CN113493645A - Ultraviolet-curing organic silicon release agent and preparation method thereof - Google Patents
Ultraviolet-curing organic silicon release agent and preparation method thereof Download PDFInfo
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- CN113493645A CN113493645A CN202010193993.4A CN202010193993A CN113493645A CN 113493645 A CN113493645 A CN 113493645A CN 202010193993 A CN202010193993 A CN 202010193993A CN 113493645 A CN113493645 A CN 113493645A
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 63
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 33
- 239000010703 silicon Substances 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000001723 curing Methods 0.000 claims abstract description 54
- SOGFHWHHBILCSX-UHFFFAOYSA-J prop-2-enoate silicon(4+) Chemical compound [Si+4].[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C.[O-]C(=O)C=C SOGFHWHHBILCSX-UHFFFAOYSA-J 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- -1 polydimethylsiloxane Polymers 0.000 claims abstract description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims abstract description 21
- 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 abstract description 20
- 239000004205 dimethyl polysiloxane Substances 0.000 claims abstract description 20
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003085 diluting agent Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 11
- 239000003112 inhibitor Substances 0.000 claims abstract description 9
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 9
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 229920001296 polysiloxane Polymers 0.000 claims description 22
- 239000011248 coating agent Substances 0.000 claims description 20
- 238000000576 coating method Methods 0.000 claims description 20
- 239000000123 paper Substances 0.000 claims description 9
- 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 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 4
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- 239000002344 surface layer Substances 0.000 claims description 3
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims description 2
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 claims description 2
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims description 2
- BDAHDQGVJHDLHQ-UHFFFAOYSA-N [2-(1-hydroxycyclohexyl)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C1(O)CCCCC1 BDAHDQGVJHDLHQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000001680 brushing effect Effects 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 claims description 2
- 238000005507 spraying Methods 0.000 claims description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 3
- 238000000016 photochemical curing Methods 0.000 abstract description 3
- 238000003915 air pollution Methods 0.000 abstract 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 15
- 229920002799 BoPET Polymers 0.000 description 14
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- 239000006082 mold release agent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000003848 UV Light-Curing Methods 0.000 description 6
- 239000002390 adhesive tape Substances 0.000 description 6
- 238000007790 scraping Methods 0.000 description 6
- 238000011056 performance test Methods 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000010561 standard procedure Methods 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000001029 thermal curing Methods 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 101710137710 Thioesterase 1/protease 1/lysophospholipase L1 Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013475 authorization Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- 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
- 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/20—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for coatings strippable as coherent films, e.g. temporary coatings strippable as coherent films
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/20—Air quality improvement or preservation, e.g. vehicle emission control or emission reduction by using catalytic converters
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
Abstract
The invention discloses an ultraviolet curing organic silicon release agent and a preparation method thereof, wherein the ultraviolet curing organic silicon release agent is prepared from the following raw materials in parts by weight: 100 parts of organic silicon acrylate oligomer, 10-30 parts of reactive diluent and 1-4 parts of photoinitiator; the organic silicon acrylate oligomer is prepared by the following method: uniformly mixing hydrogen-terminated polydimethylsiloxane, pentaerythritol triacrylate or dipentaerythritol pentaacrylate, a catalyst, a polymerization inhibitor and a solvent, heating for reaction, and performing rotary evaporation to remove the solvent after the reaction is finished to obtain the organic silicon acrylate oligomer. The ultraviolet curing organosilicon release agent can realize photocuring in air and can generate good release effect on different base materials because the main organosilicon acrylate of the ultraviolet curing organosilicon release agent has a large amount of acrylate groups. The formula does not contain volatile solvent, does not cause air pollution, and is an environment-friendly release agent.
Description
Technical Field
The invention belongs to the field of chemical industry, relates to a coating, and particularly relates to an ultraviolet curing organic silicon release agent and a preparation method thereof.
Background
The release agent is also called as an isolating agent or an anti-sticking agent, and is a matching material required for preparing an anti-sticking layer of a pressure-sensitive adhesive, an isolating layer of a self-adhesive label and packaging materials of other various adhesive substances. Because the organosilicon material has the advantages of lower surface energy, excellent aging resistance, low toxicity, wide temperature application range and the like, the prior anti-sticking release agent products are mostly prepared from the organosilicon material.
