CN104479257A - Application of uracil compound as organic thermal stabilizer of transparent polyester product - Google Patents
Application of uracil compound as organic thermal stabilizer of transparent polyester product Download PDFInfo
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- CN104479257A CN104479257A CN201410852080.3A CN201410852080A CN104479257A CN 104479257 A CN104479257 A CN 104479257A CN 201410852080 A CN201410852080 A CN 201410852080A CN 104479257 A CN104479257 A CN 104479257A
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- uracil
- stabilizer
- pvc
- compound
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Abstract
The invention discloses application of a uracil compound as an organic thermal stabilizer of a transparent polyester product. The formula of the uracil compound is shown by Formula I, where R is a linear chain or branched chain C4-C11 fatty alkyl or a linear chain or branched chain C4-C11 fatty alkenyl. The stabilizer disclosed by the invention has excellent thermostability to PVC products, has better stability than that of the common uracil stabilizer 1,3-dimethyl-6-amido uracil, has little influence on the transparency of the PVC products, and widens the application range of the stabilizer.
Description
(1) technical field
The present invention relates to a kind of uracil thermo-stabilizer and the technology of preparing thereof that can be applied to transparent polyvinyl chloride goods.
(2) background technology
Organic heat stabilizers is a type thermal stabilizing agent conventional in polyvinyl chloride (PVC) processing, due to its not containing metal, has thoroughly broken away from heavy metal contamination, very promising.Market common are machine thermo-stabilizer and mainly contain epoxy compounds, phosphorous acid ester, how much alcohol, beta-diketon etc., but these stablizers can only use as auxiliary stabilizer mostly.In recent years, constantly have paper, patent report part nitrogenous compound can use as PVC main stabilizer, and this is wherein with amino uracil class stablizer best results.
1,3-dimethyl-6-amino uracil (DAU) is a kind of stablizer most widely used in amino uracil class stablizer, but DAU fusing point is far above PVC processing temperature, with PVC poor compatibility, cause its stabilising effect to decline, more affect the transparency of PVC product.
(3) summary of the invention
In order to solve several shortcomings of DAU, the invention provides a kind of novel uracil thermo-stabilizer, for PVC manufacture field.
The technical solution used in the present invention is as follows:
Such as formula the application of the uracil compounds shown in I as the organic heat stabilizers of transparent polyethylene goods:
In formula I, R is C4 ~ C11 fatty alkyl of straight or branched, C4 ~ C11 fat thiazolinyl of straight or branched, is preferably butyl or heptyl.
The present invention also provides the preparation method of the uracil compounds shown in formula I, described method is: 1,3-dimethyl-6-amino uracil, alkanoic R-CHO are in aqueous solvent, stirring at normal temperature is reacted, precipitation is there is in reaction system, reaction represents that reaction terminates when precipitation no longer produces, filter, filter cake washing, dry obtained uracil compounds shown in described formula I, in described alkanoic R-CHO, R is C4 ~ C11 fatty alkyl of straight or branched, C4 ~ C11 fat thiazolinyl of straight or branched, is preferably butyl or heptyl.
The ratio of the amount of substance of described 1,3-dimethyl-6-amino uracil, alkanoic R-CHO is 2:1.
The mass ratio of described 1,3-dimethyl-6-amino uracil, aqueous solvent is 1:600 ~ 1000.
Of the present invention such as formula in the application of the uracil compounds shown in I as the organic heat stabilizers of transparent polyethylene goods, when uracil compounds shown in formula I is as thermo-stabilizer, the quality consumption of the uracil compounds shown in formula I is generally 1 ~ 5% of PVC quality.
The present invention is directed to the above-mentioned shortcoming of DAU, utilize DAU as raw material, design and synthesis New uracils class stablizer, this stablizer not only stabilising effect is better than DAU, PVC product can also be kept transparent, expand the use range of uracil thermo-stabilizer.
Compared with DAU, compound provided by the present invention has following beneficial effect:
1, compound stability excellent effect provided by the present invention, owing to introducing Long carbon chain on molecular structure, reduce the fusing point of this compound, this compound is existed in liquid form under PVC processing temperature, easilier to disperse in PVC matrix, and then more easily replace unstable group in PVC chain, improve stablizer utilization ratio.
2, compound provided by the present invention contains Long carbon chain, and not only fusing point is low, also good with PVC consistency, little on the impact of PVC transparent degree, can be used in transparent PVC product, expand the use range of uracil thermo-stabilizer.
