US2002123577A1PendingUtilityA1
Functionalised polymers
Priority: Oct 31, 1996Filed: Nov 9, 2001Published: Sep 5, 2002
Est. expiryOct 31, 2016(expired)· nominal 20-yr term from priority
C08K 5/34Y10T428/31913C08F 8/00C08K 5/005Y10T428/31928C08K 5/0008
48
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Claims
Abstract
This invention relates to a process for stabilizing and at the same time phase compatibilising plastics or plastic compositions by incorporating polymeric compounds obtainable by reacting a compound selected from the group consisting of the sterically hindered phenols, sterically hindered amines, lactones, sulfides, phosphites, benzotriazoles, benzophenones and 2-(2-hydroxyphenyl)-1,3,5-triazines, which compounds contain at least one reactive group, with a compatibilisator.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A process for stabilising and at the same time phase compatibilising plastics or plastic compositions by incorporating polymeric compounds obtainable by reacting a compound selected from the group consisting of the sterically hindered phenols, sterically hindered amines, lactones, sulfides, phosphites, benzotriazoles, benzophenones and 2-(2-hydroxyphenyl)-1,3,5-triazines, which compounds contain at least one reactive group, with a compatibilisator.
2 . A process according to claim 1 , wherein the sterically hindered phenols are compounds of formula I
R 1 and R 2 are each independently of the other hydrogen, C 1 -C 25 alkyl, phenyl-C 1 -C 3 alkyl which is unsubstituted or substituted once or several times at the aromatic ring by OH or/and C 1 -C 4 alkyl, unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 12 cycloalkyl, or phenyl;
n is 1, 2 or 3;
E is OH, SH, NHR 3 , SO 3 H, COOH, —CH═CH 2 ,
m is 0 or 1;
R 3 is hydrogen or C 1 -C 9 alkyl;
R 4 is C 1 -C 12 alkyl, or phenyl which is unsubstituted or substituted by one or several C 1 -C 4 -alkyl, halogen or/and C 1 -C 18 alkoxy;
A if E is OH, SH or —CH═CH 2 , is —C x H 2x —, —CH 2 —S—CH 2 CH 2 —, —C q H 2q —(CO)—O—C p H 2p —, —C q H 2q —(CO)—NH—C p H 2p — or —C q H 2q —(CO)—O—C p H 2p —S—C q H 2q —;
x is a number from 0 to 8;
p is a number from 2 to 8;
q is a number from 0 to 3;
R 1 and n are as defined above; or
A if E is —NHR 3 , is —C x H 2x — or —C q H 2q —(CO)—NH—C p H 2p —, wherein x, p and q have the meanings cited above; or
A if E is COOH or SO 3 H, is —C x H 2x —, —CH 2 —S—CH 2 — or —CH 2 —S—CH 2 CH 2 —, wherein x has the meaning cited above; or
A if E is
is a direct bond, —C q H 2q —(CO) m —O—CH 2 — or —C x H 2x —S—CH 2 —, wherein q, m, x, R 1 and R 2 are as defined above;
A if E is
is —CH 2 —.
3 . A process acording to claim 1 , wherein the sterically hindered amines are compounds of formula II, IIa or Iib
R 8 is hydrogen, C 1 -C 25 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 1 -C 20 alkoxy, phenyl-C 1 -C 3 alkyl, C 5 -C 12 cycloalkyl, C 5 -C 8 cycloalkoxy, phenyl, naphthyl, hydroxyethyl, CO—C 1 -C 25 alkyl, CO-phenyl, CO-naphthyl, CO-phenyl-C 1 -C 3 alkyl, O—CO—C 1 -C 20 alkyl or C 1 -C 6 alkyl-S—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-(CO)—C 1 -C 6 alkyl,
w is a number from 1 to 10;
Y is a single bond, C 1 -C 25 alkylene, phenylene, biphenylene, naphthylene, —O—C 1 -C 25 alkylene, —NR 9 —, —O— or
Z is hydrogen, —COOR 9 , —NH 2 , —OR 9 , hydroxyethyl,
R 9 is hydrogen or C 1 -C 12 alkyl;
R 10 has the same definition as R 8 .
4 . A process according to claim 1 , wherein the lactones are compounds of formula III
R 11 , R 12 , R 12a and R 13 are each independently of one another hydrogen, C 1 -C 25 alkyl, phenyl-C 1 -C 3 alkyl, C 5 -C 12 cycloalkyl or phenyl; and
G is OH, OCH 2 CH 2 OH,
or —OCH 2 COOH.
5 . A process according to claim 1 , wherein the sulfides are compounds of formula IV
R 15 S—R 16 (IV),
wherein
R 15 is C 1 -C 18 alkyl, benzyl, phenyl or
and
R 16 is —CH 2 CH 2 OH,
, —CH 2 COOH or —CH 2 CH 2 COOH; and
R 17 is C 1 -C 18 alkyl or unsubstituted or C 1 -C 4 alkyl-substituted phenyl.
