CN116675701A - Medium-length/short-chain isosorbide-based structured fat plasticizer and preparation method thereof - Google Patents
Medium-length/short-chain isosorbide-based structured fat plasticizer and preparation method thereof Download PDFInfo
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- CN116675701A CN116675701A CN202310658917.XA CN202310658917A CN116675701A CN 116675701 A CN116675701 A CN 116675701A CN 202310658917 A CN202310658917 A CN 202310658917A CN 116675701 A CN116675701 A CN 116675701A
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- fatty acid
- isosorbide
- acid
- chain fatty
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- 229960002479 isosorbide Drugs 0.000 title claims abstract description 36
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 title claims abstract description 33
- 239000004014 plasticizer Substances 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000000194 fatty acid Substances 0.000 claims abstract description 16
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 10
- 229930195729 fatty acid Natural products 0.000 claims abstract description 10
- 150000004666 short chain fatty acids Chemical class 0.000 claims abstract description 7
- 238000005917 acylation reaction Methods 0.000 claims abstract description 6
- 238000005886 esterification reaction Methods 0.000 claims abstract description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 6
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- -1 isosorbide fatty acid Chemical class 0.000 claims description 5
- 238000007670 refining Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 4
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- LJSMGWBQOFWAPJ-UHFFFAOYSA-N 4-methoxy-3-(naphthalen-1-ylmethyl)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CC(CC(O)=O)C(=O)OC)=CC=CC2=C1 LJSMGWBQOFWAPJ-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- OEOIWYCWCDBOPA-UHFFFAOYSA-N 6-methyl-heptanoic acid Chemical compound CC(C)CCCCC(O)=O OEOIWYCWCDBOPA-UHFFFAOYSA-N 0.000 claims description 2
- 235000021314 Palmitic acid Nutrition 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229960002446 octanoic acid Drugs 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 6
- 231100000252 nontoxic Toxicity 0.000 abstract description 4
- 230000003000 nontoxic effect Effects 0.000 abstract description 4
- 239000004597 plastic additive Substances 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 21
- 229920000915 polyvinyl chloride Polymers 0.000 description 11
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 239000008035 bio-based plasticizer Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- BJAJDJDODCWPNS-UHFFFAOYSA-N dotp Chemical compound O=C1N2CCOC2=NC2=C1SC=C2 BJAJDJDODCWPNS-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical class O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 239000008029 phthalate plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 231100000683 possible toxicity Toxicity 0.000 description 1
- 231100000175 potential carcinogenicity Toxicity 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- Y—GENERAL 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W90/00—Enabling technologies or technologies with a potential or indirect contribution to greenhouse gas [GHG] emissions mitigation
- Y02W90/10—Bio-packaging, e.g. packing containers made from renewable resources or bio-plastics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses a medium-length/short-chain isosorbide-based structured fat plasticizer and a preparation method thereof, belonging to the field of plastic additives. The invention adopts isosorbide with aromatic structure, medium-long chain fatty acid and short chain fatty acid to carry out esterification reaction and acylation reaction to prepare the medium-long chain/short chain fatty acid isosorbide structural fat. The modified polyester fiber has the chemical structure and physical and chemical properties similar to those of phthalate plasticizers, and has the characteristics of being renewable, green, nontoxic, biodegradable and the like. The structure is as follows:n=6‑16；m=0‑5。
Description
Technical Field
The invention relates to a medium-long/short-chain isosorbide-based structured fat plasticizer and a preparation method thereof, belonging to the field of plastic additives.
Background
Under the large background of carbon-to-peak carbon neutralization, the replacement of petroleum-based plasticizers by bio-based plasticizers is a trend. Phthalate plasticizers have potential toxicity and carcinogenicity and pose a great threat to human health and ecological environment. The biomass-derived bio-based plasticizer has green, nontoxic and biodegradable properties, and has a wide development prospect.
The medium-length/short-chain fatty acid isosorbide structured fat plasticizer is derived from cellulose, glucose and fat, and has the characteristics of being renewable, green, nontoxic, biodegradable and the like. In contrast, the modified polyamide has a chemical structure and physical and chemical properties similar to those of phthalic plasticizers. Meanwhile, the PVC/PLA composite material has the advantages of designability, good compatibility of PVC and PLA, good mechanical property, low glass transition temperature, good thermal stability, low volatility, low migration, extraction resistance and the like. Therefore, the development of the plasticizer has good practical application value. Li Wenbo, arbitrary, tao Zijun and the like have studied the preparation of isosorbide-based plasticizers and the properties of plasticized PVC (2021 year 4 of engineering plastics application), which are modified by synthesizing isosorbide and pelargonic acid into a novel bio-based plasticizer, namely isosorbide di-n-pelargonate (SDN), and studied the plasticizing effect of green plasticizers and the influence on the properties of blends, but SDN has no designability, cannot meet the different formulation requirements of PVC, and has poor compatibility and migration to PLA. No report is currently available on the medium-long/short chain fatty acid isosorbide structured lipid plasticizers.
