WO2020098184A1 - 一种用超/亚临界流体脱除海绵中挥发性有机物的方法 - Google Patents

一种用超/亚临界流体脱除海绵中挥发性有机物的方法 Download PDF

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Publication number
WO2020098184A1
WO2020098184A1 PCT/CN2019/077409 CN2019077409W WO2020098184A1 WO 2020098184 A1 WO2020098184 A1 WO 2020098184A1 CN 2019077409 W CN2019077409 W CN 2019077409W WO 2020098184 A1 WO2020098184 A1 WO 2020098184A1
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extraction
foam
carbon dioxide
pressure
volatile organic
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Ceased
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PCT/CN2019/077409
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English (en)
French (fr)
Chinese (zh)
Inventor
任其龙
鲍宗必
陈富强
张治国
陈旻
杨亦文
杨启炜
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Zhejiang University ZJU
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Zhejiang University ZJU
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Priority to JP2021524205A priority Critical patent/JP7248253B2/ja
Priority to EP19884606.5A priority patent/EP3878899B1/en
Publication of WO2020098184A1 publication Critical patent/WO2020098184A1/zh
Priority to US17/321,463 priority patent/US20210269615A1/en
Anticipated expiration legal-status Critical
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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/36After-treatment
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/36After-treatment
    • C08J9/40Impregnation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00Use of inorganic substances as compounding ingredients
    • C08K3/18Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20Oxides; Hydroxides
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J3/00Processes of utilising sub-atmospheric or super-atmospheric pressure to effect chemical or physical change of matter; Apparatus therefor
    • B01J3/008Processes carried out under supercritical conditions
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2309/00Characterised by the use of homopolymers or copolymers of conjugated diene hydrocarbons
    • C08J2309/06Copolymers with styrene
    • C08J2309/08Latex
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2321/00Characterised by the use of unspecified rubbers
    • C08J2321/02Latex
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2329/00Characterised by the use 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 an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
    • C08J2329/02Homopolymers or copolymers of unsaturated alcohols
    • C08J2329/04Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04Polyurethanes
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/54Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

