IES87293Y1 - Ultra-high hardness and high temperature-resistant casting polyurethane elastomer and preparation method thereof - Google Patents

Ultra-high hardness and high temperature-resistant casting polyurethane elastomer and preparation method thereof Download PDF

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IES87293Y1
IES87293Y1 IE20200257U IE20200257U IES87293Y1 IE S87293 Y1 IES87293 Y1 IE S87293Y1 IE 20200257 U IE20200257 U IE 20200257U IE 20200257 U IE20200257 U IE 20200257U IE S87293 Y1 IES87293 Y1 IE S87293Y1
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polyurethane elastomer
diisocyanate
ultra
high temperature
aliphatic
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IE20200257U
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IE20200257U1 (en
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Wenbin Qi
Chaoyang Zhao
Chaosuo Liu
Xiangjuan Jin
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Shanghai Hecheng Polymer Tech Co Ltd
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    • 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
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
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    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
    • C08G18/3814—Polyamines
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    • C08G18/30—Low-molecular-weight compounds
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    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
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    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—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
    • 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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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—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
    • C08G18/757—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 at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
    • C08G18/765—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
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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
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
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    • 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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    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
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  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
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Abstract

The present invention relates to an ultra-high hardness high temperature-resistant casting polyurethane elastomer and a preparation method thereof, wherein the components mainly include an aliphatic isocyanate prepolymer and an aromatic amine chain extender. The product of the present invention has a Shore hardness of 80-85D, transparent appearance, good resilience, good tensile strength and tear strength, good weather resistance, ultraviolet resistance and oxidation resistance; it further maintains a Shore hardness of at least 80D at 180°C.

