CN1936172A - Environment-protection coating printing adhesive and its preparing method - Google Patents
Environment-protection coating printing adhesive and its preparing method Download PDFInfo
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- CN1936172A CN1936172A CN 200610096073 CN200610096073A CN1936172A CN 1936172 A CN1936172 A CN 1936172A CN 200610096073 CN200610096073 CN 200610096073 CN 200610096073 A CN200610096073 A CN 200610096073A CN 1936172 A CN1936172 A CN 1936172A
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Abstract
The invention relates to an environment protecting resin-bonded pigment printing adhesive that is made up according the following steps: adding 0.5-1% polyacrylic acid salt into polyurethane acrylic ester emulsion, adjusting pH value to 7-8 to gain cream, and the viscosity is 30-60Pa.S. The preparation of polyurethane acrylic ester emulsion includes the following steps: gaining end ethenyl polyurethane performed polymer from polyether glycol, isocyanic ester and auxiliary agent, mixing the preformed polymer with acrylic ester monomer and water to make dispersing liquid, irradiating for 30-50 minutes at 1.5-2.5KGy radiation dose. The content of formaldehyde is below 5ppm and APEO below 5ppm in the adhesive. The product is environment protection.
Description
Technical field
The present invention relates to a kind of adhesive and preparation method thereof, specifically a kind of environment-friendly coating printing adhesive and its preparation method.
Background technology
COAT PRINTING is exactly will not have compatibility and reactive pigment to anchor at printing method on the fabric to fabric with adhesive.Its technology is simple, bright in colour, has characteristics such as washable, rub resistance, fastness be strong.Most in the market pigment printing binding agents contain a certain amount of N-hydroxyacrylamide cross-linking monomer, bake with storage process in Diazolidinyl Urea, make on the fabric free content of formaldehyde can't reach the requirement of underwear and children's garment, products export is restricted.The pigment printing binding agent of high-quality, environment-friendly type or printing paste are mostly from external import, to satisfy domestic and international requirement to high-quality textiles and clothes at present.
In addition, by extensive studies and demonstration, some countries of Europe formulated regulation limitations production and have used APEO alkylphenol polyoxyethylene (APEO) from 1976 to the potential harm of environment.Now existing the clearly defining of limiting the quantity of of the APEO that import textiles kimonos is loaded onto: be no more than 30ppm.
Therefore, the environment-protection coating printing adhesive of preparing no APEO, no aldehyde is the common issue that this area faces.
Summary of the invention
The present invention aims to provide a kind of green, environment-protection coating printing adhesive, and technical problem to be solved is that radiation causes the main component polyurethane-acrylic ester emulsion that free-radical emulsion polymerization prepares this adhesive.
PH7～8, viscosity that the alleged environment-protection coating printing adhesive of the present invention is made up of the polyurethane-acrylic acid ester emulsion (PUA) and the thickener polyacrylate of radiation polymerization preparation are the paste of 30～60PaS, and its parts by weight are as follows:
100 parts of polyurethane-acrylic acid ester emulsions,
0.51 part of polyacrylate.
This adhesive physical and chemical parameter is as follows:
Solid content (%) 40%
TENSILE STRENGTH (MPa) 2.0-4.2MPa
Elongation at break (%) 900-1400%
Dry fastness (level) 3-4
Fastness to wet rubbing (level) 3
Fastness to brushing (level) 3
After testing, content of formaldehyde＜5ppm, APEO content＜5ppm belongs to the environmental type product.
The preparation method of this adhesive is exactly that polyurethane-acrylic acid ester emulsion by radiation polymerization preparation under agitation adds 0.5～1% thickener and transfers pH7～8 with ammoniacal liquor, promptly gets the pigment printing binding agent that viscosity is 30～60PaS.
Described thickener is a polyacrylate.Polyacrylate is selected from a kind of ropiness increasing agent of doing among PTF (vapour crust), DM-5265 (dolantin), NeopolPFL (reputation brightness), HIT (BASF), the FS-200A (fixed star).
Described polyurethane-acrylic acid ester emulsion (PUA) by the logical nitrogen deoxidation of end-vinyl polyurethane (PU) and acrylate monomer aqueous dispersions after under 1.5～2.5KGy dosage of radiation condition irradiation prepare after 30～50 minutes.
