Poly(propylene glycol) diglycidyl ether

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Poly(propylene glycol) diglycidyl ether
Poly(propylene glycol) diglycidyl ether.svg
Names
Other names
Polyoxypropylene diglycidyl ether; PPGDGE
Identifiers
ECHA InfoCard 100.130.913 OOjs UI icon edit-ltr-progressive.svg
Properties
(C3H6O)n.C6H10O3
Molar mass Variable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Poly(propylene glycol) diglycidyl ether (PPGDGE) is an organic chemical in the glycidyl ether family. There are a number of variations depending on the starting molecular weight of the polypropylene glycol. [1] They have the formula (C3H6O)n.C6H10O3 [2] and the IUPAC name is Poly[oxy(methyl-1,2-ethanediyl)],a-(2-oxiranylmethyl)-w-(2-oxiranylmethoxy)- [3] A key use is as a modifier for epoxy resins as a reactive diluent and flexibilizer. [4] [5] It is REACH registered. [6]

Contents

Manufacturing

The product is made by taking polypropylene glycol and epichlorohydrin and reacting in the presence of a Lewis acid catalyst to form a halohydrin. The next step is dehydrochlorination with sodium hydroxide. This forms the diglycidyl ether. Waste products are sodium chloride, water and excess sodium hydroxide (alkaline brine). [7] [8] One of the quality control tests would involve measuring the epoxy value by determination of the epoxy equivalent weight.

Use

The molecule has 2 oxirane functionalities, and so a key use is modifying and reducing the viscosity of epoxy resins. [9] [10] These reactive diluent modified epoxy resins may then be further formulated into CASE applications: coatings, [11] adhesives, sealants, and elastomers. It produces epoxy coatings with high impact resistance. [12] The use of the diluent does effect mechanical properties and microstructure of epoxy resins. [13]

Synthesis of waterborne polymers has been a feature with this substance. As the basic building block is propylene oxide, there are 3 carbons per oxygen on the backbone. This confers some degree of water miscibility though not as good as ethylene oxide based molecules. [14] [15]

The material maybe used to produce polymers with shape memory and good thermomechanical properties. [16] In addition, the molecule is used to synthesize other molecules. [17] [18] [19] [20] [21]

Toxicology

The toxicology of the material is reasonably well known. [22]

See also

Further reading

Related Research Articles

<span class="mw-page-title-main">Epoxy</span> Type of material

Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also collectively called epoxy. The IUPAC name for an epoxide group is an oxirane.

<span class="mw-page-title-main">Polypropylene glycol</span> Chemical compound

Polypropylene glycol or polypropylene oxide is the polymer of propylene glycol. Chemically it is a polyether, and, more generally speaking, it's a polyalkylene glycol (PAG) H S Code 3907.2000. The term polypropylene glycol or PPG is reserved for polymer of low- to medium-range molar mass when the nature of the end-group, which is usually a hydroxyl group, still matters. The term "oxide" is used for high-molar-mass polymer when end-groups no longer affect polymer properties. Between 60 and 70% of propylene oxide is converted to polyether polyols by the process called alkoxylation.

<span class="mw-page-title-main">Bisphenol A diglycidyl ether</span> Chemical compound

Bisphenol A diglycidyl ether is an organic compound used as constituent of epoxy resins. The compound is a colorless solid that melts slightly above room temperature.

n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive. It is principally used to reduce the viscosity of epoxy resin systems.

<span class="mw-page-title-main">Reactive diluent</span>

Reactive diluents are substances which reduce the viscosity of a lacquer or resin for processing and become part of the lacquer or coating during its subsequent curing via copolymerization. A non-reactive diluent would be a solvent or plasticizer.

2-Ethylhexyl glycidyl ether is a liquid organic molecule with formula C11H22O2 an industrial chemical used to reduce the viscosity of epoxy resins. These are then used in adhesives, sealants, and paints or coatings. It has the CAS Registry Number of 2461-15-6. It has the IUPAC name of 2-(2-ethylhexoxymethyl)oxirane. It also finds use in other polymer based applications.

