CN104945783B - A kind of PVC polyester plasticizer and its preparation method and application - Google Patents
A kind of PVC polyester plasticizer and its preparation method and application Download PDFInfo
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- CN104945783B CN104945783B CN201510444631.7A CN201510444631A CN104945783B CN 104945783 B CN104945783 B CN 104945783B CN 201510444631 A CN201510444631 A CN 201510444631A CN 104945783 B CN104945783 B CN 104945783B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of PVC polyester plasticizer and its preparation method and application, which solve prior art PVC poor compatibility, the inefficient technical problem of plasticization, it is colourless oily transparency liquid, and mean molecule quantity is 2500～5500, and the viscosity of 25 DEG C is 1.0～4.0Pa s.Invention also provides its preparation method and application.The present invention can be used for the preparation of PVC product.
Description
Technical field
The present invention relates to a kind of PVC plasticizer and its preparation method and application, particularly a kind of PVC
Polyester plasticizer and its preparation method and application.
Background technology
Polrvinyl chloride (PVC) is one of five big resins for universal use, and its yield is only second to polyethylene.?
In the course of processing of polrvinyl chloride (PVC) material, plasticizer is one of auxiliary agent of consumption maximum.
Plasticizer is to add in high polymer (such as rubber, plastics, coating etc.), increases when machine-shaping
Its plasticity and mobility also make finished product have a flexible class Ester.
For a long time, in PVC material, the plasticizer of use is mainly based on phthalate,
Along with phthalate application in the industries such as medical apparatus and instruments, food, toy, artificial leather
More and more extensive, its toxicity is the most increasingly paid attention to by people.Environmental Protection in America general bureau is according to country's cancer
Disease result of study, limited six kinds of phthalate primary plasticizers and in environmental protection and defended
Lifes etc. require the application in higher industry, such as toy and articles for children, medical supplies, food bag
Package material etc..Phthalic acid two (2-ethyl) own ester in the plastic of the countries such as outlet European Union
(DEHP or DOP), dibutyl phthalate (DBP), BBP(Butyl Benzyl Phthalate (BBP),
Diisononyl phthalate (DINP), diisooctyl phthalate (DIDP) and adjacent benzene two
The content of formic acid n-octyl (DNOP) plasticizer does not allow more than 0.1%；DEHP, DBP and
Tri-kinds of plasticizers of BBP are prohibited to add toy and all articles for children plastics to；DINP、
In DIDP and DNOP tri-, plasticizer disabling scope is for may be put into by three years old and less than three years old child
Toy in Kou and the plastics of articles for children, DOP is only limited in the packaging for foodstuff of high water content
Using, meat Package must use other nontoxic plasticizer product to substitute.
Universal phthalic ester plasticizer in addition to there is potential carcinogenecity, again due to
The little molecular characterization of itself, easily migrates in PVC product and is extracted out by solvent, not only affecting
Properties of product, the most directly threaten the health of the mankind.
Summary of the invention
The present invention is directed to existing in order to overcome prior art PVC poor compatibility, plasticization inefficient
Technical problem, it is provided that one is good with the PVC compatibility, plasticization efficiency high, it is low to pollute, quality is high
PVC polyester plasticizer high with product purity and its preparation method and application.
To this end, the present invention provides a kind of PVC polyester plasticizer, it is colourless oily transparency liquid,
Mean molecule quantity is 2500～5500, and the viscosity of 25 DEG C is 1.0～4.0Pa s.
Preferably, PVC polyester plasticizer mean molecule quantity is 3000～4000, and the viscosity of 25 DEG C is
2.0～3.5Pa s.