Described end-vinyl polyurethane (PU) is preparation like this with the acrylate monomer aqueous dispersions:
Get PU and mix adding 1～5% emulsifying agent peregal 0 in back with acrylate monomer, add 1～2% (percentage by weight again, in mixture, triethylamine down together), stirred 2～5 minutes, add the water of 2～4 times of amounts then in high-speed stirred (1400 rev/mins～2500 rev/mins) down, just obtain end-vinyl urethane acrylate monomer aqueous dispersions (abbreviation aqueous dispersions).The proportioning of PU and acrylate monomer (mass ratio) is 1: 9～4: 6.
If among the PU acetone is arranged, then vacuum just obtains aqueous dispersions after sloughing acetone.
Described acrylate monomer is selected from one or more mix monomers in methyl methacrylate (MMA), butyl acrylate (BA), ethyl acrylate (EA), acrylonitrile (AN), the acrylic acid (AA).
Described end-vinyl polyurethane (PU) is preparation like this:
By adding 40～50% (percentage by weights after the polyether polyol vacuum dehydration, in polyalcohol, down with) isocyanates under 85～90 ℃ of conditions, reacted 1.5～2.5 hours, the chain extender that adds 4～8% dihydroxypropionic acid, 2～10% function monomer and 3～6% then reacts under 70～80 ℃ of conditions and just obtained PU in 2.5～3.5 hours.In course of reaction,, can add acetone diluted and stir with convenient if viscosity is bigger.
Described polyether polyol is selected from a kind of polyether polyol in polypropylene oxide dihydroxylic alcohols, polyethylene glycol oxide dihydroxylic alcohols, polypropylene oxide-ethylene oxide polyalcohol, the PolyTHF ethers polyalcohol.
Described isocyanates is selected from toluene di-isocyanate(TDI), 1, a kind of isocyanates in 6-hexamethylene diisocyanate, cyclohexane diisocyanate, the isophorone diisocyanate.
Described function monomer is selected from one or more monomers in methacrylic acid-β-hydroxypropyl acrylate, methacrylic acid-beta-hydroxy ethyl ester, hydroxy-ethyl acrylate, the hydroxypropyl acrylate.
Described chain extender is selected from one or more chain extenders in ethylene glycol (EG), diglycol (DEG), the butanediol (BDO).
The present invention is by the hydrophilic polyurethane prepolymer (PU) of solution polymerization, and hydrophilic polyurethane prepolymer/acrylate monomer blend disperseed in water, utilize cobalt 60-γ radiation, carry out the original position free-radical emulsion polymerization of vinyl monomer, make the aqueous polyurethane-acrylate emulsion.In radical polymerization process, the PA strand of PU strand and growth interpenetrates, intersects and tangles, and grafting or the crosslinked compatibility that has further increased between PU, the PA, " cooperative effect " and " force and dissolve each other " effect by IPN be easy to make size evenly, the regular compound PUA emulsion of form, thereby improve performances such as water-fast, antifouling, saturating wet, fastness to washing of pigment printing binding agent and good hand feeling.
The specific embodiment
Below by embodiment the present invention is described in detail.
The used main raw material(s) of embodiment is as follows:
Polyether polyols is polypropylene oxide dihydroxylic alcohols, polyethylene glycol oxide dihydroxylic alcohols, polypropylene oxide-ethylene oxide polyalcohol, PolyTHF ethers polyalcohol, industrial goods, and Plant of Tianjin Petrochemical Company three factories produce;
Isocyanates is selected toluene di-isocyanate(TDI), 1 for use, 6-hexamethylene diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, industrial goods, and Bayer A.G produces;
Dihydromethyl propionic acid (DMPA), industrial goods, Sweden Perstorp produces;
Chain extender: ethylene glycol (EG), diglycol (DEG), butanediol (BDO), chemical pure, Beijing sharp fine chemicals of benefit company produces;
Acetone (AT), industrial goods; Triethylamine (TEA), chemical pure, Beijing sharp fine chemicals of benefit company produces;
Methyl methacrylate (MMA), butyl acrylate (BA), ethyl acrylate (EA), acrylonitrile (AN), acrylic acid (AA), more than all be industrial goods, Shanghai Gaoqiao petrochemical industry three factories produce; Methacrylic acid-β-hydroxypropyl acrylate, hydroxy-ethyl acrylate, hydroxypropyl acrylate, methacrylic acid-beta-hydroxy ethyl ester,, being industrial goods, the Dongfang Chemical Plant, Beijing, The East Chemical Plant,Beijing produces;
Emulsifying agent peregal 0: technical grade, auxiliary reagent factory, long river, Hangzhou produces; Thickener is the anionic polyacrylate, industrial goods, and Dandong Fixed Star Fine Chemical Co., Ltd provides; Deionized water, self-control.
