Process for reducing the molecular weight of polypropylene
AssigneeCiba Specialty Chemicals Corporation
InventorsMichael Roth, Rudolf Pfaendner, Peter Nesvadba, Marie-Odile Zink
Life of this patent
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Abstract
The invention relates to the use of known hydroxylamine esters selected from the group consisting of HALS (sterically hindered amine) compounds and novel hydroxylamine esters for the controlled degradation of polypropylene.
Claims15
A process for reducing the molecular weight of polypropylene, propylene copolymers or polypropylene blends, said process comprising heating the polypropylene, propylene copolymers or polypropylene blends at a temperature between 160° C. and 280° C. in the presence of at least one hydroxylamine ester or a polymer of a hydroxylamine ester containing the group of the formula:
- where
- Ra′ is a monoacyl or diacyl radical;
- R1–R4 are each C1–C6alkyl;
- and
- R5 and R6 are each, independently of one another, hydrogen, C1–C6alkyl or C6–C10aryl;
- or
- R5 and R6 are double bonded oxygen.
A process for reducing the molecular weight of polypropylene, propylene copolymers or polypropylene blends, said process comprising heating the polypropylene, propylene copolymers or polypropylene blends at a temperature between 160° C. and 280° C. in the presence of at least one hydroxylamine ester of the formula:
- Ra is an acyl radical selected from the group consisting of —C(═O)—H, —C(═O)—C1–C19alkyl, —C(═O)—C2–C19alkenyl, —C(═O)—C2–C4alkenyl-C6–C10aryl, —C(═O)—C6–C10aryl, —C(═O)—O—C1–C6alkyl, —C(═O)—O—C6–C10aryl, —C(═O)—NH—C1–C6alkyl, —C(═O)—NH—C6–C10aryl, —C(═O)—N(C1–C6alkyl)2, —P(═O)—C1–C19alkyl, —P(═O)2—C1–C19alkyl, —P(═O)—C6–C10aryl, —P═O(—C1–C19alkyl)2, —P═O(—C6–C10aryl)2, —P(═O)—O—C1–C6alkyl, —P(═O)—O—C6–C10aryl, —P═O(—O—C1–C6alkyl)2, —P═O(—O—C6–C10aryl)2, —P(—O—C1–C6alkyl)2 and —P(—O—C6–C10aryl)2;
- R1–R4 are each C1–C6alkyl;
- R5 and R6 are each, independently of one another, hydrogen, C1–C6alkyl or C6–C10aryl;
- or
- R5 and R6 are together oxygen;
- Q is a direct bond or a bivalent radical —(CR7R8)— or —(CR7R8—CR9R10)—, where
- R7, R8, R9 and R10 are each, independently of one another, hydrogen or C1–C6alkyl;
- and
- Z1 is oxygen or a bivalent radical —NR11— or —(CR12R13)—, where
- R11 is hydrogen, C1–C6alkyl, C6–C10aryl or the acyl radical Ra as defined above;
- or, independently of one another,
- R12 and R13 are each hydrogen or C1–C6alkyl, or
- one of the radicals R12 and R13 is hydrogen or C1–C6alkyl and the other is C1–C6alkyl, C1–C6alkoxy, C6–C10aryloxy, acyloxy selected from the group consisting of —O—C(═O)—H, —O—C(═O)—C1–C19alkyl, —O—C(═O)—C1–C54alkenyl, —O—C(═O)—C6–C10aryl, —O—C(═O)—C1–C36alkenyl-C6–C10aryl, —O—C(═O)—O—C1–C6alkyl, —O—C(═O)—O—C6–C10aryl, —O—C(═O)—NH—C1–C6alkyl, —O—C(═O)—NH—C6–C10aryl and —O—C(═O)—N(C1–C6alkyl)2, C1–C6alkylamino, di-C1–C6alkylamino, C6–C10arylamino, acylamino selected from the group consisting of —NH—C(═O)—H, —NH—C(═O)—C1–C19alkyl, —NH—C(═O)—C1–C54alkenyl, —NH—C(═O)—C6–C10aryl, —NH—C(═O)—C1–C36alkenyl-C6–C10aryl, —NH—C(═O)—O—C1–C19alkyl, —NH—C(═O)—O—C6–C10aryl, —NH—C(═O)—NH—C1–C6alkyl, —NH—C(═O)—NH—C6–C10aryl and —NH—C(═O)—N(C1–C6alkyl)2, diacylamino selected from the group consisting of —N[—C(═O)—C1–C19alkyl]2, —N[—C(═O)—C6–C10aryl]2, —N[—C(═O)—C1–C6alkylene-C(═O)—], —N[—C(═O)—C2–C6alkenylene-C(═O)—] and phthalimido or N-acyl-N—C1–C6alkylamino;
- or the two radicals R12 and R13 are together oxo;
- or
- a compound of the formula Ib, where
