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US4328322A
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Synthetic polymers by polyisocyanate polyaddition process
Assignee: Air Products and Chemicals Inc
•
Filing: 1980-09-22
•
Granted: 1982-05-04
•
Expires: 2000-09-22
Abstract
Abstract Synthetic polymers and a process for their preparation by a polyisocyanate polyaddition reaction are described. Synthetic polymers are provided by the reaction of a polyisocyanate with substantially an equivalent amount of an oligomeric para-, meta- or di-meta-aminobenzoic acid ester or amide having the formula <IMAGE> wherein n is an integer of from 2 to 4; each x is one or two; each benzoyl nucleus is para-, meta- or di-meta- amino-substituted; each Z is <IMAGE> and G is an n-valent radical which may be obtained by the removal of hydroxyl or amino groups from an n-valent oligomeric polyol or polyamine having a molecular weight of from about 400 to about 6,000. Useful synthetic polymeric products can be simply and effectively provided by reaction of the polyisocyanate and the oligomeric aminobenzoic acid ester or amide reactants without the requirement of additional curative or chain-extending agents.
Inventors
- 👤 Richard C. Baron
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 13:23
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/50; C08G18/5021; C08G18/5024; C08G18/5027; C08G18/5036; C08G18/5039; C08G18/64
Claims Analysis
Total Claims: 76
Claim 1
Independent Claim
125 words
A synthetic polymer substantially free of the reaction product of an isocyanate and a polyalkylene ether glycol or polyol and substantially free of salts formed during production of the polymer by reaction of a basic material and an amine salt and comprising the reaction product of a polyisocyanate and substantially an equivalent amount of an oligomeric aminobenzoic acid ester or amide having the formula ##STR38## wherein n is an integer from 2 to 4; each x is one or two; each benzoyl nucleus is para-, meta- or di-metaamino-substituted; each Z is ##STR39## and G is an n- valent radical obtained by removal of hydroxy groups or amino groups from an n-valent polyol or polyamine having a molecular weight of from about 400 to about 6,000.
Claim 2
Dependent Claim
125 words
A synthetic polymer substantially free of the reaction product of an isocyanate and a polyalkylene ether glycol or polyol and substantially free of salts formed during production of the polymer by reaction of a basic material and an amine salt and comprising the reaction product of a polyisocyanate and substantially an equivalent amount of an oligomeric aminobenzoic acid ester or amide having the formula ##STR38## wherein n is an integer from 2 to 4; each x is one or two; each benzoyl nucleus is para-, meta- or di-metaamino-substituted; each Z is ##STR39## and G is an n- valent radical obtained by removal of hydroxy groups or amino groups from an n-valent polyol or polyamine having a molecular weight of from about 400 to about 6,000.
Claim 3
Dependent Claim
27 words
The synthetic polymer of claim 1 wherein said polyisocyanate comprises from about 0.9 to about 1.2 equivalents per equivalent of said oligomeric aminobenzoic acid ester or amide.
Claim 4
Dependent Claim
27 words
The synthetic polymer of claim 2 wherein said polyisocyanate comprises from about 1.0 to about 1.15 equivalents per equivalent of said oligomeric aminobenzoic acid ester or amide.
Claim 5
Dependent Claim
52 words
The synthetic polymer of claim 1 wherein said oligomeric aminobenzoic acid or amide has the formula ##STR40## wherein G represents a divalent radical obtained by the removal of two hydroxyl or amino groups from an oligomeric polyol or polyamine having a molecular weight in the range of about 400 to about 6,000.
Claim 6
Dependent Claim
21 words
The synthetic polymer of claim 4 wherein said molecular weight is in the range of from about 650 to about 2,000.
Claim 7
Dependent Claim
40 words
the synthetic polymer of claim 4 wherein each said Z is --O-- and said divalent radical G is obtained by removal of two hydroxyl groups from a polyalkyleneether glycol wherein the alkylene moiety thereof has up to ten carbon atoms.
Claim 8
Dependent Claim
21 words
The synthetic polymer of claim 6 wherein said alkylene moiety of said polyalkyleneether glycol has from two to four carbon atoms.
Claim 9
Dependent Claim
22 words
The synthetic polymer of claim 7 wherein said alkylene moiety is from polytetramethylene ether glycol having a molecular weight of about 1000.
Claim 10
Dependent Claim
13 words
The synthetic polymer of claim 1 in the form of a cast elastomer.
Claim 11
Dependent Claim
13 words
The synthetic polymer of claim 8 in the form of a cast elastomer.
Claim 12
Dependent Claim
13 words
The synthetic polymer of claim 1 in the form of a cellular foam.
