CN105255411A - Preparation method of organic siloxane modified chlorinated polypropylene adhesive - Google Patents
Preparation method of organic siloxane modified chlorinated polypropylene adhesive Download PDFInfo
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- CN105255411A CN105255411A CN201510816273.8A CN201510816273A CN105255411A CN 105255411 A CN105255411 A CN 105255411A CN 201510816273 A CN201510816273 A CN 201510816273A CN 105255411 A CN105255411 A CN 105255411A
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Abstract
The invention relates to the field of high polymer materials and particularly relates to a preparation method of an organic siloxane modified chlorinated polypropylene adhesive. According to the preparation method, chlorinated polypropylene is modified by virtue of an organic siloxane modifying agent and acrylate monomers. The preparation method comprises the following specific steps: (a) preparing a grafting solution from the organic siloxane modifying agent and the acrylate monomers; (b) preparing a chlorinated polypropylene solution; and (c) reacting by virtue of the grafting solution and the chlorinated polypropylene solution, and separating and purifying reactants, so as to obtain the organic siloxane modified chlorinated polypropylene adhesive. The preparation method has the beneficial effects that the process is simple, the reaction is easily controlled, the cost is low, the grafting rate of chlorinated polypropylene is high, and both the adhering force and waterproof effect of the prepared organic siloxane modified chlorinated polypropylene adhesive are enhanced.
Description
Technical field
The present invention relates to polymeric material field, be specifically related to a kind of preparation method of organic siloxane modified chlorinated polypropylene adhesive.
Background technology
Along with the raising day by day of social development and human aesthetic, need to cover with paint, lacquer, colour wash, etc. polypropylene (PP) material surface, make it in outward appearance and performance, meet the demand of people further.Polypropylene surface tint permanence is poor, in order to improve paint adhesion, the methods such as corona treatment, flame treating, chemical treatment or coating polymer priming paint can be adopted to make substrate surface roughen, occur polar group, thus improve its surface energy, increase the sticking power of base material and coating.But conventional corona treatment, flame treating and chemical treatment can be subject to restriction in various degree, as high in environmental pollution, covering with paint and production cost, cover with paint, lacquer, colour wash, etc. time limitation etc.Therefore, applying polymer priming paint at substrate surface is the method preferably improving PP tint permanence, before PP application, first apply one deck caking agent, apply coating again, caking agent can improve the adhesive property between coating and PP, and this method simple and fast, not by the restriction of time, can optimize the coating process of PP simultaneously.
Chlorinated Polypropylene III (CPP) is polyacrylic a kind of chemical modification product, is widely used as the adhesion promoter between polypropylene and resin based coatings.Chlorinated Polypropylene III and polypropylene have identical main chain, and when CPP is applied over PP surface, macromolecular chain tangles mutually, thus has good sticking power.
On Chlorinated Polypropylene III molecular chain, introduce applicable grafted monomer by Graft Method, utilize polarity and the reactivity of polar group, the deficiency in Chlorinated Polypropylene III performance can be improved, improve bonding force.Common grafted monomer has anhydride group, oh group, carboxylic group or acrylic acid groups etc.But current modified product adopts single group to carry out modification mostly, cohesiveness and the water tolerance of modified product are poor, and a lot of technology (as Thermal-printing Technology etc.) modified chlorinated polypropylene sizing agent product of needing water tolerance stronger in the market, this type of single modified product can not meet the application requiring of association area.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of preparation method of modified chlorinated polypropylene adhesive, and the method percentage of grafting is high, and the tackiness agent cementability of preparation and water tolerance are all better.
