US4599397A — Wholly aromatic polyester and process for produci…

Claim 1

Independent Claim 191 words

A wholly aromatic polyester consisting essentially of structural units represented by the formulae (A), (B), (C), (D) and (E): ##STR9## wherein R 1 represents a halogen atom, a hydrocarbon group, an alkoxy group or a phenoxy group, ##STR10## wherein A represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylene group or an alkylidene group, or a single bond directly connecting the two benzene rings and R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 represent respectively a hydrogen atom, a halogen atom or a hydrocarbon group, the wholly aromatic polyester containing 5 to 50 mol % of the unit (A), 5 to 45 mol % of the unit (B), 5 to 45 mol % of the unit (C), 5 to 20 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) being substantially equimolar.

Claim 2

Dependent Claim 191 words

A wholly aromatic polyester consisting essentially of structural units represented by the formulae (A), (B), (C), (D) and (E): ##STR9## wherein R 1 represents a halogen atom, a hydrocarbon group, an alkoxy group or a phenoxy group, ##STR10## wherein A represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylene group or an alkylidene group, or a single bond directly connecting the two benzene rings and R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 represent respectively a hydrogen atom, a halogen atom or a hydrocarbon group, the wholly aromatic polyester containing 5 to 50 mol % of the unit (A), 5 to 45 mol % of the unit (B), 5 to 45 mol % of the unit (C), 5 to 20 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) being substantially equimolar.

Claim 3

Dependent Claim 94 words

The wholly aromatic polyester according to claim 1, wherein said wholly aromatic polyester contains 30 to 45 mol % of the unit (A), 8 to 30 mol % of the unit (B), 25 to 40 mol % of the unit (C), 8 to 15 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) is substantially equimolar.

Claim 4

Dependent Claim 32 words

The wholly aromatic polyester according to claim 1, wherein structural unit (C) is formed from methylhydroquinone, ethylhydroquinone, n-propylhydroquinone, isopropylhydroquinone, isobutylhydroquinone, chlorohydroquinone, fluorohydroquinone, bromohydroquinone, iodohydroquinone, phenylhydroquinone, methoxyhydroquinone, or phenoxyhydroquinone as a monomer reactant.

Claim 5

Dependent Claim 35 words

The wholly aromatic polyester according to claim 1, wherein structural unit (E) is formed from 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3-chlorophenyl)propane, bis(4-hydroxyphenyl)methane, bis(4-hydroxy-3,5-dimethylphenyl)methane, bis(4-hydroxy-3,5-dichlorophenyl)methane, bis(4-hydroxy-3,5-dibromophenyl)methane, 1,1-bis(4-hydroxydiphenyl)cyclohexane, 4,4'-dihydroxydiphenylbis(4-hydroxyphenyl)ketone, bis(4-hydroxy-3,5-dimethylphenyl)ketone, bis(4-hydroxy-3,5-dichlorophenyl)ketone, bis(4-hydroxyphenyl)sulfide, bis(4-hydroxy-3-chlorophenyl)sulfide, bis(4-hydroxy-3,5-dichlorophenyl)sulfide, bis(4-hydroxyphenyl)sulfone, bis(4-hydroxy-3,5-dichlorophenyl)ether, or 4,4'-dihydroxybiphenyl.

Claim 6

Dependent Claim 55 words

The wholly aromatic polyester according to claim 1, wherein said polyester has a melt viscosity of at least 5×10 3 poise at 350° C. and at a shearing velocity of 1×10 2 sec -1 when tested on a KOKA flow tester having a nozzle of 1 mm in diameter and a length of 10 mm.

Claim 7

Dependent Claim 224 words

A process for producing a wholly aromatic polyester consisting essentially of units represented by the formulae (A), (B), (C), (D) and (E): ##STR11## wherein R 1 represents a halogen atom, a hydrocarbon group, an alkoxy group or a phenoxy group, ##STR12## wherein A represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylene group or an alkylidene group or a single bond directly connecting the two benzene rings, the wholly aromatic polyester containing 5 to 50 mol % of the unit (A), 5 to 45 mol % of the unit (B), 5 to 45 mol % of the unit (C), 5 to 20 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) being substantially equimolar, which process comprises: melt polymerizing (i) terephthalic acid, terephthaloyl dichloride or an alkyl terephthalate compounds, (ii) isophthalic acid, isophthaloyl dichloride or an alkyl isophthalate compound, (iii) an acylated 2-substituted hydroquinone compound, (iv) an acylated 1,4-naphthalenediol compound and optionally (v) a compound of the formula: ##STR13## at a temperature of 250° to 350° C.; and removing the volatile product produced as a result of the polymerization reaction.

