CN111116822B - Acrylic resin composition - Google Patents
Acrylic resin composition Download PDFInfo
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- CN111116822B CN111116822B CN201911420221.3A CN201911420221A CN111116822B CN 111116822 B CN111116822 B CN 111116822B CN 201911420221 A CN201911420221 A CN 201911420221A CN 111116822 B CN111116822 B CN 111116822B
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- acrylic resin
- resin composition
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- acid
- acrylic acid
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- 239000004925 Acrylic resin Substances 0.000 title claims abstract description 53
- 229920000178 Acrylic resin Polymers 0.000 title claims abstract description 53
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000003822 epoxy resin Substances 0.000 claims abstract description 11
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 11
- 239000003085 diluting agent Substances 0.000 claims abstract description 8
- 239000003999 initiator Substances 0.000 claims abstract description 8
- 239000000945 filler Substances 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical group CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical group C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 5
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 claims description 5
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 claims description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 5
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 3
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 3
- -1 N-dimethylacrylamide Chemical compound 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 239000012763 reinforcing filler Substances 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- VEQSPDDHYUFBSP-UHFFFAOYSA-N 1,3-bis(1-hydroxycyclohexyl)-1,3-diphenylpropan-2-one Chemical compound C=1C=CC=CC=1C(C1(O)CCCCC1)C(=O)C(C=1C=CC=CC=1)C1(O)CCCCC1 VEQSPDDHYUFBSP-UHFFFAOYSA-N 0.000 claims description 2
- WDFFWUVELIFAOP-UHFFFAOYSA-N 2,6-difluoro-4-nitroaniline Chemical compound NC1=C(F)C=C([N+]([O-])=O)C=C1F WDFFWUVELIFAOP-UHFFFAOYSA-N 0.000 claims description 2
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 2
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002978 peroxides Chemical group 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims 2
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims 1
- NNAHKQUHXJHBIV-UHFFFAOYSA-N 2-methyl-1-(4-methylthiophen-2-yl)-2-morpholin-4-ylpropan-1-one Chemical compound CC1=CSC(C(=O)C(C)(C)N2CCOCC2)=C1 NNAHKQUHXJHBIV-UHFFFAOYSA-N 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 abstract description 9
- 150000007524 organic acids Chemical class 0.000 abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 abstract description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract description 5
- 229920005749 polyurethane resin Polymers 0.000 abstract description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002861 polymer material Substances 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910021485 fumed silica Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 238000005464 sample preparation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/22—Esters containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
- C08F283/008—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
- C08F283/105—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule on to unsaturated polymers containing more than one epoxy radical per molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention belongs to the technical field of high polymer materials, and particularly relates to an acrylic resin composition. The acrylic resin composition prepared by the invention comprises the following raw materials in parts by weight: 50-90 parts of modified acrylic acid, 10-40 parts of reactive diluent, 1-30 parts of filler and 1-6 parts of thermal initiator. The modified acrylic acid is polymerized by tri (2-hydroxyethyl) isocyanurate and organic acid or organic alcohol containing carbon-carbon double bonds, organic acid or organic alcohol or organic amine or polyurethane or epoxy resin. The modified acrylic resin composition prepared from the modified acrylic acid prepared by the invention can be rapidly cured at a lower temperature, so that the curing rate of the acrylic resin composition at the low temperature is improved, and the application range of the acrylic resin composition is widened.
Description
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to an acrylic resin composition.
Background
Acrylic resin has excellent properties such as light color, high transparency, brightness, toughness, strong adhesion, corrosion resistance and the like, and is widely used. But the conventional acrylic thermosetting temperature is typically 100-. The acrylic resin can be cured at a higher temperature, so that the energy consumption is high, and the application of the acrylic resin in non-high temperature fields is limited. For example, when the acrylic resin composition is used as a coating on glass, the acrylic resin composition needs to be cured at 100-140 ℃, but the temperature may cause the glass to suddenly cool and crack at a higher temperature. Therefore, the problem that the curing temperature of the acrylic resin is lowered so that the acrylic resin can be rapidly cured at a lower temperature is urgently needed to be solved in the application process of the acrylic resin. In addition, in recent years, with the rapid development of science and technology, people have higher requirements on living standards, and the traditional acrylic resin cannot well meet the requirements of industrial production because certain defects such as poor performances such as hardness, strength and the like exist in the application process.