Disclosure of Invention
The invention aims to provide a medium-long/short chain fatty acid isosorbide structured fat plasticizer.
In order to achieve the purpose of the invention, the technical scheme is as follows:
the medium-long/short chain fatty acid isosorbide structured lipid plasticizer has the following structure:n＝6-16；m＝0-5。
it is prepared by the following steps:
(1) Adding isosorbide and medium-long chain fatty acid into a reaction kettle, adding a catalyst, and heating under vacuum to perform esterification reaction. And after the reaction is finished, cooling, and determining that the acid value is less than 3 and reaches the end point to obtain the isosorbide mono fatty acid ester. The molar ratio of isosorbide to medium-long chain fatty acid is preferably 1:1. The reaction temperature is preferably 160-190 ℃.
(2) Gradually adding short-chain fatty anhydride into the isosorbide fatty acid ester, adding a catalyst, heating to 120-140 ℃ under vacuum to perform acylation reaction, cooling after the reaction is finished, and determining that the acid value is less than 3 as an end point. Filtering, washing, distilling and refining the obtained crude product. The molar ratio of isosorbide monofatty acid ester to short chain fatty acid anhydride is preferably 1:1; the reaction temperature is preferably 130 ℃.
The catalyst is one or more of tetrabutyl phthalate, benzenesulfonic acid, phosphoric acid, phosphotungstates and the like.
The medium-long chain fatty acid is C8-18 saturated fatty acid, preferably: octanoic acid, isooctanoic acid, decanoic acid, lauric acid, palmitic acid, epoxidized oleic acid, stearic acid, and the like.
The short-chain fatty acid anhydride is C2-7 saturated fatty acid anhydride, preferably acetic anhydride, butyric anhydride, valeric anhydride or heptanoic anhydride, etc.
The invention has the advantages that: the plasticizer is derived from biomass, and has the characteristics of being renewable, green, nontoxic, biodegradable and the like. Has similar chemical structure and physical and chemical properties as phthalate plasticizer.
Drawings
FIG. 1 is a graph showing the decomposition temperature of PVC test pieces incorporating different plasticizers;
FIG. 2 shows the migration of plasticizers in 95% ethanol by mass for various PVC test pieces;
FIG. 3 is a bar graph showing the volatilization loss rate of different plasticizers in PVC test pieces as a function of time;
fig. 4 shows the migration of plasticizers in 95% ethanol by mass in different PLA test strips:
FIG. 5 is a bar graph of the rate of volatilization loss of various plasticizers in PLA test strips versus time.
Detailed Description
For a better illustration of the invention, the following are given by way of example:
example 1
(1) Adding isosorbide and octanoic acid into a reaction kettle in a molar ratio of 1:1, adding a phosphotungstate catalyst, and heating to 160 ℃ under vacuum to perform esterification reaction. After 4-5h of reaction, cooling to 60 ℃, and determining that the acid value is less than 3 and reaches the end point to obtain the isosorbide mono-fatty acid ester.
(2) Acetic anhydride is gradually added into the isosorbide mono-fatty acid ester according to the molar ratio of 1:1, meanwhile, a phosphotungstic acid salt catalyst is added, the mixture is heated to 130 ℃ under vacuum to carry out acylation reaction for 2 hours, the temperature is reduced to 60 ℃ after the reaction is finished, and the acid value is measured to be less than 3. Filtering, washing, distilling and refining the obtained crude product.
Example 2
(1) Adding isosorbide and lauric acid into a reaction kettle in a molar ratio of 1:1, adding a benzenesulfonic acid catalyst, and heating to 180 ℃ under vacuum to perform esterification reaction. After 4-5h of reaction, cooling to 60 ℃, and determining that the acid value is less than 3 and reaches the end point to obtain the isosorbide mono-fatty acid ester.
(2) And gradually adding the butyric anhydride into the isosorbide mono-fatty acid ester according to the molar ratio of 1:1, adding a benzenesulfonic acid catalyst, heating to 130 ℃ under vacuum for acylation reaction for 2 hours, cooling to 60 ℃ after the reaction is finished, and determining that the acid value is less than 3 as an end point. Filtering, washing, distilling and refining the obtained crude product.
Example 3
(1) Adding isosorbide and epoxidized oleic acid into a reaction kettle in a molar ratio of 1:1, adding a benzenesulfonic acid catalyst, and heating to 170 ℃ under vacuum to perform esterification reaction. After 4-5h of reaction, cooling to 60 ℃, and determining that the acid value is less than 3 and reaches the end point to obtain the isosorbide mono-fatty acid ester.
