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US 4,786,668 AGranted
Resin materials
AssigneeShell Oil Company
InventorKenneth C. Dewhirst
Life of this patent
Estimating the term…
Abstract
The present invention relates to a new thermoplastic polymer composition having the processing characteristics of a thermosetting polymer along with an improved balance of properties including solvent resistance and improved modulus/glass transition temperature/toughness balance. These new polymer compositions are prepared by reacting certain diphenolic compounds with certain diepoxide compounds to form linear units which are lightly crosslinked through the resulting secondary hydroxyl groups. Also disclosed and claimed are processes for preparing such compositions, cured compositions and end-use applications.
Claims59
The composition comprising linear molecules having the repeating structures:
- ##STR27## wherein:
- (a) the segment X comprises stiff units (SU) and optional flexible units (FU) and has the structure --A--Z--Ar-- where Ar is substituted or non-substituted benzene rings, optionally annulated with one or more additional benzene rings, and wherein Z represents a gem-bivalent radical having 1 to 2 aromatic hydrocarbon rings and a gem-bivalent non-aromatic ring selected from the group consisting of a ring of 5 carbon atoms, a ring of 6 carbon atoms, one of which carbon atoms may bear an oxo oxygen atom, and a ring of 5 carbon atoms and one oxygen atom, said gem-bivalent non-aromatic ring being fused to said aromatic hydrocarbon rings;
- (b) "Y" represents a segment comprising stiff units (SU') and optional flexible units (FU') which stiff units and flexible units are interconnected;
- (c) said stiff units, SU and SU', are independently selected from the group consisting of substituted and non-substituted aromatic rings and non-interfering heterocyclic rings;
- (d) said flexible units, FU and FU', are independently selected from the group consisting of ##STR28## (e) the number of "X" segments in said molecules is "a", the number of "Y" segments in said molecules is "b", and the ratio of a/(a+b) is greater than zero and less than or equal to one;
- (f) the number of stiff units and flexible units is selected such that the average number of total stiff units ##EQU8## divided by the average number of total flexible units ##EQU9## is greater than four;
- and (g) the ratio of the number of stiff units to flexible units in said "X" segment (SU/FU) is equal to or greater than the ratio of the number of stiff units to flexible units in said "Y" segment (SU'/FU').
4 more elements
The composition comprising linear molecules having the repeating structures:
- ##STR32## wherein:
- X comprises stiff units (SU) and flexible units (FU) and has the structure:
- ##STR33## and Y has a value of from 0 to 3;
- (b) "Y" represents a segment comprising stiff units (SU') and optional flexible units (FU') which stiff units and flexible units are interconnected;
- (c) said stiff units, SU and SU', are independently selected from the group consisting of substituted and non-substituted aromatic rings and non-interfering heterocyclic rings;
- (d) said flexible units, FU and FU', are independently selected from the group consisting of ##STR34## (e) the number of "X" segments in said molecules is "a", the number of "Y" segments in said molecules is "b", and the ratio of a/(a+b) is greater than zero and less than or equal to one;
- (f) the number of stiff units and flexible units is selected such that the average number of total stiff units ##EQU10## divided by the average number of total flexible units ##EQU11## is greater than four;
- and (g) the ratio of the number of stiff units to flexible units in said "X" segment (SU/FU) is equal to or greater than the ratio of the number of stiff units to flexible units in said "Y" segment (SU'/FU').
5 more elements
The novel composition comprising linear molecules having the repeating structures:
- ##STR35## wherein:
- (a) "X" contains stiff units (SU) and optional flexible units (FU) which stiff and flexible units are interconnected to form a phthalocyanine radical;
- (b) "Y" represents a segment comprising stiff units (SU') and optional flexible units (FU') which stiff units and flexible units are interconnected;
- (c) said stiff units, SU and SU', are independently selected from the group consisting of substituted and non-substituted aromatic rings and non-interfering heterocyclic rings;
- (d) said flexible units, FU and FU', are independently selected from the group consisting of ##STR36## (e) the number of "X" segments in said molecules is "a", the number of "Y" segments in said molecules is "b", and the ratio of a/(a+b) is greater than zero and less than or equal to one;
- (f) the number of stiff units and flexible units is selected such that the average number of total stiff units ##EQU12## divided by the average number of total flexible units ##EQU13## is greater than four;
- and (g) the ratio of the number of stiff units to flexible units in said "X" segment (SU/FU) is equal to or greater than the ratio of the number of stiff units to flexible units in said "Y" segment (SU'/FU').