Disclosure of Invention
In order to solve the problems, the invention adopts the following technical scheme:
an acrylic resin composition comprises the following raw materials in parts by weight: 50-90 parts of modified acrylic acid, 10-40 parts of reactive diluent, 1-6 parts of thermal initiator and 1-30 parts of filler;
the chemical reaction equation for preparing modified acrylic acid is as follows:
wherein R is1Selected from organic acids containing carbon-carbon double bonds or organic alcohols containing carbon-carbon double bonds;
R2one selected from organic acid, organic alcohol, organic amine, polyurethane and epoxy resin;
R3is selected from one of organic acid, organic alcohol, organic amine, polyurethane and epoxy resin.
Further, the chemical reaction equation of the modified acrylic acid is as follows:
wherein R is1Selected from organic acids containing carbon-carbon double bonds or organic alcohols containing carbon-carbon double bonds;
R2one selected from polybasic organic acid, polybasic organic alcohol, polybasic organic amine, polyurethane and epoxy resin;
R3is selected from one of monobasic organic acid, monobasic organic alcohol, monobasic organic amine, polyurethane and epoxy resin.
Further, the reactive diluent is one or a mixture of acrylic acid, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, isobornyl acrylate, ethoxy ethyl acrylate, lauric acrylate, hydroxypropyl methacrylate, hydroxyethyl methacrylate, N-dimethylacrylamide, glycidyl methacrylate, tricyclodecane dimethanol diacrylate, 1, 6-hexanediol diacrylate, propoxylated neopentyl glycol diacrylate, 2-hydroxyethyl methacrylate phosphate, trimethylolpropane triacrylate and pentaerythritol triacrylate.
Further, the addition of the reactive diluent during the preparation of the acrylic resin composition can reduce the viscosity of the acrylic resin composition and facilitate the curing reaction.
Further, the thermal initiator is a compound having an azo or peroxy structure.
Further, the thermal initiator may be one of azobisisobutyronitrile, azobisisoheptonitrile, diacyl peroxide, dialkyl peroxide and diester peroxide.
Furthermore, 1-6 parts of photoinitiator can be added in the process of preparing the acrylic resin composition, and the prepared acrylic resin composition can be cured under the condition of ultraviolet irradiation by adding the photoinitiator in the process of preparing the acrylic resin composition.
Further, the photoinitiator is one or a mixture of 2,4,6- [ trimethylbenzoyl ] diphenylphosphine oxide, 2,4,6- [ trimethylbenzoyl ] phosphonic acid ethyl ester, 2-methyl-1- [ 4-methylthiophenyl ] -2-morpholinyl-1-acetone, 2-isopropyl thioxanthone, 1-hydroxy-cyclohexyl-benzyl ketone, tert-butyl peroxy (2-ethylhexanoate) and 4-chlorobenzophenone.
Furthermore, the filler is one or more of pigment, reinforcing filler, thickening agent and fluorescent agent.
Further, the pigment is carbon black or color paste.
Further, the reinforcing filler is fumed silica.
Further, the thickener is fumed silica.
Further, the chemical reaction equation for preparing modified acrylic acid is as follows:
wherein R is1Is acrylic acid or methacrylic acid;
R2is one of dicarboxylic acid, bisphenol F type epoxy resin and polyurethane;
R3is one of acetic acid and n-octanoic acid.
Further, the chemical reaction equation for preparing modified acrylic acid is as follows:
wherein R is1Is acrylic acid; r2Is acetic acid; r3Is acetic acid.
Further, the chemical reaction equation for preparing modified acrylic acid is as follows:
wherein R is1Is methacrylic acid; r2Is bisphenol F type epoxy resin; r3Is n-octanoic acid.
Further, the chemical reaction equation for preparing modified acrylic acid is as follows:
wherein R is1Is methacrylic acid; r2Is isocyanate-terminated polyurethane prepolymer; r3Is n-octanoic acid.
Further, the modified acrylic acid is prepared by the following method: adding tris (2-hydroxyethyl) isocyanurate and R into a reaction vessel1、R2、R3Mixing the catalyst and the polymerization inhibitor, stirring, heating, cooling, washing with water, distilling, removing the solvent, and filtering to obtain the modified acrylic acid.
Further, the acrylic resin composition of the present invention is prepared by the following method: weighing modified acrylic acid, reactive diluent, thermal initiator and filler according to the parts by weight, mixing the raw materials, stirring, defoaming and curing to obtain the acrylic resin composition.
