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US4053441A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydantoin polyamide-poly(oxyethylene) block copolymers as antistatic additives for polyamides

Assignee: Akzona Inc
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Filing: 1976-11-29
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Granted: 1977-10-11
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Expires: 1996-11-29
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Abstract

Abstract This invention relates to hydantoin polyamide-poly(oxyethylene) block copolymers which have good thermal stability and an increased hydrophilicity of the polyamide blocks, and which can be used as an additive to polyamides, resulting in improved antistatic properties of the polyamides. The formula for a typical copolymer is: ##STR1## IN WHICH X IS 2 TO 5, Y IS ABOUT 23, AND Z IS 2 TO 3.

Inventors

  • 👤 Kenneth Boone Wagener
  • 👤 Bron Walter Spivey, Jr.
  • 👤 James Mood Chapman, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 06:54
CPC Classifications
C; C08; C08L; C08L77/00; C08G; C08G69/00

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 271 words
An antistatic yarn polymer additive composition consisting essentially of a hydantoin polyamide-poly(oxyethylene) block copolymer comprising the reaction product of a hydroxyterminated poly(oxyethylene) having a number average molecular weight of about 200 to about 4000, with a prepolymer comprising the reaction product of a first compound having the structural formula: ##STR15## wherein R 1 and R 2 are alkyl groups containing from 1 to 6 carbon atoms and P is COOH or CH 2 NH 2 , with a second compound from the group consisting of piperazine or a compound having the following structural formula: Q -- R.sub.5 -- Q where if the second compound is piperazine, P is COOH; and if the second compound is Q--R 5 --Q, when P is COOH, Q may be NH 2 or CH 2 NH 2 , when Q is NH 2 ,R 5 can be a straight chain alkylene radical of 3 to 12 carbon atoms, a branched chain alkylene radical of up to 36 carbon atoms, an alicyclic radical or a radical having the following structural formula: ##STR16## where R 3 and R 4 are alkyl groups containing from 1 to 6 carbon atoms and when Q is CH 2 NH 2 , R 5 can be of the above or an aromatic radical; and when P is NH 2 or CH 2 NH 2 , Q is COOH, and R 5 is selected from the group consisting of a straight chain alkylene radical of 2 to 12 carbon atoms, a branched chain alkylene radical of up to 36 carbon atoms, an aromatic radical and a radical having the structural formula III above.
Claim 2
Dependent Claim 271 words
An antistatic yarn polymer additive composition consisting essentially of a hydantoin polyamide-poly(oxyethylene) block copolymer comprising the reaction product of a hydroxyterminated poly(oxyethylene) having a number average molecular weight of about 200 to about 4000, with a prepolymer comprising the reaction product of a first compound having the structural formula: ##STR15## wherein R 1 and R 2 are alkyl groups containing from 1 to 6 carbon atoms and P is COOH or CH 2 NH 2 , with a second compound from the group consisting of piperazine or a compound having the following structural formula: Q -- R.sub.5 -- Q where if the second compound is piperazine, P is COOH; and if the second compound is Q--R 5 --Q, when P is COOH, Q may be NH 2 or CH 2 NH 2 , when Q is NH 2 ,R 5 can be a straight chain alkylene radical of 3 to 12 carbon atoms, a branched chain alkylene radical of up to 36 carbon atoms, an alicyclic radical or a radical having the following structural formula: ##STR16## where R 3 and R 4 are alkyl groups containing from 1 to 6 carbon atoms and when Q is CH 2 NH 2 , R 5 can be of the above or an aromatic radical; and when P is NH 2 or CH 2 NH 2 , Q is COOH, and R 5 is selected from the group consisting of a straight chain alkylene radical of 2 to 12 carbon atoms, a branched chain alkylene radical of up to 36 carbon atoms, an aromatic radical and a radical having the structural formula III above.
Claim 3
Dependent Claim 35 words
The composition of claim 1 where the second compound is Q--R 5 --Q, P is CH 2 NH 2 , and R 5 is a straight chain alkylene radical of 2 to 12 carbon atoms.
Claim 4
Dependent Claim 31 words
The composition of claim 1 where the second compound is Q--R 5 --Q, P is COOH, and R 5 is a straight chain alkylene radical of 3 to 12 carbon atoms.
Claim 5
Dependent Claim 25 words
The composition of claim 1 where the second compound is Q--R 5 --Q, P is CH 2 NH 2 , and R 5 is ##STR17##
Claim 6
Dependent Claim 21 words
The composition of claim 1 where said poly (oxyethylene) has a number average molecular weight of about 600 to about 1500.
Claim 7
Dependent Claim 18 words