Description

ULTRA-HIGH HARDNESS AND HIGH TEMPERATURE-RESISTANT CASTING POLYURETHANE ELASTOMER AND PREPARATION METHOD THEREOF FIELD OF INVENTION
[001] a method for preparing an ultra-high hardness and high temperature-resistant casting The present invention belongs to the field of polyurethane elastomers, and relates to polyurethane elastomer.
BACKGROUND TO INVENTION
[002] because its wide variety of raw materials, different processing means, different proportion of Casting polyurethane elastomer material is an emerging macromolecule material, and soft and hard segments in the elastomer composition, different phase arrangement between molecular structures, etc., it can have an ultra-wide hardness range from Shore A 0 degree to Shore D 85 degree and various physical properties, such as very good wear resistance, oil resistance, and high tensile and tear resistance, or high elongation, etc. In general, the hardness of the casting polyurethane elastomer material can be typically below 70 D, and when the ambient temperature reaches above 100°C, the hardness drops sharply, and higher hardness and strength cannot be maintained. This also greatly limits the use of polyurethane elastomer materials in some fields.
[003] polyurethane elastomer are as follows: in terms of polyols, selecting those with smaller The conventional methods for improving the heat resistance of the casting molecular weight, or containing benzene rings or ester rings and other cyclic structures to improve the heat resistance of the soft segment phase; in terms of isocyanates, selecting single benzene ring isocyanates or tightly structured aromatic ring isocyanates; and in terms of chain agents, also selecting amine or alcohol chain extenders with benzene rings. Such solutions are mainly to add a cyclic structure to the main chain of the elastomer molecule to increase the steric hindrance of the movement of the elastomer molecule, thereby hindering the relative movement of the molecule brought about by the heating. In such a manner that the cyclic structure is distributed on the main chain, the heat resistance of the elastomer material can be met to a certain extent, but the intermolecular acting force of the elastomer main chain becomes weak and displacement easily occurs when exposed to a higher temperature, for example, more than 140°C. As a result, the elastomer exhibits a sharp decrease in hardness when exposed to high heat.
SUMMARY OF INVENTION [O04] hardness high temperature-resistant casting polyurethane elastomer and a preparation The technical problem to be solved by the present invention is to provide an ultra-high method thereof, wherein the polyurethane elastomer still maintains hardness of more than Shore 80 D at high temperature of 180°C.
[005] casting polyurethane elastomer consisting of the following components in percentage by The present invention provides an ultra-high hardness high temperature-resistant mass: aliphatic isocyanate prepolymer HC-100 50-59%; aromatic amine chain extender 40-45%; antioxidant 0.1-1%; ultraviolet (UV) absorber 0.1 -1 %; hydrolysis stabilizer 0.1-1%; storage stabilizer 0.1-1%; defoamer 0. 1-1%.
[006] The raw materials of the aliphatic isocyanate prepolymer HC-100 comprise 30-40% of polyether polyol and 60-70% of aliphatic diisocyanate.
[007] The polyether polyol has a molecular weight of 300-4000, a functionality of 2-4 and is selected from one or more of GE-204, RA-640, NT-403A, DV-125, MN-500, MN-700, MN- 1000, MN-1500, MN-3050D and GE-303; the aliphatic diisocyanate is 1,6-hexamethylene diisocyanate (HDI), HDI trimer, HDI biuret, 3-isocyanatomethylene-3, 5, 5-trimethylcyclohexyl isocyanate (IPDI), 4, 4'-dicyclohexylmethane diisocyanate (HMDI), m-xylylene diisocyanate (XDI) , hydrogenated xylylene diisocyanate (HXDI), a mixture of 2, 2, 4-and 2, 4, 4-trimethyl- 1, 6-hexamethylene diisocyanate (TMHMDI), tetramethyl m-xylylene diisocyanate (m-TMXDI), and norbornane diisocyanate (NBDI).
[008] chloroaniline) (MOCA), 3, 5-dimethylthiotoluenediamine (DMTDA), 3, 5-diethyltoluenediamine (DETDA), 4, 4'-methylene bis (3-chloro-2, 6-diethylaniline) (MCDEA), and 4, 4'-methylene bis (2, 6-diethyl) aniline (MDEA).
[009] tetra- [methylene(3,5-di-tert-butylhydroxy-hydrocinnamate)]methane 1010, and tris (2, 4-di-tert- The aromatic amine chain extender is at least one of 4,4’-methylene bis(2- The antioxidant is at least one of butylated hydroxytoluene (BHT), butylphenyl) phosphite.
[0010] The UV absorber is at least one of ethyl 4-[[(methylphenylamino) methylene] amino] benzoate (tinuvin 101), 2-(2'-hydroxy-3', 5'-di-tert-butylphenyl)chlorobenzotriazole (UV- 327), and 2-hydroxyn-octyloxybenzophenone (UV-531). [001 1] The hydrolysis stabilizer is at least one of 2, 2', 6, 6'-tetraisopropyldiphenylcarbodiimide (stabaxol I), and polycarbodiimide (staboxol P).
[0012] The storage stabilizer is at least one of phosphoric acid and benzoyl chloride.
[0013] The defoamer is at least one of BYK 052, BYK 053, BYK 056 and BYK A560.
