CN1594399A - Cpolymerized thioxanthone high molecular photoinitiator and process for preparing same - Google Patents
Cpolymerized thioxanthone high molecular photoinitiator and process for preparing same Download PDFInfo
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- CN1594399A CN1594399A CN 200410025686 CN200410025686A CN1594399A CN 1594399 A CN1594399 A CN 1594399A CN 200410025686 CN200410025686 CN 200410025686 CN 200410025686 A CN200410025686 A CN 200410025686A CN 1594399 A CN1594399 A CN 1594399A
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- thioxanthone
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Abstract
The invention discloses a copolymerized thioxanthone high molecular photoinitiator and process for preparing same which consists of, using 2-mercaptobenzoic acid, diphenol and chloroepoxy propane as raw meterials to synthesize thioxanthene ketone having double epoxy radicals, then dissolving thioxanthene ketone and diamine into dissolvent, elevating the temperature for several hours to polymerize, obtaining macromolecular thioxanthene ketone, then acylating thioxanthene ketone macro molecules with acryloyl chloride to obtain the copolymerized thioxanthone high molecular photoinitiator.
Description
Technical field: the invention belongs to a kind of functional high molecule material and preparation method thereof, particularly copoly type thioxanthone high-molecular optical initiator and preparation method thereof.
Background technology: the widespread use of UV-curing technology on industrial circles such as photo-cured coating, photoresist material, light-curable ink, electronic package material, tackiness agent, optical media replication, paper glazing shown bright development prospect.In the technical progress process of photocuring system, the research and development of photoinitiator system are all the time in occupation of crucial position.Commercial a large amount of thioxanthone (isopropyl thioxanthone, US Patent 6025408) as the efficiency light initiator is not only poor with the photocuring system consistency, and must could use at aided initiating amine.This has not only reduced the light-initiated efficient of thioxanthone, and the field of having limited its application.
Along with science and technology development, also more and more higher to various performances (velocity of initiation is with the consistency of photocuring system, toxicity, the stability of the storage) requirement of light trigger.For photocuring system, in long process of preservation, owing to volatilize easily with photocuring system consistency difference and move, this can reduce the photopolymerization efficiency of initiation on the one hand, can cause product smell and toxicity to occur on the other hand as the light trigger of small molecules type.Therefore research and development polymer light trigger efficient, low toxicity becomes the focus that people pay close attention to.
Summary of the invention: the present invention obtains the thioxanthone polymer by with small molecules light trigger thioxanthone and aided initiating two secondary amine addition polymerizations, prepares copoly type thioxanthone high-molecular optical initiator by acrylate chloride acidylate thioxanthone macromole then.Not only allow thioxanthone use under the condition of aided initiating need not, improved the light-initiated efficient of thioxanthone, and widened the range of application of thioxanthone as light trigger.
Copoly type thioxanthone high-molecular optical initiator of the present invention, its repeated structural unit is as follows:
Wherein, x is greater than 1, y: z=1: 100-100: 1, and x: (y+z)=1: 100-100: 1, n=2-10000;
R
1Independently be selected from the alkyl of C2-C18 respectively, R
2Independently be selected from the alkyl of C1-C18 respectively;
R
3And R
4Independently be selected from hydrogen respectively, halogen, the alkyl of C1-C18 or alkoxyl group;
R
5And R
6Independently be selected from the alkyl of hydrogen or C1-C18 respectively.
The method of the preparation of copoly type thioxanthone high-molecular optical initiator of the present invention is as follows, and following umber is in weight unit:
(a) 1 part thiosalicylic acid at room temperature is dissolved in the vitriol oil of 5-50 part, adds the diphenol of 0.5-5 part then gradually, at stirring at normal temperature 1-10 hour, be warmed up to 60-100 ℃ of reaction 2-10 hour then, the cooling standing over night.Reaction soln is added drop-wise in ten times the boiling water, cooled and filtered, filter cake is in water and 1, and recrystallization in the 4-dioxane obtains the thioxanthone of two hydroxyls.Two hydroxyl thioxanthones of 1 part are dissolved in the organic solvent of 5-50 part, add Anhydrous potassium carbonate of 1-10 part and the epoxy chloropropane of 0.5-10 part, reacted 2-24 hour down at 60-100 ℃, then at 120-150 ℃ of following backflow 2-24 hour, after reaction finishes, wash organic phase with water and use the Calcium Chloride Powder Anhydrous drying, drain organic phase, the residue recrystallization obtains containing the thioxanthone of diepoxy group;
(b) 1 part the thioxanthone that contains two epoxide groups is dissolved in the organic solvent of 5-50 part, adds the di-secondary amine monomers, 40 ℃-100 ℃ reactions 1-20 hour down, the molar ratio range of thioxanthone and di-secondary amine monomers is 2: 1-2: 4.After reaction finishes, solution poured in the water precipitate, filter, filter cake is washed for several times with deionized water, 40 ℃ of vacuum-dryings 48 hours the thioxanthone polymer; Then 1 part thioxanthone polymer is dissolved in the organic solvent of 5-50 part, add 1-20 part triethylamine,-50-50 ℃ following 1-20 part acrylate chloride monomer that drips, after having reacted solution is poured in the dilute sodium hydroxide aqueous solution, filtering-depositing, drying obtain target product copoly type thioxanthone high-molecular optical initiator.
