно этаноламин.10. The method of claim 1, wherein at least one amine compound, preferably ethanolamine, is added to the reaction mixture. 11. Способ по п. 1, где в реакционную смесь добавляют по меньшей мере одно соединение, выбранное из списка, состоящего из тиазолов, сульфенамидов, гуанидинов, тиурамов, дитиокарбаматов и тиомочевин.11. The method according to p. 1, where at least one compound selected from the list consisting of thiazoles, sulfenamides, guanidines, thiurams, dithiocarbamates and thioureas is added to the reaction mixture. 12. Способ по п. 1, где реакцию проводят в отсутствие аминного соединения.12. The method according to p. 1, where the reaction is carried out in the absence of an amine compound. 13. Способ по любому из пп. 1-12, где реакционную смесь обрабатывают по окончании реакции путем отделения непрореагировавшей серы.13. The method according to any one of paragraphs. 1-12, where the reaction mixture is treated at the end of the reaction by separating unreacted sulfur. 14. Способ по любому из пп. 1-12, где реакционную смесь не обрабатывают по окончании реакции.14. The method according to any one of paragraphs. 1-12, where the reaction mixture is not treated at the end of the reaction.
RU2015136630A 2013-01-29 2014-01-23 POLYSULFIDE POLYOLS, THEIR PRODUCTION AND APPLICATION RU2015136630A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP13153080 2013-01-29
EP13153080.0 2013-01-29
PCT/EP2014/051310 WO2014118073A1 (en) 2013-01-29 2014-01-23 Polysulfide polyols, their production and use in the synthesis of polyurethanes

Publications (1)

Publication Number Publication Date
RU2015136630A true RU2015136630A (en) 2017-03-07

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EP (1) EP2951151A1 (en)
JP (1) JP2016505072A (en)
KR (1) KR20150112013A (en)
CN (1) CN104968645A (en)
BR (1) BR112015018009A2 (en)
RU (1) RU2015136630A (en)
SG (1) SG11201505939YA (en)
WO (1) WO2014118073A1 (en)

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CN107936217A (en) * 2017-11-24 2018-04-20 锦西化工研究院有限公司 A kind of synthetic method of sulfur-containing polymer polyalcohol
GB201814852D0 (en) * 2018-09-12 2018-10-24 Univ Liverpool Sulfur-based Polymers
IT201900011121A1 (en) * 2019-07-08 2021-01-08 Eni Spa PROCEDURE FOR THE PREPARATION OF COPOLYMERS WITH A HIGH SULFUR CONTENT
WO2023214184A1 (en) * 2022-05-06 2023-11-09 The University Of Liverpool Nanoparticles

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DE1545034A1 (en) 1963-09-23 1970-04-09 Thiokol Chemical Corp Process for the production of insulation materials which can be hardened in the air
US4273882A (en) * 1980-06-02 1981-06-16 Olin Corporation Preparation of thermally stable rigid polyurethane foam
ZA862362B (en) * 1985-04-08 1987-11-25 Mobil Oil Corp Sulfurized olefins
DD299187B5 (en) 1990-07-13 1996-05-15 Huels Silicone Gmbh Process for the preparation of sulfur-containing organosilicon compounds
DD299589A7 (en) 1990-07-13 1992-04-30 Nuenchritz Chemie PROCESS FOR PREPARING OLIGO [4- (2-ORGANO-ORGANOOXYSILYL ALKYL) -CYCLOHEXAN-1,2-DIYL] -BIS OLIGOSULFIDES
DE4038589A1 (en) * 1990-12-04 1992-06-11 Bayer Ag RUBBER VULCANISTS WITH GOOD MECHANICAL PROPERTIES AND IMPROVED HYSTERESIS BEHAVIOR
US5338468A (en) * 1992-10-05 1994-08-16 Mobil Oil Corporation Sulfurized olefins
EP0714970A1 (en) * 1994-11-28 1996-06-05 Institut Français du Pétrole Olefinic hydrocarbons sulfurized with elemental sulfur in the presence of alkali on alkaline earth metal hydroxides and glycols, polyglycols or their alkyl ethers and/or water
US6211345B1 (en) 1999-12-22 2001-04-03 Witco Corporation Synthesis of cyclic sulfur silanes
US8138278B2 (en) * 2009-06-29 2012-03-20 Polymeright, Inc. Polymer compositions and methods of making and using same

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WO2014118073A1 (en) 2014-08-07
EP2951151A1 (en) 2015-12-09
BR112015018009A2 (en) 2017-07-11
JP2016505072A (en) 2016-02-18
KR20150112013A (en) 2015-10-06
SG11201505939YA (en) 2015-09-29
CN104968645A (en) 2015-10-07

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