CN104610696A - Organic silicon composition for UV curing - Google Patents
Organic silicon composition for UV curing Download PDFInfo
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- CN104610696A CN104610696A CN201510003200.7A CN201510003200A CN104610696A CN 104610696 A CN104610696 A CN 104610696A CN 201510003200 A CN201510003200 A CN 201510003200A CN 104610696 A CN104610696 A CN 104610696A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
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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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- 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
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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- 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
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- 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
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- Inorganic Chemistry (AREA)
- Silicon Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The invention relates to an organic silicon composition for UV curing. The organic silicon composition comprises the following raw materials in parts by weight: 100 parts of polysiloxane with UV active functional groups at two ends, 10-30 parts of organic silicon resin with the UV active functional groups, 5-10 parts of an organic silicon oligomer with UV activity, and 0.1-10 parts of a free radical photoinitiator. The organic silicon composition provided by the invention is used for UV curing, is excellent in mechanical property, safe and environment-friendly, and has high transparency, high strength and low shrinkage.
Description
Technical field
The present invention relates to a kind of silicon composition for UV solidification, belong to chemical industry, electronic applications.
Background technology
The silicone resin material of UV solidification, compared with traditional organosilicon material, its curing mode is energy-conservation, and curing speed is fast.And solidify organic resin-phase ratio with common UV, then there are good temperature tolerance, weathering resistance, yellowing resistance.Therefore, UV cured silicone material can be used in from aspects such as shape coating (separant), optical fiber coatings, electronic package material, mould materials.
In general, photo-curable silicone system forms primarily of 3 kinds of components: the polysiloxane (organosilicon preformed polymer) of photosensitivity, light trigger and reactive thinner.In addition according to concrete purposes, also other filler or auxiliary agent can be added.
Wherein, reactive thinner refers to the micromolecular reactive monomer with acryloxy.Traditional non-organic silicon class monomer, comprises simple function, difunctionality, trifunctional and four functional monomers, and along with the raising of active group quantity, the curing activity of monomer improves gradually, solidifies the material hardness obtained and also increases gradually.Monofunctional monomer, as isobornyl acrylate (IBOA), Hydroxyethyl acrylate, isobutyl acrylate, common to there is volatility high, the shortcoming that smell is dense.Bifunctional monomer, as tri (propylene glycol) diacrylate (TPGDA), 1,6 hexanediol diacrylate (HDDA) etc., pungency is less, and solvency power is strong, active high, large to the bonding force of base material.And the viscosity of trifunctional monomer is general very large, active high, but there is larger pungency to human body.The monomer of higher functional degree also has commercial prod, and its range of application is then less.
Above-mentioned monomer and the silicone resin system poor compatibility of solidifying with UV, namely some monomers become muddy after mixing with organosilicon composition.Some monomers, although transparent after mixing with organosilicon composition, bleach immediately after solidification, cannot use as optically transparent material.
In addition, the volatility of above-mentioned monomer is high, and bio-toxicity is large.Be difficult to meet and be applied to the requirement to electric property and thermotolerance, yellowing resistance in Electronic Packaging field.
Another shortcoming of the UV cured adhesive formula of traditional non-organic silicon system is, owing to having a large amount of double bonds in system, in the radical polymerization process that UV is light-initiated, variable density causes larger contraction, and shrinking percentage is about 2%.
In addition, because the oxygen-permeable of organosilicon itself is higher, for the organosilicon systems of UV solidification, comparing common UV cured resin system, to be subject to the effect of oxygen inhibition more obvious.Therefore, organosilyl UV curing system is generally carry out in nitrogen atmosphere, and the solidification energy needed is higher.
Summary of the invention
Technical problem to be solved by this invention is, the shortcomings such as, smell large for existing UV cured adhesive shrinking percentage weighs, toxicity is high, easy to crack, a kind of silicon composition for UV solidification is provided, the mechanical property of this composition is excellent, safety and environmental protection, has heigh clarity, high strength and low-shrinkage.
The technical scheme that the present invention solves the problems of the technologies described above is as follows: a kind of silicon composition for UV solidification, is characterized in that, be made up of the raw material of following weight part:
1) 100 parts of both-ends have the polysiloxane of UV active function groups;
2) 10-30 part has the silicone resin of UV active function groups;
3) 5-10 part has the organosilicon oligomer of UV activity;
4) 0.1-10 part free radical photo-initiation.
On the basis of technique scheme, the present invention can also do following improvement.