The silicone release agent used in the early days mostly adopts vinyl silicone as resin, hydrogen-containing silicone oil as a cross-linking agent and metal platinum as a catalyst, and is cured at high temperature. This process is energy intensive due to the high temperatures required for curing and limits its use on some heat sensitive substrates (e.g., paper, plastics).
The ultraviolet light curing organic silicon release agent is an organic silicon acrylate oligomer which takes polysiloxane as a main chain and takes an end group as an acrylate group as a photosensitive functional group, wherein a polysiloxane chain segment endows low surface performance, and the acrylate group has photocuring performance. Because the ultraviolet curing organic silicon release agent is cured by ultraviolet irradiation, the ultraviolet curing organic silicon release agent can be cured quickly at normal temperature, saves energy, and can be applied to paper, plastic and other base materials which are not suitable for thermal curing.
Chinese patent authorization text CN 105131779B discloses an ultraviolet curing organic silicon release agent and a preparation method thereof, the curing temperature of the organic silicon release agent is low, the obtained coating is transparent and colorless, and good release effect can be generated on various base materials. However, the method needs to add a large amount of solvent, and the solvent has a strong smell and is very easy to volatilize into the air, thereby causing serious harm and pollution to human bodies and the environment. Chinese patent publication CN 107236130A discloses an ultraviolet light curing fluorosilicone mold release and a preparation method thereof, the mold release prepared by introducing fluorine has extremely low mold release force, but fluorine is not easy to metabolize by human bodies, and the human health is easily damaged, so that the popularization and the application of the mold release are limited.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention mainly aims to provide an ultraviolet curing organic silicon release agent. The ultraviolet curing organic silicon release agent can be directly cured by ultraviolet irradiation at room temperature in air, does not contain a solvent or fluorine, is an environment-friendly and nontoxic release agent, and accords with the concept of environmental protection.
The invention also aims to provide a preparation method of the ultraviolet curing organic silicon release agent.
The purpose of the invention is realized by the following scheme:
an ultraviolet curing organic silicon release agent is prepared from the following raw materials in parts by weight:
100 parts of organic silicon acrylate oligomer, namely,
10-30 parts of an active diluent,
1-4 parts of a photoinitiator.
Preferably, the ultraviolet curing organosilicon release agent is prepared from the following raw materials in parts by weight:
100 parts of organic silicon acrylate oligomer, namely,
20 parts of a reactive diluent, namely 20 parts of a reactive diluent,
4 parts of a photoinitiator.
The reactive diluent refers to a reactive monomer with at least one acrylate group, and includes but is not limited to at least one of butyl acrylate, isooctyl acrylate, isodecyl acrylate, lauryl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, 1, 4-butanediol diacrylate, 1, 6-hexanediol diacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate;
the photoinitiator is a compound capable of generating free radicals under ultraviolet irradiation, and is at least one of 2-hydroxy-2-methyl propiophenone (Darocur1173), 1-hydroxy-cyclohexyl benzophenone (Darocur184), 2-methyl 1- (4-methylthiophenyl) -2-morpholinoacetone (Irgacure907), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone (Irgacure369) and Benzophenone (BP);
the organic silicon acrylate oligomer is a reaction product of pentaerythritol triacrylate or dipentaerythritol pentaacrylate and hydrogen-terminated polydimethylsiloxane, and the specific structural formula is as follows:
wherein n is 25 to 80, R is
One kind of (1).
The organic silicon acrylate oligomer is prepared by the following method: uniformly mixing hydrogen-terminated polydimethylsiloxane, pentaerythritol triacrylate or dipentaerythritol pentaacrylate, a catalyst, a polymerization inhibitor and a solvent, heating for reaction, and performing rotary evaporation to remove the solvent after the reaction is finished to obtain the organic silicon acrylate oligomer.
In the preparation of the silicone acrylate oligomer, the hydrogen-terminated polydimethylsiloxane was purchased from wujiang reagent and was of the formula H (CH)3)2SiO[(CH3)2SiO]nSi(CH3)2H, wherein Mn is 2000-.
