Patent GB-885492-A (GB)
Title: Interpolyesters of bibenzoic acid
Inventor: LYTTON MARION R
IPC: C08G63/185
Filed: 1959-08-10
Abstract: New linear copolyesters, suitable for the manufacture of films, fibres, moulded objects and coatings contain the residues of (1) Bibenzoic acid (2) A cyclic acid having the general formula (a) <FORM:0885492/IV (a)/1> wherein <FORM:0885492/IV (a)/2> and Ar and Ar1 are the same of different mono- or polynuclear arylene radicals, R is a straight or branched chain aliphatic hydrocarbon radical containing 1 to 20 carbon atoms or an arylene radical Ar or Ar1 as defined above, m, m1, n, n1 and p are 0-6, with the proviso that m, m1, n and n1 are 0 only when Z is -Ar-X-(RX)p-Ar1- and X is an ether oxygen atom or a sulphone radical; or (b) HOOC-(CH2)m-Ar-(CH2)n-COOH wherein m and n are 0-8 and Ar is a monovalent arylene radical, a fused-ring p  polynuclear arylene radical or the radical -Ar1-R-Ar1- wherein Ar is the same as Ar defined above and R is a straight or branched-chain aliphatic hydrocarbon radical containing 1-10 carbon atoms or an alicyclic radical containing 4-6 nuclear carbon atoms, all of the bivalent aromatic or alicyclic radicals being either non-substituted or substituted by alkyl radicals containing 1-8 carbon atoms; or <FORM:0885492/IV (a)/3> wherein Al is an alicyclic hydrocarbon radical containing 4-12 nuclear carbon atoms, g, h and j are 0-8 and k is 0 or 1 and  (3) A glycol selected from one of the groups (A)-(F) below; the interpolyester containing at least 30 mol. per cent of bibenzoic acid.  The glycols have the general formula (A) HO-R-OH wherein R1 is a straight- or branched-chain aliphatic hydrocarbon radical containing 2-20 carbon atoms (which may be saturated or unsaturated);  (B) HO-(R1X)n-R1OH wherein R1 is a straight- or branched-chain aliphatic hydrocarbon radical containing 2-10 carbon atoms, X is an ether oxygen atom or a sulphone radical and n is 1-6;  (C) HO-(CH2)m-Ar-(CH2)m-OH wherein Ar is a mono- or di-nuclear aromatic hydrocarbon radical containing 6-12 nuclear carbon atoms and m is 1-4; <FORM:0885492/IV (a)/4> wherein R1, X and n are the same as in (B), Ar is the same as in (C), and p is 0-4; (E) HO(CH2)o-R11-(CH2)o-OH wherein R11 is an alicyclic hydrocarbon radical containing 4-6 nuclear carbon atoms and p is the same as in (D), or  <FORM:0885492/IV (a)/5> wherein R1, X and n is the same as in (B), p is the same as in (D) and R11 is the same as in (E).  A large number of suitable dicarboxylic acids and glycol are specified. Polyesterification may be effected by heating the acids (or dialkyl esters or di- and chloride thereof) with the glycol. Examples disclose the making of polyesters by condensing (1)-(10), (21), (24)-(27), (29), (39)-(43), (46)-(47), (51) Diethyl bibenzoate, ethylene glycol and diethyl homopinate, diethyl pinate, dimethyl hexahydroterephthalate, the dimethyl ester of bicyclo [2.2.1] heptane-2,3-dicarboxylic acid, the diethyl ester of p. p1-pentamethylene-dioxybibenzoic acid, the diethyl ester of 1,4-bis-(p-phenoxy) butane, the diethyl ester of 4,41-dicarboxyldiphenyl ether, the dibutyl ester of sulphonyl-bis-(p-carboxybenzene), the diethyl ester of bis-(p-carboxyphenoxy)-methane, dimethyl terephthalate, the diethyl ester of 2,6-dicarboxynaphthalene or dimethyl isophthalate; (11), (18), (32), (37), (44) and (45) Diethyl bibenzoate, diethylene glycol and diethyl pinate, dimethyl hexahydroterephthalate, the diethyl ester of 1,4-bis-(p-carboxyphenoxy) butane, the dibutyl ester of sulphonyl-bis-(p-carboxybenzene), dimethyl isophthalate or dimethyl terephthalate; (12), (16), (30), (34) and (52) Diethyl bibenzoate, hexamethylene glycol and diethyl pinate, dimethyl hexahydroterephthalate, the dibutyl ester of sulphonyl-bis-(p-carboxybenzene), the diethyl ester of 1,4-bis-(p-carboxyphenoxy) butane or dimethyl isophthalate; (13)-(15), (28), (33), (48) and (50) Diethyl bibenzoate, reopentylene glycol and diethyl pinate, dimethyl hexahydroterephthalate, the diethyl ester of 1,4-bis-(p-carboxyphenoxy) butane, the dibutyl ester of sulphonyl-bis-(p-carboxybenzene), dimethyl terephthalate, or dimethyl isophthalate; (17), (31) and (49) Diethyl bibenzoate, decamethylene glycol and dimethyl hexahydroterephthalate, the dibutyl ester of sulphonyl-bis-(p-carboxybenzene) or dimethyl terephthalate; (22) Diethyl bibenzoate, triethylene glycol and dimethyl hexahydroterephthalate; (23), (36) and (53) Bibenzoyl chloride, 2,21-(p-phenylenedioxy)-diethanol and pinoyl chloride, the acid chloride of 1,4-bis-(p-carboxyphenoxy)-butane or terephthaloyl chloride; (20), (35) and (54) Bibenzoyl chloride, p-xylylene glycol and pinoyl chloride, the diacid chloride of 1,4-bis-(p-carboxyphenoxy) -butane or terephthaloyl chloride; (19), (38) and (55) Bibenzoyl chloride, cis-1,4-quinitol and pinoyl chloride the diacid chloride of 1,4-bis-(p-carboxyphenoxy)-butane or terephthaloyl chloride.