Compared with the prior art, the invention achieves the following beneficial effects:
in the invention, the tri (2-hydroxyethyl) isocyanurate is added in the process of preparing the modified acrylic acid, the tri (2-hydroxyethyl) isocyanurate can reduce the curing temperature of the prepared modified acrylic acid, and the modified acrylic resin composition prepared from the modified acrylic acid can be rapidly cured at lower temperature compared with the traditional acrylic resin composition, thereby reducing the energy consumption and widening the application range of the acrylic resin composition. In addition, epoxy resin or polyurethane can be added into the prepared modified acrylic resin, the epoxy resin has the characteristics of high strength, good adhesiveness and the like, the polyurethane has the advantages of mechanical wear resistance, low temperature resistance, good flexibility, high adhesive strength and the like, and the acrylic resin is modified by the epoxy resin or the polyurethane, so that the strength, wear resistance, flexibility and other properties of the prepared acrylic resin are improved. The acrylic acid composition prepared by using the prepared modified acrylic acid can be cured at low temperature and can be cured by light, and the mechanical property is improved.
Detailed Description
The technical solutions of the present invention will be described in detail and fully with reference to the following embodiments, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparation of modified acrylic acid:
the reactor was placed on a stirrer and 20 g of tris (2-hydroxyethyl) isocyanurate, 11 g of acrylic acid, 5 g of acetic acid, 25 g of toluene, 6 g of n-heptane, 1.5 g of p-toluenesulfonic acid and 0.1 g of hydroquinone were added to the reactor in this order. And (3) heating the temperature of the reactor to 80 ℃, stirring for 1 hour, then heating the reactor to 115 ℃, and stirring for 4-6 hours to obtain the product. And cooling the product to room temperature, washing the product for three times by using deionized water, distilling the product under reduced pressure, removing the solvent in the product, and filtering the product to obtain the modified acrylic acid.
Preparation of acrylic resin composition:
taking 10 g of the modified acrylic acid prepared above, adding 3 g of isobornyl acrylate, adding 0.25 g of tert-butyl peroxy (2-ethylhexanoate) and 0.3 g of silicon dioxide, stirring and defoaming, and then placing in an oven at 80 ℃ for heating for 30min to cure, thus obtaining the acrylic resin composition.
Example 2
Preparation of modified acrylic acid:
placing a reactor on a stirrer, sequentially adding 20 g of tris (2-hydroxyethyl) isocyanurate, 18.6 g of bisphenol F epoxy resin, 0.025 g of concentrated sulfuric acid and 30 g of toluene into the reactor, heating to 130 ℃, stirring for 4-6 hours, cooling to 80 ℃, adding 0.08 g of p-tert-butylphenol, 0.04 g of hydroquinone, 1 g of p-toluenesulfonic acid and 8 g of cyclohexane into the reactor, stirring for 10 minutes, then adding 6.56 g of methacrylic acid and 11.3 g of n-octanoic acid, heating to 125 ℃, and stirring for 4-6 hours to obtain the product. And cooling the product to room temperature, washing the product for three times by using deionized water, distilling the product under reduced pressure, removing the solvent in the product, and filtering the product to obtain the modified acrylic acid.
Preparation of acrylic resin composition:
taking 10 g of the modified acrylic acid, adding 3 g of isobornyl acrylate, 3 g of 1, 6-hexanediol diacrylate, 0.3 g of tert-butyl peroxy (2-ethylhexanoate) and 0.15 g of silicon dioxide, stirring and defoaming, and then placing the mixture into an oven at 80 ℃ to heat for 30min for curing, thus obtaining the acrylic resin composition.
Example 3
Preparation of modified acrylic acid:
the reaction vessel was placed on a stirrer, and 20 g of tris (2-hydroxyethyl) isocyanurate, 8.53 g of methacrylic acid, 8.24 g of n-octanoic acid, 25 g of toluene, 6 g of n-heptane, 0.36 g of p-toluenesulfonic acid, and 0.1 g of hydroquinone were added to the reactor in this order. And heating the reactor to 80 ℃, stirring for 1 hour, heating to 100 ℃, stirring for 2-3 hours, cooling the reactor to room temperature, and performing water removal treatment. And then adding 30 g of isocyanate-terminated polyurethane prepolymer and 0.02 g of environment-friendly catalyst into the reactor, and stirring for 3-4 hours to obtain the product. Washing the product with deionized water for three times, distilling under reduced pressure, removing the solvent in the product, and filtering to obtain the modified acrylic acid.
