JP2015533859A - 有機修飾モンモリロナイトを含有するポリイソブチレン系ポリウレタン - Google Patents
有機修飾モンモリロナイトを含有するポリイソブチレン系ポリウレタン Download PDFInfo
- Publication number
- JP2015533859A JP2015533859A JP2015524384A JP2015524384A JP2015533859A JP 2015533859 A JP2015533859 A JP 2015533859A JP 2015524384 A JP2015524384 A JP 2015524384A JP 2015524384 A JP2015524384 A JP 2015524384A JP 2015533859 A JP2015533859 A JP 2015533859A
- Authority
- JP
- Japan
- Prior art keywords
- polyurethane
- group
- ammonium salt
- quaternary ammonium
- layered clay
- 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
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- 239000004814 polyurethane Substances 0.000 title claims abstract description 166
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 160
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical class O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 title claims description 45
- 229920002367 Polyisobutene Polymers 0.000 title abstract description 47
- 239000004970 Chain extender Substances 0.000 claims abstract description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 239000004927 clay Substances 0.000 claims description 92
- 125000005442 diisocyanate group Chemical group 0.000 claims description 45
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 44
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 39
- 150000004985 diamines Chemical class 0.000 claims description 37
- 150000002009 diols Chemical class 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 33
- 229920000642 polymer Polymers 0.000 claims description 33
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 25
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- -1 stevensite Inorganic materials 0.000 claims description 15
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 14
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 10
- VNSBYDPZHCQWNB-UHFFFAOYSA-N calcium;aluminum;dioxido(oxo)silane;sodium;hydrate Chemical compound O.[Na].[Al].[Ca+2].[O-][Si]([O-])=O VNSBYDPZHCQWNB-UHFFFAOYSA-N 0.000 claims description 8
- 229910000271 hectorite Inorganic materials 0.000 claims description 8
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 claims description 8
- 229910000273 nontronite Inorganic materials 0.000 claims description 8
- 229910001737 paragonite Inorganic materials 0.000 claims description 8
- 229910000275 saponite Inorganic materials 0.000 claims description 8
- 229910000269 smectite group Inorganic materials 0.000 claims description 8
- 229910052902 vermiculite Inorganic materials 0.000 claims description 8
- 239000010455 vermiculite Substances 0.000 claims description 8
- 235000019354 vermiculite Nutrition 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003863 ammonium salts Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 15
- 229920002396 Polyurea Polymers 0.000 abstract description 12
- 150000001412 amines Chemical class 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 230000001590 oxidative effect Effects 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 4
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000002114 nanocomposite Substances 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000012948 isocyanate Substances 0.000 description 11
- 150000002513 isocyanates Chemical class 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000000523 sample Substances 0.000 description 11
- 239000004202 carbamide Substances 0.000 description 9
- 239000003607 modifier Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 230000015556 catabolic process Effects 0.000 description 8
- 238000006731 degradation reaction Methods 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 238000002441 X-ray diffraction Methods 0.000 description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 7
- 230000003993 interaction Effects 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000002411 thermogravimetry Methods 0.000 description 7
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 238000009830 intercalation Methods 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000032798 delamination Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000002687 intercalation Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003158 alcohol group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 4
- 229910017059 organic montmorillonite Inorganic materials 0.000 description 4
- 229920003226 polyurethane urea Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000010512 thermal transition Effects 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000013016 damping Methods 0.000 description 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 229910003480 inorganic solid Inorganic materials 0.000 description 3
- 238000003780 insertion Methods 0.000 description 3
- 230000037431 insertion Effects 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000002135 nanosheet Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000004299 exfoliation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012802 nanoclay Substances 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 230000036962 time dependent Effects 0.000 description 2
- BYCZEMFWXYCUSJ-UHFFFAOYSA-N 13-hydroxydocosanoic acid Chemical compound CCCCCCCCCC(O)CCCCCCCCCCCC(O)=O BYCZEMFWXYCUSJ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- 101100239079 Arabidopsis thaliana MUR3 gene Proteins 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 101150092391 RSA3 gene Proteins 0.000 description 1
- 229910020175 SiOH Inorganic materials 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical class O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000162 poly(ureaurethane) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006264 polyurethane film Polymers 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000003190 viscoelastic substance Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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Classifications
