CN102981367A - Photosensitive composition containing 4-(2,4,6-trimethyl benzene formyl) diphenyl sulfide as photoinitiator - Google Patents
Photosensitive composition containing 4-(2,4,6-trimethyl benzene formyl) diphenyl sulfide as photoinitiator Download PDFInfo
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Abstract
The invention relates to a photosensitive composition and an application of the photosensitive composition in photo-curing materials, belonging to the technical field of photo-curing. The photo-curing composition provided by the invention comprises the following components in parts by weight: 2-6 parts of 4-(2,4,6-trimethyl benzene formyl) diphenyl sulfide photoinitiator, 1-10 parts of organic amine assistant photoinitiator, 20-80 parts of ethylene unsaturated compound monomer and 20-80 parts of ethylene unsaturated compound prepolymer. The composition finished product has excellent surface and depth curing performances, high reaction activity, not only keeps the excellent performance of a common benzophenone composition, but also has no odor problem, solves a solubility problem of 4-phenyl benzophenone and 4-thiophenyl benzophenone, has a simple preparation process, does not generate smelly or pungent smell in a production process, does not generate insoluble substances and can be extensively applied to such fields as photocuring paint, printing ink, adhesive, photoresist and the like.
Description
Technical field
The present invention relates to a kind of photosensitive composite and the application in photo-curing material thereof, belong to the photocuring technology field.
Background technology
UV-curing technology has been widely used in the fields such as coating, printing ink, bonding agent, photoresist.Photocurable composition in the UV curing system mainly is comprised of monomer, prepolymer and three parts of light trigger, wherein, light trigger is the main factor that affects the Photocurable composition photosensitive property, when determining a kind of prescription of photopolymerisable compositions, the key point that to seek a kind of good light trigger be technology.
Current, in numerous light triggers of successfully commercially producing, benzophenone is because cheap and good surface cure performance becomes one of the widest light trigger of use, but because the molecular weight of benzophenone, so there is the shortcoming of the serious smell of volatile and easy generation in it.In order to overcome the little and volatile shortcoming of benzophenone molecular weight, people have developed 4-phenyl benzophenone and 4-thiophenyl benzophenone two product, this two product has improved the smell problem of benzophenone, but 4-phenyl benzophenone and 4-thiophenyl benzophenone dissolubility are relatively poor, residue is many after solidifying, had a strong impact on the performance of material, and environmental pollution is larger, has potential safety hazard.
Summary of the invention
It is better to the invention provides a kind of dissolubility, and scentless 4-(2,4, the 6-trimethylbenzoyl) diphenyl sulfide that contains is as the photopolymerizable composition of light trigger.
Technical scheme of the present invention is as follows: a kind of photosensitive composite comprises following component:
(A) 4-of 2-6 mass parts (2,4,6-trimethylbenzoyl) diphenyl sulfide light trigger, structure as shown in the formula (I),
(B) organic amine of 1-10 mass parts helps light trigger, is specially: triethanolamine, methyldiethanolamine or dimethylamino ethyl benzoate;
(C) the vinyl unsaturated compound monomer of 20-80 mass parts is specially: styrene, (methyl) acrylic acid or (methyl) acrylate;
(D) the vinyl unsaturated compound prepolymer of 20-80 mass parts is specially: the carboxylate of the unsaturated simple function group of alkene or polyfunctional group carboxylic acid and polyvalent alcohol or epoxide, and on its chain or the polymkeric substance of ethylene linkage unsaturated group arranged on the side group.
The preferred 3-5 mass parts of the content of the Photoepolymerizationinitiater initiater shown in described component (A) Chinese style (I); The preferred 2-8 mass parts of the content of component (B); The preferred 20-60 mass parts of the content of component (C); The preferred 30-60 mass parts of the content of component (D).
(methyl) acrylate in the component (C) is: methyl acrylate, methyl methacrylate, butyl acrylate, butyl methacrylate, diacrylate-1,6-hexanediol ester (HDDA) or tripropylene glycol diacrylate (TPGDA); Prepolymer in the component (D) is: unsaturated polyester (UP), polyamide and polyurethane or its two or more multipolymers; The polymkeric substance of alkyd resin, (methyl) acrylic or its multipolymer.
The preferred 3-5 mass parts of the content of described component (B); The preferred 30-60 mass parts of the content of component (C); The preferred 30-55 mass parts of the content of component (D).
Photosensitive composite of the present invention can be prepared from by each component of even mixing, and mixing can realize by method known in the field, for example uses stirring machine to stir.
Beneficial effect: photosensitive composite of the present invention has more excellent surface and deeply-curing performance, reactivity is high, not only kept the excellent properties that contains common benzophenone composition, there is not simultaneously the smell problem, solved the solubility problem of 4-phenyl benzophenone and 4-thiophenyl benzophenone, preparation technology is simple, in process of production, do not produce unpleasant or sharp aroma, do not produce insolubles, can be widely used in the fields such as photo-cured coating, printing ink, bonding agent and photoresist.
