AU2010284136B2 - Hydrolytically stable polyurethane nanocomposites - Google Patents
Hydrolytically stable polyurethane nanocomposites Download PDFInfo
- Publication number
- AU2010284136B2 AU2010284136B2 AU2010284136A AU2010284136A AU2010284136B2 AU 2010284136 B2 AU2010284136 B2 AU 2010284136B2 AU 2010284136 A AU2010284136 A AU 2010284136A AU 2010284136 A AU2010284136 A AU 2010284136A AU 2010284136 B2 AU2010284136 B2 AU 2010284136B2
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- AU
- Australia
- Prior art keywords
- polyester
- polyurethane
- prepolymer
- nanoparticles
- water
- 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.)
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- 229920002635 polyurethane Polymers 0.000 title claims abstract description 173
- 239000004814 polyurethane Substances 0.000 title claims abstract description 173
- 239000002114 nanocomposite Substances 0.000 title claims description 36
- 239000002105 nanoparticle Substances 0.000 claims abstract description 163
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims abstract description 118
- 229920000642 polymer Polymers 0.000 claims abstract description 96
- 229920000728 polyester Polymers 0.000 claims abstract description 94
- 239000002516 radical scavenger Substances 0.000 claims abstract description 69
- 229910000019 calcium carbonate Inorganic materials 0.000 claims abstract description 55
- 239000006185 dispersion Substances 0.000 claims description 108
- 239000002245 particle Substances 0.000 claims description 104
- 150000001875 compounds Chemical class 0.000 claims description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 72
- 229920005862 polyol Polymers 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 39
- 150000003077 polyols Chemical class 0.000 claims description 39
- 150000002148 esters Chemical class 0.000 claims description 35
- 239000004615 ingredient Substances 0.000 claims description 34
- 239000007787 solid Substances 0.000 claims description 26
- 239000010408 film Substances 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 230000002708 enhancing effect Effects 0.000 claims description 19
- 239000005056 polyisocyanate Substances 0.000 claims description 16
- 229920001228 polyisocyanate Polymers 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000011575 calcium Substances 0.000 claims description 9
- 229910052791 calcium Inorganic materials 0.000 claims description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- 239000011777 magnesium Substances 0.000 claims description 7
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 4
- 150000005323 carbonate salts Chemical class 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000004299 exfoliation Methods 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- 239000004416 thermosoftening plastic Substances 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 6
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 claims 2
- 229910000018 strontium carbonate Inorganic materials 0.000 claims 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 1
- 229910052712 strontium Inorganic materials 0.000 claims 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims 1
- LEDMRZGFZIAGGB-UHFFFAOYSA-L strontium carbonate Chemical group [Sr+2].[O-]C([O-])=O LEDMRZGFZIAGGB-UHFFFAOYSA-L 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 22
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 19
- 239000004417 polycarbonate Substances 0.000 abstract description 16
- 229920000515 polycarbonate Polymers 0.000 abstract description 16
- 230000002411 adverse Effects 0.000 abstract description 3
- -1 poly(urethane-urea) Polymers 0.000 description 62
- 239000000203 mixture Substances 0.000 description 58
- 235000010216 calcium carbonate Nutrition 0.000 description 53
- 239000000047 product Substances 0.000 description 33
- 239000002131 composite material Substances 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 24
- 230000007062 hydrolysis Effects 0.000 description 24
- 238000006460 hydrolysis reaction Methods 0.000 description 24
- 238000009826 distribution Methods 0.000 description 23
- 238000012360 testing method Methods 0.000 description 23
- 208000008469 Peptic Ulcer Diseases 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 19
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 18
- 150000002009 diols Chemical class 0.000 description 18
- 238000002156 mixing Methods 0.000 description 18
- 239000004970 Chain extender Substances 0.000 description 17
- 239000012948 isocyanate Substances 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 15
- 150000002513 isocyanates Chemical class 0.000 description 15
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 14
- 238000013459 approach Methods 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 229920005906 polyester polyol Polymers 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- 238000005516 engineering process Methods 0.000 description 12
- 238000000227 grinding Methods 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- 229920003009 polyurethane dispersion Polymers 0.000 description 11
