CN110819229A - Curable composition - Google Patents
Curable composition Download PDFInfo
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- CN110819229A CN110819229A CN201910664092.6A CN201910664092A CN110819229A CN 110819229 A CN110819229 A CN 110819229A CN 201910664092 A CN201910664092 A CN 201910664092A CN 110819229 A CN110819229 A CN 110819229A
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- curable composition
- mass
- coating film
- component
- steel sheet
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- 239000000203 mixture Substances 0.000 title claims abstract description 83
- 238000009835 boiling Methods 0.000 claims abstract description 41
- 239000003960 organic solvent Substances 0.000 claims abstract description 23
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 21
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 21
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 20
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 16
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 229920002050 silicone resin Polymers 0.000 claims abstract description 12
- 238000000576 coating method Methods 0.000 claims description 80
- 239000011248 coating agent Substances 0.000 claims description 79
- 229910000831 Steel Inorganic materials 0.000 claims description 41
- 239000010959 steel Substances 0.000 claims description 41
- 239000004744 fabric Substances 0.000 claims description 23
- 238000001035 drying Methods 0.000 claims description 21
- 239000000835 fiber Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 238000010276 construction Methods 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 37
- 238000005299 abrasion Methods 0.000 abstract description 20
- 238000003860 storage Methods 0.000 abstract description 14
- 239000010408 film Substances 0.000 description 66
- 150000001875 compounds Chemical class 0.000 description 24
- 239000000047 product Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 11
- -1 aminooxy, oximino Chemical group 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229920001410 Microfiber Polymers 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000004745 nonwoven fabric Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 229940093858 ethyl acetoacetate Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000002783 friction material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical class CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- GQSZLMMXKNYCTP-UHFFFAOYSA-K aluminum;2-carboxyphenolate Chemical compound [Al+3].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O GQSZLMMXKNYCTP-UHFFFAOYSA-K 0.000 description 1
- QVERTZDPVWSNIM-UHFFFAOYSA-K aluminum;3-oxoheptanoate Chemical compound [Al+3].CCCCC(=O)CC([O-])=O.CCCCC(=O)CC([O-])=O.CCCCC(=O)CC([O-])=O QVERTZDPVWSNIM-UHFFFAOYSA-K 0.000 description 1
- OFEPSGLLYPYMDB-UHFFFAOYSA-K aluminum;hexanoate Chemical compound [Al+3].CCCCCC([O-])=O.CCCCCC([O-])=O.CCCCCC([O-])=O OFEPSGLLYPYMDB-UHFFFAOYSA-K 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000013522 chelant Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- QPAQOQRHCLJMIL-UHFFFAOYSA-N diethoxy(propan-2-yloxy)alumane Chemical class CCO[Al](OCC)OC(C)C QPAQOQRHCLJMIL-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 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 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- JTBKFHQUYVNHSR-UHFFFAOYSA-N propan-2-yloxyalumane Chemical class CC(C)O[AlH2] JTBKFHQUYVNHSR-UHFFFAOYSA-N 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical class [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical class [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber 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
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Abstract
The purpose of the present invention is to provide a curable composition having excellent water repellency, water-slipping property, abrasion resistance, storage property, and workability. The curable composition of the present invention is a curable composition comprising 1.0 part by mass of the component (A) and 0.05 to 5.0 parts by mass of the component (B), and 5.5 to 28 parts by mass of the component (C). (A) A silicone resin having a hydrolyzable group, (B) an aluminum catalyst, and (C) a hydrocarbon organic solvent having an initial boiling point of 201 to 240 ℃.
Description
Technical Field
The present invention relates to a curable composition which requires a specific composition ratio of a silicone resin having a hydrolyzable group, an aluminum catalyst, and a hydrocarbon organic solvent having a specific initial boiling point, and relates to a curable composition which can form a coating film which is cured on each substrate at room temperature to impart water repellency, water-sliding property, and durability.
Background
Conventionally, a liquid curable composition has been applied to a coated steel sheet of an automobile body, a railway vehicle, or the like for the purpose of protecting and improving the appearance. As such a curable composition, for example, a composition in which a moisture-curable silicone oligomer, a curing catalyst, and a specific silicone oil are dissolved or dispersed in a petroleum-based solvent, an alcohol-based solvent, an aromatic hydrocarbon-based solvent, or the like is disclosed (japanese patent application laid-open No. 2007-161988).
