CN1394928A - Preparation method of UV-light solidified pressure-sensitive adhesive - Google Patents
Preparation method of UV-light solidified pressure-sensitive adhesive Download PDFInfo
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- CN1394928A CN1394928A CN 01120215 CN01120215A CN1394928A CN 1394928 A CN1394928 A CN 1394928A CN 01120215 CN01120215 CN 01120215 CN 01120215 A CN01120215 A CN 01120215A CN 1394928 A CN1394928 A CN 1394928A
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Abstract
The present invention relates to a method for implementing safe and stable industrial preparation of acrylic pressure-sensitive adhesive which has no need of heating and drying, can be quickly cross-linked and solidified under the irradiation of UV light at normal temp. and can be made up using general coating machine. Said invention does not adopt water of general organic solvent, and has no any harmful volatile component, so that it is an environment-protecting type pressure-sensitive adhesive.
Description
Technical field:
The present invention relates to a kind of preparation method of UV-light solidified pressure-sensitive adhesive, particularly a kind of preparation method of pressure-sensitive adhesive of esters of acrylic acid of ultraviolet light polymerization.
Background technology:
Acrylic Pressure Sensitive Adhesive has been widely used in packing and the label industry.Generally, emulsion or solution polymerization process are adopted in the preparation of this tackiness agent.All there is shortcoming in the manufacture method of both of these case, if adopt solution polymerization process, so, employed solvent must be removed, normally dry under a comparatively high temps, a large amount of solvents that volatilize can bring great environmental pollution, and have increased industrial manufacturing cost; Adopt method of emulsion polymerization in solidifying the exsiccant process, to remove moisture, this need expend a large amount of energy, simultaneously, owing to adopted emulsifying agent, remaining in emulsifying agent in the tackiness agent can greatly influence the water resistance of emulsion pressure-sensitive adhesive, and damage otherwise performance, and as the transparency, adhesion etc.
Therefore, seek a kind of environmental friendliness and again the pressure-sensitive adhesive production technology of superior performance be an important developing direction, and had some to adopt electron radiations or ultraviolet light polymerization to prepare the example of pressure sensitive adhesive.
For example, Brockman etc. propose multi-functional acrylate's monomer and common acrylate monomer are mixed in U.S. Pat P 3,661,618, at room temperature coat on the base material, use high-energy radiation solidification again.Because need to use valuable electron radiation protector in this invention, cost is quite high, is difficult to industrialization.
U.S. Pat P 4181.752 adopts the prepolymerized method of ultraviolet radiation, earlier prepolymerization is to certain viscosity under the condition of control with monomer, and transformation efficiency is about about 10%, is applied to the further crosslinking curing of base material again, can reach 95% monomer conversion, system and have good adhesion property.Similarly method is also at U.S. Pat P 5183833, and USP 4943461, mention in USP 4223067 grades.
Karim adopts paracril as the polymkeric substance that increases the system viscosity in UV-light solidified pressure-sensitive.Except that the monomer of general acrylate, also introduce the polymerizable allylic cpd contain N in the diluting monomer, the photosensitive pressure sensitive adhesive of gained also has the good performance of sticking for vinyl plastics except that being suitable for the cohering of general material.
Yet, although above-mentioned several method can obtain effect in very a spot of experimental phase, if be amplified to the industrial production one-level many difficulties that can't overcome are just arranged, such as light pre-polymerization monomer methods, need to see through the reactor of UV-light, the resistance that must get rid of oxygen is poly-, and requires controlled polymerization process at any time, and these are to be difficult to obtain to realize in industrialized production.When adopting electron beam curing, the excess energy that electron radiation produces is usually burnt substrates coated, influences the quality of product.
Summary of the invention:
The invention provides a kind of preparation method who can safety and stability realizes the UV-light solidified pressure-sensitive adhesive of industrialized esters of acrylic acid.This pressure sensitive adhesive can be realized normal temperature coating on general coating machine, it can carry out industrial mass production easily, and the pressure-sensitive adhesive after the coating need not heat drying, normal temperature down just can be under the ultraviolet lamp radiation quick crosslinking curing, save energy greatly.
