CN115755469A - Sealing frame adhesive for liquid crystal panel and preparation method thereof - Google Patents
Sealing frame adhesive for liquid crystal panel and preparation method thereof Download PDFInfo
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- CN115755469A CN115755469A CN202211498846.3A CN202211498846A CN115755469A CN 115755469 A CN115755469 A CN 115755469A CN 202211498846 A CN202211498846 A CN 202211498846A CN 115755469 A CN115755469 A CN 115755469A
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- Prior art keywords
- curing agent
- compound
- anhydride
- liquid crystal
- acid
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 31
- 238000007789 sealing Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 239000000853 adhesive Substances 0.000 title description 7
- 230000001070 adhesive effect Effects 0.000 title description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 71
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000004593 Epoxy Substances 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- -1 anhydride compound Chemical class 0.000 claims abstract description 18
- 239000000565 sealant Substances 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 15
- 239000011347 resin Substances 0.000 claims abstract description 15
- 229920005989 resin Polymers 0.000 claims abstract description 15
- 239000003292 glue Substances 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 117
- 238000003756 stirring Methods 0.000 claims description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 30
- 239000000945 filler Substances 0.000 claims description 20
- 238000000227 grinding Methods 0.000 claims description 15
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 14
- 239000000377 silicon dioxide Substances 0.000 claims description 14
- 239000011259 mixed solution Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- 238000007259 addition reaction Methods 0.000 claims description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- 239000011859 microparticle Substances 0.000 claims description 8
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical compound NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 claims description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 5
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 claims description 4
- XSXYESVZDBAKKT-UHFFFAOYSA-N 2-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1O XSXYESVZDBAKKT-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 229910021647 smectite Inorganic materials 0.000 claims description 4
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 3
- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000003825 pressing Methods 0.000 claims description 3
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 claims description 2
- QNYBOILAKBSWFG-UHFFFAOYSA-N 2-(phenylmethoxymethyl)oxirane Chemical compound C1OC1COCC1=CC=CC=C1 QNYBOILAKBSWFG-UHFFFAOYSA-N 0.000 claims description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims description 2
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 claims description 2
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 claims description 2
- JVCJCQIOQITEIF-UHFFFAOYSA-N 2-undecylpropanedihydrazide Chemical compound CCCCCCCCCCCC(C(=O)NN)C(=O)NN JVCJCQIOQITEIF-UHFFFAOYSA-N 0.000 claims description 2
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 claims description 2
- CYCBPQPFMHUATH-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)butan-1-ol Chemical compound OCCCCOCC1CO1 CYCBPQPFMHUATH-UHFFFAOYSA-N 0.000 claims description 2
- PBNUQCWZHRMSMS-UHFFFAOYSA-N 5-propan-2-ylimidazolidine-2,4-dione Chemical compound CC(C)C1NC(=O)NC1=O PBNUQCWZHRMSMS-UHFFFAOYSA-N 0.000 claims description 2
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 claims description 2
- 239000005909 Kieselgur Substances 0.000 claims description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 2
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 239000010425 asbestos Substances 0.000 claims description 2
- 239000011324 bead Substances 0.000 claims description 2
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 239000000378 calcium silicate Substances 0.000 claims description 2
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- 239000010440 gypsum Substances 0.000 claims description 2
- 229910052602 gypsum Inorganic materials 0.000 claims description 2
- AQTNCAREYVLVMX-UHFFFAOYSA-N icosanedihydrazide Chemical compound NNC(=O)CCCCCCCCCCCCCCCCCCC(=O)NN AQTNCAREYVLVMX-UHFFFAOYSA-N 0.000 claims description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 2
- 239000001095 magnesium carbonate Substances 0.000 claims description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 229910052895 riebeckite Inorganic materials 0.000 claims description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 2
- 229910001887 tin oxide Inorganic materials 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 abstract description 9
- 239000002262 Schiff base Substances 0.000 abstract description 3
- 150000004753 Schiff bases Chemical class 0.000 abstract description 3
- 230000006866 deterioration Effects 0.000 abstract description 3
- 238000006845 Michael addition reaction Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 12
- 238000011085 pressure filtration Methods 0.000 description 10
- 150000003141 primary amines Chemical class 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 8
- 239000000758 substrate Substances 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012945 sealing adhesive Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
- G02F1/13398—Spacer materials; Spacer properties
Landscapes
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Epoxy Resins (AREA)
Abstract
The invention relates to the field of sealing frame glue, and particularly discloses a sealing frame glue of a liquid crystal panel and a preparation method thereof, wherein the technical scheme is as follows: the curing agent is an adduct consisting of a hydrazide compound (A) and an epoxy compound (B) or an acid or anhydride compound (C), and compared with the original curing agent, the curing agent adduct reduces primary amine in the curing agent, avoids the sealant from reacting, such as Schiff base reaction and Michael addition reaction, avoids the deterioration of the storage stability of the resin, and ensures that the frame sealant has excellent storage stability and curing property.
