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CN-121991633-A - UV/moisture dual-curing composition, preparation method and application thereof

CN121991633ACN 121991633 ACN121991633 ACN 121991633ACN-121991633-A

Abstract

The invention discloses a UV/moisture dual-curing organic silicon resin composition and a preparation method thereof. The composition comprises (A) 85-96 wt% of acrylic modified silicone resin, (B) 0.5-2 wt% of photoinitiator, (C) 1-5 wt% of acrylic diluent, (D) 0.5-2 wt% of organic metal catalyst, (E) 1-5 wt% of polyether modified silicone oil and (F) 0.02-1 wt% of auxiliary agent. The composition has the characteristics of good storage stability, deep curing depth, low light curing energy, high curing efficiency, good protective performance and the like.

Inventors

  • SU WENLU
  • GAO YUAN
  • WANG HU
  • FENG LINGLONG
  • XIN SHAOHUI

Assignees

  • 万华化学集团股份有限公司

Dates

Publication Date
20260508
Application Date
20241108

Claims (10)

  1. 1. A UV/moisture dual cure silicone resin composition comprising the following components: (A) Acrylic modified silicone resin, content 85-96wt%; (B) A photoinitiator in an amount of 0.5 to 2wt%; (C) Acrylic ester diluent with the content of 1-5wt%; (D) 0.5-2wt% of an organometallic catalyst; (E) 1-5wt% of polyether modified silicone oil; (F) 0.02-1wt% of auxiliary additive.
  2. 2. The UV/moisture dual cure silicone resin composition of claim 1, wherein said component a is of the structure of formula I and/or formula II: Wherein R 1 、R 2 、R 3 、R 4 、R 5 、R 6 each independently represents a hydrogen atom, a C1-C10 alkyl group, an aromatic hydrocarbon group, an alkenyl group, preferably a methyl group, wherein a and b refer to the degree of polymerization, and the values of a=100-450, b=100-450, preferably a=200-300, and b=200-300, respectively.
  3. 3. UV/moisture dual cure silicone resin composition according to claim 1 or 2, characterized in that said component B is selected from one or more of 2-methyl-1- [4- (methylthio) phenyl ] -2- (4-morpholinyl) -1-propanone (aka 907), 2-phenylbenzyl-2-dimethylamine-1- (4-morpholinylphenyl) butanone (aka 369), diphenyl- (2, 4, 6-trimethylbenzoyl) phosphorus oxide (aka TPO), ethyl 2,4, 6-trimethylbenzoyl phenylphosphonate (aka TPO-L), phenylbis (2, 4, 6-trimethylbenzoyl) phosphine oxide (aka 819), 2-isopropylthioxanthone (aka ITX), 2, 4-diethylthioxanthone (aka DETX), 2-chlorothioxanthone (aka CTX), 1-chloro-4-propylthioxanthone (aka CPTX).
  4. 4. A UV/moisture dual cure silicone resin composition according to any one of claims 1-3, wherein said component C is selected from one or more of 1, 6-hexanediol diacrylate (otherwise known as HDDA), tripropylene glycol diacrylate (otherwise known as TPGDA), trimethylolpropane triacrylate (otherwise known as TMPTA), 2-phenylethyl acrylate (otherwise known as PEA).
  5. 5. The UV/moisture dual cure silicone resin composition according to any one of claims 1-4, wherein component D is selected from one or more of dibutyltin dilaurate, stannous octoate, diisopropyl bis (acetoacetate) titanate, tetra-t-butyl titanate, bismuth iso-octoate, bismuth laurate.
  6. 6. The UV/moisture dual cure silicone resin composition of any one of claims 1-5, wherein said component E has a structure as shown in formula III: Wherein R 7 、R 8 each independently represents a hydrogen atom or an alkyl group, an alkoxy group, an aromatic hydrocarbon group or an alkenyl group having 1 to 20 carbon atoms, R 9 represents a hydrogen atom or an alkyl group, an alkyl ester group or an epoxy group having 1 to 5 carbon atoms, wherein m, n, o, p, x, y, z each represents a degree of polymerization in the range of m=0 to 10, n=1 to 40, o=40 to 400, p=1 to 10, x=1 to 20, y=0 to 20, z=1 to 10, preferably m=0 to 4, n=1 to 10, o=50 to 100, p=1 to 3, x=5 to 10, y=0 to 5, and z=1 to 5, respectively.
  7. 7. The UV/moisture dual cure silicone resin composition of any one of claims 1-6, wherein component F comprises one or more of a stabilizer, a water scavenger, a thixotropic agent, and an optical brightening agent. The stabilizer is one or more selected from hydroquinone, p-hydroxyanisole, 2, 6-di-tert-butyl p-cresol, 2, 6-di-tert-butyl hydroquinone and 2-tert-butyl hydroquinone, the water scavenger is one or more selected from methyltrimethoxysilane and vinyltrimethoxysilane, the thixotropic agent is hydrophobic fumed silica, and the fluorescent whitening agent is fluorescent whitening agent OB.
  8. 8. A process for preparing a UV/moisture dual cure silicone resin composition as set forth in any one of claims 1-7, said process comprising the steps of: (1) Mixing the component A and the component E, carrying out reduced pressure dehydration, and sealing for later use; (2) Mixing the component B with the component C to completely dissolve the component B in the component C; (3) And sequentially adding the dehydrated mixed solution of the component A and the component E, the mixed solution of the component B and the component C, the component D and the component F into a reactor in a nitrogen atmosphere, and mixing to obtain the UV/moisture dual-curing organic silicon resin composition.
  9. 9. The process according to claim 8, wherein the temperature for the reduced pressure dehydration of the mixing of component A with component E in step (1) is 50-100 ℃, preferably 60-80 ℃, the pressure is 10-100mbar, preferably 40-60mbar, the time is 0.5-3 hours, preferably 1-2 hours, and/or the mixing temperature of component B with component C in step (2) is 20-50 ℃, preferably 30-40 ℃, the mixing speed is 100-400rpm, preferably 200-300rpm, the mixing time is 10-50min, preferably 30-40min, and/or the mixing temperature of the components in step (3) in a reactor under nitrogen atmosphere is 10-40 ℃, preferably 20-35 ℃, the mixing speed is 100-400rpm, preferably 200-300rpm, the mixing time is 0.5-3 hours, preferably 1-2 hours.
  10. 10. Use of a UV/moisture dual cure silicone resin composition as defined in any one of claims 1-7 or a UV/moisture dual cure silicone resin composition prepared by a method as defined in any one of claims 8 or 9 for the protection of packaging or circuit pads of electronic products or for the bonding of materials such as metals, glass, plastics and the like.

