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Norbornene-ester derivatives, their preparation and use

A technology for norbornene and derivatives, applied in the field of norbornene-ester derivatives, can solve the problems of endocrine disrupting, carcinogenic mutation-induced toxicity and reproductive toxicity, etc.

Inactive Publication Date: 2015-08-19
SANGMYUNG UNIV SEOUL IND ACAD COOP FOUND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the three phthalate plasticizers including DOP, DBP and BBP are suspected of being endocrine disrupting
In 2005, the European Committee on Toxicity, Environmental Toxicity and Environmental Sciences has proven that phthalate plasticizers are carcinogenic, mutagenic and reproductive toxic, so their use is banned

Method used

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  • Norbornene-ester derivatives, their preparation and use
  • Norbornene-ester derivatives, their preparation and use
  • Norbornene-ester derivatives, their preparation and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Using 500ml of dichloromethane (CH 2 Cl 2 ), 0.04 moles (5.33lg, the amount of which is 10 mole% of diacrylate) aluminum chloride (AlCl 3 ), 0.40 moles (90.5 g) of 1,6-hexanediol diacrylate, and 1.6 moles (105.8 g) of cyclopentadiene were reacted for 2 hours. The reaction product was washed with brine and dehydrated. To remove the solvent and by-products (ie, dicyclopentadiene), wash filtration was performed with methanol and hexane. The resulting product was vacuum-dried for about 12 hours or more, whereby 0.377 moles (135 g) of 1,6-hexanediol bis(5-norbornene-2-carboxylate) were obtained as Norbornene-ester derivatives. The NMR of this compound is shown below.

[0052] 1 H-NMRδ(ppm):5.87-6.15(4H,m),3.99(4H,m),2.86-3.16(6H,m),1.33-1.64(16H,m)

Embodiment 2

[0054] This example was carried out according to the method of Example 1, except that 0.30 moles (59.5 g) of 1,3-butanediol diacrylate was used instead of 1,6-hexanediol diacrylate in Example 1 ester; the amount of cyclopentadiene is 1.2 moles (79.3g), which is equivalent to 4 times the moles of diacrylate; aluminum chloride (AlCl 3 ) is used in an amount of 0.03 mol (4.00 g), which is equivalent to 10 mol% of the amount of diacrylate. Finally, 0.26 mol (85.9 g) of 1,3-butanediol bis(5-norbornene-2-carboxylate) was obtained as a norbornene-ester derivative represented by Chemical Formula 1. The NMR of this compound is shown below.

[0055] 1 H-NMRδ(ppm):5.89-6.16(4H,m),4.92(1H,m),3.16,2.98,2.86(6H,m),1.19-1.88(13H,m)

Embodiment 3

[0057] Carry out this embodiment according to the method for embodiment 1, difference is: use the diethylene glycol diacrylate of 0.30 moles (64.3g) to replace the 1,6-hexanediol diacrylate in embodiment 1; The amount of diene is 1.2 moles (79.3g), which is equivalent to 4 times the moles of diacrylate; aluminum chloride (AlCl 3 ) is used in an amount of 0.03 mol (4.00 g), which is equivalent to 10 mol% of the amount of diacrylate. Finally, 0.24 mol (83.1 g) of diethylene glycol bis(5-norbornene-2-carboxylate) was obtained as a norbornene-ester derivative represented by Chemical Formula 1. The NMR of this compound is shown below.

[0058] 1 H-NMRδ(ppm):5.91-6.15(4H,m),4.13(4H,m),3.66(4H,m),3.18,3.00,2.87(6H,m),1.27-1.41(8H,m)

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Abstract

The present invention relates to norbornene-ester derivatives, their preparation methods, and their uses. Said compounds can replace phthalate plasticizers as plasticizers.

Description

technical field [0001] The present invention relates to norbornene-ester derivatives, their preparation methods and uses. Background technique [0002] Norbornene is a bridged six-membered carbon ring with one double bond on one side, and norbornene exhibits high reactivity due to its double bond, so it can be used not only in applications such as optical fibers, CD-ROMs, and optical lenses and other optical materials, can also be applied to modified polymeric materials, etc., so it is considered to be highly useful. In particular, polynorbornene produced by polymerizing norbornene is a known shape-memory polymer that is effectively used for medical devices, vehicle parts, and household goods. [0003] In addition, plasticizers added to products are liquid or solid materials that lower the melting temperature and melt viscosity of rubber and plastic, thereby improving processability and flexibility. Good plasticizers have low volatility, stability under hot and cold condit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/743C07C69/74C08K5/10
CPCC07C67/347C07C69/753C08K5/103C07C2602/42C08K5/12C08L21/00C07C69/757C07C69/74C07C67/28C08K5/10
Inventor 姜柱熙禹济玩朴容成吴贤哲朴俊星金一文尹大禧高祥真金永云金南均郑根雨
Owner SANGMYUNG UNIV SEOUL IND ACAD COOP FOUND
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