CN109517432A - A kind of composition of the acylphosphine oxide containing liquid and its application - Google Patents
A kind of composition of the acylphosphine oxide containing liquid and its application Download PDFInfo
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- CN109517432A CN109517432A CN201811345693.2A CN201811345693A CN109517432A CN 109517432 A CN109517432 A CN 109517432A CN 201811345693 A CN201811345693 A CN 201811345693A CN 109517432 A CN109517432 A CN 109517432A
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- Prior art keywords
- acrylate
- methyl
- composition
- photoinitiator
- acylphosphine oxide
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Classifications
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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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
Abstract
A kind of composition of the acylphosphine oxide containing liquid, the composition are suitable for photocuring system, are primarily adapted for use in UV curing system, are particularly suitable for UV curable ink and coating system；The composition of the acylphosphine oxide containing liquid causes activity height, both can also pass through UV-LED radiation curing by high-pressure sodium lamp radiation curing；Both the surface layer solidification that coating may be implemented, also may be implemented deep cure；It is with a wide range of applications.
Description
Technical field
The present invention relates to a kind of composition of acylphosphine oxide containing liquid, the composition is suitable for photocuring system, main
To be suitable for UV curing system, be particularly suitable for UV curable ink and coating system.
Background technique
Acylphosphine oxide is a kind of efficient free radical (I) type photoinitiator, and effective absorption peak is 350-
400nm produces two free radicals of benzoyl and phosphoryl after illumination, can cause polymerization, therefore laser curing velocity is fast, fits
Together in thick film deep cure.Acylphosphine oxide also has a photobleaching simultaneously, the characteristic that coating does not turn yellow, it in white or
High titanium white powder pigment surface can be fully cured, and rear assembly effect is low, noresidue, it can also be used to clear coat, for low gas
The product that taste requires is especially suitable for.
There are mainly three types of presently commercially available acylphosphine oxides, is the oxidation of 2,4,6- trimethyl benzoyl diphenyl bases respectively
Phosphine (TPO), 2,4,6- trimethylbenzoyl phenyl phosphinic acid ethyl ester (TPO-L), phenyl are bis- (2,4,6- trimethylbenzoyl)
Phosphine oxide (819).Wherein TPO and 819 products are in solid forms, and fusing point is higher, and there are molten in a part of monomer and oligomer
The problem of solution property difference, constrains the application field of the two products, and TPO-L product is in a liquid state, in various monomers, resin and oligomeric
There is good dispersibility in object, in addition the initiation activity of itself is also very strong, so increasingly receiving photoinitiator using enterprise
Favor.
Although TPO-L application is convenient, its preparation process is often generated disagreeableness to environment due to the limitation of technique
Chloroethanes gas, the product low boiling point are unfavorable for absorbing and recycle, inevitably will cause a degree of environmental pollution；
Volatile chloroethanes is not generated in liquid acylphosphine oxide photoinitiator production process in the present composition, in purple
It has a wide range of applications in outer photocuring system.
Summary of the invention
The present invention provides a kind of composition of photoinitiator of acylphosphine oxide containing liquid, by each ingredient of following parts by weight
Composition:
In the composition of the photoinitiator of acylphosphine oxide containing liquid, photoinitiator can be individually such as formula (I) institute
The liquid acylphosphine oxide shown is also possible to the mixing of liquid acylphosphine oxide and other photoinitiators shown in formula (I)
Object.
Wherein:
R is C3-C20Alkyl, which can be straight-chain, branched or ring-type, the C3-C20Alkyl can also quilt
OH、SH、C1-C4Alkoxy, CN, halogen or-COO (C1-C4Alkyl) replaced, the C3-C20Alkyl be ring-type be can also be with
It is introduced into-O- ,-S- ,-CO- or-N (R4)-。
In the composition of the photoinitiator of acylphosphine oxide containing liquid, alkenes unsaturated group prepolymer is polyester tree
Rouge, modified polyester resin, polyurethane resin, epoxy acrylic resin, modified epoxy, hydroxyl chlorine propyl ester resin.
