CN109777121A - A kind of preparation method of ultraviolet curing organic silicon wear resistant resin - Google Patents
A kind of preparation method of ultraviolet curing organic silicon wear resistant resin Download PDFInfo
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- CN109777121A CN109777121A CN201811546311.2A CN201811546311A CN109777121A CN 109777121 A CN109777121 A CN 109777121A CN 201811546311 A CN201811546311 A CN 201811546311A CN 109777121 A CN109777121 A CN 109777121A
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- resistant resin
- wear resistant
- organic silicon
- ultraviolet curing
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Abstract
The invention discloses a kind of preparation methods of ultraviolet curing organic silicon wear resistant resin, be by linear ultraviolet light prepolymer, hyper-branched prepolymers, photoinitiator according to mass ratio be (0.1~0.3): (0.7~0.9): (0.01~0.05) is reacted, solidify under room temperature and ultraviolet light conditions, obtains ultraviolet curing organic silicon wear resistant resin.The curing time of ultraviolet curing organic silicon wear resistant resin prepared by the present invention is short, and performance indexes is good, and specific formula can carry out proportion regulation according to product specific requirement.
Description
Technical field
The present invention relates to curing agent field, in particular to a kind of preparation method of ultraviolet curing organic silicon wear resistant resin.
Background technique
UV-curing technology is a kind of ion or freedom for generating upper state under ultraviolet light using photoinitiator
Base causes the technology of molecule reaction.Compared with traditional thermal booster reaction, UV-curing technology is with low energy consumption, the reaction time
The advantages that rapid, is widely used in fields such as coating, automobile, crosslinking agent, ink.The market demand of organosilicon is fast in recent years
Speed increases, and the development of organic siliconresin is also sharply increased with the market demand.Requirement of the modern industrial production for energy consumption is increasingly
Height, it is the inexorable trend developed in organic siliconresin that the UV-curing technology of Environmentally-frielow-energy-consumptipolycarboxylic low-energy-consumptipolycarboxylic, which is applied,.Organic siliconresin
Because of its relatively unique structure, the advantage of existing organic structure, and there is the characteristics of " inorganic structure ", it is made to have higher crosslinking close
Degree and higher hardness, there is good application prospect in wear-resistant material；But its higher density makes organic after solidifying again
The decline of the adhesive force of silicone resin and substrate.The high hardness wear-resisting performance phase collision problem small with adhesive force how is solved, is organic
Problem that one of silicone resin research is popular.Current such wear resistant resin mainly based on epoxy modification acrylate, is added with
Machine silicon crosslinking agent is auxiliary agent to form cross-linked network.But small molecule organosilicon cross-linking agent is mentioned for entire crosslink density and hardness
It rises very limited.The present invention starts with from the structure of resin, in the case where introducing adhesive force stronger group, keeps its crosslink density,
Resin is designed from molecule angle, structure is reflected and determines performance, the principle that performance requirement instructs structure to design in turn.
Summary of the invention
It is an object of the invention to overcome disadvantage existing in the prior art, a kind of environmental-friendly, at low cost, technique is provided
The preparation method of simple ultraviolet curing organic silicon wear resistant resin.
The purpose of the invention is achieved by the following technical solution:
A kind of preparation method of ultraviolet curing organic silicon wear resistant resin is by linear ultraviolet light prepolymer, hyperbranched pre-
Polymers, photoinitiator are (0.1~0.3) according to mass ratio: (0.7~0.9): (0.01~0.05) is reacted, in room temperature and
Solidify under ultraviolet light conditions, obtains ultraviolet curing organic silicon wear resistant resin.
The linear ultraviolet light prepolymer is prepared using following methods:
(1) isophorone diisocyanate, pentaerythritol triacrylate, dibutyltin dilaurate catalyst by mole
Than for 1:(2~3): (0.001~0.05) is reacted, and the substance that both ends are polyfunctional acrylic ester structure is obtained；
(2) be the substance of polyfunctional acrylic ester structure by both ends, end hydrogen silicone oil, chloroplatinic acid/aqueous isopropanol are catalyzed
Agent is in molar ratio (2~4): 1:(0.001~0.05) hydrosilylation is carried out, obtain linear ultraviolet light prepolymer.
The reaction temperature of step (1) is 30~90 DEG C.
In step (2), reaction temperature is 80~120 DEG C, and the reaction time is 3~6 hours.
In step (2), chloroplatinic acid/aqueous isopropanol catalyst is the aqueous isopropanol of chloroplatinic acid, the concentration model of chloroplatinic acid
It encloses for 0.03mol/L~0.07mol/L.
