CN112608448A - Preparation method of high-elasticity hand-feeling wear-resistant multi-arm photocuring resin - Google Patents
Preparation method of high-elasticity hand-feeling wear-resistant multi-arm photocuring resin Download PDFInfo
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- 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
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- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/69—Polymers of conjugated dienes
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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Abstract
A preparation method of high-elasticity hand-feeling wear-resistant multi-arm photocuring resin belongs to the technical field of functional polyurethane materials. The elastic wear-resistant resin with elasticity and wear resistance is synthesized by modifying trifunctional isocyanate, isophorone diisocyanate (IPDI), polycarbonate diol (PCDL), pentaerythritol triacrylate (PETA) and diol. The multifunctional group branched polyurethane wear-resistant elastic resin prepared by the method is an excellent high-molecular synthetic material, has the elasticity of rubber and the hardness of plastic, and also has good mechanical property, wear resistance and rebound resilience; has good application prospect in the application field of elastic hand feeling materials.
Description
Technical Field
The invention relates to a preparation method of high-elasticity hand-feeling wear-resistant multi-arm type photocuring resin, belonging to the technical field of functional polyurethane materials.
Background
In the prior art, in order to enable certain parts which often need hand touch, such as a blowing cylinder handle, an MP3 shell, a mouse, a mobile phone shell, a telescope, an umbrella handle and the like, to not give cold ice, rough and stiff feeling to people any more, soft and smooth touch feeling is provided, and the elastic touch paint is suitable for transportation. The elastic hand feeling paint mainly adopts elastic resin, has more bright appearance and hand feeling like leather, and has wide application, large using amount and considerable market prospect.
The pure straight-chain polyester resin has low price and good cost performance, but is weaker than the modified polyester resin in certain main performances (such as hand feeling, scratch resistance, wear resistance and other performance tests). In order to solve the above problems, it is necessary to develop a multifunctional branched polyurethane abrasion resistant elastic resin.
Disclosure of Invention
The invention aims to overcome the defects and provide a preparation method of the high-elasticity hand-feeling wear-resistant multi-arm photocuring resin, and the prepared resin has the elasticity of rubber and the hardness of plastic and also has good mechanical property, wear resistance and rebound resilience.
The technical scheme of the invention is a preparation method of high-elasticity hand-feeling wear-resistant multi-arm photocuring resin, which comprises the following steps:
(1) adding diisocyanate and dihydric alcohol into a reaction container, dropwise adding a catalyst diluted by ethyl acetate, and heating for reaction; adding pentaerythritol triacrylate PETA and glycol for end capping, and keeping the temperature and stirring continuously to obtain a component 1;
(2) adding trifunctional isocyanate and a catalyst into a reaction container, heating for reaction, slowly dripping the component 1 prepared in the step (1) into the reaction container, and continuing to perform heat preservation reaction;
(3) and (3) adding hydroxyl-terminated polybutadiene HTPB into the reaction container in the step (2) for continuous reaction, and adding pentaerythritol triacrylate for end-capping treatment to obtain the high-elasticity hand-feeling wear-resistant multi-arm photocuring resin.
Further, the trifunctional isocyanate is specifically a trimer of HDI.
Further, the catalyst is specifically one of dibutyltin dilaurate DBTDL, an organic bismuth catalyst, dimethylcyclohexylamine or methyldiethylenetriamine.
Further, the diisocyanate in the step (1) is specifically isophorone diisocyanate (IPDI) or Toluene Diisocyanate (TDI);
the dihydric alcohol is polycarbonate dihydric alcohol PCDL or polytetrahydrofuran PTMG.
Further, the hydroxyl-terminated polybutadiene HTPB obtained in the step (3) is a rubber-elastic hydroxyl-terminated diol.
The step (1) is specifically as follows: adding 8-25g of diisocyanate and 13-50g of dihydric alcohol into a dry four-neck flask connected with a stirrer, a condenser pipe, a nitrogen conduit and a constant pressure titration funnel; continuously adding 1-3 drops of catalyst diluted by 15-20mL of ethyl acetate, heating to 60-70 ℃, and continuously reacting for 2-3h after the temperature is reached; adding 6-30g of pentaerythritol triacrylate PETA and 1-5g of glycol for end capping, keeping the temperature to 60-70 ℃, and continuously stirring for 4-5h to obtain the component 1.
The step (2) is specifically as follows: adding 10-35g of trifunctional isocyanate and 1-2 drops of catalyst into a dry four-neck flask connected with a stirrer, a condenser pipe, a nitrogen conduit and a constant pressure titration funnel, and heating to 60-70 ℃; slowly dropping the component 1 prepared in the step (1) into the four-neck flask, and reacting for 2-3h at 60-70 ℃.
