CN108341916B - Environment-friendly water-based tackifier and preparation method thereof - Google Patents
Environment-friendly water-based tackifier and preparation method thereof Download PDFInfo
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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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
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
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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
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
- C08F283/008—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00 on to unsaturated polymers
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy 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
- C09J11/08—Macromolecular additives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses a preparation method of an environment-friendly water-based tackifier, which comprises the following steps: step 1: adding isophorone diisocyanate and polypropylene glycol into a reactor to obtain a polyurethane prepolymer; step 2: dropwise adding dimethylolpropionic acid, trimethylolpropane and 1, 4-butanediol into the polyurethane prepolymer, and reacting for a period of time in the presence of a catalyst dibutyltin dilaurate; and step 3: adding hydroxypropyl methacrylate, and reacting for a period of time; and 4, step 4: adding a neutralizing agent to adjust the pH value of the system to obtain a PU aqueous dispersion with an unsaturated double bond at the tail end; and 5: adding emulsifier and deionized water to emulsify the system, and then dripping acrylic monomer dissolved with terpene resin and rosin ester or disproportionated rosin. The invention aims to provide an environment-friendly water-based tackifier and a preparation method thereof.
Description
Technical Field
The invention relates to the field of papermaking auxiliaries, in particular to an environment-friendly water-based tackifier and a preparation method thereof.
Background
The main functions of the tackifier in the adhesive are as follows: firstly, increasing the initial adhesion time; improving the wettability; plasticity is added, and the cracking time of the adhesive is prolonged; increasing the mixing capacity of the filler and the polymer and reducing the cost. Because most of the tackifying resin is solid or crystal and is difficult to be compatible with the high polymer emulsion, the tackifying resin is dissolved by adopting an organic solvent (such as toluene and the like) firstly, and then the organic solvent and the high polymer emulsion are subjected to cold mixing or hot mixing, so that the emulsion type adhesive prepared by the method is not only unstable in storage, but also contains a volatile organic solvent harmful to human bodies.
At present, most of environment-friendly tackifiers are acrylate modified tackifiers, which are added into acrylic monomers to participate in copolymerization reaction in an emulsifier aqueous solution by utilizing the characteristics of unsaturated double bonds in terpene resins and rosin esters or disproportionated rosin. Due to the fact that the emulsifier is added into the tackifying resin, the storage stability of the water-based tackifying resin product is insufficient, and the water resistance of the adhesive added with the water-based tackifying resin is reduced.
Disclosure of Invention
The invention aims to provide an environment-friendly water-based tackifier and a preparation method thereof; unsaturated double bonds are introduced into self-emulsifying waterborne polyurethane, then propylene monomers, terpene resins and rosin esters or disproportionated rosin are added, and the environment-friendly self-emulsifying waterborne tackifier is obtained through free radical polymerization.
The technical scheme of the invention is as follows: a preparation method of the environment-friendly water-based tackifier comprises the following steps:
step 1: adding isophorone diisocyanate and polypropylene glycol into a reactor, and reacting for a period of time at 78-82 ℃ in the presence of a catalyst dibutyltin dilaurate to obtain a polyurethane prepolymer;
step 2: dropwise adding dimethylolpropionic acid, trimethylolpropane and 1, 4-butanediol into the polyurethane prepolymer, and reacting for a period of time in the presence of a catalyst dibutyltin dilaurate;
and step 3: reducing the temperature of the system to 63-67 ℃, adding hydroxypropyl methacrylate, and reacting for a period of time;
and 4, step 4: adding a neutralizing agent to adjust the pH value of the system to obtain a PU aqueous dispersion with an unsaturated double bond at the tail end;
and 5: adding emulsifier and deionized water to emulsify the system, then dripping acrylic monomer dissolved with terpene resin and rosin ester or disproportionated rosin, swelling for a period of time, heating to 80-85 ℃, adding PH buffering agent and adding initiator, and keeping the temperature for a period of time to remove residual monomer.
In the preparation method of the environment-friendly water-based tackifier, the raw materials comprise the following components in parts by weight:
in the above method for preparing an environmentally friendly water-based viscosity increasing agent, the emulsifier in step 5 is SDS; the amount of SDS is 15-20 parts by weight.
In the preparation method of the environment-friendly water-based tackifier, the reaction time of the step 1 is 2 hours, the reaction time of the step 2 is 3 hours, the reaction time of the step 3 is 2 hours, and the swelling time of the step 5 is 2 hours.
In the above preparation method of the environment-friendly water-based tackifier, step 2 further comprises 1-2 parts by weight of sodium allyl sulfosuccinate alkyl ester.