Claim 13
Dependent Claim
13 words
The synthetic polymer of claim 8 in the form of a cellular foam.
Claim 14
Dependent Claim
54 words
The synthetic polymer of claim 1 wherein said oligomeric aminobenzoic acid ester or amide has the formula ##STR41## wherein G represents a trivalent radical obtained by the removal of three hydroxyl or amino groups from an oligomeric polyol or polyamine having a molecular weight in the range of from about 400 to about 6,000.
Claim 15
Dependent Claim
21 words
The synthetic polymer of claim 13 wherein said molecular weight is in the range of from about 650 to about 2,000.
Claim 16
Dependent Claim
29 words
The synthetic polymer of claim 13 wherein each said Z is --O-- and said trivalent radical G is obtained by removal of three hydroxyl groups from a polyoxyalkyleneether glycerol.
Claim 17
Dependent Claim
21 words
The synthetic polymer of claim 15 wherein said alkylene moiety of said polyoxyalkyleneether glycol has from two to four carbon atoms.
Claim 18
Dependent Claim
22 words
The synthetic polymer of claim 16 wherein said alkylene moiety is from polytetramethylene ether glycol having a molecular weight of about 1000.
Claim 19
Dependent Claim
13 words
The synthetic polymer of claim 17 in the form of a cast elastomer.
Claim 20
Dependent Claim
13 words
The synthetic polymer of claim 17 in the form of a cellular foam.
Claim 21
Dependent Claim
13 words
The synthetic polymer of claim 1 wherein said polyisocyanate comprises a liquid polyisocyanate.
Claim 22
Dependent Claim
13 words
The synthetic polymer of claim 20 wherein said liquid polyisocyanate includes 4,4'-diphenylmethane diisocyanate.
Claim 23
Dependent Claim
25 words
The synthetic polymer of claim 20 wherein said liquid polyisocyanate includes a polymeric polyisocyanate having from about 4 to about 15 isocyanate groups per molecule.
Claim 24
Dependent Claim
121 words
The synthetic polymer of claim 1 which comprises the reaction product of a polyisocyanate and substantially an equivalent amount of a mixture of oligomeric aminobenzoic acid esters, said mixture comprising a di-(4-aminobenzoate) ester having the formula ##STR42## wherein G represents a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of about 400 to about 6,000; and from about 1% to about 50% by weight of said di-(4-aminobenzoate) ester, of a di-(3-aminobenzoate) ester having the formula ##STR43## wherein G represents a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 400 to about 6,000.
Claim 25
Dependent Claim
40 words
The synthetic polymer of claim 23 wherein each said G is a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 650 to about 2,000.
Claim 26
Dependent Claim
26 words
The synthetic polymer of claim 23 wherein each said G is a divalent radical obtained by the removal of two hydroxyl groups from a polyoxyalkyleneether glycol.
Claim 27
Dependent Claim
121 words
The synthetic polymer of claim 1 which comprises the reaction product of a polyisocyanate and substantially an equivalent amount of a mixture of oligomeric aminobenzoic acid esters, said mixture comprising a di-(4-aminobenzoate)ester having the formula ##STR44## wherein G represents a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 400 to about 6,000; and from about 1% to about 15% by weight of said di-(4-aminobenzoate) ester, of a di-(3,5-diaminobenzoate) ester having the formula ##STR45## wherein G represents a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 400 to about 6,000.
Claim 28
Dependent Claim
40 words
The synthetic polymer of claim 26 wherein each said G is a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 650 to about 2,000.
Claim 29
Dependent Claim
26 words
The synthetic polymer of claim 26 wherein each said G is a divalent radical obtained by the removal of two hydroxyl groups from a polyalkyleneether glycol.
Claim 30
Dependent Claim
121 words
The synthetic polymer of claim 1 which comprises the reaction product of a polyisocyanate and substantially an equivalent amount of a mixture of oligomeric p-aminobenzoic acid esters, said mixture comprising a di-(p-aminobenzoate) ester having the formula ##STR46## wherein G represents a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of about 400 to about 6,000; and from about 1% to about 20% by weight of said di-(p-aminobenzoate) ester, of a tri-(p-aminobenzoate) ester having the formula ##STR47## wherein G represents a trivalent radical obtained by the removal of three hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 400 to about 6,000.
