CN114437664A - Temperature-resistant oil-resistant acetone-removing type organosilicon sealant and preparation method and application thereof - Google Patents
Temperature-resistant oil-resistant acetone-removing type organosilicon sealant and preparation method and application thereof Download PDFInfo
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- 239000000565 sealant Substances 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- -1 polydimethylsiloxane Polymers 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 238000003860 storage Methods 0.000 claims abstract description 16
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims abstract description 14
- 229920002050 silicone resin Polymers 0.000 claims abstract description 14
- 239000000945 filler Substances 0.000 claims abstract description 13
- 239000003381 stabilizer Substances 0.000 claims abstract description 11
- 239000004205 dimethyl polysiloxane Substances 0.000 claims abstract description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims abstract description 9
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 8
- 239000007822 coupling agent Substances 0.000 claims abstract description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- 238000011065 in-situ storage Methods 0.000 claims abstract description 3
- 239000003921 oil Substances 0.000 claims description 44
- 239000004590 silicone sealant Substances 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 11
- UOURRHZRLGCVDA-UHFFFAOYSA-D pentazinc;dicarbonate;hexahydroxide Chemical group [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[Zn+2].[O-]C([O-])=O.[O-]C([O-])=O UOURRHZRLGCVDA-UHFFFAOYSA-D 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910021485 fumed silica Inorganic materials 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- JXUAUKKYXQMOHO-UHFFFAOYSA-N tris(2,2,2-trifluoroethoxy)silane Chemical compound FC(F)(F)CO[SiH](OCC(F)(F)F)OCC(F)(F)F JXUAUKKYXQMOHO-UHFFFAOYSA-N 0.000 claims description 6
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 claims description 5
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 239000004408 titanium dioxide Substances 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000002444 silanisation Methods 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 3
- 229940007718 zinc hydroxide Drugs 0.000 claims description 3
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 2
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 claims description 2
- FMGBDYLOANULLW-UHFFFAOYSA-N 3-isocyanatopropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCN=C=O FMGBDYLOANULLW-UHFFFAOYSA-N 0.000 claims description 2
- KVUMYOWDFZAGPN-UHFFFAOYSA-N 3-trimethoxysilylpropanenitrile Chemical compound CO[Si](OC)(OC)CCC#N KVUMYOWDFZAGPN-UHFFFAOYSA-N 0.000 claims description 2
- 229910008051 Si-OH Chemical group 0.000 claims description 2
- 229910006358 Si—OH Chemical group 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- GBFVZTUQONJGSL-UHFFFAOYSA-N ethenyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](OC(C)=C)(OC(C)=C)C=C GBFVZTUQONJGSL-UHFFFAOYSA-N 0.000 claims description 2
- QQFBQBDINHJDMN-UHFFFAOYSA-N ethyl 2-trimethylsilylacetate Chemical compound CCOC(=O)C[Si](C)(C)C QQFBQBDINHJDMN-UHFFFAOYSA-N 0.000 claims description 2
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 2
- ZWXYOPPJTRVTST-UHFFFAOYSA-N methyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](C)(OC(C)=C)OC(C)=C ZWXYOPPJTRVTST-UHFFFAOYSA-N 0.000 claims description 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims description 2
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 2
- XGIZTLFJCDBRDD-UHFFFAOYSA-N phenyl-tris(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](OC(C)=C)(OC(C)=C)C1=CC=CC=C1 XGIZTLFJCDBRDD-UHFFFAOYSA-N 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 238000012360 testing method Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical class OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000004073 vulcanization Methods 0.000 description 5
- 230000032683 aging Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000010705 motor oil Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- XPFOWMOZUAQIJW-UHFFFAOYSA-N CC(CC(NC(=N)N)(C)C)([Si](OC)(OC)OC)C Chemical compound CC(CC(NC(=N)N)(C)C)([Si](OC)(OC)OC)C XPFOWMOZUAQIJW-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000004944 Liquid Silicone Rubber Substances 0.000 description 1
- VDRSDNINOSAWIV-UHFFFAOYSA-N [F].[Si] Chemical compound [F].[Si] VDRSDNINOSAWIV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229920002631 room-temperature vulcanizate silicone Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000001039 zinc pigment 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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Sealing Material Composition (AREA)
Abstract
The invention provides a temperature-resistant oil-resistant acetone-removing type organosilicon sealant and a preparation method and application thereof, relating to the technical field of organosilicon sealants. The acetone-removing type organosilicon sealant is prepared from the following raw materials in parts by weight: 50-70 parts of alpha, omega-dihydroxy polydimethylsiloxane, 30-50 parts of alpha, omega-dihydroxy polymethyl (3,3, 3-trifluoropropyl) siloxane, 3-10 parts of silicone resin, 100-200 parts of filler, 5-15 parts of cross-linking agent, 2-10 parts of coupling agent, 0.5-5 parts of catalyst, 3-10 parts of heat-resistant agent, 0.5-5 parts of structural control agent and 0.5-5 parts of storage stabilizer; the catalyst is a silanized full carboxylic acid derivative. The acetone-removing type organosilicon sealant has excellent high-temperature resistance and oil resistance, and is suitable for being used as a gasket formed in situ.
