CN115806794A - Preparation method and application of polyurethane adhesive with excellent washing resistance - Google Patents
Preparation method and application of polyurethane adhesive with excellent washing resistance Download PDFInfo
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- CN115806794A CN115806794A CN202210977586.1A CN202210977586A CN115806794A CN 115806794 A CN115806794 A CN 115806794A CN 202210977586 A CN202210977586 A CN 202210977586A CN 115806794 A CN115806794 A CN 115806794A
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- polyurethane adhesive
- polyurethane
- excellent washing
- washing fastness
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- 239000004814 polyurethane Substances 0.000 title claims abstract description 60
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 60
- 239000000853 adhesive Substances 0.000 title claims abstract description 41
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 41
- 238000005406 washing Methods 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 49
- 239000003292 glue Substances 0.000 claims abstract description 25
- 239000012948 isocyanate Substances 0.000 claims abstract description 22
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 22
- 239000004970 Chain extender Substances 0.000 claims abstract description 21
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 239000007787 solid Substances 0.000 claims abstract description 10
- 238000007599 discharging Methods 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000013557 residual solvent Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 4
- 230000001502 supplementing effect Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 9
- 238000005108 dry cleaning Methods 0.000 abstract description 3
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 125000004185 ester group Chemical group 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 210000004243 sweat Anatomy 0.000 abstract description 2
- 239000004744 fabric Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000011324 bead Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 3
- 238000002310 reflectometry Methods 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical group OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- UQOQXWZPXFPRBR-UHFFFAOYSA-K bismuth dodecanoate Chemical compound [Bi+3].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O UQOQXWZPXFPRBR-UHFFFAOYSA-K 0.000 description 2
- 239000007767 bonding agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical group O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- BZNOBFUQYZPVBC-UHFFFAOYSA-N hexanedioic acid;3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO.OC(=O)CCCCC(O)=O BZNOBFUQYZPVBC-UHFFFAOYSA-N 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- -1 acrylic ester Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001795 light effect Effects 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a preparation method of polyurethane glue with excellent washing resistance, which comprises the following steps: dehydrating polyester polyol; carrying out prepolymerization reaction; adding a catalyst, and continuing the reaction; adjusting the viscosity, discharging the solid content. According to the invention, part of isocyanate and the chain extender are added firstly or the chain extender is added after all the isocyanate is added for reaction, so that the polyurethane adhesive can be subjected to prepolymerization reaction firstly, the phenomenon that bubbles are formed due to severe polyurethane reaction to influence the bonding effect of the polyurethane adhesive is avoided, and the washing resistance, the dry cleaning resistance, the solvent resistance and the sweat stain resistance are improved. And the polyester polyol with high adhesive force and low crystallization is dehydrated in vacuum in advance before reaction, so that hydrolysis of formed ester groups can be prevented, bubbles are generated in the polyurethane adhesive, and the reflecting effect is influenced. Meanwhile, by introducing a hydroxyl chain extender before or after the prepolymerization reaction, high-modulus high-molecular-weight polyurethane glue can be formed, so that the polyurethane glue has certain low-temperature resistance.
Description
Technical Field
The invention relates to a preparation method and application of polyurethane adhesive with excellent washing fastness, relates to C09J, and particularly relates to the field of adhesives.
Background
Along with the development of science and technology, people seek more and more high to the pleasing to the eye of clothing, and reflection of light surface fabric has brought new effect for the cloth innovation, passes through glue with reflecting material and cloth and combines, can bring gorgeous and dazzling effect for the cloth, but if the quality of glue is not good, reflection of light cloth after the washing of dress, reflection of light effect can significantly reduce to the reflector layer cracks easily after the insolate, falls the skin. At present, acrylic ester glue is adopted in the market as a bonding agent of reflective cloth, and the water washing resistance and the solvent resistance are poor. Polyurethane glue is used as a bonding agent of the reflective fabric, and after the glass beads of the reflective structure are introduced, the problem of sinking of the glass beads is easy to occur in the process of composite transfer, so that the general bad surface state is formed, and unqualified products are produced.
Chinese patent CN201310233459.1 discloses a preparation method of polyurethane modified acrylic resin for a reflective material, wherein a thiol alcohol monomer and an acrylate monomer are subjected to polymerization reaction to prepare active acrylic resin, and then a hydroxyl group is introduced to react with isocyanate to obtain a polyurethane structure, so that a high-temperature washing resistant adhesive is obtained, but the solid content is high, the reflective material cannot be well combined with the adhesive, and the reflective performance is poor. The Chinese invention patent CN201910202744.4 discloses UV glue for a reflective film, the reflective film and a preparation method thereof, polyurethane acrylate resin is used as a main raw material, and optical variable powder is added, so that the reflective film can present different colors along with the change of temperature, but a photoinitiator is required to be used, the reflective film needs to be processed and prepared in a dark environment, and the processing conditions are complex.