[0014] The present invention also provides a method for preparing the ultra-high hardness and high temperature-resistant casting polyurethane elastomer, comprising: (1) synthesizing an aliphatic isocyanate prepolymer HC-100 based on a ratio of 30- 40% of polyether polyol and 60-70% of aliphatic diisocyanate at 70-90°C for 3-6 hours; (2) weighing the aliphatic isocyanate prepolymer based on the formula, heating to 90- 110°C and vacuuming for 20-30 minutes under a vacuum degree of -0.1 MPa; (3) reducing the temperature to 68-72°C, adding the antioxidant, the UV absorber, the hydrolysis stabilizer, the storage stabilizer and the defoamer in the formula, uniformly stirring for 10-20 minutes, and vacuuming for 10-20 minutes under the vacuum degree of -0.1 MPa again; (4) adding the aromatic amine chain extender into the mixture in step (2), uniformly stirring, vacuuming again for 1-2 minutes, pouring into a mold coated with a release agent in advance, putting into a blowing oven of 100-105°C, vulcanizing for 30-40 minutes, and demolding; and (5) after demolding, continuing vulcanizing the product in the oven of 100-105°C for 22-24 hours to obtain the ultra-high hardness and high temperature-resistant casting polyurethane elastomer.
[0015] The main principle of the present invention is that
[0016] an aliphatic isocyanate prepolymer with high functionality is used, an annular structure contained by a chain extender is added on a molecular main chain forming a network structure, so that a large number of three-dimensional network penetrating structures are formed on the whole elastomer molecular chain, greatly increasing the molecular weight and the branching degree of an elastomer material, and it appears that the elastomer has ultra-high hardness; meanwhile, the acting forces among the molecules of the elastomer material are increased, preventing the displacement of most molecules by the steric effect when the elastomer material is exposed to high temperature, and it appears that the elastomer can maintain the hardness at high temperatures.
[0017] Advantageous Effects
[0018] The product of the present invention has a Shore hardness of 80-85D, transparent appearance, good resilience, good tensile strength and tear strength, good weather resistance, ultraviolet resistance, oxidation resistance and other performances; and it still maintain a Shore hardness of more than 80D at a high temperature of 180°C, it has a good market application prospect.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
[0019] The present invention is further illustrated below with reference to detailed descriptions. It should be understood that these examples are merely illustrative of the present invention and are not intended to limit the scope of the present invention. In addition, it will be understood that various changes and modifications may be made by those skilled in the art in light of the teachings of the present invention, and equivalents may be resorted to, falling within the scope of the appended claims.
[0020] EXAMPLE 1 consists of the following components in percentage by mass: Material Brand or Proportion Manufacturer Names Composition (%) Aliphatic isocyanate HC-100 57 (NT-403A, Gaoqiao prepolymer Petrochemical, 33.4%: HDI.
Degussa, 66.6%) Aromatic amine chain MOCA 42 Suzhou Xiangyuan extender Antioxidant BHT 0.2 Taiwan double bond UV absorber UV-327 0.2 Taiwan double bond
[0021] EXAMPLE 2 consists of the following components in percentage by mass: Material Names Brand or Proportion Manufacturer Composition (%) Aliphatic HC-100 55.6 (NT-403A, Gaoqiao Petrochemical, isocyanate 33.4%: HDI, Degussa, 66.6%) prepolymer Aromatic amine MOCA 43.4 Suzhou Xiangyuan chain extender Antioxidant BHT 0.1 Taiwan double bond UV absorber UV-327 0.1 Taiwan double bond Hydrolysis stabaxol I 0.3 Taiwan double bond stabilizer Storage stabilizer benzoyl chloride 0.3 Taiwan double bond Defoamer A-560 0.2 BYK chemical
[0022] The method specifically comprises the following steps: (1) synthesizing an aliphatic isocyanate prepolymer HC-100 based on a ratio of NT-403A= 33.4% and HDI =66.6% at 70-90°C for 3-6 hours; (2) weighing the aliphatic isocyanate prepolymer based on the formula, heating to 100°C and vacuuming for 25 minutes under a vacuum degree of -0.1 MPa; (3) reducing the temperature to 70°C, adding the antioxidant, the UV absorber, the hydrolysis stabilizer, the storage stabilizer and the defoamer in the formula, uniformly stirring for 15-20 minutes, and vacuuming for 15 minutes under the vacuum degree of -0.1 MPa again; (4) adding the aromatic amine chain extender into the mixture in step (2), uniformly stirring, vacuuming again for 2 minutes, pouring into a mold coated with a release agent in advance, putting into a blowing oven of 105°C, vulcanizing for 30 minutes, and demolding; and (5) after demolding, continuing vulcanizing the product in the oven of 105°C for 24 hours to obtain the ultra-high hardness and high temperature-resistant casting polyurethane elastomer.
[0023] The properties of the polyurethane elastomer obtained by the above process are shown in the following table: Test Items Units Test criteria EXAMPLE 1 EXAMPLE 2 Finished 23°C - Yellowish Yellowish product transparent transparent appearance elastomer elastomer Hardness of Shore D GB/T 531 .1- 83 85 finished product 2008 @23°C Hardness of Shore D GB/T 531.1- 80 82.5 finished product 2008 @180°C Finished g/cm3 25°C GB/T 533-2008 1.27 1.27 product density Tear tensile MPa GB/T 528-2009 120 118 strength Elongation at % GB/T 528-2009 55 51 break Rebound of % GB/T 1681- 53 55 impact 2009

