WO2022064460A1 - Copolymère de polysiloxane et composition de revêtement préparée à partir de celui-ci - Google Patents
Copolymère de polysiloxane et composition de revêtement préparée à partir de celui-ci Download PDFInfo
- Publication number
- WO2022064460A1 WO2022064460A1 PCT/IB2021/058796 IB2021058796W WO2022064460A1 WO 2022064460 A1 WO2022064460 A1 WO 2022064460A1 IB 2021058796 W IB2021058796 W IB 2021058796W WO 2022064460 A1 WO2022064460 A1 WO 2022064460A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- coating composition
- range
- copolymer
- polysiloxane copolymer
- predetermined
- Prior art date
Links
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 118
- -1 polysiloxane copolymer Polymers 0.000 title claims abstract description 100
- 239000008199 coating composition Substances 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 32
- 230000008569 process Effects 0.000 claims abstract description 29
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000012530 fluid Substances 0.000 claims description 33
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 239000000049 pigment Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000002002 slurry Substances 0.000 claims description 16
- 239000004606 Fillers/Extenders Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- 125000002524 organometallic group Chemical group 0.000 claims description 14
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 12
- 230000000996 additive effect Effects 0.000 claims description 12
- 239000011521 glass Substances 0.000 claims description 12
- 239000004005 microsphere Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000003822 epoxy resin Substances 0.000 claims description 10
- 229920000647 polyepoxide Polymers 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 7
- 239000004615 ingredient Substances 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical group CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 5
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 claims description 5
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 4
- 239000001293 FEMA 3089 Substances 0.000 claims description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002518 antifoaming agent Substances 0.000 claims description 4
- 229940106691 bisphenol a Drugs 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical group 0.000 claims description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical class O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- 239000010445 mica Substances 0.000 claims description 3
- 229910052618 mica group Inorganic materials 0.000 claims description 3
- 239000002808 molecular sieve Substances 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- XHHXXUFDXRYMQI-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;titanium Chemical compound [Ti].OCCN(CCO)CCO XHHXXUFDXRYMQI-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229920002396 Polyurea Polymers 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000002270 dispersing agent Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- WIEGKKSLPGLWRN-UHFFFAOYSA-N ethyl 3-oxobutanoate;titanium Chemical compound [Ti].CCOC(=O)CC(C)=O WIEGKKSLPGLWRN-UHFFFAOYSA-N 0.000 claims description 2
- 239000010439 graphite Substances 0.000 claims description 2
- 229910002804 graphite Inorganic materials 0.000 claims description 2
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical class [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920003226 polyurethane urea Polymers 0.000 claims description 2
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000008347 soybean phospholipid Substances 0.000 claims description 2
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 claims description 2
- 229910000165 zinc phosphate Inorganic materials 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 17
- 238000005260 corrosion Methods 0.000 abstract description 13
- 230000007797 corrosion Effects 0.000 abstract description 13
- 239000011248 coating agent Substances 0.000 abstract description 9
- 238000009413 insulation Methods 0.000 abstract description 6
- 230000000052 comparative effect Effects 0.000 description 10
- VCESGVLABVSDRO-UHFFFAOYSA-L 2-[4-[4-[3,5-bis(4-nitrophenyl)tetrazol-2-ium-2-yl]-3-methoxyphenyl]-2-methoxyphenyl]-3,5-bis(4-nitrophenyl)tetrazol-2-ium;dichloride Chemical compound [Cl-].[Cl-].COC1=CC(C=2C=C(OC)C(=CC=2)[N+]=2N(N=C(N=2)C=2C=CC(=CC=2)[N+]([O-])=O)C=2C=CC(=CC=2)[N+]([O-])=O)=CC=C1[N+]1=NC(C=2C=CC(=CC=2)[N+]([O-])=O)=NN1C1=CC=C([N+]([O-])=O)C=C1 VCESGVLABVSDRO-UHFFFAOYSA-L 0.000 description 9
- 125000004344 phenylpropyl group Chemical group 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 238000012993 chemical processing Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000001351 cycling effect Effects 0.000 description 2
- 230000032798 delamination Effects 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005297 material degradation process Methods 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000002470 thermal conductor Substances 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
-
- 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- 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
- 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
- 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
- C09D183/10—Block or graft copolymers containing polysiloxane sequences
-
- 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
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
Definitions
- the present disclosure relates to a polysiloxane copolymer and a coating composition prepared therefrom. Particularly, the present disclosure relates to a polysiloxane copolymer and a process for its preparation. Further, the present disclosure relates to a coating composition comprising the polysiloxane copolymer and a process for its preparation.