In the composition of the photoinitiator of acylphosphine oxide containing liquid, alkenes unsaturated group monomer classification includes third
Olefin(e) acid Arrcostab, methacrylic acid hydroxy ester, (methyl) acrylate with cyclic structure or phenyl ring, the dilution of vinyl activity
Agent, glycols diacrylate, propandiols diacrylate, other glycols diacrylates, polyfunctional group activity are dilute
Release agent, alkoxylated acrylate, acrylic acid two dislike luxuriant ester, alkoxylated bis-phenol A bis- (methyl) acrylate, vinyl ethers
Reactive diluent, (methyl) acrylate of the end group containing methoxy, phosphorous flame retardant acrylate；Refer specifically to Isooctyl acrylate monomer
(2-EHA), isodecyl acrylate (IDA), lauryl acrylate (LA), glycidyl methacrylate (GMA), metering system
Sour isobornyl thiocyanoacetate (IBOA), phenoxyethyl acrylate (POEA), 1,4-butanediol diacrylate (BDDA), 1,6- hexylene glycol
Diacrylate (HDDA), phthalic acid diethanol diacrylate (PDDA), diethylene glycol diacrylate (DEGDA),
Triethylene glycol diacrylate (TEGDA), pentaerythritol triacrylate (PETA), pentaerythritol tetraacrylate (PETTA),
Two contracting trimethylolpropane tetra-acrylate (DTNPTA) polyethyleneglycol diacrylates (PEGDA), neopentyl glycol diacrylate
Ester (NPGDA), two contracting propylene glycol double methacrylates (DPGDA), double pentaerythritol methacrylate (DPHA) dipentaerythritol five
Acrylate (DPPA), triethoxy trimethylolpropane trimethacrylate (3EOTMPTA), trimethylolpropane tris propylene
Acid esters (TMPTA), tri (propylene glycol) diacrylate (TPGDA).
In the composition of the photoinitiator of acylphosphine oxide containing liquid, other auxiliary agents include filler, pigment, levelling
Agent, dispersing agent, defoaming agent, polymerization inhibitor or their any mixture.
Wherein, the liquid acylphosphine oxide initiator of the structure as shown in formula (I) includes following specific structure compound:
Photoinitiator in composition is liquid acylphosphine oxide shown in formula (I) and other types of photoinitiator
When compound, other type photoinitiators have referred mainly to 2- hydroxy-methyl phenyl-propane -1- ketone (UV1173), 1- hydroxyl-ring
Base-phenyl ketone (UV184), 2- methyl -2- (4- morpholinyl) -1- [4- (methyl mercapto) phenyl] -1- acetone (UV907), 2- benzene
Base benzyl -2- dimethyl amine -1- (4- morpholine benzyl phenyl) butanone (UV369), benzophenone (BP), 4- phenyl benzophenone (PBZ),
4- methyl benzophenone (MBP), isopropyl thioxanthone (ITX), 2,4- diethyl thioxanthone (DETX), o-benzoyl benzene first
Sour methyl esters (MBF), methyl o-benzoylbenzoate (OMBB).
Filler includes talcum powder, silica, calcene, barium sulfate and kaolin in other auxiliary agents；
Pigment includes white pigment, black pigment, color pigment in other auxiliary agents；Specifically can be titanium dioxide, carbon black,
Phthalocyanine blue, paratonere, pigment yellow, phthalocyanine green, forever solid orange, solid palm fibre and phthalocyanine are purple forever；
Levelling agent includes polyacrylate, modified cellulose, organic silicone grease and fluorocarbon resin in other auxiliary agents；
Dispersing agent includes high molecular polymer, electroneutral polyamide and polyester mixture, low molecular weight in other auxiliary agents
Unsaturated carboxylic acid polymer, the copolymer containing acidic-group, the block copolymer containing acidic-group alkyl ammonium salt, polyurethane
Derivative and polyacrylate；
Defoaming agent includes organic silicon modified by polyether, higher alcohols, dimethyl silicone polymer in other auxiliary agents；
Polymerization inhibitor includes quinhydrones, Hydroquinone monomethylether, hydroquinone, p-hydroxyanisole in other auxiliary agents.
The composition of the acylphosphine oxide provided by the invention containing liquid is suitable for photocuring system, is primarily adapted for use in ultraviolet
Photocuring system is particularly suitable for UV curable ink and coating system；The composition is after body surface film through ultraviolet
Radiation of light source curing molding, ultraviolet source used can be high-pressure sodium lamp light source, be also possible to UV-LED light source；Ultraviolet source wave
Long range can be 200nm-500nm.