A preparation method for organic siloxane modified chlorinated polypropylene adhesive, comprises the following steps:
A, preparation graft copolymer solution:
Take acrylic ester monomer 25 ~ 35 weight part, organo-siloxane coupling agent 1.5 ~ 3.0 weight part is dissolved in solvent, obtain graft copolymer solution;
B, preparation chlorinated polypropylene solution:
Take Chlorinated Polypropylene III 15 ~ 40 weight part, be dissolved in solvent, obtain chlorinated polypropylene solution;
C, prepare modified chlorinated polypropylene adhesive:
Take initiator 0.1 ~ 1.5 weight part, add in step b gained chlorinated polypropylene solution by wherein half together with the additive of 0.1 ~ 3.5 weight part, second half initiator adds in the graft copolymer solution of step a gained; Under an inert gas, the graft copolymer solution adding initiator is added to and adds in the chlorinated polypropylene solution of initiator, heat up and react, reacted rear cooling discharging, by products therefrom washing, drying, obtain modified chlorinated polypropylene adhesive;
Described solvent is at least one in toluene, dimethylbenzene or butylacetate, described initiator is the one in benzoyl peroxide, dicumyl peroxide or azo-bis-isobutyl cyanide, and described additive is the one in vinylbenzene, N,N-DIMETHYLACETAMIDE, dimethyl sulfoxide (DMSO) or acrylamide.
Wherein, the weightmeasurement ratio of acrylic ester monomer described in step a and solvent is 1 ﹕ 2 ~ 5, and the weightmeasurement ratio of described organo-siloxane coupling agent and solvent is 1 ﹕ 2 ~ 5; The weightmeasurement ratio of Chlorinated Polypropylene III described in step b and solvent is 1 ﹕ 2 ~ 5.
Wherein, acrylic ester monomer described in step a is 27.5 ~ 32 weight parts, and organo-siloxane coupling agent is 2.0 ~ 2.5 weight parts; Chlorinated Polypropylene III described in step b is 20 ~ 35 weight; Initiator described in step c is 0.25 ~ 1.4 weight part, and additive is 0.25 ~ 3 weight part.
Wherein, acrylic ester monomer described in step a and organo-siloxane coupling agent weight ratio are preferably 13 ~ 16 ﹕ 1.
Wherein, acrylic ester monomer described in step a is at least one in methyl methacrylate, vinylformic acid, vinyl acetate or butyl acrylate, is preferably butyl acrylate.
Wherein, the coupling agent of organo-siloxane described in step a is at least one in vinyltrimethoxy silane, vinyl three (b-methoxy ethoxy) silane or γ-methacryloxypropyl trimethoxy silane, is preferably γ-methacryloxypropyl trimethoxy silane.
Wherein, initiator described in step c is benzoyl peroxide, and its consumption is 2.5% of Chlorinated Polypropylene III, acrylic ester monomer and organo-siloxane coupling agent total mass.
Wherein, temperature of reaction described in step c is 80 ~ 115 DEG C, is preferably 85 ~ 100 DEG C; The described reaction times is 1 ~ 6h, is preferably 2.5 ~ 4h.
Wherein, at least one in methyl alcohol, butylacetate, acetone or methyl alcohol is adopted in step c.
Wherein, described Chlorinated Polypropylene III is the Chlorinated Polypropylene III of cl content 26 ~ 45%.
Embodiment
The invention provides that a kind of percentage of grafting is high, the preparation method of the modified chlorinated polypropylene adhesive of cementability and water-tolerant, comprise the following steps:
A, preparation graft copolymer solution:
Take acrylic ester monomer 25 ~ 35 weight part, organo-siloxane coupling agent 1.5 ~ 3.0 weight part is dissolved in solvent, obtain graft copolymer solution;
B, preparation chlorinated polypropylene solution:
Take Chlorinated Polypropylene III 15 ~ 40 weight part, be dissolved in solvent, obtain chlorinated polypropylene solution;
C, prepare modified chlorinated polypropylene adhesive:
Take initiator 0.1 ~ 1.5 weight part, add in step b gained chlorinated polypropylene solution by wherein half together with the additive of 0.1 ~ 3.5 weight part, second half initiator adds in the graft copolymer solution of step a gained; Under an inert gas, the graft copolymer solution adding initiator is added to and adds in the chlorinated polypropylene solution of initiator, heat up and react, reacted rear cooling discharging, by products therefrom washing, drying, obtain modified chlorinated polypropylene adhesive;
Described solvent is at least one in toluene, dimethylbenzene or butylacetate, described initiator is the one in benzoyl peroxide, dicumyl peroxide or azo-bis-isobutyl cyanide, and described additive is the one in vinylbenzene, N,N-DIMETHYLACETAMIDE, dimethyl sulfoxide (DMSO) or acrylamide.
