CN104193996A - UV (ultraviolet)/moisture-curing organic silicon glue - Google Patents
UV (ultraviolet)/moisture-curing organic silicon glue Download PDFInfo
- Publication number
- CN104193996A CN104193996A CN201410414947.7A CN201410414947A CN104193996A CN 104193996 A CN104193996 A CN 104193996A CN 201410414947 A CN201410414947 A CN 201410414947A CN 104193996 A CN104193996 A CN 104193996A
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- Prior art keywords
- moisture
- dual cure
- polymkeric substance
- organosilicon glue
- moisture dual
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- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
- C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Silicon Polymers (AREA)
Abstract
The invention provides a UV (ultraviolet)/moisture-curing organic silicon glue which is prepared from the following raw materials in parts by weight: 97-98 parts of polymer and 2-3 parts of photoinitiator. The UV/moisture-curing organic silicon glue belongs to a single component, can generate curing reaction in the presence of ultraviolet light and also generate moisture curing reaction, and can generate moisture curing crosslinking reaction under the condition of no ultraviolet light. The polymer contains the double bond and polysiloxane capable of photocuring, and also contains the alkoxy and epoxy groups capable of moisture curing and enhancing the bonding force with the substrate.
Description
Technical field
The present invention relates to the two cure polymers of a kind of UV/ moisture and the two cured silicone glue of UV/ moisture, belong to silicon materials field.
Background technology
Organosilicon special construction has the performance of many excellences, as high-low temperature resistant, weather-proof, ageing-resistant, corrosion-resistant, low surface tension and physiology inertia etc., thereby it is all widely used at aspects such as aerospace, electric, chemical industry, communications and transportation, health care, daily lifes.
UV-curing technology is the new technology that the eighties is risen.Have quick solidifying, energy-conservation, ambient cure, pollution less, the advantage such as superior performance, be new generation of green Chemicals.Along with the increase of UV solidifying product demand, acrylate has been carried out to various modifications, as polyurethane-modified, epoxide modified etc., and Photocurable Silicone Material is owing to having excellent properties and efficient, the energy-conservation feature of photocuring technology of organosilicon material concurrently, and enjoy favor, and be progressively used widely.The combination of organosilicon material and photocuring technology, not only makes the application extension of organosilicon material arrive new field, and has increased new kind for photo-curing material.
Because the solidification process of photocuring system is by light-initiated, there is certain restriction for shape, thickness, the color of solidifying object, as dash area cannot be realized photocuring, thereby do not reach filling and the provide protection to various complicated type wiring boards.
Summary of the invention
The object of the invention is to overcome the glue curing time that prior art exists long, efficiency is low, and dash area and bottom part cannot photocuring shortcoming, a kind of UV/ moisture dual cure organosilicon glue is provided, make system fast shaping or reach most of surface drying with UV photocuring, simultaneously moisture-curable make shade or bottom partly solidified completely, thereby realize the completely curing of glue.
In order to realize object of the present invention, a kind of UV/ moisture dual cure organosilicon glue is proposed, its polymkeric substance had both contained two keys that can carry out photocuring, polysiloxane, containing again can moisture curing, improves alkoxyl group, epoxy group(ing) to substrate bonding power.
First the present invention discloses a kind of UV/ moisture dual cure polymkeric substance, and its structural formula is as shown in general formula (1), and wherein the span of m is 100-500,
The invention also discloses aforementioned polymer and prepare the purposes of UV/ moisture dual cure organosilicon glue.
Second aspect present invention discloses a kind of UV/ moisture dual cure organosilicon glue, and its raw material composition and each composition weight umber are as follows:
97～98 parts, polymkeric substance;
2～3 parts of light triggers;
The structural formula of described polymkeric substance is as shown in general formula (1), and the span of m is 100-500.
Further; shown in structural formula (1), the synthetic method of polymkeric substance is as follows: under nitrogen protection; in reactor, add 236g KH-560 and 248g KH-570; 6g stannous octoate; temperature of reaction kettle is elevated to 60 DEG C; stirring and dripping hydroxy radical content in downhill reaction still is 0.11%, the end hydroxyl silicone oil 10kg that viscosity is 1670mPa.s, and decompression (0.098MPa) simultaneously removes the methyl alcohol of generation.Drip and completed in 6 hours.After dropwising, temperature of reaction is risen to 80 DEG C, and continue Depressor response after 2 hours, the colourless transparent liquid that obtains viscosity and be 3000～4000mPa.s is polymkeric substance shown in structural formula (1).
