CN103941543B - A kind of photosensitive resin composition based on polylactide polyol and preparation method thereof and photosensitive resin - Google Patents
A kind of photosensitive resin composition based on polylactide polyol and preparation method thereof and photosensitive resin Download PDFInfo
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- CN103941543B CN103941543B CN201410116890.2A CN201410116890A CN103941543B CN 103941543 B CN103941543 B CN 103941543B CN 201410116890 A CN201410116890 A CN 201410116890A CN 103941543 B CN103941543 B CN 103941543B
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- Prior art keywords
- photosensitive resin
- polylactide
- resin composition
- polyol
- polylactide polyol
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920000747 poly(lactic acid) Polymers 0.000 title claims abstract description 52
- 229920005862 polyol Polymers 0.000 title claims abstract description 30
- 150000003077 polyols Chemical class 0.000 title claims abstract description 28
- 239000011347 resin Substances 0.000 title claims abstract description 23
- 229920005989 resin Polymers 0.000 title claims abstract description 23
- 239000011342 resin composition Substances 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000004917 polyol method Methods 0.000 title description 3
- -1 acrylic ester Chemical class 0.000 claims abstract description 15
- 238000004132 cross linking Methods 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 14
- 150000003254 radicals Chemical class 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000002202 Polyethylene glycol Substances 0.000 claims description 13
- 125000004386 diacrylate group Chemical group 0.000 claims description 13
- 229920001223 polyethylene glycol Polymers 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 7
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- LJRSZGKUUZPHEB-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COC(C)COC(=O)C=C LJRSZGKUUZPHEB-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 238000000016 photochemical curing Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical group CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 claims 1
- 239000003505 polymerization initiator Substances 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 abstract description 4
- 230000003000 nontoxic effect Effects 0.000 abstract description 4
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
- XHIKSLHIZYVEQI-UHFFFAOYSA-N CC1=C(C(=O)[PH2]=O)C(=CC(=C1)C)C Chemical compound CC1=C(C(=O)[PH2]=O)C(=CC(=C1)C)C XHIKSLHIZYVEQI-UHFFFAOYSA-N 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 231100000956 nontoxicity Toxicity 0.000 description 2
- 230000036314 physical performance Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Materials For Photolithography (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention provides a kind of photosensitive resin composition based on polylactide polyol, the photosensitive resin composition based on polylactide polyol includes polylactide polyol, self-crosslinking acrylic ester monomer and free radical type Photoepolymerizationinitiater initiater, wherein：The mass percent of the polylactide polyol is 40~95%, and the mass percent of the self-crosslinking acrylic ester monomer is 5~60%, and the mass percent of the free radical type Photoepolymerizationinitiater initiater is 1~40%；Present invention also offers the preparation method of the photosensitive resin composition based on polylactide polyol and photosensitive resin.The beneficial effects of the present invention are there is provided it is a kind of it is non-toxic, non-stimulated, available for furniture environment and to aquatic environment nonhazardous is pollution-free and photosensitive resin composition available for ink, coating and stereolithography and preparation method thereof and photosensitive resin.
Description
Technical field
The present invention relates to a kind of photosensitive resin composition based on polylactide polyol and preparation method thereof and photosensitive tree
Fat.
Background technology
At present, photosensitive resin material is a kind of special resin with many-sided superiority, typically by UV-Curable Prepolymer, work
Property diluent and sensitising agent composition.Photosensitive resin material can produce biologically active fragment under the action of uv light, trigger polymerization, crosslinking
Reaction, realizes in moment and solidifies.Current photosensitive resin is largely used in rapid laser-shaping technique, and its general principle is：Will
Photosensitive resin is contained in resin storage tank, there is a platform that can be lifted controlled by computer in resin storage tank.The bottom of from during processing
Portion starts, and laser scanning is carried out according to designed model.Light-cured resin crosslinks polymerization and produced after being irradiated by ultraviolet
A cross-sectional layers for part (thickness is generally 0.11~0.13mm).Then platform moves down a height, before resin is coated in
On one cured layer, solidify new one layer, so repeatedly, ultimately form a complete part.Due to rapid laser-shaping technique energy
The enough time and manufacturing cost with traditional moulds manufacture 1/10 produces the part system for being used directly for small lot injection molding
Product.The advantages of its curing rate is fast, production efficiency is high and suitable industrial flow-line is produced, photosensitive resin is increasingly widely applied
In laser fast shaping manufacturing industry.