In step (2), the molecular weight of end hydrogen silicone oil is 2000~8000, preferred molecular weight 2000,4000 or 8000.
The hyper-branched prepolymers be two kinds have different functional groups, same hydrolysis group silane coupling agent in hydrochloric acid catalysis
Lower hydrolysis is made.
The silane coupling agent be molar ratio be 1:(0.4~1) 3- methyl allyl acyloxypropyl trimethoxysilane and
The mixture of trifluoro propane trimethoxy silane.
The hyper-branched prepolymers are prepared using following methods: deionization being added in silane coupling agent and goes, so
Adjusting pH value range with hydrochloric acid afterwards is 1~2, and reaction is hydrolyzed, and hydrolysis temperature is 50~80 DEG C, the time 3~5 hours.
The molar ratio of silane coupling agent and water is 1:(1.1~1.5).
The photoinitiator is 2,4,6- trimethylbenzoy-dipheny phosphine oxide (TPO), 2,4,6- trimethylbenzene first
It is acyl phosphonic acid ethyl ester (TOP-L), 1- hydroxyl-cyclohexyl-phenyl ketone, a kind of in 2- hydroxy-2-methyl -1- phenyl -1- acetone
Or a variety of mixtures.
The present invention has the following advantages that compared with prior art and effect:
(1) curing time of ultraviolet curing organic silicon wear resistant resin prepared by the present invention is short, and performance indexes is good,
Specific formula can carry out proportion regulation according to product specific requirement.
(2) specific steps of the invention are simple, and actual mechanical process is also easier, and it is solid to solve light to a certain extent
Change the poor problem of wear resistant resin adhesive force.
Specific embodiment
Further detailed description is done to the present invention below with reference to embodiment, embodiments of the present invention are not limited thereto.
Embodiment 1
By isophorone diisocyanate, pentaerythritol triacrylate, dibutyl tin dilaurate 1:2 in molar ratio:
0.01 mixing, reaction temperature are 50 DEG C, and the substance that both ends are polyfunctional acrylic ester structure is made.It is polyfunctionality by both ends
The substance of acrylate structural, the end hydrogen silicone oil that molecular weight is 2000, chloroplatinic acid/aqueous isopropanol catalyst are (in terms of pt atom
Calculate) in molar ratio 2.5:1:0.01 in 80~110 DEG C of reactions linear ultraviolet light prepolymer is made.
3- methyl allyl acyloxypropyl trimethoxysilane, trifluoro propane trimethoxy silane 1:0.4 in molar ratio, silane
The molar ratio of coupling agent total amount and water is 1:1.2, and salt acid for adjusting pH is added and reacts 3~4 hours at 1~2,50~60 DEG C, system
Obtain hyper-branched prepolymers.Selecting 1- hydroxyl-cyclohexyl-phenyl ketone is photoinitiator, linear ultraviolet light prepolymer, hyperbranched pre-polymerization
Object, photoinitiator mass ratio for 0.3:0.7:0.03 mixing, ultraviolet lighting after coating.Adhesion property reaches 1 grade.It is resistance to
It grinds functional.
Embodiment 2
By isophorone diisocyanate, pentaerythritol triacrylate, dibutyl tin dilaurate 1:2 in molar ratio:
0.03 mixing, reaction temperature are 60 DEG C, and the substance that both ends are polyfunctional acrylic ester structure is made.It is polyfunctionality by both ends
The substance of acrylate structural, the end hydrogen silicone oil that molecular weight is 4000, chloroplatinic acid/aqueous isopropanol catalyst are (in terms of pt atom
Calculate) in molar ratio 3:1:0.03 in 80~110 DEG C of reactions linear ultraviolet light prepolymer is made.
3- methyl allyl acyloxypropyl trimethoxysilane, trifluoro propane trimethoxy silane 1:0.6 in molar ratio, silane
The molar ratio of coupling agent total amount and water is 1:1.3, and salt acid for adjusting pH is added and reacts 3~4 hours at 1~2,50~60 DEG C, system
Obtain hyper-branched prepolymers.Selecting 2- hydroxy-2-methyl -1- phenyl -1- acetone is photoinitiator, linear ultraviolet light prepolymer, over-expense
Change prepolymer, the mass ratio of photoinitiator is 0.2:0.8:0.03, ultraviolet lighting after coating.Adhesion property reaches 1 grade.
Wear-resisting property is good.