- Cyclic stress refers to the repetitive occurrence and redistribution of forces acting on a material. Periodic or regular cyclic stress conditions lead to increased wear and tear of the material, thus increasing the rate of material degradation and failure.
- Thinning refers to a step in the preparation of a coating composition, wherein a suitable solvent is added to the coating composition for reducing thickness to obtain the coating composition with desirable consistency.
- Polysiloxane polymers are mainly used in the protective coatings, adhesives, sealants, stationary, craft and other various applications. Generally, polysiloxane polymers are known to impart flexibility, impact strength, weather and high heat resistance in end use applications. Polysiloxane polymers can also be combined with resins of other functionality to tune the properties of the final product such as when the polysiloxane polymer is combined with an epoxy resin, which is then cured with amine based curing agent to provide polysiloxane-epoxy resin based product with improved properties such as impact resistance, flexibility, and corrosion resistance. However, these polysiloxane-epoxy resin based products generally sustain maximum up to 300 °C temperature.
- the use of the high molecular weight polysiloxane polymer is preferred, however the use of the high molecular weight polysiloxane polymer leads to the loss of flexibility of the final product after exposure to the high temperature environment and hence results in delamination from the substrate at higher temperatures. Further, if the lower molecular weight polysiloxane polymers are used to maintain the flexibility of the final product at a high temperature, longer curing time/ heat based curing/ crosslinking agent is required to cure the product to get the desired crosslinking density. The longer curing time and use of the heat or crosslinking agents are detrimental for flexibility of the final product at higher temperatures.
- CUI Corrosion under Insulation
- the conventional CUI coatings that are available in market suffer from limitations such as poor performance at higher temperatures (> 450°C) and cyclic stress. Moreover, most of the conventional CUI coatings are known for their heavy settling property due to which the applicator faces difficulties while applying the coating.
- An object of the present disclosure is to ameliorate one or more problems of the prior art or to at least provide a useful alternative.
- Another object of the present disclosure is to provide a polysiloxane copolymer.
- Yet another object of the present disclosure is to provide a process for the preparation of a polysiloxane copolymer.
- Still another object of the present disclosure is to provide a polysiloxane copolymer that is cured at an ambient temperature.
- Yet another object of the present disclosure is to provide a coating composition comprising the polysiloxane copolymer that maintains flexibility at a temperature greater than 500 °C.
- Still another object of the present disclosure is to provide a coating composition that can withstand cycling heat resistance, high stress level and weathering.
- Yet another object of the present disclosure is to provide a coating composition that has a comparatively better adhesion on mild steel and stainless steel surfaces and has better abrasion resistance and high thermal shock resistance.
- Still another object of the present disclosure is to provide a coating composition that controls the corrosion under insulation (CUI).
- Yet another object of the present disclosure is to provide a process for the preparation of a coating composition comprising the polysiloxane copolymer.
- the present disclosure relates to a polysiloxane copolymer being a product of part A comprising an alkyl and/or aryl substituted silanol-functional silicone prepolymer and part B comprising an alkyl and/or aryl substituted alkoxy- functional silicone prepolymer, wherein a ratio of the part A to the part B is in the range of 1:0.5 to 1:2.
- the present disclosure further relates to a process for the preparation of the polysiloxane copolymer.
- the process comprises the step of mixing part A comprising an alkyl and/or aryl substituted silanol-functional silicone prepolymer and part B comprising an alkyl and/or aryl substituted alkoxy- functional silicone prepolymer in a fluid medium in the presence of an organometallic catalyst, optionally using a flexibilizer at a predetermined temperature for a predetermined time period to obtain the polysiloxane copolymer, wherein a ratio of the part A to the part B is in the range of 1:0.5 to 1:2.