The content of the invention
In view of the above-mentioned problems in the prior art, it is a primary object of the present invention to solve the defect of prior art,
There is provided it is a kind of it is non-toxic, non-stimulated, available for furniture environment and to aquatic environment nonhazardous it is pollution-free and available for ink, apply
Photosensitive resin composition of material and stereolithography and preparation method thereof and photosensitive resin.
The invention provides a kind of photosensitive resin composition based on polylactide polyol, the composition includes poly- third
Lactide polyalcohol, self-crosslinking acrylic ester monomer and free radical type Photoepolymerizationinitiater initiater, wherein：The polylactide polyol
Mass percent is 40~95%, and the mass percent of the self-crosslinking acrylic ester monomer is 5~60%, the free radical type
The mass percent of Photoepolymerizationinitiater initiater is 1~40%.
Optionally, the polylactide polyol is polylactide monohydric alcohol, polylactide dihydric alcohol and polylactide
One or more in trihydroxylic alcohol.
Optionally, the polylactide monohydric alcohol is the polylactide monohydric alcohol of each molecular weight, the polylactide binary
Alcohol is the polylactide dihydric alcohol of each molecular weight, and the polylactide trihydroxylic alcohol is the polylactide trihydroxylic alcohol of each molecular weight.
Optionally, the self-crosslinking acrylic ester monomer be polyethyleneglycol diacrylate, polyethyleneglycol diacrylate,
One or more in polyethyleneglycol diacrylate or tri (propylene glycol) diacrylate.
Optionally, the molecular weight of the polyethyleneglycol diacrylate is 200, point of the polyethyleneglycol diacrylate
Son amount is 400, and the molecular weight of the polyethyleneglycol diacrylate is 600.
Optionally, the free radical type Photoepolymerizationinitiater initiater be (2,4,6- trimethylbenzoyl) diphenyl phosphine oxide,
Phenyl double (2,4,6- trimethylbenzoyl) phosphine oxide, 2- dimethylamino -2- benzyls -1- [4- (4- morpholinyls) phenyl] -1- fourths
One or more in ketone and 2- hydroxy-2-methyl -1- phenylacetones.
The present invention also provides a kind of system according to the photosensitive resin composition described above based on polylactide polyol
Preparation Method, this method includes many for 1~4: 40~95: 5~60 free radical type Photoepolymerizationinitiater initiater, polylactide in mass ratio
First alcohol, self-crosslinking acrylic ester monomer are uniformly mixed at normal atmospheric pressure, and temperature during mixing is 20~80 DEG C, is carried out
1~8h homogeneous stirring, makes uniform light yellow transparent liquid.
The present invention also provides a kind of photosensitive resin, and the photosensitive resin is by the light described above based on polylactide polyol
Photosensitive resin composition photocuring is formed.
The present invention has advantages below and beneficial effect：It is a kind of based on the photosensitive of polylactide polyol that the present invention is provided
Resin, with it is non-toxic and non-stimulated the characteristics of, it is pollution-free to aquatic environment nonhazardous available for domestic environment；Meanwhile, can
For ink, coating and stereolithography, its feature is nontoxicity, and good physical performance, Environmental compatibility is good, it is easy on
Color, the subsequent technique etc. such as spraying, available for indoor environment.
Embodiment
Below with reference to specific embodiment, the present invention is further illustrated.
A kind of photosensitive resin composition based on polylactide polyol provided in an embodiment of the present invention, it is described to be based on poly- third
It is poly- that the photosensitive resin composition of lactide polyalcohol includes polylactide polyol, self-crosslinking acrylic ester monomer and free radical type light
Initiator is closed, wherein：The mass percent of the polylactide polyol is 40~95%, the self-crosslinking acrylic ester monomer
Mass percent be 5~60%, the mass percent of the free radical type Photoepolymerizationinitiater initiater is 1~40%.
As the preferred embodiment of above-described embodiment, the polylactide polyol is polylactide monohydric alcohol, poly- third
One or more in lactide dihydric alcohol and polylactide trihydroxylic alcohol.