4 more elements
A novel composition comprising lightly crosslinked linear molecules having the repeating structures prior to crosslinking of the formula:
- ##STR37## where:
- (a) "X" represents a segment comprising stiff units (SU) and optional flexible units (FU), which stiff units and flexible units are interconnected;
- (b) "Y" represents a segment comprising stiff units (SU') and optional flexible units (FU') which stiff units and flexible units are interconnected;
- (c) said stiff units, SU and SU', are independently selected from the group consisting of substituted and non-substituted aromatic rings and non-interfering heterocyclic rings;
- (d) said flexible units, FU and FU', are independently selected from the group consisting of ##STR38## (e) the number of "X" segments in said molecules is "a", the number of "Y" segments in said molecules is "b", and the ratio of a/(a+b) is greater than zero and less than or equal to one;
- (f) the number of stiff units and flexible units is selected such that the average number of total stiff units ##EQU14## divided by the average number of total flexible units ##EQU15## is greater than four;
- and (g) the ratio of the number of stiff units to flexible units in said "X" segment (SU/FU) is equal to or greater than the ratio of the number of stiff units to flexible units in said "Y" segment (SU'/FU');
- and
- (H) wherein said repeating structures are lightly crosslinked such that between 1 and about 50 repeating structures from different molecules per 100 of said repeating structures are crosslinked together.
6 more elements
The process for preparing thermoplastic polymers, said process comprising reacting:
- (a) a first component selected from the group consisting of phenol compounds of the formula HO--X--OH and HO--Y--OH;
- (b) a second component selected from the group consisting of diepoxide compounds of the structures:
- ##STR43## wherein n is 0 to 6 and if the phenol compound is HO--X--OH, then the diepoxide is chosen from the structure of formula III or IV and if the phenol compound is HO--Y--OH, then the diepoxide is chosen from the structure of formula III:
- and
- (c) a catalytic amount of a basic condensation catalyst at an elevated temperature and with a molar ratio of phenol compounds to diepoxides of about 0.90 to about 1.04 until the desired linear reaction product has been formed and thereafter stopping the reaction, wherein in the resulting polymer:
- (i) the segment X comprises stiff units (SU) and optional flexible units (FU) and has the structure --Ar--Z--Ar-- where Ar is substituted or non-substituted benzene rings, optionally annulated with one or more additional benzene rings, and wherein Z represents a gem-bivalent radical having 1 to 2 aromatic hydrocarbon rings and a gem-bivalent non-aromatic ring selected from the group consisting of a ring of 5 carbon atoms, a ring of 6 carbon atoms one of which carbon atoms may bear an oxo atom, and a ring of 5 carbon atoms and one oxygen atom, said gem-bivalent non-aromatic ring being fused to said aromatic hydrocarbon rings;
- (ii) "Y" represents a segment comprising stiff units (SU') and optional flexible units (FU') which stiff units and flexible units are interconnected;
- (iii) said stiff units, SU and SU', are independently selected from the group consisting of substituted and non-substituted aromatic rings, and non-interfering heterocyclic rings;
- (iv) said flexible units, FU and FU', are independently selected from the group consisting of ##STR44## (v) the number of X segments in the resulting polymer is "a", the number of Y segments in the resulting polymer is "b", and the ratio of a/(a+b) is greater than zero and less than or equal to one;
- (vi) the number of stiff units and flexible units are selected such that the average number of total stiff units in the resulting polymer ##EQU16## divided by the average number of total flexible units in the polymer ##EQU17## is greater than four;
- and (vii) the ratio of the number of stiff units to flexible units of said X segment (SU/FU) is equal to or greater than the ratio of the number of stiff units to flexible units in said Y segment (SU'/FU').