The composition of claim 1 where said poly (oxyethylene) has a number average molecular weight of about 1,000.
Claim 8
Dependent Claim 28 words
The composition of claim 6 where R 1 and R 2 are CH 3 , P is CH 2 NH 2 and the second compound is adipic acid.
Claim 9
Dependent Claim 40 words
The composition of claim 6 where R 1 and R 2 are CH 3 , P is COOH, the second compound is Q--R 5 --Q, and R 3 and R 4 are CH 3 , and R 5 is ##STR18##
Claim 10
Dependent Claim 24 words
The composition of claim 6 where R 1 and R 2 are CH 3 , P is COOH and the second compound is piperazine.
Claim 11
Dependent Claim 51 words
The composition of claim 6 where R 1 and R 2 are CH 3 , P is CH 2 NH 2 , the second compound is Q--R 5 --Q, and R 5 is a branched chain hydrocarbon, C 34 H 68 , which is the hydrogenated dimerization product of oleic acid.
Claim 12
Dependent Claim 132 words
A hydantoin polyamide block copolymer having the following formula: ##STR19## where x is 2 to 5, y is about 5 to 90 and z is 2 to 3, and where R 8 is --OH or --O(CH 2 CH 2 O) y H, R 9 is --H or ##STR20## one of R 6 and R 7 is a radical having one of the following structural formulas ##STR21## and the other of R 6 and R 7 is selected from the group consisting of straight chain alkylene radicals of 2 to 12 carbon atoms, branched chain alkylene radicals of up to 36 carbon atoms, aromatic radicals, alicyclic radicals, or radicals having one of the following structural formulas: ##STR22## where R 1 and R 2 are alkyl groups containing from 1 to 6 carbon atoms.
Claim 13
Dependent Claim 132 words
A hydantoin polyamide block copolymer having the following formula: ##STR19## where x is 2 to 5, y is about 5 to 90 and z is 2 to 3, and where R 8 is --OH or --O(CH 2 CH 2 O) y H, R 9 is --H or ##STR20## one of R 6 and R 7 is a radical having one of the following structural formulas ##STR21## and the other of R 6 and R 7 is selected from the group consisting of straight chain alkylene radicals of 2 to 12 carbon atoms, branched chain alkylene radicals of up to 36 carbon atoms, aromatic radicals, alicyclic radicals, or radicals having one of the following structural formulas: ##STR22## where R 1 and R 2 are alkyl groups containing from 1 to 6 carbon atoms.
Claim 14
Dependent Claim 32 words
The copolymer of clain 11 where R 6 is (CH 2 ) 4 , R 7 is ##STR23## R 1 and R 2 are CH 3 , and y is about 23.
Claim 15
Dependent Claim 32 words
The copolymer of clain 11 where R 6 is (CH 2 ) 4 , R 7 is ##STR23## R 1 and R 2 are CH 3 , and y is about 23.
Claim 16
Dependent Claim 27 words
The copolymer of claim 11 where R 6 and R 7 are ##STR24## R 1 and R 2 are CH 3 , and y is about 23.
Claim 17
Dependent Claim 31 words
The copolymer of claim 11 where R 6 has the formula ##STR25## R 7 is "T", and R 1 and R 2 are CH 3 , and y is about 23.
Claim 18
Dependent Claim 45 words
The copolymer of claim 11 where R 6 is a branched chain hydrocarbon, C 34 H 68 , which is the hydrogenated dimerization product of oleic acid, R 7 is ##STR26## R 1 and R 2 are CH 3 , and y is about 23.
Claim 19
Dependent Claim 29 words
A polymer blend composition suitable for meltshaping comprising a polyamide and an antistatic hydantoin polyamide-poly (oxyethylene) block copolymer yarn additive having the formula of the copolymer of claim 1.
Claim 20
Dependent Claim 26 words
A polymer blend composition suitable for meltshaping comprising a polyamide, and a hydantoin, polyamide-poly (oxyethylene) block copolymer having the formula of the copolymer of claim 11.
Claim 21
Dependent Claim 26 words
A polymer blend composition suitable for meltshaping comprising a polyamide, and a hydantoin, polyamide-poly (oxyethylene) block copolymer having the formula of the copolymer of claim 12.
Claim 22
Dependent Claim 23 words
A fiber comprising a polyamide having uniformly dispersed therein fibrils of a hydantoin polyamide-poly (oxyethylene) block copolymer having the formula of claim 1.
Claim 23
Dependent Claim 23 words
A fiber comprising a polyamide having uniformly dispersed therein fibrils of a hydantoin polyamide-poly (oxyethylene) block copolymer having the formula of claim 11.
Claim 24
Dependent Claim 23 words
A fiber comprising a polyamide having uniformly dispersed therein fibrils of a hydantoin polyamide-poly (oxyethylene) block copolymer having the formula of claim 12.

References Cited (Backward Citations)

US3384681A Cited
US3549724A Cited
US3514498A Cited
US3632666A Cited
US3636135A Cited
US3839245A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-10-10 1981-04-11 1981-10-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-10-10 1985-04-11 1985-10-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-10-10 1989-04-11 1989-10-11 $7700.00 Window Closed / Lapsed

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