3, the synthesis technique of stablizer of the present invention is simple, makees solvent with water, and without the need to catalyzer, without the need to heating, process energy consumption is low, step is few and pollution-free, is conducive to applying of stablizer of the present invention.
(4) accompanying drawing explanation
The thermal stability comparison diagram of the different thermo-stabilizers of Fig. 1 under oven heat weathering test method.
The PVC sample transparency photo of Fig. 2 different stabilizers.In figure, the stablizer that PVC sample uses from left to right is respectively DAU, Ca/Zn, embodiment 1 Compound II per-1, embodiment 2 Compound II per-2.
(5) embodiment
Below by embodiment, technical scheme of the present invention is further described in detail, but protection scope of the present invention is not limited thereto.
Embodiment 1: in the there-necked flask of 500 milliliters that whipping appts is housed, adds 0.31 gram of 1,3-dimethyl-6-amino uracil, 0.086 gram of valeraldehyde and 250 ml distilled waters, open whipping appts, normal-temperature reaction 24 hours, now no longer produces precipitation in reaction system.Reaction terminates rear filtration, and filter cake distilled water wash 3 times, puts into convection oven and be drying to obtain target product II-1, productive rate 90.3%, white solid, fusing point 200.1 DEG C.
1H-NMR(500MHz,DMSO-d
6):δ＝0.80-0.84(m,3H,CH
3),1.11-1.13(m,2H,CH
2),1.20-1.31(m,4H,CH
2CH
2),2.04(br.s,2H,NH
2),3.16(s,6H,2NCH
3),3.28(s,6H,2NCH
3),4.02-4.07(m,1H,CH),7.25(br.s,2H,NH
2)。
Embodiment 2: in the there-necked flask of 500 milliliters that whipping appts is housed, adds 0.31 gram of 1,3-dimethyl-6-amino uracil, 0.128 gram of n-octaldehyde and 250 ml distilled waters, open whipping appts, normal-temperature reaction 36 hours, now no longer produces precipitation in reaction system.Reaction terminates rear filtration, and filter cake distilled water wash 3 times, puts into convection oven and be drying to obtain target product II-2, productive rate 93.4%, faint yellow solid, fusing point 176.8 DEG C.
1H-NMR(500MHz,DMSO-d
6):δ＝0.81-0.87(m,3H,CH
3),1.08-1.14(m,2H,CH
2),1.16-1.28(m,12H,6CH
2),2.12(br.s,2H,NH
2),3.16(s,6H,2NCH
3),3.28(s,6H,2NCH
3),4.02-4.08(m,1H,CH),7.25(br.s,2H,NH
2)。
The uracil compound that the present invention obtains can use as a kind of PVC heat stabilizer, and concrete function combines embodiment and is described in further detail.
Embodiment 3:
Uracil compound II-2 and 1 obtained in the Compound II per-1 that Example 1 obtains, embodiment 2,3-dimethyl-6-amino uracil (DAU), calcium zinc stabilizer (Ca/Zn, the mixture of Zinic stearas and calcium stearate 1:1 in mass ratio) carry out simultaneous test respectively as PVC heat stabilizer, all components is weighed by formula in table 1, be added to after mechanical stirring mixes two roller mill is carried out mixing, after mixing 5 minutes, take out compound and be put into sample compression molding instrument being pressed into 1 mm of thickness.Then test thermal stability and the transparency of above-mentioned obtained sample, experimental result as shown in Figure 1 and Figure 2.Fig. 1 display uses the different stabilizers of oven heat ageing process mensuration on the impact of PVC thermal stability, and PVC puts into the baking oven of 180 DEG C, aging different time, and photo as shown in Figure 1.As shown in Figure 1, several uracil compounds is all good than calcium zinc stabilizer stabilising effect, and the compound obtained by embodiment 1 and DAU stabilising effect are suitable, and compound obtained by embodiment 2 is more obvious than DAU stabilising effect better.As shown in Figure 2, stablizer used from left to right is respectively DAU to the transparency photo of the PVC sample that different stabilizers obtains, Ca/Zn, embodiment 1 Compound II per-1, embodiment 2 Compound II per-2.
As shown in Figure 2, although DAU thermostable effect is pretty good, but greatly reduce the transparency of PVC product, also poorer than the goods using calcium zinc stabilizer, and the compound obtained by the present invention affects less on PVC transparent degree, the PVC product of embodiment 2 Compound II per-2 has particularly been used still to maintain very high transparency.