8 more elements
The process for preparing thermoplastic polymers, said process comprising reacting:
- (a) a first component selected from the group consisting of phenol compounds of the formula HO--X--OH and HO--Y--OH;
- (b) a second component selected from the group consisting of diepoxide compounds of the structures:
- ##STR48## wherein n is 0 to 6 and if the phenol compound is HO--X--OH, then the diepoxide is chosen from the structure of formula III or IV and if the phenol compound is HO--Y--OH, then the diepoxide is chosen from the structure of formula III:
- and
- (c) a catalytic amount of a basic condensation catalyst at an elevated temperature and with a molar ratio of phenol compounds to diepoxides of about 0.90 to about 1.04 until the desired linear reaction product has been formed and thereafter stopping the reaction, wherein in the resulting polymer:
- (i) the segment X has the structure ##STR49## and "y" has a value of from 0 to 3;
- (ii) "Y" represents a segment comprising stiff units (SU') and optional flexible unit (FU') which stiff units and flexible units are interconnected;
- (iii) said stiff units, SU and SU', are independently selected from the group consisting of substituted and non-substituted aromatic rings, and non-interfering heterocyclic rings;
- (iv) said flexible units, FU and FU', are independently selected from the group consisting of ##STR50## (v) the number of X segments in the resulting polymer is "a", the number of Y segments in the resulting polymer is "b", and the ratio of a/(a+b) is greater than zero and less than or equal to one;
- (vi) the number of stiff units and flexible units are selected such that the average number of total stiff units in the resulting polymer ##EQU18## divided by the average number of total flexible units in the polymer ##EQU19## is greater than four;
- and (vii) the ratio of the number of stiff units to flexible units in said X segment (SU/FU) is equal to or greater than the ratio of the number of stiff units to flexible units in said Y segment (SU'/FU').
8 more elements
A process for preparing lightly crosslinked thermoplastic polymers, said process comprising reacting a first component selected from the group consisting of phenol compounds of the formula HO--X--OH and HO--Y--OH;
- (a) a first component selected from the group consisting of phenol compounds of the formula HO--X--OH and HO--Y--OH;
- (b) a second component selected from the group consisting of diepoxide compounds of the structure:
- ##STR51## wherein n is 0 to 6 and the phenyl compound is HO--X--OH, then the diepoxide is chosen from the structure of formula III or IV and if the phenol compound is HO--Y--OH, then the diepoxide is chosen from the structure of formula III;
- and
- (c) a catalytic amount of a basic condensation catalyst at an elevated temperature and with a molar ratio of phenol compounds to diepoxides of about 0.90 to about 1.04 until the desired linear reaction product has been formed and thereafter stopping the reaction, wherein the resulting polymer is such that:
- (a) "X" represents a segment comprising stiff units (SU) and optional flexible units (FU), which stiff units and flexible units are interconnected;
- (b) "Y" represents a segment comprising stiff units (SU') and optional flexible units (FU') which stiff units and flexible units are interconnected;
- (c) said stiff units, SU and SU', are independently selected from the group consisting of substituted and non-substituted aromatic rings and non-interfering heterocyclic rings;
- (d) said flexible units, FU and FU', are independently selected from the group consisting of ##STR52## (e) the number of "X" segments in said molecules is "a", the number of "Y" segments in said molecules is "b", and the ratio of a/(a+b) is greater than zero and less than or equal to one;
- (f) the number of stiff units and flexible units is selected such that the average number of total stiff units ##EQU20## divided by the average number of total flexible units ##EQU21## is greater than four;
- and (g) the ratio of the number of stiff units to flexible units in said segment "X" (SU/FU) is equal to or greater than the ratio of the number of stiff units to flexible units in said "Y" segment (SU'/FU');
- and
- (h) lightly crosslinking the polymer such that between 1 and about 50 repeating structures from different molecules per 100 of said repeating structures of the polymer are crosslinked together during cure.
10 more elements
Dependencies are inferred from the claim text.