Further, the molecular weight that described both-end has the polysiloxane of UV active function groups is 1000-100000, and its general molecular formula is:
Wherein, R
1, R
2, R
3, R
4, R
5and R
6representative has the hydrocarbyl group of 1 ~ 10 C atom, R respectively
1, R
2, R
3, R
4, R
5and R
6the hydrocarbyl group of representative is identical or different,
A representative has the group of UV photocuring activity, has acryloxy or methacryloxy in this group, and the group that A represents comprises one or more in having structure:
R
7representative has the alkylene group of 1 ~ 10 C atom, or R
7representative has the sub-ether of oxygen atoms between carbon atom, R
7example comprise: alkylidene group, such as methylene radical, ethylidene, propylidene, 1-methyl ethylidene, tetramethylene, 1-methyl isophthalic acid, 3-propylidene, 2-methyl isophthalic acid, one or more in 3-propylidene, 1,1-dimethyl-ethylidene, pentylidene; Arylidene, as penylene; Sub-ether, as-CH
2-CH
2-CH
2-OCH
2-CH
2-CH
2-;
Further, described R
1, R
2, R
3, R
4, R
5and R
6representative has the alkyl of 1 ~ 10 C atom respectively, aryl, alkenyl, one or more in alkynyl, such as: methyl, ethyl, propyl group, 1-methylethyl, butyl, 1-methyl-propyl, 2-methyl-propyl, 1, 1-dimethyl ethyl, amyl group, 1-methyl butyl, 1-ethyl propyl, 2-methyl butyl, 3-methyl butyl, 1, 2-dimethyl propyl, 2, 2-dimethyl propyl, hexyl, heptyl, octyl group, nonyl, decyl, cyclopentyl, cyclohexyl, methylcyclohexyl, phenyl, naphthyl, tolyl, xylyl, benzyl, styroyl, vinyl, allyl group, propenyl, styryl, cinnamyl group, ethynyl, one or more in proyl,
Described R
7representative has the alkylene of 1 ~ 6 C atom, or between carbon atom, have the sub-ether of oxygen atoms.
Further, described R
1, R
2, R
3, R
4, R
5and R
6representative has one or more in the alkyl of 1 ~ 6 C atom, aryl, alkenyl, alkynyl respectively, such as: one or more in methyl, ethyl, propyl group, butyl, amyl group, octyl group, cyclopentyl, phenyl.
Described R
7representative has the alkylene of 1 ~ 4 C atom, or between carbon atom, have the sub-ether of oxygen atoms.
Further, the silicone resin described in UV active function groups has following general formula: [R
1r
2r
3siO
1/2]
a[SiO
2]
b[A-SiO
3/2]
c,
Wherein, R
1, R
2, R
3it is described above with the structure of A representative,
A, b and c represent the molar fraction in silicone resin shared by structural unit respectively, a+b+c=1, and 0<c<1.
Further, the organosilicon oligomer of the described UV of having activity refers to the small molecules polysiloxane of acryloxypropyl or the methacryloxypropyl be directly connected containing one or several and Siliciumatom, for participating in the light-initiated Raolical polymerizable of UV, viscosity is 1-500mPa.s, the structure of these small molecules polysiloxane and preparation method are see the disclosed specification sheets of Chinese patent 201310518918.0 " preparation method of a kind of organic silicon acrylic ester for UV cured resin and organosilicon methacrylate monomer ", and part-structure is as follows:
Further, described free radical photo-initiation is one or more in bitter almond oil camphor, benzoin derivatives, benzil base, benzil radical derivative, methyl phenyl ketone, acetophenone derivs, benzophenone, benzophenone derivates, thioxanthone, thioxanthone derivative.
Further, described free radical photo-initiation is benzophenone, 1-hydroxycyclohexylphenylketone (trade(brand)name Irgacure 184, Ciba Specialty Chemicals Inc.), 2, 2-dimethyl hydroxyl methyl phenyl ketone (trade(brand)name Darocure 1173, Ciba Specialty Chemicals Inc.), 2, 2 dimethyl-Alpha-hydroxy P-isopropyl acetophenone (trade(brand)name Darocure 1116, Merck & Co., Inc.), 1-hydroxycyclohexyl phenyl ketone, 2-methyl isophthalic acid-(4-methylthio group phenyl)-2-morpholinyl-1-acetone (trade(brand)name Irgacure 907, Beijing Yingli Technology Development Co., Ltd), 2-hydroxy-2-methyl-1 phenyl-1-acetone, isopropyl thioxanthone, benzoin ether (trade(brand)name VIcure 10, lark prestige Science and Technology Ltd.) in one or more.
The invention has the beneficial effects as follows:
An advantage of the invention is that the polarity of each component in formula system is close, no matter before curing or after solidification, all there will not be blushing, the UV Photocurable Silicone Material with high transparent can be obtained, be specially adapted to the application of optical field.