Disclosure of Invention
However, the curable composition disclosed in jp 2007-161988 a is excellent in antifouling property, and on the other hand, it is difficult to satisfy all of the properties of storage property and workability in an uncured state, water repellency of a cured coating film, water-slipping property (water-slipping property), and abrasion resistance at the same time.
The present invention has been made in view of the above problems, and an object thereof is to provide a curable composition having excellent storability in an uncured state, excellent water repellency, water-slipping property and abrasion resistance as a cured product, and excellent workability of the curable composition.
Another object of the present invention is to provide a method for forming a coating film using a curable composition having excellent storability in an uncured state, excellent water repellency, water-slipping property, and abrasion resistance as a cured product, and excellent workability of the curable composition.
The present inventors have conducted intensive studies to achieve the above object, and as a result, have found a curable composition having excellent storability in an uncured state, excellent water repellency as a cured product, water repellency, water-slipping property, abrasion resistance, and excellent workability of the curable composition, and a method for forming a coating film thereof, and have completed the present invention.
The gist of the present invention will be described below. The first embodiment of the present invention is a curable composition comprising the following components (a) to (C), wherein the component (B) is 0.05 to 5.0 parts by mass and the component (C) is 5.5 to 28 parts by mass, based on 1.0 part by mass of the component (a).
(A) Silicone resin having hydrolyzable group
(B) Aluminum-based catalyst
(C) Hydrocarbon organic solvent having initial boiling point of 201-240 deg.C
A second embodiment of the present invention is the curable composition according to the first embodiment, wherein the component (B) is 0.095 to 0.19 parts by mass relative to 1.0 part by mass of the component (a).
A third embodiment of the present invention is the curable composition according to the first or second embodiment, wherein the component (C) is 9.97 to 20 parts by mass relative to 1.0 part by mass of the component (a).
A fourth embodiment of the present invention is a method for forming a coating film, wherein the curable composition according to the first to third embodiments is subjected to the following steps 1 to 5 in this order.
Step 1: coating step
And a step 2: 1 st drying step
Step 3: the step of wiping the coating film of the curable composition with the dried fiber or cloth for the first time
And step 4: 2 nd drying step
Step 5: 2 nd wiping the coating film of the curable composition with the dried fiber or cloth
A fifth embodiment of the present invention is the curable composition according to any one of the first to third embodiments, which is used for forming a coating film on a surface of a metallic steel sheet or a coated steel sheet.
A sixth embodiment of the present invention is the curable composition according to the fifth embodiment, wherein the metal steel sheet or the coated steel sheet is a part of a vehicle body of an automobile, a railway vehicle, heavy machinery, a ship, an airplane, agricultural machinery, or construction machinery.
Detailed Description
The curable composition of the present invention comprises: (A) 1.0 part by mass of a silicone resin having a hydrolyzable group; (B) 0.05 to 5.0 parts by mass of an aluminum catalyst; and (C) 5.5 to 28 parts by mass of a hydrocarbon organic solvent having an initial boiling point of 201 to 240 ℃. The curable composition of the present invention comprises: excellent storability in an uncured state, excellent water repellency, water-slipping property and abrasion resistance as a cured product, and excellent workability of the curable composition. The present invention also provides a curable composition which can provide a cured coating film having excellent water repellency and good abrasion resistance to a vehicle body of an automobile, an airframe of an airplane, and the like. Further, it is possible to provide a method for producing a curable composition capable of providing a cured coating film having excellent water repellency and excellent abrasion resistance to a vehicle body of an automobile, a body of an airplane, or the like.
Hereinafter, embodiments of the present invention will be described. The present invention is not limited to the following embodiments. In the present specification, unless otherwise specified, the operation and the measurement of physical properties and the like are performed under the conditions of room temperature (20 ℃ to 25 ℃) and relative humidity of 40% RH to 50% RH. In the present specification, "X to Y" indicating a range includes X and Y, and means "X or more and Y or less".
[ curable composition ]
The details of the present invention will be described below.
The component (a) that can be used in the present invention is not particularly limited as long as it is a silicone resin having a hydrolyzable group. The "silicone resin" is a resin composed of siloxane bonds (Si — O — Si), and is cured by heating, a catalyst, or the like. Examples of the "hydrolyzable group" include: alkoxy, alkenyloxy, acyloxy, aminooxy, oximino, amido, and the like. Among them, the hydrolyzable group contained in the silicone resin is preferably an alkoxy group because of easy handling. The component (a) is a component which plays a major role in exhibiting properties such as water repellency, water lubricity, and abrasion resistance in a cured coating film formed from the curable composition of the present invention.
