CN108251038B - Special solvent-based bi-component polyurethane adhesive for milk cover film and preparation method thereof - Google Patents
Special solvent-based bi-component polyurethane adhesive for milk cover film and preparation method thereof Download PDFInfo
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- CN108251038B CN108251038B CN201810139628.8A CN201810139628A CN108251038B CN 108251038 B CN108251038 B CN 108251038B CN 201810139628 A CN201810139628 A CN 201810139628A CN 108251038 B CN108251038 B CN 108251038B
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
-
- 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
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
- C08G18/4247—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids
- C08G18/425—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids the polyols containing one or two ether groups
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
- C08G18/6644—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
Abstract
The invention discloses a special solvent-based bi-component polyurethane adhesive for a milk cover film and a preparation method thereof, wherein the adhesive consists of an adhesive A and an adhesive B, the adhesive A takes ethylene glycol, neopentyl glycol, 1, 4-butanediol, dimethyl terephthalate and diethylene glycol as raw materials, tetrabutyl titanate as a catalyst, and a reaction system is protected by nitrogen. Controlling the reaction temperature, the heating rate and the heat preservation time. Adding sebacic acid and isophthalic acid, controlling reaction conditions to obtain polyester polyol with a specific acid value, and reacting the polyester polyol with MDI (diphenylmethane diisocyanate) and ethyl acetate to obtain an A glue; the adhesive B is prepared by using TDI, MDI-50, ethyl acetate and trimethylolpropane as raw materials and controlling the reaction temperature and time. The special solvent-based bi-component polyurethane adhesive has the advantages that: the composite material obtained by the adhesive has excellent peeling strength. The preparation process has easily controlled parameters and environment-friendly preparation process.
Description
Technical Field
The invention relates to a special solvent-type bi-component polyurethane adhesive for a milk cover film and a preparation method thereof, belonging to the field of research of polyurethane adhesive materials.
Background
The yoghourt is liquid substance with high protein and fat content, and is determined to be sensitive to oxygen, so in order to ensure the shelf life of the yoghourt, the yoghourt in the plastic cup is usually sealed by adopting an aluminum foil composite film as a cover film, if the composite fastness between single-layer films of the cover film is low, namely the peeling strength when the single-layer films are peeled is low, the phenomenon that the cover film is not separated from a cup body but is separated at the sticking part of the single-layer films of the cover film is easy to occur when the cover film is torn, the eating of consumers is inconvenient, and the enterprise image is directly influenced. Therefore, each food enterprise should strengthen the composite fastness detection of the film covering material. According to the packaging requirements of products, the peel strength of an aluminum foil composite film is more than 15(N.15mm), but the conventional common glue cannot meet the requirement of high peel strength, and in order to overcome the defects of the conventional products and meet the new requirements of the market, the applicant develops a novel special solvent-type bi-component polyurethane adhesive for a milk cover film.
Disclosure of Invention
The invention aims to provide a special solvent-type bi-component polyurethane adhesive for a milk cover film and a preparation method thereof.
The technical scheme adopted by the invention is as follows:
a special solvent-based bi-component polyurethane adhesive for a milk cover film is composed of an adhesive A and an adhesive B, and is characterized in that: the preparation method comprises the following steps:
step 1, preparation of glue A:
77-79 g of ethylene glycol, 99-101 g of neopentyl glycol, 95-97 g of 1, 4-butanediol, 106-109 g of dimethyl terephthalate and 139-141 g of diethylene glycol are respectively put into a 1000mL four-neck flask, 0.15g of tetrabutyl titanate is added to be used as a catalyst, and the reaction system needs nitrogen protection. When the reaction temperature reaches 155 ℃, the reaction system starts to produce alcohol, the temperature rise rate needs to be controlled, when the reaction temperature reaches 190 ℃, the temperature rise is changed into a heat preservation state, and the heat preservation time is 1 h. And after the heat preservation time is finished, taking 312g of sebacic acid and 165g of isophthalic acid and the system, gradually heating to 235 ℃, preserving the heat for 3.5 hours, sampling and measuring the acid value, and if the acid value is lower than 15mg KOH/g, vacuumizing for 3 hours under the conditions that the temperature is controlled to be 220-230 ℃ and the pressure is-0.1 MPa to obtain the polyester polyol with the acid value of less than or equal to 1mg KOH/g and the hydroxyl value of 50 +/-5 mg KOH/g. Respectively taking 800g of the polyester polyol obtained above, 62g of MDI and 368g of ethyl acetate in a four-neck flask, and reacting for 5 hours at the temperature of 90-95 ℃ to obtain glue A;
step 2, preparing glue B:
taking 373-376 g of TDI, 248-251 g of MDI-50 and 254-256 g of ethyl acetate in a 1000mL four-neck flask, adding 28-31 g of trimethylolpropane when the temperature is raised to 45 ℃, carrying out exothermic reaction, properly controlling cooling, adding 66-69 g of trimethylolpropane after 30min, controlling the temperature to be 78 ℃, and carrying out heat preservation reaction for 3h to obtain the B glue.
