Sulfur-based functional prepolymers for polyurethanes and polymeric materials

Patent metadata

Field	Value
Publication number	US-12534565-B2
Application number	US-202117797531-A
Country	US
Kind code	B2
Filing date	Feb 4, 2021
Priority date	Feb 5, 2020
Publication date	Jan 27, 2026
Grant date	Jan 27, 2026

Abstract

A composition includes a reaction product of a mixture of elemental sulfur and at least a first ethylenically unsaturated compound comprising a hydroxyl or carboxyl group.

First claim

What is claimed is:

1 . A composition comprising:
a reaction product of a mixture comprising:
elemental sulfur wherein the elemental sulfur is S 8 ;
a first ethylenically unsaturated compound comprising a hydroxyl or carboxyl group and is a compound of formula:

wherein:
E is —OH or —C(O)OH,
R 1 and R 2 are each individually, H, alkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, heterocyclylalkyl, cycloalkylalkyl, or heteroarylalkyl, and
R 3 is a linear or branched C 1 -C 50 alkylenyl group; and

a second, or more, ethylenically unsaturated compound(s), and the second, or more, ethylenically unsaturated compound(s) comprises:
a (meth)acrylate or is represented by one or more of the following formulas:

wherein:
R 4 and R 5 are each individually H, alkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, heterocyclylalkyl, cycloalkylalkyl, or heteroarylalkyl;
R 6 is alkylenyl, cycloalkylenyl, heterocyclylene, arylene, or heteroarylene;
each R 7 is individually NO 2 , NH 2 , F, Cl, Br, I, CN, alkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, heterocyclylalkyl, cycloalkylalkyl, or heteroarylalkyl;
R 8 , R 9 , and R 10 are each individually H, alkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, aralkyl, heterocyclylalkyl, cycloalkylalkyl, or heteroarylalkyl;
R 11 , R 12 , R 13 , and R 14 are each individually alkyl or aryl;
m is 0, 1, 2, 3, 4, or 5; and
n is 1 to 1000; or

one or more cyclic olefins selected from a monocyclic olefin, a monocyclic bicyclic diene, a bicyclic olefin, and a bicyclic diene.

2 . The composition of claim 1 , wherein the first ethylenically unsaturated compound comprising a hydroxyl or carboxyl group is 10-undecene-1-ol, cinnamyl alcohol, 9-decen-1-ol, 5-hexen-1-ol, 7-octen-1-ol, 10-undecenoic acid, or 3-hydroxy-4-methoxycinnamic acid.

3 . The composition of claim 1 , wherein the first ethylenically unsaturated compound comprises 10-undecene-1-ol.

4 . The composition of claim 1 , wherein the first ethylenically unsaturated compound comprises 10-undecenoic acid.

5 . The composition of claim 1 , wherein the second ethylenically unsaturated compound comprises 1,3-diisopropenylbenzene.

6 . The composition of claim 1 , wherein the second, or more, ethylenically unsaturated compound(s) is the cyclic olefin, and the cyclic olefin is norbornene, norbornadiene, or a compound comprising at least one of the following:

wherein n is 1 or 2.

7 . A polymeric composition comprising a reaction product of an isocyanate and the composition of claim 1 .

8 . The polymeric composition of claim 7 , wherein the isocyanate comprises at least one terminal —NCO functional group or the isocyanate comprises two terminal —NCO functional groups.

9 . A polymeric composition comprising the reaction product of the polymeric composition of claim 7 ; an isocyanate; and a diol, wherein the reaction product is a block polyurethane copolymer.

10 . The polymeric composition of claim 9 , wherein:
(i) the diol is represented as HOROH, wherein R is a C 1 -C 20 alkylenyl group; (ii) the diol is represented as HO((CH 2 ) n O) m H, wherein n is 1-20 and m is 50 to 3000; or (iii) the diol is poly(tetramethylene ether)glycol, polyethylene glycol, polypropylene glycol, polycaprolactone diol, or polycarbonate diol.

11 . The polymeric composition of claim 9 , wherein the isocyanate comprises 4,4′-methylene diphenyl diisocyanate, 2,4-diisocyanato-1-methylbenzene, tolylene 2,6-diisocyanate, 1,6-diisocyanatohexane, isophorone diisocyanate, or 4,4′-diisocyanatodicyclohexylmethane.

12 . An article of manufacture comprising the polymeric composition of claim 7 , wherein the article of manufacture comprises a fire retardant composition, coating article, film article, packaging article, foam article, insulation article, injection molded article, strapping article, banding article, seal, gasket, wheel, tire, electronic article, fiber, textile, or adhesive.

13 . A fire retardant composition comprising the composition of claim 1 .

14 . The fire retardant composition of claim 13 , wherein when a substrate combined with the fire retardant composition is ignited to be on fire, the fire retardant composition forms a charring layer on a surface of the substrate that is effective for extinguishing the fire.

15 . The fire retardant composition or polymeric composition of claim 14 , wherein the charring layer comprises at least about 10 wt % char, and wherein the fire retardant composition provides for test specimens that are combined with the fire retardant composition to exhibit a limiting oxygen index (LOI) of at least 25 and a UL94-V rating of V-1 or V-0.

16 . A flame resistant substrate comprising a base material combined with the fire retardant composition of claim 13 .

Assignees

• Univ Arizona

Inventors

• Kang Kyungseok
• Pyun Jeffrey
• Lee Taeheon

Classifications

• C09K2003/1078

  Fire-resistant, heat-resistant materials · CPC title

• C09D5/18

  Fireproof paints {including high temperature resistant paints} · CPC title

• C08G2390/00

  Containers · CPC title

• C08G2380/00

  Tyres · CPC title

• C08G2190/00

  Compositions for sealing or packing joints · CPC title