CN109880347A - Polyurethane materials - Google Patents
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- CN109880347A CN109880347A CN201910169989.1A CN201910169989A CN109880347A CN 109880347 A CN109880347 A CN 109880347A CN 201910169989 A CN201910169989 A CN 201910169989A CN 109880347 A CN109880347 A CN 109880347A
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Abstract
A kind of polyurethane materials include Polyurethane and yellowing-resistant component.The yellowing-resistant component includes a kind of compound with formula (I) structure,In formula (I), R1And R2Each independently represent C1To C24Alkyl or C6To C12Aryl, Y1、Y2And Y3Hydrogen or methyl are each independently represented, n indicates 1 to 7 integer.The polyurethane materials are by the compound with formula (I) structure, to have excellent yellowing-resistant ability.
Description
Technical field
The present invention is to be related to a kind of constituent of high-molecular compound, more particularly to a kind of polyurethane materials.
Background technique
In the production and process of Polyurethane product, since the molecular structure of Polyurethane is so need higher operation
Temperature causes Polyurethane to be exposed under the hot environment full of heat source and exhaust gas and xanthochromia occurs.For solve Polyurethane product because
Xanthochromia problem caused by thermo-oxidative ageing (thermal oxidative aging), can generally add such as 3 in Polyurethane,
The sulfur antioxidant of 3'- dilauryl thiodipropionate etc., alternatively, such as antioxidant 245, antioxidant 1790 by
The problem of hindering phenolic antioxidant, Polyurethane product xanthochromia improved by oxidation resistant mechanism.
In addition, during the use of Polyurethane product or storage, it also can be yellow due to touching the nitrogen oxides in air
Become, therefore the anti-yellowing agent such as HN-150, HN-130 can generally be added in Polyurethane, Lai Gaishan Polyurethane product is because connecing
Touching nitrogen oxides, there is a phenomenon where xanthochromias.
However, requirement of the consumer for the quality of Polyurethane product more becomes strictly, and empty dirt is got worse, in air
The concentration of nitrogen oxides only increases and the xanthochromia degree of Polyurethane product will certainly be made to aggravate, and also causes above-mentioned sulphur system anti-
Oxidant, hindered phenolic antioxidant and anti-yellowing agent are not applied and are used, therefore, it is necessary to develop yellowing-resistant ability more preferably
Polyurethane materials.
Summary of the invention
The purpose of the present invention is to provide a kind of preferable polyurethane materials of yellowing-resistant ability.
Polyurethane materials of the present invention include:
Polyurethane；And
Yellowing-resistant component has the compound of formula (I) structure including one kind,
In formula (I), R1And R2Each independently represent C1To C24Alkyl or C6To C12Aryl, Y1、Y2And Y3Respectively solely
On the spot indicate that hydrogen or methyl, n indicate 1 to 7 integer.
Polyurethane materials of the present invention, in the formula (I), the R1And R2Each independently represent C1To C24Alkyl.
Polyurethane materials of the present invention, in the formula (I), the R1And R2Each independently represent C10To C24Alkyl.
Polyurethane materials of the present invention, in the formula (I), n indicates 1 to 4 integer.
Polyurethane materials of the present invention, the compound with formula (I) structure are to be selected from chemical combination shown in formula (I-1)
Object, formula (I-2) compound represented, formula (I-3) compound represented or above-mentioned any combination.
Polyurethane materials of the present invention, with the total amount of the Polyurethane for 100 parts by weight, the change with formula (I) structure
The amount ranges for closing object are 0.01 to 3 parts by weight.
Polyurethane materials of the present invention, the yellowing-resistant component further include hindered phenolic antioxidant and hydrazides system anti-yellowing agent
At least one of.
Polyurethane materials of the present invention, the hindered phenolic antioxidant are selected from (the 3- third fourth of triethylene glycol ether-two
Base -4- hydroxy-5-methyl base phenyl) propionic ester, 1,3,5- trimethyl -2,4,6- three (bis- third butyl -4- hydroxybenzyl of 3,5-)
Benzene, 1,3,5- tri- (bis- third butyl -4- hydroxybenzyl of 3,5-) chlorinated isocyanurates, three (4- third butyl -3- hydroxyl -2,6- two
Methylbenzyl) isocyanuric acid ester or above-mentioned any combination.
Polyurethane materials of the present invention, hydrazides system anti-yellowing agent are selected from 1,6- hexamethylene bis (N, N- dimethyl
Semicarbazides), 1,1,1', 1'- tetramethyl -4,4'(methylene-two-is to phenylene) double semicarbazides or above-mentioned any combination.
