CN113773499A - Functional silane macromolecular polymer, preparation method, additive and application - Google Patents
Functional silane macromolecular polymer, preparation method, additive and application Download PDFInfo
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- CN113773499A CN113773499A CN202111147735.3A CN202111147735A CN113773499A CN 113773499 A CN113773499 A CN 113773499A CN 202111147735 A CN202111147735 A CN 202111147735A CN 113773499 A CN113773499 A CN 113773499A
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- silane
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 229920000642 polymer Polymers 0.000 title claims abstract description 48
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 48
- 239000000654 additive Substances 0.000 title claims abstract description 23
- 230000000996 additive effect Effects 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 238000000576 coating method Methods 0.000 claims abstract description 52
- 239000011248 coating agent Substances 0.000 claims abstract description 51
- 239000002904 solvent Substances 0.000 claims abstract description 33
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- 238000003756 stirring Methods 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000003112 inhibitor Substances 0.000 claims abstract description 12
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 12
- 239000007921 spray Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000011347 resin Substances 0.000 claims abstract description 10
- 229920005989 resin Polymers 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 7
- SSCFPXRLONNQFA-UHFFFAOYSA-N methanol;hydrate;hydrochloride Chemical compound O.Cl.OC SSCFPXRLONNQFA-UHFFFAOYSA-N 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- -1 2, 3-epoxypropoxy Chemical group 0.000 claims description 6
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 229920001213 Polysorbate 20 Polymers 0.000 claims description 4
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims description 4
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 claims description 4
- DRRZZMBHJXLZRS-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]cyclohexanamine Chemical compound CO[Si](C)(OC)CCCNC1CCCCC1 DRRZZMBHJXLZRS-UHFFFAOYSA-N 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 4
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 claims description 3
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 claims description 3
- CHPNMYQJQQGAJS-UHFFFAOYSA-N 3-tri(propan-2-yloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCOC(=O)C(C)=C CHPNMYQJQQGAJS-UHFFFAOYSA-N 0.000 claims description 3
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- UJTGYJODGVUOGO-UHFFFAOYSA-N diethoxy-methyl-propylsilane Chemical compound CCC[Si](C)(OCC)OCC UJTGYJODGVUOGO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 claims description 3
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 abstract description 4
- 239000002131 composite material Substances 0.000 abstract description 2
- 230000007935 neutral effect Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- 239000002518 antifoaming agent Substances 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 239000005028 tinplate Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OGFYGJDCQZJOFN-UHFFFAOYSA-N [O].[Si].[Si] Chemical compound [O].[Si].[Si] OGFYGJDCQZJOFN-UHFFFAOYSA-N 0.000 description 1
- NOKSMMGULAYSTD-UHFFFAOYSA-N [SiH4].N=C=O Chemical compound [SiH4].N=C=O NOKSMMGULAYSTD-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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 System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
-
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- 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
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M155/00—Lubricating compositions characterised by the additive being a macromolecular compound containing atoms of elements not provided for in groups C10M143/00 - C10M153/00
- C10M155/02—Monomer containing silicon
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/046—Siloxanes with specific structure containing silicon-oxygen-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/047—Siloxanes with specific structure containing alkylene oxide groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/36—Release agents or mold release agents
Abstract
The invention discloses a functional silane macromolecular polymer, a preparation method, an additive and application, relates to the technical field of organic synthesis, and aims to solve the problem that the hardness of a coating cannot meet the requirement; the preparation method of the functional silane macromolecular polymer comprises the following steps: mixing a silane coupling agent and a solvent in proportion, adding a polymerization inhibitor, uniformly stirring, and dropwise adding a methanol-water-hydrochloric acid solution; reacting at normal temperature for a period of time after the dropwise addition is finished, collecting alcohol and solvent under reduced pressure, adding the solvent, heating for a period of time, adjusting to be neutral by using a pH regulator, removing the solvent through reduced pressure distillation, and filtering to obtain a silane macromolecular polymer; the invention has simple process, low production cost, no pollution, no need of high-temperature vacuum purification, high product yield, and can be applied to a coating and release agent system to replace resin, further improve the hardness, salt spray resistance and the like of the composite material.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a functional silane macromolecular polymer, a preparation method, an additive and application thereof.
