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Using organic photoredox catalysts to achieve metal free photoregulated controlled radical polymerization

A photo-oxidation and catalyst technology, applied in the field of controlled radical polymerization using organic photo-redox catalysts to achieve metal-free photo-regulation, can solve problems such as limited practicability, achieve macromonomer tolerance, and accurately control molecular weight and molecular weight The effect of distribution

Inactive Publication Date: 2018-03-06
DOW GLOBAL TECH LLC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of expensive Ir-based catalysts limits the practicality of this system and its use in a variety of applications such as electronic materials.

Method used

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  • Using organic photoredox catalysts to achieve metal free photoregulated controlled radical polymerization
  • Using organic photoredox catalysts to achieve metal free photoregulated controlled radical polymerization
  • Using organic photoredox catalysts to achieve metal free photoregulated controlled radical polymerization

Examples

Experimental program
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Embodiment 2

[0050] Embodiment 2 encompasses the photoredox catalyst of embodiment 1 wherein each Z is R 13 ,-B-(A) 2 ,-B-(R 13 ) 2 、-B(A)(R 13 ), -NH-(A), -N-(A) 2 , -NH-(R 13 ), -N-(R 13 ) 2 、-N(A)(R 13 ), -Si-(R 13 ) 3 , -SiH(R 13 ) 2 , -SiH 2 (R 13 ), -SiH(A) 2 , -SiH 2 (A), -Si(A) 3 , -Si(A) 2 (R 13 ), -Si(A)(R 13 ) 2 or -SiH(A)(R 13 ). Specifically, in Example 2, each Z is R 13 ,-B-(R 13 ) 2 , -NH-(R 13 ), -N-(R 13 ) 2 , -Si-(R 13 ) 3 , -SiH(R 13 ) 2 or -SiH 2 (R 13 ). Specifically, in Example 2, each Z is R 13 ,-B-(A) 2 、-B(A)(R 13 ), -NH-(A), -N-(A) 2 、-N(A)(R 13 ), -SiH(A) 2 , -SiH 2 (A), -Si(A) 3 , -Si(A) 2 (R 13 ), -Si(A)(R 13 ) 2 or -SiH(A)(R 13 ). Specifically, in Example 2, each Z is R 13 ,-B-(A) 2 ,-B-(R 13 ) 2 , -NH-(A), -N-(A) 2 , -NH-(R 13 ), -N-(R 13 ) 2 , -Si-(R 13 ) 3 , -SiH(R 13 ) 2 , -Si(A)(R 13 ) 2 or -SiH(A)(R 13 ). Embodiment 3 covers the photoredox catalyst of embodiment 1 wherein each Z is R 13 ,-B...

Embodiment 8

[0053] Specific compounds of Example 8 include those of Example 9, i.e., wherein Y is O, S, NR 14 or C(R 14 ) 2 photoredox catalyst. In embodiment 10, the present disclosure provides the photoredox catalyst of embodiment 8 or 9, wherein Y is O, S or NR 14 . In embodiment 11, the present disclosure provides the photoredox catalyst of embodiment 8 or 9, wherein Y is O or S. In embodiment 12, the present disclosure provides the photoredox catalyst of embodiment 8 or 9, wherein Y is S. In embodiment 13, the disclosure provides the photoredox catalyst of embodiment 8 or 9, wherein Y is C(R 14) 2 . Embodiment 14 covers the photoredox catalyst of embodiment 8, wherein Y is absent.

Embodiment 15

[0054] Embodiment 15 encompasses the photoredox catalyst of any one of embodiments 8 to 14, wherein o and q are independently zero.

[0055] In embodiment 16, the present disclosure provides the photoredox catalyst of any one of embodiments 8-14, wherein at least one of o and q is 1. Embodiment 17 covers the photoredox catalyst of embodiment 16, wherein R 11 and R 12 independently selected from the group consisting of hydrogen, halogen, cyano, hydroxyl, amino, mono(C 1 -C 20 ) Alkylamino or two (C 1 -C 20 ) Alkylamino, C 1 -C 6 Alkyl and C 1 -C 6 alkoxy. Specifically, in Example 17, R 11 and R 12 independently selected from the group consisting of hydrogen, halogen, hydroxy, amino, mono(C 1 -C 20 ) Alkylamino or two (C 1 -C 20 ) Alkylamino, C 1 -C 6 Alkyl and C 1 -C 6 alkoxy.

[0056] Specific embodiments based on Examples 8 to 17 include those of Example 18, i.e., wherein R 13 for C 1 -C 20 Alkyl, -C(O)C 1 -C 20 Alkyl, C 3 -C 7 Cycloalkyl, aryl, ary...

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Abstract

Disclosed are meihods for controlled radical polymerization of acrylic monomers using an organic photoredox catalyst, where the polymerization is mediated, as well as regulated, by light.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Application No. 62 / 060,414, filed October 6, 2014, the disclosure of which is incorporated herein by reference in its entirety. technical field [0003] The present disclosure provides methods for controlled free radical polymerization of acrylic and / or styrenic monomers using organic photoredox catalysts, wherein the polymerization is mediated and regulated by light. Background technique [0004] Controlled radical polymerization (CRP), such as nitroxide-mediated polymerization (NMP), reversible-addition-fragmentation chain transfer polymerization (RAFT), and atom transfer radical polymerization (ATRP) have revolutionized the field of polymer chemistry, allowing Synthesis of well-defined macromolecular structures with excellent functional group tolerance. More important may be the method's convenience and mild reaction conditions, which allow non-experts to obtain f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F120/14C08F220/30C08F220/34C08F293/00C08F4/40C08F2/50C08F2/38
CPCC08F2/38C08F2/50C08F4/40C08F120/14C08F220/34C08F293/005C08F220/30
Inventor J·W·克雷默C·J·霍克B·P·福斯N·J·特里特H·斯帕弗克P·G·克拉克J·里德德阿伦尼兹
Owner DOW GLOBAL TECH LLC
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