<i>o</i>-Cresyl glycidyl ether Chemical compound

o-Cresyl glycidyl ether (ortho-cresyl glycidyl ether, o-CGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether. It has the formula C10H12O2 and the CAS Registry Number 2210-79-9. It is one of a number of glycidyl ethers available commercially that are used to reduce the viscosity of epoxy resins. These are then further used in coatings, sealants, adhesives and elastomers.

Neopentyl glycol diglycidyl ether (NPGDGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has the formula C11H20O4 and the CAS registry number of 17557-23-2. It has two oxirane groups per molecule. Its principle use is in modifying epoxy resins.

1,4-Butanediol diglycidyl ether (B14DODGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction.

1,6-Hexanediol diglycidyl ether is an organic chemical in the glycidyl ether family. It is aliphatic compound that is a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction whilst flexibilizing. It is REACH registered.

1,4-Cyclohexanedimethanol diglycidyl ether is an organic chemical in the glycidyl ether family. It has the formula C14H24O4 and the IUPAC name is 2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane, and the CAS number 14228-73-0. It is It is REACH registered in Europe. It is an industrial chemical and a key use is in the reduction of viscosity of epoxy resin systems functioning as a reactive diluent.

<span class="mw-page-title-main">C12–C14 alcohol glycidyl ether</span> Chemical compound

C12-C14 alcohol glycidyl ether (AGE) is an organic chemical in the glycidyl ether family. It is a mixture of mainly 12 and 14 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction. It has the CAS number 68609-97-2 but the IUPAC name is more complex as it is a mixture and is 2-(dodecoxymethyl)oxirane;2-(tetradecoxymethyl)oxirane;2-(tridecoxymethyl)oxirane. Other names include dodecyl and tetradecyl glycidyl ethers and alkyl (C12-C14) glycidyl ether.

<span class="mw-page-title-main">Trimethylolpropane triglycidyl ether</span> Chemical compound

Trimethylolpropane triglycidyl ether (TMPTGE) is an organic chemical in the glycidyl ether family. It has the formula C15H26O6 and the IUPAC name is 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane, and the CAS number 3454-29-3. It also has another CAS number of 30499-70-8 A key use is as a modifier for epoxy resins as a reactive diluent.

<span class="mw-page-title-main">Castor oil glycidyl ether</span> Chemical compound

Castor oil glycidyl ether is a liquid organic chemical in the glycidyl ether family. It is sometimes called castor oil triglycidyl ether. It has the theoretical formula C66H116O12 and the CAS number 14228-73-0. The IUPAC name is 2,3-bis[[(E)-12-(oxiran-2-ylmethoxy)octadec-9-enoyl]oxy]propyl (E)-12-(oxiran-2-ylmethoxy)octadec-9-enoate. A key use is acting as a modifier for epoxy resins as a reactive diluent that adds flexibility and improved mechanical properties.

<span class="mw-page-title-main">C12–C13 alcohol glycidyl ether</span> Chemical compound

C12-C13 alcohol glycidyl ether is a mixture of organic chemicals in the glycidyl ether family. It is a mixture of mainly 12 and 13 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction. It has the CAS number 120547-52-6.

<span class="mw-page-title-main">Trimethylolethane triglycidyl ether</span> Chemical compound

Trimethylolethane triglycidyl ether (TMETGE) is an organic chemical in the glycidyl ether family. It has the formula C14H24O6 and the IUPAC name is 2-({2-methyl-3-[(oxiran-2-yl)methoxy]-2-{[(oxiran-2-yl)methoxy]methyl}propoxy}methyl)oxirane. The CAS number is 68460-21-9. A key use is as a modifier for epoxy resins as a reactive diluent.

<span class="mw-page-title-main">Diethylene glycol diglycidyl ether</span> Chemical compound

Diethylene glycol diglycidyl ether (DEGDGE) is an organic chemical in the glycidyl ether family with the formula C10H18O5.. The oxirane functionality makes it useful as a reactive diluent for epoxy resin viscosity reduction.