Background
The silane coupling agent is mainly a product with a single structure, has the purity of more than 97 percent, is widely applied to industries such as glass fiber, solar photovoltaic, sealant, textile auxiliary agent, coating and the like, can provide excellent adhesive force and flexibility for the adhesion of organic and inorganic materials, but hardly contributes to the hardness of a coating, and causes the bottleneck of the related industries of the coating.
In the invention patent with publication number CN109575714B and name of 'A preparation method of hydrophilic long-acting durable antifogging coating modified based on silane coupling agent', the isocyanate silane coupling agent is used for carrying out chemical modification on polyvinyl alcohol to improve the hardness of the coating, and meanwhile, A surfactant is introduced as A hydrophilic regulator to improve the hydrophilicity of the coating and obtain long-acting durable scratch resistance and durable antifogging performance, but referring to GB/T6739-2006, the pencil hardness of the coating is measured by using A QHQ-A pencil hardness tester only can reach the level of 3H and can not meet the hardness requirement of the coating;
the invention patent with the publication number of CN101508852B and the name of 'seed high-hardness organic silicon protective coating and a preparation method and application thereof' discloses that silanization or oligosiloxane (methyl) hydroxyalkyl acrylate, a silicon functional organic silicon compound, alcohol or alcohol-water mixture and a photoinitiator are mixed, coated on the surface of a base material, and cured by ultraviolet irradiation to prepare a hydrophobic anticorrosive film with excellent adhesion, the hardness of a coating pencil is more than or equal to 6H, and the coating film has good surface protection performance and wear resistance; the pencil hardness of the coating film of the embodiment 10 reaches 9H; however, the method needs to adopt a photoinitiator and ultraviolet irradiation for curing, is not suitable for common natural drying or thermal drying and other modes, has unstable hardness, and has an expected average value of about 7H and still has a large promotion space;
at present, the hardness of the coating cannot meet the increasing material requirements, and the problems of not simple method or large pollution exist; therefore, a functional silane macromolecular polymer, a preparation method, an additive and an application thereof are needed to solve the problem.
Disclosure of Invention
The invention aims to provide a functional silane macromolecular polymer, a preparation method, an additive and application thereof, so as to solve the problem that the coating hardness cannot meet the requirement.
In order to achieve the purpose, the invention provides the following technical scheme: a functional silane macromolecular polymer, the chemical structure general formula is:
Wherein R is
R1is-OCH3、-OC2H5、-OCH(CH3)2or-OH, n is a positive integer from 1 to 6; m is a positive integer from 8 to 12.
The second technical scheme provided by the invention is as follows: a method for preparing a functional silane macromolecular polymer comprises the following specific steps:
s1: mixing a silane coupling agent and a solvent in proportion, adding a polymerization inhibitor, uniformly stirring, and dropwise adding a methanol-water-hydrochloric acid solution;
s2: after the dropwise addition, reacting at normal temperature for a period of time, collecting alcohol and solvent under reduced pressure, adding the solvent, heating for a period of time, adjusting to neutrality by using a pH regulator, distilling under reduced pressure to remove the solvent, and filtering to obtain the silane macromolecular polymer.
Preferably, the silane coupling agent is one or more of methacryloxypropyltrimethoxysilane, methacryloxypropylmethyldimethoxysilane, methacryloxypropyltriethoxysilane, methacryloxypropylmethyldiethoxysilane, methacryloxypropyltriisopropoxysilane, 3(2, 3-glycidoxy) propyltrimethoxysilane, 3(2, 3-glycidoxy) propyltriethoxysilane, 3(2, 3-glycidoxy) propylmethyldimethoxysilane, 3(2, 3-glycidoxy) propylmethyldiethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane, vinyltris (methoxyethoxy) silane.
Preferably, the solvent is methanol, ethanol, toluene, xylene, cyclohexane or isopropanol.
Preferably, the mass ratio of the silane coupling agent to the solvent is 1:2-1:3, the molar ratio of the silane coupling agent to the water is 1:3-1:4, the polymerization inhibitor is mixed ester, and the addition amount of the polymerization inhibitor is 0.02-0.03% of the total mass of the silane coupling agent and the solvent.
Preferably, in step S1, the pH of the methanol-water-hydrochloric acid solution is 3-5, and the dropping speed is 1 d/S.