Meanwhile, the invention also discloses the environment-friendly water-based tackifier prepared by the method.
The invention has the following beneficial effects:
firstly, synthesizing unsaturated double bond-containing aqueous Polyurethane (PU) aqueous dispersion by using isophorone diisocyanate (IPDI), polypropylene glycol (PPG), Trimethylolpropane (TMP), hydroxypropyl methacrylate (HPMA) and dimethylolpropionic acid (DMPA) as raw materials; taking PU as seed emulsion, adding Butyl Acrylate (BA), Methyl Methacrylate (MMA), terpene resin and rosin ester or disproportionated rosin, and obtaining the self-emulsifying water-based tackifying emulsion through free radical polymerization.
Furthermore, in the invention, sodium allyl sulfosuccinate alkyl ester is added into the monomer dropwise added in the step 2, which is a reactive emulsifier, and the sodium allyl sulfosuccinate alkyl ester and the subsequently added hydroxypropyl methacrylate, terpene resin and rosin ester or disproportionated rosin monomer can generate polymerization and moderate crosslinking reaction, thereby improving the stability of the system and keeping better stability under severe use environment.
Detailed Description
The technical solution of the present invention will be described in further detail with reference to the following embodiments, but the present invention is not limited thereto.
Specific example 1:
200g of IPDI and 800g of PPG are added into a 500mL four-neck flask provided with a stirrer, a reflux condenser tube and a thermometer, after the temperature of the system is raised to 80 ℃, 3-4 drops of catalyst DBTDL are dripped, and the reaction is carried out for 2h under the protection of N2, so as to obtain the polyurethane prepolymer containing the active group-NCO. Cooling to 50 ℃, dropwise adding 9g of BDO, 11g of DMPA and 2g of TMP, heating to 80 ℃, dropwise adding 3-4 drops of catalyst DBTDL, reacting for 3 hours until-NCO reaches a preset value. Cooling to 65 ℃, adding 26g of hydroxypropyl methacrylate HPMA, and preserving the temperature for 2 h; then the temperature is reduced to 30 ℃, and a certain amount of triethylamine TEA is added for neutralization for 15 min. Adding deionized water, and emulsifying and dispersing the system at a high speed to obtain the PU aqueous dispersion with the end containing unsaturated double bonds.
Adding a small amount of emulsifier SDS and deionized water into the seed emulsion PU for pre-emulsification for 30min, slowly dropwise adding an acrylic monomer dissolved with 1200g of terpene resin and rosin ester, wherein the weight of the acrylic monomer is 900g, and the weight ratio of the terpene resin to the rosin ester is 1: 1; after swelling for 2h, heating to 82 ℃, adding a pH buffering agent NaHCO3, after finishing dropping initiator ammonium persulfate APS, keeping the temperature and reacting for 4h to obtain the aqueous tackifying resin emulsion.
Specific example 2:
210g of IPDI and 900g of PPG are added into a 500mL four-neck flask provided with a stirrer, a reflux condenser tube and a thermometer, after the temperature of the system is raised to 80 ℃, 3-4 drops of catalyst DBTDL are dripped, and the reaction is carried out for 2h under the protection of N2, so as to obtain the polyurethane prepolymer containing the active group-NCO. Cooling to 50 ℃, dropwise adding 8g of BDO, 12g of DMPA and 2.5g of TMP, heating to 80 ℃, dropwise adding 3-4 drops of catalyst DBTDL, reacting for 3 hours until-NCO reaches a preset value. Cooling to 65 ℃, adding 27g of hydroxypropyl methacrylate HPMA, and keeping the temperature for 2 h; then the temperature is reduced to 30 ℃, and a certain amount of triethylamine TEA is added for neutralization for 15 min. Adding deionized water, and emulsifying and dispersing the system at a high speed to obtain the PU aqueous dispersion with the end containing unsaturated double bonds.
Adding a small amount of emulsifier SDS and deionized water into the seed emulsion PU for pre-emulsification for 30min, slowly dropwise adding acrylic monomers in which 1300g of terpene resin and disproportionated rosin are dissolved, wherein the weight of the acrylic monomers is 800g, and the weight ratio of the terpene resin to the disproportionated rosin is 1: 3; after swelling for 2h, heating to 82 ℃, adding a pH buffering agent NaHCO3, after finishing dropping initiator ammonium persulfate APS, keeping the temperature and reacting for 4h to obtain the aqueous tackifying resin emulsion.