- 239000012736 aqueous medium Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 229920000768 polyamine Polymers 0.000 description 10
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 229940086542 triethylamine Drugs 0.000 description 9
- 239000002981 blocking agent Substances 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 8
- 125000002091 cationic group Chemical group 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 8
- 238000003801 milling Methods 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- 239000002243 precursor Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 241000270295 Serpentes Species 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 238000013019 agitation Methods 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 239000011246 composite particle Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 7
- 150000003335 secondary amines Chemical group 0.000 description 7
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- XRIBIDPMFSLGFS-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(C)CO XRIBIDPMFSLGFS-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 238000012935 Averaging Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 5
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical class CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
- 239000003906 humectant Substances 0.000 description 5
- 230000003472 neutralizing effect Effects 0.000 description 5
- 150000002923 oximes Chemical class 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 5
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 4
- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 description 4
- 229920002799 BoPET Polymers 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 235000019738 Limestone Nutrition 0.000 description 4
- 239000005041 Mylar™ Substances 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001718 carbodiimides Chemical group 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
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- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 3
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- 125000005442 diisocyanate group Chemical group 0.000 description 3
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- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 3
- 150000002429 hydrazines Chemical class 0.000 description 3
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
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- 239000004606 Fillers/Extenders Substances 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
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- 238000005029 sieve analysis Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical group 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NMWCVZCSJHJYFW-UHFFFAOYSA-M sodium;3,5-dichloro-2-hydroxybenzenesulfonate Chemical compound [Na+].OC1=C(Cl)C=C(Cl)C=C1S([O-])(=O)=O NMWCVZCSJHJYFW-UHFFFAOYSA-M 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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- 238000004627 transmission electron microscopy Methods 0.000 description 1
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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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
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
- C08G18/4216—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols
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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
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- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
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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
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- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6644—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
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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
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/005—Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nanotechnology (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Composite Materials (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (3)
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| US23580609P | 2009-08-21 | 2009-08-21 | |
| US61/235,806 | 2009-08-21 | ||
| PCT/US2010/046071 WO2011022582A1 (en) | 2009-08-21 | 2010-08-20 | Hydrolytically stable polyurethane nanocomposites |
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| AU2010284136A1 AU2010284136A1 (en) | 2012-03-08 |
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| US20060205856A1 (en) * | 2004-12-22 | 2006-09-14 | Williamson David T | Compositions of polyesters and sepiolite-type clays |
| US9662869B2 (en) * | 2007-02-08 | 2017-05-30 | Meissner Filtration Products, Inc. | Multilayer film, method of making the same and containers formed from the same |
| UY33917A (es) | 2011-02-23 | 2012-09-28 | Omya Development Ag | ?composiciones para recubrimiento que comprenden submicropartículas que comprenden carbonato de calcio, proceso para prepararlas, y uso de las submicropartículas?. |