The beneficial effects of the present invention are: the polyurethane materials have the compound of formula (I) structure described in, thus
Has excellent yellowing-resistant ability.
Specific embodiment
The content of present invention is described in detail below:
Polyurethane materials of the present invention include Polyurethane and yellowing-resistant component.The yellowing-resistant component includes a kind of with formula
(I) compound of structure can make the polyurethane materials have excellent yellowing-resistant ability.Preferably, of the invention one
In a little state sample implementations, the yellowing-resistant component further includes at least one of hindered phenolic antioxidant and hydrazides system anti-yellowing agent,
It can make the polyurethane materials that there is more preferably yellowing-resistant ability.
In this article, described " Polyurethane (polyurethane) " refers to and contains amido formate in main chain
(carbamate) high-molecular compound of monomeric unit.In polyurethane materials of the present invention, used Polyurethane is not special
Limitation, specific type and property that can flexibly according to the product demand selection Polyurethane of the practical application of polyurethane materials.
The compound with formula (I) structure be it is as follows,
In formula (I), R1And R2Each independently represent C1To C24Alkyl or C6To C12Aryl, Y1、Y2And Y3Respectively solely
On the spot indicate that hydrogen or methyl, n indicate 1 to 7 integer.
In some state sample implementations of the invention, the R1And R2Each independently represent C1To C24Alkyl；Preferably,
The R1And R2Each independently represent C10To C24Alkyl.
In some state sample implementations of the invention, n indicates 1 to 4 integer.
In some concrete examples of the invention, the compound with formula (I) structure is selected from shown in formula (I-1)
Compound, formula (I-2) compound represented, formula (I-3) compound represented or above-mentioned any combination.
The source of the compound with formula (I) structure can be commercial product or voluntarily synthesize.It is described that there is formula (I)
The synthesis mode of the compound of structure is such as, but not limited to, by formula (A) compound represented and formula (B) compound represented one
Esterification is carried out in the presence of catalyst.
In formula (A) and formula (B), X indicates R1Or R2, Z expression Y1Or Y3, wherein R1、R2、Y1、Y2、Y3And the definition of n be as
It is upper described, it is repeated no more in this.
The concrete example of formula (A) is such as, but not limited to 3- (dodecyl is thio) propionic acid [3- (dodecylthio)
Propanoic acid], 3- (dodecyl is thio) -2 Methylpropionic acid [3- (dodecylthio) -2-methylpropanoic
Acid], 3- (decyl is thio) propionic acid [3- (decylthio) propanoic acid] etc..
The concrete example of formula (B) is such as, but not limited to triethylene glycol (triethylene glycol), 2- [2- (2- propoxyl)
Propoxyl group] -1- propyl alcohol { 2- [2- (2-hydroxypropoxy) propoxy] -1-propanol }, diethylene glycol (DEG) (diethylene
Glycol) etc..
In some concrete examples of the invention, formula (I-1) compound represented is by 3- (dodecyl is thio) propionic acid and three
Glycol carries out obtained by esterification；Formula (I-2) compound represented is by 3- (dodecyl is thio) -2 Methylpropionic acid and 2-
[2- (2- propoxyl) propoxyl group] -1- propyl alcohol carries out obtained by esterification；Formula (I-3) compound represented is by the 3- (last of the ten Heavenly stems
Base is thio) propionic acid and diethylene glycol (DEG) carry out obtained by esterification.
The type and dosage of the catalyst are not particularly limited, and the general common catalyst of esterification is all suitable for this.
The temperature and pressure of the esterification are not particularly limited, the temperature model of the such as, but not limited to described esterification
Enclose is 50 to 180 DEG C.
With the total amount of the Polyurethane for 100 parts by weight, the amount ranges of the compound with formula (I) structure are
0.01 to 3 parts by weight.
The hindered phenol anti-oxidants are such as, but not limited to: (the 3- third butyl -4- hydroxy-5-methyl of triethylene glycol ether-two
Base phenyl) propionic ester [triethylene glycol bis (3-tert-butyl-4-hydroxy-5-methylphenyl)
Propionate, CAS No.36443-68-2, abbreviation antioxidant 245), 1,3,5- trimethyls -2,4,6- tri- (3,5- 2
Tributyl -4- hydroxybenzyl) benzene [1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-
Hydroxybenzyl) benzene, CAS No.1709-70-2, abbreviation antioxidant 1330], 1,3,5- tri- (3,5- bis- thirds
Butyl -4- hydroxybenzyl) chlorinated isocyanurates [1,3,5-tri (3,5-di-tert-butyl-4-hydroxybenzyl)
Isocyanurate, CAS No.27676-62-6, abbreviation antioxidant 3114], three (4- third butyl -3- hydroxyls -2,6- bis-
Methylbenzyl) isocyanuric acid ester [tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)
Isocyanurate, CAS No.40601-76-1, abbreviation antioxidant 1790), above-mentioned hindered phenol anti-oxidants can independent one
Kind mixes a variety of uses.In a specific example of the present invention, the hindered phenol anti-oxidants are selected from triethylene glycol ether-
Two (3- third butyl -4- hydroxy-5-methyl base phenyl) propionic esters.