In the preparation process of the organic silicon acrylate oligomer, the catalyst is at least one of Karstedt catalyst or Spierer catalyst, the polymerization inhibitor is at least one of hydroquinone, p-methoxyphenol, o-methyl hydroquinone, p-tert-butyl catechol and p-benzoquinone, and the solvent is at least one of toluene and isopropanol;
in the preparation process of the organic silicon acrylate oligomer, the temperature rise reaction refers to reaction for 4-8 hours when the temperature is raised to 80-110 ℃; preferably, the temperature-rising reaction is a reaction for 6 hours at a temperature of 100 ℃.
The hydrogen-terminated polydimethylsiloxane, pentaerythritol triacrylate or dipentaerythritol pentaacrylate, a catalyst, a polymerization inhibitor and a solvent are used in the following amounts: the mass ratio of the hydrogen-terminated polydimethylsiloxane to the acrylate (pentaerythritol triacrylate or dipentaerythritol pentaacrylate) is 1:2 to 1:2.5, and the optimal value is 1: 2; the catalyst concentration is 4-20ppm (ppm represents the mass of the catalyst in million parts of the mass of the reactant of the whole reaction system, wherein the reactant comprises hydrogen-terminated polydimethylsiloxane and pentaerythritol triacrylate or dipentaerythritol pentaacrylate), and the optimal value is 10 ppm; the mass of the polymerization inhibitor is 0.01-0.1 percent of the total weight of the reactants, and the optimal value is 0.1 percent; the mass of the solvent is 50-150% of the total weight of the reactants, and the optimal value is 50%.
The preparation method of the ultraviolet curing organic silicon release agent comprises the following steps: and weighing the organic silicon acrylate oligomer, the reactive diluent and the photoinitiator according to the proportion, and mixing and stirring uniformly to obtain the ultraviolet curing organic silicon release agent.
The use method of the ultraviolet curing organic silicon release agent comprises the following steps: the coating can be coated on the outer surface layers of metal, glass, paper, plastic and the like by adopting the modes of spraying, brushing and the like, and is cured into a mold release agent coating under the irradiation of ultraviolet light.
The mechanism of the invention is as follows:
the invention makes pentaerythritol triacrylate or dipentaerythritol pentaacrylate with photocuring ability react with hydrogen-terminated polydimethylsiloxane to obtain organosilicon acrylate oligomer with photosensitivity, and then reactive diluent and photoinitiator are added to be cured at room temperature under the irradiation of ultraviolet light, thereby avoiding the high temperature problem in the thermocuring process and saving energy.
Compared with the prior art, the invention has the following advantages and beneficial effects:
the ultraviolet curing organic silicon release agent provided by the invention is suitable for being used as a release agent coating on the outer surface of metal, glass, paper, plastic and the like, and has a wider application range compared with an organic silicon release agent needing high-temperature curing.
Compared with the prior art, the invention has remarkable technical progress. The invention uses hydrogen-terminated polydimethylsiloxane to graft a plurality of acrylate groups to be converted into polymerizable organic silicon acrylate oligomer, and the oligomer has a large amount of light-curable acrylate groups, so that the curing of the organic silicon release agent can be realized at room temperature in air, and the coating obtained after the curing can generate good release effect, has low stripping force, strong water resistance and wide application range, and can be applied to outer surface layers of metal, glass, paper, plastic and the like.
Drawings
FIG. 1 is an IR spectrum of the silicone acrylate oligomer obtained in example 2.
FIG. 2 is an IR spectrum of the silicone acrylate oligomer obtained in example 5.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the embodiments of the present invention are not limited thereto. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The hydrogen-terminated polydimethylsiloxanes described in the examples were obtained from wujiang reagent.
The preparation method of the Spiecer catalyst used in the examples comprises the following steps: 0.1328g of chloroplatinic acid hexahydrate and 50.00g of isopropanol were weighed out accurately, stirred in a beaker for 1 hour, and then stored in a 100mL brown bottle.
In the examples, the method for testing the release force at normal temperature and the method for testing the residual adhesion rate of the release agent are respectively as follows:
a method for testing the normal-temperature release force of a release agent comprises the following steps: the TESA 7475 adhesive tape is stuck on the tested silicon-coated release paper according to the standard method, cut into strips according to the shape of the adhesive tape, and then pressed back and forth three times by a 2kg rubber compression roller. The treated adhesive tape was used at 20g/cm2The standard stainless steel strip is pressed for 20 hours at normal temperature, and is placed for 4 hours at room temperature, and then a release force tester is used for testing, wherein the stretching speed is 30cm/min, and the tensile force at the stretching angle of 180 degrees is the normal-temperature release force.