- the present disclosure relates to a coating composition
- a coating composition comprising a polysiloxane copolymer; at least one pigment; at least one extender; at least one modifying agent; at least one additive; hollow glass microspheres; and at least one fluid medium.
- the present disclosure relates to a process for preparing the coating composition.
- the process comprises a step of mixing predetermined amounts of a polysiloxane copolymer, at least one modifying agent and at least one additive in a first fluid medium under stirring at a first predetermined speed for a first predetermined time period at a first predetermined temperature to obtain a mill base.
- Predetermined amounts of at least one pigment and at least one extender are added to the mill base followed by grinding at a second predetermined speed for a second predetermined time period at a second predetermined temperature to obtain a slurry.
- a predetermined amount of glass microspheres is added to the slurry followed by thinning by using at least one second fluid medium at a third predetermined speed for a third predetermined time period at a third predetermined temperature to obtain a homogenized slurry.
- the homogenized slurry is cooled to a temperature in the range of 20 °C to 28 °C followed by filtration to obtain the coating composition.
- Embodiments are provided so as to thoroughly and fully convey the scope of the present disclosure to the person skilled in the art. Numerous details are set forth, relating to specific components, and methods, to provide a complete understanding of embodiments of the present disclosure. It will be apparent to the person skilled in the art that the details provided in the embodiments should not be construed to limit the scope of the present disclosure. In some embodiments, well-known processes, well-known apparatus structures, and well-known techniques are not described in detail.
- Corrosion under Insulation is one of the major problems for oil and gas pipelines in refining, power and chemical processing industries, as well as in the marine environments.
- the conventional CUI coatings that are available in the market suffer from limitations such as poor performance at higher temperatures (> 450°C) and cyclic stress.
- most of the conventional CUI coatings are known for their heavy settling property due to which the applicator faces difficulties while applying the coating.
- Polysiloxane polymeric material finds variety of applications in the coating, adhesive, sealant, stationary, craft industries because of the well-known properties of the product made therefrom.
- the polysiloxane polymer when combined with the other resins having functionality such as epoxy resins or acrylic resins, the so obtained product has the improved properties (when compared to the product made from either of the materials solely).
- the product prepared from the modified and unmodified polysiloxane based polymers possess the drawback of loss of flexibility after exposure of the same to high temperatures which results into delamination from the substrate.
- the present disclosure provides a polysiloxane copolymer and a process for its preparation. Further, the present disclosure provides a coating composition comprising the polysiloxane copolymer and a process for its preparation.
- the present disclosure provides a polysiloxane copolymer being a reaction product of part A comprising an alkyl and/or aryl substituted silanol-functional silicone prepolymer and part B comprising an alkyl and/or aryl substituted alkoxy- functional silicone prepolymer, wherein a ratio of the part A to the part B is in the range of 1:0.5 to 1:2.
- the polysiloxane copolymer is represented by formula I:
- R 1 , R2 , R 3 and R 4 are independently selected from methyl, ethyl, propyl, butyl, pentyl, hexyl and aryl; and x and y are integers independently selected from 1 to 6.
- the part A comprising an alkyl and/or aryl substituted silanol-functional silicone prepolymer is represented by formula la: wherein,
- R 1 and R 4 are independently selected from methyl, ethyl, propyl, butyl, pentyl, hexyl and aryl; and n is an integers selected from 1 to 6.
- the part B comprising an alkyl and/or aryl substituted alkoxy- functional silicone prepolymer is represented by formula lb:
- R 2 and R 3 are independently selected from methyl, ethyl, propyl, butyl, pentyl, hexyl and aryl; and n is an integers selected from 1 to 6.
- the polysiloxane copolymer of the present disclosure is formulated such that the rates of internal polymerization reaction can be controlled.
- the polymerization reaction can take place over a broad temperature range, including ambient and high temperatures.
- the alkyl group in the part A and the part B is independently selected from methyl, ethyl, propyl, butyl, pentyl and hexyl.
- the aryl group in the part A and the part B is independently selected from phenyl and benzyl.