Specific example 3:
230g of IPDI and 1000g of PPG are added into a 500mL four-neck flask provided with a stirrer, a reflux condenser tube and a thermometer, after the temperature of the system is raised to 80 ℃, 3-4 drops of catalyst DBTDL are dripped, and the reaction is carried out for 2h under the protection of N2, so as to obtain the polyurethane prepolymer containing the active group-NCO. Cooling to 50 ℃, dropwise adding 7g of BDO, 13g of DMPA and 3g of TMP, heating to 80 ℃, dropwise adding 3-4 drops of catalyst DBTDL, reacting for 3 hours until-NCO reaches a preset value. Cooling to 65 ℃, adding 29g of hydroxypropyl methacrylate HPMA, and preserving the temperature for 2 h; then the temperature is reduced to 30 ℃, and a certain amount of triethylamine TEA is added for neutralization for 15 min. Adding deionized water, and emulsifying and dispersing the system at a high speed to obtain the PU aqueous dispersion with the end containing unsaturated double bonds.
Adding a small amount of emulsifier SDS and deionized water into the seed emulsion PU for pre-emulsification for 30min, slowly dropwise adding an acrylic monomer dissolved with 1400g of terpene resin and rosin ester, wherein the weight of the acrylic monomer is 850g, and the weight ratio of terpene resin to rosin ester is 3: 1; after swelling for 2h, heating to 82 ℃, adding a pH buffering agent NaHCO3, after finishing dropping initiator ammonium persulfate APS, keeping the temperature and reacting for 4h to obtain the aqueous tackifying resin emulsion.
Specific example 4:
220g of IPDI and 900g of PPG are added into a 500mL four-neck flask provided with a stirrer, a reflux condenser tube and a thermometer, after the temperature of the system is raised to 80 ℃, 3-4 drops of catalyst DBTDL are dripped, and the reaction is carried out for 2h under the protection of N2, so as to obtain the polyurethane prepolymer containing the active group-NCO. Cooling to 50 ℃, dropwise adding 8g of BDO, 12g of DMPA, 2.5g of TMP and 1.5g of sodium allyl succinic acid alkyl ester sulfonate, heating to 80 ℃, dropwise adding 3-4 drops of catalyst DBTDL, and reacting for 3 hours until-NCO reaches a preset value. Cooling to 65 ℃, adding 28g of hydroxypropyl methacrylate HPMA, and keeping the temperature for 2 h; then the temperature is reduced to 30 ℃, and a certain amount of triethylamine TEA is added for neutralization for 15 min. Adding deionized water, and emulsifying and dispersing the system at a high speed to obtain the PU aqueous dispersion with the end containing unsaturated double bonds.
Adding a small amount of emulsifier SDS and deionized water into the seed emulsion PU for pre-emulsification for 30min, slowly dropwise adding an acrylic monomer dissolved with 1300g of terpene resin and rosin ester, wherein the weight of the acrylic monomer is 900 g; the weight ratio of the terpene resin to the rosin ester is 1: 2; after swelling for 2h, heating to 82 ℃, adding a pH buffering agent NaHCO3, after finishing dropping initiator ammonium persulfate APS, keeping the temperature and reacting for 4h to obtain the aqueous tackifying resin emulsion.
Comparative example 1
220g of IPDI and 900g of PPG are added into a 500mL four-neck flask provided with a stirrer, a reflux condenser tube and a thermometer, after the temperature of the system is raised to 80 ℃, 3-4 drops of catalyst DBTDL are dripped, and the reaction is carried out for 2h under the protection of N2, so as to obtain the polyurethane prepolymer containing the active group-NCO. Cooling to 50 ℃, dropwise adding 8g of BDO, 12g of DMPA and 2.5g of TMP, heating to 80 ℃, dropwise adding 3-4 drops of catalyst DBTDL, reacting for 3 hours until-NCO reaches a preset value. Then the temperature is reduced to 30 ℃, and a certain amount of triethylamine TEA is added for neutralization for 15 min. The system is emulsified and dispersed at high speed to obtain the PU aqueous dispersion.
Adding a small amount of emulsifier SDS and deionized water into the seed emulsion PU for pre-emulsification for 30min, and slowly dropwise adding acrylic monomers dissolved with 1200g of terpene resin and rosin ester, wherein the acrylic monomers are 800 g; the weight ratio of the terpene resin to the rosin ester is 1: 1; after swelling for 2h, heating to 82 ℃, adding a pH buffering agent NaHCO3, after finishing dropping initiator ammonium persulfate APS, keeping the temperature and reacting for 4h to obtain the aqueous tackifying resin emulsion.
The advantages of examples 1-4 are as follows:
the adhesive does not contain organic solvent, and can be used for adhesive products with higher environmental protection requirements such as food packaging and the like; the product has excellent storage stability by adopting a self-emulsifying process; the initial viscosity and the bonding strength of the adhesive can be improved by introducing polyurethane and acrylate high polymers.