The present invention has the advantage that
(1) composition of the acylphosphine oxide provided by the invention containing liquid draws in ultraviolet-curing paint or ink
Hair activity is high, and curing time is short, and solidification process also few VOC emissions, are a kind of environmentally protective ultraviolet light curing formulas.
(2) composition of the acylphosphine oxide provided by the invention containing liquid both can by high-pressure sodium lamp radiation curing,
Can also be by UV-LED radiation curing, it can great energy saving when being solidified using LED radiation.
(3) deep cure of coating both may be implemented in the composition of the acylphosphine oxide provided by the invention containing liquid,
Surface layer solidification may be implemented, to keep curing of coatings more thorough.
Specific embodiment
The present invention will be described further by following embodiments.
The composition for the acylphosphine oxide containing liquid that following embodiment provides is applied to ultraviolet cured offset printing ink
Specific formula is shown in Table 1:
Table 1
Composition prepared by the present embodiment is coated on sheet glass, under the UV-LED lamp radiation that wavelength is 365nm
Solidify 10s, 30s, 60s, 120s, judges the surface drying of cured film to characterize curing rate with finger-press method.
Adhesive force measurement: cured film adhesive force is measured using frame method.
Determination of Hardness: pencil hardness method test solidification film hardness is utilized.
Test result is as follows for embodiment 1-3 and comparative example (choose photoinitiator TPO-L+UV1173 and do comparative run):
| Embodiment | Curing rate | Adhesive force | Hardness |
| Embodiment 1 | 120s | 3 | 2B |
| Embodiment 2 | 120s | 3 | 2B |
| Embodiment 3 | 60s | 4 | HB |
| Comparative example 4 | 60s | 4 | HB |
It can be seen from the data in the table that the composition of the present invention initiator of acylphosphine oxide containing liquid exists under the same terms
It is suitable with comparative example that 365nmLED lamp radiates lower solidification effect, when exclusive use liquid acylphosphine oxide is as initiator
The radiation of 365nmLED lamp is lower good not as good as compounding photoinitiator solidification effect.
The composition for the acylphosphine oxide containing liquid that following embodiment provides is applied to the specific of ultraviolet-curing paint
Formula is shown in Table 2:
Table 2
Composition prepared by the present embodiment is coated on sheet glass, is solidified under the radiation of 2000w high-pressure sodium lamp lamp
10s, 20s, 40s, 80s, 120s judge the surface drying of cured film to characterize curing rate with finger-press method.
Adhesive force measurement: cured film adhesive force is measured using frame method.
Determination of Hardness: pencil hardness method test solidification film hardness is utilized.
Xanthochromia test: according to GB/T1865-2009 standard determination.
Test result is as follows for embodiment 1-3 and comparative example (choose photoinitiator TPO and do comparative run):
It can be seen from the data in the table that the composition of the present invention initiator of acylphosphine oxide containing liquid is in height under the same terms
The lower contrast effect for solidifying each parameter of pressure mercury lamp radiation is all suitable with comparative example, can be widely suitable for photocureable coating row
Industry.
Claims (10)
1. a kind of composition of the photoinitiator of acylphosphine oxide containing liquid, which is characterized in that by each ingredient of following parts by weight
Composition:
。
2. photoinitiator composite according to claim 1, which is characterized in that the photoinitiator can be individually such as formula
(I) liquid acylphosphine oxide shown in is also possible to liquid acylphosphine oxide shown in formula (I) and other photoinitiators
Mixture.
Wherein:
R is C3-C20Alkyl, which can be straight-chain, branched or ring-type, the C3-C20Alkyl can also by OH,
SH、C1-C4Alkoxy, CN, halogen or-COO (C1-C4Alkyl) replaced, the C3-C20Alkyl can be drawn when being cyclic annular
Enter-O- ,-S- ,-CO- or-N (R4)-。
3. according to photoinitiator composite described in right 1, which is characterized in that the alkenes unsaturated group prepolymer includes epoxy
Acrylic resin, polyurethane acrylic resin, polyester acrylate resin, polyoxyalkylene acrylate resin, pure acrylate resin, ethylene
Base resin and their modified product.
