Dye, filler made therefrom, compositions including the filler, and method of determining degree of cure of such compositions

Patent metadata

Field	Value
Publication number	US-10233307-B2
Application number	US-201415109350-A
Country	US
Kind code	B2
Filing date	Dec 19, 2014
Priority date	Dec 30, 2013
Publication date	Mar 19, 2019
Grant date	Mar 19, 2019

Abstract

A compound represented by formula (I): and a treated filler having the compound on at least a portion of its surface. R is hydrogen or alkyl. X is alkylene, arylalkylene, or alkylarylene, each optionally interrupted by at least one of an ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, or thiourea, with alkylene optionally interrupted by arylene. W is hydroxyl, a sulfonic acid group, a phosphonic acid group, carboxylic acid group, —NHR 1 , epoxy, or —Si(Y) x (Z) 3-x . Y is alkyl, aryl, arylalkylenyl, or alkylarylenyl. Z is halide, hydroxyl, alkoxy aryloxy, acyloxy, polyalkyleneoxy, —O— covalently bonded to the surface of the filler, or —O bonded to another silicon atom, and x is 0 or 1. A composition including the treated filler, a method of making the treated filler, and a method of determining the degree of cure of a curable polymeric resin are also disclosed.

First claim

What is claimed is:

1. A treated filler comprising:
an inorganic filler having on at least a portion of its surface a compound of formula

wherein
R is hydrogen or alkyl;
X is alkylene, arylalkylene, or alkylarylene, wherein alkylene, arylalkylene, and alkylarylene are optionally interrupted by at least one of an ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, or thiourea, and wherein alkylene is optionally interrupted by arylene;
W is —Si(Y) x (Z 1 ) 3-x ;
Y is alkyl, aryl, arylalkylenyl, or alkylarylenyl;
each Z 1 is independently halide, hydroxyl, alkoxy, aryloxy, acyloxy, polyalkyleneoxy, —O— covalently bonded to the surface of the inorganic filler, or —O— bonded to another silicon atom to form a siloxane, wherein alkoxy and acyloxy are optionally substituted by halogen, and wherein aryloxy is optionally substituted by halogen, alkyl, or haloalkyl; and
x is 0 or 1,

and wherein the compound is at least one of covalently bonded, ionically bonded, or hydrogen-bonded to the inorganic filler.

2. The treated filler of claim 1 , wherein the inorganic filler is a siliceous filler, calcium carbonate, or sodium metaborate.

3. The treated filler of claim 1 , wherein W is —Si(Y) x (Z 1 ) 3-x , wherein x is 0, and wherein each Z 1 is independently hydroxyl, alkoxy, —O— covalently bonded to the surface of the inorganic filler, or —O bonded to another silicon atom to form a siloxane.

4. The treated filler of claim 1 , wherein X is alkylene that is optionally interrupted by at least one ether, ester, carbonate, carbamate, or arylene.

5. The treated filler of claim 1 , wherein X is alkylene that is interrupted by —O—C(O)—NH— and optionally interrupted by —O—.

6. The treated filler of claim 1 , wherein R is H.

7. The treated filler of claim 1 , wherein the inorganic filler comprises at least one of alumina, tin oxides, antimony oxides, silica, zirconia, titania, glass, or ceramics.

8. The treated filler of claim 1 , wherein the inorganic filler comprises hollow glass elements.

9. A composition comprising a curable polymeric resin and the treated filler of claim 1 .

10. The composition of claim 9 , further comprising a free radical initiator.

11. The composition of claim 10 , wherein the free-radical initiator is an organic peroxide.

12. The composition of claim 9 , wherein the composition further comprises at least one of styrene monomer, a substituted styrene monomer, an acrylate monomer, or a methacrylate monomer.

13. A method of making the treated filler of claim 1 , the method comprising treating the inorganic filler with the compound represented by formula:

wherein
R is hydrogen or alkyl;
X is alkylene, arylalkylene, or alkylarylene, wherein alkylene, arylalkylene, and alkylarylene are optionally interrupted by at least one of an ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, or thiourea, and wherein alkylene is optionally interrupted by arylene;
W is —Si(Y) x (Z 1 ) 3-x ;
Y is alkyl, aryl, arylalkylenyl, or alkylarylenyl;
each Z 1 is independently halide, hydroxyl, alkoxy, aryloxy, acyloxy, polyalkyleneoxy, —O— covalently bonded to the surface of the inorganic filler, or —O— bonded to another silicon atom to form a siloxane, wherein alkoxy and acyloxy are optionally substituted by halogen, and wherein aryloxy is optionally substituted by halogen, alkyl, or haloalkyl; and
x is 0 or 1.

