Patent US4581396A successfully refreshed from Google Patents.
US4581396A
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Flame retardants and compositions containing them
Assignee: Albemarle Corp
•
Filing: 1968-09-18
•
Granted: 1986-04-08
•
Expires: 1988-09-18
Abstract
Abstract Flame retardants having good stability at the processing temperatures of high melting polymers are described. The flame retardants are halogen-containing bis-imides, for example, those of the formula ##STR1## R and X being defined in the specification.
Inventors
- 👤 Joseph Sonnenberg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 10:21
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07D209/56; C07D209/58; C07D209/70; C07D209/72; C07D209/76; C07D487/00; C07D487/02; C07D487/04; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3415; C08K5/3417
Claims Analysis
Total Claims: 61
Claim 1
Independent Claim
56 words
A composition comprising a flammable material and a chlorine-containing bisimide of the formula: ##STR5## wherein R is ##STR6## wherein each X is independently, hydrogen or chlorine with at least four X's being chlorine, n is 0-2, p is 0-1; and R' is ##STR7## where n=2-18 with the proviso that when p is O, R' is ##STR8##
Claim 2
Dependent Claim
56 words
A composition comprising a flammable material and a chlorine-containing bisimide of the formula: ##STR5## wherein R is ##STR6## wherein each X is independently, hydrogen or chlorine with at least four X's being chlorine, n is 0-2, p is 0-1; and R' is ##STR7## where n=2-18 with the proviso that when p is O, R' is ##STR8##
Claim 3
Dependent Claim
35 words
A composition comprising a flammable material and a compound of the formula ##STR9## in which R is selected from the group consisting of C 2 -C 4 alkylene, phenylene and ##STR10## where Z is oxygen.
Claim 4
Dependent Claim
35 words
A composition comprising a flammable material and a compound of the formula ##STR9## in which R is selected from the group consisting of C 2 -C 4 alkylene, phenylene and ##STR10## where Z is oxygen.
Claim 5
Dependent Claim
47 words
A composition comprising a flammable material and a compound of the formula ##STR11## in which R is selected from the group consisting of C 2 -C 4 alkylene, phenylene and ##STR12## wherein Z is oxygen and X is hydrogen or chlorine, at least 4 X's being chlorine.
Claim 6
Dependent Claim
47 words
A composition comprising a flammable material and a compound of the formula ##STR11## in which R is selected from the group consisting of C 2 -C 4 alkylene, phenylene and ##STR12## wherein Z is oxygen and X is hydrogen or chlorine, at least 4 X's being chlorine.
Claim 7
Dependent Claim
83 words
A composition of matter comprising a polymer and a chloroaryl imide of a polychloro-substituted polyhydropolycyclicdicarboxylic acid having the formula: ##STR13## in which A, X, and Y are independently selected from the group consisting of hydrogen or chlorine, at least one A and two X's being chlorine; Z is selected from the group consisting of oxygen, sulfur, amino and lower alkyl radicals; m is an integer of from 1 to 2; n ranges from 0 to 2; and p ranges from 0 to 1.
Claim 8
Dependent Claim
83 words
A composition of matter comprising a polymer and a chloroaryl imide of a polychloro-substituted polyhydropolycyclicdicarboxylic acid having the formula: ##STR13## in which A, X, and Y are independently selected from the group consisting of hydrogen or chlorine, at least one A and two X's being chlorine; Z is selected from the group consisting of oxygen, sulfur, amino and lower alkyl radicals; m is an integer of from 1 to 2; n ranges from 0 to 2; and p ranges from 0 to 1.
Claim 9
Dependent Claim
44 words
The composition of matter as set forth in claim 4 in which said chloroaryl imide of a polychloro-substituted polyhydropolycyclicdicarboxylic acid is present in said composition of matter in a range of from about 5% to about 50% by weight of the composition of matter.
Claim 10
Dependent Claim
28 words
The composition of matter as set forth in claim 4 in which said polymer compound is polypropylene and said haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid is α,α'-bis(5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8-methano-2,3-naphthalenedicarboximido)-2,3,5,6-tetrachloro-p-xylene.
Claim 11
Dependent Claim
29 words
The composition of matter as set forth in claim 4 in which said polymer compound is polyphenyl oxide and said haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid is α,α'-bis(5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8-methano-2,3-naphthalenedicarboximido)-2,3,5,6-tetrachloro-p-xylene.
Claim 12
Dependent Claim
31 words
The composition of matter as set forth in claim 4 in which said polymer compound is an epoxy resin and said haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid is 4,4'-bis(5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8-methano-2,3-naphthalenedicarboximidomethyl)-2,2'3,3',5,5',6,6'-octachlorodiphenyl ether.