Preferably, in the step S2, the reaction time at normal temperature is 5-8 h; the heating reaction is carried out at the temperature of 70-100 ℃ for 2-3 h; pH adjusters include, but are not limited to, sodium hydroxide, tetramethylammonium hydroxide, potassium hydroxide; the molecular weight of the silane macromolecular polymer is 500-4000.
The third technical scheme provided by the invention is as follows: a functional silane macromolecular polymer additive comprises the silane macromolecular polymer.
Preferably, the additive also comprises a surfactant, the mass of which is 5% of that of the silane macromolecular polymer, and the surfactant comprises, but is not limited to, tween 20, span 80 and polyethylene glycol.
The fourth technical scheme provided by the invention is as follows: the additive is added into the paint or the release agent or used as a substitute of resin to improve the hardness and the salt spray resistance of the paint or the release agent after being coated on the surface of a material and cured, and the addition amount of the additive is 10-20% of the mass of the paint or the release agent.
Compared with the prior art, the invention has the beneficial effects that:
the silane macromolecular polymer of the invention belongs to a new organosilicon product system, is a mixed structure, not only contains organic and inorganic functional groups, but also contains structures such as silicon-oxygen-silicon, silicon hydroxyl and the like, the product contains a large number of silicon-oxygen-silicon bonds, can obviously improve the hardness and the salt spray resistance of materials, and the silicon hydroxyl bonds can improve the adhesive force and the cohesive force with a base material, can be applied to the industries such as paint, mold release agent and the like, and can also replace the action of resin.
Compared with the POSS structural body of the organic silicon coupling agent researched at present, the molecular weight of the silane macromolecular polymer is 500-4000, the silane macromolecular polymer is a mixture containing various structural bodies of linear type, reticular type and POSS at the same time, the preparation method is simple in process, free of pollution, easy to obtain products and high in yield, a substance with a single structure does not need to be purified, the cost is greatly reduced, industrial production can be carried out, and the requirements for improving the hardness, salt spray resistance and other properties of the composite material are met.
Detailed Description
A functional silane macromolecular polymer, the chemical structure general formula is:
Wherein R is
R1is-OCH3、-OC2H5、-OCH(CH3)2or-OH, n is a positive integer from 1 to 6; m is a positive integer from 8 to 12.
The preparation method of the silane macromolecular polymer comprises the following steps:
mixing a silane coupling agent and a solvent in proportion, wherein the silane coupling agent can be one or more of methacryloxypropyltrimethoxysilane, methacryloxypropylmethyldimethoxysilane, methacryloxypropyltriethoxysilane, methacryloxypropylmethyldiethoxysilane, methacryloxypropyltriisopropoxysilane, 3(2, 3-epoxypropoxy) propyltrimethoxysilane, 3(2, 3-epoxypropoxy) propyltriethoxysilane, 3(2, 3-epoxypropoxy) propylmethyldimethoxysilane, 3(2, 3-epoxypropoxy) propylmethyldiethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane and vinyltris (methoxyethoxy) silane; the molar ratio of the silane coupling agent to the water is preferably 1:3-1:4, and the mass ratio of the silane coupling agent to the solvent is preferably 1:2-1: 3;
after mixing, adding a polymerization inhibitor, preferably mixed esters, wherein the addition amount of the polymerization inhibitor is 0.02-0.03% of the total mass of the silane coupling agent and the solvent, dropwise adding a methanol-water-hydrochloric acid solution after uniformly stirring, wherein the pH value is preferably 3-5, and the dropwise adding speed can be 1 d/s;
reacting at normal temperature for 5-8h after the dropwise addition is finished, collecting alcohol and solvent under reduced pressure, adding the solvent, heating to 70-100 ℃ for reacting for 2-3h, adjusting to be neutral by using a pH regulator, wherein the pH regulator can adopt sodium hydroxide, tetramethylammonium hydroxide, potassium hydroxide and the like, distilling under reduced pressure to remove the solvent, and filtering to obtain the silane macromolecular polymer with the molecular weight of 500-4000.
The solvent can be selected from methanol, ethanol, toluene, xylene, cyclohexane or isopropanol.
