Polymeric material and methods of making using controlled radical initiators

• US 10,400,055 B2
• Filed: 06/27/2017
• Issued: 09/03/2019
• Est. Priority Date: 07/11/2016
• Status: Active Grant

• Current Assignee: Solventum Intellectual Properties Company (Solventum Corp.)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Griesgraber, George W., Roscoe, Stephen B., Lee, Hae-Seung Harry, Yurt, Serkan, Chatterjee, Joon, Fansler, Duane D., Gryska, Stefan H., Gaddam, Babu N., Lewandowski, Kevin M., Battiste, John L.
• Primary Examiner(s): Whiteley, Jessica
• Application Number:
  US16/314,760
• Publication Number:
  US 20190153142A1
• Time in Patent Office: 798 Days
• Field of Search: 522 55, 522 49, 522 6, 522 1, 522 71, 522189, 522184, 520 1
• CPC Class Codes: C08F 2/38 Polymerisation using regulators, e.g. chain terminating agents , e.g. telomerisation
• CPC Class Codes: C08F 2/48 by ultraviolet or visible light
• CPC Class Codes: C08F 2/50 with sensitising agents
• CPC Class Codes: C08F 220/10 Esters
• CPC Class Codes: C08F 220/14 Methyl esters , e.g. methyl (meth)acrylate
• CPC Class Codes: C08F 220/1804 C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
• CPC Class Codes: C08F 220/1808 C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
• CPC Class Codes: C08F 220/281 and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
• CPC Class Codes: C08F 2438/03 Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
• CPC Class Codes: C08F 293/005 using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
• CPC Class Codes: C08F 297/023 using a coupling agent
• CPC Class Codes: C08F 297/026 polymerising acrylic acid, methacrylic acid or derivatives thereof

Abstract

Controlled radical initiators, reaction mixtures containing the controlled radical initiators and various ethylenically unsaturated monomers, and polymeric materials formed from the reaction mixtures are provided. The controlled radical initiators are bis-dithiocarbamate or bis-dithiocarbonate compounds with a single carbon atom between the two dithiocarbamate or dithiocarbonate groups. Polymeric materials such as homopolymers, random copolymers, and block copolymers can be prepared using the controlled radical initiators.

Claims

1. A polymeric material of Formula (I-5)

2. The polymeric material of claim 1, wherein y is equal to z.

3. The polymeric material of claim 1, wherein the polymeric material of Formula (I-5) is of Formula (II-1)

4. The polymeric material of claim 1, wherein the polymeric material of Formula (I-5) is of Formula (III-1)

5. The polymeric material of claim 1, wherein the polymeric material of Formula (I-5) is of Formula (IV-1)

6. The polymeric material of claim 1, wherein the polymeric material is not crosslinked.

7. A method of making a polymeric material, the method comprising:

a) providing a photoinitiator of Formula (V-3)

8. The method of claim 7, further comprising:

d) preparing a second reaction mixture comprising the first polymeric material of Formula (II-1) and a second monomer composition different than the first monomer composition, the second monomer composition comprising at least one monomer having a single ethylenically unsaturated group; and

e) forming a second polymeric material of Formula (III-1)

9. The method of claim 8, further comprising:

f) preparing a third reaction mixture comprising the second polymeric material of Formula (III-1) and a third monomer composition different than the second monomer composition, the third monomer composition comprising at least one monomer having a single ethylenically unsaturated group; and

g) forming a third polymeric material of Formula (IV-1)

10. The method of claim 7, wherein the first polymeric material, the second polymeric material, the third polymeric material, or a combination thereof are not crosslinked.

11. A first reaction mixture comprising:

a) a photoinitiator of Formula (V-3)

12. The first reaction mixture of claim 11, wherein the first monomer composition is free of a monomer having more than one ethylenically unsaturated group.

13. A second reaction mixture comprising:

a) a polymeric material of Formula (II-1)

14. The second reaction mixture of claim 13, wherein the second monomer and the second monomer compositions are free of a monomer having more than one ethylenically unsaturated group.

15. A third reaction mixture comprising:

a) a polymeric material of Formula (III-1)