The cobalt source (
60The Co gamma-ray radiation source), is about 20,000 Curie, Anhui ice wild goose spoke Co., Ltd.
Embodiment 1:
Concrete synthetic operation method is as follows:
(1), the preparation of end-vinyl urethane acrylate monomer aqueous dispersions
In stainless steel cauldron, drop into ethylene oxide di-alcohols polyether Glycols, at 100-120 ℃ of vacuum dehydration 2h; After be cooled to 80 ℃, add toluene di-isocyanate(TDI), at 85-90 ℃ of insulation reaction 2h; Be cooled to 75 ℃, add hydrophilic monomer dihydromethyl propionic acid, chain extender diglycol, methacrylic acid-β-hydroxypropyl acrylate, insulation reaction 3h.In course of reaction, if viscosity should add acetone when big.Mix (1: 9) with acrylate mixing monomer again, add emulsifying agent peregal 0, prepare hydrophilic polyurethane prepolymer/mixture of vinyl monomer, be cooled to below 30 ℃, add the neutralizer triethylamine, stirring reaction 2-5 minute, the aqueous dispersion that (1400 rev/mins-2500 rev/mins) add 2～4 times of amounts under high-speed stirred became aqueous emulsion, behind vacuum removal acetone, prepare end-vinyl urethane acrylate monomer aqueous dispersions.
The consumption of each composition is as follows in the above-mentioned technical process:
Polyethylene glycol oxide ether dihydroxylic alcohols 100g
Toluene di-isocyanate(TDI) 40-50g
Dihydromethyl propionic acid 4-8g
Diglycol 3-6g
Methacrylic acid-β-hydroxypropyl acrylate 2-10g
Acetone 30-60g
Triethylamine 2-4g
Peregal 0 1-5g
Water 2-4 doubly measures
(2), preparation aqueous polyurethane-acrylate (PUA) emulsion
End-vinyl urethane acrylate monomer aqueous dispersions placed in the irradiation capsule stir, irradiation capsule is placed in the irradiation field, logical nitrogen N
2, time 5min removes the oxygen in the pre-emulsion, rises the radiation of cobalt source and causes dosage of radiation 2.0KGy, the about 30min-50min of exposure time;
(3), the preparation of PUA pigment printing binding agent
Polyurethane-acrylic ester emulsion under agitation adds thickener, is 0.5-1% by weight addition, and reaches 7-8 with the ammoniacal liquor adjust pH; Emulsion after the thickening is a paste, and viscosity promptly gets water-and acrylate-polyurethane environmental protection type pigment printing binding agent at 30-60PaS.
Embodiment 2:
Concrete synthetic operation method is as follows:
(1), the preparation of end-vinyl urethane acrylate monomer aqueous dispersions
In stainless steel cauldron, drop into polypropylene oxide-ethylene oxide polyalcohol, at 100-120 ℃ of vacuum dehydration 2h; After be cooled to 80 ℃, add cyclohexane diisocyanate, at 85-90 ℃ of insulation reaction 2h; Be cooled to 75 ℃, add hydrophilic monomer dihydromethyl propionic acid, chain extender diglycol, hydroxypropyl acrylate, insulation reaction 3h.In course of reaction, if viscosity should add acetone when big.Mix (2: 8) with acrylate mixing monomer again and add emulsifying agent peregal 0, prepare hydrophilic polyurethane prepolymer/mixture of vinyl monomer, be cooled to below 30 ℃, add the neutralizer triethylamine, stirring reaction 2-5 minute, the aqueous dispersion that (1400 rev/mins-2500 rev/mins) add 2～4 times of amounts under high-speed stirred becomes aqueous emulsion, behind vacuum removal acetone, prepares end-vinyl urethane acrylate monomer aqueous dispersions.
The consumption of each composition is as follows in the above-mentioned technical process:
Polypropylene oxide-ethylene oxide polyalcohol 100g
Cyclohexane diisocyanate 40-50g
Dihydromethyl propionic acid 4-8g
Diglycol 3-6g
Hydroxypropyl acrylate 2-10g
Acetone 30-60g
Triethylamine 2-4g
Peregal 0 1-5g
Water 2-4 doubly measures
(2), preparation aqueous polyurethane-acrylate (PUA) emulsion
End-vinyl urethane acrylate monomer aqueous dispersions placed in the irradiation capsule stir, irradiation capsule is placed in the irradiation field, logical nitrogen N
2, time 5min removes the oxygen in the pre-emulsion, rises the radiation of cobalt source and causes dosage of radiation 2.0KGy, the about 30min-50min of exposure time;
(3), the preparation of PUA pigment printing binding agent
Polyurethane-acrylic ester emulsion under agitation adds thickener, is 0.5-1% by weight addition, and reaches 7-8 with the ammoniacal liquor adjust pH; Emulsion after the thickening is a paste, and viscosity promptly gets water-and acrylate-polyurethane environmental protection type pigment printing binding agent at 30-60PaS.