Description

UV/moisture dual-curing composition, preparation method and application thereof Technical Field The invention relates to an organosilicon coating adhesive, in particular to a UV/moisture dual-curing composition, a preparation method and application thereof. Background The organic silicon material has excellent performances of high and low temperature resistance, weather resistance, corrosion resistance, physiological inertia and the like, and is widely applied to the adhesion and sealing protection of structural elements, optical elements and electrical and electronic elements. The UV/moisture dual cure technique combines the advantages of rapid prototyping for UV curing and dark space curing for moisture curing. The problems of long curing time, low efficiency and high cost of the pure moisture curing technology are solved, the problem that the UV curing technology cannot cure in a dark area at a complex structure is solved, and the application scene is widened. Therefore, development and application of the UV/moisture dual-curing material, in particular development and application of the organosilicon UV/moisture dual-curing material, have higher application value and market value. However, the conventional UV/moisture dual-curing composition has the characteristic of poor storage stability due to the incompatibility of the moisture curing catalyst and the acrylate diluent with the main component siloxane, and is easy to cause problems of gel, delamination, precipitation of a photoinitiator and the like in the storage process, so that the performance loss in various aspects is serious in use, and the service life and the application of the UV/moisture dual-curing composition are limited. Patent CN112062964a proposes a UV/moisture dual cure composition and a process for the preparation of an acrylate-polysiloxane material, the main structure containing both isocyanate and alkoxy silicon groups, achieving UV/moisture dual cure. The obtained polysiloxane material has the advantages of regular and single structure, good transparency and good storage stability at room temperature, and reduces the problem that the UV/moisture dual-curing composition is easy to gel in the production and storage processes. However, the production process of the acrylate-polysiloxane material adopts solution polymerization and ethanol washing, and mass production is difficult to realize, so that the application range is limited. The patent CN111471425B adds polyether polyurethane oligomer with (methyl) acryloxy and alkoxy silane functional groups into the UV/moisture dual-curing composition, improves the system compatibility, improves the storage performance of the composition, and has the characteristics of high adhesive strength, good storage stability, safety, environmental protection and the like. However, the method improves the storage performance, and simultaneously, the reduction of the siloxane content can lead to the reduction of the weather resistance of the coating of the product, thereby affecting the protection performance of the coating on structural elements, optical elements and electrical and electronic elements. Therefore, there is a need to provide a UV/moisture dual-cure composition that efficiently solves the problem of storage stability, maintains adhesion, protection, and weather resistance properties of the product, prolongs the service life of the UV/moisture dual-cure composition, and widens the use applications of the UV/moisture dual-cure composition. Disclosure of Invention In order to solve the technical problems, the invention provides a UV/moisture dual-curing organic silicon resin composition, a preparation method and application thereof. The composition has the characteristics of good storage stability, deep curing depth, low photo-curing energy, high curing efficiency and good protective performance, and has effective service performance after long-time storage. In one aspect, the present invention provides a UV/moisture dual cure silicone resin composition comprising the following components: (A) Acrylic modified silicone resin, content 85-96wt%; (B) A photoinitiator in an amount of 0.5 to 2wt%; (C) Acrylic ester diluent with the content of 1-5wt%; (D) 0.5-2wt% of an organometallic catalyst; (E) 1-5wt% of polyether modified silicone oil; (F) 0.02-1wt% of auxiliary additive. As a preferred scheme of the invention, the structure of the component A is shown as a formula I and/or a formula II: Wherein R 1、R2、R3、R4、R5、R6 each independently represents a hydrogen atom, a C1-C10 alkyl group, an aromatic hydrocarbon group, an alkenyl group, preferably a methyl group, wherein a and b refer to the degree of polymerization, and the values of a=100-450, b=100-450, preferably a=200-300, and b=200-300, respectively. As a preferred scheme of the invention, the preparation method of the component A is as follows: (1) Adding hydroxyl silicone oil and methacryloxypropyl trimethoxysilane (or acryloxypropyl trimeth