Wherein, the weightmeasurement ratio of acrylic ester monomer described in step a and solvent is 1 ﹕ 2 ~ 5, and the weightmeasurement ratio of described organo-siloxane coupling agent and solvent is 1 ﹕ 2 ~ 5; The weightmeasurement ratio of Chlorinated Polypropylene III described in step b and solvent is 1 ﹕ 2 ~ 5.
Wherein, acrylic ester monomer described in step a is 27.5 ~ 32 weight parts, and organo-siloxane coupling agent is 2.0 ~ 2.5 weight parts; Chlorinated Polypropylene III described in step b is 20 ~ 35 weight; Initiator described in step c is 0.25 ~ 1.4 weight part, and additive is 0.25 ~ 3 weight part.
Wherein, acrylic ester monomer described in step a and organo-siloxane coupling agent weight ratio are preferably 13 ~ 16 ﹕ 1.
Wherein, acrylic ester monomer described in step a is at least one in methyl methacrylate, vinylformic acid, vinyl acetate or butyl acrylate, be preferably butyl acrylate, described organo-siloxane coupling agent is at least one in vinyltrimethoxy silane, vinyl three (b-methoxy ethoxy) silane or γ-methacryloxypropyl trimethoxy silane, is preferably γ-methacryloxypropyl trimethoxy silane.
Wherein, described Chlorinated Polypropylene III is the Chlorinated Polypropylene III of cl content 26 ~ 45%, is preferably the Chlorinated Polypropylene III of cl content 30%.When dissolving Chlorinated Polypropylene III in step b, in order to strengthen dissolving and reaction effect, rare gas element preferred nitrogen, opens condensation, warming while stirring under the provide protection of nitrogen, is warmed up to 60 ~ 80 DEG C of constant temperature again, Chlorinated Polypropylene III is dissolved completely.Initiator is meeting accelerate decomposition under aerobic and Elevated Temperature Conditions; silicone coupling agents can be hydrolyzed formation cross-linking products under water environment, and both are all unfavorable for the carrying out reacted, and namely start to pass into nitrogen in the present invention in step b; under step c is also in the protection of nitrogen, ensure that carrying out smoothly of reaction.Preferably, step a can be recycled and reused for after solvent condenses in step b.
Wherein, described in step c, initiator is preferably benzoyl peroxide, and its consumption is 2.5% of Chlorinated Polypropylene III, acrylic ester monomer and organo-siloxane coupling agent total mass.
Initiator BP can decompose for a long time under kick off temperature, causing and causes effect decline, needing subsequently through adding initiator to promote initiation effect.In step c of the present invention when preparing modified chlorinated polypropylene adhesive, initiator joins respectively in the chlorinated polypropylene solution of the graft copolymer solution of step a gained, step b gained and causes, and avoids the decomposition of initiator, decreases the consumption of initiator; Meanwhile, the mode by separately adding initiator also contributes to the raising of product graft rate; In addition, the use of additive further enhancing the effect of initiator, and reduce the consumption of initiator, in the present invention, preferred additive is acrylamide.
Wherein, temperature of reaction described in step c is 80 ~ 115 DEG C, is preferably 85 ~ 100 DEG C; The described reaction times is 1 ~ 6h, is preferably 2.5 ~ 4h.The reaction mainly carried out in step c is:
In formula: what A replaced is used acrylic ester monomer or organo-siloxane coupling agent class monomer.
Preferably, by obtained graft modification Chlorinated Polypropylene III product when washing in step c, slowly pour in methyl alcohol, after leaving standstill 8 ~ 24h, the clear liquid inclined above, then adds the butylacetate dissolution precipitation thing in a heated condition of 10 ~ 50ml, is then again slowly poured in methyl alcohol by the throw out that butylacetate dissolves, repeatedly repeat 3 ~ 6 times, finally the throw out acetone of gained and methyl alcohol mixed liquor (weight ratio 1:10 ~ 20) are carried out repetitive scrubbing 3 ~ 6 times; In step c, drying mode adopts and dries.