With the total amount of the Polyurethane for 100 parts by weight, the amount ranges of the hindered phenol anti-oxidants are 0.01 to 1
Parts by weight.
Hydrazides system anti-yellowing agent is such as, but not limited to 1,6- hexamethylene bis (N, N- dimethylamino urea) [1,6-
Hexamethylene bis (N, N-dimethylsemicarbazide), CAS No.69938-76-7, abbreviation anti-yellowing agent
HN-130), 1,1,1', 1'- tetramethyl -4,4'(methylene-two-is to phenylene) double semicarbazides [1,1,1', 1'-
Tetramethyl-4,4'- (methylene-di-p-phenylene) disemicarbazide, CAS No.85095-61-0,
Abbreviation anti-yellowing agent HN-150), above-mentioned hydrazides system anti-yellowing agent can the individually a kind of or a variety of uses of mixing.In a tool of the invention
In body example, hydrazides system anti-yellowing agent is selected from 1,1,1', 1'- tetramethyl -4,4'(methylene-two-to phenylene) it is double
Semicarbazides.
With the total amount of the Polyurethane for 100 parts by weight, the amount ranges of hydrazides system anti-yellowing agent are 0.01 to 1 weight
Measure part.
In some concrete examples of the invention, the yellowing-resistant component includes the compound with formula (I) structure；?
In other concrete examples of the invention, the yellowing-resistant component includes the compound with formula (I) structure and described is obstructed
Phenolic antioxidant；In other concrete example of the invention, yellowing-resistant component includes the chemical combination with formula (I) structure
Object, the hindered phenolic antioxidant and hydrazides system anti-yellowing agent.
The present invention will be described further with regard to following embodiment, however, it should be noted that the embodiment is only to illustrate,
And it is not necessarily to be construed as the limitation that the present invention is implemented.
[chemicals and equipment]
1. Polyurethane: specific type is heat plasticity polyurethane (thermoplastic polyurethanes).Manufacturer's model
For the S-195 of SK company, South Korea.Abbreviation PU in following table 1.
2. hindered phenolic antioxidant: specific type is (the 3- third butyl -4- hydroxy-5-methyl base benzene of triethylene glycol ether-two
Base) propionic ester (antioxidant 245).245 are referred to as in following table 1.
3. hydrazides system anti-yellowing agent: specific type is 1,1,1', and 1'- tetramethyl -4,4'(methylene-two-is to phenylene)
Double semicarbazides (anti-yellowing agent HN-150).150 are referred to as in following table 1.
4. the compound with formula (I) structure: being specially formula (I-1) compound represented, formula (I-2) compound represented
And formula (I-3) compound represented.I-1, I-2 and I-3 are briefly referred to as in following table 1.
5.3,3'- dilauryl thiodipropionates: it is used for the antioxidant of Polyurethane for the prior art, is commonly called as " anti-oxidant
Agent DLTP ".DL is referred to as in following table 1.
[preparation example 1] formula (I-1) compound represented
An agitating device and a H-type pipework condensation reflux unit are set up on a three neck reaction kettles.By 55.6 grams
It is anti-that three neck is added in 3- (dodecyl is thio) propionic acid, 15 grams of triethylene glycol, 500 grams of toluene and 1 gram of p-methyl benzenesulfonic acid
It answers in kettle, is warming up to 110 to 120 DEG C of reflux temperature, it is anti-when no moisture generates at the reflux temperature sustained response 6 hours
It should terminate.Then, white solid can be precipitated by being gradually cooled to -4 DEG C, after the white solid is collected by filtration, be rinsed with ice heptane
The white solid, then the white solid is placed in a vacuum drying oven and stands 2 hours at 35 DEG C, it obtains 60.4 grams and is
Formula (I-1) compound represented of white solid.