4. according to photoinitiator composite described in right 1, which is characterized in that the alkenes unsaturated group monomer classification includes third
Olefin(e) acid Arrcostab, methacrylic acid hydroxy ester, (methyl) acrylate with cyclic structure or phenyl ring, the dilution of vinyl activity
Agent, glycols diacrylate, propandiols diacrylate, other glycols diacrylates, polyfunctional group activity are dilute
Release agent, alkoxylated acrylate, acrylic acid two dislike luxuriant ester, alkoxylated bis-phenol A bis- (methyl) acrylate, vinyl ethers
Reactive diluent, (methyl) acrylate of the end group containing methoxy, phosphorous flame retardant acrylate；Refer specifically to Isooctyl acrylate monomer
(2-EHA), isodecyl acrylate (IDA), lauryl acrylate (LA), glycidyl methacrylate (GMA), metering system
Sour isobornyl thiocyanoacetate (IBOA), phenoxyethyl acrylate (POEA), 1,4-butanediol diacrylate (BDDA), 1,6- hexylene glycol
Diacrylate (HDDA), phthalic acid diethanol diacrylate (PDDA), diethylene glycol diacrylate (DEGDA),
Triethylene glycol diacrylate (TEGDA), pentaerythritol triacrylate (PETA), pentaerythritol tetraacrylate (PETTA),
Two contracting trimethylolpropane tetra-acrylate (DTNPTA) polyethyleneglycol diacrylates (PEGDA), neopentyl glycol diacrylate
Ester (NPGDA), two contracting propylene glycol double methacrylates (DPGDA), double pentaerythritol methacrylate (DPHA) dipentaerythritol five
Acrylate (DPPA), triethoxy trimethylolpropane trimethacrylate (3EOTMPTA), trimethylolpropane tris propylene
Acid esters (TMPTA), tri (propylene glycol) diacrylate (TPGDA).
5. according to photoinitiator composite described in right 1, which is characterized in that other auxiliary agents include filler, pigment, levelling
Agent, dispersing agent, defoaming agent, polymerization inhibitor or their any mixture.
6. according to photoinitiator composite described in right 2, which is characterized in that structural compounds shown in formula (I) include following chemical combination
Object:
。
7. according to photoinitiator composite described in right 2, which is characterized in that other photoinitiators refer to 2- hydroxy-methyl benzene
Base propane -1- ketone (UV1173), 1- hydroxyl-cyclohexyl-phenyl ketone (UV184), 2- methyl -2- (4- morpholinyl) -1- [4-
(methyl mercapto) phenyl] -1- acetone (UV907), 2- phenyl benzyl -2- dimethyl amine -1- (4- morpholine benzyl phenyl) butanone (UV369),
Benzophenone (BP), 4- phenyl benzophenone (PBZ), 4- methyl benzophenone (MBP), isopropyl thioxanthone (ITX), 2,4-
Diethyl thioxanthone (DETX), methyl o-benzoylbenzoate (MBF), methyl o-benzoylbenzoate (OMBB).
8. according to photoinitiator composite described in right 5, which is characterized in that
The filler includes talcum powder, silica, calcene, barium sulfate and kaolin；
The pigment includes white pigment, black pigment, color pigment；It specifically can be titanium dioxide, carbon black, phthalocyanine blue, pigment
Red, pigment yellow, phthalocyanine green, forever solid orange, solid palm fibre and phthalocyanine are purple forever.
The levelling agent includes polyacrylate, modified cellulose, organic silicone grease and fluorocarbon resin；
The dispersing agent includes that high molecular polymer, electroneutral polyamide and polyester mixture, low molecular weight unsaturated carboxylic acid are poly-
Close object, the copolymer containing acidic-group, the alkyl ammonium salt of the block copolymer containing acidic-group, urethane derivative and poly- third
Olefin(e) acid ester；
The defoaming agent includes organic silicon modified by polyether, higher alcohols, dimethyl silicone polymer；
The polymerization inhibitor includes quinhydrones, Hydroquinone monomethylether, hydroquinone, p-hydroxyanisole.
9. photoinitiator composite according to claim 1, which is characterized in that the composition is suitable for photocuring system, main
To be suitable for UV curing system, be particularly suitable for UV curable ink and coating system.
10. photoinitiator composite according to claim 1, which is characterized in that the composition is after body surface film
It is formed through ultraviolet source radiation curing, wherein the ultraviolet source can be high-pressure sodium lamp light source, is also possible to UV-LED light source；
The ultraviolet source wave-length coverage can be 200nm-500nm.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115612112A (en) * | 2021-07-16 | 2023-01-17 | 常州强力先端电子材料有限公司 | Organic phosphorus macromolecule initiator, preparation method thereof and photocuring composition |
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Application publication date: 20190326 |