Description
Technical Field
The invention relates to the field of sealing frame glue, in particular to sealing frame glue of a liquid crystal panel and a preparation method thereof.
Background
In recent years, in order to improve production efficiency and to use liquid crystal in a large quantity, the manufacturing method of a liquid crystal panel display element is gradually changed from the conventional vacuum injection method to the liquid crystal dropping method. Liquid crystal dropping process: a circle of sealant is coated on a transparent substrate with electrodes to form a rectangular sealing pattern, then a certain amount of liquid crystal is dripped into a sealing frame of the substrate before the sealant is cured, and two transparent substrates with electrodes are bonded in a vacuum state. Then, the sealant is irradiated by UV for temporary curing, and finally, the liquid crystal is annealed for main curing. In the liquid crystal dropping method, in view of rapid curing, a radical polymerization reactive compound having an epoxy acrylate compound as a main component is currently used in many cases as a liquid crystal sealing agent.
With the popularization of smart phones, tablet terminals, and the like, there is an increasing demand for small liquid crystal panels, and since the liquid crystal drop site is close to the sealing frame, the liquid crystal comes into contact with the uncured sealant for a long time after the attachment until UV irradiation, and there is a problem of contamination of the liquid crystal and the uncured sealant. In addition, the flexible liquid crystal display which is light in weight, safe and can be freely bent is gradually expanded in the market. Many conventional sealants are relatively rigid cured products and are suitable for bonding substrates such as glass having a small amount of deformation. In the case of a flexible display, the substrate may be peeled or broken due to a change in shape.
Chinese patent No. CN101484844A discloses a liquid crystal sealant and a liquid crystal display unit using the same, wherein the curing agent component used is a hydrazide compound such as adipic acid dihydrazide, sebacic acid dihydrazide, isophthalic acid dihydrazide and Amicure VDH (manufactured by Ajinomoto Fine-chemical company, inc.), which reacts not only with an epoxy group under heating but also with a (meth) acryloyl group. Among the above hydrazides, the hydrazide compound reacts not only with an epoxy group under heating but also with a (meth) acryloyl group, and these compounds cause a change in viscosity and the like with time at room temperature, which makes the storage stability of the product poor.
Disclosure of Invention
The invention aims to provide a sealing frame adhesive of a liquid crystal panel, wherein a curing agent adduct reduces primary amine in a curing agent compared with an original curing agent, avoids the occurrence of sealing adhesive reaction such as Schiff base reaction and Michael addition reaction, avoids the deterioration of resin storage stability, and ensures that the storage stability and the curing property of the frame adhesive are excellent.