<span class="mw-page-title-main">Diglycidyl resorcinol ether</span> Chemical compound

Diglycidyl resorcinol ether, also called Resorcinol diglycidyl ether (RDGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether. It has the formula C12H14O4 and the CAS Registry Number 101-90-6. It is one of a number of glycidyl ethers available commercially that are used to reduce the viscosity of epoxy resins. These are then further used in coatings, sealants, adhesives and elastomers. It has the CAS Registry Number 101-90-6. It has the IUPAC name 2-[[3-(oxiran-2-ylmethoxy)phenoxy]methyl]oxirane and is registered on TSCA (Toxic Substances Control Act of 1976) as Oxirane, 2,2'-[1,3-phenylenebis(oxymethylene)]bis-. It is REACH registered and on EINECS.

<span class="mw-page-title-main">Phenyl glycidyl ether</span> Chemical compound

Phenyl glycidyl ether, is a liquid aromatic organic chemical in the glycidyl ether class of compounds. It has the formula C9H10O2. It has the CAS Registry Number 122-60-1 and the IUPAC name of 2-(phenoxymethyl)oxirane. A key use is in the viscosity reduction of epoxy resin systems. It is REACH registered and on EINECS under the name 2,3-epoxypropyl phenyl ether.

<span class="mw-page-title-main">Diglycidyl aniline</span> Chemical compound

Diglycidyl aniline is an aromatic organic chemical in the glycidyl compound family. It is used to reduce the viscosity of epoxy resin systems. It has the empirical formula C12H15NO2 and the IUPAC name is N,N-bis(oxiran-2-ylmethyl)aniline. The CAS number is 2095-06-9. It is REACH registered in Europe with the EC number 218-259-5. A key use is in the viscosity reduction of epoxy resin systems functioning as a reactive diluent.