Embodiment 3:
Concrete synthetic operation method is as follows:
(1), the preparation of end-vinyl urethane acrylate monomer aqueous dispersions
In stainless steel cauldron, drop into the polypropylene oxide dihydroxylic alcohols, at 100-120 ℃ of vacuum dehydration 2h; After be cooled to 80 ℃, add isophorone diisocyanate, at 85-90 ℃ of insulation reaction 2h; Be cooled to 75 ℃, add hydrophilic monomer dihydromethyl propionic acid, chain extender butanediol, interior olefin(e) acid hydroxyl ethyl ester, insulation reaction 3h.In course of reaction, if viscosity should add acetone when big.Mix (3: 7) with acrylate mixing monomer again and add emulsifying agent peregal 0, prepare hydrophilic polyurethane prepolymer/mixture of vinyl monomer, be cooled to below 30 ℃, add the neutralizer triethylamine, stirring reaction 2-5 minute, the aqueous dispersion that (1400 rev/mins-2500 rev/mins) add 2～4 times of amounts under high-speed stirred becomes aqueous emulsion, behind vacuum removal acetone, prepares end-vinyl urethane acrylate monomer aqueous dispersions.
The consumption of each composition is as follows in the above-mentioned technical process:
Polypropylene oxide dihydroxylic alcohols 100g
Isophorone diisocyanate 40-50g
Dihydromethyl propionic acid 4-8g
Butanediol 3-6g
Hydroxy-ethyl acrylate 210g
Acetone 30-60g
Triethylamine 2-4g
Peregal 0 1-5g
Water 2-4 doubly measures
(2), preparation aqueous polyurethane-acrylate (PUA) emulsion
End-vinyl urethane acrylate monomer aqueous dispersions placed in the irradiation capsule stir, irradiation capsule is placed in the irradiation field, logical nitrogen N
2, time 5min removes the oxygen in the pre-emulsion, rises the radiation of cobalt source and causes dosage of radiation 2.0KGy, the about 30min-50min of exposure time;
(3), the preparation of PUA pigment printing binding agent
Polyurethane-acrylic ester emulsion under agitation adds thickener, is 0.5-1% by weight addition, and reaches 7-8 with the ammoniacal liquor adjust pH; Emulsion after the thickening is a paste, and viscosity promptly gets water-and acrylate-polyurethane environmental protection type pigment printing binding agent at 30-60PaS.
Embodiment 4:
Concrete synthetic operation method is as follows:
(1), the preparation of end-vinyl urethane acrylate monomer aqueous dispersions
In stainless steel cauldron, drop into PolyTHF ethers polyalcohol, at 100-120 ℃ of vacuum dehydration 2h; After be cooled to 80 ℃, add 1, the 6-hexamethylene diisocyanate is at 85-90 ℃ of insulation reaction 2h; Be cooled to 75 ℃, add hydrophilic monomer dihydromethyl propionic acid, chain extender ethylene glycol, methacrylic acid-beta-hydroxy ethyl ester, insulation reaction 3h.In course of reaction, if viscosity should add acetone when big.Mix (4: 6) with acrylate mixing monomer again and add emulsifying agent peregal 0, prepare hydrophilic polyurethane prepolymer/mixture of vinyl monomer, be cooled to below 30 ℃, add the neutralizer triethylamine, stirring reaction 2-5 minute, the aqueous dispersion that (1400 rev/mins-2500 rev/mins) add 2～4 times of amounts under high-speed stirred becomes aqueous emulsion, behind vacuum removal acetone, prepares end-vinyl urethane acrylate monomer aqueous dispersions.
