CA2815203C - Flexible, low temperature, filled composite material compositions, coatings, and methods - Google Patents
Flexible, low temperature, filled composite material compositions, coatings, and methods Download PDFInfo
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- CA2815203C CA2815203C CA2815203A CA2815203A CA2815203C CA 2815203 C CA2815203 C CA 2815203C CA 2815203 A CA2815203 A CA 2815203A CA 2815203 A CA2815203 A CA 2815203A CA 2815203 C CA2815203 C CA 2815203C
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- 239000000203 mixture Substances 0.000 title claims abstract description 170
- 239000002131 composite material Substances 0.000 title claims abstract description 136
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000000576 coating method Methods 0.000 title claims description 34
- -1 polysiloxane Polymers 0.000 claims abstract description 217
- 239000000945 filler Substances 0.000 claims abstract description 67
- 150000001412 amines Chemical class 0.000 claims abstract description 61
- 239000007787 solid Substances 0.000 claims abstract description 61
- 239000004970 Chain extender Substances 0.000 claims abstract description 54
- 229920001577 copolymer Polymers 0.000 claims abstract description 52
- 229920001971 elastomer Polymers 0.000 claims abstract description 44
- 239000000806 elastomer Substances 0.000 claims abstract description 44
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 43
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 38
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 16
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 106
- 229920001451 polypropylene glycol Polymers 0.000 claims description 36
- 238000002156 mixing Methods 0.000 claims description 23
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 21
- 239000011248 coating agent Substances 0.000 claims description 21
- 229920000570 polyether Polymers 0.000 claims description 21
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 18
- 229910052751 metal Inorganic materials 0.000 claims description 16
- 239000002184 metal Substances 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 14
- 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 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 239000000919 ceramic Substances 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 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 8
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229920000515 polycarbonate Polymers 0.000 claims description 7
- 239000004417 polycarbonate Substances 0.000 claims description 7
- 239000012255 powdered metal Substances 0.000 claims description 7
- 238000005507 spraying Methods 0.000 claims description 6
- 229910021485 fumed silica Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- 229920003198 poly(di-n-butylsiloxane) Polymers 0.000 claims description 4
- 229920003204 poly(di-n-pentylsiloxane) Polymers 0.000 claims description 4
- 229920003206 poly(di-n-propylsiloxane) Polymers 0.000 claims description 4
- 239000012763 reinforcing filler Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229920000438 poly[methyl(3,3,3-trifluoropropyl)siloxane] polymer Polymers 0.000 claims 2
- 239000000843 powder Substances 0.000 claims 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 89
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 47
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- 239000004814 polyurethane Substances 0.000 description 34
- 229920002635 polyurethane Polymers 0.000 description 34
- 239000000463 material Substances 0.000 description 31
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 21
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000012530 fluid Substances 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 230000008859 change Effects 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000009864 tensile test Methods 0.000 description 9
- 239000000446 fuel Substances 0.000 description 8
- 239000010687 lubricating oil Substances 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 8
- 239000004810 polytetrafluoroethylene Substances 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- 230000003247 decreasing effect Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 239000004809 Teflon Substances 0.000 description 6
