CN104479098A - Preparation method of polyfunctional UV (Ultraviolet)-cured organic silicon resin - Google Patents
Preparation method of polyfunctional UV (Ultraviolet)-cured organic silicon resin Download PDFInfo
- Publication number
- CN104479098A CN104479098A CN201410796379.1A CN201410796379A CN104479098A CN 104479098 A CN104479098 A CN 104479098A CN 201410796379 A CN201410796379 A CN 201410796379A CN 104479098 A CN104479098 A CN 104479098A
- Authority
- CN
- China
- Prior art keywords
- preparation
- silicone resin
- organic silicon
- reaction
- silicon resin
- Prior art date
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
- C08G18/673—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen containing two or more acrylate or alkylacrylate ester groups
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Silicon Polymers (AREA)
Abstract
The invention relates to a preparation method of polyfunctional UV (Ultraviolet)-cured organic silicon resin. The preparation method comprises the steps: enabling aliphatic polyisocyanate containing three or more than three isocyanate groups to react with a silane coupling agent for 1.5 hours while heating and agitating under the temperature of 45 DEG C and in the presence of a catalyst to obtain a product (A); heating to reach the temperature of 50 DEG C; feeding a monomer which contains -OH and -C=C groups and has molecular weight less than or equal to 1000 to the reaction system while heating and agitating in the presence of the catalyst, so as to continuously react with the product (A) to obtain a product (B) which is the polyfunctional UV-cured organic silicon resin. With the adoption of the preparation method, the disadvantage of high temperature curing of the organic silicon resin can be solved; a plurality of double-bond structures are formed at the chain end of the prepared polymer, and therefore, the prepared resin can be subjected to UV curing under the room temperature, and meanwhile, the same performances can be achieved, such as heat resistance, weather resistance and mechanical property.
Description
Technical field
The present invention relates to a kind of preparation method of polyfunctionality UV cured silicone resin, belong to photo-cured coating field.
Background introduction
UV is coating material solidified is a kind of new green environment protection type coating, has and pollutes the advantages such as little, energy consumption is low, set time is short.UV is coating material solidified primarily of prepolymer, reactive monomer, light trigger and auxiliary agent composition, and wherein prepolymer constitutes the skeleton of cured film cross-linked structure, and it is the main determining factor of product physical and chemical performance.Tradition silicone resin generally all needs hot setting (150 ~ 200 DEG C), and when set time is long, large-area construction is inconvenient, temperature poor to the poor adhesive force of bottom, organic solvent resistance is higher, the physical strength of paint film is bad.The modification UV cured silicone resin adopting the monomeric aliphatic isocyanate such as hexamethylene diisocyanate trimer (HDT), pentaerythritol triacrylate (PETA), Hydroxyethyl acrylate (HEMA), Acrylic Acid Monomer obtained is compared with traditional silicone resin, there is higher sticking power, wear resistance, oil-proofness and chemical-resistant, and chain end has a large amount of double bond structure, can at room temperature solidify by UV, heat-resisting, weather resistance is good, has great potential in photo-cured coating field.
Summary of the invention
The present invention relates to a kind of preparation method of polyfunctionality UV cured silicone resin, its object is to provide a kind of utilize isocyanic ester and Acrylic Acid Monomer modified synthesis there is moderate molecular weight and the silicone resin of the resistance toheat of excellence.In this polymkeric substance, the polymkeric substance end of the chain has a large amount of double bond structure, and this makes prepared resin at room temperature can carry out UV solidification, avoids the shortcoming that traditional silicone resin needs hot setting, and identical performance can be reached equally, as thermotolerance, weathering resistance, mechanical property etc.
Technical scheme of the present invention is:
The preparation method of polyfunctionality UV cured silicone resin, comprises the steps:
(1) isocyanic ester used, Acrylic Acid Monomer are carried out processed;
(2) in molfraction, add in the four-hole boiling flask of dried and clean by the HDT monomer of 2 parts of molal weights, add tertiary amines or organometallics class catalyzer, stirred at ambient temperature is even;
(3) by above-mentioned four-hole boiling flask as in oil bath pan, and reaction system is warming up to 45 DEG C, the speed of often dripping with 2s drips the KH550 of a molal weight, Keep agitation, reaction 1.5h;
(4) after first stage reaction terminates, the speed of often dripping with 2s continues the PETA of 4 ~ 5 parts of molal weights to drop to reaction system, and is warming up to 50 DEG C, and reaction 1.5h, obtains a kind of polyfunctionality UV cured silicone resin.
Embodiment
Embodiment 1
0.01g catalyzer DBTDL and 112.08gHDT is added in clean four-hole boiling flask, insert thermometer, stirring rod, stir 30 minutes, by flask as in 45 DEG C of oil bath pans, constant pressure liquid water clock bucket is utilized the speed that 22.60gKH550 often drips with 2s slowly to be joined in four-hole boiling flask, after titration, Keep agitation reaction 1.5h.