Second advantage of the present invention is by regulating the amount with the silicone resin of UV active function groups, obtaining the adjustable high intensity UV Photocurable Silicone Material of performance within the specific limits.
3rd advantage of the present invention is by regulating the amount with the organosilicon oligomer of UV activity, can obtaining that have different viscosity, that operability is different UV Photocurable Silicone Material.
4th advantage of the present invention is the characteristic utilizing silicone resin and linear body, can obtain having low-shrinkage, the UV Photocurable Silicone Material of good, the color inhibition of temperature tolerance.
Accompanying drawing explanation
Fig. 1 a is the infrared spectrum of end hydrogen polysiloxanes prepared by the embodiment of the present invention 1;
Fig. 1 b is the infrared spectrum of polysiloxane DA-1 prepared by the embodiment of the present invention 1;
Fig. 2 is the infrared spectrum of silicone resin MA-2 prepared by the embodiment of the present invention 2;
Fig. 3 is the infrared spectrum of organosilicon oligomer TM-3 prepared by the embodiment of the present invention 3;
Embodiment
Be described principle of the present invention and feature below, example, only for explaining the present invention, is not intended to limit scope of the present invention.
Embodiment 1 both-end has the synthesis of the polysiloxane DA-1 of UV active function groups
End hydrogen polysiloxanes (Si-H content the is 0.003%) 2000g that viscosity is 10Pa.s is added in 5-L there-necked flask, 1,6-hexanediyl ester 20g, normal heptane 500mL, content is the platinum-vinyl polysiloxane title complex 1g of 5000ppm, be equipped with mechanical stirring and thermometer, be placed in heating oil bath, be heated to 70 DEG C of stirring reactions 5 hours.Stop heating and stir, by reaction mixture underpressure distillation except desolventizing, obtaining the polysiloxane DA-1 that water white both-end has UV active function groups.
Fig. 1 a and 1b is the infrared spectrum of end hydrogen polysiloxanes and DA-1 respectively.Infrared spectrum (the cm of end hydrogen polysiloxanes
-1): 2963,2127,1413,1258,1014,910,864,788,701,659.Infrared spectrum (the cm of DA-1
-1): 2962,1729,1687,1408,1297,1258,1192,1013,864,790,702,661.In fig 1 a, 2127cm
-1there is the characteristic feature peak of Si-H group at place.And in Figure 1b, the peak of Si-H group disappears, and there is charateristic avsorption band that is acrylate-based and methylene radical, prove to there occurs above-mentioned addition reaction.
Embodiment 2 has the synthesis of the silicone resin MA-2 of UV active function groups
248.35g methyl allyl acyloxypropyl trimethoxysilane is added in 5-L there-necked flask, 1065.54g tetramethoxy-silicane, 162.38g hexamethyldisiloxane, 310g aqueous sulfuric acid (2wt%), 1500mL normal heptane, be equipped with mechanical stirring, thermometer, dean-stark pipe and prolong, receiving bottle, after mixture is at room temperature stirred 2 hours, fluid temperature is elevated to 40 DEG C, now oil bath Heating temperature is elevated to 70 DEG C, stirring reaction is after 2 hours, continue the methyl alcohol distilling and generate that heats up, until fluid temperature rises to 80 DEG C, stop stirring and heating, after question response mixture is down to room temperature, 7.09g potassium hydroxide is added in reaction product, 1500mL normal heptane and 30mL water, continue intensification oil bath temperature to 80 DEG C, and insulated and stirred 8 hours.Stop heating and stir, hold over night.By reaction mixture to be washed to neutrality, underpressure distillation is except desolventizing, and obtaining total mass is the colourless non-volatility liquid silicone that 750.43g (productive rate is 98.4%) is transparent, and viscosity is 20Pa.s, and specific refractory power is 1.4103, called after MA-2.
Infrared spectrum (Fig. 2) (cm of MA-2
-1): 2960,2927,2856,1732,1408,1252,1186,1051,863,838,755,690, its theoretical construct formula is as follows:
Embodiment 3 has the synthesis of the organosilicon oligomer TM-3 of UV activity
To one be furnished with constant pressure funnel, magnetic agitation, nitrogen protection 500mL there-necked flask in; add 117.16g (0.5mol) acryloxypropyl Trimethoxy silane; 0.15g trifluoromethanesulfonic acid; 0.15g BHT; be heated to 50 DEG C, in reaction flask, drip 198.35g (1.5mol) acetoxytrimethylsilane by constant pressure funnel.After being added dropwise to complete, stirring reaction 2 hours, is warmed up to 80 DEG C, is steamed by the methyl acetate of generation.After completion of the reaction, reaction product is transferred in separating funnel, add 150mL normal heptane, wash 6 times with each 100mL, obtain neutral solution.Decompression rotary evaporation obtains 189.27g acryloxypropyl three (trimethylsiloxy group) silane, called after TM-3, and productive rate is 92.6%.Infrared spectrum (cm
-1): 2945,2841,1725,1638,1487,1408,1296,1263,1187,1079,985,810,671,611.