The technical purpose of the invention is realized by the following technical scheme: a sealing frame adhesive of a liquid crystal panel comprises a curable resin, a curing agent, a filler and a photoinitiator, wherein the curing agent is an adduct consisting of a hydrazide compound (A) and an epoxy compound (B) or an acid or anhydride compound (C), and the curing agent has the following structural formula:
preferably, the hydrazide compound (A) comprises one or more of adipic Acid Dihydrazide (ADH), sebacic acid dihydrazide (SDH), isophthalic acid dihydrazide (IDH), dodecanedicarboxylic acid dihydrazide (DDH), salicyloyl hydrazine (SAH), 7, 11-octadecadienyl-1, 18-dicarbonyl dihydrazide (UDH), 1, 3-bis (hydrazinocarboethyl) 5-isopropylhydantoin (VDH), octadecane-1, 18-dicarboxylic acid dihydrazide (LDH).
Preferably, the epoxy compound (B) comprises one or more of resorcinol diglycidyl ether, 1, 4-butanediol glycidyl ether and cester glycidyl ether, alkylene glycidyl ether, butyl glycidyl ether, ethylene glycol diglycidyl ether, phenyl glycidyl ether, polypropylene glycol diglycidyl ether, C12-14 fatty glycidyl ether, benzyl glycidyl ether, 1, 6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether and allyl glycidyl ether.
Preferably, the acid or acid anhydride compound (C) comprises one or more of hexahydrophthalic acid, benzoic acid, pyromellitic dianhydride, phthalic anhydride, methyltetrahydrophthalic anhydride, trimellitic anhydride, tetrabromophthalic anhydride, maleic anhydride, 70# anhydride, 647# anhydride, 308 elaeostearic anhydride.
Preferably, the curable resin includes epoxy acrylate UVACURE 1561.
Preferably, the filler comprises one or more mixtures of talc, asbestos, silica, diatomaceous earth, smectite (smectite), bentonite, calcium carbonate, magnesium carbonate, alumina, montmorillonite, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, magnesium hydroxide, aluminum hydroxide, glass beads, silicon nitride, barium sulfate, gypsum, calcium silicate, sericite, activated clay, aluminum nitride, polyester microparticles, polyurethane microparticles, vinyl polymer microparticles, acrylic polymer microparticles.
The invention also aims to provide a preparation method of the sealant for liquid crystal packaging, which comprises the following steps:
firstly, adding hydrazide compound (A) and toluene into a three-neck flask with a stirrer, a dropping funnel and a condenser, and stirring and dissolving at 80-100 ℃; cooling to 25 ℃ and dripping a mixed solution consisting of an epoxy compound (B), an acid or anhydride compound (C) and toluene within 1 h; keeping the temperature for 1h, detecting the epoxy value, distilling the solvent toluene under reduced pressure when the epoxy value is reduced to 0.02eq/100g, and carrying out filter pressing by a filter press to obtain a curing agent, wherein the structural formula of the curing agent obtained by the addition reaction of part of primary amine of a hydrazide compound (A) and an epoxy compound (B) is (a), and the reaction equation is (1); the structural formula of the curing agent obtained by the addition reaction of all primary amines of the hydrazide compound (A) and the epoxy compound (B) is (B), and the reaction formulas are respectively (2); the structural formula of the curing agent obtained by addition reaction of partial primary amine of the hydrazide compound (A) and the acid or anhydride compound (C) is (d), and the reaction formulas are respectively (3); the structural formula of the curing agent obtained by the addition reaction of all primary amines of the hydrazide compound (A) and the acid or anhydride compound (C) is (e), and the reaction formulas are (4);
secondly, adding a filler and a photoinitiator into the curable resin in a double-planet stirrer, stirring for 20 minutes in vacuum, adding the curing agent obtained in the first step after the temperature is reduced to 25 ℃, and stirring for 20 minutes in vacuum again; and finally, obtaining the frame glue product through a three-roller grinding machine and a filter press.
In conclusion, the invention achieves the following beneficial effects: compared with the original curing agent, the curing agent adduct reduces primary amine in the curing agent, avoids the deterioration of the storage stability of the resin caused by Schiff base reaction of the sealant, and has excellent storage stability and curing property.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all 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.
The present invention will be described in further detail below.