Claim 13
Dependent Claim
29 words
The composition of matter as set forth in claim 4 in which said polymer compound is acrylonitrilebutadiene-styrene terpolymer and said haloaryl imide of a polyhalo-substituted polyhydropolycyclicidicarboxylic acid is 4,4'-bis(1,4,5,6,7,7-hexachlorobicyclo-[2.2.1]-5-heptene-2,3-dicarboximidomethyl)-2,2',3,3',5,5',6,6'-octachlorodiphenylamine.
Claim 14
Dependent Claim
73 words
A composition of matter comprising a polymer and a haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid having the formula: ##STR14## in which A, X, and Y are independently selected from the group consisting of hydrogen or halogen, at least one A and two X's being halogen; Z is selected from the group consisting of oxygen, sulfur, amino and lower alkyl radicals; m is 1; n is 0; and p is 0 or 1.
Claim 15
Dependent Claim
73 words
A composition of matter comprising a polymer and a haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid having the formula: ##STR14## in which A, X, and Y are independently selected from the group consisting of hydrogen or halogen, at least one A and two X's being halogen; Z is selected from the group consisting of oxygen, sulfur, amino and lower alkyl radicals; m is 1; n is 0; and p is 0 or 1.
Claim 16
Dependent Claim
43 words
The composition of matter as set forth in claim 4 in which said haloaryl imide of polyhalo-substituted polyhydropolycyclicdicarboxylic acid is present in said composition of matter in a range of from about 5% to about 40% by weight of the composition of matter.
Claim 17
Dependent Claim
36 words
The composition of matter as set forth in claim 4 in which said polymer compound is polypropylene and said haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid is selected from the group consisting of α,α'-bis[5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8-methano-2,3-naphtalene-dicarboximido]-2,3,5,6-tetrachloro-p-xylene and α,α'-bis(1,4,5,6,7,7-hexachlorobicyclo-[2.2.1]-5-heptene-2,3-dicarboximido)-2,3,5,6-tetrachloro-p-xylene.
Claim 18
Dependent Claim
37 words
The composition of matter as set forth in claim 4 in which said polymer compound is polypropylene and said haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid is selected from the group consisting of α,α'-bis[5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8-methano-2,3-naphtahalene-dicarboximido]-2,3,5,6-tetrachloro-p-xylene, α,α'-bis(1,4,5,6,7,7-hexachlorobicyclo-[2.2.1]-5-heptene-2,3-dicarboximido)-2,3,5,6-tetrachloro-p-xylene, and α,α'-bis(1,4,5,6,7,7-hexachlorobicyclo-[2.2.1]-5-heptene-2,3-dicarboximido)-2,4,5,6-tetrachloro-m-xylene.
Claim 19
Dependent Claim
22 words
The composition of matter as set forth in claim 4 in which said haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid is α,α'-bis(5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8-methano-2,3-naphthalenedicarboximido)-2,3,5,6-tetrachloro-p-xylene.
Claim 20
Dependent Claim
30 words
The composition of matter as set forth in claim 4 in which said haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid is selected from the group consisting of α,α'-bis[5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8-methano-2,3-naphthalene-dicarboximido]-2,3,5,6-tetrachloro-p-xylene and α,α'-bis(1,4,5,6,7,7-hexachlorobicyclo-[2.2.1]-5-heptene-2,3-dicarboximido)-2,3,5,6-tetrachloro-p-xylene.
Claim 21
Dependent Claim
31 words
The composition of matter as set forth in claim 4 in which said haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid is selected from the group consisting of α,α'-bis[5,6,7,8,9,9-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8-methano-2,3-naphthalene-dicarboximido]-2,3,5,6-tetrachloro-p-xylene, α,α'-bis(1,4,5,6,7,7-hexachlorobicyclo-[2.2.1]-5-heptene-2,3-dicarboximido)-2,3,5,6-tetrachloro-p-xylene, and α,α'-bis(1,4,5,6,7,7-hexachlorobicyclo-[2.2.1]-5-heptene-2,3-dicarboximido)-2,4,5,6-tetrachloro-m-xylene.
Claim 22
Dependent Claim
30 words
The composition of matter as set forth in claim 1 in which said polymer compound is a styrene copolymer and said haloaryl imide of a polyhalo-substituted polyhydropolycyclicdicarboxylic acid is α,α'-bis(5,6,7,8,9,9,-hexachloro-1,2,3,4,4a,5,8,8a-octahydro-5,8-methano-2,3-naphtalenedicarboximido)-2,3,5,6-tetrachloro-p-xylene.