As the preferred embodiment of above-described embodiment, the polylactide monohydric alcohol is the polylactide one of each molecular weight
First alcohol, the polylactide dihydric alcohol is the polylactide dihydric alcohol of each molecular weight, and the polylactide trihydroxylic alcohol is each molecule
The polylactide trihydroxylic alcohol of amount.
As the preferred embodiment of above-described embodiment, the self-crosslinking acrylic ester monomer is polyethylene glycol diacrylate
One kind or many in ester, polyethyleneglycol diacrylate, polyethyleneglycol diacrylate or tri (propylene glycol) diacrylate
Kind.
As the preferred embodiment of above-described embodiment, the molecular weight of the polyethyleneglycol diacrylate is 200, described
The molecular weight of polyethyleneglycol diacrylate is 400, and the molecular weight of the polyethyleneglycol diacrylate is 600.
As the preferred embodiment of above-described embodiment, the free radical type Photoepolymerizationinitiater initiater is (2,4,6- trimethyls
Benzoyl) diphenyl phosphine oxide, phenyl double (2,4,6- trimethylbenzoyl) phosphine oxide, 2- dimethylamino -2- benzyls -1-
One or more in [4- (4- morpholinyls) phenyl] -1- butanone and 2- hydroxy-2-methyl -1- phenylacetones.
The embodiment of the present invention also provides a kind of according to the lightsensitive resin composition described above based on polylactide polyol
The preparation method of thing, this method is included in mass ratio for 1~4: 40~95: 5~60 free radical type Photoepolymerizationinitiater initiater, poly- third
Lactide polyalcohol, self-crosslinking acrylic ester monomer are uniformly mixed at normal atmospheric pressure, and temperature during mixing is 20~80
DEG C, 1~8h homogeneous stirring is carried out, uniform light yellow transparent liquid is made.
The embodiment of the present invention also provides a kind of photosensitive resin, and the photosensitive resin is by described above polynary based on polylactide
The photosensitive resin composition of alcohol entered photocuring and formed, and the characteristics of photosensitive resin has non-toxic and non-stimulated can be used for
Domestic environment, it is pollution-free to aquatic environment nonhazardous；Meanwhile, available for ink, coating and stereolithography, its feature is
Nontoxicity, good physical performance, Environmental compatibility is good, it is easy to paint, subsequent technique such as spraying etc., available for indoor environment.
Finally it should be noted that：Above-described embodiments are merely to illustrate the technical scheme, rather than to it
Limitation；Although the present invention is described in detail with reference to the foregoing embodiments, it will be understood by those within the art that：
It can still modify to the technical scheme described in previous embodiment, or which part or all technical characteristic are entered
Row equivalent substitution；And these modifications or substitutions, the essence of appropriate technical solution is departed from various embodiments of the present invention technical side
The scope of case.
Claims (8)
1. a kind of photosensitive resin composition based on polylactide polyol, it is characterised in that：The composition includes poly- third and handed over
Ester polyol, self-crosslinking acrylic ester monomer and free radical type Photoepolymerizationinitiater initiater, wherein：The matter of the polylactide polyol
It is 40~95% to measure percentage, and the mass percent of the self-crosslinking acrylic ester monomer is 5~60%, the free radical type light
The mass percent of polymerization initiator is 1~40%, and all components mass percent sum is 100% in the composition.
2. the photosensitive resin composition according to claim 1 based on polylactide polyol, it is characterised in that described poly-
Lactide polyalcohol is the one or more in polylactide dihydric alcohol and polylactide trihydroxylic alcohol.
3. the photosensitive resin composition according to claim 2 based on polylactide polyol, it is characterised in that described poly-
Lactide dihydric alcohol is the polylactide dihydric alcohol of each molecular weight, and the polylactide trihydroxylic alcohol is the polylactide of each molecular weight
Trihydroxylic alcohol.
4. the photosensitive resin composition according to claim 1 based on polylactide polyol, it is characterised in that it is described from
Crosslink propylene acid ester monomer is the one or more in polyethyleneglycol diacrylate and tri (propylene glycol) diacrylate.
5. the photosensitive resin composition according to claim 4 based on polylactide polyol, it is characterised in that described poly-
The molecular weight of glycol diacrylate is 200,400, or 600.