A sealing frame adhesive of a liquid crystal panel comprises a curable resin, a curing agent, a filler and a photoinitiator, wherein the curing agent is an adduct composed of a hydrazide compound (A) and an epoxy compound (B) or an acid or anhydride compound (C), and the structural formula of the curing agent is as follows:
wherein R is 1 ～R 3 Is any group such as alkane, alkene, aromatic hydrocarbon, heterocycle, etc.
The preparation method of the sealing frame adhesive of the liquid crystal panel comprises the following steps:
firstly, adding a hydrazide compound (A) and toluene into a three-neck flask provided with a stirrer, a dropping funnel and a condenser, and stirring and dissolving at 80-100 ℃; cooling to 25 ℃ within 1h, and dropwise adding a mixed solution consisting of an epoxy compound (B), an acid or anhydride compound (C) and toluene; keeping the temperature for 1h, detecting the epoxy value, distilling the solvent toluene under reduced pressure when the epoxy value is reduced to 0.02eq/100g, and carrying out filter pressing by a filter press to obtain a curing agent, wherein the structural formula of the curing agent obtained by the addition reaction of part of primary amine of a hydrazide compound (A) and an epoxy compound (B) is (a), and the reaction equation is (1); the structural formula of the curing agent obtained by the addition reaction of all primary amines of the hydrazide compound (A) and the epoxy compound (B) is (B), and the reaction formulas are respectively (2); the structural formula of the curing agent obtained by addition reaction of partial primary amine of the hydrazide compound (A) and the acid or anhydride compound (C) is (d), and the reaction formulas are respectively (3); the structural formula of the curing agent obtained by addition reaction of all primary amines of the hydrazide compound (A) and the acid or anhydride compound (C) is (e), and the reaction formulas are respectively (4);
secondly, adding a filler and a photoinitiator into the curable resin in a double-planet stirrer; stirring in vacuum for 20 minutes, adding the curing agent obtained in the first step after the temperature is reduced to 25 ℃, and stirring in vacuum for 20 minutes again; and finally, obtaining a frame glue product through a three-roller grinding machine and a filter press.
1-10 parts of curing agent is prepared by the method of the first step, and comprises the following steps:
curing agent 1
17g of ADH and 50g of toluene were charged in a three-necked flask equipped with a stirrer, a dropping funnel and a condenser, and dissolved by stirring at 80 to 100 ℃. The temperature is reduced to 25 ℃, and a mixed solution of 21g of resorcinol diglycidyl ether and 50g of toluene is added dropwise within 1h. Keeping the temperature for 1h, detecting the epoxy value, distilling the solvent toluene under reduced pressure when the epoxy value is reduced to 0.1eq/100g, and performing pressure filtration by a filter press to obtain an adduct compound curing agent slurry curing agent 1, wherein the reaction equation is shown as follows.
Curing agent 2
34g of ADH and 50g of toluene were charged in a three-necked flask equipped with a stirrer, a dropping funnel and a condenser, and dissolved by stirring at 80 to 100 ℃. The temperature is reduced to 25 ℃, and a mixed solution of 21g of resorcinol diglycidyl ether and 50g of toluene is added dropwise within 1h. Keeping the temperature for 1h, detecting the epoxy value, distilling the solvent toluene under reduced pressure when the epoxy value is reduced to 0.02eq/100g, and performing pressure filtration by a filter press to obtain an adduct compound curing agent slurry curing agent 2, wherein the reaction equation is shown as follows.
Curing agent 3
17g of ADH and 50g of toluene were charged in a three-necked flask equipped with a stirrer, a dropping funnel and a condenser, and dissolved by stirring at 80 to 100 ℃. The temperature is reduced to 25 ℃, and a mixed solution of 15g of phenol glycidyl ether and 50g of toluene is added dropwise within 1h. Keeping the temperature for 1h, detecting the epoxy value, distilling the solvent toluene under reduced pressure when the epoxy value is reduced to 0.02eq/100g, and performing pressure filtration by a filter press to obtain an adduct compound curing agent slurry curing agent 3, wherein the reaction equation is shown as follows.