The entire reaction equation that the present invention prepares copoly type thioxanthone high-molecular optical initiator can be expressed as:
Organic solvent used in the present invention comprises dimethyl sulfoxide (DMSO), methyl alcohol, ethanol, propyl alcohol, N-methyl-pyrrolidone, N, N '-dimethyl formamide, N, N '-N,N-DIMETHYLACETAMIDE, pimelinketone, butanone, acetone, chloroform, toluene or dimethylbenzene.
Di-secondary amine monomers chemical structure used in the present invention is shown below:
R wherein
1Independently be selected from the alkyl of C2-C18 respectively, R
2Independently be selected from the alkyl of C1-C18 respectively.
The chemical structure of diphenol used in the present invention is shown below:
R wherein
3And R
4Independently be selected from hydrogen respectively, halogen, the alkyl of C1-C18 or alkoxyl group.
The monomeric chemical structural formula of acrylate chloride used in the present invention is shown below:
Wherein, R
5And R
6Independently be selected from the alkyl of hydrogen or C1-C18 respectively.
Copoly type thioxanthone high-molecular optical initiator of the present invention because main chain contains aided initiating amine and light trigger thioxanthone simultaneously, makes light-initiated performance improve; Simultaneously, it is again a kind of polymer, and contain on the side chain can the polymeric unsaturated double-bond, is difficult for moving to the surface in light-cured resin preservation process, has reduced the toxicity of light trigger; And contain coinitiator amine in the molecular structure, must not add coinitiator again in the use, so it will have wide practical use in the photocuring field.
Description of drawings:
Fig. 1 is the infrared spectra of embodiment 1 copoly type thioxanthone high-molecular optical initiator.
Fig. 2 is the nucleus magnetic hydrogen spectrum of embodiment 1 copoly type thioxanthone high-molecular optical initiator.
Concrete embodiment: following embodiment further specifies of the present invention, rather than limits the scope of the invention.
Embodiment 1
(a): the thiosalicylic acid of 16g (0.1mol) is dissolved in the vitriol oil of 150g, and stirring at room 10 minutes slowly adds the Resorcinol of 44g (0.4mol), and reaction is 60 minutes under the room temperature, is warmed up to 80 ℃ of reactions then after 120 minutes, standing over night.Reaction solution is added drop-wise in the boiling water of 1500g, boiled again after dripping 10 minutes, cooled and filtered, filter cake is in water and 1, and recrystallization in the 4-dioxane obtains 1 of 11.2 grams, 4-dihydroxyl thioxanthone, productive rate 50%.With 1 of 3.56g (0.01mol), 4-dihydroxyl thioxanthone, the Anhydrous potassium carbonate of 6.9g (0.05mol), the epoxy chloropropane of 20ml join in the pimelinketone of 40g, and 80 ℃ were reacted 12 hours, refluxed 12 hours down at 135 ℃ then.After reaction finishes, drain organic layer, residue dissolves in water and chloroform, and organic phase is dewatered with Calcium Chloride Powder Anhydrous, and after draining, residue is recrystallization in toluene and ethanol, obtains 1,4-two (glycidoxy) thioxanthone 2.8 grams, and productive rate is 78.6%.
(b): with 1.64g (5mmol) 1,4-two (glycidoxy) thioxanthone is dissolved in the dimethyl sulfoxide (DMSO) of 30g, adds the piperazine of 0.43g (5mmol), after the dissolving, is warming up to 80 ℃ of reactions 12 hours fully.After reaction finishes solution poured in the aqueous solution of 500g dilute sodium hydroxide and precipitate, filter, filter cake is given a baby a bath on the third day after its birth time with deionized water, and filter cake obtains thioxanthone polymer 2.02g dry 48 hours of 40 ℃ vacuum drying oven, and getting productive rate with respect to thioxanthone is 90%; Thioxanthone polymer and the 1g triethylamine of 1g are dissolved in the 20g dimethyl formamide, under 0 ℃, splash into the methacrylic chloride of 2g, react after 4 hours, solution is poured in the dilute sodium hydroxide aqueous solution of 200g, filtering drying obtains copoly type thioxanthone high-molecular optical initiator.