- the Part A and Part B independently comprises two or more reactive functionalities per repeat unit comprising two Si atom (-[-Si-O-Si]-O-).
- the reactive functionality is silanol (-Si-OH).
- the reactive functionality is alkoxy silane (-Si-O-C).
- the part A and the Part B independently comprises at least one aryl substituent per repeating unit comprising two Si atom (-[-Si-O- Si]-O-).
- the part A is optionally modified by incorporating polyurethane or polyurea based flexibilizer.
- the part B is optionally modified with amine/epoxy/NCO/SH functional silane or their adducts with epoxy.
- the backbone of the polysiloxane copolymer is kinetically optimized in such a way that a pre-determined molecular weight of the polysiloxane copolymer is obtained.
- the pre-determined molecular weight of the polysiloxane copolymer is in range of 2000 g/mol to 15000 g/mol.
- the polysiloxane copolymer is monomodal or bimodal depending on the specific application.
- the polysiloxane copolymer of the present disclosure is one component, ambient or low temperature moisture curable, and storage stable.
- the polysiloxane copolymer of the present disclosure can be used in industries such as coating, adhesive, sealant, construction chemicals, admixture, stationary adhesives, and craft materials.
- the polysiloxane copolymer is used for preparing a coating composition that maintains flexibility at a temperature in the range of 500 °C to 1000 °C.
- the present disclosure provides a process for preparation of the polysiloxane copolymer.
- the process comprises the step of mixing part A comprising an alkyl and/or aryl substituted silanol-functional silicone prepolymer and part B comprising an alkyl and/or aryl substituted alkoxy-functional silicone prepolymer in a fluid medium in the presence of an organometallic catalyst optionally by using a flexibilizer at a predetermined temperature for a predetermined time period to obtain the polysiloxane copolymer, wherein a ratio of the part A to the part B is in the range of 1:0.5 to 1:2.
- the organometallic catalyst is selected from tetra-isopropyl titanate (Tyzor TPT), tetra-n-butyl titanate (Tyzor TNBT), Tetrakis(2-ethylhexyl) orthotitanate (Tyzor TOT), titanium tetrapropanolate (Tyzor NPT), a mixture of tetra-isopropyl and tetra-n-butyl titanate (Tyzor TPT-20 B), titanium acetylacetonates (Tyzor AA, Tyzor AA-65, Tyzor AA-75, Tyzor AA-105, Tyzor GBA, Tyzor GBO), titanium ethylacetoacetate (Tyzor DC), triethanolamine titanium complex (Tyzor TE), organotin carboxylate (TIB KAT 218) and organotin carboxylate (DABCO T12).
- TPT tetra-iso
- the fluid medium is nonalcoholic or non-glycolic.
- the fluid medium is at least one selected from the group consisting of ortho-xylene, mineral turpentine oil, solvent C-IX (a mixture of aromatic hydrocarbon solvents), n- butanol, Butyl acetate, methyl isobutyl ketone (MIBK) and methyl ethyl ketone (MEK).
- the fluid medium is orthoxylene.
- the flexibilizer is at least one selected from the group consisting of Lapox Bll (unmodified epoxy resin based on bisphenol-A), Lapox P101 (75% solution of solid epoxy resin (type-1) in xylene), DER-664U (epoxy resin of epichlorohydrin and bisphenol A), Dynasylan AMEO (3- aminopropyltriethoxy silane), adduct of Lapox Bl l and Dynasylan AMEO, adduct of Lapox P101 and Dynasylan AMEO, adduct of DER-664U and Dynasylan AMEO, Silquest A-link- 35 (isocyanate functional trimethoxy silane), Coatosil T-Cure (mercapto silane), adduct of Silquest A-link-35 and Coatosil T-Cure, adduct of Dynasylan AMEO and Coaosili T-Cure, adduct of Lapox Bl
- Lapox Bl unmodified epoxy resin
- the predetermined time period is in the range of 3 hours to 9 hours. In an exemplary embodiment, the pre-determined time period is 6 hours.
- the present disclosure provides a coating composition
- a coating composition comprising a polysiloxane copolymer; at least one pigment; at least one extender; at least one modifying agent; at least one additive; hollow glass microspheres; and at least one fluid medium.