Curing agent 4
17g of ADH and 50g of toluene were charged into a three-necked flask equipped with a stirrer, a dropping funnel and a condenser, and dissolved by stirring at 80 to 100 ℃. Cooling to 25 deg.c and dropping mixed solution of 18g1, 4-butanediol diglycidyl ether and 50g toluene in 1 hr. Keeping the temperature for 1h, detecting the epoxy value, distilling the solvent toluene under reduced pressure when the epoxy value is reduced to 0.07eq/100g, and performing pressure filtration by a filter press to obtain an adduct compound curing agent slurry curing agent 4, wherein the reaction equation is shown as follows.
Curing agent 5
17g of ADH and 50g of toluene were charged in a three-necked flask equipped with a stirrer, a dropping funnel and a condenser, and dissolved by stirring at 80 to 100 ℃. The temperature was reduced to 25 ℃ and a mixed solution of 9g1, 4-butanediol diglycidyl ether and 50g toluene was added dropwise over 1 hour. Keeping the temperature for 1h, detecting the epoxy value, distilling the solvent toluene under reduced pressure when the epoxy value is reduced to 0.02eq/100g, and performing pressure filtration by a filter press to obtain an adduct compound curing agent slurry curing agent 5, wherein the reaction equation is shown as follows.
Curing agent 6
17g of ADH and 50g of toluene were charged in a three-necked flask equipped with a stirrer, a dropping funnel and a condenser, and dissolved by stirring at 80 to 100 ℃. The temperature is reduced to 25 ℃, and a mixed solution consisting of 15g of hexahydrophthalic acid and 50g of toluene is added dropwise within 1 hour. And (3) keeping the temperature for 1h, detecting an amine value, distilling the solvent toluene under reduced pressure when the amine value is reduced to 600mgKOH/g, and performing pressure filtration by using a filter press to obtain an adduct compound curing agent slurry curing agent 6, wherein the reaction equation is shown as follows.
Curing agent 7
21g of SDH and 50g of toluene were charged into a three-necked flask equipped with a stirrer, a dropping funnel and a condenser, and dissolved by stirring at 80 to 100 ℃. The temperature is reduced to 25 ℃, and a mixed solution consisting of 15g of hexahydrophthalic acid and 50g of toluene is added dropwise within 1 hour. And (3) keeping the temperature for 1h, detecting an amine value, distilling the solvent toluene under reduced pressure when the amine value is reduced to 500mgKOH/g, and performing pressure filtration by using a filter press to obtain an adduct compound curing agent slurry curing agent 7, wherein the reaction equation is shown as follows.
Curing agent 8
17g of ADH and 50g of toluene were charged in a three-necked flask equipped with a stirrer, a dropping funnel and a condenser, and dissolved by stirring at 80 to 100 ℃. The temperature is reduced to 25 ℃, and a mixed solution consisting of 11g of benzoic acid and 50g of toluene is added dropwise within 1h. And (3) keeping the temperature for 1h, detecting an amine value, distilling the solvent toluene under reduced pressure when the amine value is reduced to 700mgKOH/g, and performing pressure filtration by using a filter press to obtain an adduct compound curing agent slurry curing agent 8, wherein the reaction equation is shown as follows.
Curing agent 9
21g of SDH and 50g of toluene were put in a three-necked flask equipped with a stirrer, a dropping funnel and a condenser, and dissolved by stirring at 80 to 100 ℃. The temperature is reduced to 25 ℃, and a mixed solution consisting of 11g of benzoic acid and 50g of toluene is added dropwise within 1h. And (3) keeping the temperature for 1h, detecting the amine value, distilling the solvent toluene under reduced pressure when the amine value is reduced to 600mgKOH/g, and performing pressure filtration by using a filter press to obtain an adduct compound curing agent slurry curing agent 9, wherein the reaction equation is shown as follows.