Secondly, a residual adhesion rate test method of the release agent:
(1) the Nitto31B tape was attached to the silicon-coated release paper to be tested by a standard method, cut into long strips in the shape of the tape, and then pressed back and forth three times with a 2kg rubber press roll. The treated adhesive tape was used at 20g/cm2The standard stainless steel strip was placed in an oven at 70 ℃ under internal pressure for 20 hours, and then taken out and left to stand for 1 hour.
(2) The adhesive tape of Nitto31B was peeled from the release paper and adhered to a clean PET film by a standard method, after 1.5 hours, the film was tested by a release force tester, the tensile force was measured at a tensile speed of 30cm/min and at a tensile angle of 180 degrees, and the obtained release force value was recorded. After repeating the experiment for a plurality of times, the average value of the release force values is calculated and recorded as F2。
(3) Directly sticking the adhesive tape Nitto31B on a clean PET film according to a standard method, testing by using a release force tester after 1.5 hours, wherein the tensile force is measured at the tensile speed of 30cm/min and the tensile angle of 180 degrees, and recording the obtained release force value. After repeating the experiment for a plurality of times, the average value of the release force values is calculated and recorded as F1。
(4) Residual adhesion rate ═ F2/F1×100％。
Example 1
An ultraviolet curing organosilicon release agent is prepared from the following raw materials in parts by weight: 100 parts of organic silicon acrylate oligomer, 20 parts of pentaerythritol triacrylate and 4 parts of Darocur1173 (photoinitiator).
The preparation method of the organic silicon acrylate oligomer comprises the following steps: 20.00g of hydrogen-terminated polydimethylsiloxane (Mn: 2000, available from Guangdong Ningjiang chemical Co., Ltd.), 10.49g of dipentaerythritol pentaacrylate (the mass ratio of the substances is 1:2), 0.30g of Spiecer catalyst, 0.03g of p-methoxyphenol and 15.25g of toluene were charged into a reaction vessel, stirred uniformly, heated to 100 ℃ for reaction for 6 hours, and after the reaction was completed, the solvent was removed by rotary evaporation to obtain an organosilicon acrylate oligomer.
And stirring and uniformly mixing 100 parts of the obtained organic silicon acrylate oligomer, 20 parts of pentaerythritol triacrylate and 4 parts of Darocur1173 (photoinitiator) to obtain the ultraviolet curing organic silicon mold release agent.
And (3) coating the ultraviolet curing organosilicon release agent on a PET film by using a 2-micron wire bar in a scraping manner, then putting the coated PET film into a CH-1022000W UV curing box, and curing for 30 seconds to obtain the cured organosilicon release coating. The results of the release property test are shown in table 1 below. Numbers 1, 2, 3 indicate that three replicates were made and then averaged.
Table 1 release performance test results of the uv-curable silicone release agent prepared in example 1
| Serial number | Normal temperature release force (g/25mm) | Residual adhesion (%) |
| 1 | 15.78 | 89.31 |
| 2 | 16.38 | 91.53 |
| 3 | 15.96 | 91.02 |
| Mean value of | 16.04 | 90.62 |
Example 2
An ultraviolet curing organosilicon release agent is prepared from the following raw materials in parts by weight: 100 parts of organic silicon acrylate oligomer, 20 parts of pentaerythritol triacrylate and 4 parts of Darocur1173 (photoinitiator).
The preparation method of the organic silicon acrylate oligomer comprises the following steps: 20.00g of hydrogen-terminated polydimethylsiloxane (Mn: 4000, available from Guangdong Ningjiang chemical Co., Ltd.) and 5.25g of dipentaerythritol pentaacrylate (the mass ratio of the substances is 1:2), 0.25g of Spiecer catalyst, 0.03g of p-methoxyphenol and 12.62g of toluene were charged into a reaction vessel, stirred uniformly, heated to 100 ℃ for reaction for 6 hours, and after the reaction was completed, the solvent was removed by rotary evaporation to obtain an organosilicon acrylate oligomer.