Among these, the silicone resin having a hydrolyzable group is a polymer obtained by partially hydrolyzing and condensing an alkoxysilane compound having a hydrolyzable group (also referred to as "partial hydrolysis condensation" in the present specification) with a known catalyst such as an acid, a base, an organotin compound, an organotitanium compound, or the like, and is an organosilicon compound having a hydrolyzable group derived from the above silane compound at a molecular chain terminal, a side chain, or the like, and forming a linear structure, a branched structure, or a three-dimensional network structure.
Preferred examples of the alkoxysilane compound having a hydrolyzable group for obtaining the organosilicon compound (silicone resin) include: multifunctional alkoxysilane compounds such as dialkoxysilane compounds, trialkoxysilane compounds, tetraalkoxysilane compounds, and the like, and monoalkoxysilane compounds (monofunctional alkoxysilane compounds). The silane compound may be used alone in 1 kind, or in combination with 2 or more kinds.
The partial hydrolysis-condensation product may be a compound obtained by using only 1 type of alkoxysilane compound represented by the following formula (1), or may be a compound obtained by combining 2 or more types.
R1 x-Si(OR2)4-xThe formula (1)
In the above formula (1), R1And R2Is an aliphatic hydrocarbon group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, each of which may have a substituent independently. Wherein R is1And R2May be the same or different. The aliphatic hydrocarbon group having 1 to 8 carbon atoms is not particularly limited, and examples thereof include: and linear or branched alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, heptyl, octyl, and 2-ethylhexyl. The alicyclic hydrocarbon group having 3 to 10 carbon atoms is not particularly limited, and examples thereof include: and cyclic alkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The aromatic hydrocarbon group having 6 to 10 carbon atoms is not particularly limited, and examples thereof include a phenyl group, a naphthyl group, and a tolyl group.
When these groups have a substituent, the substituent is not particularly limited, and examples thereof include: alkyl groups, alkenyl groups, aryl groups, halogen atoms, nitro groups, cyano groups, hydroxyl groups, carboxyl groups, and the like. However, the same form as that of the group before substitution is excluded from the structure after substitution. For example R1In the case of an alkyl group, the alkyl group is not further substituted with an alkyl group.
R1And R2Preferably, each of the groups is independently selected from an aliphatic hydrocarbon group having 1 to 8 carbon atoms and an aromatic hydrocarbon group having 6 to 10 carbon atomsThe substituents in (1) are more preferably each independently a substituent selected from the group consisting of a methyl group, an ethyl group, a propyl group and a phenyl group, and particularly preferably each independently a methyl group or a phenyl group. In particular R2Preferably methyl.
In the formula (1), x is an integer of 0 to 3. When the alkoxysilane compound represented by the above formula (1) is used alone, x is preferably an integer of 0 to 2, and more preferably 1 or 2. When 2 or more kinds of the alkoxysilane compounds are used, it is preferable to use at least a first alkoxysilane compound in which x is an integer of 1 to 3 and a second alkoxysilane compound in which x is an integer of 0 to 3 in combination (except for the embodiment in which x is 3 in both the first alkoxysilane compound and the second alkoxysilane compound). In the above formula (1), when used alone or in combination of two or more, a linear structure, a branched structure or a three-dimensional crosslinked structure is formed between the two, and R is partially contained1Radical and OR2And (4) a base.
Examples of the method for producing the component (a) include: a method in which a known hydrolysis catalyst is added to the alkoxysilane compound represented by the above formula (1), and stirring is performed while heating in the presence of water, thereby causing partial hydrolytic condensation, but is not limited thereto.
As the component (A), commercially available products can be used. Examples of the commercially available products of the component (A) include, but are not limited to, KC-89S, KR-515, KR-500, X-40-9225, X-40-9246, X-40-9250, KR-401N, X-40-9227, XR31-B2733 of Momentive Performance Materials Japan contract Co., Ltd., and SH550 of Toronto Corning Co., Ltd. These may be used alone, or two or more of them may be used in combination.
The component (B) that can be used in the present invention is not particularly limited as long as it is an aluminum-based catalyst. The component (B) contained in the curable composition of the present invention is an aluminum-based catalyst, and the hydrolyzable group (Si-OR) contained in the component (A) is2) A compound which reacts with moisture in the air or the like and is used for a condensation reaction.
In the present invention, by using an aluminum-based catalyst as a condensation reaction catalyst, the storage stability can be stabilized, and the effect of improving the ease of handling particularly in surface construction of automobile bodies and the like can be obtained because the coating film is not cured too early.