Curing agent 10
17g of ADH and 50g of toluene were charged in a three-necked flask equipped with a stirrer, a dropping funnel and a condenser, and dissolved by stirring at 80 to 100 ℃. The temperature is reduced to 25 ℃, and a mixed solution of 14g of the glycidyl ether and 50g of toluene is added dropwise within 1h. Keeping the temperature for 1h, detecting the epoxy value, distilling the solvent toluene under reduced pressure when the epoxy value is reduced to 0.02eq/100g, and performing pressure filtration by a filter press to obtain the adduct compound curing agent slurry curing agent 10, wherein the reaction equation is shown as follows.
Example 1
In a double planetary mixer, 100g of epoxy acrylate UVACURE 1561 was added 1g of silica filler, 1g of photoinitiator Iracure651. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃, 28.6g of the above hydrazide adduct compound 1 was added and the mixture was again stirred under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Example 2
In a double planetary mixer, 100g of epoxy acrylate UVACURE 1561 was added 1g of silica filler, 1g of photoinitiator Iracure651. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃ 10.3g of the above hydrazide adduct 2 was added, and the mixture was again stirred under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Example 3
In a double planetary mixer, 100g of epoxy acrylate UVACURE 1561 was added 1g of silica filler, 1g of photoinitiator Iracure651. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃, 24.1g of the above hydrazide adduct 3 was added and the mixture was again stirred under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Example 4
In a double planetary mixer, 100g of epoxy acrylate UVACURE 1561 was added 1g of silica filler, 1g of photoinitiator Iracure651. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃, 26.4g of the above hydrazide adduct 4 was added and the mixture was again stirred under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Example 5
In a double planetary mixer, 100g of epoxy acrylate UVACURE 1561 was added 1g of silica filler, 1g of photoinitiator Iracure651. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃, 9.8g of the above hydrazide adduct 5 was added and the mixture was again stirred under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Example 6
In a double planetary mixer, 100g of epoxy acrylate UVACURE 1561 was added 1g of silica filler, 1g of photoinitiator Iracure651. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃, 24.1g of the above hydrazide adduct compound 6 was added and the mixture was again stirred under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Example 7
In a double planetary mixer, 100g of epoxy acrylate UVACURE 1561 was added 1g of silica filler, 1g of photoinitiator Iracure651. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃, 29.0g of the above hydrazide adduct 7 was added and the mixture was again stirred under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Example 8
In a double planetary mixer, 100g of epoxy acrylate UVACURE 1561 was added 1g of silica filler, 1g of photoinitiator Iracure651. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃, 21.1g of the above hydrazide adduct 8 was added and the mixture was again stirred under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Example 9
In a double-planet stirring instrument, 1g of silicon dioxide filler and 1g of photoinitiator Iracure651 are added into 100g of epoxy acrylate UVACURE 1561. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃ 25.8g of the above hydrazide adduct 9 were added, the mixture was again stirred under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Example 10
In a double-planet stirring instrument, 1g of silicon dioxide filler and 1g of photoinitiator Iracure651 are added into 100g of epoxy acrylate UVACURE 1561. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃, 7.8g of the above hydrazide adduct 10 was added and the mixture was again stirred under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Comparative example 1
In a double planetary mixer, 100g of epoxy acrylate UVACURE 1561 was added 1g of silica filler, 1g of photoinitiator Iracure651. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 ℃ 9.6g of ADH were added, stirring again under vacuum for 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Comparative example 2
In a double-planet stirring instrument, 1g of silicon dioxide filler and 1g of photoinitiator Iracure651 are added into 100g of epoxy acrylate UVACURE 1561. After stirring under vacuum for 20 minutes and waiting for the temperature to drop to 25 deg.C, 16.5g of VDH was added and stirring under vacuum for another 20 minutes. And finally, grinding by a three-roller grinder and performing filter press to obtain the product.
Test method
Storage stability: the viscosity of the resin at 2.5rpm measured on a cone and plate viscometer with the resin thermostatted to 25 ℃ is recorded as the initial viscosity. The resin is placed in a constant temperature box at 25 ℃ for 1 week, the viscosity of the conical plate is measured again, and the viscosity change rate of one week is calculated. The viscosity change was more than 50000cps and marked as X, less than 50000cps and more than 3000cps and marked as X, less than 30000cps and marked as excellent.