Table 1 basic recipe
Claims (2)
1. such as formula the application of the uracil compounds shown in I as the organic heat stabilizers of transparent polyethylene goods:
In formula I, R is C4 ~ C11 fatty alkyl of straight or branched, C4 ~ C11 fat thiazolinyl of straight or branched.
2. apply as claimed in claim 1, it is characterized in that described R is butyl or heptyl.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410852080.3A CN104479257A (en) | 2014-12-31 | 2014-12-31 | Application of uracil compound as organic thermal stabilizer of transparent polyester product |
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|---|---|---|---|
| CN201410852080.3A CN104479257A (en) | 2014-12-31 | 2014-12-31 | Application of uracil compound as organic thermal stabilizer of transparent polyester product |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105315485A (en) * | 2015-11-05 | 2016-02-10 | 浙江工业大学 | Organic transparent compound heat stabilizer, as well as preparation method and application thereof |
| CN107698896A (en) * | 2017-10-31 | 2018-02-16 | 山东国塑科技实业有限公司 | PVC U feed pipes and preparation method thereof |
| CN110041270A (en) * | 2019-05-22 | 2019-07-23 | 广州臻莱迈新材料科技有限公司 | A kind of preparation method of double semicarbazides pyrimidines in water phase |
| CN110317418A (en) * | 2019-06-03 | 2019-10-11 | 盐城市朗创新材料有限公司 | A kind of Environment-friendlyheat heat stabilizer and preparation method thereof for PVC hard product |
| CN111662481A (en) * | 2020-06-30 | 2020-09-15 | 内蒙古科技大学 | Uracil-rare earth composite stabilizer for PVC (polyvinyl chloride) and preparation method thereof |
| CN113444287A (en) * | 2021-06-23 | 2021-09-28 | 浙江宏天新材料科技有限公司 | Modified hydrotalcite, preparation method thereof, PVC heat stabilizer and application |
| CN113912553A (en) * | 2021-11-10 | 2022-01-11 | 山东慧科助剂股份有限公司 | Pentanal diurea pyrimidine, preparation method and application thereof |
| CN114014816A (en) * | 2021-11-10 | 2022-02-08 | 山东慧科助剂股份有限公司 | Octanal diurea pyrimidine, preparation method and application thereof |
| CN114163754A (en) * | 2021-12-22 | 2022-03-11 | 富海(东营)新材料科技有限公司 | PVC high-transparency antibacterial hard product and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6156830A (en) * | 1998-06-26 | 2000-12-05 | Witco Vinyl Additives Gmbh | 5-substituted 6-aminouracils as stabilizers for halogenated polymers |
-
2014
- 2014-12-31 CN CN201410852080.3A patent/CN104479257A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6156830A (en) * | 1998-06-26 | 2000-12-05 | Witco Vinyl Additives Gmbh | 5-substituted 6-aminouracils as stabilizers for halogenated polymers |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105315485A (en) * | 2015-11-05 | 2016-02-10 | 浙江工业大学 | Organic transparent compound heat stabilizer, as well as preparation method and application thereof |
| CN107698896A (en) * | 2017-10-31 | 2018-02-16 | 山东国塑科技实业有限公司 | PVC U feed pipes and preparation method thereof |
| CN110041270A (en) * | 2019-05-22 | 2019-07-23 | 广州臻莱迈新材料科技有限公司 | A kind of preparation method of double semicarbazides pyrimidines in water phase |
| CN110317418A (en) * | 2019-06-03 | 2019-10-11 | 盐城市朗创新材料有限公司 | A kind of Environment-friendlyheat heat stabilizer and preparation method thereof for PVC hard product |
| CN111662481A (en) * | 2020-06-30 | 2020-09-15 | 内蒙古科技大学 | Uracil-rare earth composite stabilizer for PVC (polyvinyl chloride) and preparation method thereof |
| CN113444287A (en) * | 2021-06-23 | 2021-09-28 | 浙江宏天新材料科技有限公司 | Modified hydrotalcite, preparation method thereof, PVC heat stabilizer and application |
| CN113912553A (en) * | 2021-11-10 | 2022-01-11 | 山东慧科助剂股份有限公司 | Pentanal diurea pyrimidine, preparation method and application thereof |
| CN114014816A (en) * | 2021-11-10 | 2022-02-08 | 山东慧科助剂股份有限公司 | Octanal diurea pyrimidine, preparation method and application thereof |
| CN114163754A (en) * | 2021-12-22 | 2022-03-11 | 富海(东营)新材料科技有限公司 | PVC high-transparency antibacterial hard product and preparation method thereof |
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Application publication date: 20150401 |