- 229920006362 Teflon® Polymers 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229910001111 Fine metal Inorganic materials 0.000 description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229920005749 polyurethane resin Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229910052779 Neodymium Inorganic materials 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- 229910052772 Samarium Inorganic materials 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 235000012501 ammonium carbonate Nutrition 0.000 description 2
- 229910052793 cadmium Inorganic materials 0.000 description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 229910021393 carbon nanotube Inorganic materials 0.000 description 2
- 239000002041 carbon nanotube Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 2
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 239000000571 coke Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- RAQDACVRFCEPDA-UHFFFAOYSA-L ferrous carbonate Chemical compound [Fe+2].[O-]C([O-])=O RAQDACVRFCEPDA-UHFFFAOYSA-L 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical group [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000012256 powdered iron Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- C08G18/28—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
- C08G18/61—Polysiloxanes
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/458—Block-or graft-polymers containing polysiloxane sequences containing polyurethane sequences
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
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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
- C09D175/08—Polyurethanes from polyethers
-
- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Sealing Material Composition (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| US13/492,861 US8748532B2 (en) | 2012-06-09 | 2012-06-09 | Flexible, low temperature, filled composite material compositions, coatings, and methods |
| US13/492,861 | 2012-06-09 |
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| CA2815203A1 CA2815203A1 (en) | 2013-12-09 |
| CA2815203C true CA2815203C (en) | 2016-11-22 |
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| CA2815203A Active CA2815203C (en) | 2012-06-09 | 2013-05-02 | Flexible, low temperature, filled composite material compositions, coatings, and methods |
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| US (1) | US8748532B2 (enExample) |
| EP (1) | EP2671906B1 (enExample) |
| JP (1) | JP6498380B2 (enExample) |
| KR (1) | KR102077343B1 (enExample) |
| CN (1) | CN103483799B (enExample) |
| AU (1) | AU2013203635B2 (enExample) |
| CA (1) | CA2815203C (enExample) |
| RU (1) | RU2636274C2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104177581B (zh) * | 2013-05-27 | 2019-07-30 | 科思创德国股份有限公司 | 用于聚氨酯复合材料的聚氨酯组合物 |
| JP6723155B2 (ja) * | 2014-01-17 | 2020-07-15 | モメンティブ パフォーマンス マテリアルズ インコーポレイテッドＭｏｍｅｎｔｉｖｅ Ｐｅｒｆｏｒｍａｎｃｅ Ｍａｔｅｒｉａｌｓ Ｉｎｃ． | 可撓性の増大した組成物 |
| WO2019118483A1 (en) | 2017-12-11 | 2019-06-20 | Innovative Surface Technologies, Inc. | Polyurea copolymer coating compositions and methods |
| CN109503847B (zh) * | 2018-11-15 | 2021-06-22 | 纳派化学(上海)有限公司 | 一种抗静电硅油的制备方法 |
| CN112491293B (zh) * | 2020-12-03 | 2023-10-20 | 苏州大学 | 一种摩擦纳米发电机的制备方法及摩擦纳米发电机 |
| CN113773794A (zh) * | 2021-08-27 | 2021-12-10 | 金冠电气股份有限公司 | 封装避雷器用高阻隔pbt-聚硅氧烷共聚物基复合材料 |
| CN115368531A (zh) * | 2022-07-09 | 2022-11-22 | 苏州净涵新材料科技有限公司 | 一种自润滑耐污热塑性聚氨酯弹性体及其制备方法 |
| CN116102976B (zh) * | 2022-12-08 | 2024-03-26 | 国网湖北省电力有限公司孝感供电公司 | 一种电缆线路包覆专用防覆冰阻燃绝缘硅涂料 |
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| SU653271A1 (ru) * | 1975-01-06 | 1979-03-25 | Ордена Ленина Институт Элементоорганических Соединений Ан Ссср | Способ получени полиуретансилоксановых эластомеров |
| DE2730744A1 (de) * | 1977-07-07 | 1979-05-03 | Bayer Ag | Mit polyurethan modifizierte organopolysiloxan-massen |
| US4269945A (en) * | 1980-01-24 | 1981-05-26 | The Dow Chemical Company | Reaction injection molded polyurethanes employing aliphatic amine chain extenders |
| JPS6010417A (ja) * | 1983-06-30 | 1985-01-19 | Konishiroku Photo Ind Co Ltd | 磁気記録媒体 |
| JPH0616766A (ja) * | 1992-07-03 | 1994-01-25 | Furukawa Electric Co Ltd:The | 液状重合体組成物 |
| JP2771744B2 (ja) * | 1992-08-24 | 1998-07-02 | 大日精化工業株式会社 | 塗料組成物 |