[preparation example 2] formula (I-2) compound represented
An agitating device and a H-type pipework condensation reflux unit are set up on a three neck reaction kettles.By 58 grams of 3-
(dodecyl is thio) -2 Methylpropionic acid, 19.5 grams of 2- [2- (2- propoxyl) propoxyl group] -1- propyl alcohol, 500 grams of toluene
And 1 gram of p-methyl benzenesulfonic acid is added in the three necks reaction kettle, 110 to 120 DEG C of reflux temperature is warming up to, in the reflux temperature
7 hours of sustained response, reaction terminates when no moisture generates.Then, 100 DEG C are gradually warming up to using a vacuum equipment
Afterwards, reaction dissolvent and by-product are extracted, obtains 63.5 grams and is formula (I-2) compound represented of yellowish colloid.
[preparation example 3] formula (I-3) compound represented
An agitating device and a H-type pipework condensation reflux unit are set up on a three neck reaction kettles.By 50.2 grams
The three necks reaction is added in 3- (decyl is thio) propionic acid, 10.1 grams of diethylene glycol (DEG), 500 grams of toluene and 1 gram of p-methyl benzenesulfonic acid
In kettle, 110 to 120 DEG C of reflux temperature are warming up to, it is anti-when no moisture generates in 6 hours of the reflux temperature sustained response
It should terminate.Then, white solid can be precipitated by being gradually cooled to -4 DEG C, after the white solid is collected by filtration, be rinsed with ice heptane
The white solid, then the white solid is placed in a vacuum drying oven and stands 2 hours at 35 DEG C, it obtains 49.2 grams and is
Formula (I-3) compound represented of white solid.
[embodiment 1]
According to ingredient and dosage (parts by weight) shown in table 1, yellowing-resistant component and the Polyurethane of 100 parts by weight are uniformly mixed
Conjunction obtains a mixture.Using a twin-screw extruder, (process temperatures are set as 190 to 200 DEG C, and screw speed is set as
200 revs/min, charging rate is set as 12 revs/min) mixture described in extrusion is mixed, obtain an extrusion object.Then, will
The extrusion object is 3 hours dry at 80 DEG C, obtains the polyurethane materials of embodiment 1.
[embodiment 2 to 9 and comparative example 1 to 6]
Composition and dosage in addition to changing yellowing-resistant component shown in foundation table 1, embodiment 2 to 9 and comparative example 1 to 6 gather
Amine ester material is prepared using manufacturing method identical as embodiment 1.
[properties evaluations]
It (projects temperature using an ejaculator and is set as 200 DEG C, injection pressure is set as 120bar), by embodiment 1 to 9
And testing piece is respectively prepared in the polyurethane materials of comparative example 1 to 6.Measure the testing piece of embodiment 1 to 9 and comparative example 1 to 6 with
The yellowness index difference (Yellowness difference, △ YI) of lower three kinds of environment, to evaluate embodiment 1 to 9 and comparative example
The yellowing-resistant ability of 1 to 6 polyurethane materials.Yellowness index difference (△ YI) is smaller, indicates that the xanthochromia degree of testing piece is lower,
The yellowing-resistant ability of polyurethane materials is better.Evaluation result is as shown in table 1.
1. oven environment: testing piece is placed on thermo-oxidative ageing in a baking oven (oven temperature is set as 135 DEG C)
One day in (thermal oxidative aging), using color difference meter measure after each testing piece thermo-oxidative ageing compared to
Yellowness index difference (YI before YI- thermo-oxidative ageing after △ YI=thermo-oxidative ageing) before thermo-oxidative ageing.By the way that testing piece is set
Thermo-oxidative ageing is carried out in oven environment, measures the degree of polyurethane materials heat ageing due to caused by high temperature and oxidation and xanthochromia,
The yellowing-resistant ability and oxidation resistance of polyurethane materials can be assessed.
2. indoor environment: testing piece being placed indoors 100 days, measures each testing piece the using the color difference meter
100 days yellowness index differences (the 1st day YI of the 100th day YI- of △ YI=) compared to the 1st day.
3. nitrogen oxides environment: being 6 hours in the environment of 650ppm by the concentration that testing piece is placed on nitrogen oxides (NOx)
Afterwards, yellowness index of each testing piece after being placed in nitrogen oxides environment 6 hours is measured using the color difference meter and be placed in nitrogen oxygen
(YI- after △ YI=is placed in nitrogen oxides environment 6 hours is placed in nitrogen oxides ring to the difference of yellowness index before compound environment
YI before border).By the way that testing piece is placed in nitrogen oxides environment, polyurethane materials are measured because of xanthochromia caused by contacting nitrogen oxides
Degree, polyurethane materials can be assessed to the yellowing-resistant ability of nitrogen oxides.