  • the invention relates to the technical field of volatile organic compounds treatment, in particular to a method for removing volatile organic compounds in sponges by using super / subcritical fluids.
  • Sponge products have been favored by people because of their excellent characteristics such as high resilience, good breathability, light weight, and comfortable texture.
  • Sponge products are mainly divided into rubber sponges (latex sponges), polyurethane foams (polyether and polyester sponges) and polyvinyl alcohol sponges due to different synthetic raw materials. Latex sponges and polyurethane foams are the most widely used.
  • Latex sponge has become a hot product in recent years because of its advantages of good breathability, antibacterial and anti-mite, and promotion of sleep.
  • the output of natural latex is low, and each rubber tree can only produce 30cc of latex juice per day.
  • natural rubber and synthetic styrene-butadiene rubber are usually blended and produced. It is obtained by copolymerization of ene and styrene; and latex sponges have many pores due to evaporation molding, and after processing processes such as foaming and vulcanization, many unreacted volatile organic compounds will remain. This will not only give the sponge an odor, but may cause harm to the human body through inhalation, ingestion or percutaneous absorption.
  • Polyurethane foam is widely used as cushions, mattresses, clothing linings, filters, sound absorption, dust absorption, shockproof, packaging materials due to its good properties such as cold resistance, shock resistance, sound absorption, and dust absorption.
  • Polyurethane foam is mainly formed by the reaction of isocyanate and polyether / polyester polyol to form a sponge cross-linked structure, which is finally formed through processing techniques such as foaming and vulcanization.
  • the common methods for removing volatile organic compounds in polymer latex at home and abroad are stripping method, post polymerization method and stripping-post polymerization method.
  • the main technical key of the stripping method is that the steam is introduced under the condition of vacuum to remove the residual monomers, and the efficiency of removing monomers depends largely on the contact area of steam and latex.
  • the German patent (DE 2717996) sprays polymer latex and steam into a container to improve the efficiency of monomer removal.
  • US patent (US4130527) and the Japanese patent (JP09220402) respectively reported an improved stripping equipment, which increases the monomer removal efficiency by increasing the contact area between steam and latex.
  • the post-polymerization method is to add a high-efficiency initiator after the monomer is basically polymerized to continue the polymerization so that the residual monomer is basically completely converted.
  • the US patent US43012664 reported that after the emulsion polymerization to a certain extent, the second initiator was added to continue the polymerization under certain conditions to reduce the amount of residual monomers to less than 0.1%.
  • the post-polymerization method has higher requirements on the initiator and must have both high activity and selectivity.
  • the stripping-post-polymerization method combines the stripping method with the post-polymerization method to improve the monomer removal efficiency, but the method is relatively complicated.
  • the United States patent (US4529573) reports the stripping-postpolymerization method. The initiator was continuously added at the same time as the steam stripping, and the amount added per hour was 0.01% of the latex until the residual monomer content decreased to 0.05%.
  • the invention provides a super / subcritical fluid removal method for volatile organic compounds in sponges.
  • the super / subcritical fluids are used to remove residual volatile organic compounds in sponges to obtain sponges with quality standards.
  • a method for removing volatile organic compounds in sponges with super / subcritical fluids includes the following steps:
  • the devolatilization device used in the present invention is supercritical extraction equipment, which can adopt static extraction or dynamic extraction or a combination of the two, that is, during static extraction, CO 2 and the sponge to be processed in the above device are contacted and mass transferred for a certain time in the separation kettle
  • the pressure is released and dynamic extraction and devolatilization, that is, CO 2 passes through the devolatilization device or extraction device at a certain flow rate, the volatile organic compounds in the sponge are taken out of the devolatilization device along with CO 2 .
  • super / subcritical fluids have good selectivity, and the fluid density and dissolution performance can be adjusted by changing the temperature and pressure to achieve the dissolution and removal of the target.
  • Super / subcritical fluids have unique physicochemical properties: (1) the density is close to that of liquids, which enhances their ability to dissolve many compounds and can be effectively regulated; (2) the transfer properties are similar to gases and have zero surface tension , So that the mass transfer performance of the high-viscosity system can be enhanced.
  • CO 2 is an environmental gas with mild critical properties (critical temperature is 304K, critical pressure is 7.39MPa), and it is non-toxic, cheap, non-flammable, inert, etc., and the solvent and solute are easily separated to achieve no residual solvent in the product And can be recycled to reduce the impact on the operator's health and environmental pollution, is the preferred supercritical medium.
  • the supercritical fluid medium is pure or modified supercritical carbon dioxide.
  • the modified super / subcritical carbon dioxide is formed by adding a modifier to the pure super / subcritical carbon dioxide in a proportion.
  • the modifier is ethanol or isopropanol.
  • the amount of modifier added is 0.5 to 20 wt% of the mass of pure super / subcritical carbon dioxide.
  • the modified super / subcritical fluid is a mixed solvent of modifier and carbon dioxide.
  • the proportion of the modifier is small, and the main body is carbon dioxide. Adding the modifier can increase the polarity of the fluid and enhance the solubility.
