Patent GB-818157-A (GB)
Title: Improvements in linear polyesters and polyesteramides
IPC: C08G63/688
Filed: 1956-04-05
Abstract: New linear polyesters and polyesteramides are obtained by using the compound 1 : 4-cyclohexane dimethanol (CHDM) as the glycol. The substance may be used in its cis-form or transform or as a mixture thereof.  In the preparation of polyesters, the dibasic acid with which the CHDM is condensed may be orthophthalic, terephthalic, isophthalic, hexahydroorthophthalic, transhexahydroterephthalic, p : p1-sulphonyl dibenzoic, 4 : 41-diphenic, 4 : 41-benzophenone dicarboxylic, 1 : 4 - naphthalene dicarboxylic or 1 : 5-naphthalene dicarboxylic acid; also 1 : 2 - di - (p - carboxyphenoxy)ethane, 1 : 2 - di - (p-carboxyphenyl)ethane or 4 : 41-dicarboxydiphenyl ether; also oxalic, carbonic, succinic, adipic, sebacic, azelaic, alpha-ethylsuberic, alpha : alpha - diethyladipic or dimethylmalonic acid; also dicarboxydiethyl ether.  Ester-forming derivatives of the acids may be used, e.g. the alkyl or aryl esters, the acid halides or the anhydrides.  Glycols which may be used in addition to the CHDM are ethylene glycol, 1 : 5-pentanediol, 1 : 10-decanediol, diethylene glycol, triethylene glycol, 2 : 2-dimethyl-1 : 3-propanediol, 2 - methyl - 1 : 5 - pentanediol and 1 : 4-di-(hydroxyethyl)benzene.  As a modifier, hydroxypinalic, hydroxybutyric, hydroxycaproic or p-hydroxybenzoic acid may be used.  In the manufacture of polyesteramides, the CHDM is condensed with a dibasic acid, e.g. one of those specified above, and also a diamine, e.g. hexamethylene diamine, ethylene diamine, benzidine or p-xylylene-a  : a 1-diamine), and/or a hydroxyamine, e.g. 3 - amino - 2 : 2 - dimethylpropanol, hydroxyethylamine, hydroxyoctamethyleneamine or p-xylylene-a -hydroxy-a 1-amine, and/or an aminoacid, e.g. p-aminoethylbenzoic acid, 6-aminocaproic acid, 6-aminohexanoic acid, 7-aminohexanoic acid or 2-methyl-6-aminohexanoic acid. Hydroxyacids may be used as modifiers.  "Block" polyesteramides may be prepared by the processes of U.S.A. Specifications 2,547,113 and 2,691,006.  The polyesters or polyesteramides are useful in the manufacture of fibres, films, supports for photographic emulsions and moulding compositions.  In examples, polyesters are prepared from (1), (2), (7)-(20), (38), (53) CHDM and dimethyl terephthalate; (3), (21)-(36), (37), (39), (40), (41), (43), (44), (45), (54), (55), (59) and (60) CHDM, dimethyl terephthalate and sebacic acid or its dibutyl ester, succinic acid or anhydride, adipic acid, azelaic acid, isophthalic acid or its dibutyl ester, dimethylmalonic acid, hydroxypinalic acid, hexahydroterephthalic acid, the dibutyl or diethyl ester of hexahydroorthophthalic acid or a mixture of alpha-ethyl suberic acid, alpha : alpha1-diethyladipic acid and sebacic acid or its diisobutyl ester; (6) CHDM and the dibutyl ester of p : p1-sulphonyl dibenzoic acid, (4), (5), (49), (50), (51), (52), (61) and (62) CHDM, the dibutyl ester of sulphonyldibenzoic acid and sebacic acid or dibutyl sebacate, succinic anhydride or dibutyl adipate, (42) CHDM and the dimethyl ester of hexahydroterephthalic acid, (46), (47), (48) CHDM, terephthalic acid or its dimethyl ester and 2 : 2-dimethylpropylene glycol, ethylene glycol or 1 : 5-pentanediol, (56) CHDM and diethyl carbonate, (57) CHDM and succinic anhydride, (58) CHDM and dimethyl isophthalate, (63) CHDM and diethyl oxolate.  In further examples polyesteramides are prepared by reacting (64) CHDM, dimethy terephthalate and hexamethylene diamine, (65) CHDM, the dibutyl ester of sulphonyl dibenzoic acid and tetramethylene diamine; (66) CHDM, dimethyl terephthalate and N : N1-bis-(hydroxyethyl)terephthalamide, (67) CHDM and a hexamethylene isophthalamide prepolymer with acid end groups.  Fibres and films may be made from the above polyesters or polyesteramides and may be oriented and heat-set.  In examples: (53) filaments are made by forcing a fused polyester of cyclohexanedimethanol and terephthalic acid through a spinneret and winding on a conventional package; the resulting yarn is then fed over a roller at 120 DEG  C. to a winder revolving at a greater speed, thus drawing it to 3.57 times its original length, and then heated at 165 DEG  C. while holding it at constant length, (54) yarn made from a polyester of cyclohexanedimethanol, terephthalic acid and succinic acid is stretched to 4.67 its original length and heat-set in a similar manner; (55) a polyester of cyclohexanedimethanol, terephthalic acid and isophthalic acid is extruded into film, stretched in mutually perpendicular directions and then heat-set.