Wherein, the structural formula of described end hydroxyl silicone oil is as shown in general formula (2):
Wherein the scope of n is 100-500.
Further; light trigger is selected from 1-hydroxyl-phenylcyclohexyl ketone, 2-hydroxy-2-methyl-phenyl-acetone-1,2,4,6-trimethylbenzoyl-oxyethyl group-phenyl phosphine oxide and 2; the mixing of one or more in 4,6-trimethylbenzoyl-diphenyl phosphine oxide.
The invention also discloses a kind of polymkeric substance of structural formula as shown in general formula (3):
And the span of x is 100-500.
The polymer phase ratio of the polymkeric substance of structural formula (1) and structural formula (3), structural formula (1) had both contained two keys, and containing again can moisture curing, improves alkoxyl group, the epoxy group(ing) of cementability; Structural formula (3) only contains two keys.Visible, structural formula (1) is as both can photocuring, polymkeric substance that again can moisture curing, and to base material sticking power excellence.
The invention also discloses the using method of aforementioned UV/ moisture dual cure organosilicon glue, obtain UV/ moisture dual cure organosilicon glue and for bonding or filling for the raw material composition according to described organosilicon glue mixes described polymkeric substance with described light trigger, and organosilicon glue is carried out to ultra-violet curing.
Further, the curing energy of described ultra-violet curing is 8000～9000mJ/cm
2.
The invention also discloses the application in the plate filling of the online road of aforementioned UV/ moisture dual cure organosilicon glue and protection.
UV/ moisture dual cure organosilicon glue of the present invention, belongs to single component, under UV-light exists, curing reaction occurs, and carries out moisture curing reaction simultaneously, in without UV-light situation, moisture curing crosslinking reaction can occur.There is fast setting, increase work efficiency, make shade or the partly solidified UV/ completely of bottom moisture dual cure function by moisture-curable.And because the special construction of polymkeric substance, to substrate bonding excellence.Thereby realize filling and provide protection to various complicated type wiring boards.
Embodiment
Below principle of the present invention and feature are described, example, only for explaining the present invention, is not intended to limit scope of the present invention.
Embodiment 1
1. the preparation of polymkeric substance
In a 20L reactor of being furnished with oil bath heating unit, prolong, dropping funnel, mechanical stirring, nitrogen inlet pipe, carry out drying treatment and replace protection with nitrogen.Under nitrogen protection; in reactor, add 236g KH-560 and 248g KH-570; 6g stannous octoate; temperature of reaction kettle is elevated to 60 DEG C; stirring and dripping hydroxy radical content in downhill reaction still is 0.11%; viscosity is the end hydroxyl silicone oil 10kg of 1670mPa.s, and decompression (0.098MPa) simultaneously removes the methyl alcohol of generation.Drip and completed in 6 hours.After dropwising, temperature of reaction is risen to 80 DEG C, and continue Depressor response after 2 hours, the colourless transparent liquid that obtains viscosity and be 3000～4000mPa.s is polymkeric substance shown in structural formula (1).The preparation of 2.UV/ moisture dual cure organosilicon glue
Take structural formula (1) polymkeric substance 97g (m=100), add 1-hydroxyl-phenylcyclohexyl ketone 3g, mix.
Embodiment 2
1. the preparation of polymkeric substance
Preparation method's reference example 1 of polymkeric substance (1).
The preparation of 2.UV/ moisture dual cure organosilicon glue
Take structural formula (1) polymkeric substance 98g (m=300), add 1-hydroxyl-phenylcyclohexyl ketone 1g, 2,4,6-trimethylbenzoyl-oxyethyl group-phenyl phosphine oxide 1g, mixes.
Embodiment 3
1. the preparation of polymkeric substance
Preparation method's reference example 1 of polymkeric substance (1).
The preparation of 2.UV/ moisture dual cure organosilicon glue
Take structural formula (1) polymkeric substance 98g (m=500), add 2-hydroxy-2-methyl-phenyl-acetone-11g, 2,4,6-trimethylbenzoyl-diphenyl phosphine oxide 1g, mixes.
Comparative example 1
Take structural formula (3) polymkeric substance 97g (m=100), add 1-hydroxyl-phenylcyclohexyl ketone 3g, mix.
Comparative example 2
Take structural formula (3) polymkeric substance 98g (m=300), add 1-hydroxyl-phenylcyclohexyl ketone 1g, 2,4,6-trimethylbenzoyl-oxyethyl group-phenyl phosphine oxide 1g, mixes.