Embodiment 4 UV cured silicone material prescription and cure test
In order to useful achievement of the present invention is described, carry out contrast experiment by formula, formula composition and the rear performance of solidification are in table 1.
The vinyl MQ resin used in table 1 is commercial organosilicon MQ solid resin, purchases and builds Orange S. A. from Shanghai, and its contents of ethylene is 2wt%.Fumed silica model is R974.According to the method for expressing of rubber and plastic formulation art, in table 1, the amount of each component is mass fraction (phr).
After fully mixing each component in the ratio in table 1, require to make sheet material, by mixture levelling in mould according to GB/T528-2009.UV photocuring is carried out under high voltage mercury lamp;
Require to make dumbbell shaped silica gel exemplar according to GB/T528-2009, use puller system test tensile strength;
Table 1
As can be seen from Table 1, in light trigger 1173 situation of use 1 mass parts, carry out UV photocuring to DA-1 merely, its tensile strength is very low, does not almost have practical use.Use vinyl MQ resin to carry out reinforcement, object improves its mechanical property, but the vinyl of vinyl MQ resin cannot be formed with it effectively crosslinked, therefore be seriously clamminess in the cured product surface obtained.And after adding fumed silica, the system transparency declines.Adopt silicone resin MA-2 to strengthen for system, can realize Possessing high optical transparent while, obtain the product that tensile strength is very high.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, within the spirit and principles in the present invention all, any amendment done, equivalent replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (6)
1., for a silicon composition for UV solidification, it is characterized in that, be made up of the raw material of following weight part:
1) 100 parts of both-ends have the polysiloxane of UV active function groups;
2) 10-30 part has the silicone resin of UV active function groups;
3) 5-10 part has the organosilicon oligomer of UV activity;
4) 0.1-10 part free radical photo-initiation.
2. silicon composition according to claim 1, is characterized in that, the molecular weight that described both-end has the polysiloxane of UV active function groups is 1000-100000, and its general molecular formula is:
Wherein, R
1, R
2, R
3, R
4, R
5and R
6representative has the hydrocarbyl group of 1 ~ 10 C atom, R respectively
1, R
2, R
3, R
4, R
5and R
6the hydrocarbyl group of representative is identical or different,
A representative has the group of UV photocuring activity, has acryloxy or methacryloxy in this group, and the group that A represents comprises one or more in having structure:
R
7representative has the alkylene group of 1 ~ 10 C atom, or R
7representative has the sub-ether of oxygen atoms between carbon atom.
3. silicon composition according to claim 2, is characterized in that, described R
1, R
2, R
3, R
4, R
5and R
6representative has one or more in the alkyl of 1 ~ 10 C atom, aryl, alkenyl, alkynyl respectively.
4., according to the arbitrary described silicon composition of claim 2-3, it is characterized in that, described in there is UV active function groups silicone resin there is following general formula: [R
1r
2r
3siO
1/2]
a[SiO
2]
b[A-SiO
3/2]
c,
Wherein, R
1, R
2and R
3representative structure as described in claim 2 or claim 3,
A representative group as claimed in claim 2,
A, b and c represent the molar fraction in silicone resin shared by structural unit respectively, a+b+c=1, and 0<c<1.
5. silicon composition according to claim 4, it is characterized in that, the organosilicon oligomer of the described UV of having activity refers to the small molecules polysiloxane of acryloxypropyl or the methacryloxypropyl be directly connected containing one or several and Siliciumatom, and viscosity is 1-500mPa.s.
6. silicon composition according to claim 5; it is characterized in that, described free radical photo-initiation is one or more in bitter almond oil camphor, benzoin derivatives, benzil base, benzil radical derivative, methyl phenyl ketone, acetophenone derivs, benzophenone, benzophenone derivates, thioxanthone, thioxanthone derivative.
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|---|---|---|---|
| CN201510003200.7A CN104610696B (en) | 2015-01-05 | 2015-01-05 | Organic silicon composition for UV curing |
| PCT/CN2015/071408 WO2016109992A1 (en) | 2015-01-05 | 2015-01-23 | Organic silicon composition for uv curing |
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|---|---|---|---|
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| Publication number | Publication date |
|---|---|
| WO2016109992A1 (en) | 2016-07-14 |
| CN104610696B (en) | 2017-05-24 |
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