Curing property:
mixing resin at 1% spacer, coating in the middle of glass substrate, bonding, and collecting light with wavelength of 365nm to 3000mJ/cm 2 The mixture is put into a constant temperature box and is kept at the temperature of 120 ℃ for 1 hour. Taking out the glue, and measuring the curing degree by an infrared spectrometer, wherein the curing degree is 915cm -1 Is an epoxy group, 830cm -1 As a reference peak. X was measured at a level of less than 80%, O was measured at a level of less than 90% and more than 80%, and E was measured at a level of more than 90%.
As shown in Table 1 below, the curing agents of examples 1 to 10 were excellent in storage stability and curability.
TABLE 1
The above description is only a preferred embodiment of the present invention, and the protection scope of the present invention is not limited to the above embodiments, and all technical solutions belonging to the idea of the present invention belong to the protection scope of the present invention. It should be noted that modifications and adaptations to those skilled in the art without departing from the principles of the present invention should also be considered as within the scope of the present invention.
Claims (7)
1. The frame sealing glue of the liquid crystal panel is characterized by comprising curable resin, a curing agent, a filler and a photoinitiator, wherein the curing agent is an adduct composed of a hydrazide compound (A) and an epoxy compound (B) or an acid or anhydride compound (C), and the structural formula of the curing agent is as follows:
2. a sealant for a liquid crystal panel according to claim 1, wherein: the hydrazide compound (A) comprises one or more of adipic Acid Dihydrazide (ADH), sebacic acid dihydrazide (SDH), isophthalic acid dihydrazide (IDH), dodecane dicarboxylic acid dihydrazide (DDH), salicyloyl hydrazide (SAH), 7, 11-octadecadienyl-1, 18-dicarbonyl dihydrazide (UDH), 1, 3-bis (hydrazinocarboethyl) 5-isopropyl hydantoin (VDH), octadecane-1, 18-dicarboxylic acid dihydrazide (LDH).
3. A sealant for a liquid crystal panel according to claim 1, wherein: the epoxy compound (B) comprises one or more of resorcinol diglycidyl ether, 1, 4-butanediol glycidyl ether and cester glycidyl ether, alkylene glycidyl ether, butyl glycidyl ether, ethylene glycol diglycidyl ether, phenyl glycidyl ether, polypropylene glycol diglycidyl ether, C12-14 fatty glycidyl ether, benzyl glycidyl ether, 1, 6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether and allyl glycidyl ether.
4. A sealant for a liquid crystal panel according to claim 1, wherein: the acid or acid anhydride compound (C) comprises one or more of hexahydrophthalic acid, benzoic acid, pyromellitic dianhydride, phthalic anhydride, methyltetrahydrophthalic anhydride, trimellitic anhydride, tetrabromophthalic anhydride, maleic anhydride, 70# anhydride, 647# anhydride and 308 elaeostearic anhydride.
5. A sealant for a liquid crystal panel according to claim 1, wherein: the curable resin comprises epoxy acrylate UVACURE 1561.
6. A sealant for a liquid crystal panel according to claim 1, wherein: the filler comprises one or more of talc, asbestos, silica, diatomaceous earth, smectite (smectite), bentonite, calcium carbonate, magnesium carbonate, alumina, montmorillonite, zinc oxide, iron oxide, magnesium oxide, tin oxide, titanium oxide, magnesium hydroxide, aluminum hydroxide, glass beads, silicon nitride, barium sulfate, gypsum, calcium silicate, sericite, activated clay, aluminum nitride, polyester microparticles, polyurethane microparticles, vinyl polymer microparticles, acrylic polymer microparticles.
