IP Library Granted Patent US 12,460,041
Granted Patent B2
US 12,460,041 · App. 17/785,548 · Granted Nov 4, 2025

Method for improving the flame, smoke and/or toxicity retardancy in polyisocyanurate / polyurethane (PIR/PUR) comprising materials

Inventors: Rene Alexander Klein (Hoegaarden, BE); Nima Esmaeili (Etterbeek, BE); Nadja Kathrin Richter (Brussels, BE); Rajesh Kumar Gajendran (Brussels, BE); Xiaodong Guo (Mechelen, BE); Thomas Julien Joncheray (Woluwe Saint Pierre, BE); Jan Vandenbroeck (Scherpenheuvel-Zichem, BE)
C08G18/12C08F4/34C08F220/20C08F222/104C08F290/067C08G18/092C08G18/14C08G18/18C08G18/1833C08G18/1866C08G18/2036C08G18/48C08G18/4804C08G18/672C08G18/673C08G18/7664C08G18/794C08G18/8175C08J9/141C08K5/14C08G2101/00C08G2110/0025C08G2115/02C08G2350/00
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Quick Facts
Patent No.
US 12,460,041
App. No.
17/785,548
Granted
Nov 4, 2025
Kind
B2
Abstract

A polyisocyanurate and/or polyurethane (PIR/PUR) comprising material having improved Flame. Smoke and/or Toxicity (FST) retardancy is disclosed and a method for forming said PIR/PUR comprising material. The PIR/PUR material is comprising at least 0.2 wt % of compounds having a number average equivalent weight<160 g/mol and at least one non-polymerized ethylenically unsaturated moiety based on the total weight of the PIR/PUR comprising material, and optionally 0.01 wt % up to 1 wt % of one or more radical initiator compounds based on the total weight of the PIR/PUR comprising material.

Claims (30)

1 . A polyisocyanurate and/or polyurethane (PIR/PUR) comprising material that comprises:

at least 0.2 wt % of ethylenically unsaturated compounds based on the total weight of the PIR/PUR comprising material, said compounds having a number average equivalent weight<160 g/mol and having at least one non-polymerized ethylenically unsaturated moiety, and

optionally 0.01 wt % up to 1 wt % of one or more radical initiator compounds based on the total weight of the PIR/PUR comprising material and

wherein the compounds having at least one non-polymerized ethylenically unsaturated moiety are selected or originating from compounds having at least one ethylenically unsaturated moiety and having an onset temperature for radical polymerization (T onset ) with or without the radical initiator which is 2° C. up to 40° C., lower than the maximum reaction temperature achieved during the process for making the PIR/PUR comprising material (T reaction ).

2 . The PIR/PUR comprising material according to claim 1 , wherein the compounds having at least one non-polymerized ethylenically unsaturated moiety are selected or originating from compounds having at least one ethylenically unsaturated moiety and having an onset temperature for radical polymerization (T onset ) with or without the radical initiator which is 5° C. up to 30° C. lower than the maximum reaction temperature achieved during the process for making the PIR/PUR comprising material (T reaction ).

3 . The PIR/PUR comprising material according to claim 1 , wherein the total amount of compounds having at least one non-polymerized ethylenically unsaturated moiety and compounds originating from compounds having at least one ethylenically unsaturated moiety in the PIR/PUR comprising material is in the range 2 wt % up to 30 wt %, based on the total weight of the PIR/PUR comprising material.

4 . The PIR/PUR comprising material according to claim 1 , wherein the amount of compounds having at least one non-polymerized ethylenically unsaturated moiety is in the range 0.2 wt % up to 27 wt % based on the total weight of the PIR/PUR comprising material.

5 . The PIR/PUR comprising material according to claim 1 , wherein the compound having at least one non-polymerized ethylenically unsaturated moiety is selected from an acrylate, methacrylate, acrylic acid, methacrylic acid, allyl alcohol, maleic acid, or mixtures thereof.

6 . The PIR/PUR comprising material according to claim 1 , wherein the compound having at least one non-polymerized ethylenically unsaturated moiety comprises 2 to 8 non-polymerized ethylenically unsaturated moieties.

7 . The PIR/PUR comprising material according to claim 1 , wherein the compound having at least one non-polymerized ethylenically unsaturated moiety is selected or originating from pentaerythritol tri-acrylate (PETA), pentaerythritol tetra-acrylate (PETRA), ethylene glycol diacrylate (EGDA), hydroxyethyl acrylate (HEA), diethylene glycol diacrylate (DEGDA), hydroxyethyl methacrylate (HEMA), ethylene glycol dimethacrylate (EGDMA) and diethylene glycol dimethacrylate (DEGDMA).