Specifically, the present invention prepares performed polymer with the mixture of acrylate monomer is implemented thermopolymerization under the mass polymerization state method, add the free radical chain transfer agent simultaneously, because the backflow effect of a small amount of solvent, make the partially polymerized heat in this polymerization-filling process obtain to discharge, thereby avoided the generation of implode.Simultaneously the molecular weight and the consumption of available adjustment chain-transfer agent and solvent that distributes also thereof are controlled.The diluted monomer dilution of institute's performed polymer that obtains back adds photosensitizers and mixes, but just can obtain the normal temperature coating and quick-setting pressure-sensitive adhesive under ultraviolet lamp.Perhaps with performed polymer and specific function monomer reaction, obtain the performed polymer of functionalization, coating back direct ultraviolet photo-crosslinking solidifies at normal temperatures, by the molecular weight of control prepolymer and the consumption of function monomer, can obtain the pressure-sensitive adhesive of various performances.
The preparation method of a kind of UV-light solidified pressure-sensitive adhesive of the present invention, in weight part, carry out according to the following steps successively: the preparation of (1) performed polymer is with soft monomer 40-90% (weight percent)
Hard monomer 5-45% (weight percent)
Function monomer 2-15% (weight percent)
Be mixed into 100 parts acrylate monomer blend; get wherein 30-50 part with after the benzoyl peroxide of 5-40 part solvent and 1-5 part mixes; join in the reactor; the free radical chain transfer agent stirring heating backflow of adding 0.1-1.5 part 5-20 minute; drip remaining acrylate monomer blend; after dripping off in 1-4 hour, back flow reaction 0.5-1.5 hour again, be performed polymer after the cooling.
Described soft monomer is the alkyl alcohol acrylate that contains 4-20 carbon atom, and they constitute the soft segment in the polymer chain, easily to being soaked into by maxxaedium.Commonly used has: n-butyl acrylate, Isooctyl acrylate monomer, octadecyl acrylate etc.
Described hard monomer is: methyl acrylate (MA), methyl methacrylate (MMA), vinyl-acetic ester (VAc), vinylbenzene (St), acrylonitrile (AN), Jia Jibingxisuanyizhi (EMA) or n-BMA (BMA) etc., their second-order transition temperature is higher, can be tackiness agent enough cohesive strengths are provided.
Described function monomer is: vinylformic acid, toxilic acid or maleic anhydride, (methyl) acrylamide, (methyl) propenoic acid beta-hydroxy ethyl ester or (methyl) propenoic acid beta-hydroxy propyl ester, (methyl) acrylic acid epoxy propyl ester, N hydroxymethyl acrylamide, methylene-succinic acid, multicondensed ethylene glycol double methyl methacrylate, Vinylstyrene etc.The introducing of function monomer can make the stripping strength of tackiness agent and hold viscosity and can be improved.Introduce polar group and can strengthen the sticking power of tackiness agent for polar surfaces, that introduces that crosslinked group then can obviously improve tackiness agent holds the viscosity energy.
Described free radical chain transfer agent is mainly used to the molecular weight and the distribution of controlling polymers, and then control performed polymer mass polymerization viscosity, mainly contains: n-dodecyl mercaptan, uncle's lauryl mercaptan or the like.
Described solvent is that strong free radical chain transferance tetracol phenixin, dimethylbenzene, ethanol, anhydrous methanol, Virahol or its mixture are arranged.
The present invention holds the viscosity energy for what improve polymkeric substance, glytidyl methacrylate copolymerization copolymerization is incorporated into performed polymer after, carry out acrylated.React as follows:
After being with active pair of key on the macromolecular chain of performed polymer, can be effectively caused by light trigger crosslinked, thereby improve the cohesive strength and the curing speed of tackiness agent greatly, obtain ideal and hold sticking intensity.
Concrete scheme is as follows: can further add 0.1-1 part four hexyl amine bromides in performed polymer more than 100 parts and make catalyzer, be heated to 110-115 ℃ of vinylformic acid that slowly splashes into 1-15 part, drip off the back and continue reaction 0.5-2 hour, can obtain acrylated performed polymer.(2) preparation of pressure sensitive adhesive
Acrylate with 5-100 part is done monomer diluent, adds light trigger and light-initiated auxiliary agent and mixes, and the light trigger consumption is generally 1-5 part, and light-initiated auxiliary dosage is generally 1-5 part.Add 100 parts of performed polymers again, the system viscosity of making maintains the 1000-5000 centipoise.Evenly be applied on the matrix,, place and press radiation curing under the ultra-violet lamp as polyester (PET) film.