  • Supercritical conditions refer to the operating temperature and pressure not lower than the critical temperature of carbon dioxide (31.1 °C) and critical pressure (7.39MPa); subcritical conditions refer to the operating temperature and pressure slightly lower than the critical temperature of carbon dioxide (31.1 °C) and critical Pressure (7.39MPa).
  • the supercritical conditions are: 31.1 ° C ⁇ temperature ⁇ 60 ° C, 7.39MPa ⁇ pressure ⁇ 25Mpa MPa; the subcritical conditions are: 20 ° C ⁇ temperature ⁇ 31.1 ° C, 3MPa ⁇ pressure ⁇ 7.39MPa.
  • the supercritical condition is that the control temperature is greater than or equal to the critical temperature of CO 2 and less than the oxidation temperature of the sponge, 31.1 ° C ⁇ temperature ⁇ 60 ° C, 7.39MPa ⁇ pressure ⁇ 25Mpa MPa.
  • the supercritical fluid has a higher diffusion coefficient than the liquid and a dissolution performance equivalent to that of the liquid solvent, and the operating conditions are milder, and the energy consumption of the production process is lower, which is conducive to controlling production costs.
  • the extraction time is 5-30 min.
  • the flow rate of the supercritical body medium during dynamic extraction is adjusted according to the amount of treatment.
  • the flow rate of the supercritical medium during dynamic extraction is 100 kg / h to 200 kg / h.
  • the sponge blocks to be treated include but are not limited to latex sponges or polyurethane foams or polyvinyl alcohol sponges.
  • the volatile organic compounds in the latex mattress include but are not limited to styrene, 1,3-butadiene, 4-vinylcyclohexene, etc.
  • the volatile organic compounds in the latex sponge in the polyurethane foam include but not Limited to 2,4-toluenediamine and 4,4'-diaminodiphenylmethane.
  • the extraction time can be determined according to the volatile organic content in the sponge to be treated and the quality standard that the sponge needs to reach, and the extraction time depends on the flow rate of the supercritical fluid.
  • the separated carbon dioxide gas is returned to the extraction kettle for recycling.
  • the content of volatile organic compounds can be analyzed and determined by static headspace sampling-mass spectrometry or environmental chamber method.
  • this method implements super / subcritical fluid devolatilization of volatile organic compounds in sponges, and its technical effects are mainly reflected in the following two aspects:
  • Figure 1 is a process flow diagram of the method of the present invention.
  • FIG. 1 The process flow of the present invention is shown in FIG. 1, which includes a carbon dioxide storage tank 1, a condenser 2, a carbon dioxide intermediate storage tank 3, a carbon dioxide pump 4, an extraction kettle 7 and a separation kettle 6 connected in sequence, and the entraining agent storage tank 5 is composed of an entraining agent
  • the pump 6 is connected to the feed inlet of the extraction kettle 7, and a valve is provided at the entrance and exit of each equipment.
  • the carbon dioxide After being condensed by the condenser, the carbon dioxide is sent to the carbon dioxide intermediate storage tank 3, and the jacket of the intermediate storage tank is sent to the refrigerant to maintain the low temperature in the tank.
  • the carbon dioxide in the intermediate storage tank is metered by the carbon dioxide pump 4 and fed into the inlet of the extraction kettle 7
  • the valve of the entraining agent storage tank 5 is closed.
  • the valve of the entraining agent storage tank is opened at the same time. Feed.
  • the top outlet of the extraction kettle is connected to the inlet of the separation kettle, and the carbon dioxide separated by the separation kettle is returned to the intermediate storage tank for recycling.
  • the total volatile organic compound emission in 24 hours was 35 ⁇ g / m 3 , in line with relevant national standards, the total removal rate is greater than 99%, of which styrene release is 1.2 ⁇ g / m 3 , 4-vinylcyclohexene content is 1.0 ⁇ g / m 3 , 1,3-butadiene The release amount is 0.9 ⁇ g / m 3 , which is in compliance with EU standards.
  • the total removal rate is greater than 99%, of which styrene release is 0.4 ⁇ g / m 3 , 4-vinylcyclohexene content is 0.9 ⁇ g / m 3 , 1,3-butadiene
  • the release amount is 0.1 ⁇ g / m 3 , which conforms to EU standards.
  • the total removal rate is greater than 99%, of which styrene release is 0.4 ⁇ g / m 3 , 4-vinylcyclohexene content is 0.6 ⁇ g / m 3 , and 1,3- is not detected Butadiene release, in line with EU standards.
  • the total volatile organic compound emissions in 24 hours were 12 ⁇ g / m 3 , in line with the relevant national standards, the total removal rate is greater than 99%, of which, the release of styrene is 0.2 ⁇ g / m 3 , the content of 4-vinylcyclohexene is 0.2 ⁇ g / m 3 , 1,3- is not detected Butadiene release, in line with EU standards.
  • the total removal rate is greater than 99%, of which styrene release is 0.5 ⁇ g / m 3 , 4-vinylcyclohexene content is 0.6 ⁇ g / m 3 , 1,3- is not detected Butadiene release, in line with EU standards.
  • the total removal rate is greater than 99%, of which the release amount of 2,4-toluenediamine is 2.0 ⁇ g / m 3 , and the content of 4,4'-diaminodiphenylmethane is 1.8 ⁇ g / m 3 , in line with EU standards.
  • the total removal rate is greater than 99%, of which the release amount of 2,4-toluenediamine is 1.2 ⁇ g / m 3 , and the content of 4,4'-diaminodiphenylmethane is 1.0 ⁇ g / m 3 , in line with EU standards.
  • the headspace gas chromatography-mass spectrometry (HS-GC-MS) and the environmental chamber method were used to analyze and test the residual volatile organic compounds in the devolatilized polyurethane foam, and the total volatile organic compound emissions in 24 hours were 20 ⁇ g / m 3 , in line with relevant national standards and EU standards, the total removal rate is greater than 99%, of which the release amount of 2,4-toluenediamine is 0.9 ⁇ g / m 3 , and the content of 4,4'-diaminodiphenylmethane is 0.8 ⁇ g / m 3 , in line with EU standards.
  • the total removal rate is greater than 99%, of which the release amount of 2,4-toluenediamine is 0.6 ⁇ g / m 3 , and the content of 4,4'-diaminodiphenylmethane is 0.5 ⁇ g / m 3 , in line with EU standards.
  • the total removal rate is greater than 99%, of which the release amount of 2,4-toluenediamine is 1.2 ⁇ g / m 3 , and the content of 4,4'-diaminodiphenylmethane is 0.8 ⁇ g / m 3 , in line with EU standards.