The consumption of each composition is as follows in the above-mentioned technical process:
PolyTHF ethers polyalcohol 100g
1,6-hexamethylene diisocyanate 40-50g
Dihydromethyl propionic acid 4-8g
Ethylene glycol 3-6g
Methacrylic acid-beta-hydroxy ethyl ester 2-10g
Acetone 30-60g
Triethylamine 2-4g
Peregal 0 1-5g
Water 2-4 doubly measures
(2), preparation aqueous polyurethane-acrylate (PUA) emulsion
End-vinyl urethane acrylate monomer aqueous dispersions placed in the irradiation capsule stir, irradiation capsule is placed in the irradiation field, logical nitrogen N
2, time 5min removes the oxygen in the pre-emulsion, rises the radiation of cobalt source and causes dosage of radiation 2.0KGy, the about 30min-50min of exposure time;
(3), the preparation of PUA pigment printing binding agent
Polyurethane-acrylic ester emulsion under agitation adds thickener, is 0.5-1% by weight addition, and reaches 7-8 with the ammoniacal liquor adjust pH; Emulsion after the thickening is a paste, and viscosity promptly gets water-and acrylate-polyurethane environmental protection type pigment printing binding agent at 30-60PaS.
Claims (10)
1, a kind of environment-protection coating printing adhesive, it is characterized in that: pH7～8, the viscosity be made up of the polyurethane-acrylic acid ester emulsion and the polyacrylate of radiation polymerization preparation are the paste of 30～60 PaS, each composition weight umber is: 100 parts of polyurethane-acrylic acid ester emulsions, 0.5～1 part of polyacrylate.
2, by the preparation method of the described pigment printing binding agent of claim 1, it is characterized in that: transfer pH7～8 to obtain by the thickener polyacrylate that adds 0.5～1% (w/w) in polyurethane-acrylic acid ester emulsion and with ammoniacal liquor.
3, preparation method according to claim 2 is characterized in that: described polyurethane-acrylic acid ester emulsion be by after the logical nitrogen deoxidation of end-vinyl polyurethane and acrylate monomer aqueous dispersions under 1.5～2.5KGy dosage of radiation condition irradiation 30～50 minutes.
4, preparation method according to claim 3, it is characterized in that: described end-vinyl urethane acrylate monomer aqueous dispersions is to mix the back with acrylate monomer by end-vinyl polyurethane to add 1～5% (w/w) emulsifying agent peregal 0, the triethylamine that adds 1～2% (w/w) again, stirred 2～5 minutes, the water that adds 2～4 times of amounts then under high-speed stirred obtains.
5, according to claim 3 or 4 described preparation methods, it is characterized in that: described acrylate monomer is selected from one or more mix monomers in methyl methacrylate, butyl acrylate, ethyl acrylate, acrylonitrile, the acrylic acid.
6, according to claim 3 or 4 described preparation methods, it is characterized in that: described end-vinyl polyurethane is to be reacted 1.5～2.5 hours under 85～90 ℃ of conditions by the isocyanates that adds 40～50% (w/w) after the polyether polyol vacuum dehydration, and the dihydroxypropionic acid, 2～10% function monomer and 3～6% the chain extender that add 4～8% (w/w) then reacted 2.5～3.5 hours under 70～80 ℃ of conditions.
7, preparation method according to claim 6 is characterized in that: described polyether polyol is selected from a kind of polyether polyol in polypropylene oxide dihydroxylic alcohols, polyethylene glycol oxide dihydroxylic alcohols, polypropylene oxide-ethylene oxide polyalcohol, the PolyTHF ethers polyalcohol.
8, preparation method according to claim 6 is characterized in that: described isocyanates is selected from toluene di-isocyanate(TDI), 1, a kind of isocyanates in 6-hexamethylene diisocyanate, cyclohexane diisocyanate, the isophorone diisocyanate.
9, preparation method according to claim 6 is characterized in that: described function monomer is selected from one or more monomers in methacrylic acid-β-hydroxypropyl acrylate, methacrylic acid-beta-hydroxy ethyl ester, hydroxy-ethyl acrylate, the hydroxypropyl acrylate.
10, preparation method according to claim 6 is characterized in that: described chain extender is selected from one or more chain extenders in ethylene glycol, diglycol, the butanediol.
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| CNB2006100960730A CN100419152C (en) | 2006-09-13 | 2006-09-13 | Environment-protection coating printing adhesive and its preparing method |
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| DE3318147A1 (en) * | 1983-05-18 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | METHOD FOR THE PRODUCTION OF COMPOUNDS HAVING ISOCYANURATE GROUPS AND OLEFINIC DOUBLE BINDINGS, THE COMPOUNDS AVAILABLE ACCORDING TO THIS METHOD AND THEIR USE AS BINDERS OR. BINDING COMPONENT IN COATING AGENTS |
| DE19853569A1 (en) * | 1998-11-20 | 2000-05-25 | Bayer Ag | New urethane acrylates, processes for their preparation and their use |
| DE10346118A1 (en) * | 2003-10-04 | 2005-09-22 | Degussa Ag | Powder coating compositions of urethane (meth) acrylates and micronized waxes and their use |
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