JP6150889B2 - 水分硬化性ポリシロキサンコーティング組成物 - Google Patents
水分硬化性ポリシロキサンコーティング組成物 Download PDFInfo
- Publication number
- JP6150889B2 JP6150889B2 JP2015520273A JP2015520273A JP6150889B2 JP 6150889 B2 JP6150889 B2 JP 6150889B2 JP 2015520273 A JP2015520273 A JP 2015520273A JP 2015520273 A JP2015520273 A JP 2015520273A JP 6150889 B2 JP6150889 B2 JP 6150889B2
- Authority
- JP
- Japan
- Prior art keywords
- curable composition
- composition
- curable
- combinations
- coating
- 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.)
- Expired - Fee Related
Links
- -1 polysiloxane Polymers 0.000 title claims description 100
- 229920001296 polysiloxane Polymers 0.000 title description 45
- 239000008199 coating composition Substances 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 135
- 238000000576 coating method Methods 0.000 claims description 42
- 239000011248 coating agent Substances 0.000 claims description 32
- 239000000758 substrate Substances 0.000 claims description 28
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 22
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 14
- 150000001409 amidines Chemical class 0.000 claims description 13
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 9
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000005187 foaming Methods 0.000 claims description 3
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 2
- 150000001608 tolans Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 31
- 239000003054 catalyst Substances 0.000 description 30
- 238000001723 curing Methods 0.000 description 23
- 238000002360 preparation method Methods 0.000 description 23
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 19
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 125000004122 cyclic group Chemical group 0.000 description 14
- 125000003709 fluoroalkyl group Chemical group 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- 239000010702 perfluoropolyether Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 10
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 7
- 238000006459 hydrosilylation reaction Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 239000012974 tin catalyst Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000002357 guanidines Chemical class 0.000 description 6
- 238000013008 moisture curing Methods 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- PUNGSQUVTIDKNU-UHFFFAOYSA-N 2,4,6,8,10-pentamethyl-1,3,5,7,9,2$l^{3},4$l^{3},6$l^{3},8$l^{3},10$l^{3}-pentaoxapentasilecane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O[Si](C)O1 PUNGSQUVTIDKNU-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 125000005370 alkoxysilyl group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000007429 general method Methods 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 238000004381 surface treatment Methods 0.000 description 5
- SJBBXFLOLUTGCW-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1 SJBBXFLOLUTGCW-UHFFFAOYSA-N 0.000 description 4
- PDCBZHHORLHNCZ-UHFFFAOYSA-N 1,4-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C=C1 PDCBZHHORLHNCZ-UHFFFAOYSA-N 0.000 description 4
- OPSKRIKFYGJQGJ-UHFFFAOYSA-N 2,4,6,8-tetraethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound CC[Si]1O[Si](CC)O[Si](CC)O[Si](CC)O1 OPSKRIKFYGJQGJ-UHFFFAOYSA-N 0.000 description 4