Embodiment 3
By isophorone diisocyanate, pentaerythritol triacrylate, dibutyl tin dilaurate 1:3 in molar ratio:
0.04 mixing, reaction temperature are 60 DEG C, and the substance that both ends are polyfunctional acrylic ester structure is made.It is polyfunctionality by both ends
The substance of acrylate structural, the end hydrogen silicone oil that molecular weight is 4000, chloroplatinic acid/aqueous isopropanol catalyst are (in terms of pt atom
Calculate) in molar ratio 4:1:0.05 in 80~110 DEG C of reactions linear ultraviolet light prepolymer is made.
1:1, silane are even in molar ratio for 3- methyl allyl acyloxypropyl trimethoxysilane, trifluoro propane trimethoxy silane
The molar ratio for joining agent total amount and water is 1:1.5, and salt acid for adjusting pH is added and reacts 3~4 hours at 1~2,50~60 DEG C, is made
Hyper-branched prepolymers.Selecting the molar ratio of silane coupling agent total amount and water is 1:1.5, and TPO and TPO-L mixture is light-initiated
Agent, linear ultraviolet light prepolymer, hyper-branched prepolymers, photoinitiator mass ratio be 0.2:0.8:0.05, it is ultraviolet after coating
Illumination.Adhesion property reaches 2 grades.Wear-resisting property is good.
The above description is only an embodiment of the present invention, but embodiment of the present invention are not limited by the above embodiments,
It is other it is any without departing from the spirit and principles of the present invention made by changes, modifications, substitutions, combinations, simplifications, be
The substitute mode of effect, is included within the scope of the present invention.
Claims (10)
1. a kind of preparation method of ultraviolet curing organic silicon wear resistant resin, it is characterised in that: be by linear ultraviolet light prepolymer,
Hyper-branched prepolymers, photoinitiator are (0.1~0.3) according to mass ratio: (0.7~0.9): (0.01~0.05) is reacted,
Solidify under room temperature and ultraviolet light conditions, obtains ultraviolet curing organic silicon wear resistant resin.
2. the preparation method of ultraviolet curing organic silicon wear resistant resin according to claim 1, it is characterised in that: the line
Property ultraviolet light prepolymer is prepared using following methods:
(1) isophorone diisocyanate, pentaerythritol triacrylate, dibutyltin dilaurate catalyst are in molar ratio
1:(2~3): (0.001~0.05) is reacted, and the substance that both ends are polyfunctional acrylic ester structure is obtained；
(2) substance, end hydrogen silicone oil, chloroplatinic acid/aqueous isopropanol catalyst that both ends are polyfunctional acrylic ester structure are pressed
Molar ratio (2~4): 1:(0.001~0.05) hydrosilylation is carried out, obtain linear ultraviolet light prepolymer.
3. the preparation method of ultraviolet curing organic silicon wear resistant resin according to claim 2, it is characterised in that: step
(1) reaction temperature is 30~90 DEG C；In step (2), reaction temperature is 80~120 DEG C, and the reaction time is 3~6 hours.
4. the preparation method of ultraviolet curing organic silicon wear resistant resin according to claim 2, it is characterised in that: step
(2) in, chloroplatinic acid/aqueous isopropanol catalyst is the aqueous isopropanol of chloroplatinic acid, and the concentration range of chloroplatinic acid is 0.03mol/L
~0.07mol/L.
5. the preparation method of ultraviolet curing organic silicon wear resistant resin according to claim 2, it is characterised in that: step
(2) in, the molecular weight of end hydrogen silicone oil is 2000~8000.
6. the preparation method of ultraviolet curing organic silicon wear resistant resin according to claim 1, it is characterised in that: described super
Branching prepolymer has different functional groups for two kinds, the silane coupling agent of same hydrolysis group is hydrolyzed under hydrochloric acid catalysis and is made.
7. the preparation method of ultraviolet curing organic silicon wear resistant resin according to claim 6, it is characterised in that: the silicon
Alkane coupling agent be molar ratio be 1:(0.4~1) 3- methyl allyl acyloxypropyl trimethoxysilane and trifluoro propane trimethoxy
The mixture of base silane.
8. the preparation method of ultraviolet curing organic silicon wear resistant resin according to claim 6, it is characterised in that: described super
Branching prepolymer is prepared using following methods: deionization being added in silane coupling agent and goes, then uses salt acid for adjusting pH
Being worth range is 1~2, and reaction is hydrolyzed, and hydrolysis temperature is 50~80 DEG C, the time 3~5 hours.
9. the preparation method of ultraviolet curing organic silicon wear resistant resin according to claim 8, it is characterised in that: silane is even
The molar ratio for joining agent and water is 1:(1.1~1.5).