Beneficial effect of the present invention:
1, the present invention introduces organo-siloxane coupling agent on Chlorinated Polypropylene III side chain, by changing altogether of acrylic ester monomer and silicone coupling agents, obtained tackiness agent has stronger cohesive force and more excellent waterproof effect than single esters of acrylic acid modified chlorinated polypropylene adhesive, can be widely used in the bonding of the non-polar polymer such as polypropylene, polyethylene.
2, the present invention introduces the stronger vinylbenzene of polarity, N,N-DIMETHYLACETAMIDE, dimethyl sulfoxide (DMSO) or acrylamide and does additive, effectively promotes percentage of grafting, the raising of percentage of grafting, improves cohesive force and waterproof effect further.
3, raw material of the present invention is easy to get, preparation technology is simple, reaction is easy to control, and solvent can reuse, change initiator addition means also reduces initiator amount, reduce further cost.
Below by embodiment, the specific embodiment of the present invention is described further, but not therefore by protection scope of the present invention restriction in one embodiment.
Embodiment 1
The preparation of a, graft copolymer solution
By weight methyl methacrylate: vinyltrimethoxy silane=13 ﹕ 1 precise 27.5 parts by weight of methylmethacrylate, 2.5 parts by weight of ethylene base Trimethoxy silanes are in beaker, accurately measuring 100ml butylacetate pours in beaker, be stirred to methyl methacrylate and vinyltrimethoxy silane dissolves completely, obtained graft copolymer solution;
B, preparation chlorinated polypropylene solution:
By 20 weight part Chlorinated Polypropylene IIIs and 100ml butylacetate, join in the four-hole boiling flask with condensation and logical nitrogen device, stir and pass into nitrogen, under nitrogen protection condition, open condensation, heat up, temperature to 60 ~ 80 DEG C again constant temperature, stir 0.5 ~ 3 hour, Chlorinated Polypropylene III is all dissolved, obtained chlorinated polypropylene solution;
C, prepare modified chlorinated polypropylene adhesive:
Precise 0.25 weight part initiator B PO, joins half wherein in the grafting liquid configured in a step, grafting liquid is joined in constant voltage drop-burette for subsequent use.And then dissolve second half initiator weighed up with 10ml butylacetate, take 0.25 parts by weight propylene acid amides in addition, join in chlorinated polypropylene solution solvent in b step together, under nitrogen atmosphere, temperature is carried out initiation reaction to reflux temperature.Start the grafting liquid dripped in constant pressure funnel simultaneously, control to dropwise in 1 ~ 2 hour, after dropwising, isothermal reaction is after 2.5 hours again, stopped reaction, cooling discharging, the product obtained slowly is poured in methyl alcohol, after leaving standstill 8h, the clear liquid inclined above, then adds the butylacetate dissolution precipitation thing in a heated condition of 40ml, is then again slowly poured in methyl alcohol by the throw out that butylacetate dissolves, repeatedly repeat 3 times, finally the throw out acetone of gained and methyl alcohol are carried out repetitive scrubbing 3 times.
Embodiment 2 ~ 5, comparative example 6
Embodiment 2 ~ 5, comparative example 6 are except difference described in following table 1, and rest materials and reaction conditions are all identical with embodiment 1.
Table 1 reaction substrate, content (weight part) and condition
In embodiment 1 ~ 5 and comparative example 6, raw materials used Chlorinated Polypropylene III, methyl methacrylate, butyl acrylate, vinylformic acid, vinyltrimethoxy silane, vinyl three (b-methoxy ethoxy) silane and γ-methacryloxypropyl trimethoxy silane are technical pure, toluene, acetone, butylacetate, methyl alcohol, vinylbenzene, N,N-DIMETHYLACETAMIDE, dimethyl sulfoxide (DMSO), acrylamide, benzoyl peroxide, dicumyl peroxide and azo-bis-isobutyl cyanide are analytical pure, and above-mentioned each raw material all comes to commercial products.Wherein, Chlorinated Polypropylene III is the Chlorinated Polypropylene III of cl content 30%.
The modified chlorinated polypropylene adhesive of embodiment 1 ~ 5 and comparative example 6 gained is measured sticking power, water tolerance and percentage of grafting respectively.