Claim 8

Dependent Claim 224 words

A process for producing a wholly aromatic polyester consisting essentially of units represented by the formulae (A), (B), (C), (D) and (E): ##STR11## wherein R 1 represents a halogen atom, a hydrocarbon group, an alkoxy group or a phenoxy group, ##STR12## wherein A represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylene group or an alkylidene group or a single bond directly connecting the two benzene rings, the wholly aromatic polyester containing 5 to 50 mol % of the unit (A), 5 to 45 mol % of the unit (B), 5 to 45 mol % of the unit (C), 5 to 20 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) being substantially equimolar, which process comprises: melt polymerizing (i) terephthalic acid, terephthaloyl dichloride or an alkyl terephthalate compounds, (ii) isophthalic acid, isophthaloyl dichloride or an alkyl isophthalate compound, (iii) an acylated 2-substituted hydroquinone compound, (iv) an acylated 1,4-naphthalenediol compound and optionally (v) a compound of the formula: ##STR13## at a temperature of 250° to 350° C.; and removing the volatile product produced as a result of the polymerization reaction.

Claim 9

Dependent Claim 92 words

The process according to claim 6, wherein said wholly aromatic polyester contains 30 to 45 mol % of the unit (A), 8 to 30 mol % of the unit (B), 25 to 40 mol % of the unit (C), 8 to 15 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) is substantially equimolar.

Claim 10

Dependent Claim 14 words

The process according to claim 6, wherein the unit (C) is derived from methylhydroquinone.

Claim 11

Dependent Claim 16 words

The process according to claim 6, wherein the unit (E) is derived from 2,2-bis(4-hydroxyphenyl)propane or 4,4'-dihydroxydiphenyl.

Claim 12

Dependent Claim 218 words

A process for producing a wholly aromatic polyester consisting essentially of structural units represented by the formulae (A), (B), (C), (D) and (E): ##STR14## wherein R 1 represents a halogen atom, a hydrocarbon group, an alkoxy group or a phenoxy group, ##STR15## wherein A represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylene group or an alkylidene group or a single bond directly connecting the two benzene rings, the wholly aromatic polyester containing 5 to 50 mol % of the unit (A), 5 to 45 mol % of the unit (B), 5 to 45 mol % of the unit (C), 5 to 20 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) being substantially equimolar, which process comprises: dissolving (i) terephthaloyl dichloride, (ii) isophthaloyl dichloride, (iii) a 2-substituted hydroquinone compound or an acylated 2-substituted hydroquinone compound, (iv) a 1,4-naphthalenediol or an acylated 1,4-naphthalenediol compound and optionally (v) a compound of the formula: ##STR16## or a compound of the formula: ##STR17## in an organic solvent: and heating the solution containing the monomers to effect polycondensation.

Claim 13

Dependent Claim 218 words

A process for producing a wholly aromatic polyester consisting essentially of structural units represented by the formulae (A), (B), (C), (D) and (E): ##STR14## wherein R 1 represents a halogen atom, a hydrocarbon group, an alkoxy group or a phenoxy group, ##STR15## wherein A represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylene group or an alkylidene group or a single bond directly connecting the two benzene rings, the wholly aromatic polyester containing 5 to 50 mol % of the unit (A), 5 to 45 mol % of the unit (B), 5 to 45 mol % of the unit (C), 5 to 20 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) being substantially equimolar, which process comprises: dissolving (i) terephthaloyl dichloride, (ii) isophthaloyl dichloride, (iii) a 2-substituted hydroquinone compound or an acylated 2-substituted hydroquinone compound, (iv) a 1,4-naphthalenediol or an acylated 1,4-naphthalenediol compound and optionally (v) a compound of the formula: ##STR16## or a compound of the formula: ##STR17## in an organic solvent: and heating the solution containing the monomers to effect polycondensation.

Claim 14

Dependent Claim 18 words

The process according to claim 10 wherein said organic solvent is a chlorinated hydrocarbon or an aromatic hydrocarbon.

Claim 15

Dependent Claim 92 words

The process according to claim 10, wherein said wholly aromatic polyester contains 30 to 45 mol % of the unit (A), 8 to 30 mol % of the unit (B), 25 to 40 mol % of the unit (C), 8 to 15 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) is substantially equimolar.