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- 229940123208 Biguanide Drugs 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229920001774 Perfluoroether Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004404 heteroalkyl group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 229910001092 metal group alloy Inorganic materials 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920006254 polymer film Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000002028 premature Effects 0.000 description 3
- 239000011253 protective coating Substances 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- ZFDWWDZLRKHULH-UHFFFAOYSA-N 1,2-dimethyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C ZFDWWDZLRKHULH-UHFFFAOYSA-N 0.000 description 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YQHJFPFNGVDEDT-UHFFFAOYSA-N 2-tert-butyl-1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(N(C)C)=NC(C)(C)C YQHJFPFNGVDEDT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000004407 fluoroaryl group Chemical group 0.000 description 2
- 125000005348 fluorocycloalkyl group Chemical group 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical group FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 2
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000007725 thermal activation Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- SAPOZTRFWJZUFT-UHFFFAOYSA-N 1,1,1,2,3,4,5,5,5-nonafluoro-4-(trifluoromethyl)pent-2-ene Chemical compound FC(F)(F)C(F)=C(F)C(F)(C(F)(F)F)C(F)(F)F SAPOZTRFWJZUFT-UHFFFAOYSA-N 0.000 description 1
- ISNICOKBNZOJQG-UHFFFAOYSA-N 1,1,2,3,3-pentamethylguanidine Chemical compound CN=C(N(C)C)N(C)C ISNICOKBNZOJQG-UHFFFAOYSA-N 0.000 description 1
- NQOFYFRKWDXGJP-UHFFFAOYSA-N 1,1,2-trimethylguanidine Chemical compound CN=C(N)N(C)C NQOFYFRKWDXGJP-UHFFFAOYSA-N 0.000 description 1
- ZWNSMHHGBQHBRH-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2-propan-2-ylguanidine Chemical compound CC(C)N=C(N(C)C)N(C)C ZWNSMHHGBQHBRH-UHFFFAOYSA-N 0.000 description 1
- ONZXWZBWSBWVTJ-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2-propylguanidine Chemical compound CCCN=C(N(C)C)N(C)C ONZXWZBWSBWVTJ-UHFFFAOYSA-N 0.000 description 1
- PDDWJLGBNYUCQO-UHFFFAOYSA-N 1,1-diethylguanidine Chemical compound CCN(CC)C(N)=N PDDWJLGBNYUCQO-UHFFFAOYSA-N 0.000 description 1
- FTWMCSGJSZWKCR-UHFFFAOYSA-N 1,2,3-tricyclohexylguanidine Chemical compound C1CCCCC1NC(NC1CCCCC1)=NC1CCCCC1 FTWMCSGJSZWKCR-UHFFFAOYSA-N 0.000 description 1
- XKFPXMVATQCVKN-UHFFFAOYSA-N 1,2,3-trimethylguanidine Chemical compound CNC(NC)=NC XKFPXMVATQCVKN-UHFFFAOYSA-N 0.000 description 1
- XKBWVLHEBFSMMG-UHFFFAOYSA-N 1,2-diethyl-5,6-dihydro-4h-pyrimidine Chemical compound CCN1CCCN=C1CC XKBWVLHEBFSMMG-UHFFFAOYSA-N 0.000 description 1
- OQCFWECOQNPQCG-UHFFFAOYSA-N 1,3,4,8-tetrahydropyrimido[4,5-c]oxazin-7-one Chemical compound C1CONC2=C1C=NC(=O)N2 OQCFWECOQNPQCG-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- VXSGBGLNBDTHST-UHFFFAOYSA-N 1-(2-methylpropyl)-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(CC(C)C)CCCN21 VXSGBGLNBDTHST-UHFFFAOYSA-N 0.000 description 1
- IPVTWNBWVXXRLE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2-ethylhexyl)guanidine Chemical compound CCCCC(CC)CNC(=N)NC(N)=N IPVTWNBWVXXRLE-UHFFFAOYSA-N 0.000 description 1