- the coating composition comprises 10 to 20 wt% of the polysiloxane copolymer with respect to the total amount of the coating composition; 40 to 50 wt% of at least one pigment with respect to the total amount of the coating composition; 20 to 40 wt% of at least one extender with respect to the total amount of the coating composition; 1 to 5 wt% of at least one modifying agent with respect to the total amount of the coating composition; 0.5 to 2 wt% of at least one additive with respect to the total amount of the coating composition; 0.1 to 1 wt% of the hollow glass microspheres with respect to the total amount of the coating composition; and 5 to 15 wt% of at least one fluid medium with respect to the total amount of the coating composition.
- the polysiloxane copolymer is represented by formula I: Formula I wherein,
- R , R , R and R are independently selected from methyl, ethyl, propyl, butyl, pentyl, hexyl and aryl; and x and y are integers independently selected from 1 to 6.
- the polysiloxane copolymer used in the coating composition of the present disclosure provides cycling heat resistant and stress resistant properties to the coating and helps to withstand weathering of the coating.
- the pigment is at least one selected from carbon black pigment, zinc phosphate, zinc oxide and micaceous iron oxide.
- a weight ratio of the pigment to the polysiloxane copolymer is in range of 1:0.15 to 1:0.4. This ratio is very crucial to achieve the desired flexibility and the heat resistance properties in the coating composition.
- the micaceous iron oxide has a lamellar shape.
- the micaceous iron oxide with lamellar shape acts as an inert barrier to the vertical penetration of corrosive elements.
- the extender is at least one selected from silica, mica and steatite.
- the extender is a combination of silica and steatite.
- the extender is a combination of mica and steatite. The extender provides reinforcement to the coatings when applied on the substrate and thus, improves the mechanical properties of the coatings on the substrate.
- the modifying agent is at least one selected from an organic derivative of bentonite clay, modified hectorite (Bentone Jelly), molecular sieves, micronized amide wax, modified silica, trimethoxysilane, graphite, and silicon based defoaming agent.
- the organic derivative of bentonite clay acts as an anti-settling agent and prevents the tendency of heavy settling in the coating composition even after 1 year of shelf life.
- the molecular sieves (Zeolith 141 4A powder) acts as moisture adsorbent with excellent kinetic gas adsorption present in the paint compaction.
- the micronized amide wax, commercially available as Crayvallac ultra is commonly used as rheology modifier that offers very good recoatability for ambient curing solvent-based coatings.
- Graphite powder provides functionality as thermal conductor and corrosion shield. Trimethoxysilane (Silane A- 187) acts as an adhesion promoter.
- the silicon based defoaming agent is polymethylalkylsiloxane (commercially available as BYK 085).
- the silicon based defoaming agent is used to prevent foam and bubble formation during the processing and application of the coating composition.
- the modified silica is a fumed silica aftertreated with DDS (Dimethyldichlorosilane), commercially available as Aerosil 972.
- DDS Dimethyldichlorosilane
- Aerosil 972 The modified silica is generally used in coatings as anti-settling agent, for pigment stabilization and improvement of corrosion protection.
- the additive is at least one selected from a high molecular weight block copolymer (commercially available as Disperbyk 163) and a structured acrylate copolymer (commercially available as Disperbyk 2000) as dispersing agents; and soyalecithin as an emulsifier.
- the fluid medium is at least one selected from mixed xylene, n-butanol, isobutanol, solvent C-IX (a mixture of aromatic hydrocarbon solvents), and mineral turpentine oil.
- the fluid medium is a combination of mixed xylene and isobutanol.
- the fluid medium is a combination of mixed xylene, isobutanol and solvent C-IX (a mixture of aromatic hydrocarbon solvents).
- the hollow glass microspheres used in the coating composition of the present disclosure enhance filler loading, lower the viscosity/improve the flow ability and reduce shrinkage of the coating composition. Further, the hollow glass microspheres enhance higher pigment loading and give high heat resistance along with extreme cryogenic resistance properties to the coating composition.
- the present disclosure provides a process for preparing the coating composition.