In order to improve photopolymerization or crosslinked efficient, select suitable light trigger particularly important.Generally the UV-light light trigger of energy initiating polymerization of vinyl monomer can be used.Ultraviolet initiator commonly used is divided into two kinds: a kind of is free radical type; Another kind is cationic.Wherein the light trigger purposes of free radical type is the most extensive, and commonly used have st-yrax class ether as benzoin methyl ether, Benzoin ethyl ether, st-yrax n-butyl ether etc.; Benzene hexanone class is as benzophenone, D-1173 (Ciba) etc.In order to overcome the surperficial inhibition of oxygen, also to add organic amine as light-initiated auxiliary agent, as triethylamine, diethylamine, diethanolamine, trolamine or the like all are good selections.
The 750W medium pressure mercury lamp that the ultra-violet curing light source can adopt the Beijing Electrooptic Source Inst to produce.Effectively optical radiation centre wavelength is at 365 nanometers, radiation power 4.5mw/cm
2
Testing method is as follows: the mensuration of (1) 180 ° of stripping strength
With wide be that 25 centimetres Pressuresensitive Tape evenly is affixed on the stainless steel plate under certain pressure, after under temperature is 23 ± 2 ℃, placing half an hour, on electronic tensile machine, survey its 180 ° of stripping strengths, the peeling rate of electron detachment intensity machine is 0.5cm/s, and triplicate is averaged and is 180 ° of intensity of sample.(2) hold the mensuration of gluing intensity
With width is that 25 centimetres tested Pressuresensitive Tape carefully sticks on (one is brassboard, and one is attached plate) on the immediate two boards.Pasting length on the test board is 25 centimetres, and the stickup length on the attached plate is 50-60 centimetre.
After the coupons of above-mentioned preparation at room temperature put half an hour, it is hung vertically in constant temperature on the testing jig under the probe temperature again, hangs the weight of a heavy 1000g in the tag lower end, the record suspension time is holds sticking intensity.
Pressure sensitive adhesive of the present invention is rapid polymerization crosslinking under the radiation of UV-light, does not adopt water or common organic solvent, does not have any harmful volatile component, and need not special dry solidification and handle, be a kind of pressure-sensitive adhesive to the environment friendliness.
Embodiment:
Embodiment 1-9:
With 36.5 gram Isooctyl acrylate monomers; 53 gram butyl acrylates and 4 gram glytidyl methacrylate are mixed; get mixture 1/3 with a certain amount of dehydrated alcohol (consumption sees the following form) and 1.5 the gram benzoyl peroxides mix; add and be equipped with in the there-necked flask of reflux exchanger; add a certain amount of n-dodecyl mercaptan (consumption sees the following form); heat temperature raising to 82 ℃; refluxed 15 minutes; 2/3 monomer of measuring with remainder slowly splashed in the reaction flask with three hours again; keep the half an hour of refluxing after monomer drips off again, cooling discharging is performed polymer [1].
Gained performed polymer [1] is mixed with the triethylene Glycol diacrylate (TE) of 2 grams and the butyl acrylate (BA) of 10 grams, add the light trigger D-1173 of 3 grams and the trolamine of 3 grams, mixing makes the system viscosity maintain 2500 centipoises, be applied on the PET film evenly, place under the 750W ultraviolet lamp 15 centimeters to solidify 2 minutes.
The viscosity of the molecular weight control embodiment dodecyl sulphur anhydrous hexanol consumption system of tackiness agent is held viscous force
Alcohol consumption (%) is (cps) (min) 1 0.5 10＞100,000 31.22 0.7 10 12,200 20.33 0.75 10 7,300 15.24 0.8 10 3,500 5.15 0.9 10 2,850 0.56 0.5 15 42,000 21.57 0.5 20 15,200 17.88 0.5 25 6,700 10.29 0.5 30 3,700 2.0 (%)
As can be seen from the table, along with the increase of n-dodecyl mercaptan consumption, the viscosity of system reduces, and the viscous force of holding of pressure sensitive adhesive obviously reduces.Anhydrous hexanol also has similar effects.
Embodiment 10-14:
With 36.5 gram Isooctyl acrylate monomers; 53 gram butyl acrylates and 4 gram glytidyl methacrylate are mixed; get mixture 1/3 and 10 the gram dehydrated alcohols and 1.5 the gram benzoyl peroxides mix; add and to be equipped with in the there-necked flask of reflux exchanger, add 0.2 gram n-dodecyl mercaptan, heat temperature raising to 82 ℃; refluxed 15 minutes; 2/3 monomer of measuring with remainder slowly splashed in the reaction flask with three hours again, kept the half an hour of refluxing after monomer drips off again, and cooling discharging is performed polymer [1].