Description
Technical Field
The invention relates to the technical field of organosilicon sealants, in particular to a temperature-resistant oil-resistant acetone-free organosilicon sealant and a preparation method and application thereof.
Background
Form-in-place gaskets (or form-in-place gaskets) are commonly used in automotive transmission systems, for example, to seal engine oil pans, rockers, timing chain covers, oil filter covers, bearing caps, valve covers, coolant systems, and the like, which have high sealing performance requirements, to prevent air or liquid leakage. The form-in-place gasket is typically made of silicone rubber, and in operation, liquid silicone rubber is applied to the flange face to form the gasket during assembly. Silicone sealants have excellent high and low temperature resistance, as well as good chemical resistance and high displacement capability, and are widely used as sealing materials for oil pan connectors, chain covers, and transmission fittings.
Currently available silicone sealants mainly include the following types: dealcoholized, ketoxime-removed, acetone-removed and amide-removed forms. The dealcoholized sealant is difficult to adapt to the production and assembly requirements due to low activity and low vulcanization speed of a cross-linking agent, and a viscosity peak exists in the production process, so that some fillers and additives which need to be added in the later period are difficult to add, thereby influencing the performance of the sealant. The deacylated ammonia type sealant belongs to a low modulus sealant, has high elongation and low strength, is mainly used for building joints and places with large expansion displacement, and is not suitable for being used as a sealant for temperature-resistant and oil-resistant purposes. The ketoxime removing type sealant can also be used for manufacturing a gasket formed in situ, but has the defects of large smell, low vulcanization speed, poor oil resistance and the like. The de-acetone sealant has the characteristics of no toxicity, high vulcanization speed, good adhesion to a contact substrate and no pollution, and the heat resistance of the de-acetone sealant is a better one of various condensed type RTV silicone rubbers, and is suitable for being used as a gasket sealant formed in place.
Silicone sealants used to make in-place gaskets need to have good high temperature resistance, oil resistance, and a relatively fast cure rate to meet production assembly requirements. Most of the high-temperature-resistant and oil-resistant sealants manufactured on the market use alpha, omega-dihydroxy polydimethylsiloxane as a base polymer, although the high-temperature-resistant sealants have good high-temperature resistance, the oil-resistant effect is not good enough, and the mechanical property of the sealant is reduced and the storage stability is poor after a large amount of oil-resistant fillers are added. In addition, in the acetone-removing type single-component sealant, tetramethyl guanidinopropyltrimethoxysilane is used as a catalyst in many products, so that the prepared sulfide product is easy to turn yellow when being irradiated by heat fire ultraviolet light and is not vulcanized in an acid environment.
Therefore, it is necessary to develop a silicone sealant with high temperature resistance, oil resistance and high vulcanization speed to meet the demand of forming gaskets on site.
Disclosure of Invention
In view of the above, it is necessary to provide a heat-resistant oil-resistant acetone-free silicone sealant having excellent heat-resistant and oil-resistant properties.
A temperature-resistant oil-resistant acetone-removing type organosilicon sealant is prepared from the following raw materials in parts by weight:
the structural formula of the alpha, omega-dihydroxy polydimethylsiloxane is as shown in the formula I:
in the formula I, n is selected from 150-2000, and the viscosity at 25 ℃ is 2000-50000 MPa.s;
the structural formula of the alpha, omega-dihydroxy polymethyl (3,3, 3-trifluoropropyl) siloxane is shown as a formula II:
in the formula II, n is selected from 100-3000, and the viscosity at 25 ℃ is 2000-20000 MPa.s;
the catalyst is a silanized full carboxylic acid derivative.