10. the preparation method of ultraviolet curing organic silicon wear resistant resin according to claim 1, it is characterised in that: described
Photoinitiator is 2,4,6- trimethylbenzoy-dipheny phosphine oxide, 2,4,6- trimethylbenzoyl phosphinic acid ethyl ester, 1- hydroxyl
One or more mixtures in base-cyclohexyl-phenyl ketone, 2- hydroxy-2-methyl -1- phenyl -1- acetone.
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| CN201811546311.2A CN109777121A (en) | 2018-12-18 | 2018-12-18 | A kind of preparation method of ultraviolet curing organic silicon wear resistant resin |
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| CN201811546311.2A CN109777121A (en) | 2018-12-18 | 2018-12-18 | A kind of preparation method of ultraviolet curing organic silicon wear resistant resin |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698911A (en) * | 2019-11-24 | 2020-01-17 | 邵美忠 | Double-curing glass printing ink and preparation method thereof |
| CN110760260A (en) * | 2019-11-24 | 2020-02-07 | 邵美忠 | Dual-curing vacuum coating primer and preparation method thereof |
| CN110790936A (en) * | 2019-11-24 | 2020-02-14 | 邵美忠 | Dual-curing organic silicon resin and preparation method thereof |
| CN111234773A (en) * | 2020-03-10 | 2020-06-05 | 烟台德邦科技有限公司 | Silicone sealant with high environmental adaptability |
| CN116042083A (en) * | 2022-12-21 | 2023-05-02 | 长飞光纤光缆股份有限公司 | Silane modified low-refractive-index optical fiber coating |
| CN117285879A (en) * | 2023-11-24 | 2023-12-26 | 江苏凯伦建材股份有限公司 | Pre-laid waterproof coiled material and preparation method thereof |
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| JP2009102628A (en) * | 2007-10-01 | 2009-05-14 | Atomix Co Ltd | Ultraviolet radiation-curable coating composition and method for producing the same, and coated resin product coated with the same |
| CN104479098A (en) * | 2014-12-19 | 2015-04-01 | 江南大学 | Preparation method of polyfunctional UV (Ultraviolet)-cured organic silicon resin |
| CN105418928A (en) * | 2015-12-29 | 2016-03-23 | 广东恒大新材料科技有限公司 | Trifluoropropyl-group-modification methyl phenyl vinyl silicon resin and LED packaging adhesive |
| CN108586754A (en) * | 2018-05-14 | 2018-09-28 | 中科广化（重庆）新材料研究院有限公司 | A kind of hyperbranched silicone acrylic resin and the preparation method and application thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2009102628A (en) * | 2007-10-01 | 2009-05-14 | Atomix Co Ltd | Ultraviolet radiation-curable coating composition and method for producing the same, and coated resin product coated with the same |
| CN104479098A (en) * | 2014-12-19 | 2015-04-01 | 江南大学 | Preparation method of polyfunctional UV (Ultraviolet)-cured organic silicon resin |
| CN105418928A (en) * | 2015-12-29 | 2016-03-23 | 广东恒大新材料科技有限公司 | Trifluoropropyl-group-modification methyl phenyl vinyl silicon resin and LED packaging adhesive |
| CN108586754A (en) * | 2018-05-14 | 2018-09-28 | 中科广化（重庆）新材料研究院有限公司 | A kind of hyperbranched silicone acrylic resin and the preparation method and application thereof |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110698911A (en) * | 2019-11-24 | 2020-01-17 | 邵美忠 | Double-curing glass printing ink and preparation method thereof |
| CN110760260A (en) * | 2019-11-24 | 2020-02-07 | 邵美忠 | Dual-curing vacuum coating primer and preparation method thereof |
| CN110790936A (en) * | 2019-11-24 | 2020-02-14 | 邵美忠 | Dual-curing organic silicon resin and preparation method thereof |
| CN111234773A (en) * | 2020-03-10 | 2020-06-05 | 烟台德邦科技有限公司 | Silicone sealant with high environmental adaptability |
| CN111234773B (en) * | 2020-03-10 | 2021-09-17 | 烟台德邦科技股份有限公司 | Silicone sealant with high environmental adaptability |
| CN116042083A (en) * | 2022-12-21 | 2023-05-02 | 长飞光纤光缆股份有限公司 | Silane modified low-refractive-index optical fiber coating |
| CN117285879A (en) * | 2023-11-24 | 2023-12-26 | 江苏凯伦建材股份有限公司 | Pre-laid waterproof coiled material and preparation method thereof |
| CN117285879B (en) * | 2023-11-24 | 2024-02-27 | 江苏凯伦建材股份有限公司 | Pre-laid waterproof coiled material and preparation method thereof |
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Application publication date: 20190521 |