14. A composition comprising a curable polymeric resin and a treated filler, wherein the curable polymeric resin is curable by free-radical polymerization, wherein the treated filler comprises:
a filler having on at least a portion of its surface a compound of formula

wherein
R is hydrogen or alkyl;
X is alkylene, arylalkylene, or alkylarylene, wherein alkylene, arylalkylene, and alkylarylene are optionally interrupted by at least one of an ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, or thiourea, and wherein alkylene is optionally interrupted by arylene;
W is hydroxyl, a sulfonic acid group, a phosphonic acid group, carboxylic acid group, —NHR 1 , epoxy, or —Si(Y) x (Z 1 ) 3-x ;
R 1 is hydrogen, alkyl, aryl, arylalkylenyl, or alkylarylenyl;
Y is alkyl, aryl, arylalkylenyl, or alkylarylenyl;
each Z 1 is independently halide, hydroxyl, alkoxy, aryloxy, acyloxy, polyalkyleneoxy, —O— covalently bonded to the surface of the filler, or —O— bonded to another silicon atom to form a siloxane, wherein alkoxy and acyloxy are optionally substituted by halogen, and wherein aryloxy is optionally substituted by halogen, alkyl, or haloalkyl; and
x is 0 or 1,

and wherein the compound is at least one of covalently bonded, ionically bonded, or hydrogen-bonded to the filler.

15. The composition of claim 14 , further comprising a free radical initiator.

16. The composition of claim 15 , wherein the free-radical initiator is an organic peroxide.

17. The composition of claim 14 , wherein the composition further comprises at least one of styrene monomer, a substituted styrene monomer, an acrylate monomer, or a methacrylate monomer.

18. The composition of claim 14 , wherein the inorganic filler comprises at least one of alumina, tin oxides, antimony oxides, silica, zirconia, titania, glass, or ceramics.

19. The composition of claim 14 , wherein the inorganic filler is a siliceous filler, calcium carbonate, or sodium metaborate.

20. The composition of claim 14 , wherein X is alkylene that is optionally interrupted by at least one ether, ester, carbonate, carbamate, or arylene.

21. The composition of claim 14 , wherein the inorganic filler comprises hollow glass elements.

22. A method for determining degree of cure of a curable polymeric resin, the method comprising:
providing the composition of claim 15 , wherein the treated filler is present in an amount sufficient to provide the composition with a first absorbance at a wavelength in a range from 400 nanometers to 700 nanometers; and
allowing the composition to cure to provide a cured composition, wherein the cured composition has a second absorbance at the wavelength that is different from the first absorbance.

23. A composition comprising an unsaturated polyester resin and a treated filler, wherein the treated filler comprises:
a filler having on at least a portion of its surface a compound of formula

wherein
R is hydrogen or alkyl;
X is alkylene, arylalkylene, or alkylarylene, wherein alkylene, arylalkylene, and alkylarylene are optionally interrupted by at least one of an ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, or thiourea, and wherein alkylene is optionally interrupted by arylene;
W is hydroxyl, a sulfonic acid group, a phosphonic acid group, carboxylic acid group, —NHR 1 , epoxy, or —Si(Y) x (Z 1 ) 3-x ;
R 1 is hydrogen, alkyl, aryl, arylalkylenyl, or alkylarylenyl;
Y is alkyl, aryl, arylalkylenyl, or alkylary

Assignees

• 3M Innovative Properties Co

Inventors

• Schulz Mark F
• Wendland Michael S

Classifications

• C08K9/04

  Ingredients treated with organic substances {(treated with macromolecular compounds C08K9/08)} · CPC title

• C09C1/021

  Calcium carbonates · CPC title

• C09C1/28

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

• C09B29/0827

  having N(-alkenylene/-alkynylene-CO)(-alkenylene/-alkynylene-CN) · CPC title

• C09B69/008

  Dyes containing a substituent, which contains a silicium atom · CPC title