Oil bath pan is warming up to 50 DEG C, utilize constant pressure liquid water clock bucket to continue 123.01gPETA to be added drop-wise in reaction system with the speed that 2s often drips, after titration, stirring reaction 1.5h, obtains required polyfunctionality UV cured silicone resin, i.e. product.
Embodiment 2
0.01g catalyzer DBTDL and 112.08gHDT is added in clean four-hole boiling flask, insert thermometer, stirring rod, stir 30 minutes, by flask as in 45 DEG C of oil bath pans, constant pressure liquid water clock bucket is utilized the speed that 22.60gKH550 often drips with 2s slowly to be joined in four-hole boiling flask, after titration, Keep agitation reaction 1.5h.
Oil bath pan is warming up to 50 DEG C, utilizes constant pressure liquid water clock bucket to continue 536.66gHEMA to be added drop-wise in reaction system with the speed that 2s often drips, after titration, reaction 1.5h, obtains required polyfunctionality UV cured silicone resin, i.e. product.
Claims (2)
1. a preparation method for polyfunctionality UV cured silicone resin, its characterization step is:
(1) isocyanic ester used, Acrylic Acid Monomer are carried out processed;
(2) in molfraction, add in the four-hole boiling flask of dried and clean by the HDT monomer of 2 parts of molal weights, add tertiary amines or organometallics class catalyzer, stirred at ambient temperature is even;
(3) by four-hole boiling flask as in oil bath pan, and reaction system is warming up to 45 DEG C, the speed of often dripping with 2s drips the KH550 of a molal weight, Keep agitation, reaction 1.5h;
(4), after first stage reaction terminates, the speed continuation of often dripping with about 2s drops to reaction system by the hydroxyl of 4 ~ 5 parts of molal weights and containing the function monomer of a large amount of double bond, and is warming up to 50 DEG C, and reaction 1.5h, obtains the modified organic silicone resin designed.
2. the preparation method of a kind of polyfunctionality UV cured silicone resin as claimed in claim 1, is characterized in that:
Hydroxyl described in step (4) and be at least one in hydroxyethyl methylacrylate (HEMA), Hydroxyethyl acrylate (HEA), pentaerythritol triacrylate (PETA) containing the function monomer of a large amount of double bond.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410796379.1A CN104479098A (en) | 2014-12-19 | 2014-12-19 | Preparation method of polyfunctional UV (Ultraviolet)-cured organic silicon resin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410796379.1A CN104479098A (en) | 2014-12-19 | 2014-12-19 | Preparation method of polyfunctional UV (Ultraviolet)-cured organic silicon resin |
Publications (1)
Publication Number | Publication Date |
---|---|
CN104479098A true CN104479098A (en) | 2015-04-01 |
Family
ID=52753714
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410796379.1A Pending CN104479098A (en) | 2014-12-19 | 2014-12-19 | Preparation method of polyfunctional UV (Ultraviolet)-cured organic silicon resin |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104479098A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105348867A (en) * | 2015-12-16 | 2016-02-24 | 江南大学 | Modification method of nano aluminium oxide |
CN109777121A (en) * | 2018-12-18 | 2019-05-21 | 中科院广州化学有限公司南雄材料生产基地 | A kind of preparation method of ultraviolet curing organic silicon wear resistant resin |
CN110054755A (en) * | 2019-04-24 | 2019-07-26 | 广东东田转印新材料有限公司 | It is a kind of can the UV resin of surface drying, preparation method and applications |
CN111040726A (en) * | 2019-12-26 | 2020-04-21 | 烟台德邦科技有限公司 | UV (ultraviolet) moisture dual-curing organic silicon coating adhesive |
CN111655747A (en) * | 2018-01-25 | 2020-09-11 | 莫门蒂夫性能材料有限责任公司 | Thiol-ene curable composition |
CN114133572A (en) * | 2022-01-06 | 2022-03-04 | 江南大学 | Photosensitive organic silicon resin, preparation method and application |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101034258A (en) * | 2006-10-25 | 2007-09-12 | 深圳市飞世尔实业有限公司 | Liquid light curing resin composition |
CN101942192A (en) * | 2010-09-14 | 2011-01-12 | 江南大学 | Method for preparing siloxane and nano silicon dioxide double modified ultraviolet curing aqueous polyurethane dispersion |
CN102002316A (en) * | 2010-12-03 | 2011-04-06 | 广东盈然木业有限公司 | UV-water-wet finish paint and floor produced thereby |
-
2014
- 2014-12-19 CN CN201410796379.1A patent/CN104479098A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101034258A (en) * | 2006-10-25 | 2007-09-12 | 深圳市飞世尔实业有限公司 | Liquid light curing resin composition |