The prepared silane macromolecular polymer can be used as an additive to be added into a coating or a release agent or used as a substitute of resin to improve the hardness and the salt spray resistance of the coating or the release agent after being coated on the surface of a material and cured, and the addition amount is preferably 10-20% of the mass of the coating or the release agent; in addition, the additive can also be added with a surfactant, the added mass of the surfactant is preferably 5% of that of the silane macromolecular polymer, and the surfactant can be Tween 20, span 80, polyethylene glycol and the like.
Example 1:
248g of 3-methacryloxypropyltrimethoxysilane and 496g of methanol are added into a 1000ml three-neck flask with a stirring device, 0.15g of polymerization inhibitor is added, the mixture is stirred uniformly, 100g of methanol/water/hydrochloric acid solution is dripped, and the dripping speed is controlled to be 1 d/s; reacting at normal temperature for 8h after dropwise adding, reducing pressure after the reaction is finished, collecting 550g of methanol, adding 200g of toluene, reacting at 100 ℃ for 3h, adjusting the pH of the solution to 7 by using a tetramethylammonium hydroxide solution, removing 306g of solvent by reduced pressure distillation, and filtering to obtain 180g of silane macromolecular polymer; one of the reaction equations of the preparation process is as follows:
the silane macromolecular polymer product is colorless transparent viscous liquid, and the calculated yield is more than 95 percent and the viscosity is 1000mm according to the yield which is the actual mass of the product/the theoretical mass of the product which is 100 percent2(s) average molecular weight 1860.
The silane macromolecular polymer is added into a release agent for use, so that the release is easier, and the surface of a separated finished product is flat, smooth and free from damage.
Example 2:
220g of 3(2, 3-glycidoxy) propyl methyldimethoxysilane and 475g of methanol are put into a 1000ml three-neck flask with a stirring device, 0.15g of polymerization inhibitor is added, the mixture is stirred evenly, 100g of methanol/water/hydrochloric acid solution is dripped, and the dripping speed is controlled to be 1 d/s; reacting at normal temperature for 6h after the dropwise addition is finished, reducing pressure after the reaction is finished, collecting 520g of methanol, adding 200g of isopropanol, refluxing and reacting at 80 ℃ for 2.5h, adjusting the pH of the solution to 6 by using a potassium hydroxide solution, removing 295g of solvent by reduced pressure distillation, and filtering to obtain 167g of a silane macromolecular polymer; one of the reaction equations of the preparation process is as follows:
the silane macromolecular polymer product is colorless transparent viscous liquid, and the calculated yield is more than 92 percent and the viscosity is 500mm according to the yield which is the actual mass of the product/the theoretical mass of the product which is 100 percent2(s) average molecular weight 1450.
The silane macromolecular polymer is added into a release agent for use, so that the release is easier, and the surface of a separated finished product is flat, smooth and free from damage.
Example 3:
adding 190g of vinyltriethoxysilane and 500g of ethanol into 1000ml of three-neck flask with a stirring device, adding 0.22g of polymerization inhibitor, uniformly stirring, dropwise adding 100g of ethanol/water/hydrochloric acid solution, and controlling the dropwise adding speed to be 1 d/s; reacting at normal temperature for 5h after dropwise adding, reducing pressure after the reaction is finished, collecting 600g of methanol, adding 200g of cyclohexane, refluxing and reacting at 75 ℃ for 2h, adjusting the pH of the solution to 6 by using a sodium hydroxide solution, removing 282g of solvent by reduced pressure distillation, and filtering to obtain 98g of silane macromolecular polymer; one of the reaction equations of the preparation process is as follows:
the silane macromolecular polymer product is colorless transparent viscous liquid, and the calculated yield is more than 90 percent and the viscosity is 300mm according to the yield which is the actual mass of the product/the theoretical mass of the product which is 100 percent2(s) average molecular weight 1030.
The silane macromolecular polymer is added into a release agent for use, so that the release is easier, and the surface of a separated finished product is flat, smooth and free from damage.