Present invention simultaneously provides the preparation method of a kind of PVC polyester plasticizer, it uses following steps
: by adipic acid, dihydroxylic alcohols during 1:1.2～1:1.5 joins esterifier in molar ratio, add
The catalyst of total inventory quality 0.05%～0.1%, adds total inventory quality 10%～20%
Water entrainer, sluggish is warming up to 180 DEG C～220 DEG C, is passed through under high pure nitrogen normal pressure stirring simultaneously
Reaction, protection reaction system is not oxidized and avoids various side reaction, until reaction system stops
Water, the per hour acid number of tracking and measuring system, when the acid number in system remains unchanged and drops to
During below 1mgKOH/g, stopped reaction, it is cooled to room temperature under nitrogen protection, adds end-capping reagent acetic acid
Acid anhydride, in an amount of from the 0.2～0.6 of adipic acid molal quantity, reacts 2h～5h at a temperature of 50 DEG C～80 DEG C,
Changing steam stripping at reduced pressure device, controlling stripping temperature is 120 DEG C～160 DEG C, and stripping time is 1h～4h,
Alcohol and water entrainer and the lower boiling little molecular product of excess are taken out of, i.e. under the effect of water vapour
Obtain PVC polyester plasticizer product；Stripping temperature be 130 DEG C～150 DEG C, stripping time be 2h～
3h；PVC polyester plasticizer mean molecule quantity is 3000～4000, and the viscosity of 25 DEG C is 2.0～3.5
Pa·s。
Preferably, dihydroxylic alcohols is ethylene glycol, diethylene glycol, 1,2-PD, 1,3-PD, 2-
Three kinds or more in propyl enanthol, 1,3 butylene glycol, 1,4-butanediol, neopentyl glycol
Combination.
Preferably, catalyst is dibutyl tin laurate, tetra-n-butyl titanate and metatitanic acid four isopropyl
One or more in ester.
Preferably, the one during water entrainer is toluene and hexamethylene.
Present invention simultaneously provides the application in preparing pvc material of the PVC polyester plasticizer.This
The PVC polyester plasticizer of invention can be used alone as the primary plasticizer of PVC, it is possible to this area
Conventional plasticizers be used together.Can be by following components consumption processing PVC: plasticizer: stabilizer is
100:(40～60): (1～2).Wherein, plasticizer is the novel PVC polyester plasticising of the present invention
One in agent, or the Conventional plasticizers of the novel PVC polyester plasticizer of the present invention and this area or
The combination of multiple plasticizer, stabilizer is calcium zinc, organotin or rare earth.
Compared to existing technology, the beneficial effects of the present invention is:
(1) product appearance that the present invention produces is almost colourless oily transparency liquid, color number (platinum
-cobalt method)≤30, acid number≤1mgKOH/g, mean molecule quantity is 2500～5500, the viscosity of 25 DEG C
Being 1.0～4.0Pa s, preferred mean molecule quantity is 3000～4000, the viscosity of 25 DEG C be 2.0～
3.5Pa s, product has the advantages that pollution is low, quality is high and product purity is high；
(2) present invention is good with the compatibility of PVC, and plasticization efficiency is high, can be as the main increasing of PVC
Mould agent to use, it is possible to be used together with other Conventional plasticizers of this area；
(3) the PVC product extractable of resistance to ethanol of the present invention and the animal migration of resistance to normal heptane are splendid；
(4) the novel PVC polyester plasticizer tool of the present invention has been widely used, and can be widely used for doctor
Treat the industries such as apparatus, packaging for foodstuff, toy, artificial leather, and can be directly used for being processed into different use
The nontoxic PVC product on way, considerably reduces the loss in goods processing and pollution, reduces system
Product cost.
Detailed description of the invention
Below by embodiment, the present invention is further illustrated, but the present invention is not by embodiment
Limit.In the present invention, reacting substance used is conventional commercial.
Embodiment 1
At 500ml equipped with the glass of agitator, water knockout drum, filled column, spherical condensation tube and thermometer
Glass four-hole boiling flask adds 146.14g adipic acid, 38.75g diethylene glycol, 44.78g 1,2-PD,
32.72g BDO, adds 0.26g (the 0.1% of gross mass) dibutyl tin laurate and urges
Agent, adds 39.40g (the 15% of gross mass) cyclohexane, is passed through high pure nitrogen, stirs
Mix and be to slowly warm up to 220 DEG C of reactions, in time having moisture to go out, start timing, measure the most every other hour once
Acid number, when acid number is down to 1mgKOH/g, stops heating, is cooled to room temperature, adds under logical nitrogen
51.05g end-capping reagent acetic anhydride, reacts 2h, changes steam stripping at reduced pressure device at 70 DEG C, control stripping temperature
Degree is 150 DEG C, strips 2h, is cooled to room temperature, obtains novel PVC polyester plasticising under decompression state
Agent；
Product appearance is substantially colorless oily transparency liquid, ester content 99.5%, finished product acid number
0.79mgKOH/g, the viscosity of color number (platinum-cobalt method) 30,25 DEG C is 2940Pa s.