Claim 23
Dependent Claim
136 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing from about 0.5 to about 10 weight percent of an antimony-containing compound and from about 5 to about 50 weight percent of an imide of a halogen substituted polyhydrocyclicdicarboxylic acid having the formula: ##STR15## in which X is halogen or hydrogen, at least two X's being halogen; Y is halogen or hydrogen; m is 1 to 2; n ranges from 0 to 2; R is selected from the group consisting of hydrogen and monovalent R'; and R' is selected from the group consisting of alkyl and aminoalkyl of from 1 to 20 carbon atoms, polyalkenepolyamino, aryl, haloaryl, alkoxyaryl, polyarylenepolyamino of from 1 to 3 carbocyclic rings, and aminocyclopolyalkyl and polyalkenepolyamino having from 4 to 8 carbon atoms on the ring.
Claim 24
Dependent Claim
136 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing from about 0.5 to about 10 weight percent of an antimony-containing compound and from about 5 to about 50 weight percent of an imide of a halogen substituted polyhydrocyclicdicarboxylic acid having the formula: ##STR15## in which X is halogen or hydrogen, at least two X's being halogen; Y is halogen or hydrogen; m is 1 to 2; n ranges from 0 to 2; R is selected from the group consisting of hydrogen and monovalent R'; and R' is selected from the group consisting of alkyl and aminoalkyl of from 1 to 20 carbon atoms, polyalkenepolyamino, aryl, haloaryl, alkoxyaryl, polyarylenepolyamino of from 1 to 3 carbocyclic rings, and aminocyclopolyalkyl and polyalkenepolyamino having from 4 to 8 carbon atoms on the ring.
Claim 25
Dependent Claim
13 words
The flame retardant composition of claim 18 in which said halogen is chlorine.
Claim 26
Dependent Claim
13 words
The flame retardant composition of claim 18 in which said halogen is bromine.
Claim 27
Dependent Claim
15 words
The flame retardant composition of claim 18 in which said antimony-containing compound is antimony trioxide.
Claim 28
Dependent Claim
115 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing from about 0.5 to about 25 weight percent of an antimony-containing compound and from about 5 to about 37.5 weight percent of an imide of a halogen substituted polyhydrocyclicdicarboxylic acid having the formula: ##STR16## in which X is halogen or hydrogen, at least two X's being halogen; Y is halogen or hydrogen; m is 1; n is 0 and R' is selected from the group consisting of alkyl of from 1 to 20 carbon atoms, polyalkenepolyamino, aryl, haloaryl, alkoxyaryl, polyarylenepolyamino of from 1 to 3 carbocyclic rings and polyalkenepolyamino having from 4 to 8 carbon atoms on the ring.
Claim 29
Dependent Claim
115 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing from about 0.5 to about 25 weight percent of an antimony-containing compound and from about 5 to about 37.5 weight percent of an imide of a halogen substituted polyhydrocyclicdicarboxylic acid having the formula: ##STR16## in which X is halogen or hydrogen, at least two X's being halogen; Y is halogen or hydrogen; m is 1; n is 0 and R' is selected from the group consisting of alkyl of from 1 to 20 carbon atoms, polyalkenepolyamino, aryl, haloaryl, alkoxyaryl, polyarylenepolyamino of from 1 to 3 carbocyclic rings and polyalkenepolyamino having from 4 to 8 carbon atoms on the ring.
Claim 30
Dependent Claim
13 words
The flame retardant composition of claim 22 in which said halogen is chlorine.
Claim 31
Dependent Claim
13 words
The flame retardant composition of claim 22 in which said halogen is bromine.
Claim 32
Dependent Claim
15 words
The flame retardant composition of claim 22 in which said antimony-containing compound is antimony trioxide.
Claim 33
Dependent Claim
41 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing an antimony-containing compound and an amide selected from the group consisting of ##STR17## wherein X is chlorine and wherein R' is a divalent organic radical.
Claim 34
Dependent Claim
41 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing an antimony-containing compound and an amide selected from the group consisting of ##STR17## wherein X is chlorine and wherein R' is a divalent organic radical.
Claim 35
Dependent Claim
33 words
A flame retardant composition according to claim 26 containing from about 0.5 to about 25% by weight of said antimony compound and from about 5 to about 37.5% by weight of said imide.
Claim 36
Dependent Claim
52 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing an antimony-containing compound and an imide selected from the group consisting of ##STR18## wherein X is chlorine and wherein R' is selected from the group consisting of alkyl and aminoalkyl, polyalkenepolyamino, aryl, haloaryl, alkoxyaryl and aminocyclopolyalkyl.
Claim 37
Dependent Claim
52 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing an antimony-containing compound and an imide selected from the group consisting of ##STR18## wherein X is chlorine and wherein R' is selected from the group consisting of alkyl and aminoalkyl, polyalkenepolyamino, aryl, haloaryl, alkoxyaryl and aminocyclopolyalkyl.
