IP Library Granted Patent US 11,248,095
Granted Patent B2
US 11,248,095 · App. 16/969,913 · Granted Feb 15, 2022

Photoinitiators for polyolefins

Inventors: Oleg Berezin (Maale Adumim, IL); Dan Rizkov (Beitar-Alite, IL); Boris Gorelik (Zur-Hadassa, IL)
C08J3/28C07C49/84C07C59/13C08J3/24C08K5/06C08J2323/06
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Quick Facts
Patent No.
US 11,248,095
App. No.
16/969,913
Granted
Feb 15, 2022
Kind
B2
Abstract

The technology disclosed herein concerns a family of alkoxybenzophenones for use as photoinitiators for crosslinking polyolefins.

Claims (54)

1. A photoinitiator for use in a method of crosslinking at least one polyolefin, wherein the photoinitiator is an alkoxybenzophenone of the general Formula (I):

wherein

(i) R 1 is —O—(CH 2 ) n —(C═O)—O—(CH 2 ) m —CH 3 , wherein for each variant, independently, each of n and m, independently of the other, is between 0 and 3;

R 2 is H, —(CH 2 ) n —CH 3 or —O—(CH 2 ) n —CH 3 , wherein for each variant, independently, each n is an integer between 4 and 15; and

R 3 is H, —(CH 2 ) n —CH 3 , —O—(CH 2 ) n —CH 3 or —O—(C═O)—(CH 2 ) m —CH 3 , wherein for each variant, independently, each of n and m, independently of the other, is an integer between 4 and 15; or

(ii) R 1 is —O—(CH 2 ) n —CH 3 wherein n is between 1 and 3, or —O—(CH 2 ) n (C═O)—O—(CH 2 ) m —CH 3 , wherein of n and m, independently of the other, is between 0 and 3;

R 2 is —H, —(CH 2 ) n —CH 3 or —O—(CH 2 ) n —CH 3 , wherein for each variant, independently, each n is an integer between 4 and 15; and

R 3 is —H, —(CH 2 ) n —CH 3 , —O—(CH 2 ) n —CH 3 or —O—(C═O)—(CH 2 ) m —CH 3 , wherein for each variant, independently, each of n and m, independently of the other, is an integer between 4 and 15; or

(iii) R 1 is —O—(CH 2 ) n CH 3 or —O—(CH 2 ) n —(C═O)—O—(CH 2 ) m —CH 3 , wherein for each variant, independently, each of n and m, independently of the other, is between 0 and 3;

R 2 is —H, —(CH 2 ) n —CH 3 or —O—(CH 2 ) n —CH 3 , wherein for each variant, independently, each n is an integer between 4 and 15; and

R 3 is —H, —(CH 2 ) n —CH 3 , —O—(CH 2 ) n —CH 3 or —O—(C═O)—(CH 2 ) m —CH 3 , wherein for each variant, independently, each of n and m, independently of the other, is an integer between 4 and 15;

provided that when R 1 is —O—CH 3 , at least one of R 2 and R 3 is different from H.

2. The photoinitiator according to claim 1 , wherein R 1 is —O—CH 2 —CH 3 .

3. The photoinitiator according to claim 1 , wherein R 1 is —O—CH 2 —(C═O)—O—CH 2 —CH 3 .

4. The photoinitiator according to claim 1 , wherein R 1 is —O—CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H; or wherein R 1 is —O—CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H; or wherein R 1 is —O—CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H; or wherein R 1 is —O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H; or wherein R 1 is —O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H; or wherein R 1 is —O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H; or wherein R 1 is —O—CH 2 —(C═O)—O—CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H; wherein R 1 is —O—CH 2 —(C═O)—O—CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H; or wherein R 1 is —O—CH 2 —(C═O)—O—CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H; or wherein R 1 is —O—CH 2 —(C═O)—O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H; or wherein R 1 is —O—CH 2 —(C═O)—O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H; or wherein R 1 is —O—CH 2 —(C═O)—O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H.

5. A compound of Formula (I):

the compound being selected from:

a compound wherein R 1 is —O—CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H;

a compound wherein R 1 is —O—CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H;

a compound wherein R 1 is —O—CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H;

a compound wherein R 1 is —O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H;

a compound wherein R 1 is —O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H;

a compound wherein R 1 is —O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H;

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H;

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H;

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H;

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H;

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H; and

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H.

6. The compound according to claim 5 , being:

a compound wherein R 1 is —O—CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 7 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 9 —CH 3 and R 3 is H; or

a compound wherein R 1 is —O—CH 2 —(C═O)—O—CH 2 —CH 3 , R 2 is —O—(CH 2 ) 11 —CH 3 and R 3 is H.

7. The compound according to claim 5 , wherein the compound is for use as a photoinitiator.

8. A photoinitiator being a compound according to claim 5 .

9. A composition comprising at least one compound according claim 5 , and optionally at least one polyolefin.

10. The composition according to claim 9 , further comprising at least one promoter.

11. The composition according to claim 9 , comprising at least one olefin and at least one promoter.

12. The composition according to claim 10 , wherein the at least one promoter is selected from trimethylol propane tri-methacrylate (TMPTMA) and triallylisocyanurate (TAIC).

13. The composition according to claim 10 , comprising between 0.5 and 5 wt % promoter.

14. The composition according to claim 9 , comprising at least one photoinitiator at a concentration of between 0.01 and 10 wt %.

15. The composition according to claim 14 , wherein the at least one photoinitiator is at a concentration of between 0.05 and 5 wt %.

16. A master batch comprising at least one photoinitiator according to claim 5 , and optionally at least one promoter.

17. A method of crosslinking at least one polyolefin, the method comprising treating, under irradiation, said at least one polyolefin with an amount of a photoinitiator according to claim 5 .

18. The method according to claim 17 , wherein the polyolefin is selected from polyethylene and ethylene copolymers, polyethylene (PE), polypropylene, low density polyethylene (LDPE), linear low-density polyethylene (LLDPE), very low-density polyethylene (VLDPE), ultra-low-density polyethylene (ULDPE), medium-density polyethylene (MDPE), high-density polyethylene (HDPE), ultra-high-density polyethylene (UHDPE), ethylene/propylene copolymers, polypropylene (PP), propylene/ethylene copolymer, ethylene and ethylene, alcohol copolymer (EVOH), ethylene and propylene copolymer, polyisoprene, polybutylene, polybutene, poly-3-methylbutene-1, poly-4-methylpentene-1, or copolymers of ethylene with one or more alpha-olefins.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 20, 2023
From: MOBICHEM SCIENTIFIC ENGINEERING LTD.; N3 COAT LTD.
To: N3CURE LTD.
Reel/Frame 064041/0887 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2021
From: BEREZIN, OLEG; RIZKOV, DAN; GORELIK, BORIS
To: N3 COAT LTD.; MOBICHEM SCIENTIFIC ENGINEERING LTD.
Reel/Frame 057798/0389 →
Priority Claims (1)
IL 257535 · Feb 14, 2018 · national
Continuity (1)
Related Publication 20210115201A1 · Apr 22, 2021