Further, in step 1, the mass of ethylene glycol was 78g, the mass of neopentyl glycol was 100g, the mass of 1, 4-butanediol was 96g, the mass of dimethyl terephthalate was 107.3g, and the mass of diethylene glycol was 140.8 g; the heat preservation temperature when alcohol is discharged is 190 ℃; the weight of isophthalic acid is 165g, and the weight of sebacic acid is 312 g; the mass of the polyester polyol was 800g, the mass of MDI was 62g, and the mass of ethyl acetate was 368 g.
Further, in step 2, the mass of TDI was 375g, the mass of MDI was 250g, the mass of ethyl acetate was 255g, the total mass of trimethylolpropane was 97g, and the reaction temperature was 78 ℃.
The novel special solvent-based bi-component polyurethane adhesive for the milk cover film has the advantages that: the composite material obtained by the adhesive has excellent peeling strength.
The preparation method has the advantages that: the preparation process has easily controlled parameters and environment-friendly preparation process.
Detailed Description
The invention will now be further illustrated by reference to specific examples, which are intended to be illustrative of the invention and are not intended to be a further limitation of the invention.
The first embodiment is as follows:
a special solvent-based bi-component polyurethane adhesive for a milk cover film is composed of an adhesive A and an adhesive B, and the preparation steps are as follows:
step 1, preparation of glue A:
78g of ethylene glycol, 100g of neopentyl glycol, 96g of 1, 4-butanediol, 107.3g of dimethyl terephthalate and 140.8g of diethylene glycol are respectively put into a 1000mL four-neck flask, 0.15g of tetrabutyl titanate is added to be used as a catalyst, and the reaction system needs nitrogen protection. When the reaction temperature reaches 155 ℃, the reaction system starts to produce alcohol, the temperature rise rate needs to be controlled, when the reaction temperature reaches 190 ℃, the temperature rise is changed into a heat preservation state, and the heat preservation time is 1 h. And after the heat preservation time is finished, taking 312g of sebacic acid and 165g of isophthalic acid and the system, gradually heating to 235 ℃, preserving the heat for 3.5 hours, sampling and measuring the acid value, and if the acid value is lower than 15mg KOH/g, vacuumizing for 3 hours under the conditions that the temperature is controlled to be 220-230 ℃ and the pressure is-0.1 MPa to obtain the polyester polyol with the acid value of less than or equal to 1mg KOH/g and the hydroxyl value of 50 +/-5 mg KOH/g. 800g of the polyester polyol, 62g of MDI and 368g of ethyl acetate obtained in the previous step are respectively put into a four-neck flask and reacted for 5 hours at the temperature of 90-95 ℃ to obtain the A glue.
Step 2, preparing glue B:
respectively putting 375g TDI, 250g MDI-50 and 255g ethyl acetate into a 1000mL four-neck flask, adding 30g trimethylolpropane when the temperature is raised to 45 ℃, properly controlling the cooling for 30min, adding 67g trimethylolpropane after the exothermic reaction, controlling the temperature to be 78 ℃, and carrying out heat preservation reaction for 3h to obtain the B glue.
Step 3, preparing a solvent type bi-component polyurethane adhesive:
the solvent-type bi-component polyurethane adhesive can be obtained by mixing the adhesive A and the adhesive B in a ratio of 5:1 and then adding a certain amount of ethyl acetate.
Barge strength test 1:
to examine the effect of the amount of sebacic acid on the peel strength of the composite, the molar ratio of sebacic acid to isophthalic acid was adjusted to 1.8:1, 1.7:1, 1.6:1, 1.55:1, 1.5:1, 1.4:1, respectively. Then adding the prepared solvent-based bi-component polyurethane adhesive into a sizing system of a solvent-based film covering machine, wherein the sizing amount is 3.5g/m2With a working concentration of 32%, a composite material was prepared using a thick aluminum foil and a thick PE film as substrates, and after further aging, the peel strength was tested according to the procedure of GB/T2791-1995, and the results shown in table 1 show that as the ratio of sebacic acid was decreased, the peel strength increased first and then decreased, and reached the highest peel strength at a molar ratio of 1.55: 1. The peel strength is increased because: the proportion of the isophthalic acid is increased, so that the glue becomes hard; the peel strength is reduced because: the continuous increase in the proportion of isophthalic acid causes the reaction rate of the polyester to decrease, and consequently the viscosity of the glue to decrease.
TABLE 1
Barge strength test 2:
in order to examine the influence of the ratio of neopentyl glycol to 1, 4-butanediol on the peel strength of the composite material, the molar ratios of neopentyl glycol to 1, 4-butanediol were adjusted to 1.2:1, 1.0:1, 0.9:1, 0.8:1, 0.6:1, respectively. Then adding the prepared solvent-based bi-component polyurethane adhesive into a sizing system of a solvent-based film covering machine, wherein the sizing amount is 3.5g/m2Working concentration 32%, using a thick aluminum foil and a thick PE film as substrates, a composite was prepared, and after further curing, the peel strength was tested according to the procedure of GB/T2791-1995, with the results shown in table 2 that as the proportion of neopentyl glycol was decreased, the peel strength increased first and then decreased, and reached the highest peel strength at a molar ratio of 0.9: 1. The peel strength is increased because: the proportion of neopentyl glycol is reduced, so that the glue becomes hard; the peel strength may be reduced by: the continuous increase in the proportion of 1, 4-butanediol leads to a reduction in the degree of internal crosslinking of the polyester.