By following component consumption: 100 parts of PVC powder, novel PVC polyester plasticizer 40 parts, calcium zinc
Stabilizer 1 part, 160 DEG C of banburyings, tabletting.Carried out resistance to ethanolic extraction and resistance to normal heptane animal migration
Test experiments, resistance to ethanolic extraction test condition is 50 DEG C, 30min, resistance to normal heptane animal migration test strip
Part is under room temperature, soaks 30min.
Embodiment 2
At 500ml equipped with the glass of agitator, water knockout drum, filled column, spherical condensation tube and thermometer
Glass four-hole boiling flask adds 146.14g adipic acid, 36.05g 1,3 butylene glycol, 30.44g 1,2-
Propylene glycol, 42.22g ethylene glycol, add 0.13g (the 0.05% of gross mass) tetra-n-butyl titanate
Catalyst, adds 25.5g (the 10% of gross mass) methylbenzene water-taking agent, is passed through high pure nitrogen, stirring
It is to slowly warm up to 200 DEG C of reactions, in time having moisture to go out, starts timing, measure a subacid the most every other hour
Value, when acid number is down to 1mgKOH/g, stops heating, is cooled to room temperature, adds 30.63g under logical nitrogen
End-capping reagent acetic anhydride, reacts 3h, changes steam stripping at reduced pressure device at 50 DEG C, controlling stripping temperature is 130
DEG C, strip 3h, under decompression state, be cooled to room temperature, filter, obtain novel PVC polyester plasticizer；
Product appearance is substantially colorless oily transparency liquid, ester content 99.5%, finished product acid number
0.92mgKOH/g, the viscosity of color number (platinum-cobalt method) 25,25 DEG C is 3250Pa s.
By following component consumption: 100 parts of PVC powder, novel PVC polyester plasticizer 40 parts, calcium zinc
Stabilizer 1 part, 160 DEG C of banburyings, tabletting.Carried out resistance to ethanolic extraction and resistance to normal heptane animal migration
Test experiments, resistance to ethanolic extraction test condition is 50 DEG C, 30min, resistance to normal heptane animal migration test strip
Part is under room temperature, soaks 30min.
Embodiment 3
At 500ml equipped with the glass of agitator, water knockout drum, filled column, spherical condensation tube and thermometer
Glass four-hole boiling flask adds 146.14g adipic acid, 37.85g diethylene glycol, 43.74g 2-propyl group heptan
Alcohol, 31.96g neopentyl glycol, add 0.19g (the 0.075% of gross mass) tetraisopropyl titanate and urge
Agent, adds 51.94g (the 20% of gross mass) methylbenzene water-taking agent, is passed through high pure nitrogen, stirring
It is to slowly warm up to 180 DEG C of reactions, in time having moisture to go out, starts timing, measure a subacid the most every other hour
Value, when acid number is down to 1mgKOH/g, stops heating, is cooled to room temperature, adds 87.68g under logical nitrogen
End-capping reagent acetic anhydride, reacts 1h, changes steam stripping at reduced pressure device at 80 DEG C, controlling stripping temperature is 140
DEG C, strip 2.5h, under decompression state, be cooled to room temperature, filter, obtain novel PVC polyester plasticising
Agent；
Product appearance is substantially colorless oily transparency liquid, ester content 99.6%, finished product acid number
0.79mgKOH/g, the viscosity of color number (platinum-cobalt method) 25,25 DEG C is 3025Pa s.
By following component consumption: 100 parts of PVC powder, novel PVC polyester plasticizer 40 parts, calcium zinc
Stabilizer 1 part, 160 DEG C of banburyings, tabletting.Carried out resistance to ethanolic extraction and resistance to normal heptane animal migration
Test experiments, resistance to ethanolic extraction test condition is 50 DEG C, 30min, resistance to normal heptane animal migration test strip
Part is under room temperature, soaks 30min.
The Performance comparision of 1 three kinds of plasticizers of table
Note: W-2050 is that DIC company of Japan produces.
As it can be seen from table 1 the resistance to ethanolic extraction of the present invention and resistance to normal heptane animal migration are excellent.
Above-mentioned embodiment is only the preferred embodiment of the present invention, it is impossible to limit the present invention with this
The scope of protection, any unsubstantiality that those skilled in the art is done on the basis of the present invention
Change belong to scope of the present invention.