As the aluminum-based catalyst, various organoaluminum compounds are known, and specific examples thereof include: alkoxy compounds such as trimethoxyaluminum, triethoxyaluminum, isopropoxyaluminum, isopropoxydiethoxyaluminum, and tributoxyaluminum; chelate compounds such as aluminum isopropoxide, aluminum sec-butoxide, aluminum tert-butoxide, aluminum tris (hexafluoroacetylacetonate), aluminum tris (ethylacetoacetate), aluminum isopropoxybis (ethylacetoacetate), aluminum tris (n-propylacetoacetate), aluminum tris (isopropylacetacetate), aluminum tris (n-butylacetate), aluminum trisalicylate, aluminum tris (2-ethoxycarbonylphenol), aluminum bis (ethylacetoacetate) monoacetylpyruvate, aluminum tris (acetylacetonate) are commercially available, and DX-9740, CAT-AC from CRYSTAL CO., and Alumichelate D from CHUAN FINE CHEMICAL CO., LTD, but not limited thereto. These may be used alone, or two or more of them may be used in combination.
The amount of the component (B) in the present invention is 0.05 to 5.0 parts by mass relative to 1.0 part by mass of the component (A). When the amount of the component (B) is 0.05 parts by mass or more, the curing rate can be appropriately adjusted, and the durability of the cured coating film can be obtained. When the amount of the component (B) is 5.0 parts by mass or less, the storage stability (storability) of the curable composition can be maintained without reacting with moisture in the air. The amount of the component (B) is preferably 0.095 to 0.19 parts by mass relative to 1.0 part by mass of the component (A). Within this range, excellent properties are obtained with respect to storage properties in an uncured state and abrasion resistance of the cured coating film.
The component (C) which can be used in the present invention is a hydrocarbon-based organic solvent having an initial boiling point of 201 to 240 ℃. Preferably, the component (C) is a hydrocarbon-based organic solvent having a first boiling point of 205 to 225 ℃. Among them, component (C) is not preferable because when the initial boiling point is less than 201 ℃, the surface of the coating film becomes uneven. (C) When the initial boiling point of the component (C) exceeds 240 ℃, workability of the cured product is deteriorated and abrasion resistance of the cured coating film of the cured product is deteriorated, which is not preferable (comparative examples 3 and 4). The component (C) is not particularly limited as long as it is a hydrocarbon-based organic solvent having an initial boiling point of 201 to 240 ℃. The initial boiling point is a temperature at which a certain liquid is vaporized by boiling when the liquid is a mixture. In the present specification, the initial boiling point is determined by JISK 2601: values obtained by the distillation test method described in 1998. Examples of the component (C) include naphthenes and isoparaffins, and examples of the commercially available product include: ExOR D80 (initial boiling point: 205 ℃ C.) from ExxonMobil, isoparaffins include: ISOPAR M (initial boiling point: 225 ℃ C.) from ExxonMobil, a mixed system of naphthenes and paraffins may be mentioned: SPCN-80 (initial boiling point: 205 ℃ C.) by SPC Japan, etc., but are not limited thereto. These may be used alone, or 2 or more of them may be used in combination.
Further, even if the initial boiling point is outside the above range, 2 or more kinds of hydrocarbon-based organic solvents are mixed, and in the mixture, any hydrocarbon-based organic solvent having an initial boiling point of 201 to 240 ℃ can be used as the component (C). The initial boiling point of the mixture of 2 or more kinds of hydrocarbon-based organic solvents is defined by JIS K2601: the distillation test method described in 1998 measures mixtures of hydrocarbon-based organic solvents.
Examples of commercially available products of the hydrocarbon-based organic solvent having the initial boiling point outside the above range include: KYOWASOL C900 (initial boiling point: 132 ℃ C.) from KH Neochem corporation, EXOR D30 (initial boiling point: 145 ℃ C.) from ExxonMobil corporation, EXOR D110 (initial boiling point: 248 ℃ C.), EXOR D130 (initial boiling point: 279 ℃ C.), etc., but are not limited thereto.
The amount of the component (C) in the present invention is 5.5 to 28 parts by mass relative to 1.0 part by mass of the component (A). Among them, when the composition amount of the component (C) is less than 5.5% by mass, the storage property in an uncured state is deteriorated, which is not preferable. (C) When the component content exceeds 28 parts by mass, the wear resistance of the cured coating film of the cured product is deteriorated, which is not preferable. The amount of the component (C) is preferably 9.97 to 20 parts by mass based on 1.0 part by mass of the component (A). Within this range, excellent properties are obtained with respect to the storage property in an uncured state and the abrasion resistance of the cured coating film.