-
- 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
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
- C08G18/3895—Inorganic compounds, e.g. aqueous alkalimetalsilicate solutions; Organic derivatives thereof containing no direct silicon-carbon bonds
-
- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- 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
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene 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
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
-
- 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
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6204—Polymers of olefins
-
- 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
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C08G18/83—Chemically modified polymers
- C08G18/831—Chemically modified polymers by oxygen-containing compounds inclusive of carbonic acid halogenides, carboxylic acid halogenides and epoxy halides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261674593P | 2012-07-23 | 2012-07-23 | |
| US61/674,593 | 2012-07-23 | ||
| PCT/US2013/051634 WO2014018509A1 (en) | 2012-07-23 | 2013-07-23 | Polyisobutylene-based polyurethanes containing organically modified montmorillonite |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2015533859A true JP2015533859A (ja) | 2015-11-26 |
Family
ID=49997771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015524384A Pending JP2015533859A (ja) | 2012-07-23 | 2013-07-23 | 有機修飾モンモリロナイトを含有するポリイソブチレン系ポリウレタン |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9587069B2 (https=) |
| EP (1) | EP2875071A4 (https=) |
| JP (1) | JP2015533859A (https=) |
| CN (1) | CN104640918A (https=) |
| CA (1) | CA2884247A1 (https=) |
| IN (1) | IN2015DN00393A (https=) |
| WO (1) | WO2014018509A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102570403B1 (ko) * | 2023-02-22 | 2023-08-28 | 순천향대학교 산학협력단 | 나노클레이-폴리우레탄 나노복합체 및 이의 용도 |
Families Citing this family (10)
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|---|---|---|---|---|
| AU2010203373B2 (en) | 2009-01-12 | 2013-08-01 | University Of Massachusetts Lowell | Polyisobutylene-based polyurethanes |
| EP2922888B1 (en) | 2012-11-21 | 2021-08-18 | The University of Massachusetts | High strength polyisobutylene polyurethanes |
| WO2017066520A1 (en) * | 2015-10-17 | 2017-04-20 | Cardiac Pacemakers, Inc. | Production of in situ crosslinkable polyisobutylene-polyurethane nanofibers and coatings |
| WO2017127642A1 (en) * | 2016-01-21 | 2017-07-27 | The University Of Akron | Novel initiators for living carbocationic polymerization |
| EP3592786B1 (en) | 2017-03-07 | 2023-05-10 | Cardiac Pacemakers, Inc. | Hydroboration/oxidation of allyl-terminated polyisobutylene |
| US10835638B2 (en) | 2017-08-17 | 2020-11-17 | Cardiac Pacemakers, Inc. | Photocrosslinked polymers for enhanced durability |
| WO2019143629A1 (en) * | 2018-01-17 | 2019-07-25 | Cardiac Pacemakers, Inc. | End-capped polyisobutylene polyurethane |
| US10899869B2 (en) | 2019-01-24 | 2021-01-26 | The University Of Akron | Glycerol containing polyurethanes and polyurethane nanocomposites |
| CN115028797A (zh) * | 2022-06-24 | 2022-09-09 | 盛鼎高新材料有限公司 | 一种有机硅改性的聚氨酯弹性体及其制备方法 |
| CN115181230B (zh) * | 2022-08-19 | 2023-10-31 | 盛鼎高新材料有限公司 | 一种嵌段共聚聚氨酯弹性体的制备方法 |
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| US5253461A (en) | 1990-12-21 | 1993-10-19 | Tremco, Inc. | Fastener-free roofing system and method |
| CA2457189C (en) | 2001-09-28 | 2011-08-09 | Boston Scientific Limited | Medical devices comprising nanomaterials and therapeutic methods utilizing the same |
| US7125916B2 (en) * | 2003-10-14 | 2006-10-24 | National Chung-Hsing University | Method for producing nanosilica plates |
| US7786189B2 (en) * | 2003-12-22 | 2010-08-31 | Amcol International Corp. | Oligomer-modified layered inorganic compounds and their use in nanocomposites |
| TWI332003B (en) * | 2004-01-30 | 2010-10-21 | Lilly Co Eli | Kinase inhibitors |
| US20070072991A1 (en) * | 2004-06-28 | 2007-03-29 | University Of Akron | Synthesis of thermoplastic polyurethane composites |
| WO2006024068A1 (en) * | 2004-08-30 | 2006-03-09 | The University Of Queensland | Polymer composite |
| WO2007127164A2 (en) * | 2006-04-25 | 2007-11-08 | Medtronic, Inc. | Methods of modifying polyurethanes using surface treated clay |
| WO2009158609A1 (en) * | 2008-06-27 | 2009-12-30 | Cardiac Pacemakers, Inc. | Polyisobutylene urethane, urea and urethane/urea copolymers and medical devices containing the same |
| US20110213084A1 (en) * | 2008-10-01 | 2011-09-01 | The University Of Akron | Polymers having both hard and soft segments, and process for making same |
| US20110152989A1 (en) * | 2009-12-23 | 2011-06-23 | Pacesetter, Inc. | Soft abrasion-resistant polyisobutylene urethane copolymers |
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- 2013-07-23 CA CA2884247A patent/CA2884247A1/en not_active Abandoned
- 2013-07-23 EP EP13823012.3A patent/EP2875071A4/en not_active Withdrawn
- 2013-07-23 WO PCT/US2013/051634 patent/WO2014018509A1/en not_active Ceased
- 2013-07-23 US US14/415,318 patent/US9587069B2/en active Active
- 2013-07-23 CN CN201380048206.5A patent/CN104640918A/zh active Pending
- 2013-07-23 JP JP2015524384A patent/JP2015533859A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102570403B1 (ko) * | 2023-02-22 | 2023-08-28 | 순천향대학교 산학협력단 | 나노클레이-폴리우레탄 나노복합체 및 이의 용도 |
Also Published As
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|---|---|
| CN104640918A (zh) | 2015-05-20 |
| US20150191566A1 (en) | 2015-07-09 |
| CA2884247A1 (en) | 2014-01-30 |
| EP2875071A1 (en) | 2015-05-27 |
| IN2015DN00393A (https=) | 2015-06-19 |
| US9587069B2 (en) | 2017-03-07 |
| WO2014018509A1 (en) | 2014-01-30 |
| EP2875071A4 (en) | 2015-12-23 |
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