In the organosilicon sealant, the alpha, omega-dihydroxy polymethyl (3,3, 3-trifluoropropyl) siloxane contains fluorine groups, so that a polysiloxane polymer is endowed with lower surface energy, and the oil-proof performance of the sealant is improved; the alpha, omega-dihydroxy polymethyl (3,3, 3-trifluoropropyl) siloxane and the alpha, omega-dihydroxy polydimethylsiloxane are matched for use, the silicone resin and the filler are added, the high temperature resistance, the oil resistance and the mechanical property of the sealant are improved, and the structured control agent and the storage stabilizer are added to prolong the shelf life of the sealant; furthermore, the silanized perfluorocarboxylic acid derivative is used as a catalyst, so that the problem that the sulfide is not vulcanized under the conditions of heat, ultraviolet light or acidity can be avoided.
In the present invention, the amount of α, ω -dihydroxypolymethyl (3,3, 3-trifluoropropyl) siloxane used may have an effect on the oil resistance of the silicone sealant. If the addition amount is too low, the oil resistance of the sealant is poor; if the amount is too high, the adhesiveness of the sealant is poor.
In one embodiment, the raw materials further comprise 1-10 parts of pigment.
In one embodiment, the pigment is selected from: titanium dioxide and carbon black.
In one embodiment, the silicone resin is MQ silicone resin containing vinyl and Si-OH groups, such as VR-15 and VR-20 of Shandong Yue silicone material GmbH, and SH-5202P of Shenzhen Shenpeng silicon fluorine material GmbH. The MQ silicon resin can improve the oil resistance and oil-resistant adhesion of the sealant and simultaneously improve the mechanical property of the sealant.
In one embodiment, the filler is a composition of basic zinc carbonate and fumed silica, and the mass ratio of the basic zinc carbonate to the fumed silica is (90-180): (10-20), wherein the basic zinc carbonate contains 10-30 wt% of zinc hydroxide. Preferably, the mass ratio of the basic zinc carbonate to the fumed silica is (90-175): (10-15).
By adopting the composition, the sealant can keep good oil resistance and mechanical strength, and has good storage stability and construction performance.
In one embodiment, the cross-linking agent is selected from: at least one of methyl triisopropenoxysilane, vinyl triisopropenoxysilane, and phenyl triisopropenoxysilane.
In one embodiment, the coupling agent is selected from: 3-aminopropyltriethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, and 3-aminopropylmethyldiethoxysilane.
In one embodiment, the heat resistant agent is selected from: at least one of gas phase titanium dioxide, iron oxide and cerium oxide.
In one embodiment, the structured control agent is selected from: at least one of gamma-cyanopropyltrimethoxysilane and beta-cyanoethyltrimethoxysilane.
In one embodiment, the storage stabilizer is selected from: at least one of hexamethyldisilazane, ethyl trimethylsilylacetate and 3-isocyanatopropyl trimethoxysilane.
In one embodiment, the catalyst has a structural formula as shown in formula III.
The catalyst is the self-made silanized perfluorocarboxylic acid derivative, and compared with the conventionally used 1,1,3, 3-tetramethyl guanidine propyl trimethoxy silane catalyst, the catalyst for preparing the acetone-removing sealant eliminates the problems that sulfide becomes yellow under heat or ultraviolet irradiation and is not vulcanized under acidic conditions.
In one embodiment, the preparation method of the silanized full carboxylic acid derivative is shown as the formula IV:
s1, mixing N, O-bis (trimethylsilyl acetamide) and allyl perfluorocarboxylic acid, and carrying out a silanization reaction;
s2, adding tris (2,2, 2-trifluoroethoxy) silane (chemical formula (CF)3CH2O)3SiH) to carry out a hydrosilylation reaction to obtain a silylated all-carboxylic acid derivative.
In one embodiment, S1 specifically is: n, O-bis (trimethylsilyl acetamide), toluene and allyl perfluorocarboxylic acid are mixed according to a mass ratio of 1: (2.4-3.4): (3.8-4.8), stirring and reacting for 1.5-2.5 h at 40-50 ℃, distilling, and collecting the solution at 97-99 ℃.