8 . The PIR/PUR comprising material according to claim 1 , wherein the compounds having at least one non-polymerized ethylenically unsaturated moiety and/or the compounds originating from compounds having at least one ethylenically unsaturated moiety are originating from compounds comprising at least one isocyanate reactive moiety.

9 . The PIR/PUR comprising material according to claim 1 , wherein the compound having at least one non-polymerized ethylenically unsaturated moiety has a boiling point under atmospheric pressure higher than 150° C.

10 . The PIR/PUR comprising material according to claim 1 , wherein the radical initiator is selected from peroxide compounds.

11 . A method comprising at least combining and mixing following ingredients to form a polyisocyanurate and/or polyurethane (PIR/PUR) comprising material comprising:

a polyisocyanate composition comprising one or more polyisocyanate compounds; and

an isocyanate-reactive composition comprising one or more isocyanate-reactive compounds; and

at least one catalyst compound selected from a trimerization (PIR) catalyst and/or polyurethane (PUR) forming catalyst, and

at least one compound having at least one ethylenically unsaturated moiety and having a number average equivalent weight<160 g/mol, and

optionally one or more radical initiator compound, and

optionally a blowing agent; and

optionally one or more surfactants, one or more flame retardants, one or more antioxidants, or combinations thereof; and

characterized in that the amount of compounds having at least one ethylenically unsaturated moiety is at least 2 wt % based on the total weight of all ingredients used to make the PIR/PUR comprising material and the onset temperature for radical polymerization (T onset ) of the combination of the ethylenically unsaturated compound and the radical initiator (if present) is 2° C. up to 40° C. lower than the maximum reaction temperature achieved during the process for making the PIR/PUR comprising material (reaction exotherm (T reaction )), and

wherein, after forming the PIR/PUR comprising material, the PIR/PUR comprising material comprises 0.2 wt % up to 27 wt % of un-reacted compounds of the at least one compound having at least one ethylenically unsaturated moiety based on the total weight of the PIR/PUR comprising material.

12 . The method according to claim 11 , wherein the onset temperature for radical polymerization (T onset ) of the combination of the ethylenically unsaturated compound and the radical initiator (if present) is 5° C. up to 30° C. lower than the maximum reaction temperature achieved during the process for making the PIR/PUR material (reaction exotherm (T reaction )).

13 . The method according to claim 11 , wherein the amount of compounds having at least one ethylenically unsaturated moiety is in the range 2 wt % up to 30 wt % based on the total weight of all ingredients used to make the PIR/PUR comprising material.

14 . The method according to claim 11 , wherein the PIR/PUR comprising material is a polyisocyanurate (PIR) comprising material and the method for forming the PIR comprising material is performed at an isocyanate index of 180 or higher and the catalyst compound is selected from at least one trimerisation catalyst.

15 . The method according to claim 11 , wherein the PIR/PUR comprising material is a polyurethane (PUR) comprising material and the method for forming the PUR comprising material is performed at an isocyanate index in the range 80-180 and the catalyst compound is selected from at least one polyurethane catalyst.

16 . The method according to claim 11 , wherein the at least one compound having at least one ethylenically unsaturated moiety comprises acrylic acid, methacrylic acid, allyl alcohol, maleic anhydride, or mixtures thereof.

17 . The method according to claim 11 , wherein the at least one compound having at least one ethylenically unsaturated moiety comprises at least one isocyanate reactive moiety.

18 . The method according to claim 11 , wherein 20 wt % up to 80 wt % of the total amount of the at least one compound having at least one ethylenically unsaturated moiety still have a non-polymerized ethylenically unsaturated moiety after forming the PIR/PUR comprising material.

Assignments (3)
SECURITY INTEREST Recorded May 4, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCOMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK N.A.
Reel/Frame 075498/0663 →
PATENT SECURITY AGREEMENT Recorded Mar 10, 2026
From: HUNTSMAN INTERNATIONAL LLC; HUNTSMAN ADVANCED MATERIALS AMERICAS LLC; HUNTSMAN NANOCAMP LLC; HUNTSMAN PETROCHEMICAL LLC
To: CITIBANK, N.A.
Reel/Frame 075106/0238 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 23, 2022
From: KLEIN, RENE ALEXANDER; ESMAEILI, NIMA; RICHTER, NADJA KATHRIN; GAJENDRAN, RAJESH KUMAR; GUO, XIAODONG; JONCHERAY, THOMAS JULIEN; VANDENBROECK, JAN
To: HUNTSMAN INTERNATIONAL LLC
Reel/Frame 062198/0507 →
Priority Claims (1)
EP 19219222 · Dec 23, 2019 · regional
Continuity (1)
Related Publication 20230021509A1 · Jan 26, 2023
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