The IR spectrum of the silicone acrylate oligomer obtained in example 2 is shown in FIG. 1, from which it can be seen that the present invention successfully synthesized the silicone acrylate oligomer.
And stirring and uniformly mixing 100 parts of the obtained organic silicon acrylate oligomer, 20 parts of pentaerythritol triacrylate and 4 parts of Darocur1173 (photoinitiator) to obtain the ultraviolet curing organic silicon mold release agent.
And (3) coating the ultraviolet curing organosilicon release agent on a PET film by using a 2-micron wire bar in a scraping manner, then putting the coated PET film into a CH-1022000W UV curing box, and curing for 30 seconds to obtain the cured organosilicon release coating. The results of the release property test are shown in table 2 below. Numbers 1, 2, 3 indicate that three replicates were made and then averaged.
Table 2 release performance test results of the uv-curable silicone release agent prepared in example 2
| Serial number | Normal temperature release force (g/25mm) | Residual adhesion (%) |
| 1 | 13.57 | 92.54 |
| 2 | 13.54 | 93.67 |
| 3 | 13.71 | 93.24 |
| Mean value of | 13.61 | 93.15 |
Example 3
An ultraviolet curing organosilicon release agent is prepared from the following raw materials in parts by weight: 100 parts of organic silicon acrylate oligomer, 20 parts of pentaerythritol triacrylate and 4 parts of Darocur1173 (photoinitiator).
The preparation method of the organic silicon acrylate oligomer comprises the following steps: 20.00g of hydrogen-terminated polydimethylsiloxane (Mn-6000, available from Guangdong Ningjiang chemical Co., Ltd.) and 3.50g of dipentaerythritol pentaacrylate (the mass ratio of the substances is 1:2), 0.24g of Spiecer catalyst, 0.02g of p-methoxyphenol and 11.75g of toluene were charged into a reaction vessel, stirred uniformly, heated to 100 ℃ for reaction for 6 hours, and after the reaction was completed, the solvent was removed by rotary evaporation to obtain an organosilicon acrylate oligomer.
And stirring and uniformly mixing 100 parts of the obtained organic silicon acrylate oligomer, 20 parts of pentaerythritol triacrylate and 4 parts of Darocur1173 (photoinitiator) to obtain the ultraviolet curing organic silicon mold release agent.
And (3) coating the ultraviolet curing organosilicon release agent on a PET film by using a 2-micron wire bar in a scraping manner, then putting the coated PET film into a CH-1022000W UV curing box, and curing for 30 seconds to obtain the cured organosilicon release coating. The results of the release property test are shown in table 3 below. Numbers 1, 2, 3 indicate that three replicates were made and then averaged.
Table 3 release performance test results of the uv-curable silicone release agent prepared in example 3
| Serial number | Normal temperature release force (g/25mm) | Residual adhesion (%) |
| 1 | 11.38 | 88.34 |
| 2 | 11.38 | 87.56 |
| 3 | 11.40 | 89.43 |
| Mean value of | 11.39 | 88.44 |
Example 4
An ultraviolet curing organosilicon release agent is prepared from the following raw materials in parts by weight: 100 parts of organic silicon acrylate oligomer, 20 parts of trimethylolpropane triacrylate and 4 parts of Darocur1173 (photoinitiator).
The preparation method of the organic silicon acrylate oligomer comprises the following steps: 20.00g of hydrogen-terminated polydimethylsiloxane (Mn: 2000, available from Guangdong Ningjiang chemical Co., Ltd.), 5.96g of pentaerythritol triacrylate (the mass ratio of the substances is 1:2), 0.26g of a Spierer catalyst, 0.03g of p-methoxyphenol and 12.98g of toluene were charged into a reaction vessel, stirred uniformly, heated to 100 ℃ for reaction for 6 hours, and after the reaction was completed, the solvent was removed by rotary evaporation to obtain an organosilicon acrylate oligomer.
And uniformly stirring and mixing 100 parts of the obtained organic silicon acrylate oligomer, 20 parts of trimethylolpropane triacrylate and 4 parts of Darocur1173 (photoinitiator) to obtain the ultraviolet curing organic silicon mold release agent.