- ZPRFTNGLDOPRSV-UHFFFAOYSA-N 1-(diaminomethylidene)-2-[3-(dibutylamino)propyl]guanidine Chemical compound CCCCN(CCCC)CCCN=C(N)N=C(N)N ZPRFTNGLDOPRSV-UHFFFAOYSA-N 0.000 description 1
- SARCHYUZLAKKFI-UHFFFAOYSA-N 1-(diaminomethylidene)-2-[3-(diethylamino)propyl]guanidine Chemical compound CCN(CC)CCCN=C(N)N=C(N)N SARCHYUZLAKKFI-UHFFFAOYSA-N 0.000 description 1
- JLPWQEHTPOFCPG-UHFFFAOYSA-N 1-(diaminomethylidene)-2-methylguanidine Chemical compound CN=C(N)N=C(N)N JLPWQEHTPOFCPG-UHFFFAOYSA-N 0.000 description 1
- UBJPWXQSHUPNPG-UHFFFAOYSA-N 1-(diaminomethylidene)-2-prop-2-enylguanidine Chemical compound NC(N)=NC(N)=NCC=C UBJPWXQSHUPNPG-UHFFFAOYSA-N 0.000 description 1
- HLLMKZXNMQWDJX-UHFFFAOYSA-N 1-butyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(CCCC)CCCN21 HLLMKZXNMQWDJX-UHFFFAOYSA-N 0.000 description 1
- BYIJEWQQOZJZMN-UHFFFAOYSA-N 1-cyclohexyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCCCC1N1C2=NCCCN2CCC1 BYIJEWQQOZJZMN-UHFFFAOYSA-N 0.000 description 1
- NSCKQAVTPSAALQ-UHFFFAOYSA-N 1-decyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(CCCCCCCCCC)CCCN21 NSCKQAVTPSAALQ-UHFFFAOYSA-N 0.000 description 1
- AAPJUEKLMYSSCH-UHFFFAOYSA-N 1-ethyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(CC)CCCN21 AAPJUEKLMYSSCH-UHFFFAOYSA-N 0.000 description 1
- SCBRJAHMOLUGRP-UHFFFAOYSA-N 1-ethyl-2-methyl-5,6-dihydro-4h-pyrimidine Chemical compound CCN1CCCN=C1C SCBRJAHMOLUGRP-UHFFFAOYSA-N 0.000 description 1
- PCBKFYSULGJBGS-UHFFFAOYSA-N 1-ethyl-2-propan-2-yl-5,6-dihydro-4h-pyrimidine Chemical compound CCN1CCCN=C1C(C)C PCBKFYSULGJBGS-UHFFFAOYSA-N 0.000 description 1
- NTCVBYCDNOJYGK-UHFFFAOYSA-N 1-ethyl-2-propyl-5,6-dihydro-4h-pyrimidine Chemical compound CCCC1=NCCCN1CC NTCVBYCDNOJYGK-UHFFFAOYSA-N 0.000 description 1
- WTEOPULGNUDJAA-UHFFFAOYSA-N 1-ethyl-6-hexyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound CCN1CCCN2C(CCCCCC)CCN=C21 WTEOPULGNUDJAA-UHFFFAOYSA-N 0.000 description 1
- JDOPFDYBTLWCOD-UHFFFAOYSA-N 1-propyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(CCC)CCCN21 JDOPFDYBTLWCOD-UHFFFAOYSA-N 0.000 description 1
- GMIDQSWQUMCQAA-UHFFFAOYSA-N 1-tert-butyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C(C)(C)C)CCCN21 GMIDQSWQUMCQAA-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- SBMYBOVJMOVVQW-UHFFFAOYSA-N 2-[3-[[4-(2,2-difluoroethyl)piperazin-1-yl]methyl]-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound FC(CN1CCN(CC1)CC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CC2=C(CC1)NN=N2)F SBMYBOVJMOVVQW-UHFFFAOYSA-N 0.000 description 1
- ABQPZGFRMFRBBC-UHFFFAOYSA-N 2-butyl-1,1,3,3-tetramethylguanidine Chemical compound CCCCN=C(N(C)C)N(C)C ABQPZGFRMFRBBC-UHFFFAOYSA-N 0.000 description 1
- KREZRKULMRIOKR-UHFFFAOYSA-N 2-butyl-1-(diaminomethylidene)-3-ethylguanidine Chemical compound CCCCN=C(NCC)N=C(N)N KREZRKULMRIOKR-UHFFFAOYSA-N 0.000 description 1
- CGWBIHLHAGNJCX-UHFFFAOYSA-N 2-butylguanidine Chemical compound CCCCNC(N)=N CGWBIHLHAGNJCX-UHFFFAOYSA-N 0.000 description 1
- USGCMNLQYSXCDU-UHFFFAOYSA-N 2-cyclohexyl-1-(diaminomethylidene)guanidine Chemical compound NC(N)=NC(N)=NC1CCCCC1 USGCMNLQYSXCDU-UHFFFAOYSA-N 0.000 description 1
- LJNQGWIMQCKPSH-UHFFFAOYSA-N 2-ethyl-1,1,3,3-tetramethylguanidine Chemical compound CCN=C(N(C)C)N(C)C LJNQGWIMQCKPSH-UHFFFAOYSA-N 0.000 description 1