Disclosure of Invention
In order to improve the reflective effect of polyurethane glue after being washed in a reflective material and maintain the apparent effect of reflective microspheres on the surface of the glue, the first aspect of the application provides a preparation method of polyurethane glue with excellent washing fastness, which comprises the following steps:
(1) Putting polyester polyol into a reaction kettle, heating, vacuumizing, dehydrating and cooling;
(2) Adding isocyanate and partial solvent to perform prepolymerization reaction;
(3) Adding a catalyst, adding a solvent, and continuing the reaction;
(4) Adding the residual solvent, controlling the consistency and solid content of the polyurethane adhesive, adding the terminator, cooling and discharging to obtain the polyurethane adhesive.
In a preferred embodiment, the heating temperature of the polyester polyol in the step 1 is 110-130 ℃, and the vacuum degree is-0.09 to-0.1 MPa.
In a preferred embodiment, after the polyester polyol is dehydrated in the step 1, the water content is less than or equal to 500ppm, and the temperature is reduced to less than or equal to 80 ℃.
As a preferred embodiment, said step 2 further comprises adding a hydroxyl chain extender before or after the prepolymerization reaction takes place.
As a preferred embodiment, the reaction temperature of the prepolymerization reaction in the step 2 is 80-88 ℃ and the reaction time is 0.5-1h.
As a preferred embodiment, when adding the hydroxyl chain extender before the prepolymerization reaction, the isocyanate is added in two times, and the weight ratio of the isocyanate added in the two times is (80-90): (10-20).
As a preferred embodiment, when the hydroxyl chain extender is added before the prepolymerization reaction is carried out, the catalyst is added in two times, and the weight ratio of the added catalyst to the added catalyst in the two times is (0.01-0.05): (0.01-0.05).
In the experimental process, the applicant finds that the polyurethane adhesive can be subjected to prepolymerization reaction by adding part of isocyanate and the chain extender or adding the chain extender after adding all the isocyanate for reaction, so that the phenomenon that bubbles are formed due to severe polyurethane reaction to influence the bonding effect of the polyurethane adhesive is avoided. And the polyurethane adhesive prepared by the reaction of the low-crystallinity polyester diol, the isocyanate and the chain extender has good elasticity and certain creep resistance, and the probable reason is guessed to be that: the polyester diol contains a small amount of crystals, and the crystals are coordinated with the reaction of isocyanate and a chain extender to form high-modulus high-molecular-weight polyurethane glue, so that when a reflective material is doped into the polyurethane glue for composite transfer, the lower limit of glass beads can not be caused, and the surface state of a reflective surface can be obviously improved. And a prepolymerization process is adopted in the reaction process, so that the polyurethane is prevented from forming local over-hard or over-soft in the processing process, and a polyurethane adhesive with stable service performance and good elasticity can be formed.
As a preferable embodiment, the reaction temperature in the step 3 is 80-88 ℃ and the reaction time is 0.5-3h.
In a preferred embodiment, the polyurethane gel in step 4 has a consistency of 6000 to 10000mpa.s and a solid content of 35 to 45%.
The second aspect of the invention provides application of the preparation method of the polyurethane glue with excellent washing fastness, which is applied to preparation of polyurethane glue of a reflective material.
Compared with the prior art, the invention has the following beneficial effects:
(1) According to the preparation method of the polyurethane adhesive with excellent washing fastness, part of isocyanate and the chain extender are added firstly or the chain extender is added after the reaction of all the isocyanate, so that the polyurethane adhesive can be subjected to prepolymerization reaction firstly, the phenomenon that bubbles are formed due to severe polyurethane reaction is avoided, the bonding effect of the polyurethane adhesive is influenced, and the washing fastness, the dry cleaning resistance, the solvent resistance and the sweat resistance are improved.
(2) According to the preparation method of the polyurethane adhesive with excellent washing fastness, the polyester polyol with high adhesive force and low crystallization is dehydrated in vacuum in advance before reaction, so that hydrolysis of formed ester groups can be prevented, bubbles are generated in the polyurethane adhesive, and the reflecting effect is influenced.