1H NMR ([d
6] DMSO, 400MHz): δ=8.24-7.08 (6H, phenyl ring), 5.99-5.95 (3.24H, CH
2=C), 4.37-4.22 (6H ,-OCH
2,-OCH), 2.48-2.41 (12H ,-NCH
2), 1.83 (4.9H, CH
3), see Fig. 2.FT-IR (KBr): 3401 (O-H), 2923,2813 (C-H), 1716
1628cm
-1 
See Fig. 1.
Embodiment 2
(a): the thiosalicylic acid of 16g (0.1mol) is dissolved in the vitriol oil of 150g, and stirring at room 10 minutes slowly adds the Resorcinol of 44g (0.4mol), and reaction is 60 minutes under the room temperature, is warmed up to 80 ℃ of reactions then after 120 minutes, standing over night.Reaction solution is added drop-wise in the boiling water of 1500g, boiled again after dripping 10 minutes, cooled and filtered, filter cake is in water and 1, and recrystallization in the 4-dioxane obtains 1 of 11.2 grams, 4-dihydroxyl thioxanthone, productive rate 50%.With 1 of 3.56g (0.01mol), 4-dihydroxyl thioxanthone, the Anhydrous potassium carbonate of 6.9g (0.05mol), the epoxy chloropropane of 20ml join in the pimelinketone of 40g, and 80 ℃ were reacted 12 hours, refluxed 12 hours down at 135 ℃ then.After reaction finishes, drain organic layer, residue dissolves in water and chloroform, and organic phase is dewatered with Calcium Chloride Powder Anhydrous, and after draining, residue is recrystallization in toluene and ethanol, obtains 1,4-two (glycidoxy) thioxanthone 2.8 grams, and productive rate is 78.6%.
(b): with 1.64g (5mmol) 1,4-two (glycidoxy) thioxanthone is dissolved in the dimethyl sulfoxide (DMSO) of 30g, adds the N of 0.44g (5mmol), and N '-dimethyl-quadrol after the dissolving, is warming up to 80 ℃ of reactions 12 hours fully.After reaction finishes solution poured in the aqueous solution of 500g dilute sodium hydroxide and precipitate, filter, filter cake is given a baby a bath on the third day after its birth time with deionized water, and filter cake obtains thioxanthone polymer 2.02g dry 48 hours of 40 ℃ vacuum drying oven, and getting productive rate with respect to thioxanthone is 90%; Thioxanthone polymer and the 1g triethylamine of 1g are dissolved in the 20g dimethyl formamide, under 0 ℃, splash into the methacrylic chloride of 2g, react after 4 hours, solution is poured in the dilute sodium hydroxide aqueous solution of 200g, filtering drying obtains copoly type thioxanthone high-molecular optical initiator.
1H NMR ([d
6] DMSO, 400MHz): δ=8.24-7.08 (6H, phenyl ring), 5.99-5.95 (3.24H, CH
2=C), 4.37-4.22 (6H ,-OCH
2,-OCH), 2.48-2.41 (14H ,-NCH
2,-NCH
3), 1.83 (4.9H, CH
3).FT-IR(KBr)：3401(O-H)，2923，2813(C-H)，1716
1628cm
-1
Embodiment 3
(a): the thiosalicylic acid of 16g (0.1mol) is dissolved in the vitriol oil of 150g, and stirring at room 10 minutes slowly adds the Resorcinol of 44g (0.4mol), and reaction is 60 minutes under the room temperature, is warmed up to 80 ℃ of reactions then after 120 minutes, standing over night.Reaction solution is added drop-wise in the boiling water of 1500g, boiled again after dripping 10 minutes, cooled and filtered, filter cake is in water and 1, and recrystallization in the 4-dioxane obtains 1 of 11.2 grams, 4-dihydroxyl thioxanthone, productive rate 50%.With 1 of 3.56g (0.01mol), 4-dihydroxyl thioxanthone, the Anhydrous potassium carbonate of 6.9g (0.05mol), the epoxy chloropropane of 20ml join in the pimelinketone of 40g, and 80 ℃ were reacted 12 hours, refluxed 12 hours down at 135 ℃ then.After reaction finishes, drain organic layer, residue dissolves in water and chloroform, and organic phase is dewatered with Calcium Chloride Powder Anhydrous, and after draining, residue is recrystallization in toluene and ethanol, obtains 1,4-two (glycidoxy) thioxanthone 2.8 grams, and productive rate is 78.6%.