Sticking power test adopts paint film lattice drawing method to carry out, and gets PP, PVC, PE sample board of clean surface flat smooth, and use Virahol (IPA) to clean plastic front board, wiping is dried stand-by.By gained tackiness agent and chloroform 1 ﹕ 10 wiring solution-forming by weight, get equivalent solution respectively and drop on sample board, at 80 DEG C, cure about 30 minutes, treat that solvent volatilizees completely, the panel completing coating is at room temperature left standstill 3 days, its effect is tested.With cross-cut tester coating done lattice battle array pattern cut and penetrate, carrying out its sticking power size of division statistics.
Water resistance test carries out according to national standard " GB/T1733-93 paint film water tolerance assay method ".For the PP plate after film, seal its edge with the paraffin of weight ratio 1 ﹕ 1 and rosin blend, to prevent edge from soaking, afterwards half below PP plate is placed in distilled water, observe film at set intervals whether to bubble variable color, write down soak time when situations such as film generation foaming variable colors.
The product performance measurement result that embodiment 1 ~ 5 and comparative example 6 obtain is as shown in table 2:
Table 2 modified chlorinated polypropylene adhesive performance measurement result
As described in Table 2, comparative example 6 adopts single butyl acrylate to carry out modification, cohesiveness and water tolerance poor, embodiment 1 ~ 5 utilizes acrylic ester monomer and organo-siloxane coupling agent to chlorinated polypropylene modified, prepared adhesive bonds and water tolerance are all better, further increase percentage of grafting simultaneously.
The method preparing modified chlorinated polypropylene adhesive provided by the invention improves the percentage of grafting of Chlorinated Polypropylene III, this method is simple to operate, raw material is easy to get, obtained tackiness agent has stronger cohesive force and preferably waterproof effect, can be widely used in the bonding of the non-polar polymer such as polypropylene, polyethylene.
Claims (10)
1. a preparation method for organic siloxane modified chlorinated polypropylene adhesive, comprises the steps:
A, preparation graft copolymer solution:
Take acrylic ester monomer 25 ~ 35 weight part, organo-siloxane coupling agent 1.5 ~ 3.0 weight part is dissolved in solvent, obtain graft copolymer solution;
B, preparation chlorinated polypropylene solution:
Take Chlorinated Polypropylene III 15 ~ 40 weight part, be dissolved in solvent, obtain chlorinated polypropylene solution;
C, prepare modified chlorinated polypropylene adhesive:
Take initiator 0.1 ~ 1.5 weight part, add in step b gained chlorinated polypropylene solution by wherein half together with the additive of 0.1 ~ 3.5 weight part, second half initiator adds in the graft copolymer solution of step a gained; Under an inert gas, the graft copolymer solution adding initiator is added to and adds in the chlorinated polypropylene solution of initiator, heat up and react, reacted rear cooling discharging, by products therefrom washing, drying, obtain modified chlorinated polypropylene adhesive;
Described solvent is at least one in toluene, dimethylbenzene or butylacetate, described initiator is the one in benzoyl peroxide, dicumyl peroxide or azo-bis-isobutyl cyanide, and described additive is the one in vinylbenzene, N,N-DIMETHYLACETAMIDE, dimethyl sulfoxide (DMSO) or acrylamide.
2. the preparation method of organic siloxane modified chlorinated polypropylene adhesive according to claim 1, it is characterized in that: the weightmeasurement ratio of acrylic ester monomer described in step a and solvent is 1 ﹕ 2 ~ 5, the weightmeasurement ratio of described organo-siloxane coupling agent and solvent is 1 ﹕ 2 ~ 5; The weightmeasurement ratio of Chlorinated Polypropylene III described in step b and solvent is 1 ﹕ 2 ~ 5.
3. the preparation method of organic siloxane modified chlorinated polypropylene adhesive according to claim 1, is characterized in that:
Acrylic ester monomer described in step a is 27.5 ~ 32 weight parts, and organo-siloxane coupling agent is 2.0 ~ 2.5 weight parts;
Chlorinated Polypropylene III described in step b is 20 ~ 35 weight;
Initiator described in step c is 0.25 ~ 1.4 weight part, and additive is 0.25 ~ 3 weight part.