(3) According to the preparation method of the polyurethane glue with excellent washing fastness, the hydroxyl chain extender is introduced before or after the prepolymerization reaction, so that the high-modulus and high-molecular-weight polyurethane glue can be formed, and the polyurethane glue has certain low-temperature resistance.
Detailed Description
Example 1
A preparation method of polyurethane glue with excellent washing fastness comprises the following steps:
(1) Putting polyester polyol into a reaction kettle, heating, vacuumizing, dehydrating and cooling;
(2) Adding isocyanate and partial solvent to perform prepolymerization reaction;
(3) Adding a catalyst, adding a solvent, and continuing the reaction;
(4) Adding the residual solvent, controlling the consistency and solid content of the polyurethane adhesive, adding the terminator, cooling and discharging to obtain the polyurethane adhesive.
In the step 1, the heating temperature of the polyester polyol is 120 ℃, the vacuum degree is-0.1 MPa, the water content of the polyester polyol is 500ppm after the polyester polyol is dehydrated, and the temperature is reduced to 75 ℃.
The specific steps of the step 2 are as follows: adding a hydroxyl chain extender, isocyanate with the formula amount of 85wt% and a solvent with the formula amount of 10wt%, and carrying out prepolymerization reaction for 0.5h at the reaction temperature of 85 ℃ for 0.5h;
the specific steps of the step 3 are as follows: adding 0.02 weight part of catalyst, continuing to react for 0.5h, then adding the residual isocyanate, and continuing to react for 1.5h at the reaction temperature of 85 ℃;
the specific steps of the step 4 are as follows: adding 0.02 weight part of catalyst, continuing the reaction, adding the residual solvent, controlling the consistency of the polyurethane adhesive to 8000mpa.s and the solid content to 40%, adding a terminator, cooling to 50 ℃, and packaging and discharging in a nitrogen atmosphere.
The polyester polyol is poly (3-methyl-1, 5-pentanediol adipate), the adding amount is 40 parts by weight, and the CAS:39751-34-3. Molecular weight 2000, available from the Goodpasture chemical industry network.
The isocyanate is hexamethylene diisocyanate and 12 parts by weight, the solvent is a combination of ethyl acetate and acetone, and the weight ratio is 2: the total weight of the catalyst is 66 parts by weight, the catalyst is 0.04 part by weight of bismuth laurate, and the hydroxyl chain extender is 5 parts by weight of dimethylolpropionic acid. The terminating agent is malic acid, 0.03 weight portion.
Example 2
A preparation method of polyurethane glue with excellent washing fastness comprises the following steps:
(1) Putting polyester polyol into a reaction kettle, heating, vacuumizing, dehydrating and cooling;
(2) Adding isocyanate and partial solvent to perform prepolymerization reaction;
(3) Adding a catalyst, supplementing a solvent and continuing the reaction;
(4) Adding the residual solvent, controlling the consistency and solid content of the polyurethane adhesive, adding the terminator, cooling and discharging to obtain the polyurethane adhesive.
In the step 1, the heating temperature of the polyester polyol is 120 ℃, the vacuum degree is-0.1 MPa, the water content of the polyester polyol is 500ppm after the polyester polyol is dehydrated, and the temperature is reduced to be below 80 ℃.
The specific steps of the step 2 are as follows: adding a hydroxyl chain extender, all isocyanate and a solvent with the formula amount of 10wt%, carrying out prepolymerization reaction for 0.5h at the reaction temperature of 85 ℃ for 0.5h, then adding the hydroxyl chain extender, and continuing the reaction for 1 h;
the specific steps of the step 3 are as follows: adding 0.04 part by weight of catalyst and 50wt% of solvent according to the formula amount, continuously reacting for 3 hours,
the specific steps of the step 4 are as follows: adding the residual solvent, controlling the consistency of the polyurethane adhesive to 8000mpa.s and the solid content to 40%, adding a terminator, cooling to 50 ℃, and packaging and discharging under the nitrogen atmosphere.
The polyester polyol is poly (3-methyl-1, 5-pentanediol adipate), the adding amount is 40 parts by weight, CAS:39751-34-3. Molecular weight 2000, available from the Goodpasture chemical industry network.
The isocyanate is hexamethylene diisocyanate and 12 parts by weight, the solvent is a combination of ethyl acetate and acetone, and the weight ratio is 2: the total weight of the catalyst is 66 parts by weight, the catalyst is 0.04 part by weight of bismuth laurate, and the hydroxyl chain extender is 5 parts by weight of dimethylolpropionic acid. The terminating agent is malic acid, 0.03 weight portion.