The step (3) is specifically as follows: adding 30-55g of hydroxyl-terminated polybutadiene HTPB into the four-neck flask obtained in the step (2), continuing to react for 2-3h at 60-70 ℃, and adding 1-5g of pentaerythritol triacrylate for end-capping treatment; obtaining the multi-arm photocureable resin with high elasticity and wear resistance.
Further, in the step (3), a solvent is added in the reaction process to adjust the viscosity, so that the polymer does not have a rod climbing phenomenon in the reaction.
Further, the solvent is tetrahydrofuran THF, acetone ACE or dimethylformamide DMF in particular.
The invention has the beneficial effects that: the multifunctional group branched polyurethane wear-resistant elastic resin prepared by the method is an excellent high-molecular synthetic material, has the elasticity of rubber and the hardness of plastic, and also has good mechanical property, wear resistance and rebound resilience; has good application prospect in the application field of elastic hand feeling materials.
Drawings
FIG. 1 influence of hard segment content on mechanical properties of elastic abrasion-resistant resin.
Detailed Description
Example 1
(1) 8.8g (0.04 mol) of IPDI and 40g (0.02 mol) of PCDL are introduced into a dry four-neck flask equipped with stirrer, condenser, nitrogen conduit and constant pressure titration funnel; adding 3 drops of catalyst DBTDL diluted by 20mL of ethyl acetate, heating to 60 ℃, and continuing to react for 2 hours after the temperature is reached; adding 6g (0.02 mol) of PETA and 1.2g (0.02 mol) of glycol for end capping, setting the temperature to be 65 ℃, continuously stirring for 4 hours to obtain a component 1, wherein 0.02mol of hydroxyl groups are left in the component 1;
(2) 18.5g (0.02 mol) of a trimer of HDI and 2 drops of catalyst DBTDL were charged into a dry four-necked flask equipped with a stirrer, a condenser, a nitrogen conduit and a constant pressure titration funnel and warmed to 65 ℃; slowly dripping the component 1 prepared in the step (1) into the four-neck flask, and reacting for 2 hours at 65 ℃;
(3) 36g (0.018 mol) of HTPB is added into the four-neck flask to react at 65 ℃ (during which the viscosity is adjusted by using a proper solvent) for 2h, and then 1.2g (0.004 mol) of PETA is added to carry out end-capping treatment to obtain the designed six-claw high-elasticity-hand-feeling wear-resistant multi-arm type photocuring resin.
Example 1 the hard segment prepared (i.e., the trimer reactant of IPDI and HDI) accounted for 26.7% of the total elastomeric abrasion resistant resin mass.
Example 2
When the hard segment content is 38.6%, the reactants are: IPDI mass 10g, HDT (trimer of HDI) 28.6g, when PCDL (set to x) + HTPB (set to y) =61.4g, x/800 + y/2000 =0.1015, 0.1015 is determined by the total moles of IPDI and HDT. Other reaction conditions and parameters were the same as in example 1.
Example 3
When the hard segment content is 42.6%, the reactants are: IPDI mass 12.6g, HDT 30g, when PCDL (set to x) + HTPB (set to y) =57.4g, x/800 + y/2000 =0.1161, 0.1161 is determined by the total moles of IPDI and HDT. Other reaction conditions and parameters were the same as in example 1.
Example 4
When the hard segment content is 46.6%, the reactants are: IPDI mass 14.6g, HDT 32g, when PCDL (set to x) + HTPB (set to y) =53.4g, x/800 + y/2000 =0.1290, 0.1290 is determined by the total moles IPDI and HDT. Other reaction conditions and parameters were the same as in example 1.
Example 5
When the hard segment content is 50.6%, the reactants are: IPDI mass 20g, HDT 30.6g, when PCDL (set to x) + HTPB (set to y) =49.4g, x/800 + y/2000 =0.1263, 0.1263 is determined by the total moles of IPDI and HDT. Other reaction conditions and parameters were the same as in example 1.
The influence of the hard segment content on the mechanical properties of the elastic abrasion-resistant resin prepared in examples 2 to 5 is shown in fig. 1.
As can be seen from FIG. 1, when the hard segment content was increased from 38.6% to 50.6%, the tensile strength of the PU elastomer was increased from 4.68MPa to 20.83MPa, and the elongation at break was increased from 248.32% to 445.31% and then decreased to 207.38%. The phenomenon is mainly caused by the fact that the distribution of the hard segment in the soft segment phase is increased due to the increase of the content of the hard segment, the hardness is increased, meanwhile, due to the fact that the hard segment island region plays a role in physical crosslinking in the elastomer, the increase of the crosslinking points can also promote the formation of hydrogen bonds or crosslinking among the hard segments, the tensile strength of the PU elastomer is continuously increased, and the elongation at break is greatly changed.