- YMECANGUBVFOOC-UHFFFAOYSA-N 2-methyl-1-propyl-5,6-dihydro-4h-pyrimidine Chemical compound CCCN1CCCN=C1C YMECANGUBVFOOC-UHFFFAOYSA-N 0.000 description 1
- VSCBATMPTLKTOV-UHFFFAOYSA-N 2-tert-butylimino-n,n-diethyl-1,3-dimethyl-1,3,2$l^{5}-diazaphosphinan-2-amine Chemical compound CCN(CC)P1(=NC(C)(C)C)N(C)CCCN1C VSCBATMPTLKTOV-UHFFFAOYSA-N 0.000 description 1
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 description 1
- RTTNMYWPMMYGIS-UHFFFAOYSA-N 3-(diaminomethylidene)-1,1-diethylguanidine Chemical compound CCN(CC)C(=N)NC(N)=N RTTNMYWPMMYGIS-UHFFFAOYSA-N 0.000 description 1
- DFRWCJYSXGNOFD-UHFFFAOYSA-N 4,6,11-tri(propan-2-yl)-1,4,6,11-tetraza-5-phosphabicyclo[3.3.3]undecane Chemical compound C1CN(C(C)C)P2N(C(C)C)CCN1CCN2C(C)C DFRWCJYSXGNOFD-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KVYPCTQBGFTKIY-UHFFFAOYSA-N CC(CCCCCCCCNNNNN)N Chemical compound CC(CCCCCCCCNNNNN)N KVYPCTQBGFTKIY-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 206010073306 Exposure to radiation Diseases 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 241001546602 Horismenus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- GJWAPAVRQYYSTK-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)amino]-dimethylsilicon Chemical compound C[Si](C)N[Si](C)C GJWAPAVRQYYSTK-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000001994 activation Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001265 acyl fluorides Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000009820 dry lamination Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RCNRJBWHLARWRP-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane;platinum Chemical compound [Pt].C=C[Si](C)(C)O[Si](C)(C)C=C RCNRJBWHLARWRP-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- CELWCAITJAEQNL-UHFFFAOYSA-N oxan-2-ol Chemical class OC1CCCCO1 CELWCAITJAEQNL-UHFFFAOYSA-N 0.000 description 1
- 230000010399 physical interaction Effects 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006294 polydialkylsiloxane Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007430 reference method Methods 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000004447 silicone coating Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- PVNUIRUAPVSSOK-UHFFFAOYSA-N tert-butylimino(tripyrrolidin-1-yl)-$l^{5}-phosphane Chemical compound C1CCCN1P(N1CCCC1)(=NC(C)(C)C)N1CCCC1 PVNUIRUAPVSSOK-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- 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
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
-
- 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
- C08K5/31—Guanidine; Derivatives thereof
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261665146P | 2012-06-27 | 2012-06-27 | |
| US61/665,146 | 2012-06-27 | ||
| PCT/US2013/046072 WO2014025456A2 (en) | 2012-06-27 | 2013-06-17 | Moisture-curable polysiloxane coating composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015527436A JP2015527436A (ja) | 2015-09-17 |
| JP2015527436A5 JP2015527436A5 (OSRAM) | 2016-06-09 |
| JP6150889B2 true JP6150889B2 (ja) | 2017-06-21 |
Family
ID=48699324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015520273A Expired - Fee Related JP6150889B2 (ja) | 2012-06-27 | 2013-06-17 | 水分硬化性ポリシロキサンコーティング組成物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9175188B2 (OSRAM) |