6. the photosensitive resin composition according to claim 1 based on polylactide polyol, it is characterised in that it is described from
It is (2,4,6- trimethylbenzoyl) diphenyl phosphine oxide, double (2,4, the 6- trimethylbenzenes of phenyl by fundamental mode Photoepolymerizationinitiater initiater
Formyl) phosphine oxide, 2- dimethylamino -2- benzyls -1- [4- (4- morpholinyls) phenyl] -1- butanone and 2- hydroxy-2-methyls -1-
One or more in phenylacetone.
7. a kind of system of photosensitive resin composition based on polylactide polyol according to claim 1-6 any one
Preparation Method, it is characterised in that this method includes for 1~4: 40~95: 5~60 free radical type photopolymerization triggering in mass ratio
Agent, polylactide polyol, self-crosslinking acrylic ester monomer are uniformly mixed at normal atmospheric pressure, and temperature during mixing is
20~80 DEG C, 1~8h homogeneous stirring is carried out, uniform light yellow transparent liquid is made.
8. a kind of photosensitive resin, it is characterised in that the photosensitive resin described in claim 1-6 any one based on poly- third as handing over
The photosensitive resin composition photocuring of ester polyol is formed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410116890.2A CN103941543B (en) | 2014-03-27 | 2014-03-27 | A kind of photosensitive resin composition based on polylactide polyol and preparation method thereof and photosensitive resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410116890.2A CN103941543B (en) | 2014-03-27 | 2014-03-27 | A kind of photosensitive resin composition based on polylactide polyol and preparation method thereof and photosensitive resin |
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| Publication Number | Publication Date |
|---|---|
| CN103941543A CN103941543A (en) | 2014-07-23 |
| CN103941543B true CN103941543B (en) | 2017-09-19 |
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| CN201410116890.2A Expired - Fee Related CN103941543B (en) | 2014-03-27 | 2014-03-27 | A kind of photosensitive resin composition based on polylactide polyol and preparation method thereof and photosensitive resin |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3033225B1 (en) * | 2013-08-12 | 2019-12-11 | Sun Chemical Corporation | Energy curable lithographic inks containing lactic acid resins |
| CN105399935B (en) * | 2015-11-16 | 2017-07-11 | 孝感市易生新材料有限公司 | Degradable light-cured resin performed polymer and preparation method, light-cured resin and preparation method |
| CN111909320A (en) * | 2020-07-30 | 2020-11-10 | 武汉工程大学 | Photocuring 3D printing modified polylactic acid composite photosensitive resin and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4952481A (en) * | 1985-02-12 | 1990-08-28 | Napp Systems (Usa), Inc. | Photosensitive resin composition |
| CN101833241A (en) * | 2009-03-09 | 2010-09-15 | 村上精密制版（昆山）有限公司 | Photosensitive resin composition |
| CN102732094A (en) * | 2012-05-21 | 2012-10-17 | 史海生 | LED-UV surface light source light-curing silk-screen printing ink composition and preparation method thereof |
| CN103246164A (en) * | 2013-06-04 | 2013-08-14 | 苏州太速雷电子科技有限公司 | Photosensitive resin for stereo lithography forming and preparation method thereof |
| CN103616799A (en) * | 2013-11-07 | 2014-03-05 | 李厚民 | Organically soluble photosensitive resin after being cured and preparation method and dissolving method thereof |
-
2014
- 2014-03-27 CN CN201410116890.2A patent/CN103941543B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4952481A (en) * | 1985-02-12 | 1990-08-28 | Napp Systems (Usa), Inc. | Photosensitive resin composition |
| CN101833241A (en) * | 2009-03-09 | 2010-09-15 | 村上精密制版（昆山）有限公司 | Photosensitive resin composition |
| CN102732094A (en) * | 2012-05-21 | 2012-10-17 | 史海生 | LED-UV surface light source light-curing silk-screen printing ink composition and preparation method thereof |
| CN103246164A (en) * | 2013-06-04 | 2013-08-14 | 苏州太速雷电子科技有限公司 | Photosensitive resin for stereo lithography forming and preparation method thereof |
| CN103616799A (en) * | 2013-11-07 | 2014-03-05 | 李厚民 | Organically soluble photosensitive resin after being cured and preparation method and dissolving method thereof |
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| CN103941543A (en) | 2014-07-23 |
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