- the process comprises a step of mixing predetermined amounts of a polysiloxane copolymer, at least one modifying agent and at least one additive in a first fluid medium under stirring at a first predetermined speed for a first predetermined time period at a first predetermined temperature to obtain a mill base.
- the first predetermined speed is in the range of 200 rpm to 300 rpm.
- the first predetermined time period is in the range of 10 minutes to 15 minutes.
- the first predetermined temperature is in the range of 30 °C to 35 °C.
- Predetermined amounts of at least one pigment and at least one extender are added to the mill base followed by grinding at a second predetermined speed for a second predetermined time period at a second predetermined temperature to obtain a slurry.
- the second predetermined speed is in the range of 1200 rpm to 1500 rpm.
- the second predetermined time period is in the range of 30 minutes to 45 minutes.
- the second predetermined temperature is in the range of 40 °C to 60 °C.
- a predetermined amount of glass microspheres is added to the slurry followed by thinning by using at least one second fluid medium at a third predetermined speed for a third predetermined time period at a third predetermined temperature to obtain a homogenized slurry.
- the third predetermined speed is in the range of 200 rpm to 300 rpm.
- the third predetermined time period is in the range of 10 minutes to 15 minutes.
- the third predetermined temperature is in the range of 35 °C to 40 °C.
- the homogenized slurry is cooled to a temperature in the range of 20 °C to 28 °C followed by filtration to obtain the coating composition.
- the coating composition prepared by using the polysiloxane copolymer can maintain its flexibility at a temperature in the range of 500 °C to 1000 °C on suitable substrates, particularly upto 800 °C.
- the coating composition prepared by using the polysiloxane copolymer is characterized by having the following properties:
- Example- 1 48 g of an silanol-functional phenylpropyl polysiloxane prepolymer and 27g of an alkoxyfunctional phenyl polysiloxane prepolymer were mixed in 25ml of ortho-xylene (fluid medium) at 120 °C for 9 h to obtain the poly siloxane copolymer.
- Tyzor TNBT organometallic catalyst
- Table 1 Performance comparison of polysiloxane copolymers between examples 1-6 of the present disclosure and comparative examples
- the polysiloxane copolymer of Examples 1-6 when studied for the time required for drying the film on mild 10 steel at ambient temperature, was found to be in the range of 4 to 6 hours, whereas, for the polysiloxane copolymer of Comparative Examples I-II, it was found to be non-drying and for Comparative Example III, it was 12 hours.
- Predetermined amounts of the polysiloxane copolymer prepared in Example 2 of Experiment 1, at least one modifying agent and at least one additive were mixed in a first fluid medium under stirring at a first predetermined speed for a first predetermined time period at a first 5 predetermined temperature to obtain a mill base.
- Predetermined amounts of at least one pigment and at least one extender were added to the mill base followed by grinding at a second predetermined speed for a second predetermined time period at a second predetermined temperature to obtain a slurry.
- a predetermined amount of glass microspheres was added to the slurry followed by thinning by using at least one second fluid medium at a 10 third predetermined speed for a third predetermined time period at a third predetermined temperature to obtain a homogenized slurry.
- the homogenized slurry was cooled to 25 °C followed by filtration to obtain the coating composition.
- the coating composition of the examples 1-8 were prepared by following the process as 15 disclosed herein above, with variable ingredients with variable amounts.
- Table 2a The ingredients with variable amounts used in the process for preparing the coating composition and the test results of the coating composition (Examples 1-8).
- Table 2b The ingredients with variable amounts used in the process for preparing the coating composition and the test results of the coating composition (Examples 9-16).
- the examples 1 to 16 were designed by varying the ingredient type and amount. The experiments are presented as a sequence to achieve desired physical- mechanical and heat resistance properties. The coating composition of example 16 shows the satisfactory performance as compared to the coating compositions of examples 1-15.
- Table 3a indicates the mechanical properties such as impact test, abrasion resistance and adhesion strength of optimized formulation.