Preparation of acrylic resin composition:
taking 10 g of the modified acrylic acid, adding 3 g of isobornyl acrylate, 0.3 g of tert-butyl peroxy (2-ethylhexanoate) and 0.15 g of silicon dioxide, stirring and defoaming, and then placing the mixture into an oven at 80 ℃ to heat for 30min for curing to obtain the acrylic resin composition.
Comparative example 1
Comparative example 1 was set on the basis of example 1, and comparative example 1 was different from example 1 in that the acrylic resin used in comparative example 1 was a conventional acrylic resin, and an acrylic resin composition was prepared in the same manner as in example 1.
1. Sample preparation and curing
(1) The sample preparation method comprises the following steps: the same reactive diluent and thermal initiator in the same proportion are added into the acrylic resin in examples 1-3 and comparative example 1, three groups of tests are prepared under each condition, and an average value is taken;
(2) curing conditions are as follows: the temperature is 80 deg.C, and the time is 30 min. If the comparative example is not cured under the same conditions, the temperature is increased to 120 ℃ and the curing is carried out by heating for 30min, so that the subsequent performance comparison is facilitated.
(3) The physical property test standard is as follows:
viscosity-GB/T22235-
hardness-GB/T2411-
Shear strength-GB/T2411-
Elongation at Break-GB/T2411-
2. The results of comparative testing of curing speed and physical properties are shown in Table 1.
TABLE 1 curing temperature and physical Properties test of examples 1-3 and comparative example 1
In conclusion, the acrylic resin composition prepared by using the modified acrylic resin prepared in the present invention has a lower viscosity than that of the acrylic resin composition prepared by using the conventional acrylic resin, and can be rapidly cured under the heating condition of 80 ℃. Therefore, the modified acrylic acid prepared in the document effectively reduces the curing temperature of the acrylic resin, reduces the energy consumption and widens the application range of the acrylic resin composition in the low-temperature field.
The present invention has been further described with reference to specific embodiments, but it should be understood that the detailed description should not be construed as limiting the spirit and scope of the present invention, and various modifications made to the above-described embodiments by those of ordinary skill in the art after reading this specification are within the scope of the present invention.
Claims (6)
1. The acrylic resin composition is characterized by comprising the following raw materials in parts by mass: 50-90 parts of modified acrylic acid, 10-40 parts of reactive diluent, 1-30 parts of filler and 1-6 parts of thermal initiator;
the chemical reaction equation for preparing the modified acrylic acid is as follows:
wherein R1 is methacrylic acid; r2 is bisphenol F type epoxy resin; r3 is n-octanoic acid;
or R1 is methacrylic acid; r2 is an isocyanate-terminated polyurethane prepolymer; r3Is n-octanoic acid;
the modified acrylic acid is prepared by the following method: adding said tris (2-hydroxyethyl) isocyanurate, said R to a reaction vessel1The R is2Catalytic reaction ofMixing a curing agent and a polymerization inhibitor, stirring, heating, cooling, washing with water, distilling, removing a solvent, and filtering to obtain the modified acrylic acid.
2. The acrylic resin composition as claimed in claim 1, wherein the reactive diluent is one or more selected from the group consisting of acrylic acid, tetrahydrofurfuryl acrylate, tetrahydrofurfuryl methacrylate, isobornyl acrylate, ethoxyethoxyethyl acrylate, lauric acrylate, hydroxypropyl methacrylate, hydroxyethyl methacrylate, N-dimethylacrylamide, glycidyl methacrylate, tricyclodecane dimethanol diacrylate, 1, 6-hexanediol diacrylate, propoxylated neopentyl glycol diacrylate, 2-hydroxyethyl methacrylate phosphate, trimethylolpropane triacrylate, and pentaerythritol triacrylate.
3. The acrylic resin composition as claimed in claim 1, wherein said thermal initiator is a compound having an azo or peroxide structure.
4. The acrylic resin composition as claimed in claim 1, wherein the filler is one or more of pigment, reinforcing filler, thickener and fluorescent agent.
5. The acrylic resin composition as claimed in claim 1, further comprising 1-6 parts of a photoinitiator.
6. The acrylic resin composition as claimed in claim 5, wherein the photoinitiator is one or more selected from the group consisting of 2,4,6- [ trimethylbenzoyl ] diphenylphosphine oxide, ethyl 2,4,6- [ trimethylbenzoyl ] phosphonate, 2-methyl-1- [ 4-methylthiophenyl ] -2-morpholinyl-1-propanone, 2-isopropylthioxanthone, 1-hydroxy-cyclohexyl-benzyl ketone, tert-butyl peroxy (2-ethylhexanoate) and 4-chlorobenzophenone.
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