Example 4:
the blank coating is prepared according to the following steps: after heating 10 parts by mass of E51 epoxy resin to 100 ℃, 0.2 part by mass of defoaming agent (BYK-A535) and 0.2 part by mass of leveling agent (BYK 371) are added and stirred at a constant speed. The resin system was dissolved in 40 parts by mass of a toluene solvent (analytical grade), stirred uniformly at room temperature and then allowed to stand. The solvent was evaporated at 25 ℃. Then adding 0.8 part by mass of ethylenediamine (analytically pure), and uniformly stirring to obtain a blank coating;
adding 9g of Tween 20 into 180g of the silane macromolecular polymer in the example 1, uniformly stirring to obtain an additive, adding 10 mass percent of the additive into the blank coating, uniformly mixing, uniformly coating the mixture on the surface of a clean tinplate base material, waiting for complete curing, testing the hardness of the coating according to GB/T6739-2006, and testing the salt spray resistance of the coating according to GB/T1771-91.
Example 5:
the blank coating is prepared according to the following steps: after 8.5 parts by mass of E51 epoxy resin is heated to 100 ℃, 0.2 part by mass of defoaming agent (BYK-A535) and 0.2 part by mass of leveling agent (BYK 371) are added and stirred at a constant speed. The resin system was dissolved in 40 parts by mass of a toluene solvent (analytical grade), stirred uniformly at room temperature and then allowed to stand. The solvent was evaporated at 25 ℃. Then adding 0.8 part by mass of ethylenediamine (analytically pure), and uniformly stirring to obtain a blank coating;
adding 8.5g of span 80 into 167g of the silane macromolecular polymer in the example 2, uniformly stirring to obtain an additive, taking the blank coating, adding 15% of the additive by mass, uniformly mixing, uniformly coating the mixture on the surface of a clean tinplate base material, waiting for complete curing, testing the hardness of the coating according to GB/T6739-2006, and testing the salt spray resistance of the coating according to GB/T1771-91.
Example 6:
the blank coating is prepared according to the following steps: after 8 parts by mass of E51 epoxy resin is heated to 100 ℃, 0.2 part by mass of defoaming agent (BYK-A535) and 0.2 part by mass of leveling agent (BYK 371) are added and stirred at a constant speed. The resin system was dissolved in 40 parts by mass of a toluene solvent (analytical grade), stirred uniformly at room temperature and then allowed to stand. The solvent was evaporated at 25 ℃. Then adding 0.8 part by mass of ethylenediamine (analytically pure), and uniformly stirring to obtain a blank coating;
adding 5g of polyethylene glycol into 98g of the silane macromolecular polymer in the embodiment 3, uniformly stirring the mixture to serve as an additive, adding 20 mass percent of the additive into the blank coating, uniformly mixing the mixture, uniformly coating the mixture on the surface of a clean tinplate base material, waiting for complete curing, testing the hardness of the coating according to GB/T6739-2006, and testing the salt spray resistance of the coating according to GB/T1771-91.
Comparative example 1:
the blank coating is prepared according to the following steps: after 8 parts by mass of E51 epoxy resin is heated to 100 ℃, 0.2 part by mass of defoaming agent (BYK-A535) and 0.2 part by mass of leveling agent (BYK 371) are added and stirred at a constant speed. The resin system was dissolved in 40 parts by mass of a toluene solvent (analytical grade), stirred uniformly at room temperature and then allowed to stand. The solvent was evaporated at 25 ℃. Then adding 0.8 part by mass of ethylenediamine (analytically pure), and uniformly stirring to obtain a blank coating;
adding 2 parts by mass of acrylic resin into the blank coating, uniformly mixing, uniformly coating the mixture on the surface of a clean tinplate base material, waiting for complete curing, testing the hardness of the coating according to GB/T6739-2006, and testing the salt spray resistance of the coating according to GB/T1771-91.
Comparative example 2:
the blank coating is prepared according to the following steps: after heating 10 parts by mass of E51 epoxy resin to 100 ℃, 0.2 part by mass of defoaming agent (BYK-A535) and 0.2 part by mass of leveling agent (BYK 371) are added and stirred at a constant speed. The resin system was dissolved in 40 parts by mass of a toluene solvent (analytical grade), stirred uniformly at room temperature and then allowed to stand. The solvent was evaporated at 25 ℃. And adding 0.8 part by mass of ethylenediamine (analytically pure), uniformly stirring to obtain a blank coating, directly and uniformly coating the blank coating on the surface of a clean tinplate base material, waiting for complete curing, testing the hardness of the coating according to GB/T6739-2006, and testing the salt spray resistance of the coating according to GB/T1771-91.