TABLE 2
And (3) anti-aging test:
adding the prepared solvent-based bi-component polyurethane adhesive into a gluing system of a solvent-based film laminating machine, wherein the gluing amount is 3.5g/m2The working concentration is 32%, the composite material is prepared by taking a thick aluminum foil and a thick PE film as substrates, after further curing and aging, the peel strength of the composite material is tested according to the steps of GB/T2791-1995, and the result shows that the peel strength of the composite material can still maintain 16.7(N.15mm) after the composite material is placed for one month, which indicates that the solvent-type bi-component polyurethane adhesive has excellent anti-aging performance.
The solvent type bi-component polyurethane adhesive prepared by the invention has the advantages that the parameters of the preparation process are easy to control, the preparation process is environment-friendly, and the composite material obtained by the adhesive has excellent peel strength.
Claims (3)
1. A special solvent-based bi-component polyurethane adhesive for a milk cover film is composed of an adhesive A and an adhesive B, and is characterized in that: the preparation method comprises the following steps:
step 1, preparation of glue A:
respectively taking 77-79 g of ethylene glycol, 99-101 g of neopentyl glycol, 95-97 g of 1, 4-butanediol, 106-109 g of dimethyl terephthalate and 139-141 g of diethylene glycol into a 1000mL four-neck flask, adding 0.15g of tetrabutyl titanate as a catalyst, wherein the reaction system needs nitrogen protection, when the reaction temperature reaches 155 ℃, starting alcohol discharge from the reaction system, controlling the heating rate, changing the heating state into a heat preservation state when the reaction temperature reaches 190 ℃, preserving the heat for 1h, after the heat preservation time is finished, taking 312g of sebacic acid and 165g of isophthalic acid and the system, gradually heating to 235 ℃, preserving the heat for 3.5h, sampling and measuring the acid value, and when the acid value is lower than 15mgKOH/g, controlling the temperature to be 220-230 ℃ and vacuumizing for 3h under the pressure of-0.1 Mpa
Then, polyester polyol with the acid value of less than or equal to 1mg KOH/g and the hydroxyl value of 50 +/-5 mg KOH/g is obtained, 800g of the obtained polyester polyol, 62g of MDI and 368g of ethyl acetate are respectively taken to be put into a four-neck flask and react for 5 hours at the temperature of 90-95 ℃ to obtain glue A;
step 2, preparing glue B:
taking 373-376 g of TDI, 248-251 g of MDI-50 and 254-256 g of ethyl acetate in a 1000mL four-neck flask, adding 28-31 g of trimethylolpropane when the temperature is raised to 45 ℃, carrying out exothermic reaction, properly controlling cooling, adding 66-69 g of trimethylolpropane after 30min, controlling the temperature to be 78 ℃, and carrying out heat preservation reaction for 3h to obtain the B glue.
2. The preparation method of the solvent-based two-component polyurethane adhesive special for the milk covering film according to claim 1, characterized in that: in step 1, the mass of ethylene glycol was 78g, the mass of neopentyl glycol was 100g, the mass of 1, 4-butanediol was 96g, the mass of dimethyl terephthalate was 107.3g, and the mass of diethylene glycol was 140.8 g; the heat preservation temperature when alcohol is discharged is 190 ℃; the weight of isophthalic acid is 165g, and the weight of sebacic acid is 312 g; the mass of the polyester polyol was 800g, the mass of MDI was 62g, and the mass of ethyl acetate was 368 g.
3. The preparation method of the solvent-based two-component polyurethane adhesive special for the milk covering film according to claim 1, characterized in that: in step 2, the mass of TDI was 375g, the mass of MDI was 250g, the mass of ethyl acetate was 255g, the total mass of trimethylolpropane was 97g, and the reaction temperature was 78 ℃.
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| CN201810139628.8A CN108251038B (en) | 2018-02-11 | 2018-02-11 | Special solvent-based bi-component polyurethane adhesive for milk cover film and preparation method thereof |
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| CN201810139628.8A CN108251038B (en) | 2018-02-11 | 2018-02-11 | Special solvent-based bi-component polyurethane adhesive for milk cover film and preparation method thereof |
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| CN108251038B true CN108251038B (en) | 2021-12-17 |
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Effective date of registration: 20191218 Address after: 210000 room 298, building B, No. 606, ningliu Road, Changlu street, Jiangbei new district, Nanjing City, Jiangsu Province Applicant after: Nanjing xuansi New Material Co., Ltd Address before: 213200 No. 28, Yang Chemical Industrial Park, Jintan District, Jiangsu, Changzhou Applicant before: Jiangsu LiHe Adhesive Co., Ltd. |
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