IP Library Granted Patent US 10,920,052
Granted Patent B2
US 10,920,052 · App. 16/060,080 · Granted Feb 16, 2021

Process for reducing fogging from high melt strength polypropylene

Inventors: Wilhelm Klaas Frijlink (Zwolle, NL); Jan Martijn Van Der Schuur (Hengelo, NL); Auke Gerardus Talma (Bathmen, NL); Michel Van Den Berg (Elst, NL)
Assignee: NOURYON CHEMICALS INTERNATIONAL B.V.
C08L23/12C08F110/06C08J7/065C08K5/09C08K5/092C08K5/14C08K5/1539C08J2323/12
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Quick Facts
Patent No.
US 10,920,052
App. No.
16/060,080
Granted
Feb 16, 2021
Kind
B2
Abstract

Process for reducing fogging from high melt strength polypropylene (HMS-PP) obtained by heat treating polypropylene at a temperature between 150° C. and 300° C. in the presence of a dialkyl peroxydicarbonate, said process involving the introduction of an anhydride to said high melt strength polypropylene.

Claims (22)

1. A process for reducing fogging from high melt strength polypropylene (HMS-PP), the process comprising a step of heat treating polypropylene at a temperature between 150° C. and 300° C. in the presence of a dialkyl peroxydicarbonate to obtain a high melt strength polypropylene, introducing an anhydride into the high melt strength polypropylene, and carrying out a fogging analysis on the high melt strength polypropylene after introduction of the anhydride into the high melt strength polypropylene, wherein the anhydride is selected from the group consisting of bisanhydrides, oligoanhydrides, and mono-anhydrides of formula (I),

wherein R 1 is selected from hydrogen and saturated, unsaturated, linear, branched, or cyclic hydrocarbon chains with 2 to 30 carbon atoms, optionally substituted with oxygen-containing groups, R 2 is selected from hydrogen and saturated, unsaturated, linear, branched, or cyclic hydrocarbon chains with 2 to 30 carbon atoms, optionally substituted with oxygen-containing groups, R 3 is selected from hydrogen, hydroxyl groups, and saturated, linear, branched, and/or cyclic hydrocarbon chains with 2 to 30 carbon atoms, optionally substituted with oxygen-containing groups, R 1 and R 2 or R 1 and R 3 can be connected to form a saturated aliphatic ring or a saturated heterocyclic ring; and n=1.

2. A process for enhancing the melt strength of polypropylene, comprising heat treating the polypropylene at a temperature between 150° C. and 300° C. in the presence of 0.3-3 wt %, based on the weight of the polypropylene, of a dialkyl peroxydicarbonate, and introducing an anhydride into the polypropylene before or during said heat treatment, in a molar ratio anhydride functionalities/dialkyl peroxydicarbonate in the range 0.8-3.6, said anhydride being selected from the group consisting of mono-anhydrides of formula (I), bisanhydrides, and oligo-anhydrides,

wherein R 1 is selected from hydrogen and saturated, linear, branched, or cyclic hydrocarbon chains with 2 to 30 carbon atoms, optionally substituted with oxygen-containing groups, R 2 is selected from hydrogen and saturated, unsaturated, linear, branched, or cyclic hydrocarbon chains with 2 to 30 carbon atoms, optionally substituted with oxygen-containing groups, R 3 is selected from hydrogen, hydroxyl groups, and saturated linear, branched, and/or cyclic hydrocarbon chains with 2 to 30 carbon atoms, optionally substituted with oxygen-containing groups, R 1 and R 2 or R 1 and R 3 can be connected to form a saturated aliphatic ring or a saturated heterocyclic ring; and n=1,

wherein the anhydride is formed in-situ from a corresponding polycarboxylic acid, said process requiring the addition of the polycarboxylic acid to the polypropylene before or during said heat treating, and

wherein the polycarboxylic acid is selected from the group consisting of citric acid;

phthalic acid; succinic acid; and succinic acid-modified polyolefins/oligomers.

3. The process according to claim 1 wherein R 1 and R 3 are hydrogen.

4. The process according to claim 3 wherein R 2 is an unsaturated hydrocarbon chain and the anhydride does not graft into the polypropylene.

5. The process according to claim 4 wherein the anhydride is an alkenyl succinic anhydride (ASA).

6. The process according to claim 5 wherein the ASA has an alkenyl chain with 6 to 24 carbon atoms.

7. The process according to claim 6 wherein the alkenyl chain has 8 to 18 carbon atoms.

8. The process according to claim 1 wherein the anhydride is formed in-situ from the corresponding polycarboxylic acid, said process requiring the addition of said polycarboxylic acid to the high melt strength polypropylene, which is then subjected to a further heat treatment.

9. The process according to claim 2 wherein a molar ratio anhydride functionalities/dialkyl peroxydicarbonate is in the range 1.2-2.5.

10. The process according to claim 1 wherein the dialkyl peroxydicarbonate is dicetyl peroxydicarbonate, dimyristyl peroxydicarbonate, or di(4-tert-butylcyclohexyl) peroxydicarbonate.

11. The process according to claim 1 wherein the anhydride is selected from the group consisting of n-octenyl succinic anhydride; n-dodecenyl succinic anhydride; tetrapropenyl succinic anhydride; n-octadecenyl succinic anhydride; i-octadecenyl succinic; i-hexadecenyl succinic anhydride; octadecenyl succinic anhydride and any mixtures thereof.

12. The process according to claim 1 wherein the step of heat treating is performed at a temperature between 160° C. and 240° C.

13. The process according to claim 2 wherein the step of heat treating is performed at a temperature between 160° C. and 240° C.

14. The process according to claim 8 wherein the polycarboxylic acid is selected from the group consisting of citric acid; phthalic acid; succinic acid; and succinic acid-modified polyolefins/oligomers.

15. The process according to claim 2 wherein the dialkyl peroxydicarbonate is dicetyl peroxydicarbonate, dimyristyl peroxydicarbonate, or di(4-tert-butylcyclohexyl) peroxydicarbonate.

16. A high melt strength polypropylene formed from the process of claim 1 .

17. A polypropylene formed from the process of claim 2 .

Assignments (4)
CHANGE OF NAME Recorded Sep 18, 2019
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 050426/0671 →
SECURITY INTEREST Recorded Oct 1, 2018
From: STARFRUIT US MERGER SUB 1 LLC; STARFRUIT US MERGER SUB 2 LLC; AKZO NOBEL SURFACE CHEMISTRY LLC; AKZO NOBEL CHEMICALS B.V.; AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: WILMINGTON TRUST (LONDON) LIMITED, AS COLLATERAL AGENT
Reel/Frame 047231/0001 →
CORRECTIVE ASSIGNMENT TO CORRECT THE CORRESPONDENCE MIDDLE INITIAL AND SECOND ASSIGNOR NAME PREVIOUSLY RECORDED AT REEL: 046138 FRAME: 0278. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 29, 2018
From: FRIJLINK, WILHELM KLAAS; VAN DER SCHUUR, JAN MARTIJN; TALMA, AUKE GERARDUS; VAN DEN BERG, MICHEL
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 046464/0189 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 20, 2018
From: FRIJLINK, WILHELM KLAAS; VAN DER SHUUR, JAN MARTIJN; TALMA, AUKE GERARDUS; VAN DEN BERG, MICHEL
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 046138/0278 →