References

  1. ↑ "Poly(propylene glycol) (600) diglycidyl ether". www.polysciences.com. Retrieved 2022-05-17.
  2. ↑ "Polypropylenglycol diglycidyl ether | 26142-30-3". ChemicalBook. Retrieved 2022-05-17.
  3. ↑ "Poly(propylene glycol) diglycidyl ether". Sigma Aldrich.
  4. ↑ Jagtap, Ameya Rajendra; More, Aarti (2022-08-01). "Developments in reactive diluents: a review". Polymer Bulletin. 79 (8): 5667–5708. doi:10.1007/s00289-021-03808-5. ISSN   1436-2449. S2CID   235678040.
  5. ↑ Monte, Salvatore J. (1998), Pritchard, Geoffrey (ed.), "Diluents and viscosity modifiers for epoxy resins", Plastics Additives: An A-Z reference, Polymer Science and Technology Series, Dordrecht: Springer Netherlands, vol. 1, pp. 211–216, doi:10.1007/978-94-011-5862-6_24, ISBN   978-94-011-5862-6, archived from the original on 2022-04-11, retrieved 2022-03-29
  6. ↑ "Substance Information Polypropylene Glycol Diglycidyl Ether- ECHA". echa.europa.eu. Retrieved 2022-05-17.
  7. ↑ Crivello, James V. (2006). "Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization". Journal of Polymer Science Part A: Polymer Chemistry. 44 (21): 6435–6448. Bibcode:2006JPoSA..44.6435C. doi:10.1002/pola.21761. ISSN   0887-624X.
  8. ↑ US 5162547,Roth, Martin; Wolleb, Heinz& Truffer, Marc-Andre,"Process for the preparation of glycidyl ethers",published 1992-11-10, assigned to Ciba-Geigy Corp.
  9. ↑ Zarnitz, Charles. "Flexibilizing modifiers" (PDF). CVC Thermosets.
  10. ↑ Monte, Salvatore J. (1998), Pritchard, Geoffrey (ed.), "Diluents and viscosity modifiers for epoxy resins", Plastics Additives: An A-Z reference, Polymer Science and Technology Series, Dordrecht: Springer Netherlands, vol. 1, pp. 211–216, doi:10.1007/978-94-011-5862-6_24, ISBN   978-94-011-5862-6, archived from the original on 2022-04-11, retrieved 2022-03-29
  11. ↑ WOapplication 2015095994,Shen, Yue; Zhan, Fu& Wu, Yanet al.,"Epoxy resin composition",published 2015-07-02, assigned to Dow Global Technologies LLC
  12. ↑ US 8062468,Finter, Jürgen; Kramer, Andreas& Schulenburg, Jan Olafet al.,"Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins",published 2011-11-22, assigned to Sika Technology AG
  13. ↑ Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali (2019-08-01). "The effect of reactive diluent on mechanical properties and microstructure of epoxy resins". Polymer Bulletin. 76 (8): 3905–3927. doi:10.1007/s00289-018-2577-6. ISSN   1436-2449. S2CID   105389177.
  14. ↑ "US Patent for Water soluble polymers and polymer adducts along with aqueous solutions thereof Patent (Patent # 10,920,011 issued February 16, 2021) - Justia Patents Search". patents.justia.com. Retrieved 2022-05-17.
  15. ↑ Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" pages 36-28, 52-60 Master of Science Thesis April 1997 Imperial College London
  16. ↑ Wei, Kun; Zhu, Guangming; Tang, Yusheng; Tian, Guangming; Xie, Jianqiang (2012-05-01). "Thermomechanical properties of shape-memory hydro-epoxy resin". Smart Materials and Structures. 21 (5): 055022. doi:10.1088/0964-1726/21/5/055022. ISSN   0964-1726. S2CID   136532406.
  17. ↑ Castillejos, Sandra; Cerna, Jorge; Meléndez, Francisco; Castro, María Eugenia; Aguilar, Rocío; Márquez-Beltrán, César; González, Maykel (November 2018). "Bulk Modification of Poly(lactide) (PLA) via Copolymerization with Poly(propylene glycol) Diglycidylether (PPGDGE)". Polymers. 10 (11): 1184. doi: 10.3390/polym10111184 . ISSN   2073-4360. PMC   6290617 . PMID   30961109.
  18. ↑ Huang, Biwu; Huang, Bofen; Du, Guoping; Chen, Weiqing (2008-08-01). "Synthesis of a novel UV-curable prepolymer polypropyleneglycol diglycidyl ether diacrylate". Journal of Wuhan University of Technology-Mater. Sci. Ed. 23 (4): 495–498. doi:10.1007/s11595-006-4495-y. ISSN   1993-0437. S2CID   136731416.
  19. ↑ Li, Yun; You, Yanhong; Huang, Weijia; Yang, Jie (2019-01-01). "Solubilities of CO2 in, densities and kinematic viscosities of poly(propylene glycol) diglycidyl ether and poly(ethylene glycol) monooleate". The Journal of Chemical Thermodynamics. 130: 38–46. doi:10.1016/j.jct.2018.09.031. ISSN   0021-9614. S2CID   105754055.
  20. ↑ Ke, Jiexi; Li, Xiaoyun; Wang, Feng; Jiang, Shuai; Kang, Maoqing; Wang, Junwei; Li, Qifeng; Wang, Zhijie (2017). "Non-isocyanate polyurethane/epoxy hybrid materials with different and controlled architectures prepared from a CO 2 -sourced monomer and epoxy via an environmentally-friendly route". RSC Advances. 7 (46): 28841–28852. doi:10.1039/C7RA04215A. ISSN   2046-2069. S2CID   98934685.
  21. ↑ "Plastification of Polypropylene Glycol Diglycidyl Ether-co-Citric Acid Copolyester on Polylactide". www.cnki.net. doi:10.14135/j.cnki.1006-3080.2017.01.007 . Retrieved 2022-05-17.
  22. ↑ Berdasco, Nancy Anne M.; Waechter, John M. (2012-08-17), Bingham, Eula; Cohrssen, Barbara; Powell, Charles H. (eds.), "Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds", Patty's Toxicology, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. 491–528, doi:10.1002/0471435139.tox083.pub2, ISBN   978-0-471-12547-1 , retrieved 2022-07-28

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