Table 1
As shown in Table 1, compared to the 1 Polyurethane material of comparative example for not containing any anti-yellowing agent and antioxidant
Material, the polyurethane materials of embodiment 1 to 9 are because having the compound of formula (I) structure described in containing, so in oven environment and interior
Environment all has lesser △ YI, indicates that the polyurethane materials of embodiment 1 to 9 pass through the compound with formula (I) structure
And has preferable yellowing-resistant ability.
And compared to using 2 to 6 polyurethane materials of existing antioxidant and/or the comparative example of anti-yellowing agent, embodiment 3
To 9 polyurethane materials because described in containing with the compound of formula (I) structure, so all having in oven environment and indoor environment
Lesser △ YI indicates that the polyurethane materials of embodiment 3 to 9 have more preferably by the compound with formula (I) structure
Yellowing-resistant ability.
It will be further appreciated that compared to existing antioxidant and the comparative example of anti-yellowing agent 4, embodiment 7 and 8 is used
Polyurethane materials because comprising described in formula (I) structure compound, so even if being placed under nitrogen oxides environment still
With lesser △ YI, indicate that the polyurethane materials of embodiment 7 and 8 are also equipped with by the compound with formula (I) structure
Preferably to the yellowing-resistant ability of nitrogen oxides.
In conclusion polyurethane materials of the present invention are by the compound with formula (I) structure, it is whether old to heat
Change, xanthochromia caused by oxidation and nitrogen oxides all has excellent yellowing-resistant ability, therefore can reach mesh of the invention really
's.
Only as described above, only the embodiment of the present invention is all when cannot be limited the scope of implementation of the present invention with this
It is all still to belong to what the present invention covered according to simple equivalent changes and modifications made by claims of the present invention and description
In range.
Claims (9)
1. a kind of polyurethane materials, it is characterised in that: it includes:
Polyurethane；And
Yellowing-resistant component has the compound of formula (I) structure including one kind,
In formula (I), R1And R2Each independently represent C1To C24Alkyl or C6To C12Aryl, Y1、Y2And Y3Each independently
Indicate that hydrogen or methyl, n indicate 1 to 7 integer.
2. polyurethane materials according to claim 1, it is characterised in that: in the formula (I), the R1And R2It is respectively independent
Ground indicates C1To C24Alkyl.
3. polyurethane materials according to claim 2, it is characterised in that: in the formula (I), the R1And R2It is respectively independent
Ground indicates C10To C24Alkyl.
4. polyurethane materials according to claim 1, it is characterised in that: in the formula (I), n indicates 1 to 4 integer.
5. polyurethane materials according to claim 1, it is characterised in that: the compound with formula (I) structure is choosing
From in formula (I-1) compound represented, formula (I-2) compound represented, formula (I-3) compound represented or above-mentioned any group
It closes.
6. polyurethane materials according to claim 1, it is characterised in that: with the total amount of the Polyurethane for 100 parts by weight,
The amount ranges of the compound with formula (I) structure are 0.01 to 3 parts by weight.
7. polyurethane materials according to claim 1, it is characterised in that: the yellowing-resistant component further includes that hindered phenolic is anti-
At least one of oxidant and hydrazides system anti-yellowing agent.
8. polyurethane materials according to claim 7, it is characterised in that: the hindered phenolic antioxidant is selected from three
Glycol ether-two (3- third butyl -4- hydroxy-5-methyl base phenyl) propionic ester, three (3,5- bis- of 1,3,5- trimethyl -2,4,6-
Third butyl -4- hydroxybenzyl) benzene, 1,3,5- tri- (bis- third butyl -4- hydroxybenzyl of 3,5-) chlorinated isocyanurates, three (4-
Tributyl -3- hydroxyl -2,6- dimethyl benzyl) isocyanuric acid ester or above-mentioned any combination.
9. polyurethane materials according to claim 7, it is characterised in that: hydrazides system anti-yellowing agent is selected from 1,6-
Hexamethylene bis (N, N- dimethylamino urea), 1,1,1', 1'- tetramethyl -4,4'(methylene-two-is to phenylene) double amino
Urea or above-mentioned any combination.
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| CN201910169989.1A CN109880347A (en) | 2019-03-07 | 2019-03-07 | Polyurethane materials |
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| CN201910169989.1A CN109880347A (en) | 2019-03-07 | 2019-03-07 | Polyurethane materials |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113637308A (en) * | 2021-08-17 | 2021-11-12 | 广州仕天材料科技有限公司 | Preparation method of yellowing-resistant photodiffusion PC material |
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Application publication date: 20190614 |