In addition, any additive component may be added to the curable composition of the present invention as appropriate within a range not impairing the properties thereof. For example, a reactive or non-reactive silicone oil, an adhesion imparting agent such as an alkoxysilane compound or a silane coupling agent, an antioxidant, a rust preventive, a coloring agent, a surfactant, a rheology modifier, an ultraviolet absorber, an infrared absorber, a fluorescent agent, a polishing agent, a perfume, a filler, and the like can be selected according to the purpose.
The method for forming a coating film of the curable composition of the present invention includes: the step of applying the curable composition (coating step), the step of drying the curable composition (drying step), and the step of wiping the coating film of the curable composition with a dry fiber or cloth (wiping off) (the step of wiping the coating film of the curable composition with a dry fiber or cloth) are not particularly limited. The solvent can be accelerated to be volatilized and removed by applying the curable composition, drying the composition to start the formation of a coating film, and wiping the coating film of the curable composition with a dry fiber or cloth. As a method of these steps, any appropriate application means such as mechanical coating and wiping using an automatic machine may be selected in addition to manual operation. Examples of the fiber or cloth used for coating and wiping include, but are not limited to, nonwoven fabrics and ultrafine fiber cloths.
In the coating film formation of the curable composition of the present invention, it is particularly preferable to have a step including a secondary wiping operation after the drying step. Examples thereof include: the curable composition is subjected to the following steps 1 to 5 in the order named.
Step 1: coating step
And a step 2: 1 st drying step
Step 3: the 1 st wiping step of the coating film of the curable composition with a dried fiber or cloth
And step 4: 2 nd drying step
Step 5: 2 nd wiping the coating film of the curable composition with the dried fiber or cloth
In a particularly preferred embodiment of the coating film forming method of the present invention, the coating film forming method comprises: coating the curable composition of the present invention to form a coating film 1 (step 1: coating step); drying the coating film 1 to obtain a dried coating film 2 (step 2: the 1 st drying step); wiping the dried coating film 2 with a dried fiber or cloth to obtain a coating film 3 (step 3: step of wiping the coating film of the curable composition with a dried fiber or cloth for the 1 st time); drying the coating film 3 to obtain a dried coating film 4 (step 4: 2 nd drying step); the dried coating film 4 is wiped with a dried fiber or cloth (step 5: step of wiping the coating film of the curable composition with the dried fiber or cloth 2 nd time).
In step 1, the curable composition of the present invention is applied to form a coating film 1. The coating method is not particularly limited, and may be performed by a method known to those skilled in the art. For example, a method of spreading a coating medium (for example, nonwoven fabric) impregnated with the curable composition of the present invention on a substrate can be employed. The amount of the curable composition to be applied is not particularly limited, and may be appropriately selected depending on the desired film thickness.
The substrate (target substrate) to which the curable composition of the present invention is applied is also not particularly limited, and for example, a metal steel sheet or a coated steel sheet can be suitably used. That is, the coating step (step 1) preferably includes a step of coating the curable composition on the surface of a metal steel sheet or a coated steel sheet. In addition, the present invention also provides: use of the curable composition of the present invention for forming a coating film on the surface of a metal steel sheet or a coated steel sheet; or a curable composition of the present invention for forming a coating film on the surface of a metal steel sheet or a coated steel sheet. The metal steel sheet or the coated steel sheet may be a steel sheet constituting a member, but is preferably a steel sheet constituting a member of a car body, a railway vehicle, heavy machinery, a ship, an airplane, agricultural machinery, or construction machinery. That is, in a preferred embodiment of the present invention, the metal steel sheet or the coated steel sheet is a part of any one of a vehicle body of an automobile, a railway vehicle, heavy machinery, a ship, an airplane, agricultural machinery, and construction machinery.
In step 2, the coating film 1 formed in step 1 is dried to obtain a dried coating film 2. The drying conditions with respect to the coating film 1 are not particularly limited, and the time of the step 2 is preferably 5 minutes or more and less than 6 hours in an atmosphere of, for example, 25 ℃ and 55% RH. The drying time varies depending on the working environment, and the present invention is not limited to the coating formation in an environment of 25 ℃ and 55% RH.