| EP (1) | EP2867316A2 (OSRAM) |
| JP (1) | JP6150889B2 (OSRAM) |
| CN (1) | CN104540909A (OSRAM) |
| WO (1) | WO2014025456A2 (OSRAM) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013101938A1 (en) * | 2011-12-27 | 2013-07-04 | Dow Corning Corporation | Organopolysiloxanes including silicon-bonded trialkylsilyl-substituted organic groups |
| EP2867316A2 (en) | 2012-06-27 | 2015-05-06 | 3M Innovative Properties Company | Moisture-curable polysiloxane coating composition |
| SG11201703320QA (en) | 2014-10-28 | 2017-05-30 | 3M Innovative Properties Co | Spray application system components comprising a repellent surface & methods |
| US10584249B2 (en) | 2015-10-28 | 2020-03-10 | 3M Innovative Properties Company | Articles subject to ice formation comprising a repellent surface |
| CN113145341A (zh) | 2015-10-28 | 2021-07-23 | 3M创新有限公司 | 包括拒液表面的喷雾施用系统部件和方法 |
| US10351729B2 (en) * | 2016-03-03 | 2019-07-16 | Motorola Mobility Llc | Polysiloxane films and methods of making polysiloxane films |
| EP3448944A4 (en) | 2016-04-26 | 2019-11-13 | 3M Innovative Properties Company | ARTISTS SUBJECT TO ICE FORMATION WITH A REPELLENT SURFACE COMPRISING SILOXONE MATERIAL |
| CN109467707B (zh) * | 2017-09-07 | 2022-02-01 | 青岛科技大学 | 线性聚磷腈化合物及其制备方法和用途 |
| US20220010169A1 (en) * | 2018-11-26 | 2022-01-13 | 3M Innovative Properties Company | Curable coating compositions, methods, and articles |
| US11840587B2 (en) | 2019-02-13 | 2023-12-12 | Dow Global Technologies Llc | Moisture-curable polyolefin formulation |
| KR20210126659A (ko) | 2019-02-13 | 2021-10-20 | 다우 글로벌 테크놀로지스 엘엘씨 | 수분 경화성 폴리올레핀 제형 |
| WO2020225717A1 (en) | 2019-05-08 | 2020-11-12 | 3M Innovative Properties Company | Nanostructured article |
| CN113924344B (zh) | 2019-06-04 | 2023-07-14 | 美国陶氏有机硅公司 | 作为用于Si-H和Si-O-Si之间的反应的热触发剂的桥联受阻路易斯对 |
| CN113924330B (zh) | 2019-06-04 | 2023-01-24 | 美国陶氏有机硅公司 | 甲硅烷基氢化物与甲硅烷基醚和/或硅烷醇之间的热引发的酸催化反应 |
| EP3980429B1 (en) | 2019-06-04 | 2023-05-10 | Dow Silicones Corporation | Bridged frustrated lewis pairs as thermal trigger for reactions between si-h and si-or |
| JP7560490B2 (ja) | 2019-06-04 | 2024-10-02 | ダウ シリコーンズ コーポレーション | Ｓｉ－Ｈとエポキシドとの反応のための熱誘発としての架橋型フラストレイテッドルイスペア |
| KR20220016905A (ko) | 2019-06-04 | 2022-02-10 | 다우 실리콘즈 코포레이션 | Si-H와 알파-베타 불포화된 에스테르의 반응을 위한 열 트리거로서의 가교된 불완전 루이스 쌍 |
| KR20220016899A (ko) | 2019-06-04 | 2022-02-10 | 다우 실리콘즈 코포레이션 | 실릴 수소화물과 실록산의 열적으로 개시된 산 촉매화된 반응 |
| EP3980428B1 (en) | 2019-06-04 | 2023-04-26 | Dow Silicones Corporation | Thermally initiated acid catalyzed reaction between silyl hydride and alpha-beta unsaturated esters |
| CN110484129B (zh) | 2019-07-02 | 2022-01-25 | 昆山联滔电子有限公司 | 带有防护涂层的产品及其制备方法 |
| WO2021024118A1 (en) | 2019-08-02 | 2021-02-11 | 3M Innovative Properties Company | Composition including a polyorganosiloxane and an amino-functional silane and method of using the same |
| JP7415466B2 (ja) * | 2019-11-14 | 2024-01-17 | 株式会社レゾナック | 撥水処理剤、撥水構造体、及び撥水構造体の製造方法 |
| US11708494B2 (en) * | 2020-02-14 | 2023-07-25 | Icp Construction, Inc. | Oleophobic and hydrophobic composition |
| WO2021247210A1 (en) | 2020-06-04 | 2021-12-09 | Dow Silicones Corporation | Epoxy-curable silicone release coating composition and methods for its preparation and use |