In one embodiment, S2 specifically is: adding tris (2,2, 2-trifluoroethoxy) silane into the solution obtained from S1 at the temperature of 70-100 ℃, wherein the mass ratio of the tris (2,2, 2-trifluoroethoxy) silane to the solution is 1: (0.5-0.9), reacting for 0.5-1.5 h, and distilling under reduced pressure to remove the solvent to obtain the silanized perfluorocarboxylic acid derivative.
In one embodiment, the silicone resin is 3-8 parts, the filler is 100-150 parts, the crosslinking agent is 5-10 parts, the coupling agent is 2-5 parts, the catalyst is 0.5-3 parts, the heat-resistant agent is 3-8 parts, the structural control agent is 0.5-3 parts, and the storage stabilizer is 0.5-3 parts.
The invention also provides a preparation method of the temperature-resistant oil-resistant organosilicon sealant, which comprises the following steps:
s1, uniformly blending alpha, omega-dihydroxy polydimethylsiloxane, alpha, omega-dihydroxy polymethyl (3,3, 3-trifluoropropyl) siloxane and part of filler, and heating and dehydrating until the moisture content is below 500 ppm;
s2, adding the silicone resin, the heat-resistant agent and the rest of the filler, and uniformly mixing;
s3, adding a structural control agent, a storage stabilizer and a cross-linking agent, uniformly mixing, and adding a coupling agent;
and S4, adding a catalyst, and uniformly mixing to obtain the temperature-resistant oil-resistant acetone-removing type organosilicon sealant.
The preparation method is simple, easy to operate and suitable for industrial production.
In one embodiment, the filler is a combination of basic zinc carbonate and fumed silica, the basic zinc carbonate being added at S1 and the fumed silica being added at S2.
In one embodiment, in the step S1, the heating temperature is 95-115 ℃, the vacuum degree is 0.085-0.1 MPa, the stirring speed is 200-500 rpm, and the heating dehydration time is 120-240 min.
In one embodiment, in the step S2, the stirring speed is 200-500 rpm, the time is 20-50 min, the vacuum degree is 0.085-0.1 MPa, and the temperature is 25-50 ℃.
In one embodiment, in the step S3, the stirring speed is 200-500 rpm, the time is 20-50 min, the vacuum degree is 0.085-0.1 MPa, and the temperature is 25-50 ℃.
In one embodiment, in the step S4, the stirring speed is 200-500 rpm, the time is 20-50 min, the vacuum degree is 0.085-0.1 MPa, and the temperature is 25-50 ℃.
The invention also provides application of the temperature-resistant oil-resistant acetone-removing type organosilicon sealant in preparation of an in-place forming gasket.
Compared with the prior art, the invention has the following beneficial effects:
in the organosilicon sealant, the alpha, omega-dihydroxy polymethyl (3,3, 3-trifluoropropyl) siloxane contains fluorine groups, so that a polysiloxane polymer has lower surface energy and is beneficial to improving the oil-proof performance of the sealant; the alpha, omega-dihydroxy polymethyl (3,3, 3-trifluoropropyl) siloxane and the alpha, omega-dihydroxy polydimethylsiloxane are matched for use, the silicone resin and the filler are added, the high temperature resistance, the oil resistance and the mechanical performance of the sealant are improved, and meanwhile, the structural control agent and the storage stabilizer are added, so that the shelf life of the sealant is prolonged; furthermore, the silanized perfluorocarboxylic acid derivative is used as a catalyst, so that the problem that the sulfide is not vulcanized under the conditions of heat, ultraviolet light or acidity can be avoided. The organosilicon sealant disclosed by the invention has excellent high-temperature resistance and oil resistance, can keep good tensile strength, elongation at break and oil-resistant adhesion, and is particularly suitable for manufacturing a formed-in-place gasket.
Detailed Description
To facilitate an understanding of the invention, the invention will now be described more fully with reference to the preferred embodiments. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
The starting materials in the following examples and comparative examples were all commercially available unless otherwise specified. The MQ silicone resin is VR-20MQ silicone resin of Shandong Yue organic materials GmbH. The zinc hydroxide content of the basic zinc carbonate was 20 wt%.
Example 1
The raw materials and the dosage of the organosilicon sealant are shown in Table 1.