| AU2015252038B2 (en) * | 2011-02-23 | 2017-04-20 | Omya International Ag | Coating composition comprising submicron calcium carbonate-comprising particles, process to prepare same and use of submicron calcium carbonate- comprising particles in coating compositions |
| WO2012142816A1 (en) * | 2011-04-18 | 2012-10-26 | Hefei Beini Medical Technology Company, Ltd | Benidipine hydrochloride nanoparticles and preparation method thereof |
| US20140031557A1 (en) * | 2011-04-18 | 2014-01-30 | Hefeibeinie Medical Technology Company, Ltd. | Method for purification of calcium channel blockers of dihydorpyridine type and preparation of nanoparticles thereof |
| DE102011114363A1 (de) * | 2011-09-27 | 2013-03-28 | Kronos International, Inc. | Stabile nanopartikuläre Suspension und Verfahren zur Herstellung |
| EP2912216B1 (en) * | 2012-10-23 | 2016-03-23 | Lubrizol Advanced Materials, Inc. | Dyeable and flame-retarded thermoplastic polyurethane fibers |
| CN103194135B (zh) * | 2013-05-02 | 2015-01-21 | 段宝荣 | 一种耐光性涂料的制备方法 |
| WO2015068174A2 (en) * | 2013-11-11 | 2015-05-14 | Hll Lifecare Limited | Graphene based polymer composites for producing condoms with high heat transfer, improved sensitivity and capacity for drug delivery |
| US10545268B2 (en) * | 2014-05-09 | 2020-01-28 | 3M Innovative Properties Company | Retroreflective articles |
| DE102014212999A1 (de) * | 2014-07-04 | 2016-01-07 | Henkel Ag & Co. Kgaa | Polyurethan-Kaschierklebstoff enthaltend Füllstoffe |
| CN106317369A (zh) * | 2015-06-30 | 2017-01-11 | 宇部兴产株式会社 | 水性聚氨酯树脂分散体及其应用 |
| CN105820791B (zh) * | 2016-02-29 | 2018-12-21 | 洛阳尖端技术研究院 | 石墨烯改性聚氨酯组合物、利用其制备的聚氨酯粘合剂、该粘合剂的制备方法 |
| AU2017229125B2 (en) | 2016-03-08 | 2021-07-29 | Living Proof, Inc. | Long lasting cosmetic compositions |
| PL3287477T3 (pl) | 2016-08-24 | 2020-01-31 | Henkel Ag & Co. Kgaa | Wspomaganie adhezji tworzywa sztucznego w poliuretanowych środkach adhezyjnych 2K |
| CN109963910B (zh) * | 2016-11-09 | 2022-08-19 | 巴斯夫欧洲公司 | 包含石墨烯纳米结构的聚氨酯 |
| JP2020523217A (ja) * | 2017-06-08 | 2020-08-06 | カーボン，インコーポレイテッド | 付加製造において有用な光重合性樹脂のブロッキング基 |
| AU2018333932B2 (en) | 2017-09-13 | 2024-05-02 | Living Proof, Inc. | Long lasting cosmetic compositions |
| EP3681921A2 (en) | 2017-09-13 | 2020-07-22 | Living Proof, Inc. | Color protectant compositions |
| CN111356501A (zh) | 2017-11-20 | 2020-06-30 | 生活实验公司 | 实现持久化妆品性能的属性 |
| BR112020021902B1 (pt) | 2018-04-27 | 2024-02-20 | Living Proof, Inc | Composições cosméticas de poliuretano-ureia para tratamento capilar, método de preservação da ondulação no cabelo humano e os usos de poliuretano-ureia |
| GB201807701D0 (en) * | 2018-05-11 | 2018-06-27 | Ucl Business Plc | (Super)hydrophobic material and coating |
| EP3594281A1 (en) * | 2018-07-13 | 2020-01-15 | ImerTech | Alkaline earth metals for retarding polymer degradation |
| EP3980493A4 (en) | 2019-06-06 | 2023-05-31 | Technion Research & Development Foundation Limited | HYDROLYSIS STABLE SELF-HEALING ELASTOMER |
| CN110903633B (zh) * | 2019-11-28 | 2024-08-23 | 苏州市雄林新材料科技有限公司 | 一种高耐刮tpu薄膜及其制备方法 |
| CN112646535B (zh) * | 2020-12-23 | 2022-07-12 | 广东龙马新材料科技有限公司 | 一种高强度环保木板粘合剂及其制备方法 |
| CN112760023B (zh) * | 2021-01-25 | 2022-04-26 | 四川大学 | 一种混合电荷聚氨酯涂层材料及其制备方法与应用 |
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| WO2006079098A1 (en) * | 2005-01-24 | 2006-07-27 | Lubrizol Advanced Materials, Inc. | Aqueous dispersions of nanoparticle/polyurethane composites |
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| JPS63304051A (ja) * | 1987-06-03 | 1988-12-12 | Furukawa Electric Co Ltd:The | ポリウレタン樹脂組成物 |
| CA2038605C (en) * | 1990-06-15 | 2000-06-27 | Leonard Pinchuk | Crack-resistant polycarbonate urethane polymer prostheses and the like |
| US6576702B2 (en) * | 2000-07-20 | 2003-06-10 | Noveon Ip Holdings Corp. | Plasticized waterborne polyurethane dispersions and manufacturing process |
| US6761969B2 (en) * | 2002-08-21 | 2004-07-13 | Avery Dennison Corporation | Labels and labeling process |
| AU2003297971A1 (en) | 2002-11-21 | 2004-06-18 | The Lubrizol Corporation | Compositions comprising a dispersant and an overbased carboxylate or sulfonate for rheology control in coatings and inks |
| DE102005003299A1 (de) * | 2005-01-24 | 2006-07-27 | Goldschmidt Gmbh | Nanopartikel für die Herstellung von Polyurethanschaum |
| WO2006099630A1 (en) * | 2005-03-17 | 2006-09-21 | Lubrizol Advanced Materials, Inc. | Nanoparticle/vinyl polymer composites |
| FR2891546B1 (fr) * | 2005-10-04 | 2010-09-03 | Solvay | Utilisation de particules de carbonate de calcium dans des compositions polymeriques transparentes, compositions polymeriques transparentes et procede de fabrication de ces compositions |
| US8182920B2 (en) * | 2006-09-21 | 2012-05-22 | Inmat Inc. | Concentrated aqueous nanocomposite dispersions for barrier coatings |
| CN101230232A (zh) * | 2007-01-23 | 2008-07-30 | 张永清 | 环保利废高性能双组分水性聚氨脂防水及装饰涂料 |
| JP4389955B2 (ja) * | 2007-03-30 | 2009-12-24 | Ｔｄｋ株式会社 | 磁気記録媒体及びその製造方法 |
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| AU2010284136A1 (en) | 2012-03-08 |
| JP5554413B2 (ja) | 2014-07-23 |
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