6 . A process according to claim 1 , wherein the phosphites are compounds of formula V
R 16a is —CH 2 CH 2 OH or —CH 2 CH 2 COOH; and
R 17a is C 1 -C 18 alkyl or unsubstituted or C 1 -C 4 alkyl-substituted phenyl.
7 . A process according to claim 1 , wherein the benzotriazoles, benzophenones and 2,4,6-triaryl-1,3,5-triazines are compounds of formula VI, VIa, VIb or VIc
R 18 is —(CH 2 ) t —R 20
or NH 2 ;
R 19 is C 1 -C 12 alkyl, α,α-dimethylbenzyl or a radical
R 20 is —OH, —SH, —NHR 30 , —SO 3 H, —COOR 21 , —CH═CH 2 ,
or —(CO)—NH—(CH 2 ) u —NCO;
R 21 is hydrogen,
or —CH 2 —CH(OH)—CH 2 —O—(CO)—R 22 ;
R 22 is C 1 -C 4 alkyl or phenyl;
R 23 and R 24 are each independently of the other hydrogen or C 1 -C 4 alkyl;
R 25 is hydrogen, —(CH 2 ) u —OH,
—(CH 2 ) u COOH or —(CO)—NH—(CH 2 ) u —NCO;
R 26 is hydrogen, OH or C 1 -C 12 alkoxy;
R 27 is hydrogen or OH;
R 28 is hydrogen or
R 29 is hydrogen or halogen;
R 30 is hydrogen or C 1 -C 9 alkyl;
m is 0 or 1;
t is a number from 0 to 6;
u is a number from 2 to 12.
8 . A process according to claim 1 , wherein the compatibiliser compound is a polymer containing acid groups, acid anhydride groups, ester groups, epoxy groups or alcohol groups or wherein the compatibiliser compound is a copolymer or terpolymer of polyethylene, polypropylene, vinyl acetate or styrene with acrylic acid.
9 . A process according to claim 8 , wherein the compatibiliser compound is a polymer with acrylic acid (M) function, glycidyl methacrylate (G MA) function, methacrylic acid (MM) function, maleic anhydride (MAH) function or vinyl alcohol (VA) function.
10 . A process according to claim 8 , wherein the compatibiliser compound is a copolymer consisting of polyethylene acrylic acid (PE-AA),
polyethylene glycidyl methacrylate (PE-GMA), polyethylene methacrylic acid (PE-MAA) or polyethylene maleic anhydride (PE-MAH) or a terpolymer of polyethylene and vinyl acetate with acrylic acid or a terpolymer of polyethylene and acrylates with acrylic acid.
11 . A process according to claim 8 , wherein the compatibiliser compound is a grafted polyethylene or polypropylene copolymer selected from the group consisting of maleic anhydride grafted to polyethylene vinyl acetate (MAH-g-PE-vinyl acetate), maleic anhydride grafted to low density polyethylene (MAH-g-LDPE), maleic anhydride grafted to high density polyethylene (MAH-g-HDPE), maleic anhydride grafted to linear low density polyethylene (MAH-g-LLDPE), acrylic acid grafted to polypropylene (AA-g-PP), glycidyl methacrylate grafted to polypropylene (GMA-g-PP), maleic anhydride grafted to polypropylene (MAH-g-PP), maleic anhydride grafted to ethylene/propylene terpolymer (MAH-g-EPDM), maleic anhydride grafted to ethylene/propylene rubber (MAH-g-EPM) and maleic anhydride grafted to polyethylene/polypropylene copolymer (MAH-g-PE/PP).
12 . A process according to claim 8 , wherein the compatibiliser compound is a grafted styrene co- or terpolymer selected from the group consisting of styrene/acrylonitrile grafted with maleic anhydride (SAN-g-MAH), styrene/maleic anhydride/methyl methacrylate, styrene/butadiene/styrene block copolymer grafted with maleic anhydride (SBS-g-MAH), styrene/ethylene/propylene/styrene block copolymer grafted with maleic anhydride (SEPS-g-MAH), styrene/ethylene/butadiene/styrene block copolymer grafted with maleic anhydride (SEPS-g-MAH) and acrylic acid/polyethylene/polystyrene terpolymer (AA-PE-PS-terpolymer).
13 . A process according to claim 8 , wherein the compatibiliser compound is a vinyl alcohol copolymer.
14 . A process according to claim 1 , wherein the polymers to be stabilised are at least two different polymers.
15 . A process according to claim 1 , wherein the polymers to be stabilised are recycled material.