In this example, the viscosity of α, ω -dihydroxypolydimethylsiloxane at 25 ℃ was 20000 mPas, and the viscosity of α, ω -dihydroxypolymethylsiloxane (3,3, 3-trifluoropropyl) at 25 ℃ was 10000 mPas.
The preparation method of the catalyst silanization perfluorocarboxylic acid derivative comprises the following steps: (1) adding N, O-bis (trimethylsilyl acetamide), toluene and allyl perfluorocarboxylic acid into a flask, wherein the mass ratio of the N, O-bis (trimethylsilyl acetamide), the toluene and the allyl perfluorocarboxylic acid is 1: 2.9: 4.3, stirring and reacting for 2 hours at the temperature of about 48 ℃; distilling and collecting the solution at the temperature of 95-99 ℃. (2) Heating and stirring the solution collected in the step (1) at 70-100 ℃, adding tris (2,2, 2-trifluoroethoxy) silane for reacting for 1h, wherein the mass ratio of the collected solution to the tris (2,2, 2-trifluoroethoxy) silane is 1: 0.7, after the reaction is finished, evaporating and removing volatile matters at the temperature of 80 ℃ in a reduced pressure environment to obtain the silanized perfluorocarboxylic acid derivative. The reaction process is shown as IV. The catalyst silanized perfluorocarboxylic acid derivatives used in other examples or comparative examples were prepared by this method.
The silicone sealant of this example was prepared by the following method:
(1) adding alpha, omega-dihydroxy polydimethylsiloxane, alpha, omega-dihydroxy polymethyl (3,3, 3-trifluoropropyl) siloxane, basic zinc carbonate and pigment into a kneader, heating, dehydrating and kneading for 150min under the conditions of 110 ℃, 350rpm and 0.09MPa of vacuum degree, and cooling to obtain the base material when the moisture content is reduced to below 500 ppm.
(2) Sequentially adding MQ silicon resin, fumed silica and heat-resistant agent into a power mixer filled with the base material step by step, stirring at 350rpm for 50min, and controlling the temperature below 45 ℃.
(3) And sequentially adding the structural control agent, the storage stabilizer and the crosslinking agent into the power mixer, stirring at 350rpm for 20min, adding the coupling agent, stirring at 350rpm for 20min, and controlling the temperature to be below 45 ℃.
(4) Adding catalyst, stirring at 350rpm for 30min, controlling temperature below 45 deg.C, and mixing.
Example 2
The raw materials and the dosage of the organosilicon sealant are shown in the table 1.
In this example, the viscosity of α, ω -dihydroxypolydimethylsiloxane was 10000 mPas at 25 ℃ and the viscosity of α, ω -dihydroxypolymethylsiloxane (3,3, 3-trifluoropropyl) was 2000 mPas at 25 ℃.
The silicone sealant of this example was prepared in substantially the same manner as in example 1, except that the raw material components and amounts were replaced as shown in Table 1.
Example 3
The raw materials and the dosage of the organosilicon sealant are shown in Table 1.
In this example, the viscosity of α, ω -dihydroxypolydimethylsiloxane was 10000 mPas at 25 ℃ and the viscosity of α, ω -dihydroxypolymethylsiloxane (3,3, 3-trifluoropropyl) was 2000 mPas at 25 ℃.
The silicone sealant of this example was prepared in substantially the same manner as in example 1, except that the raw material components and amounts were replaced as shown in Table 1.
Example 4
The raw materials and the dosage of the organosilicon sealant are shown in Table 1.
In this example, the viscosity of α, ω -dihydroxypolydimethylsiloxane at 25 ℃ was 50000 mPas, and the viscosity of α, ω -dihydroxypolymethyl (3,3, 3-trifluoropropyl) siloxane at 25 ℃ was 2000 mPas.
The silicone sealant of this example was prepared in substantially the same manner as in example 1, except that the raw material components and amounts were replaced as shown in Table 1.
TABLE 1 examples Silicone sealants raw material types and amounts (by weight)
Comparative example 1
A silicone sealant was prepared in substantially the same manner as in example 1 except that α, ω -dihydroxypolydimethylsiloxane and MQ silicone resin were not added and that α, ω -dihydroxypolymethylsiloxane (3,3, 3-trifluoropropyl) was used in an amount of 100 parts.