Claim 16

Dependent Claim 14 words

The process according to claim 10, wherein the unit (C) is derived from methylhydroquinone.

Claim 17

Dependent Claim 16 words

The process according to claim 10, wherein the unit (E) is derived from 2,2-bis(4-hydroxyphenyl)propane or 4,4'-dihydroxydiphenyl.

Claim 18

Dependent Claim 226 words

A process for producing a wholly aromatic polyester consisting essentially of units represented by the formulae (A), (B), (C), (D), and (E): ##STR18## wherein R 1 represents a halogen atom, a hydrocarbon group, an alkoxy group or a phenoxy group, ##STR19## wherein A represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylene group or an alkylidene group or a single bond directly connecting the two benzene rings, the wholly aromatic polyester containing 5 to 50 mol % of the unit (A), 5 to 45 mol % of the unit (B), 5 to 45 mol % of the unit (C), 5 to 20 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) being substantially equimolar, which process comprises: interfacially condensing (i) a solution of terephthaloyl dichloride, and isophthaloyl dichloride in an organic solvent and (ii) an aqueous alkaline solution of a 2-substituted hydroquinone compound or an acylated 2-substituted hydroquinone compound, 1,4-naphthalenediol or an acylated 1,4-naphthalenediol compound and optionally a compound of the formula: ##STR20## or a compound of the formula: ##STR21## at a temperature less than 50° C.; and isolating the polymer product.

Claim 19

Dependent Claim 226 words

A process for producing a wholly aromatic polyester consisting essentially of units represented by the formulae (A), (B), (C), (D), and (E): ##STR18## wherein R 1 represents a halogen atom, a hydrocarbon group, an alkoxy group or a phenoxy group, ##STR19## wherein A represents an oxygen atom, a sulfur atom, a sulfonyl group, a carbonyl group, an alkylene group or an alkylidene group or a single bond directly connecting the two benzene rings, the wholly aromatic polyester containing 5 to 50 mol % of the unit (A), 5 to 45 mol % of the unit (B), 5 to 45 mol % of the unit (C), 5 to 20 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) being substantially equimolar, which process comprises: interfacially condensing (i) a solution of terephthaloyl dichloride, and isophthaloyl dichloride in an organic solvent and (ii) an aqueous alkaline solution of a 2-substituted hydroquinone compound or an acylated 2-substituted hydroquinone compound, 1,4-naphthalenediol or an acylated 1,4-naphthalenediol compound and optionally a compound of the formula: ##STR20## or a compound of the formula: ##STR21## at a temperature less than 50° C.; and isolating the polymer product.

Claim 20

Dependent Claim 61 words

The process according to claim 15, wherein the alkali component of said aqueous solution is NaOH, KOH, LiOH, Na 2 CO 3 or K 2 CO 3 , and the amount of said alkali is about twice the molar content of monomers in the aqueous solution and the aqueous solution being a 1 to 15% by weight solution of the alkali.

Claim 21

Dependent Claim 24 words

The process of claim 15, wherein the concentration of acid chloride monomers in the organic solvent solution ranges from 2 to 30% by weight.

Claim 22

Dependent Claim 92 words

The process according to claim 15, wherein said wholly aromatic polyester contains 30 to 45 mol % of the unit (A), 8 to 30 mol % of the unit (B), 25 to 40 mol % of the unit (C), 8 to 15 mol % of the unit (D) and 0 to 10 mol % of the unit (E), and the sum of the amounts of the unit (A) and the unit (B) and the sum of the amounts of the unit (C), the unit (D) and the unit (E) is substantially equimolar.

Claim 23

Dependent Claim 14 words

The process according to claim 15, wherein the unit (C) is derived from methylhydroquinone.

Claim 24

Dependent Claim 16 words

The process according to claim 15, wherein the unit (E) is derived from 2,2-bis(4-hydroxyphenyl)propane or 4,4'-dihydroxydiphenyl.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1989-07-07	1990-01-06	1990-07-08	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1993-07-07	1994-01-06	1994-07-08	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1997-07-07	1998-01-06	1998-07-08	$7700.00	Window Closed / Lapsed

Wholly aromatic polyester and process for producing the same

Abstract

Inventors

Bibliographic Details

Claims Analysis

References Cited (Backward Citations)

USPTO Annuity & Maintenance Windows

Assigned Categories & Tags

Assign Category Tag