And (3) coating the ultraviolet curing organosilicon release agent on a PET film by using a 2-micron wire bar in a scraping manner, then putting the coated PET film into a CH-1022000W UV curing box, and curing for 30 seconds to obtain the cured organosilicon release coating. The results of the release property test are shown in table 4 below. Numbers 1, 2, 3 indicate that three replicates were made and then averaged.
Table 4 release performance test results of the uv-curable silicone release agent prepared in example 4
| Serial number | Normal temperature release force (g/25mm) | Residual adhesion (%) |
| 1 | 14.78 | 91.34 |
| 2 | 14.94 | 90.57 |
| 3 | 14.56 | 91.83 |
| Mean value of | 14.76 | 91.25 |
Example 5
An ultraviolet curing organosilicon release agent is prepared from the following raw materials in parts by weight: 100 parts of organic silicon acrylate oligomer, 20 parts of trimethylolpropane triacrylate and 4 parts of Darocur1173 (photoinitiator).
The preparation method of the organic silicon acrylate oligomer comprises the following steps: 20.00g of hydrogen-terminated polydimethylsiloxane (Mn: 4000, available from Guangdong Ningjiang chemical Co., Ltd.) and 2.98g of pentaerythritol triacrylate (mass ratio of 1:2), 0.23g of a Spierer catalyst, 0.02g of p-methoxyphenol and 11.49g of toluene were charged into a reaction vessel, stirred uniformly, heated to 100 ℃ and reacted for 6 hours, and after the reaction was completed, the solvent was removed by rotary evaporation to obtain an organosilicon acrylate oligomer.
The IR spectrum of the silicone acrylate oligomer obtained in example 5 is shown in FIG. 2, from which it can be seen that the present invention successfully synthesized the silicone acrylate oligomer.
And uniformly stirring and mixing 100 parts of the obtained organic silicon acrylate oligomer, 20 parts of trimethylolpropane triacrylate and 4 parts of Darocur1173 (photoinitiator) to obtain the ultraviolet curing organic silicon mold release agent.
And (3) coating the ultraviolet curing organosilicon release agent on a PET film by using a 2-micron wire bar in a scraping manner, then putting the coated PET film into a CH-1022000W UV curing box, and curing for 30 seconds to obtain the cured organosilicon release coating. The results of the release property test are shown in the following table 5. Numbers 1, 2, 3 indicate that three replicates were made and then averaged.
Table 5 test results of release properties of uv-curable silicone release agent prepared in example 5
| Serial number | Normal temperature release force (g/25mm) | Residual adhesion (%) |
| 1 | 11.45 | 92.68 |
| 2 | 10.24 | 91.82 |
| 3 | 10.83 | 91.34 |
| Mean value of | 10.84 | 91.95 |
Example 6
An ultraviolet curing organosilicon release agent is prepared from the following raw materials in parts by weight: 100 parts of organic silicon acrylate oligomer, 20 parts of trimethylolpropane triacrylate and 4 parts of Darocur1173 (photoinitiator).
The preparation method of the organic silicon acrylate oligomer comprises the following steps: 20.00g of hydrogen-terminated polydimethylsiloxane (Mn 6000, available from Guangdong Ningjiang chemical Co., Ltd.), 1.99g of pentaerythritol triacrylate (the mass ratio of the substances is 1:2), 0.22g of a Spiecer catalyst, 0.02g of p-methoxyphenol and 10.99g of toluene were charged into a reaction vessel, stirred uniformly, heated to 100 ℃ for reaction for 6 hours, and after the reaction was completed, the solvent was removed by rotary evaporation to obtain an organosilicon acrylate oligomer.
And uniformly stirring and mixing 100 parts of the obtained organic silicon acrylate oligomer, 20 parts of trimethylolpropane triacrylate and 4 parts of Darocur1173 (photoinitiator) to obtain the ultraviolet curing organic silicon mold release agent.
And (3) coating the ultraviolet curing organosilicon release agent on a PET film by using a 2-micron wire bar in a scraping manner, then putting the coated PET film into a CH-1022000W UV curing box, and curing for 30 seconds to obtain the cured organosilicon release coating. The results of the release property test are shown in table 6 below. Numbers 1, 2, 3 indicate that three replicates were made and then averaged.