CN101942192A (en) * | 2010-09-14 | 2011-01-12 | 江南大学 | Method for preparing siloxane and nano silicon dioxide double modified ultraviolet curing aqueous polyurethane dispersion |
CN102002316A (en) * | 2010-12-03 | 2011-04-06 | 广东盈然木业有限公司 | UV-water-wet finish paint and floor produced thereby |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105348867A (en) * | 2015-12-16 | 2016-02-24 | 江南大学 | Modification method of nano aluminium oxide |
CN111655747A (en) * | 2018-01-25 | 2020-09-11 | 莫门蒂夫性能材料有限责任公司 | Thiol-ene curable composition |
JP2021512192A (en) * | 2018-01-25 | 2021-05-13 | モメンティブ パフォーマンス マテリアルズ ゲーエムベーハーMomentive Performance Materials GmbH | Thiol-en curing composition |
CN111655747B (en) * | 2018-01-25 | 2022-07-05 | 莫门蒂夫性能材料有限责任公司 | Thiol-ene curable composition |
US11827738B2 (en) | 2018-01-25 | 2023-11-28 | Momentive Performance Materials Gmbh | Thiol-ene-curing compositions |
CN109777121A (en) * | 2018-12-18 | 2019-05-21 | 中科院广州化学有限公司南雄材料生产基地 | A kind of preparation method of ultraviolet curing organic silicon wear resistant resin |
CN110054755A (en) * | 2019-04-24 | 2019-07-26 | 广东东田转印新材料有限公司 | It is a kind of can the UV resin of surface drying, preparation method and applications |
CN110054755B (en) * | 2019-04-24 | 2021-04-20 | 广东东田转印新材料有限公司 | UV resin capable of being surface-dried, preparation method and application thereof |
CN111040726A (en) * | 2019-12-26 | 2020-04-21 | 烟台德邦科技有限公司 | UV (ultraviolet) moisture dual-curing organic silicon coating adhesive |
CN114133572A (en) * | 2022-01-06 | 2022-03-04 | 江南大学 | Photosensitive organic silicon resin, preparation method and application |
CN114133572B (en) * | 2022-01-06 | 2022-09-16 | 江南大学 | Photosensitive organic silicon resin, preparation method and application |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104479098A (en) | Preparation method of polyfunctional UV (Ultraviolet)-cured organic silicon resin | |
CN107793544B (en) | A kind of environment-friendly polyurethane curing agent and its preparation method and application | |
US8410229B2 (en) | Polyurethane-modified acrylic resin and preparing method thereof | |
CN101824299B (en) | Method for preparing single-component high-solid content water-based polyurethane adhesive | |
Ahn et al. | UV curable polyurethane dispersions from polyisocyanate and organosilane | |
CN102504174A (en) | Polyurethane acrylic acid ester and preparation method and application thereof | |
CN105778028B (en) | A kind of preparation method of abietyl TDI Type Polyurethane Prepolymers | |
CN105175641A (en) | Silane coupling agent modified polyurethane-acrylate composite emulsion and preparation method thereof | |
CN101274977A (en) | Curing agent 1,6- hexamethylene diisocyanate prepolymer and preparation thereof | |
CN103421462B (en) | High-initial-adhesion waterborne polyurethane adhesive and preparation method thereof | |
CN105482059A (en) | Method for preparing hydroxyl-terminated polybutadiene modified ultraviolet light curable waterborne polyurethane | |
CN104086742A (en) | Preparation method of acid and alkali resistant ultraviolet-curing adhesive film resin for glass base material | |
CN106700024A (en) | Preparation method of UV-curable polyurethane acrylate self-repair resin | |
CN104371086B (en) | A kind of preparation method of the organosilan acroleic acid polyurethane solidified for ultraviolet light | |
CN101186619A (en) | Modified polyisocyanates mixed trimer curing agent containing monoisocyanate alkyl alkoxy silicane and preparation method thereof | |
CN103073699B (en) | Polyurethane curing agent and preparation method thereof | |
CN104693371B (en) | Novel acrylic modified resin for aqueous two-component polyurethane coating | |
CN102010558B (en) | Acrylic acid non-aqueous dispersoid containing amino ester bonds and siloxy groups and preparation method thereof | |
CN103333318A (en) | Preparation method of polyurea acrylic ester | |
CN105646838B (en) | A kind of preparation method of newtrex based polyurethanes performed polymer | |
CN102391470A (en) | Preparation method for ionic liquid terminated polyurethane acrylate | |
CN103360940A (en) | Preparation method of ultraviolet light/humidity dual-cured high-weatherability organic silicon hybrid polyurethane resin | |
CN105585690A (en) | Method for preparing polydimethyl siloxane/hydroxyl-terminated polybutadiene modified UV curing hyperbranched polyurethane | |
CN104031467B (en) | A kind of preparation method of environment-friendly solvent type polyurethane ink | |
CN105238200B (en) | A kind of air drying type acrylate waterproof paint and preparation method thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20150401 |
|
RJ01 | Rejection of invention patent application after publication |