Embodiment
Below be the prescription by photosensitive composition, the performance of bright photosensitive composite of the present invention specifically.Should be understood that embodiment only is for better understanding the present invention, and should not be construed as limitation of the present invention.
Embodiment 1
A kind of photosensitive composite comprises following component:
(A) light trigger (structural formula (I)) 5g;
(B) triethanolamine 3g;
（C)TPGDA 52g；
(D) epoxy acrylic resin 40g;
The preparation technology of said composition is: under the yellow fluorescent lamp condition, add (A), (B), (C), (D) component in the glass flask that stirring is housed, at room temperature stir material to evenly, namely obtain photosensitive composite of the present invention.
Embodiment 2
A kind of photosensitive composite comprises following component:
(A) light trigger (structural formula (I)) 3g;
(B) triethanolamine 5g;
（C）TPGDA 52g；
(D) epoxy acrylic resin 40g;
Said composition preparation technology is with embodiment 1.
Comparative example 1
A kind of photosensitive composite comprises following component:
(A) benzophenone 5g;
(B) triethanolamine 3g;
（C）TPGDA 52g；
(D) epoxy acrylic resin 40g;
Said composition preparation technology is with embodiment 1.
Comparative example 2
A kind of photosensitive composite comprises following component:
(A) 4-phenyl benzophenone 5g;
(B) triethanolamine 3g;
（C）TPGDA 52g；
(D) epoxy acrylic resin 40g;
Said composition preparation technology is with embodiment 1.
Comparative example 3
A kind of photosensitive composite comprises following component:
(A) 4-thiophenyl benzophenone 5g;
(B) triethanolamine 3g;
（C）TPGDA 52g；
(D) epoxy acrylic resin 40g;
Said composition preparation technology is with embodiment 1.
Test respectively formula I compound, benzophenone, 4-phenyl benzophenone and the solubleness of 4-thiophenyl benzophenone in photocuring common solvent butanone and TPGDA monomer, test result sees Table 1.
The solubleness of table 1 light trigger is (g/100g) relatively
| Formula I compound | Benzophenone | The 4-phenyl benzophenone | 4-thiophenyl benzophenone | |
| Butanone | >50 | >50 | 20 | 25 |
| TPGDA | 46 | 37 | 8 | 14 |
As shown in Table 1, formula I compound is large than the dissolubility of 4-phenyl benzophenone and 4-thiophenyl benzophenone, can effectively solve the solubility problem of light trigger described in the background technology.
Under yellow fluorescent lamp, get the composition of above-described embodiment of same amount and comparative example gained on the PET template, utilize the roller coating film forming, thickness is 6 μ m; For obtaining filming of above-mentioned thickness, coating procedure can be once to finish also to carry out several times.Under high voltage mercury lamp radiation, the PET lamina membranacea that scribbles five samples in embodiment and the comparative example is carried out with the condition exposure, composition is by the free radical reaction polymerization film formation, and experimental result is shown in Table 2.
Table 2 composition filming performance is estimated
| Embodiment 1 | Embodiment 2 | Comparative example 1 | Comparative example 2 | Comparative example 3 | |
| Surface flatness | ○ | ○ | × | × | × |
| Odorlessness | ○ | ○ | × | △ | ○ |
Zero: good especially △: slightly good *: bad
As shown in Table 2, the composition surface smoothness that the combination that contains formula I compound contains benzophenone, 4-phenyl benzophenone or 4-thiophenyl benzophenone is good, but the residue pollution problem that efficient solution is out brought owing to the bad or volatile migration of light trigger dissolubility, the present composition does not have the smell problem simultaneously.
Photosensitive composite preparation technology of the present invention is simple, can find out from above performance evaluation, photosensitive composite of the present invention does not produce pungent niff, does not produce pollutant, can be widely used in the fields such as photo-cured coating, printing ink, bonding agent and photoresist.
Claims (10)
1. photosensitive composite is characterized in that: comprise following component:
(A) 4-of 2-6 mass parts (2,4,6-trimethylbenzoyl) diphenyl sulfide light trigger, structure as shown in the formula (I),
(B) organic amine of 1-10 mass parts helps light trigger, is specially: triethanolamine, methyldiethanolamine or dimethylamino ethyl benzoate;
(C) the vinyl unsaturated compound monomer of 20-80 mass parts is specially: styrene, (methyl) acrylic acid or acrylate;
(D) the vinyl unsaturated compound prepolymer of 20-80 mass parts is specially: the carboxylate of the unsaturated simple function group of alkene or polyfunctional group carboxylic acid and polyvalent alcohol or epoxide, and on its chain or the polymkeric substance of ethylene linkage unsaturated group arranged on the side group.