(b): with 1.64g (5mmol) 1,4-two (glycidoxy) thioxanthone is dissolved in the dimethyl sulfoxide (DMSO) of 30g, adds the N of 0.44g (5mmol), and N '-dimethyl-quadrol after the dissolving, is warming up to 80 ℃ of reactions 12 hours fully.After reaction finishes solution poured in the aqueous solution of 500g dilute sodium hydroxide and precipitate, filter, filter cake is given a baby a bath on the third day after its birth time with deionized water, and filter cake obtains thioxanthone polymer 2.02g dry 48 hours of 40 ℃ vacuum drying oven, and getting productive rate with respect to thioxanthone is 90%; Thioxanthone polymer and the 1g triethylamine of 1g are dissolved in the 20g dimethyl formamide, under 0 ℃, splash into the methacrylic chloride of 2g, react after 4 hours, solution is poured in the dilute sodium hydroxide aqueous solution of 200g, filtering drying obtains copoly type thioxanthone high-molecular optical initiator.
1H NMR ([d
6] DMSO, 400MHz): δ=8.24-7.08 (15H, phenyl ring and CH=CH), 6.65-6.59 (1.64 CH=CH), 4.27-4.01 (6H ,-OCH
2,-OCH), 2.48-2.41 (12H ,-NCH
2), FT-IR (KBr): 3401 (O-H), 2923,2813 (C-H), 1691
1628cm
-1
Claims (6)
1. copoly type thioxanthone high-molecular optical initiator is characterized in that the repeated structural unit of copoly type thioxanthone high-molecular optical initiator is shown below:
Wherein, x is greater than 1, y: z=1: 100-100: 1, and x: (y+z)=1: 100-100: 1, n=2-10000;
R
1Independently be selected from the alkyl of C2-C18 respectively, R
2Independently be selected from the alkyl of C1-C18 respectively;
R
3And R
4Independently be selected from hydrogen respectively, halogen, the alkyl of C1-C18 or alkoxyl group;
R
5And R
6Independently be selected from the alkyl of hydrogen or C1-C18 respectively.
2. the preparation method of copoly type thioxanthone high-molecular optical initiator is characterized in that the preparation method is as follows, and following umber is in weight unit:
(a) 1 part thiosalicylic acid at room temperature is dissolved in the vitriol oil of 5-50 part, adds the diphenol of 0.5-5 part then gradually, at stirring at normal temperature 1-10 hour, be warmed up to 60-100 ℃ of reaction 2-10 hour then, quiet the causing of lowering the temperature spent the night; Reaction soln is added drop-wise in ten times the boiling water, cooled and filtered, filter cake is in water and 1, and recrystallization in the 4-dioxane obtains the thioxanthone of two hydroxyls; Two hydroxyl thioxanthones of 1 part are dissolved in the organic solvent of 5-50 part, add Anhydrous potassium carbonate of 1-10 part and the epoxy chloropropane of 0.5-10 part, reacted 2-24 hour down at 60-100 ℃, then at 120-150 ℃ of following backflow 2-24 hour, after reaction finishes, wash organic phase with water and use the Calcium Chloride Powder Anhydrous drying, drain organic phase, the residue recrystallization obtains containing the thioxanthone of diepoxy group;
(b) 1 part the thioxanthone that contains two epoxide groups is dissolved in the organic solvent of 5-50 part, add the di-secondary amine monomers, reacted 1-20 hour down at 40 ℃-100 ℃, the molar ratio range of thioxanthone and two secondary amine is 2: 1-2: 4, after reaction finishes, solution poured in the water precipitate, filter, filter cake is washed for several times with deionized water, and 40 ℃ of vacuum-dryings got the thioxanthone polymer in 48 hours; Then 1 part thioxanthone polymer is dissolved in the organic solvent of 5-50 part, add 1-20 part triethylamine,-50-50 ℃ following 1-20 part acrylate chloride monomer that drips, after having reacted solution is poured in the dilute sodium hydroxide aqueous solution, filtering-depositing, drying obtain target product copoly type thioxanthone high-molecular optical initiator.
3. the preparation method of copoly type thioxanthone high-molecular optical initiator according to claim 2 is characterized in that the chemical structure of employed di-secondary amine monomers is shown below:
R wherein
1Independently be selected from the alkyl of C2-C18 respectively, R
2Independently be selected from the alkyl of C1-C18 respectively.
