CA2884247A1 - Polyisobutylene-based polyurethanes containing organically modified montmorillonite - Google Patents
Polyisobutylene-based polyurethanes containing organically modified montmorillonite Download PDFInfo
- Publication number
- CA2884247A1 CA2884247A1 CA2884247A CA2884247A CA2884247A1 CA 2884247 A1 CA2884247 A1 CA 2884247A1 CA 2884247 A CA2884247 A CA 2884247A CA 2884247 A CA2884247 A CA 2884247A CA 2884247 A1 CA2884247 A1 CA 2884247A1
- Authority
- CA
- Canada
- Prior art keywords
- polyurethane
- group
- alkyl substituents
- layered clay
- quaternary ammonium
- 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.)
- Abandoned
Links
- 239000004814 polyurethane Substances 0.000 title claims abstract description 160
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 154
- 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 39
- 229920002367 Polyisobutene Polymers 0.000 title abstract description 45
- 239000004970 Chain extender Substances 0.000 claims abstract description 45
- 239000004927 clay Substances 0.000 claims description 65
- 125000005442 diisocyanate group Chemical group 0.000 claims description 44
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 41
- 150000004985 diamines Chemical class 0.000 claims description 39
- 150000002009 diols Chemical class 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 34
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 31
- 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 25
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 24
- -1 stevensite Inorganic materials 0.000 claims description 21
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- 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 5
- 229910000271 hectorite Inorganic materials 0.000 claims description 5
- 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 5
- 229910000273 nontronite Inorganic materials 0.000 claims description 5
- 229910001737 paragonite Inorganic materials 0.000 claims description 5
- 229910000275 saponite Inorganic materials 0.000 claims description 5
- 229910052902 vermiculite Inorganic materials 0.000 claims description 5
- 239000010455 vermiculite Substances 0.000 claims description 5
- 235000019354 vermiculite Nutrition 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 4
- 229910021647 smectite Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 abstract description 15
- 229920002396 Polyurea Polymers 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 230000001590 oxidative effect Effects 0.000 abstract description 4
- 150000001412 amines Chemical class 0.000 abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000002114 nanocomposite Substances 0.000 description 42
- 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 16
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000003607 modifier Substances 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000002411 thermogravimetry Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- 230000009102 absorption Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 230000002687 intercalation Effects 0.000 description 4
- 238000009830 intercalation Methods 0.000 description 4
- 229920003226 polyurethane urea Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 3
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229940107816 ammonium iodide Drugs 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000001938 differential scanning calorimetry curve 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
- 238000004299 exfoliation Methods 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 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
- 230000016507 interphase Effects 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002135 nanosheet Substances 0.000 description 3
- 230000036962 time dependent Effects 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000013016 damping Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 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
- 239000000523 sample Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 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
- 230000010512 thermal transition Effects 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- UZUMQQZPGOFJBQ-UHFFFAOYSA-N 1-aminopropane-1,2-diol Chemical compound CC(O)C(N)O UZUMQQZPGOFJBQ-UHFFFAOYSA-N 0.000 description 1
- 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
- 101100239079 Arabidopsis thaliana MUR3 gene Proteins 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
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 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
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 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
- 125000002091 cationic group Chemical group 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
- 101150084411 crn1 gene Proteins 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000032798 delamination 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
- 238000011156 evaluation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000008520 organization Effects 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
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester 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
- 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000269 smectite group Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction 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 class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 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
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 |
|---|---|
| CA2884247A1 true CA2884247A1 (en) | 2014-01-30 |
Family
ID=49997771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2884247A Abandoned CA2884247A1 (en) | 2012-07-23 | 2013-07-23 | Polyisobutylene-based polyurethanes containing organically modified montmorillonite |
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=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| KR102570403B1 (ko) * | 2023-02-22 | 2023-08-28 | 순천향대학교 산학협력단 | 나노클레이-폴리우레탄 나노복합체 및 이의 용도 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2013
- 2013-07-23 IN IN393DEN2015 patent/IN2015DN00393A/en unknown
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| CN104640918A (zh) | 2015-05-20 |
| US20150191566A1 (en) | 2015-07-09 |
| JP2015533859A (ja) | 2015-11-26 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9587069B2 (en) | Polyisobutylene-based polyurethanes containing organically modified montmorillonite | |
| Wang et al. | Preparation, characterization and properties of intrinsic self-healing elastomers | |
| Behera et al. | Self-healable and ultrahydrophobic polyurethane-POSS hybrids by Diels–Alder “click” reaction: a new class of coating material | |
| Jeon et al. | Synthesis and characterizations of waterborne polyurethane–silica hybrids using sol–gel process | |
| Zhang et al. | Synthesis and characterization of eugenol‐based silicone modified waterborne polyurethane with excellent properties | |
| Beniah et al. | Combined effects of carbonate and soft-segment molecular structures on the nanophase separation and properties of segmented polyhydroxyurethane | |
| Gurunathan et al. | Effect of reactive organoclay on physicochemical properties of vegetable oil-based waterborne polyurethane nanocomposites | |
| Sheen et al. | Synthesis and characterization of amorphous octakis-functionalized polyhedral oligomeric silsesquioxanes for polymer nanocomposites | |
| Ren et al. | Triethoxysilane end-functional branched waterborne polyurethane adhesives for leather substrates | |
| Xing et al. | Construction of a flame retardant polyurethane elastomer with degradability, high mechanical strength and shape memory | |
| Saha et al. | Synthesis and characterization of elastomeric polyurethane and PU/clay nanocomposites based on an aliphatic diisocyanate | |
| Kuan et al. | Hydrogen bonding, mechanical properties, and surface morphology of clay/waterborne polyurethane nanocomposites | |
| Usman et al. | Modulating alginate-polyurethane elastomer properties: Influence of NCO/OH ratio with aliphatic diisocyanate | |
| Nugay et al. | Minute amounts of organically modified montmorillonite improve the properties of polyisobutylene‐based polyurethanes | |
| Choi et al. | Nanoclay reinforced UV curable waterborne polyurethane hybrids | |
| Ballard | Supramolecularly Reinforced Films from Polyurethane–Urea Dispersions Containing the Tris-Urea Motif | |
| Subramani et al. | Waterborne trifunctionalsilane‐terminated polyurethane nanocomposite with silane‐modified clay | |
| BR112016004952B1 (pt) | Dispersão tixotrópica, método para fazer a dispersão tixotrópica e composição de resina curável | |
| Wang et al. | A highly stretchable and self-healable hyperbranched polyurethane elastomer with excellent adhesion | |
| Ugarte et al. | Enhancement of thermal and mechanical properties of waterborne polyurethane-urea via chitin nanocrystal reinforcement | |
| Lee et al. | Chemical hybridization of waterborne polyurethane with β-cyclodextrin by sol-gel reaction | |
| Yan et al. | Self-healing waterborne polyurethane nanocomposites with high strength and toughness based on ureidopyrimidinone-modified cellulose nanocrystals | |
| Oguz et al. | Geometric confinement controls stiffness, strength, extensibility, and toughness in poly (urethane–urea) copolymers | |
| US20070072991A1 (en) | Synthesis of thermoplastic polyurethane composites | |
| EP2780320B1 (en) | New process of preparation of polyols and polyamines, and products as obtained |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20190723 |