In step 3, the dried coating film 2 obtained in step 2 is wiped with a dry fiber or cloth to obtain a coating film 3. The fiber and the cloth are not particularly limited, and may be appropriately selected depending on the type of the base material, the film thickness of the dried coating film 2, and the like. Examples thereof include Microfiber, Microfiber cloth (Microfiber cloth), cotton, silk, and nonwoven fabric. The drying method of the fiber and cloth is not particularly limited as long as the organic solvent in the dried coating film 2 can be sufficiently removed. Specifically, the moisture content in the fiber and the cloth is 15 mass% or less, preferably 10 mass% or less, and more preferably 5 mass% or less (lower limit: 0 mass%) or so.
In step 4, the coating film 3 obtained in step 3 is dried to obtain a dried coating film 4. The drying conditions with respect to the coating film 1 are not particularly limited, but the time of the step 4 is preferably 5 minutes or more and less than 3 hours in an atmosphere of, for example, 25 ℃ and 55% RH. The drying time varies depending on the working environment, and the present invention is not limited to the coating formation in an environment of 25 ℃ and 55% RH. By performing the second wiping, the solvent unnecessary for film formation can be sufficiently removed, and a coating film free from spots can be formed.
In step 5, the dried coating film 4 obtained in step 4 is wiped with a dried fiber or cloth. The fiber and cloth used in step 5 are not particularly limited, and may be appropriately selected according to the type of the substrate, the film thickness of the dried coating film 4, and the like, and the same selection as in step 3 may be used. Similarly, the drying method of the fiber and the cloth is not particularly limited as long as the organic solvent in the dried coating film 4 can be sufficiently removed, and the conditions defined in the above step 3 can be similarly applied. The thickness (dry thickness) of the curable composition is not particularly limited, and is, for example, about 1 to 10000 nm.
[ use of curable composition ]
The curable composition of the present invention can be applied to various substrates such as metals, glasses, ceramics, and resins. Among these, the use of the steel sheet or the coated steel sheet in a metal plate or a coated steel sheet is preferable, and the use of the steel sheet or the coated steel sheet in a car body of an automobile, a railway vehicle, heavy machinery, a ship, an airplane, agricultural machinery, or construction machinery is particularly preferable, and the use of the steel sheet or the coated steel sheet in a car body of an automobile is more preferable.
Examples
The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, "%" and "part" mean "% by mass" and "part by mass", respectively. Unless otherwise specified, the operation was carried out at room temperature (25 ℃ C.).
Examples 1 to 7 and comparative examples 1 to 5
To prepare the curable composition, the following components were prepared.
(A) The components: silicone resin having hydrolyzable group
X-40-9250 (silicone resin containing methoxy and methyl groups, amount of alkoxy groups: 25% by mass, viscosity (25 ℃ C.): 80mm2(ii)/s, refractive index (25 ℃): 1.407, from shin & Yue chemical industry Co., Ltd.)
(B) The components: aluminum-based catalyst
DX-9740 (aluminum hydrolysis catalyst, product of shin-Etsu chemical Co., Ltd.)
(C) The components: hydrocarbon organic solvent having initial boiling point of 201-240 deg.C
EXOR D80 (initial boiling point 205 ℃, naphthenic, ExxonMobil Co., Ltd.)
SPCN-80 (initial boiling point 205 ℃, naphthene + paraffin series, manufactured by SPC Japan K.K.)
ISOPAR M (initial boiling point 225 ℃, isoparaffin series, product of ExxonMobil Co., Ltd.)
(C ') component (C'): hydrocarbon organic solvent having initial boiling point of 241 ℃ or higher
EXOR D110 (initial boiling point 248 ℃, naphthenic, ExxonMobil Co., Ltd.)
EXOR D130 (initial boiling point 279 ℃, naphthenic, ExxonMobil Co., Ltd.)
The curable compositions of examples and comparative examples were prepared by the following procedure using the above-described components. The above components were charged into a glass container at 25 ℃ and 55% RH to have the composition shown in Table 1, and stirred for 10 minutes by a Three-One Motor (New eastern science corporation).
The respective curable compositions thus obtained were evaluated for workability, water repellency, water-sliding property, abrasion resistance, and storage property. The evaluation items will be described below.