(2) And gradually adding heptanoic anhydride into the isosorbide mono-fatty acid ester according to the molar ratio of 1:1, adding a benzenesulfonic acid catalyst, heating to 130 ℃ under vacuum for acylation reaction for 2 hours, cooling to 60 ℃ after the reaction is finished, and determining that the acid value is less than 3 as an end point. Filtering, washing, distilling and refining the obtained crude product.
Application example 1
The plasticizer prepared in the above example is abbreviated as ISP, and is applied to PVC, and the performance test is as follows:
1. ISP decomposition temperature is highest compared with DOP, DOTP, TBC, ATBC, etc., and has good thermal stability, as shown in figure 1 and table 1.
The decomposition temperatures of the PVC test pieces to which the different plasticizers were added are shown in the following table:
TABLE 1
2. According to EU food grade test rule food (EU) No1020116112, the mobility test of PVC test pieces added with different plasticizers (ISP, DOP, DOTP TBC, ATBC) shows that: in the 95% ethanol solution by mass, ISP has smaller mobility than DOP, DOTP, TBC, ATBC, etc., as shown in figure 2.
3. The volatilization loss rate of the PVC test pieces added with different plasticizers (ISP, DOP, TBC, ATBC) is tested according to the activated carbon method in HG/T4458-2012, and the volatilization loss rate of the ISP test pieces is obviously lower than that of the test pieces of other products, as shown in figure 3.
4. Mechanical strength test of PVC test pieces with different plasticizers:
application example 2
Application in PLA:
1. mobility test experiments were performed on PLA test pieces (plasticizer addition amount 20%) according to EU food grade test rule food (EU) No1020116112, and the results show that ISP test pieces have smaller mobility compared to conventional plasticizer ESO, TBC, ATBC and the like. Thus demonstrating the good compatibility of ISP with PLA materials, see FIG. 4.
2. The volatile loss rate of the test pieces of PLA added with different plasticizers (ISP, ESO, TBC, ATBC) was tested according to the activated carbon method in HG/T4458-2012, and the volatile loss rate of the test pieces of ISP was significantly lower than that of the test pieces of other products, as shown in FIG. 5.
Claims (3)
1. An isosorbide-based plasticizer, characterized in that: the plasticizer is medium-long/short chain fatty acid isosorbide structural fat, and the molecular structural formula is as follows:
n=6-16；m=0-5。
2. a process for preparing the isosorbide-based plasticizer of claim 1, characterized by the steps of:
(1) Adding isosorbide and medium-long chain fatty acid into a reaction kettle, adding a catalyst, heating to 140-190 ℃ under vacuum to perform esterification reaction, cooling after the reaction is finished, and determining that the acid value is less than 3 to reach the end point to obtain isosorbide fatty acid monoester; the molar ratio of the isosorbide to the medium-long chain fatty acid is 1:1;
(2) Gradually adding short-chain fatty acid anhydride into the isosorbide fatty acid monoester, simultaneously adding a catalyst, heating to 120-140 ℃ under vacuum to perform acylation reaction, cooling after the reaction is finished, and determining that the acid value is less than 3 as an end point; filtering, washing, distilling and refining the obtained crude product; the molar ratio of the isosorbide mono fatty acid ester to the short chain fatty acid anhydride is 1:1;
the catalyst is one or more of tetrabutyl phthalate, benzenesulfonic acid, phosphoric acid and phosphotungstates;
the medium-long chain fatty acid is C8-18 saturated fatty acid;
the short-chain fatty acid anhydride is C2-7 saturated fatty acid anhydride.
3. The method of preparing an isosorbide-based plasticizer according to claim 2, wherein the medium-long chain fatty acid is selected from the group consisting of caprylic acid, iso-caprylic acid, capric acid, lauric acid, palmitic acid, epoxidized oleic acid, and stearic acid; the short chain fatty anhydride is selected from acetic anhydride, butyric anhydride, valeric anhydride or heptanoic anhydride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310658917.XA CN116675701A (en) | 2023-06-05 | 2023-06-05 | Medium-length/short-chain isosorbide-based structured fat plasticizer and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310658917.XA CN116675701A (en) | 2023-06-05 | 2023-06-05 | Medium-length/short-chain isosorbide-based structured fat plasticizer and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116675701A true CN116675701A (en) | 2023-09-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310658917.XA Pending CN116675701A (en) | 2023-06-05 | 2023-06-05 | Medium-length/short-chain isosorbide-based structured fat plasticizer and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116675701A (en) |
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2023
- 2023-06-05 CN CN202310658917.XA patent/CN116675701A/en active Pending
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