4. the preparation method of copoly type thioxanthone high-molecular optical initiator according to claim 2 is characterized in that the chemical structural formula of employed diphenol is shown below:
R wherein
3And R
4Independently be selected from hydrogen respectively, halogen, the alkyl of C1-C18 or alkoxyl group.
5. the preparation method of copoly type thioxanthone high-molecular optical initiator according to claim 2 is characterized in that the monomeric chemical structural formula of employed acrylate chloride is shown below:
Wherein, R
5And R
6Independently be selected from the alkyl of hydrogen or C1-C18 respectively.
6. the preparation method of copoly type thioxanthone high-molecular optical initiator according to claim 2, it is characterized in that employed organic solvent comprises dimethyl sulfoxide (DMSO), methyl alcohol, ethanol, propyl alcohol, N-methyl-pyrrolidone, N, N '-dimethyl formamide, N, N '-N,N-DIMETHYLACETAMIDE, pimelinketone, butanone, acetone, chloroform, toluene or dimethylbenzene.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102212150A (en) * | 2011-04-26 | 2011-10-12 | 盐城工学院 | Polymerizable thioxanthone photoinitiator containing auxiliary initiator amine and preparation method thereof |
| US20120046377A1 (en) * | 2009-04-30 | 2012-02-23 | Siegwerk Benelux Sa | Photoinitiators |
| CN102432699A (en) * | 2011-08-31 | 2012-05-02 | 上海交通大学 | Light trigger based on vegetable oil and preparation method thereof |
| US10400066B2 (en) | 2015-01-27 | 2019-09-03 | Hewlett-Packard Development Company, L.P. | Polymeric photoactive agents |
| US10414927B2 (en) | 2015-01-27 | 2019-09-17 | Hewlett-Packard Development Company, L.P. | Polymeric photo active agents |
| US10414862B2 (en) | 2015-07-09 | 2019-09-17 | Hewlett-Packard Development Company, L.P. | Polymeric amine synergist |
| US10619007B2 (en) | 2015-01-27 | 2020-04-14 | Hewlett-Packard Development Company, L.P. | Polymeric amine synergists |
| CN114561005A (en) * | 2022-04-11 | 2022-05-31 | 中山大学 | Polymerizable thioxanthone aqueous photoinitiator and preparation method and application thereof |
-
2004
- 2004-07-01 CN CN 200410025686 patent/CN1244612C/en not_active Expired - Fee Related
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120046377A1 (en) * | 2009-04-30 | 2012-02-23 | Siegwerk Benelux Sa | Photoinitiators |
| US8598249B2 (en) * | 2009-04-30 | 2013-12-03 | Siegwerk Druckfarben Ag & Co. Kgaa | Photoinitiators |
| CN102212150A (en) * | 2011-04-26 | 2011-10-12 | 盐城工学院 | Polymerizable thioxanthone photoinitiator containing auxiliary initiator amine and preparation method thereof |
| CN102212150B (en) * | 2011-04-26 | 2012-11-28 | 盐城工学院 | Polymerizable thioxanthone photoinitiator containing auxiliary initiator amine and preparation method thereof |
| CN102432699A (en) * | 2011-08-31 | 2012-05-02 | 上海交通大学 | Light trigger based on vegetable oil and preparation method thereof |
| CN102432699B (en) * | 2011-08-31 | 2013-06-12 | 上海交通大学 | Light trigger based on vegetable oil and preparation method thereof |
| US10400066B2 (en) | 2015-01-27 | 2019-09-03 | Hewlett-Packard Development Company, L.P. | Polymeric photoactive agents |
| US10400067B2 (en) | 2015-01-27 | 2019-09-03 | Hewlett-Packard Development Company, L.P. | Polymeric photoactive agent compositions |
| US10414927B2 (en) | 2015-01-27 | 2019-09-17 | Hewlett-Packard Development Company, L.P. | Polymeric photo active agents |
| US10619007B2 (en) | 2015-01-27 | 2020-04-14 | Hewlett-Packard Development Company, L.P. | Polymeric amine synergists |
| US10414862B2 (en) | 2015-07-09 | 2019-09-17 | Hewlett-Packard Development Company, L.P. | Polymeric amine synergist |
| US10421837B2 (en) | 2015-07-09 | 2019-09-24 | Hewlett-Packard Development Company, L.P. | Polymeric amine synergist compositions |
| CN114561005A (en) * | 2022-04-11 | 2022-05-31 | 中山大学 | Polymerizable thioxanthone aqueous photoinitiator and preparation method and application thereof |
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|---|---|
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