Claims (4)
1. a preparation method for PVC polyester plasticizer, is characterized in that comprising the steps: oneself
Diacid, dihydroxylic alcohols 1:(1.2 in molar ratio～1.5) join in esterifier, add total throwing
The catalyst of doses quality 0.05%～0.1%, adds the band water of total inventory quality 10%～20%
Agent, sluggish is warming up to 180 DEG C～220 DEG C, is passed through under high pure nitrogen normal pressure stirring reaction simultaneously,
Protection reaction system is not oxidized and avoids various side reaction, until reaction system stops water outlet, often
The acid number of hour tracking and measuring system, when the acid number in system remain unchanged and drop to 1mgKOH/g with
Time lower, stopped reaction, it is cooled to room temperature under nitrogen protection；Add end-capping reagent acetic anhydride, in an amount of from
The 0.2～0.6 of adipic acid molal quantity, reacts 2h～5h at a temperature of 50 DEG C～80 DEG C, change decompression vapour
Carrying device, controlling stripping temperature is 120 DEG C～160 DEG C, and stripping time is 1h～4h, by excess
Alcohol and water entrainer and lower boiling little molecular product are taken out of under the effect of water vapour, i.e. obtain PVC
Polyester plasticizer；Described stripping temperature is 130 DEG C～150 DEG C, and stripping time is 2h～3h；PVC
Polyester plasticizer mean molecule quantity is 3000～4000, and the viscosity of 25 DEG C is 2.0～3.5Pa s.
The preparation method of PVC polyester plasticizer the most according to claim 1, it is characterised in that institute
State dihydroxylic alcohols be ethylene glycol, diethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 2-propyl enanthol,
The combination of the three kinds or more in 1,3 butylene glycol, 1,4-butanediol, neopentyl glycol.
The preparation method of PVC polyester plasticizer the most according to claim 1, it is characterised in that institute
Stating catalyst is the one in dibutyl tin laurate, tetra-n-butyl titanate and tetraisopropyl titanate
Or it is multiple.
The preparation method of PVC polyester plasticizer the most according to claim 1, it is characterised in that institute
Stating water entrainer is the one in toluene and hexamethylene.
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| CN105504238A (en) * | 2016-01-07 | 2016-04-20 | 武汉纺织大学 | Preparation method of monobutyl ether alcohol terminated polyester plasticizer |
| CN110078902B (en) * | 2019-05-24 | 2021-09-24 | 镇江巨杰新材料技术研发中心(有限合伙) | Method for synthesizing glycol polyester plasticizer |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102786780A (en) * | 2012-07-10 | 2012-11-21 | 苏州宝津塑业有限公司 | PVC polyester plasticizing material |
| CN103242516A (en) * | 2013-05-23 | 2013-08-14 | 江南大学 | Preparation method of glyceryl polyester used as PVC (Polyvinyl Chloride) plasticizer |
| CN103319698A (en) * | 2013-06-19 | 2013-09-25 | 佛山市顺德区天晟贸易有限公司 | Polymer polyester plasticizer as well as preparation method and application thereof |
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| ATE205509T1 (en) * | 1999-12-23 | 2001-09-15 | Basf Ag | POLYESTERS TERMINATED WITH ISOMERS NONANOLS, METHOD FOR THEIR PRODUCTION AND THEIR USE AS PLASTICIZERS |
| DE10141250A1 (en) * | 2001-08-23 | 2003-03-06 | Basf Ag | Plasticizers for plastics |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102786780A (en) * | 2012-07-10 | 2012-11-21 | 苏州宝津塑业有限公司 | PVC polyester plasticizing material |
| CN103242516A (en) * | 2013-05-23 | 2013-08-14 | 江南大学 | Preparation method of glyceryl polyester used as PVC (Polyvinyl Chloride) plasticizer |
| CN103319698A (en) * | 2013-06-19 | 2013-09-25 | 佛山市顺德区天晟贸易有限公司 | Polymer polyester plasticizer as well as preparation method and application thereof |
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Address after: No.19 Zhuhai east road, economic development zone, Wendeng District, Weihai City, Shandong Province 264400 Patentee after: SHANDONG ONETWO POLYMER MATERIALS Co.,Ltd. Address before: 264400 Dongshou, Zhuhai east road, Wendeng Economic Development Zone, Weihai City, Shandong Province Patentee before: SHANDONG ONE TW POLYMER MATERIALS Co.,Ltd. |
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Denomination of invention: A PVC polyester plasticizer and its preparation method and application Effective date of registration: 20230721 Granted publication date: 20160824 Pledgee: Weihai Branch of Shanghai Pudong Development Bank Co.,Ltd. Pledgor: SHANDONG ONETWO POLYMER MATERIALS CO.,LTD. Registration number: Y2023980049213 |