Claim 38
Dependent Claim
33 words
A flame retardant composition according to claim 28 containing from about 0.5 to about 25% by weight of said antimony compound and from about 5 to about 37.5% by weight of said imide.
Claim 39
Dependent Claim
38 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing an antimony-containing compound and an imide of the formula ##STR19## wherein X is chlorine and wherein R' is a divalent organic radical.
Claim 40
Dependent Claim
38 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing an antimony-containing compound and an imide of the formula ##STR19## wherein X is chlorine and wherein R' is a divalent organic radical.
Claim 41
Dependent Claim
33 words
A flame retardant composition according to claim 30 containing from about 0.5 to about 25% by weight of said antimony compound and from about 5 to about 37.5% by weight of said imide.
Claim 42
Dependent Claim
49 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing an antimony-containing compound and an imide of the formula ##STR20## wherein X is chlorine and wherein R' is selected from the group consisting of alkyl and aminoalkyl, polyalkenepolyamino, aryl, haloaryl, alkoxyaryl and aminocyclopolyalkyl.
Claim 43
Dependent Claim
49 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing an antimony-containing compound and an imide of the formula ##STR20## wherein X is chlorine and wherein R' is selected from the group consisting of alkyl and aminoalkyl, polyalkenepolyamino, aryl, haloaryl, alkoxyaryl and aminocyclopolyalkyl.
Claim 44
Dependent Claim
33 words
A flame retardant composition according to claim 32 containing from about 0.5 to about 25% by weight of said antimony compound and from about 5 to about 37.5% by weight of said imide.
Claim 45
Dependent Claim
60 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing an antimony-containing compound and an imide selected from the group consisting of ##STR21## in which x is chlorine or hydrogen, at least two x's being chlorine, and R' is selected from the group consisting of alkyl and aminoalkyl, polyalkenepolyamino, aryl, haloaryl, alkoxyaryl and aminocyclopolyalkyl.
Claim 46
Dependent Claim
60 words
A flame retardant composition of matter selected from the group consisting of polyolefins and ABS containing an antimony-containing compound and an imide selected from the group consisting of ##STR21## in which x is chlorine or hydrogen, at least two x's being chlorine, and R' is selected from the group consisting of alkyl and aminoalkyl, polyalkenepolyamino, aryl, haloaryl, alkoxyaryl and aminocyclopolyalkyl.
Claim 47
Dependent Claim
12 words
A composition as claimed in claim 1 wherein each X is chlorine.
Claim 48
Dependent Claim
14 words
A composition as claimed in claim 1 wherein said flammable material is a polymer.
Claim 49
Dependent Claim
12 words
A composition as claimed in claim 36 wherein said polymer is polyethylene.
Claim 50
Dependent Claim
12 words
A composition as claimed in claim 36 wherein said polymer is polypropylene.
Claim 51
Dependent Claim
14 words
A composition as claimed in claim 36 wherein said polymer is an acrylonitrile-butadiene-styrene polymer.
Claim 52
Dependent Claim
14 words
A composition as claimed in claim 36 wherein said polymer is an ethylene-propylene copolymer.
Claim 53
Dependent Claim
13 words
A composition as claimed in claim 36 wherein said polymer is poly(1,12-dodecamethylene pyromellitimide).
Claim 54
Dependent Claim
27 words
A composition as claimed in claim 36 wherein the composition contains up to about 40% by weight of the bis-imide, based on the weight of the polymer.
Claim 55
Dependent Claim
13 words
A composition as claimed in claim 36 wherein the polymer is irradiation crosslinked.
Claim 56
Dependent Claim
27 words
A composition as claimed in claim 36 wherein the composition contains from 10% to 30% by weight of the bis-imide, based on the weight of the polymer.
Claim 57
Dependent Claim
18 words
A composition comprising a flammable material, a halogen-containing bis-imide and a compound of an element of Group V.
Claim 58
Dependent Claim
18 words
A composition comprising a flammable material, a halogen-containing bis-imide and a compound of an element of Group V.
Claim 59
Dependent Claim
14 words
A composition as claimed in claim 45 wherein said compound is an antimony compound.
Claim 60
Dependent Claim
14 words
A composition as claimed in claim 46 wherein said antimony compound is antimony oxide.
Claim 61
Dependent Claim
30 words
A composition as claimed in claim 45 wherein the total weight of the halogen-containing bis-imide and the Group V compound is at most 40% of the weight of the composition.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-04-07 | 1989-10-07 | 1990-04-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-04-07 | 1993-10-07 | 1994-04-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-04-07 | 1997-10-07 | 1998-04-08 | $7700.00 | Window Closed / Lapsed |