2. photosensitive composite according to claim 1 is characterized in that: the preferred 3-5 mass parts of the content of the Photoepolymerizationinitiater initiater shown in described component (A) Chinese style (I).
3. photosensitive composite according to claim 1 is characterized in that: the preferred 2-8 mass parts of the content of described component (B).
4. photosensitive composite according to claim 1 is characterized in that: the preferred 20-60 mass parts of the content of described component (C).
5. photosensitive composite according to claim 1 is characterized in that: the preferred 30-60 mass parts of the content of described component (D).
6. photosensitive composite according to claim 1, it is characterized in that: the acrylate in the described component (C) is: methyl acrylate, methyl methacrylate, butyl acrylate, butyl methacrylate, HDDA or TPGDA.
7. photosensitive composite according to claim 1, it is characterized in that: the prepolymer in the described component (D) is: unsaturated polyester (UP), polyamide and polyurethane or its two or more multipolymers; The polymkeric substance of alkyd resin, acrylic or its multipolymer.
8. it is characterized in that: the preferred 3-5 mass parts of the content of described component (B) according to claim 1 or 3 described photosensitive composites.
9. it is characterized in that: the preferred 30-60 mass parts of the content of described component (C) according to claim 1 or 4 described photosensitive composites.
10. photosensitive composite according to claim 1 or 5 is characterized in that: the preferred 30-55 mass parts of the content of described component (D).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012105158898A CN102981367A (en) | 2012-12-05 | 2012-12-05 | Photosensitive composition containing 4-(2,4,6-trimethyl benzene formyl) diphenyl sulfide as photoinitiator |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012105158898A CN102981367A (en) | 2012-12-05 | 2012-12-05 | Photosensitive composition containing 4-(2,4,6-trimethyl benzene formyl) diphenyl sulfide as photoinitiator |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103664827A (en) * | 2013-12-18 | 2014-03-26 | 浙江扬帆新材料股份有限公司 | Method for compounding photo-initiator |
| CN105676590A (en) * | 2016-04-12 | 2016-06-15 | 无锡南理工科技发展有限公司 | Photosensitive resin |
| CN105785715A (en) * | 2016-04-12 | 2016-07-20 | 无锡南理工科技发展有限公司 | Preparing method of photosensitive resin |
| CN109400530A (en) * | 2018-12-05 | 2019-03-01 | 安庆北化大科技园有限公司 | Suitable for the naphthalimide aromatic sulfide type photoinitiator and preparation method of UV-LED photocuring and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6492514B1 (en) * | 1998-11-19 | 2002-12-10 | Lamberti S.P.A. | Bifunctional photoinitiators suitable for photopolymerization and photopolymerizable systems containing the same |
| CN102289150A (en) * | 2010-06-17 | 2011-12-21 | 住友化学株式会社 | Photosensitve resin composition |
| CN102566271A (en) * | 2010-12-10 | 2012-07-11 | 住友化学株式会社 | Photosensitive resin composition |
| CN102749807A (en) * | 2011-04-19 | 2012-10-24 | 住友化学株式会社 | Photosensitive resin composition |
-
2012
- 2012-12-05 CN CN2012105158898A patent/CN102981367A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6492514B1 (en) * | 1998-11-19 | 2002-12-10 | Lamberti S.P.A. | Bifunctional photoinitiators suitable for photopolymerization and photopolymerizable systems containing the same |
| CN102289150A (en) * | 2010-06-17 | 2011-12-21 | 住友化学株式会社 | Photosensitve resin composition |
| CN102566271A (en) * | 2010-12-10 | 2012-07-11 | 住友化学株式会社 | Photosensitive resin composition |
| CN102749807A (en) * | 2011-04-19 | 2012-10-24 | 住友化学株式会社 | Photosensitive resin composition |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103664827A (en) * | 2013-12-18 | 2014-03-26 | 浙江扬帆新材料股份有限公司 | Method for compounding photo-initiator |
| CN103664827B (en) * | 2013-12-18 | 2015-07-29 | 浙江扬帆新材料股份有限公司 | A kind of synthetic method of light trigger |
| CN105676590A (en) * | 2016-04-12 | 2016-06-15 | 无锡南理工科技发展有限公司 | Photosensitive resin |
| CN105785715A (en) * | 2016-04-12 | 2016-07-20 | 无锡南理工科技发展有限公司 | Preparing method of photosensitive resin |
| CN109400530A (en) * | 2018-12-05 | 2019-03-01 | 安庆北化大科技园有限公司 | Suitable for the naphthalimide aromatic sulfide type photoinitiator and preparation method of UV-LED photocuring and application |
| CN109400530B (en) * | 2018-12-05 | 2022-04-12 | 安庆北化大科技园有限公司 | Naphthalimide aryl thioether type photoinitiator suitable for UV-LED photocuring, and preparation method and application thereof |
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Application publication date: 20130320 |