< workability >
Each of the curable compositions was sufficiently impregnated into a nonwoven fabric, and the surface of a black coated steel sheet (size: 7 cm. times.15 cm. times.1 mm) having a clear coat layer was thinly spread by hand, dried (left to stand) at 25 ℃ and 55% RH for 10 minutes, wiped with a dried ultrafine fiber cloth, further dried (left to stand) for 10 minutes, wiped again with a dried ultrafine fiber cloth, to prepare a test piece, wherein ○ represents a case where it was possible to confirm that the solvent completely disappeared during the application and the film could be formed without blocking or blurring, and x represents a case where the solvent remained, blocking or blurring occurred during the application, and the drying of the solvent was confirmed by the disappearance of the rainbow unevenness of the coating film of the curable composition, and the presence or absence of blocking and blurring was visually observed.
< Water repellency >
A test piece was prepared in the same manner as described in < workability >. The water repellency was evaluated by measuring the contact angle of water using a contact angle meter (DM-500, manufactured by Kyowa Kagaku Co., Ltd.) by dropping 5. mu.L of pure water on the surface of the test piece (black coated steel sheet). The water repellency was evaluated by the value of the contact angle.A contact angle of 90 ° or more was considered to be good water repellency.A contact angle of 90 ° or more was considered to be ○, and a contact angle of 80 ° or more and less than 90 ° was considered to be Δ. ○.
< Water slipping Property >
The test piece (black coated steel plate) was kept horizontal, 50 μ L of pure water was dropped on the surface thereof, the test piece was gradually tilted, and the slip angle, which is the angle at which the water droplets started to flow, was measured, and the value of the slip angle was evaluated as the water slip property (water slip property). if the slip angle is 30 ° or less, the water slip property was good, and therefore, the evaluation result showed that the slip angle was ○ when the slip angle was 30 ° or less, and Δ when the slip angle was larger than 30 ° and 40 ° or less, ○ indicated that the water slip property was good.
< abrasion resistance >
The test piece (black coated steel plate) was coated with 100ml of pure water, and the test piece (black coated steel plate) was set on a simple friction tester (product of wayof kokusho corporation) so that the axis of the cylinder was oriented in a direction perpendicular to the direction in which the friction material moved thereon, and the test piece was rubbed 500 times with the rubbing action being applied, so that the contact area between the surface of the black coated steel plate and the friction material was about 4cm × 2cm, the load was 500g, and the test piece (black coated steel plate) was wiped with water vapor, dried, and water repellency was confirmed to be 90 ° or more, and water repellency was set to be equal to or less than 90 ° and water repellency was equal to or more than 30 ° and equal to or less than 90 ° and water repellency was equal to or less than 30 ° and equal to or less than 90 ° and water repellency (water repellency).
< storage Property >
The test piece was placed in a 200ml glass container and stored for 7 days in an environment of 25 ℃ x 55% RH, a case where no white turbidity occurred during storage and film formation could be performed without causing caking or blurring during construction by the same method as the above-described workability evaluation method was ○, a case where no white turbidity occurred but only a part (to the extent of less than 1% of the whole) was caused to cake or blur during construction was Δ, a case where no white turbidity occurred but caking or blurring occurred in 1% or more of the whole during construction and white turbidity occurred and caking or blurring occurred due to white turbidity was evident even during construction was x, and the construction method used the method described in the above-described workability evaluation methods ○ and Δ indicated that the storability was acceptable, ○ indicated that the storability was good, and x indicated that the storability was poor (could not be tolerated).
Examples 1 to 4 and 6 to 7 each obtained good results in all evaluation items of water repellency, abrasion resistance, workability and storability by adding 9.970 to 20.000 parts by mass of a hydrocarbon-based organic solvent having a primary boiling point of 201 to 240 ℃ to 1.0 part by mass of the component (A). In example 5, 7 parts by mass of EXOR D80 having a primary boiling point of 205 ℃ and 3 parts by mass of EXOR D110 having a primary boiling point of 248 ℃ were added to 1.0 part by mass of the component (A), and the primary boiling point was 215 ℃ for the entire hydrocarbon-based organic solvent mixture, so that good results were obtained in all the evaluation items.