Comparative example 3
Take structural formula (3) polymkeric substance 98g (m=500), add 2-hydroxy-2-methyl-phenyl-acetone-11g, 2,4,6-trimethylbenzoyl-diphenyl phosphine oxide 1g, mixes.
Embodiment and comparative example detect
1. detection method
Test one: embodiment 1,2,3 and comparative example 1,2,3 are applied to respectively to surface to be had on the identical wiring board of components and parts, solidifies energy 9000mJ/cm
2.
Test two: embodiment 1,2,3 and comparative example 1,2,3 are put respectively to glue on the wiring board without electronic devices and components, LED support 5050 is carried out bonding.Solidify energy 9000mJ/cm
2.
2. detected result and analysis
The detected result 1-2 that sees the following form.
Table 1 detected result
Table 2 test result
| Time/thrust | Embodiment 1 | Embodiment 2 | Embodiment 3 | Comparative example 1 | Comparative example 2 | Comparative example 3 |
| 0h | 3.1N | 3.2N | 3.2N | 3.3N | 3.2N | 3.2N |
| 24h | 7.3N | 7.5N | 7.6N | 3.5N | 3.3N | 3.5N |
| 168h | 18N | 19.1N | 18.7N | 3.8N | 3.8N | 3.9N |
Can find out by table 1, the two solidified glues of UV/ moisture that use the polymkeric substance of structural formula (1) to make, in the situation that there is no UV-light, can moisture curing, form the protection to wiring board, contrast is used and contains the structural formula (3) that two keys are merely able to ultraviolet light polymerization, through the dash area of UV-irradiation, wiring board not can not form to protective layer; Tested and can be found out by the thrust of table two, As time goes on, adhesive linkage loses the part of light because of moisture curing, and intensity progressively strengthens, and does not have comparative example's intensity of moisture curing that subtle change just occurs.
The foregoing is only preferred embodiment of the present invention, in order to limit the present invention, within the spirit and principles in the present invention not all, any amendment of doing, be equal to replacement, improvement etc., within all should being included in protection scope of the present invention.
Claims (9)
1. a UV/ moisture dual cure polymkeric substance, its structural formula is as shown in general formula (1):
Wherein, the span of m is 100-500.
2. polymkeric substance claimed in claim 1 is prepared the purposes of UV/ moisture dual cure organosilicon glue.
3. a UV/ moisture dual cure organosilicon glue, its raw material composition and each composition weight umber are as follows:
97～98 parts, polymkeric substance;
2～3 parts of light triggers;
The structural formula of described polymkeric substance is as shown in the general formula in claim 1 (1), and the span of m is 100-500.
4. as according to UV/ moisture dual cure organosilicon glue claimed in claim 3; it is characterized in that; described light trigger is selected from 1-hydroxyl-phenylcyclohexyl ketone, 2-hydroxy-2-methyl-phenyl-acetone-1,2; 4; 6-trimethylbenzoyl-oxyethyl group-phenyl phosphine oxide and 2; one or more mixing in 4,6-trimethylbenzoyl-diphenyl phosphine oxide.
5. UV/ moisture dual cure organosilicon glue as claimed in claim 3, it is characterized in that, the synthetic method of described polymkeric substance is: under nitrogen protection, in reactor, add 236g KH-560 and 248g KH-570,6g stannous octoate, is elevated to 60 DEG C by temperature of reaction kettle, and stirring and dripping hydroxy radical content in downhill reaction still is 0.11%, viscosity is the end hydroxyl silicone oil 10kg of 1670mPa.s, and decompression simultaneously removes the methyl alcohol of generation; Drip and completed in 6 hours, after dropwising, temperature of reaction is risen to 80 DEG C, and continue Depressor response after 2 hours, obtain the colourless transparent liquid that viscosity is 3000-4000mPa.s.
6. UV/ moisture dual cure organosilicon glue as claimed in claim 5, is characterized in that, the structural formula of described end hydroxyl silicone oil is as shown in general formula (2):
Wherein, the scope of n is 100-500.
7. the using method of UV/ moisture dual cure organosilicon glue described in the arbitrary claim of claim 3-6, obtain UV/ moisture dual cure organosilicon glue and for bonding or filling for the raw material composition according to described organosilicon glue mixes described polymkeric substance with described light trigger, and organosilicon glue is carried out to ultra-violet curing.
8. using method as claimed in claim 7, is characterized in that, the curing energy of described ultra-violet curing is 8000～9000mJ/cm
2.