Claims (9)
1. A preparation method of high-elasticity hand-feeling wear-resistant multi-arm photocuring resin is characterized by comprising the following steps:
(1) adding diisocyanate and dihydric alcohol into a reaction container, dropwise adding a catalyst diluted by ethyl acetate, and heating for reaction; adding pentaerythritol triacrylate PETA and glycol for end capping, and keeping the temperature and stirring continuously to obtain a component 1;
(2) adding trifunctional isocyanate and a catalyst into a reaction container, heating for reaction, slowly dripping the component 1 prepared in the step (1) into the reaction container, and continuing to perform heat preservation reaction;
(3) and (3) adding hydroxyl-terminated polybutadiene HTPB into the reaction container in the step (2) for continuous reaction, and adding pentaerythritol triacrylate for end-capping treatment to obtain the high-elasticity hand-feeling wear-resistant multi-arm photocuring resin.
2. The preparation method of the high-elasticity wear-resistant multi-arm photocuring resin as claimed in claim 1, wherein the preparation method comprises the following steps: the trifunctional isocyanate is specifically a trimer of HDI.
3. The preparation method of the high-elasticity wear-resistant multi-arm photocuring resin as claimed in claim 1, wherein the preparation method comprises the following steps: the catalyst is specifically one of dibutyltin dilaurate DBTDL, an organic bismuth catalyst, dimethylcyclohexylamine or methyldiethylenetriamine.
4. The preparation method of the high-elasticity wear-resistant multi-arm photocuring resin as claimed in claim 1, wherein the preparation method comprises the following steps: the diisocyanate in the step (1) is specifically isophorone diisocyanate (IPDI) or Toluene Diisocyanate (TDI);
the dihydric alcohol is polycarbonate dihydric alcohol PCDL or polytetrahydrofuran PTMG.
5. The preparation method of the high-elasticity-handfeel wear-resistant multi-arm type photocuring resin according to claim 1, wherein the step (1) is specifically as follows: adding 8-25g of diisocyanate and 13-50g of dihydric alcohol into a dry four-neck flask connected with a stirrer, a condenser pipe, a nitrogen conduit and a constant pressure titration funnel; continuously adding 1-3 drops of catalyst diluted by 15-20mL of ethyl acetate, heating to 60-70 ℃, and continuously reacting for 2-3h after the temperature is reached; adding 6-30g of pentaerythritol triacrylate PETA and 1-5g of glycol for end capping, keeping the temperature at 60-70 ℃, and continuously stirring for 4-5h to obtain the component 1.
6. The preparation method of the high-elasticity-handfeel wear-resistant multi-arm type photocuring resin according to claim 1, wherein the step (2) is specifically as follows: adding 10-35g of trifunctional isocyanate and 1-2 drops of catalyst into a dry four-neck flask connected with a stirrer, a condenser pipe, a nitrogen conduit and a constant pressure titration funnel, and heating to 60-70 ℃; slowly dropping the component 1 prepared in the step (1) into the four-neck flask, and reacting for 2-3h at 60-70 ℃.
7. The preparation method of the high-elasticity-handfeel wear-resistant multi-arm type photocuring resin as claimed in claim 1, wherein the step (3) is specifically as follows: adding 30-55g of hydroxyl-terminated polybutadiene HTPB into the four-neck flask obtained in the step (2), continuing to react for 2-3h at 60-70 ℃, and adding 1-5g of pentaerythritol triacrylate for end-capping treatment; obtaining the multi-arm photocureable resin with high elasticity and wear resistance.
8. The preparation method of the multi-arm photocuring resin with high elastic hand feeling and wear resistance according to claim 7, wherein the preparation method comprises the following steps: and (3) adding a solvent in the reaction process to adjust the viscosity, so that the polymer does not have a pole climbing phenomenon in the reaction.
9. The preparation method of the multi-arm photocuring resin with high elastic hand feeling and wear resistance as claimed in claim 8, wherein the preparation method comprises the following steps: the solvent is tetrahydrofuran THF, acetone ACE or dimethylformamide DMF.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114318630A (en) * | 2021-12-31 | 2022-04-12 | 广东新蓝天纺织新材料科技有限公司 | Elastic woven fabric containing curable resin and preparation method thereof |
| CN115612395A (en) * | 2022-11-07 | 2023-01-17 | 江南大学 | Preparation process of quick-drying fluorine-containing modified UV (ultraviolet) curing hyperbranched waterborne polyurethane coating |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114318630A (en) * | 2021-12-31 | 2022-04-12 | 广东新蓝天纺织新材料科技有限公司 | Elastic woven fabric containing curable resin and preparation method thereof |
| CN115612395A (en) * | 2022-11-07 | 2023-01-17 | 江南大学 | Preparation process of quick-drying fluorine-containing modified UV (ultraviolet) curing hyperbranched waterborne polyurethane coating |
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