Performed polymer [1] is heated to 115 ℃, adds the tetraethylammonium bromide of 0.3 gram, the 2.6-ditertbutylparacresol of 0.3 gram. slowly be added dropwise to vinylformic acid 10 grams, keep 110 ℃ of reactions of temperature of reaction 2 hours, obtain the performed polymer [2] of acrylated.
The diluting monomer mixture of TE and BA, TE: BA=2: 5 (parts by weight), ratio with different performed polymer and thinner, add the light trigger D-1173 of 3 grams and the trolamine of 3 grams again, mixing makes the system viscosity maintain 4000 centipoises, be applied on the PET film evenly, place under the 750W ultraviolet lamp 15 centimeters to solidify 1.5 minutes.Obtain the pressure sensitive adhesive of uV curable.
The diluting monomer consumption is to tackiness agent Effect on Performance embodiment performed polymer: 180 ° of stripping strengths of thinner are held viscous force
(N/25cm) (hour)10 1∶0.2 1.25 ＞4811 1∶0.25 1.54 ＞4812 1∶0.30 0.78 ＞4813 1∶0.35 0.76 ＞4814 1∶0.40 1.08 ＞48
As can be seen from the table, the consumption that changes diluting monomer is also not obvious to the performance impact of pressure sensitive adhesive, and holding of tackiness agent glued intensity all greater than 48 hours, and the stripping strength of tackiness agent changes also less.
Claims (8)
1. the preparation method of a UV-light solidified pressure-sensitive adhesive, in weight part, carry out successively according to the following steps:
(1) preparation of performed polymer
With soft monomer 40-90% (weight percent)
Hard monomer 5-45% (weight percent)
Function monomer 2-15% (weight percent)
Be mixed into 100 parts acrylate monomer blend, get wherein 30-50 part with after the benzoyl peroxide of 5-40 part solvent and 1-5 part mixes, join in the reactor, the free radical chain transfer agent stirring heating backflow of adding 0.1-1.5 part 5-20 minute, drip remaining acrylate monomer blend, after dripping off in 1-4 hour, back flow reaction 0.5-1.5 hour again, be performed polymer after the cooling;
(2) preparation of pressure sensitive adhesive
Acrylate with 5-100 part is done monomer diluent, adds light trigger and light-initiated auxiliary agent and mixes, and the light trigger consumption is generally 1-5 part, and light-initiated auxiliary dosage is generally 1-5 part; Add 100 parts of performed polymers again, the system viscosity of making maintains the 1000-5000 centipoise, evenly is applied on the matrix, places to press radiation curing under the ultra-violet lamp;
Described soft monomer is the alkyl alcohol acrylate that contains 4-20 carbon atom;
Described hard monomer is: methyl acrylate (MA), methyl methacrylate (MMA), vinyl-acetic ester (VAc), vinylbenzene (St), acrylonitrile (AN), Jia Jibingxisuanyizhi (EMA) or n-BMA (BMA);
Described function monomer is: vinylformic acid, toxilic acid or maleic anhydride, (methyl) acrylamide, (methyl) propenoic acid beta-hydroxy ethyl ester or (methyl) propenoic acid beta-hydroxy propyl ester, (methyl) acrylic acid epoxy propyl ester, N hydroxymethyl acrylamide, methylene-succinic acid, multicondensed ethylene glycol double methyl methacrylate, Vinylstyrene.
2. according to the preparation method of claim 1, it is characterized in that: described soft monomer is n-butyl acrylate, Isooctyl acrylate monomer, octadecyl acrylate.
3. according to the preparation method of claim 1, it is characterized in that: described free radical chain transfer agent is a n-dodecyl mercaptan, uncle's lauryl mercaptan.
4. according to the preparation method of claim 1, it is characterized in that: described solvent is tetracol phenixin, dimethylbenzene, ethanol, anhydrous methanol, Virahol or its mixture.
5. according to the preparation method of claim 1, it is characterized in that: the light trigger consumption is 1-5 part, and light-initiated auxiliary dosage is 1-5 part.
6. according to the preparation method of claim 1, it is characterized in that: described light trigger is benzoin methyl ether, Benzoin ethyl ether, st-yrax n-butyl ether, benzophenone, D-1173 (Ciba).
7. according to the preparation method of claim 1, it is characterized in that: described light-initiated auxiliary agent is triethylamine, diethylamine, diethanolamine, trolamine.