Claims (5)

1. An ultra-high hardness high temperature-resistant casting polyurethane elastomer, characterized by consisting of the following components in percentage by mass: aliphatic isocyanate prepolymer HC-100 50 -59%; aromatic amine chain extender 40-45%; antioxidant 0.1-1 %; Ultraviolet (UV) absorber 0.1-1%; hydrolysis stabilizer 0.1-1%; storage stabilizer 0.1-1%; defoamer 0. 1-1%.
2. The polyurethane elastomer of claim 1, characterized in that: the raw materials of the aliphatic isocyanate prepolymer HC-100 comprise 30-40% of polyether polyol and 60-70% of aliphatic diisocyanate;the polyurethane elastomer of claim 2, characterized in that: the polyether polyol has a molecular weight of 300-4000, a functionality of 2-4 and is selected from one or more of GE-204, RA-640, NT-403A, DV-125, MN-500, MN-700, MN-1000, MN- 1500, MN-3050D and GE-303; the aliphatic diisocyanate is at least one of 1 ,6-hexamethylene diisocyanate (HDI), HDI trimer, HDI biuret, 3-isocyanatomethylene-3, 5, 5-trimethylcyclohexyl isocyanate (IPDI), 4, 4'-dicyclohexylmethane diisocyanate (HMDI), m-xylylene diisocyanate (XDI), hydrogenated xylylene diisocyanate (HXDI), a mixture of 2, 2, 4-and 2, 4, 4-trimethyl-1, 6-hexamethylene diisocyanate (TMHMDI), tetramethyl m-xylylene diisocyanate (m-TMXDI), and norbornane diisocyanate (NBDI).
3. The polyurethane elastomer of claim 1, characterized in that: the aromatic amine chain 3,3’-dichloro-4,4’-diaminodiphenylmethane (MOCA), 3, 5- dimethylthiotoluenediamine (DMTDA), 3, 5-diethyltoluenediamine (DETDA), 4, 4'-methylene bis (3-chloro-2, 6-diethylaniline) (MCDEA), and 4, 4'-methylene bis (2, 6-diethyl) aniline (MDEA);the antioxidant is at least one of 2, 6-di-tert-butylmethylphenol (BHT), tetra- [methylene(3,5-di-tert-butylhydroxy-hydrocinnamate)]methane 1010, and tris (2, 4-di-tert- extender is butylphenyl) phosphite; the UV absorber is at least one of ethyl 4-[[(methylphenylamino) methylene] amino] benzoate, 2-(2'-hydroxy-3', 5'-di-tert-butylphenyl)chlorobenzotriazole, and 2-hydroxyn-octyloxybenzophenone. p.6 20
4. The polyurethane elastomer of claim 1, characterized in that: the hydrolysis stabilizer is at least one of 2, 2', 6, 6'-tetraisopropyldiphenylcarbodiimide, and polycarbodiimide; the storage stabilizer is at least one of phosphoric acid and benzoyl chloride; the defoamer is at least one of BYK 052, BYK 053, BYK 056 and BYK A560.
5. A method for preparing the ultra-high hardness and high temperature-resistant casting polyurethane elastomer of claim 1, comprising: (1) synthesizing an aliphatic isocyanate prepolymer HC-100 based on a ratio of 30-40% of polyether polyol and 60-70% of aliphatic diisocyanate at 70-90°C for 3-6 hours; (2) weighing the aliphatic isocyanate prepolymer based on the formula, heating to 90-110°C and vacuuming for 20-30 minutes under a vacuum degree of -0.1 MPa; (3) reducing the temperature to 68-72°C, adding the antioxidant, the UV absorber, the hydrolysis stabilizer, the storage stabilizer and the defoamer in the formula, uniformly stirring for 10-20 minutes, and vacuuming for 10-20 minutes under the vacuum degree of- 0.1 MPa again; (4) adding the aromatic amine chain extender into the mixture in step (2), uniformly stirring, vacuuming again for 1-2 minutes, pouring into a mold coated with a release agent in advance, putting into a blowing oven of 100-105°C, vulcanizing for 30-40 minutes, and demolding; and (5) after demolding, continuing vulcanizing the product in the oven of 100-105°C for 22-24 hours to obtain the ultra-high hardness and high temperature-resistant casting polyurethane elastomer. p.7
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