Comparative example 2
An organosilicon sealant, the raw materials and preparation method of which are basically the same as those of example 1, is characterized in that no structural control agent and no storage stabilizer are added.
Comparative example 3
A silicone sealant substantially the same as in example 1 except that the silanized perfluorocarboxylic acid derivative was replaced with an equal amount of tetramethylguanidinopropyltrimethoxysilane.
Comparative example 4
A silicone sealant was prepared in substantially the same manner as in example 1 except that no heat-resistant agent was added.
Comparative example 5
A silicone sealant was prepared in substantially the same manner as in example 1 except that α, ω -dihydroxypolymethyl (3,3, 3-trifluoropropyl) siloxane was not added and α, ω -dihydroxypolydimethylsiloxane was used in an amount of 100 parts.
Experimental example 1
The silicone sealants of the above examples and comparative examples were tested for high temperature and oil resistance. Making a tensile test piece according to GB/T528; manufacturing a shear strength test piece (the material for preparing the piece is anodized aluminum) according to GB/T7124; according to GB/T13477.2-2002 part 4 of test method of building sealing materials: the extrudability of the sealant prepared by the test of the original packaged single-component sealing material extrudability is tested according to GB/T13477.10-2002 part 8 of the test method of the building sealing material: measurement of tensile adhesion the adhesion of the sealant was measured by method A in method A.
The storage period test is to place the product in a thermostat at 70 ℃ for 5 days to accelerate aging and test the product performance.
The test condition of the temperature resistance and the oil resistance is that the performance is tested after the automobile engine oil is soaked in 5W-30W of 150 ℃ for 250 h.
The normal test condition is that the test piece is vulcanized for 7 days at the temperature of 25 ℃ and the humidity of 50 percent RH for testing performance, and the temperature resistance and oil resistance test condition is that after the vulcanization is carried out for 7 days under the normal condition, the test piece is continuously soaked in the automobile engine oil 5W-30 at the temperature of 150 ℃ for 250 hours and then is placed under the normal condition for 24 hours for testing performance.
The test results are shown in table 2.
Table 2 results of performance testing
The test results show that the organosilicon sealants of examples 1-4 show good temperature and oil resistance after temperature and oil resistance tests, show good storage stability after accelerated aging at 70 ℃ for 5d, have tensile strength retention rate of over 80 percent, little change in elongation at break, tensile strength retention rate of over 70 percent and good comprehensive performance after temperature and oil resistance tests.
Comparative example 1, in which no α, ω -dihydroxypolydimethylsiloxane and no MQ silicone resin containing vinyl groups and Si — OH groups were added, had poor temperature resistance and oil resistance and poor adhesion as compared with example 1. Comparative example 2, in which no structuring control agent and no storage stabilizer were added, had poor extrudability, a structuring phenomenon and poor storage stability after accelerated aging at 70 ℃ for 5 days, compared to example 1. Comparative example 3 instead of using the silylated perfluorocarboxylic acid derivative of the present invention as a catalyst, 1,3, 3-tetramethylguanidinopropyltrimethoxysilane catalyst was used, and the product exhibited yellowing of the sulfide under a heated environment, as compared to example 1. Comparative example 4, in which no heat-resistant agent was added, showed a greater performance decay in both the 70 ℃ x 5d accelerated aging test and the temperature and temperature resistance test than in example 1. Comparative example 5, in which no α, ω -dihydroxypolymethyl (3,3, 3-trifluoropropyl) siloxane was used, had inferior temperature resistance and oil resistance and large strength decay compared to example 1.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (10)
1. The temperature-resistant oil-resistant acetone-removing type organosilicon sealant is characterized by being prepared from the following raw materials in parts by weight:
the structural formula of the alpha, omega-dihydroxy polydimethylsiloxane is as shown in the formula I:
in the formula I, n is selected from 150-2000, and the viscosity at 25 ℃ is 2000-50000 MPa & s;
the structural formula of the alpha, omega-dihydroxy polymethyl (3,3, 3-trifluoropropyl) siloxane is shown as a formula II:
in the formula II, n is selected from 100-3000, and the viscosity at 25 ℃ is 2000-20000 MPa.s;
the catalyst is a silanized full carboxylic acid derivative.
2. The temperature-resistant oil-resistant de-acetone type organic silicon sealant as claimed in claim 1, wherein the raw materials further comprise 1-10 parts of pigments, and the pigments are selected from: titanium dioxide and carbon black.