7. A method for manufacturing a sealant for a liquid crystal panel according to claim 1, comprising the steps of:
firstly, adding a hydrazide compound (A) and toluene into a three-neck flask provided with a stirrer, a dropping funnel and a condenser, and stirring and dissolving at 80-100 ℃; cooling to 25 ℃ within 1h, and dropwise adding a mixed solution consisting of an epoxy compound (B), an acid or anhydride compound (C) and toluene; keeping the temperature for 1h, detecting the epoxy value, distilling the solvent toluene under reduced pressure when the epoxy value is reduced to 0.02eq/100g, and carrying out filter pressing by a filter press to obtain a curing agent, wherein the structural formula of the curing agent obtained by the addition reaction of part of primary amine of a hydrazide compound (A) and an epoxy compound (B) is (a), and the reaction equation is (1); the structural formula of the curing agent obtained by the addition reaction of all primary amines of the hydrazide compound (A) and the epoxy compound (B) is (B), and the reaction formulas are respectively (2); the structural formula of the curing agent obtained by addition reaction of partial primary amine of the hydrazide compound (A) and the acid or anhydride compound (C) is (d), and the reaction formulas are respectively (3); the structural formula of the curing agent obtained by addition reaction of all primary amines of the hydrazide compound (A) and the acid or anhydride compound (C) is (e), and the reaction formulas are respectively (4);
secondly, adding a filler and a photoinitiator into the curable resin in a double-planet stirrer, stirring for 20 minutes in vacuum, adding the curing agent obtained in the first step after the temperature is reduced to 25 ℃, and stirring for 20 minutes in vacuum again; and finally, obtaining a frame glue product through a three-roller grinding machine and a filter press.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0933932A (en) * | 1995-07-20 | 1997-02-07 | Sumitomo Bakelite Co Ltd | Sealing material composition for liquid crystal display element and liquid crystal display element formed by using the same |
| JPH11147935A (en) * | 1997-11-18 | 1999-06-02 | Ajinomoto Co Inc | Adhesive composition |
| CN1711300A (en) * | 2002-11-06 | 2005-12-21 | 日本化药株式会社 | Sealing material for liquid crystal and liquid crystal display cell using same |
| CN101585929A (en) * | 2009-06-25 | 2009-11-25 | 嘉兴荣泰雷帕司绝缘材料有限公司 | Hydrazide latency improving curing agent and preparation method thereof |
| CN109957209A (en) * | 2017-12-25 | 2019-07-02 | 北京科化新材料科技有限公司 | Composition epoxy resin, naval stores and preparation method thereof and resin |
| CN112080239A (en) * | 2020-09-10 | 2020-12-15 | 苏州润邦半导体材料科技有限公司 | Sealant composition and preparation method and application thereof |
-
2021
- 2021-12-24 CN CN202111596101.6A patent/CN114384727A/en not_active Withdrawn
-
2022
- 2022-11-28 CN CN202211498846.3A patent/CN115755469A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0933932A (en) * | 1995-07-20 | 1997-02-07 | Sumitomo Bakelite Co Ltd | Sealing material composition for liquid crystal display element and liquid crystal display element formed by using the same |
| JPH11147935A (en) * | 1997-11-18 | 1999-06-02 | Ajinomoto Co Inc | Adhesive composition |
| CN1711300A (en) * | 2002-11-06 | 2005-12-21 | 日本化药株式会社 | Sealing material for liquid crystal and liquid crystal display cell using same |
| CN101585929A (en) * | 2009-06-25 | 2009-11-25 | 嘉兴荣泰雷帕司绝缘材料有限公司 | Hydrazide latency improving curing agent and preparation method thereof |
| CN109957209A (en) * | 2017-12-25 | 2019-07-02 | 北京科化新材料科技有限公司 | Composition epoxy resin, naval stores and preparation method thereof and resin |
| CN112080239A (en) * | 2020-09-10 | 2020-12-15 | 苏州润邦半导体材料科技有限公司 | Sealant composition and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| 张宝华 等: "树枝状多酰肼固化剂的制备与性能", 高分子材料科学与工程, vol. 29, no. 4, pages 125 - 128 * |
| 陈连喜 等: "环氧树脂潜伏性固化剂研究进展", 化工新型材料, vol. 32, no. 7, pages 29 - 32 * |
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