The results of the tests of examples 4, 5, 6 and comparative examples 1, 2 are as follows:
| detecting items | Detection method | Example 4 | Example 5 | Example 6 | Comparative example 1 | Comparative example 2 |
| Hardness of | GB/T6739-2006 | 9H | 9H | 9H | 6H | 5H |
| Salt fog resistance | GB/T1771-91 | ≥1000h | ≥1000h | ≥1000h | 600h | 600h |
The detection results show that compared with comparative example 1 and comparative example 2, the hardness of the coatings in examples 4, 5 and 6 is obviously improved, and the salt spray resistance is improved by more than 30%.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are also included in the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope defined by the claims.
The present invention is not described in detail, but is known to those skilled in the art.
Claims (10)
1. A functional silane macromolecular polymer is characterized in that the chemical structure general formula is as follows:
Wherein R is
R1is-OCH3、-OC2H5、-OCH(CH3)2or-OH, n is a positive integer from 1 to 6; m is a positive integer from 8 to 12.
2. A method for preparing a functional silane macromolecular polymer according to claim 1, characterized by comprising the following steps:
s1: mixing a silane coupling agent and a solvent in proportion, adding a polymerization inhibitor, uniformly stirring, and dropwise adding a methanol-water-hydrochloric acid solution;
s2: after the dropwise addition, reacting at normal temperature for a period of time, collecting alcohol and solvent under reduced pressure, adding the solvent, heating for a period of time, adjusting to neutrality by using a pH regulator, distilling under reduced pressure to remove the solvent, and filtering to obtain the silane macromolecular polymer.
3. The method for preparing a functional silane macromolecular polymer according to claim 2, characterized in that: the silane coupling agent is one or more of methacryloxypropyltrimethoxysilane, methacryloxypropylmethyldimethoxysilane, methacryloxypropyltriethoxysilane, methacryloxypropylmethyldiethoxysilane, methacryloxypropyltriisopropoxysilane, 3(2, 3-epoxypropoxy) propyltrimethoxysilane, 3(2, 3-epoxypropoxy) propyltriethoxysilane, 3(2, 3-epoxypropoxy) propylmethyldimethoxysilane, 3(2, 3-epoxypropoxy) propylmethyldiethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane and vinyltris (methoxyethoxy) silane.
4. The method for preparing a functional silane macromolecular polymer according to claim 2, characterized in that: the solvent is methanol, ethanol, toluene, xylene, cyclohexane or isopropanol.
5. The method for preparing a functional silane macromolecular polymer according to claim 2, characterized in that: the mass ratio of the silane coupling agent to the solvent is 1:2-1:3, and the molar ratio of the silane coupling agent to the water is 1:3-1: 4; the polymerization inhibitor is mixed ester, and the addition amount of the polymerization inhibitor is 0.02-0.03 percent of the total mass of the silane coupling agent and the solvent.
6. The method for preparing a functional silane macromolecular polymer according to claim 2, characterized in that: in the step S1, the pH of the methanol-water-hydrochloric acid solution is 3-5, and the dropping speed is 1 d/S.
7. The method for preparing a functional silane macromolecular polymer according to claim 2, characterized in that: in the step S2, the reaction time at normal temperature is 5-8 h; the heating reaction is carried out at the temperature of 70-100 ℃ for 2-3 h; pH adjusters include, but are not limited to, sodium hydroxide, tetramethylammonium hydroxide, potassium hydroxide; the molecular weight of the silane macromolecular polymer is 500-4000.
8. A functional silane macromolecular polymer additive, characterized by comprising the silane macromolecular polymer according to any one of claims 1 to 7.
9. The functional silane macromolecular polymer additive according to claim 8, characterized in that: and the surfactant is 5% of the mass of the silane macromolecular polymer, and the surfactant comprises, but is not limited to, Tween 20, span 80 and polyethylene glycol.
10. Use of an additive according to claim 8 or 9, wherein: the additive is added into the coating or the release agent or used as a substitute of resin to improve the hardness and the salt spray resistance of the coating or the release agent after being coated on the surface of a material and cured, and the addition amount of the additive is 10-20% of the mass of the coating or the release agent.
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