3. The temperature-resistant, oil-resistant, de-acetonic silicone sealant of claim 1, wherein the silicone resin is a vinyl and Si-OH group containing MQ silicone resin; the filler is a composition of basic zinc carbonate and fumed silica, and the mass ratio of the basic zinc carbonate to the fumed silica is (90-180): (10-20), wherein the basic zinc carbonate contains 10-30 wt% of zinc hydroxide.
4. The temperature and oil resistant, de-acetonized silicone sealant of claim 1 wherein the cross-linking agent is selected from the group consisting of: at least one of methyl triisopropenoxysilane, vinyl triisopropenoxysilane, and phenyl triisopropenoxysilane; the coupling agent is selected from: 3-aminopropyltriethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, and 3-aminopropylmethyldiethoxysilane.
5. The temperature and oil resistant de-acetonized silicone sealant of claim 1, wherein the heat resistant agent is selected from the group consisting of: at least one of gas phase titanium dioxide, iron oxide and cerium oxide; the structural control agent is selected from: at least one of gamma-cyanopropyltrimethoxysilane and beta-cyanoethyltrimethoxysilane; the storage stabilizer is selected from: at least one of hexamethyldisilazane, ethyl trimethylsilylacetate and 3-isocyanatopropyl trimethoxysilane.
6. The temperature-resistant oil-resistant de-acetonized organosilicon sealant according to any one of claims 1 to 5, wherein the structural formula of the catalyst is shown as formula III.
7. The temperature-resistant oil-resistant de-acetonized organosilicon sealant according to claim 6, wherein the preparation method of the silylated all-carboxylic acid derivative is shown as formula IV:
s1, mixing N, O-bis (trimethylsilyl acetamide) and allyl perfluorocarboxylic acid, and carrying out a silanization reaction;
s2, adding tris (2,2, 2-trifluoroethoxy) silane, and carrying out hydrosilylation reaction to obtain the silanized full carboxylic acid derivative.
8. A preparation method of the temperature-resistant oil-resistant acetone-free type organosilicon sealant as claimed in any one of claims 1 to 7, which is characterized by comprising the following steps:
s1, uniformly blending alpha, omega-dihydroxy polydimethylsiloxane, alpha, omega-dihydroxy polymethyl (3,3, 3-trifluoropropyl) siloxane and part of filler, and heating and dehydrating until the moisture content is below 500 ppm;
s2, adding the silicone resin, the heat-resistant agent and the rest of the filler, and uniformly mixing;
s3, adding a structural control agent, a storage stabilizer and a cross-linking agent, uniformly mixing, and adding a coupling agent;
and S4, adding a catalyst, and uniformly mixing to obtain the temperature-resistant oil-resistant acetone-removing type organosilicon sealant.
9. The preparation method according to claim 8, wherein in the S1, the heating temperature is 95-115 ℃, the vacuum degree is 0.085-0.1 MPa, the stirring rotation speed is 200-500 rpm, and the heating dehydration time is 120-240 min;
in the S2, the stirring speed is 200-500 rpm, the time is 20-50 min, the vacuum degree is 0.085-0.1 MPa, and the temperature is 25-50 ℃;
in the S3, the stirring speed is 200-500 rpm, the time is 20-50 min, the vacuum degree is 0.085-0.1 MPa, and the temperature is 25-50 ℃;
in the S4, the stirring speed is 200-500 rpm, the time is 20-50 min, the vacuum degree is 0.085-0.1 MPa, and the temperature is 25-50 ℃.
10. The use of the temperature resistant, oil resistant, de-acetonized silicone sealant of any of claims 1-7 in the preparation of in-situ formed gaskets.
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| CN114989780A (en) * | 2022-07-18 | 2022-09-02 | 广东高士高科实业有限公司 | Oil-resistant silicone sealant and preparation method and application thereof |
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Denomination of invention: Temperature and oil resistant deacetone type organic silicone sealant and its preparation method and application Effective date of registration: 20231205 Granted publication date: 20221216 Pledgee: Guangdong Huaiji Rural Commercial Bank Co.,Ltd. Pledgor: Guangdong Gao Shi Gao Ke Industrial Co.,Ltd. Registration number: Y2023980069333 |