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Redox polymerizable composition with photolabile transition metal complexes

A polymer composition, transition metal technology, applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, chemical instrument and method, etc., can solve stress accumulation, premature curing, formulation storage Poor stability, etc.

Active Publication Date: 2018-07-31
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 transition metal complexes
  • Redox polymerizable composition with photolabile transition metal complexes
  • Redox polymerizable composition with photolabile transition metal complexes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0273] Amounts of materials are expressed by weight or weight percent ("wt %) unless otherwise indicated.

[0274] Materials used:

[0275] Acetone (EMD Millipore Corporation, Billerica, MA)

[0276] Alumina, powder, < / = 10 μm average particle size (Sigma-Aldrich, St. Louis, MO)

[0277] 3-Amino-3-(2-nitrophenyl)propanoic acid, 98% (Alfa Aesar, Ward Hill, MA)

[0278] Ammonium chloride (EMD Chemicals, Inc. Gibbstown, NJ)

[0279] BENZOFLEX 9-88 plasticizer, Eastman Chemical Co., Kingsport, TN (Eastman Chemical Co., Kingsport, TN)

[0280] Benzyltributylammonium chloride (Sigma-Aldrich, St. Louis, MO)

[0281] BisGMA: 2,2-bis[4-hydroxy-3-methacryloyloxy)propoxyphenyl]propane (Sigma Aldrich, St.Louis, MO) )

[0282] CAB-O-SIL TS720 (Cabot Corporation, Billerica, MA)

[0283] CDCl 3 : Deuterochloroform (Cambridge Isotope Laboratories, Andover, MA)

[0284] CH 2 Cl 2 : Dichloromethane (EMD Millipore Corporation, Billerica, MA)

[0285] CHP: cumene hydroperoxide, 80% ...

preparation example 1

[0322] Preparation Example 1 (PE-1): Copper Complex

[0323] The copper metal complexes specified are based on "A Photolabile Ligand for Light-Activated Release of Caged Copper" by Ciesienski, K.L, Haas, K.L., Dickens, M.G., Tesema, Y.T., Franz, K.J. J.Am.Chem.Soc Preparation .

[0324]

preparation example 2

[0325] Preparation Example 2 (PE-2): Copper Complex

[0326] The copper metal complex is based on "Development of Next-generation Photolabile Cages with Improved CopperBinding Properties" published by Ciesienski, K.L, Haas, K.L., Franz, K.J. Dalton Trans.2010, vol.39, pages 9538-9546 ("has Development of next-generation photolabile cages with improved copper-binding properties", Acta Dalton, 2010, Vol. 39, pp. 9538-9546) preparation.

[0327]

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PUM

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Abstract

Polymerizable compositions comprising a redox initiator system is disclosed. The redox initiator system comprises a photolabile transition metal complex 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 method for initiating the curing of acrylate, methacrylate, and other vinyl resins, including adhesives and dental formulations. Redox-initiated curing often has advantages over photo-initiated curing, including improved depth of cure and slow stress build-up 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 achieve full cure and obtain the desired physical properties in a short 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] The present disclosure provides a means to overcome these problems by producing "on-demand" redox-initiated cure, in which the transition metal complex of the redox cur...

Claims

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Application Information

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IPC IPC(8): A61K6/083C08F12/36C08F22/10
CPCC08F12/36C08F4/40C08F2/48C08K3/36A61K6/61A61K6/30A61K6/887C08F22/1006C08F222/1025C08L33/08C08L33/10C08F222/102B01J31/1815C08F4/60168
Inventor W·H·莫泽E·M·汤森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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