- Ra is an acyl radical selected from the group consisting of —C(═O)—H, —C(═O)—C1–C19alkyl, —C(═O)—C2–C19alkenyl, —C(═O)—C2–C4alkenyl-C6–C10aryl, —C(═O)—C6–C10aryl, —C(═O)—O—C1–C6alkyl, —C(═O)—O—C6–C10aryl, —C(═O)—NH—C1–C6alkyl, —C(═O)—NH—C6–C10aryl and —C(═O)—N(C1–C6alkyl)2;
- R1–R4 are each C1–C6alkyl;
- A are substituents on the phenyl rings;
- and
- m is an integer from one to four;
- or
- a compound of the formula Ic, where
- Ra is an acyl radical selected from the group consisting of —C(═O)—H, —C(═O)—C1–C19alkyl, —C(═O)—C2–C19alkenyl, —C(═O)—C2–C4alkenyl-C6–C10aryl, —C(═O)—C6–C10aryl, —C(═O)—O—C1–C6alkyl, —C(═O)—O—C6–C10aryl, —C(═O)—NH—C1–C6alkyl, —C(═O)—NH—C6–C10aryl, —C(═O)—N(C1–C6alkyl)2, —P(═O)—C1–C19alkyl, —P(═O)2—C1–C19alkyl, —P(═O)—C6–C10aryl, —P═O(—C1–C19alkyl)2, —P═O(—C6–C10aryl)2, —P(═O)—O—C1–C6alkyl, —P(═O)—O—C6–C10aryl, —P═O(—O—C1–C6alkyl)2, —P═O(—O—C6–C10aryl)2, —P(—O—C1–C6alkyl)2 and —P(—O—C6–C10aryl)2;
- Rb is hydrogen, carbamoyl, C1–C6alkylcarbamoyl, di-C1–C6alkylcarbamoyl or is as defined for Ra;
- Rc and Rd are each, independently of one another, hydrogen, C1–C20alkyl or C6–C10aryl;
- and
- R1–R3 are each C1–C6alkyl or C6–C10aryl;
- or
- a compound of the formula:
- where
- n is two;
- X is a direct bond or the monovalent radical of a C1–C18alkylene bridge;
- R1–R4 are each C1–C6alkyl;
- R5 and R6 are each, independently of one another, hydrogen, C1–C6alkyl or C6–C10aryl;
- or
- R5 and R6 are together oxygen;
- Q is a direct bond or a bivalent radical —(CR7R8)— or —(CR7R8—CR9R10)—, where
- R7, R8, R9 and R10 are each, independently of one another, hydrogen or C1–C6alkyl;
- and
- Z1 is oxygen or a bivalent radical —NR11— or —(CR12R13)—, where
- R11 is hydrogen, C6–C10aryl or C1–C6alkyl or, independently of one another,
- one of the radicals R12 and R13 is hydrogen or C1–C6alkyl and the other is C1–C6alkyl, C1–C6alkoxy, C6–C10aryloxy, acyloxy selected from the group consisting of —O—C(═O)—H, —O—C(═O)—C1–C19alkyl, —O—C(═O)—C1–C54alkenyl, —O—C(═O)—C6–C10aryl, —O—C(═O)—C1–C36alkenyl-C6–C10aryl, —O—C(═O)—O—C1–C6alkyl, —O—C(═O)—O—C6–C10aryl, —O—C(═O)—NH—C1–C6alkyl, —O—C(═O)—NH—C6–C10aryl and —O—C(═O)—N(C1–C6alkyl)2, C1–C6alkylamino, di-C1–C6alkylamino, C6–C10arylamino, acylamino selected from the group consisting of —NH—C(═O)—H, —NH—C(═O)—C1–C19alkyl, —NH—C(═O)—C1–C54alkenyl, —NH—C(═O)—C6–C10aryl, —NH—C(═O)—C1–C36alkenyl-C6–C10aryl, —NH—C(═O)—O—C1–C19alkyl, —NH—C(═O)—O—C6–C10aryl, —NH—C(═O)—NH—C1–C6alkyl, —NH—C(═O)—NH—C6–C10aryl and —NH—C(═O)—N(C1–C6alkyl)2, diacylamino selected from the group consisting of —N[—C(═O)—C1–C19alkyl]2, —N[—C(═O)—C6–C10aryl]2, —N[—C(═O)—C1–C6alkylene-C(═O)—], —N[—C(═O)—C2–C6alkenylene-C(═O)—] and phthalimido or N-acyl-N—C1–C6alkylamino;
- or the two radicals R12 and R13 are together oxo;
- or
- a compound of the formula:
- where
- n is two
- Ra is an acyl radical selected from the group consisting of —C(═O)—H, —C(═O)—C1–C19alkyl, —C(═O)—C2–C19alkenyl, —C(═O)—C2–C4alkenyl-C6–C10aryl, —C(═O)—C6–C10aryl, —C(═O)—O—C1–C6alkyl, —C(═O)—O—C6–C10aryl, —C(═O)—NH—C1–C6alkyl, —C(═O)—NH—C6–C10aryl and —C(═O)—N(C1–C6alkyl)2;
- X is a direct bond or the monovalent radical of a C1–C18alkylene bridge;
- R1–R4 are each C1–C6alkyl;
- R5 and R6 are each, independently of one another, hydrogen C1–C6alkyl or C6–C10aryl;
- or
- R5 and R6 are together oxygen;
- and
- Q is a direct bond or a bivalent radical —(CR7R8)— or —(CR7R8—CR9R10)—, where
- R7, R8, R9 and R10 are each, independently of one another, hydrogen or C1–C6alkyl.
Dependencies are inferred from the claim text.