9. the application in the filling of the online road of UV/ moisture dual cure organosilicon glue plate and protection described in the arbitrary claim of claim 3-6.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410414947.7A CN104193996B (en) | 2014-08-21 | The double cured silicone glue of a kind of UV/ dampness | |
| KR1020177007521A KR101824581B1 (en) | 2014-08-21 | 2014-10-22 | Uv/moisture dual curable organic silicon glue |
| PCT/CN2014/089145 WO2016026205A1 (en) | 2014-08-21 | 2014-10-22 | Uv/moisture dual curable organic silicon glue |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410414947.7A CN104193996B (en) | 2014-08-21 | The double cured silicone glue of a kind of UV/ dampness |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104193996A true CN104193996A (en) | 2014-12-10 |
| CN104193996B CN104193996B (en) | 2017-01-04 |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017825A (en) * | 2015-06-30 | 2015-11-04 | 中国乐凯集团有限公司 | Resin composition and application thereof |
| CN105367799A (en) * | 2015-12-18 | 2016-03-02 | 北京天山新材料技术有限公司 | Modified polysiloxane room temperature vulcanized silicone rubber |
| CN106497509A (en) * | 2016-11-04 | 2017-03-15 | 烟台德邦先进硅材料有限公司 | A kind of high impact-resistant type organosilicon bonded adhesives |
| CN105399955B (en) * | 2015-12-18 | 2019-01-25 | 江西蓝星星火有机硅有限公司 | A kind of graft reaction type silane adhesion promoters |
| CN109929079A (en) * | 2019-02-27 | 2019-06-25 | 惠州市德佑威新材料有限公司 | A kind of UV/ moisture dual cure resin and preparation method thereof |
| CN111234234A (en) * | 2018-11-28 | 2020-06-05 | 万华化学集团股份有限公司 | UV/moisture dual-curing polysiloxane and preparation method and application thereof |
| CN111303776A (en) * | 2020-03-09 | 2020-06-19 | 杭州电子科技大学 | Light-moisture curing composition and preparation method thereof |
| CN114316895A (en) * | 2021-12-31 | 2022-04-12 | 苏州润邦半导体材料科技有限公司 | LOCA glue with high transmittance and low shrinkage |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017825A (en) * | 2015-06-30 | 2015-11-04 | 中国乐凯集团有限公司 | Resin composition and application thereof |
| CN105017825B (en) * | 2015-06-30 | 2017-06-13 | 中国乐凯集团有限公司 | A kind of resin combination and its application |
| CN105367799A (en) * | 2015-12-18 | 2016-03-02 | 北京天山新材料技术有限公司 | Modified polysiloxane room temperature vulcanized silicone rubber |
| CN105399955B (en) * | 2015-12-18 | 2019-01-25 | 江西蓝星星火有机硅有限公司 | A kind of graft reaction type silane adhesion promoters |
| CN106497509A (en) * | 2016-11-04 | 2017-03-15 | 烟台德邦先进硅材料有限公司 | A kind of high impact-resistant type organosilicon bonded adhesives |
| CN106497509B (en) * | 2016-11-04 | 2019-07-09 | 烟台德邦科技有限公司 | A kind of high impact-resistant type organosilicon bonded adhesives |
| CN111234234A (en) * | 2018-11-28 | 2020-06-05 | 万华化学集团股份有限公司 | UV/moisture dual-curing polysiloxane and preparation method and application thereof |
| CN109929079A (en) * | 2019-02-27 | 2019-06-25 | 惠州市德佑威新材料有限公司 | A kind of UV/ moisture dual cure resin and preparation method thereof |
| CN111303776A (en) * | 2020-03-09 | 2020-06-19 | 杭州电子科技大学 | Light-moisture curing composition and preparation method thereof |
| CN114316895A (en) * | 2021-12-31 | 2022-04-12 | 苏州润邦半导体材料科技有限公司 | LOCA glue with high transmittance and low shrinkage |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101824581B1 (en) | 2018-02-01 |
| KR20170038076A (en) | 2017-04-05 |
| WO2016026205A1 (en) | 2016-02-25 |
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Effective date of registration: 20190415 Address after: 266000 Kaifeng Road 3-3 Renewable Resource Processing Demonstration Zone, Yantai Development Zone, Shandong Province Patentee after: Yantai Darbond Technology Co., Ltd. Address before: No. 98 Jinshajiang Road, Yantai Development Zone, Shandong Province, 264000 Patentee before: Yantai Debang Advanced Silicon Materials Co.,Ltd. |
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Granted publication date: 20170104 Termination date: 20200821 |