Dicarboxylic acid compounds, inorganic particles treated with the dicarboxylic acid compounds, and compositions thereof

Patent metadata

Field	Value
Publication number	US-2023339852-A1
Application number	US-202017753993-A
Country	US
Kind code	A1
Filing date	Sep 25, 2020
Priority date	Sep 30, 2019
Publication date	Oct 26, 2023
Grant date	—

Abstract

Described herein is a dicarboxylic acid compound of formula (I): Wherein: R3 comprises an aryl group, R2 is an alkylene group comprising to 6 carbon atoms, n is 0 or 1, R1 is H or CH3, and X is S or NZ, wherein Z is H, an alkyl group comprising to 4 carbon atoms or a phenyl group. Such compounds can be used to modify the surface of inorganic particles. These modified inorganic particles may then be advantageously used in polymerizable resins to increase the refractive index of the resulting composite, while enabling good flow properties of the polymerizable composition

First claim

What is claimed is:

1 . A dicarboxylic acid compound of formula (I)
wherein: R 3 comprises a monovalent aromatic group, R 2 is an alkylene group comprising 1 to 6 carbon atoms, n is 0 or 1, R 1 is H or CH 3 , and X is S or NZ, wherein Z is H, an alkyl group comprising 1 to 4 carbon atoms, or a phenyl group.

2 . The compound of claim 1 , wherein the aryl group comprises at least one of a phenyl, phenoxy, biphenyl, naphthyl, thiophenyl, carbazole, cumyl phenoxyl (bisphenol A), benzyl phenyl, phenoxy phenyl, fluorenyl, thiophenyl benzyl, and dibenzofuran.

3 . The compound according to claim 1 , wherein n is 1 or 2 and R 3 is a phenyl, phenoxy phenyl, cumyl phenoxy, benzyl phenyl, naphthyloxy, benzophenone oxy, fluorenyl, thiophenyl phenyl, diphenyl phenoxy, carbazole, or thionaphtyl group.

4 . The compound according to claim 1 , wherein n is 0 and R 3 is a phenyl, benzyl phenyl, biphenyl, fluorenyl, or naphthyl group.

5 . The compound of claim 1 , wherein the dicarboxylic acid compound is selected from:
.

6 - 11 . (canceled)

12 . A particle composition comprising a surface modified inorganic particle, wherein the surface of an inorganic particle is modified with a plurality of the following groups of Formula II:
Wherein R 3 comprises an aryl group, n is 0 or 1, R 1 is H or CH 3 , and X is S or NZ, wherein Z is H or alkyl group comprising 1 to 4 carbon atoms or a phenyl group
.

13 - 16 . (canceled)

17 . The particle composition of claim 12 , wherein the groups of Formula II are selected from:
.

18 - 21 . (canceled)

22 . The particle composition of claim 12 , wherein the inorganic particle has an average diameter of at least 5 nm and at most 50 nm.

23 - 24 . (canceled)

25 . A particle composition comprising a reaction product of an inorganic particle and the compound according to claim 1 .

26 . The particle composition of claim 25 , wherein the inorganic particle comprises at least one of a metal oxide, and a chalcogenide.

27 . The particle composition of claim 26 , wherein the metal oxide is titanium oxide, zirconium oxide, aluminum oxide, hafnium oxide, cerium oxide, niobium oxide, and combinations thereof.

28 . The particle composition of claim 25 , wherein the chalcogenide is zinc sulfide.

29 . The particle composition of claim 25 , wherein the inorganic particle has an average diameter of at least 2 nm and at most 1 micron.

30 . The particle composition of claim 24 , wherein at least 10% by weight of the compound according to Formula I is used versus the weight of the inorganic particle.

31 . A polymerizable composition comprising: the particle composition of claim 12 , and a monofunctional aromatic monomer.

32 . (canceled)

33 . The polymerizable composition of claim 31 , wherein the monofunctional aromatic monomer comprises at least one of a phenyl, phenoxy, biphenyl, naphthyl, thiophenyl, carbazole, cumyl phenoxyl (bisphenol A), benzylphenyl, phenoxy phenyl, fluorenyl, thiophenylphenyl, and dibenzofuran.

34 . The polymerizable composition of claim 33 , wherein the aromatic group of the monofunctional aromatic monomer is the same as the aryl group of R 3 .

35 - 41 . (canceled)

42 . The polymerizable composition of claim 31 , wherein the polymerizable composition has a viscosity of less than 30 cP at 60° C.

43 . (canceled)

44 . An optical article comprising the reaction product of the polymerizable composition according to claim 31 .

Assignees

• 3M Innovative Properties Company

Inventors

• Armstrong Paul B
• Anim-Addo Jonathan A
• Hunt Bryan V
• Schwartz Evan L

Classifications

• C09C1/3669

  Treatment with low-molecular organic compounds · CPC title

• C09C1/00

  Treatment of specific inorganic materials other than fibrous fillers (tenebrescent materials C09K9/00; luminescent materials C09K11/00); Preparation of carbon black · CPC title

• C07C323/52 Primary

  the carbon skeleton being acyclic and saturated · CPC title

• C07D307/91

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• C09C1/04

  Compounds of zinc {(C09C1/0003, C09C1/0009, C09C1/0015, C09C1/0078 take precedence)} · CPC title