Table 6 release performance test results of the uv-curable silicone release agent prepared in example 6
| Serial number | Normal temperature release force (g/25mm) | Residual adhesion (%) |
| 1 | 8.94 | 89.56 |
| 2 | 8.36 | 89.82 |
| 3 | 9.14 | 89.18 |
| Mean value of | 8.81 | 89.52 |
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. The ultraviolet curing organic silicon release agent is characterized by being prepared from the following raw materials in parts by weight:
100 parts of organic silicon acrylate oligomer, namely,
10-30 parts of an active diluent,
1-4 parts of a photoinitiator.
2. The ultraviolet curing organic silicon release agent according to claim 1, which is characterized by being prepared from the following raw materials in parts by weight:
100 parts of organic silicon acrylate oligomer, namely,
20 parts of a reactive diluent, namely 20 parts of a reactive diluent,
4 parts of a photoinitiator.
3. The uv-curable silicone release agent according to claim 1 or 2, characterized in that:
the organic silicon acrylate oligomer is a reaction product of pentaerythritol triacrylate or dipentaerythritol pentaacrylate and hydrogen-terminated polydimethylsiloxane, and the specific structural formula is as follows:
wherein n is 25 to 80, R is
One kind of (1).
4. The uv-curable silicone release agent according to claim 1 or 2, characterized in that:
the organic silicon acrylate oligomer is prepared by the following method: uniformly mixing hydrogen-terminated polydimethylsiloxane, pentaerythritol triacrylate or dipentaerythritol pentaacrylate, a catalyst, a polymerization inhibitor and a solvent, heating for reaction, and performing rotary evaporation to remove the solvent after the reaction is finished to obtain the organic silicon acrylate oligomer.
5. The ultraviolet-curable silicone release agent according to claim 4, characterized in that:
the structural formula of the hydrogen-terminated polydimethylsiloxane is H (CH)3)2SiO[(CH3)2SiO]nSi(CH3)2H, wherein Mn is 2000-;
the catalyst is at least one of Karstedt catalyst or Spiecer catalyst;
the polymerization inhibitor is at least one of hydroquinone, p-methoxyphenol, o-methyl hydroquinone, p-tert-butyl catechol and p-benzoquinone; the solvent is at least one of toluene and isopropanol;
the hydrogen-terminated polydimethylsiloxane, pentaerythritol triacrylate or dipentaerythritol pentaacrylate, a catalyst, a polymerization inhibitor and a solvent are used in the following amounts: the mass ratio of the hydrogen-terminated polydimethylsiloxane to the acrylate is 1:2 to 1: 2.5; the concentration of the catalyst is 4-20 ppm; the mass of the polymerization inhibitor is 0.01-0.1% of the total weight of the reactants; the mass of the solvent is 50-150% of the total weight of the reactants;
the temperature-rising reaction is carried out at 80-110 ℃ for 4-8 hours.
6. The uv-curable silicone release agent according to claim 1 or 2, characterized in that:
the reactive diluent is a reactive monomer having at least one acrylate group.
7. The uv-curable silicone release agent according to claim 1 or 2, characterized in that:
the active diluent is at least one of butyl acrylate, isooctyl acrylate, isodecyl acrylate, lauryl acrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, 1, 4-butanediol diacrylate, 1, 6-hexanediol diacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate and pentaerythritol tetraacrylate.
8. The uv-curable silicone release agent according to claim 1 or 2, characterized in that:
the photoinitiator is at least one of 2-hydroxy-2-methyl propiophenone, 1-hydroxy-cyclohexyl benzophenone, 2-methyl 1- (4-methylthiophenyl) -2-morpholinoacetone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone and benzophenone.
9. The preparation method of the ultraviolet curing organic silicon release agent according to any one of claims 1 to 8, characterized by comprising the following steps: and weighing the organic silicon acrylate oligomer, the reactive diluent and the photoinitiator according to the proportion, and mixing and stirring uniformly to obtain the ultraviolet curing organic silicon release agent.
10. The use method of the ultraviolet curing organic silicon release agent according to any one of claims 1 to 8 is characterized by comprising the following steps: the coating is coated on the outer surface layer of metal, glass, paper or plastic by adopting a spraying or brushing way, and is cured into a mold release coating under the irradiation of ultraviolet light.
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