Compositions including a polythiol, an unsaturated compound, and a dye and methods relating to such compositions

Patent metadata

Field	Value
Publication number	US-10745558-B2
Application number	US-201615739485-A
Country	US
Kind code	B2
Filing date	Jun 28, 2016
Priority date	Jun 29, 2015
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

A curable composition having a polythiol; at least one unsaturated compound comprising more than one carbon-carbon double bond, carbon-carbon triple bond, or a combination thereof; and a dye compound represented by formula (I). A crosslinked composition prepared from the curable composition, a method of making an at least partially crosslinked network, a method for indicating curing in a curable composition, and a method of stabilizing a curable composition comprising a polythiol and at least one unsaturated compound comprising more than one carbon-carbon double bond, carbon-carbon triple bond, or a combination thereof are also disclosed. Z is not reactive with the polythiol or unsaturated compound.

First claim

What is claimed is:

1. A curable composition comprising a polythiol; at least one unsaturated compound comprising more than one carbon-carbon double bond that is not part of an aromatic ring, carbon-carbon triple bond, or a combination thereof; and a dye compound represented by formula:

wherein
R is hydrogen or alkyl;
X is alkylene optionally interrupted by —O—;
Y is —O—, —S—, —NR 1 —, —N(R 1 )—C(O)—, —C(O)—N(R 1 )—, —C(O)—O—, S—C(O)—, —O—C(S)—, —C(S)—O—, —S—C(O)—O—, —(R 1 )N—C(O)—O—, —O—C(O)—N(R 1 )—, —(R 1 )N—C(S)—O—, —O—C(S)—N(R 1 )—, —S—C(O)—N(R 1 )—, —(R 1 )N—C(O)—N(R 1 )—, or —(R 1 )N—C(S)—N(R 1 )—;
R 1 is hydrogen, alkyl, aryl, arylalkylenyl, or alkylarylenyl; and
Z is hydrogen, alkyl, aryl, arylalkylenyl, alkylarylenyl, heterocyclyl, or heterocyclylalkylenyl, wherein alkyl, aryl, arylalkylenyl, alkylarylenyl, heterocyclyl, or heterocyclylalkylenyl are unsubstituted or substituted by at least one substituent selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, haloalkyl, haloalkoxy, halogen, nitro, hydroxyl, cyano, amino, alkylamino, dialkylamine, and in the case of alkyl, heterocyclyl, and heterocyclylalkylenyl, oxo;
with the proviso that when Y is —S— or —O—, Z is other than hydrogen, and with the further proviso that Z is not a styrenyl group;
or wherein Y is —O—C(O)— or —O—C(O)—O—, and Z is aryl, arylalkylenyl, alkylarylenyl, heterocyclyl, or heterocyclylalkylenyl, wherein aryl, arylalkylenyl, alkylarylenyl, heterocyclyl, or heterocyclylalkylenyl are unsubstituted or substituted by at least one substituent selected from the group consisting of alkyl, alkoxy, hydroxyalkyl, haloalkyl, haloalkoxy, halogen, nitro, hydroxyl, cyano, amino, alkylamino, dialkylamine, and in the case of heterocyclylalkylenyl, oxo, with the proviso that Z is not a styrenyl group.

2. The curable composition of claim 1 , wherein the polythiol is monomeric.

3. The curable composition of claim 1 , wherein the polythiol is oligomeric or polymeric.

4. The curable composition of claim 1 , wherein the polythiol and the at least one unsaturated compound are at least partially crosslinked to form a polymer network.

5. A method for indicating curing in a curable composition, the method comprising:
providing the curable composition of claim 1 , wherein the dye compound is present in the composition 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 at least partially cure to provide an at least partially cured composition, wherein the at least partially cured composition has a second absorbance at the wavelength that is different from the first absorbance.

6. A curable composition comprising a polythiol; at least one unsaturated compound comprising more than one carbon-carbon double bond that is not part of an aromatic ring; and a dye compound represented by formula:

wherein
R is hydrogen or alkyl;
X is alkylene optionally interrupted by —O—;
Y is —O—C(O)—; and
Z is alkyl.

7. The curable composition of claim 6 , wherein the polythiol is monomeric.

8. The curable composition of claim 6 wherein the polythiol is a polythioether oligomer or polymer or a polysulfide oligomer or polymer.

9. The curable composition of claim 8 , wherein the polythiol is a polythioether oligomer or polymer prepared from components comprising a dithiol and a diene or divinyl ether and optionally a trithiol, triene, or trivinyl ether.

10. The curable composition of claim 6 , wherein X is alkylene.

11. The curable composition of claim 6 , wherein the at least one unsaturated compound comprises a diene, a divinyl ether, or a diallyl ether.

12. The curable composition of claim 6 , wherein the at least one unsaturated compound comprising more than one carbon-carbon double bond comprises a divinyl ether.

13. The curable composition of claim 6 , wherein the at least one unsaturated compound comprises two carbon-carbon double bonds, and wherein the curable composition further comprises a second unsaturated compound comprising three carbon-carbon double bonds.

14. The curable composition of claim 6 , further comprising a free-radical initiator.

15. The curable composition of claim 14 , wherein the free-radical initiator is a photoinitiator.

16. The curable composition of claim 14 , wherein the free-radical initiator is a thermal initiator.

17. The curable composition of claim 6 , further comprising at least one of silica, carbon black, calcium carbonate, aluminum silicate, or lightweight particles having a density of up to 0.7 grams per cubic centimeter.

18. A method of stabilizing a curable composition, the method comprising providing the curable composition of claim 6 , wherein the dye compound is included in an amount sufficient to reduce a viscosity increase of the curable composition relative to a comparative composition that is the same as the curable composition except that it does not contain the dye compound.

19. An at least partially crosslinked polymer network comprising:
a polythiol at least partially crosslinked with at least one unsaturated compound comprising more than one carbon-carbon double bond that is not part of an aromatic ring; and
a dye compound represented by the following formula:

wherein
R is hydrogen or alkyl;
X is alkylene optionally interrupted by —O—;
Y is —O—C(O)—; and
Z is alkyl.

20. A sealant comprising the at least partially crosslinked polymer network of claim 19 .

Assignees

• 3M Innovative Properties Co

Inventors

• Ye Sheng
• Shafer Kathleen S
• Wendland Michael S
• Demoss Susan E
• Zook Jonathan D

Classifications

• C08F291/04 Primary

  on to halogen-containing macromolecules · CPC title

• C08K5/0041

  Optical brightening agents, organic pigments · CPC title

• C08K5/47

  Thiazoles · CPC title

• C08K2003/265

  Calcium, strontium or barium carbonate · CPC title

• C08F222/26

  of unsaturated alcohols {(C08F222/1006 takes precedence)} · CPC title