16 . A compound obtainable by reacting sterically hindered phenols of formula I
R 1 and R 2 are each independently of the other hydrogen, C 1 -C 25 alkyl, phenyl-C 1 -C 3 alkyl which is unsubstituted or substituted once or several times at the aromatic ring by OH or/and C 1 -C 4 alkyl, unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 12 cycloalkyl, or phenyl;
n is 1, 2 or 3;
E is OH, SH, NHR 3 , SO 3 H, COOH, —CH═CH 2 ,
m is 0 or 1;
R 3 is hydrogen or C 1 -C 9 alkyl;
R 4 is C 1 -C 12 alkyl, phenyl which is unsubstituted or substituted by one or several C 1 -C 4 alkyl, halogen or/and C 1 -C 18 alkoxy;
A if E is OH, SH or —CH═CH 2 , is —C x H 2x —, —CH 2 —S—CH 2 CH 2 —, —C q H 2q —(CO)—O—C p H 2p —, —C q H 2q —(CO)—NH—C p H 2p — or —C q H 2q —(CO)—O—C p H 2p —S—C q H 2q —;
x is a number from 0 to 8;
p is a number from 2 to 8;
q is a number from 0 to 3;
R 1 and n are as defined above; or
A if E is —NHR 3 , is —C x H 2x — or —C q H 2q —(CO)—NH—C p H 2p —, wherein x, p and q have the meanings cited above; or
A if E is COOH or SO 3 H, is —C x H 2x —, —CH 2 —S—CH 2 — or —CH 2 —S—CH 2 CH 2 —, wherein x has the meaning cited above; or
A if E is
is a direct bond, —C q H 2q —(CO)—O—CH 2 — or —C x H 2x —S—CH 2 —, wherein q, m, x, R 1 and R 2 are as defined above;
A if E is
is —CH 2 —;
or sterically hindered amines of formula II, IIa or IIb
R 8 is hydrogen, C 1 -C 25 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 1 -C 20 alkoxy, phenyl-C 1 -C 3 alkyl, C 5 -C 12 cycloalkyl, C 5 -C 8 cycloalkoxy, phenyl, naphthyl, hydroxyethyl, CO—C 1 -C 25 alkyl, CO-phenyl, CO-naphthyl, CO-phenyl-C 1 -C 3 alkyl, O—CO—C 1 -C 20 alkyl or C 1 -C 6 alkyl-S—C 1 -C 6 alkyl, C 1 -C 6 alkyl-O—C 1 -C 6 alkyl, C 1 -C 6 alkyl-(CO)—C 1 -C 6 alkyl,
w is a number from 1 to 10;
Y is a single bond, C 1 -C 25 alkylene, phenylene, biphenylene, naphthylene, —O—C 1 -C 25 alkylene, —NR 9 —, —O— or
Z is hydrogen, —COOR 9 , —NH 2 , —OR 9 , hydroxyethyl,
R 9 is hydrogen or C 1 -C 12 alkyl;
R 10 has the same definition as R 8 ;
or lactones of formula III
R 11 , R 12 , R 12a and R 13 are each independently of one another hydrogen, C 1 -C 25 alkyl, phenyl-C 1 -C 3 alkyl, C 5 -C 12 cycloalkyl or phenyl; and
G is OH, OCH 2 CH 2 OH,
or —OCH 2 COOH;
or sulfides of formula IV
R 15 —S—R 16 (IV),
wherein
R 15 is C 1 -C 18 alkyl, benzyl, phenyl or
and
R 16 is —CH 2 CH 2 OH,
—CH 2 COOH or —CH 2 CH 2 COOH; and
R 17 is C 1 -C 18 alkyl or unsubstituted or C 1 -C 4 alkyl-substituted phenyl;
or phosphites of formula V
R 16a is —CH 2 CH 2 OH or —CH 2 CH 2 COOH; and
R 17a is C 1 -C 18 alkyl or unsubstituted or C 1 -C 4 alkyl-substituted phenyl;
or benzotriazoles, benzophenones or 2,4,6-triaryl-1,3,5-triazines of formula VI, VIa, VIb or VIc
R 18 is —(CH 2 ) t —R 20 ,
or NH 2 ;
R 19 is C 1 -C 12 alkyl, α,α-dimethylbenzyl or a radical
R 20 is —OH, —SH, —NHR 30 , —SO 3 H, —COOR 21 , —CH═CH 2 ,
or —(CO)—NH—(CH 2 ) u —NCO;
R 21 is hydrogen,
or —CH 2 —CH(OH)—CH 2 —O—(CO)—R 22 ;
R 22 is C 1 -C 4 alkyl or phenyl;
R 23 and R 24 are each independently of the other hydrogen or C 1 -C 4 alkyl;
R 25 is hydrogen, —(CH 2 ) u —OH,
—(CH 2 ) u COOH or —(CO)—NH—(CH 2 ) u —NCO;
R 26 is hydrogen, OH or C 1 -C 12 alkoxy;
R 27 is hydrogen or OH;
R 28 is hydrogen or
R 29 is hydrogen or halogen;
R 30 is hydrogen or C 1 -C 9 alkyl;
m is 0 or 1;
t is a number from 0 to 6;
u is a number from 2 to 12;
with a compatibiliser compound.
17 . Use of compounds according to claim 16 as stabilisers and at the same time as phase compatibilisers in plastics or plastic compositions.Join the waitlist — get patent alerts
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