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  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polyurethanes Or Polyureas (AREA)
PCT/CN2019/077409 2018-11-16 2019-03-08 一种用超/亚临界流体脱除海绵中挥发性有机物的方法 Ceased WO2020098184A1 (zh)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2021524205A JP7248253B2 (ja) 2018-11-16 2019-03-08 超臨界/亜臨界流体を用いたスポンジ中の揮発性有機物の除去方法
EP19884606.5A EP3878899B1 (en) 2018-11-16 2019-03-08 Method for using super/subcritical fluid to remove volatile compounds from foam
US17/321,463 US20210269615A1 (en) 2018-11-16 2021-05-16 Method for Removing Volatile Organic Compounds from Sponge by Using Supercritical or Subcritical Fluid

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CN201811368036.XA CN109575354B (zh) 2018-11-16 2018-11-16 一种用超/亚临界流体脱除海绵中挥发性有机物的方法
CN201811368036.X 2018-11-16

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US17/321,463 Continuation US20210269615A1 (en) 2018-11-16 2021-05-16 Method for Removing Volatile Organic Compounds from Sponge by Using Supercritical or Subcritical Fluid

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CN111607022B (zh) * 2020-06-11 2022-08-02 黄河三角洲京博化工研究院有限公司 一种反式丁戊橡胶的脱挥方法
CN112590264A (zh) * 2020-10-30 2021-04-02 佛吉亚(柳州)汽车座椅有限公司 一种降低汽车座椅海绵voc的方法
CN113999332B (zh) * 2021-11-17 2024-05-17 华东理工大学 一种超临界二氧化碳辅助周期性脱挥工艺及装置
CN115125059B (zh) * 2022-06-15 2024-03-26 南京中科药业有限公司 一种去除灵芝孢子油中脂溶性有害成分的方法

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JP2022506669A (ja) 2022-01-17
US20210269615A1 (en) 2021-09-02
EP3878899A4 (en) 2022-01-12
CN109575354A (zh) 2019-04-05
CN109575354B (zh) 2022-12-23
CN115873300A (zh) 2023-03-31
EP3878899A1 (en) 2021-09-15
EP3878899B1 (en) 2023-05-31
JP7248253B2 (ja) 2023-03-29

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