8. according to the preparation method of claim 1, it is characterized in that: further in performed polymer more than 100 parts, add 0.1-1 part four hexyl amine bromides and make catalyzer, be heated to 110-115 ℃ of vinylformic acid that slowly splashes into 1-15 part, drip off the back and continue reaction 0.5-2 hour, obtain acrylated performed polymer.
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| CN100432176C (en) * | 2003-10-31 | 2008-11-12 | 3M创新有限公司 | Method for preparing a pressure-sensitive adhesive |
| CN101220122B (en) * | 2008-01-30 | 2010-06-02 | 上海华明高技术（集团）有限公司 | Plastics toughening agent containing nano-calcium carbonate and polyalcohol, and method for producing the same |
| CN101857786A (en) * | 2010-05-26 | 2010-10-13 | 北京高盟新材料股份有限公司 | Pressure-sensitive adhesive and preparation method thereof |
| CN101864257A (en) * | 2010-05-26 | 2010-10-20 | 北京高盟新材料股份有限公司 | Adhesive for automobile adhesive film and preparation method thereof |
| CN101967211A (en) * | 2010-09-29 | 2011-02-09 | 北京化工大学 | Preparation method of low molecular weight polyacrylic ester acrylic ester for photo-curing |
| CN101205451B (en) * | 2007-11-30 | 2011-04-27 | 华南理工大学 | Ultraviolet-anaerobic dual curing adhesive |
| CN102134455A (en) * | 2010-01-22 | 2011-07-27 | 日东电工株式会社 | Pressure-sensitive adhesive sheet |
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| CN102898980A (en) * | 2012-09-25 | 2013-01-30 | 苏州汾湖电梯有限公司 | Ultraviolet (UV) curing acrylic ester adhesive |
| CN102898970A (en) * | 2012-11-02 | 2013-01-30 | 绍兴振德医用敷料有限公司 | Method for preparing ultraviolet light polymerization environment-friendly antibacterial acrylic ester medical pressure sensitive adhesive product |
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-
2001
- 2001-07-06 CN CN 01120215 patent/CN1394928A/en active Pending
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| CN100432176C (en) * | 2003-10-31 | 2008-11-12 | 3M创新有限公司 | Method for preparing a pressure-sensitive adhesive |
| CN101205451B (en) * | 2007-11-30 | 2011-04-27 | 华南理工大学 | Ultraviolet-anaerobic dual curing adhesive |
| CN101220122B (en) * | 2008-01-30 | 2010-06-02 | 上海华明高技术（集团）有限公司 | Plastics toughening agent containing nano-calcium carbonate and polyalcohol, and method for producing the same |
| CN101824280B (en) * | 2009-12-29 | 2012-07-04 | 广州宏昌胶粘带厂 | Preparation method of pressure-sensitive adhesive capable of being solidified by ultraviolet light and pressure-sensitive adhesive tape |
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| CN101857786A (en) * | 2010-05-26 | 2010-10-13 | 北京高盟新材料股份有限公司 | Pressure-sensitive adhesive and preparation method thereof |
| CN101967211A (en) * | 2010-09-29 | 2011-02-09 | 北京化工大学 | Preparation method of low molecular weight polyacrylic ester acrylic ester for photo-curing |
| CN102206297A (en) * | 2011-03-30 | 2011-10-05 | 北京神彩优维喷墨材料科技有限公司 | Low polymer for ultraviolet light cured coating and printing ink, and preparation method thereof |
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| CN105719562A (en) * | 2016-01-28 | 2016-06-29 | 安徽盛鼎电器科技有限公司 | Label material free of release paper and making technology of label material |
| CN106752992A (en) * | 2017-01-22 | 2017-05-31 | 江苏旭泽技术有限公司 | A kind of pressure sensitive adhesive, its preparation method, application method and application |
| CN106752992B (en) * | 2017-01-22 | 2020-10-27 | 浙江欣麟新材料技术有限公司 | Pressure-sensitive adhesive, preparation method, use method and application thereof |
| CN110396370A (en) * | 2019-08-07 | 2019-11-01 | 济南北方泰和新材料有限公司 | A kind of cured modified acrylate pressure-sensitive adhesive of UV-LED and preparation method thereof |
| CN110396370B (en) * | 2019-08-07 | 2021-06-04 | 济南北方泰和新材料有限公司 | UV-LED curing modified acrylate pressure-sensitive adhesive and preparation method thereof |
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