Example 3
A commercially available acrylate adhesive for reflecting materials is available from En chemical industry Co., ltd, anhui, under the trade name SA-226.
And (4) performance testing:
the glue of the examples 1,2 and 3 and the glass beads are mixed and coated on hydrophobic base cloth (the base cloth is chemical fiber fabric), the mixing amount of the glass beads is 40% of the weight of the glue, the coating thickness is 80 microns, and the high-brightness reflective material is obtained after drying.
1. Dry cleaning resistance: the obtained high-brightness reflecting material is dry-cleaned for 25 times, and the reflectivity is tested by using a retroreflection coefficient meter.
2. Washing resistance: and washing the obtained high-brightness reflecting material for 25 times, and testing the reflectivity by using a retroreflection coefficient instrument.
3. Wear resistance: and pressing a heavy hammer with the mass of 198g on the high-brightness reflecting material, rubbing for 5000 times, observing the reflecting surface of the reflecting material, and testing the reflectivity.
4. Fastness to bonding with a base fabric: the peel strength of the glue and the base fabric was tested according to GB/T2791-1995 standard.
5. Low temperature resistance: the obtained high-brightness reflecting material is bent for 5000 times at the temperature of minus 30 ℃, and the reflecting surface performance of the material is observed.
The test results are shown in Table 1.
TABLE 1
Claims (10)
1. The preparation method of the polyurethane adhesive with excellent washing fastness is characterized by comprising the following steps:
(1) Putting polyester polyol into a reaction kettle, heating, vacuumizing, dehydrating and cooling;
(2) Adding isocyanate and partial solvent to perform prepolymerization reaction;
(3) Adding a catalyst, supplementing a solvent and continuing the reaction;
(4) Adding the residual solvent, controlling the consistency and solid content of the polyurethane adhesive, adding the terminator, cooling and discharging to obtain the polyurethane adhesive.
2. The method for preparing polyurethane adhesive with excellent washing fastness according to claim 1, wherein the heating temperature of polyester polyol in the step 1 is 110-130 ℃, and the vacuum degree is-0.09 to-0.1 MPa.
3. The method for preparing the polyurethane adhesive with excellent washing fastness according to the claim 1, wherein the water content of the dehydrated polyester polyol in the step 1 is less than or equal to 500ppm, and the temperature is reduced to be below 80 ℃.
4. The method for preparing polyurethane adhesive with excellent washing fastness according to claim 1, wherein the step 2 further comprises adding a hydroxyl chain extender before or after the prepolymerization reaction.
5. The method for preparing polyurethane adhesive with excellent washing fastness according to claim 1, wherein the reaction temperature of the prepolymerization reaction in the step 2 is 80-88 ℃ and the reaction time is 0.5-1h.
6. The method for preparing polyurethane adhesive with excellent washing fastness according to claim 4, wherein when the hydroxyl chain extender is added before the prepolymerization reaction, the isocyanate is added in two times, and the ratio of the addition amount of the isocyanate in the two times is (80-90): (10-20).
7. The method for preparing polyurethane adhesive with excellent washing fastness according to claim 4, wherein when the hydroxyl chain extender is added before the prepolymerization reaction, the catalyst is added in two times, and the ratio of the addition amount of the two catalysts is (0.01-0.05): (0.01-0.05).
8. The method for preparing polyurethane adhesive with excellent washing fastness according to claim 1, wherein the reaction temperature in the step 3 is 80-88 ℃ and the reaction time is 0.5-3h.
9. The method for preparing polyurethane adhesive with excellent washing fastness as claimed in claim 1, wherein the polyurethane adhesive in step 4 has a consistency of 6000-10000mpa.s and a solid content of 35-45%.
10. Use of the process for the preparation of polyurethane glues with excellent wash fastness according to any of claims 1-9, characterized in that it is used in the preparation of polyurethane glues for retroreflective materials.
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| CN202210977586.1A CN115806794A (en) | 2022-08-15 | 2022-08-15 | Preparation method and application of polyurethane adhesive with excellent washing resistance |
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| CN202210977586.1A CN115806794A (en) | 2022-08-15 | 2022-08-15 | Preparation method and application of polyurethane adhesive with excellent washing resistance |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106047262A (en) * | 2016-07-06 | 2016-10-26 | 江苏东邦科技有限公司 | Preparation process of polyurethane resin compound glue for reflective garments |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106047262A (en) * | 2016-07-06 | 2016-10-26 | 江苏东邦科技有限公司 | Preparation process of polyurethane resin compound glue for reflective garments |
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