To further demonstrate the advantages of the present invention, tests were conducted in conjunction with the following test items
And (3) testing items:
(1) testing the viscosity of the emulsion;
(2) pH value
(3) Initial tack test: GB/T4852-
(4)180 ° peel strength test: GB/T2792-
(5) And (3) testing the storage stability: standing at room temperature, and checking whether the emulsion has a layering phenomenon.
Table 1 shows the test results of examples 1 to 4 and comparative example 1
The above description is only exemplary of the invention, and any modification, equivalent replacement, and improvement made within the spirit and scope of the present invention should be considered within the scope of the present invention.
Claims (5)
1. The preparation method of the environment-friendly water-based tackifier is characterized by comprising the following steps of:
step 1: adding isophorone diisocyanate and polypropylene glycol into a reactor, and reacting for a period of time at 78-82 ℃ in the presence of a catalyst dibutyltin dilaurate to obtain a polyurethane prepolymer;
step 2: dropwise adding dimethylolpropionic acid, trimethylolpropane and 1, 4-butanediol into the polyurethane prepolymer, and reacting for a period of time in the presence of a catalyst dibutyltin dilaurate;
and step 3: reducing the temperature of the system to 63-67 ℃, adding hydroxypropyl methacrylate, and reacting for a period of time;
and 4, step 4: adding a neutralizing agent to adjust the pH value of the system to obtain a PU aqueous dispersion with an unsaturated double bond at the tail end;
and 5: adding an emulsifier and deionized water to emulsify a system, then dropwise adding an acrylic monomer in which terpene resin and rosin ester or disproportionated rosin are dissolved, swelling for a period of time, heating to 80-85 ℃, adding a pH buffering agent and adding an initiator, and keeping the temperature for a period of time to remove residual monomers;
the step 2 also comprises 1-2 parts by weight of sodium allyl succinic acid alkyl ester sulfonate.
2. The preparation method of the environment-friendly aqueous tackifier according to claim 1, wherein the environment-friendly aqueous tackifier comprises the following raw materials in parts by weight:
200 parts of isophorone diisocyanate and 230 parts of;
800 portions of polypropylene glycol and 1000 portions of polypropylene glycol;
11-13 parts of dimethylolpropionic acid;
2-3 parts of trimethylolpropane;
7-9 parts of 1, 4-butanediol;
26-29 parts by weight of hydroxypropyl methacrylate;
1200-1400 parts by weight of terpene resin and rosin ester or disproportionated rosin;
500-600 parts by weight of acrylic monomer;
7000 portions of deionized water and 8000 portions.
3. The method for preparing the environment-friendly aqueous tackifier according to claim 1, wherein the emulsifier in the step 5 is SDS; the amount of SDS is 15-20 parts by weight.
4. The method for preparing the environment-friendly aqueous tackifier according to claim 1, wherein the reaction time of the step 1 is 2 hours, the reaction time of the step 2 is 3 hours, the reaction time of the step 3 is 2 hours, and the swelling time of the step 5 is 2 hours.
5. An environment-friendly aqueous tackifier, characterized by: prepared by the process as claimed in any one of claims 1 to 4.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103031093A (en) * | 2012-12-12 | 2013-04-10 | 常州大学 | Method for preparing water-based urethane acrylate pressure-sensitive adhesive |
| CN105085854A (en) * | 2014-05-09 | 2015-11-25 | 武汉强力荷新材料有限公司 | Preparation method of solvent-free environment-friendly aqueous polyurethane emulsion with multi-model particle size distribution, high solid content, and low viscosity |
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| CN101641418B (en) * | 2007-03-21 | 2012-09-05 | 艾利丹尼森公司 | Pressure sensitive adhesives |
| CN102816536A (en) * | 2011-06-08 | 2012-12-12 | 苏州达同新材料有限公司 | Adhesive tape used for solar cell assembly and preparation method thereof |
| CN102993685A (en) * | 2012-11-23 | 2013-03-27 | 青岛文创科技有限公司 | Rosin-based waterborne polyurethane acrylate composite emulsion |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103031093A (en) * | 2012-12-12 | 2013-04-10 | 常州大学 | Method for preparing water-based urethane acrylate pressure-sensitive adhesive |
| CN105085854A (en) * | 2014-05-09 | 2015-11-25 | 武汉强力荷新材料有限公司 | Preparation method of solvent-free environment-friendly aqueous polyurethane emulsion with multi-model particle size distribution, high solid content, and low viscosity |
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