IP Library Granted Patent US 12674027
Granted Patent B2
US 12674027 · App. 17/621,515 · Granted Jul 7, 2026

Polymerized high-molecular-weight sterically hindered amine and preparation method thereof

Inventors: Jingjing An (Beijing, CN); Wei Chen (Beijing, CN); Yongnian Gao (Beijing, CN); Jing Li (Beijing, CN); Gang Liu (Beijing, CN)
Assignee: BEIJING TIANGANG AUXILIARY CO., LTD.
C08G73/0627C08G73/0633C08G73/0644
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Quick Facts
Patent No.
US 12674027
App. No.
17/621,515
Granted
Jul 7, 2026
Kind
B2
Abstract

The present invention discloses a polymerized high-molecular-weight sterically hindered amine having a general formula I, the sterically hindered amine has the advantages of high molecular weight, difficult migration in polymer products, good thermal stability, etc., and can stabilize and/or be flame retardant to organic substances sensitive to light, heat or oxidation, and furthermore, can be made to have better compatibility with different types of polymer materials by changing substituents.

Claims (26)

1 . A polymerized high-molecular-weight sterically hindered amine, wherein the polymerized high-molecular-weight sterically hindered amine is selected from the following structures:

m n is an integer between 2-20;

Q 1 , Q 2 and Q 3 are independently selected from —O—, —CO—O—, —CO—NR 22 — or —NR 22 —; R 22 is independently selected from hydrogen and C 1 -C 20 alkyl;

R 1 and R 2 are independently selected from hydrogen, and C 1 -C 40 alkyl, wherein any one or more of the H atoms in the alkyl can be substituted with —R 21 , —OR 21 , —COOR 21 or —COR 21 ; R 3 is selected from C 1 -C 40 alkylene, wherein any one or more of the H atoms in the alkylene can be substituted with —R 21 , —OR 21 , —COOR 21 or —COR 21 ; the total number of carbon atoms in —R 1 , R 2 and R 3 is 40 or less;

R 7 and R 8 are independently selected from hydrogen, unsubstituted C 1 -C 20 alkyl or C 1 -C 20 alkyl substituted with —R 21 ; or, R 7 , R 8 and the N atom between R 7 and R 8 form unsubstituted C 3 -C 12 cycloalkylene or C 2 -C 12 heterocycloalkylene;

R 4 and R 5 are independently selected from hydrogen, and C 1 -C 40 alkyl, wherein any one or more of the H atoms in the alkyl can be substituted with —R 21 , —OR 21 , —COOR 21 or —COR 21 ; R 6 is selected from C 1 -C 40 alkylene, wherein any one or more of the H atoms in the alkylene can be substituted with —R 21 , —OR 21 , —COOR 21 or —COR 21 ; and the total number of carbon atoms in —R 4 , R 5 and R 6 is 40 or less; and

R 12 and R 13 are independently selected from hydrogen, unsubstituted C 4 -C 30 alkyl or C 4 -C 30 alkyl wherein any one or more of the H atoms in the alkyl can be subsiitute with hydroxyl, —NO 2 , halogen, amino, cyano, —R 21 , —OR 21 , —COOOR 21 , —COR 21 or C 1 -C 10 alkyl,

R 21 is selected from C 1 -C 20 alkyl.

2 . The polymerized high-molecular-weight sterically hindered amine according to claim 1 , wherein —R 21 is selected from C 1 -C 12 alkyl;

Q 1 and Q 2 are independently selected from —CO—O—, —CO—NR 22 — or —NR 22 —;

—R 22 is selected from hydrogen, and C 1 -C 12 alkyl;

—R 7 and R 8 are independently selected from unsubstituted C 1 -C 20 alkyl; or, R 7 , R 8 and the N atom between R 7 and R 8 form unsubstituted C 3 -C 10 cycloalkylene or C 2 -C 8 oxo-cycloalkylene; and

Q 3 is selected from —NR 22 —.

3 . The polymerized high-molecular-weight sterically hindered amine according to claim 1 , wherein R 1 and R 2 are independently selected from hydrogen or C 1 -C 40 alkyl; R 3 is selected from C 1 -C 40 alkylene; the total number of carbon atoms in R 1 , R 2 and R 3 is 40 or less;

R 22 is selected from C 1 -C 5 alkyl;

R 7 and R 8 are independently selected from C 1 -C 10 alkylene or R 7 , R 8 and the N atom between R 7 and R 8 form C 3 -C 10 cycloalkylene and C 2 -C 8 oxo-cycloalkylene;

R 4 and R 5 are independently selected from hydrogen or C 1 -C 40 alkyl; R 6 is selected from C 1 -C 40 alkylene; the total number of carbon atoms in R 4 , R 5 and R 6 is 40 or less; and

Q 1 , Q 2 and Q 3 are independently selected from —CO—O—, —CO—NR 22 — or —NR 22 —, and R 22 is selected from C 1 -C 5 alkyl.

4 . A method for preparing the polymerized high-molecular-weight sterically hindered amine of claim 1 , including the steps of dissolving a polymerizable monomer in a solvent or heating a polymerizable monomer to a molten state, adding a catalyst and hydroperoxide in sequence, and carrying out a reaction to generate the polymerized high-molecular-weight sterically hindered amine wherein the polymerizable monomer has a general formula as follows:

wherein

R and R′ can be the same or different, and are selected from C 1 -C 50 alkyl, C 3 -C 12 cycloalkyl, and C 2 -C 12 heterocycloalkyl, wherein the any one or more of the H atoms in the alkyl, cycloalkyl, or heterocycloalkyl can be substituted with hydroxyl, NO 2 , halogen, amino, cyano, —R 21 , —OR 21 , —COOR 21 or —COR 21 , and the hetero atom in the heterocyclic ring is selected from oxygen, nitrogen, sulfur, phosphorus or silicon; and the total number of carbon atoms in R and R′ is 50 or less;

the solvent is dichlorobenzene, chlorobenzene, toluene, halogenated hydrocarbons, methanol, ethanol, ethylene glycol, methyl ether or water;

the catalyst is a metal compound, wherein the metal in the metal compound is selected from IVb, B Vb, VIb, VIIb and VIII metal elements in the periodic table; and

the hydroperoxide is an inorganic hydroperoxide or an organic hydroperoxide, the inorganic or an aryl hydroperoxide is H 2 O 2 ; the organic hydroperoxide is an alkyl hydroperoxide or an aryl hydroperoxide.

5 . A composition, comprising one or two or more organic substances sensitive to light, heat or oxidation and at least one polymerized high-molecular-weight sterically hindered amine according to claim 1 .

6 . A method for preparing the polymerized high-molecular-weight sterically hindered amine according to claim 4 , wherein the catalyst is one or more selected from the group consisting of vanadiumoxy acetylacetonate, vanadium (Ill) acetylacetonate, cobalt carbonyl, chromium (VI) oxide, n-butyl titanate, isopropyl titanate, hexacarbonyl molybdenum, molybdenum trioxide, vanadium pentoxide, chromium trioxide and tungsten trioxide.