- Table 3b shows the chemical resistance and corrosion resistance properties of coating in different corrosive environments.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (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)
- Paints Or Removers (AREA)
Abstract
La présente invention concerne un copolymère de polysiloxane et un procédé pour sa préparation. Le copolymère de polysiloxane de la présente invention peut être durci à une température ambiante et est maintenu à des températures élevées sans perte de souplesse. En outre, la présente invention concerne une composition de revêtement comprenant le copolymère de polysiloxane et un procédé de préparation de la composition de revêtement. La composition de revêtement de la présente invention peut être utilisée pour un revêtement à résistance thermique élevée et le revêtement anti-corrosion sous isolation (CUI).
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN202021041851 | 2020-09-26 | ||
IN202021041851 | 2020-09-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022064460A1 true WO2022064460A1 (fr) | 2022-03-31 |
Family
ID=80844565
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2021/058796 WO2022064460A1 (fr) | 2020-09-26 | 2021-09-27 | Copolymère de polysiloxane et composition de revêtement préparée à partir de celui-ci |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2022064460A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116144262A (zh) * | 2023-03-27 | 2023-05-23 | 天津灯塔涂料工业发展有限公司 | 有机硅复配涂料及其制备方法 |
CN117659862A (zh) * | 2023-12-18 | 2024-03-08 | 北京和尔泰新材料科技有限公司 | 一种耐高温防护涂料及其制备和使用方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5804616A (en) * | 1993-05-19 | 1998-09-08 | Ameron International Corporation | Epoxy-polysiloxane polymer composition |
US8772407B2 (en) * | 2007-09-17 | 2014-07-08 | Ppg Industries Ohio, Inc. | One component polysiloxane coating compositions and related coated substrates |
-
2021
- 2021-09-27 WO PCT/IB2021/058796 patent/WO2022064460A1/fr active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5804616A (en) * | 1993-05-19 | 1998-09-08 | Ameron International Corporation | Epoxy-polysiloxane polymer composition |
US8772407B2 (en) * | 2007-09-17 | 2014-07-08 | Ppg Industries Ohio, Inc. | One component polysiloxane coating compositions and related coated substrates |
Non-Patent Citations (1)
Title |
---|
SHIMOJIMA ATSUSHI, KURODA KAZUYUKI: "Alkoxy- and Silanol-Functionalized Cage-Type Oligosiloxanes as Molecular Building Blocks to Construct Nanoporous Materials", MOLECULES, vol. 25, no. 3, 1 January 2020 (2020-01-01), XP055922306, DOI: 10.3390/molecules25030524 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116144262A (zh) * | 2023-03-27 | 2023-05-23 | 天津灯塔涂料工业发展有限公司 | 有机硅复配涂料及其制备方法 |
CN117659862A (zh) * | 2023-12-18 | 2024-03-08 | 北京和尔泰新材料科技有限公司 | 一种耐高温防护涂料及其制备和使用方法 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR102359987B1 (ko) | 중공 유리 구체 및 도전성 안료를 포함하는 부식 방지 아연 프라이머 코팅 조성물 | |
CA2939788C (fr) | Anti-corrosif compositions de revetement primaires a base de zinc | |
WO2022064460A1 (fr) | Copolymère de polysiloxane et composition de revêtement préparée à partir de celui-ci | |
JP2006520841A (ja) | クリアコート組成物としておよびプライマー組成物として有用なポリトリメチレンエーテルジオールを含有するコーティング組成物 | |
CN109971305B (zh) | 无溶剂高温防腐涂料、防腐涂层及容器 | |
US6180726B1 (en) | High temperature resistant coating composition and method of using thereof | |
AU2005280622B2 (en) | Flexible, impact resistant primer | |
CN101636456B (zh) | 用于氟碳涂料组合物的超分散剂 | |
CN110724440A (zh) | 一种管道补口用耐低温双组份无溶剂环氧涂料 | |
WO1982000651A1 (fr) | Poudres de revetement epoxy | |
WO2012147569A1 (fr) | Procédé de fabrication de produit peint et de miroir | |
EP3875556A1 (fr) | Revêtement | |
Baledon et al. | Novel Silicone Hardener for Eco-Friendly Heat Resistant Coatings | |
Witucki | Polysiloxane Hybrid Coatings |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 21871813 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 21871813 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 523440141 Country of ref document: SA |