Redox polymerizable composition with photolabile reducing agents

A polymeric composition, photo-instability technology, applied in organic chemistry, chemical/physical process, catalyst activation/preparation, etc., can solve problems such as stress accumulation, poor storage stability of formulations, premature curing, etc.

Active Publication Date: 2018-08-03
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, if the reactivity is too high, problems such as premature curing, stress buildup, and poor shelf stability of the formulation may be encountered

Method used

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  • Redox polymerizable composition with photolabile reducing agents
  • Redox polymerizable composition with photolabile reducing agents
  • Redox polymerizable composition with photolabile reducing agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0288] All amounts and percentages are by weight unless otherwise indicated.

[0289] materials used :

[0290] Acetone (EMD Millipore Corporation, Billerica, MA)

[0291] Acm: Acrylamide (Zibo Xinye Chemical Company, Zibo, China)

[0292] Ammonium chloride (EMD Chemicals, Inc. Gibbstown, NJ)

[0293] L-Ascorbic acid (Alfa Aesar, Ward Hill, MA)

[0294] L-Ascorbic acid-6-palmitate (Alfa Aesar, Ward Hill, MA)

[0295] BA: n-butyl acrylate (BASF Corporation, Florham Park, NJ)

[0296] BAYMOD 35.42 (Lanxess, Cologne, Germany)

[0297] BDGMA: Butyldiethylene glycol methacrylate (Evonik Industries, Marl, Germany)

[0298] BENZOFLEX 9-88, Plasticizer (Eastman Chemical Co., Kingsport, TN)

[0299] Benzyltributylammonium chloride (Sigma-Aldrich, St. Louis, MO)

[0300] BisGMA: 2,2-bis[4-hydroxy-3-methacryloyloxy)propoxyphenyl]propane (Sigma Aldrich, St.Louis, MO) )

[0301] 4-Bromomethyl-6,7-dimethoxycoumarin (Sigma-Aldrich, St. Louis, MO)

[0302] CAB-O-SIL TS720 (Cabot Co...

preparation example 1

[0375] Preparation Example 1 (PE-1): Synthesis of 5,6-O-isopropylidene-L-ascorbic acid (p-AA)

[0376] The material was prepared according to previous literature (Bioorg. Med. Chem. 2003, vol. 11, 827 ("Bioorganic Medical Chemistry", 2003, Vol. 11, p. 827)). To a suspension of L-ascorbic acid (20.0 g, 114 mmol) in acetone (200 mL) was added 2,2-dimethoxypropane (20.4 g, 196 mmol) and 10-camphorsulfonic acid (1.32 g, 5.68 mmol). The resulting mixture was stirred overnight at room temperature. To the resulting slurry was added about 0.6 g of triethylamine. A portion of hexane was added to the mixture and the white precipitate was collected via vacuum filtration and washed with additional hexane. The material was dried under vacuum to afford the desired product (21.0 g, 86% yield). 1 H NMR was consistent with the desired product.

[0377]

preparation example 2

[0378] Preparation Example 2 (PE-2): Synthesis of nitrobenzyl-protected p-AA

[0379] Potassium carbonate (3.03 g, 21.9 mmol) was added to a solution of p-AA (4.73 g, 21.9 mmol) in 40 ml 1:1 THF / DMSO. The resulting mixture was allowed to stir for 30 min. A solution of 2-nitrobenzyl bromide (4.73 g, 21.9 mmol) in 20 mL of 1:1 THF / DMSO was then added dropwise via addition funnel over 10 min. The resulting mixture was allowed to stir overnight under nitrogen atmosphere, during which time it turned dark orange. After removing THF under reduced pressure, about 200 mL of H 2 O was added to the mixture, then extracted with EtOAc (3x). The combined organic layers were washed with H 2 O(3x) and saturated aqueous NaCl, washed with MgSO 4Dry, filter, and concentrate to a yellow solid. This material was purified via trituration with 2:1 hexanes / EtOAc to afford 4.47 g of the product (58% yield) as a pale yellow solid. 1 H NMR was consistent with the desired product.

[0380]

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Abstract

Polymerizable compositions comprising a redox initiator system is disclosed. The redox initiators comprise a photolabile reducing agent, that photolyzes and initiates the redox cycle. Dental compositions comprising dental resins and the photolabile redox initiator system are also described.

Description

Background technique [0001] Redox reactions represent an important process for initiating the cure of acrylate, methacrylate, and other vinyl-based resins, including adhesives and dental formulations. Redox-initiated curing often has advantages over photo-initiated curing, including improved depth of cure and slow stress buildup during the initial stages of curing. [0002] A major challenge in using redox-initiated systems is to find the optimal balance between stability and reactivity. The reactivity of the redox system needs to be high enough to fully cure and obtain mechanical properties within a short period of time. However, if the reactivity is too high, problems such as premature curing, stress buildup, and poor shelf stability of the formulation may be encountered. Contents of the invention [0003] Applicants provide a method to overcome these problems by producing "on-demand" redox-initiated cure, wherein the reducing agent of the redox-cure initiator system is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F22/10C07D307/62C07D405/10C07D407/14
CPCC07D407/14C07D307/62C09D4/00C07D307/04C08F4/40A61K6/30A61K6/887C08F222/1025C08F220/1804C08F220/1808C08L33/08C08L33/10C09J7/401C07D307/58C08F20/18C08F220/18C08F222/1006C08J9/0023C07D307/33B01J37/12B01J37/16C08K5/1535C08J2333/08C08J2333/10C08F22/1006C07D307/32
Inventor E·M·汤森W·H·莫泽S·R·拉纳德K·S·谢弗M·A·克洛普R·E·贝灵J·D·克拉珀
Owner 3M INNOVATIVE PROPERTIES CO
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