Mercapto-containing bisanhydrohexitol derivatives and uses thereof

Patent metadata

Field	Value
Publication number	US-9388274-B2
Application number	US-201214364398-A
Country	US
Kind code	B2
Filing date	Dec 7, 2012
Priority date	Dec 16, 2011
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

Bisanhydrohexitol derivatives having terminal mercapto groups are provided. Additionally, curable compositions that include these mercapto-containing bisanhydrohexitol derivatives, cured compositions prepared from the curable compositions, and articles containing the cured compositions are provided. More specifically, the curable compositions are epoxy-based formulations and the mercapto-containing bisanhydrohexitol derivatives function as curing agents for epoxy resins.

First claim

We claim:

1. A compound of Formula (I)
HS-L-Y—O-Q-O—Y-L-SH   (I)

wherein
each Y is independently a single bond or a carbonyl group;
each L is independently an alkylene or heteroalkylene; and
Q is a divalent group of Formula (I-1), Formula (I-2), or Formula (I-3)

2. The compound of claim 1 , wherein the compound is a liquid at 25° C.

3. The compound of claim 1 , wherein the compound of Formula (I) is of Formula (II)
HS-L-(CO)—O-Q-O—(CO)-L-SH   (II).

4. The compound of claim 3 , wherein the compound of Formula (II) is
HS—CH 2 —(CO)—O-Q-O—(CO)—CH 2 —SH,

HS—CH(CH 3 )—(CO)—O-Q-O—(CO)—CH(CH 3 )—SH, or

HS—CH 2 CH 2 —(CO)—O-Q-O—(CO)—CH 2 CH 2 —SH.

5. The compound of claim 1 , wherein the compound of Formula (I) is of Formula (III)
HS-L-O-Q-O-L-SH   (III).

6. The compound of claim 5 , wherein the compound of Formula (III) is
HS—CH 2 CH 2 CH 2 —O-Q-O—CH 2 CH 2 CH 2 —SH.

7. A curable composition comprising:
a) an epoxy resin; and
b) a first curing agent of Formula (I)
HS-L-Y—O-Q-O—Y-L-SH   (I)

wherein
each Y is independently a single bond or a carbonyl group;
each L is independently an alkylene or heteroalkylene; and
Q is a divalent group selected from Formula (I-1), Formula (I-2), or Formula (I-3)

8. The curable composition of claim 7 , further comprising a second curing agent comprising (a) an amine compound having at least one primary amino group or at least one secondary amino group, (b) an imidazole, imidazoline, or salt thereof, (c) a phenol substituted with at least one group selected from a tertiary amino, secondary or tertiary alkyl, nitro, halo, hydroxyl, or combination thereof, (d) a bisphenol, (e) an anhydride, (f) a carboxylic acid, (g) a mercaptan, or (h) a mixture thereof.

9. The curable composition of claim 7 , wherein the first curing agent of Formula (I) is of Formula (II)
HS-L-(CO)—O-Q-O—(CO)-L-SH   (II).

10. The curable composition of claim 7 , wherein the first curing agent of Formula (I) is of Formula (III)
HS-L-O-Q-O-L-SH   (III).

11. The curable composition of claim 7 , wherein the curable composition has a first part comprising the epoxy resin and a second part comprising the compound of Formula (I).

12. An article comprising a first substrate and a cured composition positioned adjacent to the first substrate, the cured composition comprising a reaction product of a curable composition comprising:
a) an epoxy resin; and
b) a first curing agent of Formula (I)
HS-L-Y—O-Q-O—Y-L-SH   (I)

wherein
each Y is independently a single bond or a carbonyl group;
each L is independently an alkylene or heteroalkylene; and
Q is a divalent group of Formula (I-1), Formula (I-2), or Formula (I-3)

13. The article of claim 12 , wherein the first curing agent of Formula (I) is of Formula (II)
HS-L-(CO)—O-Q-O—(CO)-L-SH   (II).

14. The article of claim 12 , wherein the first curing agent of Formula (I) is of Formula (III)
HS-L-O-Q-O-L-SH   (III).

15. The article of claim 12 , wherein the curable composition further comprises a second curing agent comprising (a) an amine compound having at least one primary amino group or at least one secondary amino group, (b) an imidazole, imidazoline, or salt thereof, (c) a phenol substituted with at least one group selected from a tertiary amino, secondary or tertiary alkyl, nitro, halo, hydroxyl, or combination thereof, (d) a bisphenol, (e) an anhydride, (f) a carboxylic acid, (g) a mercaptan, or (h) a mixture thereof.

Assignees

• 3M Innovative Properties Co

Inventors

• Owusu-Adom Kwame
• Lewandowski Kevin M
• Janoski Jonathan E

Classifications

• C07D493/04

  Ortho-condensed systems · CPC title

• C08G59/66 Primary

  Mercaptans · CPC title