| WO2022101786A1 (en) | 2020-11-10 | 2022-05-19 | 3M Innovative Properties Company | Process for making a coated article |
| JP7623678B2 (ja) * | 2020-12-15 | 2025-01-29 | 日東化成株式会社 | 重合体の硬化に用いる硬化触媒を含む湿気硬化型組成物、硬化物の製造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3250808A (en) | 1963-10-31 | 1966-05-10 | Du Pont | Fluorocarbon ethers derived from hexafluoropropylene epoxide |
| US4181752A (en) | 1974-09-03 | 1980-01-01 | Minnesota Mining And Manufacturing Company | Acrylic-type pressure sensitive adhesives by means of ultraviolet radiation curing |
| WO1998040439A1 (en) | 1997-03-14 | 1998-09-17 | Minnesota Mining And Manufacturing Company | Cure-on-demand, moisture-curable compositions having reactive silane functionality |
| JP2007161746A (ja) * | 2005-12-09 | 2007-06-28 | Shin Etsu Chem Co Ltd | シリコーンエマルジョン組成物及び木材の処理方法 |
| CN102459420A (zh) * | 2009-06-19 | 2012-05-16 | 蓝星有机硅法国公司 | 通过在非金属催化剂存在下脱氢缩合可交联的有机硅组合物 |
| CN102575011B (zh) | 2009-06-19 | 2014-03-12 | 蓝星有机硅法国公司 | 通过在非金属催化剂存在下脱氢缩合可交联的有机硅组合物 |
| EP2665788A1 (en) | 2010-06-30 | 2013-11-27 | 3M Innovative Properties Company | Curable composition comprising dual reactive silane functionality |
| EP2588550A1 (en) | 2010-06-30 | 2013-05-08 | 3M Innovative Properties Company | Curable polysiloxane coating composition |
| WO2013074299A1 (en) | 2011-11-15 | 2013-05-23 | 3M Innovative Properties Company | Fluorinated coatings with lubricious additive |
| EP2867316A2 (en) | 2012-06-27 | 2015-05-06 | 3M Innovative Properties Company | Moisture-curable polysiloxane coating composition |
-
2013
- 2013-06-17 EP EP13731608.9A patent/EP2867316A2/en not_active Withdrawn
- 2013-06-17 JP JP2015520273A patent/JP6150889B2/ja not_active Expired - Fee Related
- 2013-06-17 US US14/407,776 patent/US9175188B2/en active Active
- 2013-06-17 WO PCT/US2013/046072 patent/WO2014025456A2/en not_active Ceased
- 2013-06-17 CN CN201380034418.8A patent/CN104540909A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015527436A (ja) | 2015-09-17 |
| WO2014025456A3 (en) | 2014-05-08 |
| EP2867316A2 (en) | 2015-05-06 |
| CN104540909A (zh) | 2015-04-22 |
| US20150141570A1 (en) | 2015-05-21 |
| US9175188B2 (en) | 2015-11-03 |
| WO2014025456A2 (en) | 2014-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6150889B2 (ja) | 水分硬化性ポリシロキサンコーティング組成物 | |
| JP5818890B2 (ja) | 二重反応性シラン官能基を含む硬化性組成物 | |
| JP6151639B2 (ja) | 硬化性ポリシロキサンコーティング組成物 | |
| US9006336B2 (en) | Curable polysiloxane coating composition | |
| US9035008B2 (en) | Curable-on-demand polysiloxane coating composition | |
| JP2017509730A (ja) | 硬化性オルガノシロキサンオリゴマー組成物 | |
| US8968869B2 (en) | Curable-on-demand polysiloxane coating composition | |
| US9006357B2 (en) | Curable polysiloxane composition | |
| JP2017517587A (ja) | フルオロアルキルシリコーン | |
| JP5600900B2 (ja) | 撥水剤組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160413 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20160413 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20161221 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170110 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170407 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20170425 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170523 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 6150889 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |