RU2624019C2 - Сополимеризуемые серосодержащие усилители адгезии и композиции, их содержащие - Google Patents
Сополимеризуемые серосодержащие усилители адгезии и композиции, их содержащие Download PDFInfo
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- RU2624019C2 RU2624019C2 RU2015101728A RU2015101728A RU2624019C2 RU 2624019 C2 RU2624019 C2 RU 2624019C2 RU 2015101728 A RU2015101728 A RU 2015101728A RU 2015101728 A RU2015101728 A RU 2015101728A RU 2624019 C2 RU2624019 C2 RU 2624019C2
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- thiol
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- sulfur
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- 239000000203 mixture Substances 0.000 title claims abstract description 160
- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 91
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- 239000011593 sulfur Substances 0.000 claims abstract description 85
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 68
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- 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 27
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229940126062 Compound A Drugs 0.000 claims abstract description 17
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 12
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- 229920006295 polythiol Polymers 0.000 claims description 56
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- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims description 13
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- ZTWTYVWXUKTLCP-UHFFFAOYSA-L ethenyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-L 0.000 claims description 5
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- QEBJRRFIWCWPMA-UHFFFAOYSA-N diethyl-bis(sulfanyl)-$l^{4}-sulfane Chemical group CCS(S)(S)CC QEBJRRFIWCWPMA-UHFFFAOYSA-N 0.000 description 6
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 4
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- 125000003277 amino group Chemical group 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- GDGOJEMDZGZECC-UHFFFAOYSA-N n'-[(3-ethenylphenyl)methyl]-n-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCNCC1=CC=CC(C=C)=C1 GDGOJEMDZGZECC-UHFFFAOYSA-N 0.000 description 3
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
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- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
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- AULUDJRRNHDTJI-UHFFFAOYSA-N 1,1,3,3-tetramethylcyclohexane Chemical compound CC1(C)CCCC(C)(C)C1 AULUDJRRNHDTJI-UHFFFAOYSA-N 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
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- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0209—Polyarylenethioethers derived from monomers containing one aromatic ring
- C08G75/0213—Polyarylenethioethers derived from monomers containing one aromatic ring containing elements other than carbon, hydrogen or sulfur
- C08G75/0218—Polyarylenethioethers derived from monomers containing one aromatic ring containing elements other than carbon, hydrogen or sulfur containing oxygen
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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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0286—Chemical after-treatment
- C08G75/029—Modification with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
- C09J181/02—Polythioethers; Polythioether-ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1031—Sealing waxes, e.g. sealing letters, bottles, or the like
-
- 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
- C08G2190/00—Compositions for sealing or packing joints
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24273—Structurally defined web or sheet [e.g., overall dimension, etc.] including aperture
- Y10T428/24322—Composite web or sheet
- Y10T428/24331—Composite web or sheet including nonapertured component
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Emergency Medicine (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Sealing Material Composition (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
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| RU2796195C1 (ru) * | 2019-10-21 | 2023-05-17 | Феникс Контакт Гмбх Унд Ко. Кг | Носитель информации и способ получения носителя информации |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10047259B2 (en) | 2010-08-13 | 2018-08-14 | Prc-Desoto International, Inc. | Methods for making cured sealants by actinic radiation and related compositions |
| US9303149B2 (en) | 2012-06-21 | 2016-04-05 | Prc-Desoto International, Inc. | Adhesion promoting adducts containing metal ligands, compositions thereof, and uses thereof |
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| US8864930B2 (en) | 2012-07-30 | 2014-10-21 | PRC De Soto International, Inc. | Perfluoroether sealant compositions |
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| HK1222193A1 (zh) * | 2013-10-29 | 2017-06-23 | Prc-迪索托国际公司 | 含金属配体的预聚物、其合成方法和组合物 |
| US9518197B2 (en) | 2014-03-07 | 2016-12-13 | Prc-Desoto International, Inc. | Cure-on-demand moisture-curable urethane-containing fuel resistant prepolymers and compositions thereof |
| US9328275B2 (en) * | 2014-03-07 | 2016-05-03 | Prc Desoto International, Inc. | Phosphine-catalyzed, michael addition-curable sulfur-containing polymer compositions |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2360937C2 (ru) * | 2005-02-08 | 2009-07-10 | Прк-Десото Интернэшнл, Инк. | Отверждаемая композиция, способ ее получения и применения |
| WO2011005614A1 (en) * | 2009-07-09 | 2011-01-13 | Prc-Desoto International, Inc. | One-part moisture curable sealant and method of making the same |
| US20110319559A1 (en) * | 2010-06-25 | 2011-12-29 | PRC-DeSolo International, Inc. | Polythioether polymers, methods for preparation thereof, and compositions comprising them |
| US20120040104A1 (en) * | 2010-08-13 | 2012-02-16 | Prc-Desoto International, Inc. | Methods for making cured sealants by actinic radiation and related compositions |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3454539A (en) * | 1967-08-11 | 1969-07-08 | Ciba Ltd | Polyepoxides |
| US4366307A (en) | 1980-12-04 | 1982-12-28 | Products Research & Chemical Corp. | Liquid polythioethers |
| US4609762A (en) | 1984-01-30 | 1986-09-02 | Products Research & Chemical Corp. | Thioethers having a high sulfur content and method therefor |
| US4623711A (en) | 1985-08-21 | 1986-11-18 | Products Research & Chemical Corp. | Modified disulfide polymer composition and method for making same from mercaptan terminated disulfide polymer and diethyl formal mercaptan terminated polysulfide |
| US5225472A (en) | 1992-05-19 | 1993-07-06 | Courtaulds Aerospace, Inc. | Low viscosity polythiol and method therefor |
| PL334395A1 (en) * | 1997-02-19 | 2000-02-28 | Courtaulds Aerospace | Composition of liquid polythioetheric polymers resisting exposure to fuels and having good flexibility at low temperatures as well as method of obtaining such polymers |
| US5912319A (en) | 1997-02-19 | 1999-06-15 | Courtaulds Aerospace, Inc. | Compositions and method for producing fuel resistant liquid polythioether polymers with good low temperature flexibility |
| US6509418B1 (en) | 1997-02-19 | 2003-01-21 | Prc-Desoto International, Inc. | Sealants and potting formulations including mercapto-terminated polymers produced by the reaction of a polythiol and polyvinyl ether monomer |
| AU2001245600B2 (en) | 2000-03-09 | 2004-10-28 | Advanced Chemistry And Technology, Inc. | Chemically resistant polythioethers and formation thereof |
| US7097883B2 (en) * | 2003-06-05 | 2006-08-29 | Ppg Industries Ohio, Inc. | Low temperature liquid polythioether polymers |
| US20050010003A1 (en) | 2003-07-11 | 2005-01-13 | Prc-Desoto International, Inc. | Epoxy-capped polythioethers |
| US7622548B2 (en) | 2003-07-11 | 2009-11-24 | Prc Desoto International, Inc. | Epoxy- or amine/hydroxy-capped polythioethers |
| US8349951B2 (en) * | 2005-05-31 | 2013-01-08 | Prc Desoto International, Inc. | Polythioether polymers and curable compositions containing them |
| US20070096396A1 (en) | 2005-10-27 | 2007-05-03 | Sawant Suresh G | Dimercaptan terminated polythioether polymers and methods for making and using the same |
| US8816023B2 (en) | 2008-08-13 | 2014-08-26 | Ppg Industries Ohio, Inc | Lightweight particles and compositions containing them |
| US8729198B2 (en) * | 2010-08-13 | 2014-05-20 | Prc Desoto International, Inc. | Compositions comprising thiol-terminated polymers and sulfur-containing ethylenically unsaturated silanes and related cured sealants |
| US9080004B2 (en) * | 2010-10-07 | 2015-07-14 | Prc-Desoto International, Inc. | Diethylene glycol monomethyl ether resistant coating |
| US8513339B1 (en) * | 2012-06-21 | 2013-08-20 | Prc-Desoto International, Inc. | Copolymerizable sulfur-containing adhesion promoters and compositions thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2360937C2 (ru) * | 2005-02-08 | 2009-07-10 | Прк-Десото Интернэшнл, Инк. | Отверждаемая композиция, способ ее получения и применения |
| WO2011005614A1 (en) * | 2009-07-09 | 2011-01-13 | Prc-Desoto International, Inc. | One-part moisture curable sealant and method of making the same |
| US20110319559A1 (en) * | 2010-06-25 | 2011-12-29 | PRC-DeSolo International, Inc. | Polythioether polymers, methods for preparation thereof, and compositions comprising them |
| US20120040104A1 (en) * | 2010-08-13 | 2012-02-16 | Prc-Desoto International, Inc. | Methods for making cured sealants by actinic radiation and related compositions |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2796195C1 (ru) * | 2019-10-21 | 2023-05-17 | Феникс Контакт Гмбх Унд Ко. Кг | Носитель информации и способ получения носителя информации |
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