| JP3404854B2 (ja) * | 1994-02-04 | 2003-05-12 | 横浜ゴム株式会社 | 湿気硬化型ポリウレタン樹脂組成物 |
| US5670598A (en) * | 1995-03-24 | 1997-09-23 | Minnesota Mining And Manufacturing Company | Diblock and triblock polydiorganosiloxane-polyurea block copolymers |
| US5614575A (en) * | 1995-04-24 | 1997-03-25 | Rpg. Inc. | Sprayable polyurethane compositions |
| NZ319016A (en) * | 1995-09-26 | 1998-11-25 | Ameron Int Corp | A polysiloxane polyurethane composition prepared by combining water and an organic di- or polyisocyanate a polyol and a hydroxy containing silicon material |
| AUPO251096A0 (en) * | 1996-09-23 | 1996-10-17 | Cardiac Crc Nominees Pty Limited | Polysiloxane-containing polyurethane elastomeric compositions |
| JP3617349B2 (ja) * | 1998-12-22 | 2005-02-02 | 東海ゴム工業株式会社 | 導電性ロール |
| AUPP991799A0 (en) * | 1999-04-23 | 1999-05-20 | Cardiac Crc Nominees Pty Limited | Siloxane-containing polyurethane-urea compositions |
| DE10024439A1 (de) * | 2000-05-19 | 2001-12-06 | Koppe Franz | Verguss- oder Einbettmasse mit elektromagnetischen Abschirmeigenschaften zur Herstellung elektronischer Bauteile |
| US6451438B1 (en) * | 2000-11-30 | 2002-09-17 | Mearthane Products Corporation | Copolymerization of reactive silicone and urethane precursors for use in conductive, soft urethane rollers |
| JP5052738B2 (ja) * | 2001-10-23 | 2012-10-17 | ダウ・コーニング・コーポレイション | 熱可塑性ポリウレタン−シリコーンエラストマー |
| DE10312063A1 (de) * | 2003-03-18 | 2004-10-07 | Otto Bock Schaumsysteme Gmbh | Polyurethanmasse für die Herstellung von Folien |
| US20080027201A1 (en) * | 2004-06-15 | 2008-01-31 | Iskender Yilgor | Segmented urea and siloxane copolymers and their preparation methods |
| WO2006002045A2 (en) * | 2004-06-15 | 2006-01-05 | Virginia Tech Intellectual Properties, Inc. | Segmented urea and siloxane copolymers and their preparation methods |
| JP4529665B2 (ja) * | 2004-12-07 | 2010-08-25 | 横浜ゴム株式会社 | ウレタン樹脂組成物 |
| US20060276613A1 (en) * | 2005-05-12 | 2006-12-07 | Iskender Yilgor | Polyurethaneurea segmented copolymers |
| AU2007233559C1 (en) * | 2006-03-31 | 2011-11-17 | Aortech International Plc | Biostable polyurethanes |
| JP5087881B2 (ja) * | 2006-08-07 | 2012-12-05 | 横浜ゴム株式会社 | 一液湿気硬化型ウレタン樹脂組成物 |
| WO2009085032A1 (en) * | 2007-12-28 | 2009-07-09 | Honeywell International, Inc | Room temperature vulcanizable polymers |
| DE102008054774A1 (de) * | 2008-12-16 | 2010-06-17 | Wacker Chemie Ag | Siliconhaltiger Polyurethanschaum |
| DE102009028640A1 (de) * | 2009-08-19 | 2011-02-24 | Evonik Goldschmidt Gmbh | Härtbare Masse enthaltend Urethangruppen aufweisende silylierte Polymere und deren Verwendung in Dicht- und Klebstoffen, Binde- und/oder Oberflächenmodifizierungsmitteln |
| US8242189B2 (en) * | 2009-10-13 | 2012-08-14 | Advansource Biomaterials Corporation | Silicone-urethane copolymers |
| CN101798375A (zh) * | 2010-02-09 | 2010-08-11 | 东莞市贝特利新材料有限公司 | 一种改性聚氨酯 |
| US9200160B2 (en) * | 2010-03-29 | 2015-12-01 | Momentive Performance Materials Inc. | Silylated polyurethane/polyorganosiloxane blend and sealant composition and fumed silica composition containing same |
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2012
- 2012-06-09 US US13/492,861 patent/US8748532B2/en active Active
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2013
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- 2013-04-17 KR KR1020130042217A patent/KR102077343B1/ko active Active
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- 2013-06-06 EP EP13170874.5A patent/EP2671906B1/en active Active
- 2013-06-07 JP JP2013120746A patent/JP6498380B2/ja active Active
- 2013-06-07 RU RU2013126215A patent/RU2636274C2/ru active
- 2013-06-08 CN CN201310227605.XA patent/CN103483799B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN103483799B (zh) | 2018-06-22 |
| US20130331509A1 (en) | 2013-12-12 |
| CA2815203A1 (en) | 2013-12-09 |
| JP2014012832A (ja) | 2014-01-23 |
| KR20130138098A (ko) | 2013-12-18 |
| RU2013126215A (ru) | 2014-12-20 |
| US8748532B2 (en) | 2014-06-10 |
| AU2013203635B2 (en) | 2014-10-23 |
| KR102077343B1 (ko) | 2020-02-13 |
| JP6498380B2 (ja) | 2019-04-10 |
| CN103483799A (zh) | 2014-01-01 |
| RU2636274C2 (ru) | 2017-11-22 |
| EP2671906B1 (en) | 2018-08-15 |
| EP2671906A1 (en) | 2013-12-11 |
| AU2013203635A1 (en) | 2014-01-09 |
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