On the other hand, in comparative examples 1 to 2, 30 to 40 parts by mass of a hydrocarbon-based organic solvent having a primary boiling point of 201 to 240 ℃ was added to 1.0 part by mass of the component (A), and the abrasion resistance was poor. The reason for this is considered to be that when the amount of the organic solvent is large, the concentration of the component (a) in the system becomes low, and a thin film is formed during the formation of the coating film, and therefore, sufficient abrasion resistance is not provided. In comparative example 5, 5 parts by mass of a hydrocarbon-based organic solvent having an initial boiling point of 205 ℃ was added alone, but the storage stability was poor. The reason for this is that when the concentration of the component (a) in the system is too high, the reaction tends to be linked to occur during a partial moisture curing reaction during storage. In comparative example 3, 9.97 parts by mass of a hydrocarbon-based organic solvent having an initial boiling point of 248 ℃ was added to 1.0 part by mass of component (A), but the abrasion resistance, workability and storage property were poor. The reason for this is that the initial boiling point is high, so that the volatility of the solvent is poor, and the solvent cannot be sufficiently wiped off by only 2 wiping operations, so that the workability is poor, and defects are generated in the formed coating film. In comparative example 4, 9.97 parts by mass of a hydrocarbon-based organic solvent having an initial boiling point of 279 ℃ was added to 1.0 part by mass of component (A), but the abrasion resistance and workability were poor. The reason for this is considered to be that since the initial boiling point is high, the volatility of the solvent is poor, and the solvent cannot be sufficiently wiped off only by 2 wiping operations, so that the workability is poor, and defects are generated in the formed coating film.
As described above, the curable composition of the present invention has excellent properties such as water repellency, water-slipping property, abrasion resistance, storage property, and workability. The curable composition of the present invention is preferably used for forming a coating film for imparting various properties to a metal steel sheet or a coated steel sheet, particularly for automobiles, and is useful.
Claims (7)
1. A curable composition comprising:
(A) 1.0 part by mass of a silicone resin having a hydrolyzable group
(B) 0.05 to 5.0 parts by mass of an aluminum catalyst
(C) 5.5 to 28 parts by mass of a hydrocarbon organic solvent having an initial boiling point of 201 to 240 ℃.
2. The curable composition according to claim 1, wherein the amount of the component (B) is 0.095 to 0.19 parts by mass relative to 1.0 part by mass of the component (A).
3. The curable composition according to claim 1 or 2, wherein the amount of the component (C) is 9.97 to 20 parts by mass based on 1.0 part by mass of the component (A).
4. A method for forming a coating film, comprising the steps 1 to 5 in this order using the curable composition according to any one of claims 1 to 3,
step 1: coating step
And a step 2: 1 st drying step
Step 3: 1 st wiping the coating film of the curable composition with the dried fiber or cloth
And step 4: 2 nd drying step
Step 5: and (2) wiping the coating film of the curable composition with the dried fiber or cloth.
5. The method according to claim 4, wherein the coating step comprises a step of coating the curable composition on the surface of a metal steel sheet or a coated steel sheet.
6. Use of the curable composition according to any one of claims 1 to 3 for forming a coating film on the surface of a metal steel sheet or a coated steel sheet.
7. The use of the curable composition according to claim 6, wherein the metal steel sheet or the coated steel sheet is part of an automobile body, a railway vehicle, heavy equipment, a ship, an airplane, agricultural equipment, or construction equipment.
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| CN1844250A (en) * | 2005-04-08 | 2006-10-11 | 信越化学工业株式会社 | Curable resin composition for sealing LED elements |
| CN102333832A (en) * | 2009-02-28 | 2012-01-25 | 神户合成株式会社 | Surface-protective water-repellent agent for exterior surfaces |
| TW201807114A (en) * | 2016-04-26 | 2018-03-01 | 三鍵股份有限公司 | A curable composition |
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| JP2004204131A (en) * | 2002-12-26 | 2004-07-22 | Kao Corp | Water repellent coating agent composition |
| JP4106063B2 (en) * | 2004-06-30 | 2008-06-25 | 株式会社ソフト９９コーポレーション | Surface protective agent for outdoor painted surfaces |
| JP2008169360A (en) * | 2007-01-15 | 2008-07-24 | Nicca Chemical Co Ltd | Wiping-up type brightener and method for imparting gloss to surface of article |
| JP5697897B2 (en) * | 2010-05-31 | 2015-04-08 | 神戸合成株式会社 | Surface water-repellent protective agent for exterior surfaces |
| JP5682095B2 (en) * | 2011-05-18 | 2015-03-11 | スリーボンドファインケミカル株式会社 | Coating layer and coating layer forming method |
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|---|---|---|---|---|
| CN1844250A (en) * | 2005-04-08 | 2006-10-11 | 信越化学工业株式会社 | Curable resin composition for sealing LED elements |
| CN102333832A (en) * | 2009-02-28 | 2012-01-25 | 神户合成株式会社 | Surface-protective water-repellent agent for exterior surfaces |
| TW201807114A (en) * | 2016-04-26 | 2018-03-01 | 三鍵股份有限公司 | A curable composition |
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