4. the preparation method of organic siloxane modified chlorinated polypropylene adhesive according to claim 1, is characterized in that: acrylic ester monomer described in step a and organo-siloxane coupling agent weight ratio are 13 ~ 16 ﹕ 1.
5. the preparation method of organic siloxane modified chlorinated polypropylene adhesive according to claim 1, it is characterized in that: acrylic ester monomer described in step a is at least one in methyl methacrylate, vinylformic acid, vinyl acetate or butyl acrylate, described organo-siloxane coupling agent is at least one in vinyltrimethoxy silane, vinyl three (b-methoxy ethoxy) silane or γ-methacryloxypropyl trimethoxy silane.
6. the preparation method of organic siloxane modified chlorinated polypropylene adhesive according to claim 1, it is characterized in that: acrylic ester monomer described in step a is butyl acrylate, described silane coupling agent is γ-methacryloxypropyl trimethoxy silane.
7. the preparation method of organic siloxane modified chlorinated polypropylene adhesive according to claim 1, it is characterized in that: initiator described in step c is benzoyl peroxide, its consumption is 2.5% of Chlorinated Polypropylene III, acrylic ester monomer and organo-siloxane coupling agent total mass.
8. the preparation method of organic siloxane modified chlorinated polypropylene adhesive according to claims 1 to 7, is characterized in that: the temperature of reaction described in step c is 80 ~ 115 DEG C, and the reaction times is 1 ~ 6h.
9. the preparation method of organic siloxane modified chlorinated polypropylene adhesive according to claim 1, is characterized in that: in steps d, washing process adopts at least one in methyl alcohol, butylacetate, acetone or methyl alcohol.
10. the preparation method of the organic siloxane modified chlorinated polypropylene adhesive according to claim 1 ~ 7 or 9 any one, is characterized in that: described Chlorinated Polypropylene III is the Chlorinated Polypropylene III of cl content 26 ~ 45%.
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Cited By (5)
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| CN106075873A (en) * | 2016-08-19 | 2016-11-09 | 哈尔滨体育学院 | A kind of modified fibre strengthens the preparation method of skis |
| CN110423309A (en) * | 2019-07-17 | 2019-11-08 | 广州市荔威化工有限公司 | A kind of preparation method of the acrylate modified chlorinated polypropylene of environment-friendly type aqueous organosiloxane |
| CN112679667A (en) * | 2020-12-09 | 2021-04-20 | 沧州师范学院 | Flexible polymer needle containing siloxane group and preparation method and application thereof |
| CN113480954A (en) * | 2021-07-27 | 2021-10-08 | 中山市皇冠胶粘制品有限公司 | Graft-modified acrylate pressure-sensitive adhesive, double-sided adhesive tape, and preparation method and application thereof |
| CN113667419A (en) * | 2021-08-12 | 2021-11-19 | 烟台正海合泰科技股份有限公司 | Three-layer adhesive film and production method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106075873A (en) * | 2016-08-19 | 2016-11-09 | 哈尔滨体育学院 | A kind of modified fibre strengthens the preparation method of skis |
| CN110423309A (en) * | 2019-07-17 | 2019-11-08 | 广州市荔威化工有限公司 | A kind of preparation method of the acrylate modified chlorinated polypropylene of environment-friendly type aqueous organosiloxane |
| CN112679667A (en) * | 2020-12-09 | 2021-04-20 | 沧州师范学院 | Flexible polymer needle containing siloxane group and preparation method and application thereof |
| CN112679667B (en) * | 2020-12-09 | 2022-08-02 | 沧州师范学院 | Flexible polymer needle containing siloxane group and preparation method and application thereof |
| CN113480954A (en) * | 2021-07-27 | 2021-10-08 | 中山市皇冠胶粘制品有限公司 | Graft-modified acrylate pressure-sensitive adhesive, double-sided adhesive tape, and preparation method and application thereof |
| CN113667419A (en) * | 2021-08-12 | 2021-11-19 | 烟台正海合泰科技股份有限公司 | Three-layer adhesive film and production method thereof |
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