Claim 31
Dependent Claim
107 words
A process for preparing a synthetic polymer from a reaction mixture substantially free of polyalkylene ether glycols or polyols and acidic reaction rate-controlling amine salt-forming agents, said process comprising reacting a polyisocyanate with substantially an equivalent amount of an oligomeric p-aminobenzoic acid or amide having the formula ##STR48## wherein n is an integer 2 to 4; each x is one or two; each benzoyl nucleus is para-, meta-, or di-meta- amino-substituted; each Z is ##STR49## and G is an n-valent radical obtained by removal of hydroxyl groups or amino groups from an n-valent polyol or polyamine having a molecular weight of from about 400 to about 6,000.
Claim 32
Dependent Claim
107 words
A process for preparing a synthetic polymer from a reaction mixture substantially free of polyalkylene ether glycols or polyols and acidic reaction rate-controlling amine salt-forming agents, said process comprising reacting a polyisocyanate with substantially an equivalent amount of an oligomeric p-aminobenzoic acid or amide having the formula ##STR48## wherein n is an integer 2 to 4; each x is one or two; each benzoyl nucleus is para-, meta-, or di-meta- amino-substituted; each Z is ##STR49## and G is an n-valent radical obtained by removal of hydroxyl groups or amino groups from an n-valent polyol or polyamine having a molecular weight of from about 400 to about 6,000.
Claim 33
Dependent Claim
26 words
The process of claim 30 wherein said polyisocyanate comprises from about 0.9 to about 1.2 equivalents per equivalent of said oligomeric aminobenzoic acid ester of amide.
Claim 34
Dependent Claim
26 words
The process of claim 31 wherein said polyisocyanate comprises from about 1.0 to about 1.15 equivalents per equivalent of said oligomeric aminobenzoic acid ester or amide.
Claim 35
Dependent Claim
52 words
The process of claim 31 wherein said oligomeric aminobenzoic acid ester or amide has the formula ##STR50## wherein G represents a divalent radical obtained by the removal of two hydroxyl or amino groups from an oligomeric polyol or polyamine having a molecular weight in the range of about 400 to about 6,000.
Claim 36
Dependent Claim
20 words
The process of claim 33 wherein said molecular weight is in the range of from about 650 to about 2,000.
Claim 37
Dependent Claim
39 words
The process of claim 33 wherein each said Z is --O-- and said divalent radical G is obtained by removal of two hydroxyl groups from a polyalkyleneether glycol wherein the alkylene moiety thereof has up to ten carbon atoms.
Claim 38
Dependent Claim
20 words
The process of claim 35 wherein said alkylene moiety of said polyalkyleneether glycol has from two to four carbon atoms.
Claim 39
Dependent Claim
21 words
The process of claim 36 wherein said alkylene moiety is from polytetramethylene ether glycol having a molecular weight of about 1000.
Claim 40
Dependent Claim
13 words
The process of claim 30 wherein said reaction mixture includes a blowing agent.
Claim 41
Dependent Claim
53 words
The process of claim 30 wherein said oligomeric aminobenzoic acid ester or amide has the formula ##STR51## wherein G represents a trivalent radical obtained by the removal of three hydroxyl or amino groups from an oligomeric polyol or polyamine having a molecular weight in the range of from about 400 to about 6,000.
Claim 42
Dependent Claim
28 words
The process of claim 39 wherein each said Z is --O-- and said trivalent radical G is obtained by removal of three hydroxyl groups from a polyoxyalkyleneether glycerol.
Claim 43
Dependent Claim
20 words
The process of claim 40 wherein said alkylene moiety of said polyoxyalkyleneether glycol has from two or four carbon atoms.
Claim 44
Dependent Claim
22 words
The process of claim 41 wherein each said alkylene moiety is from polytetramethylene ether glycol having a molecular weight of about 1000.
Claim 45
Dependent Claim
13 words
The process of claim 42 wherein said reaction mixture includes a blowing agent.
Claim 46
Dependent Claim
12 words
The process of claim 30 wherein said polyisocyanate comprises a liquid polyisocyanate.
Claim 47
Dependent Claim
11 words
The process of claim 44 wherein said polyisocyanate comprises 4,4'-diphenylmethane diisocyanate.
Claim 48
Dependent Claim
24 words
The process of claim 44 wherein said liquid polyisocyanate comprises a polymeric polyisocyanate having from about 4 to about 15 isocyanate groups per molecule.
Claim 49
Dependent Claim
117 words
The process of claim 30 which comprises reacting said polyisocyanate with substantially an equivalent amount of a mixture of oligomeric aminobenzoic acid esters, said mixture comprising a di-(4-aminobenzoate) ester having the formula ##STR52## wherein G represents a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of about 400 to about 6,000; and from about 1% to about 50% by weight of said di-(4-aminobenzoate ester), of a di-(3-aminobenzoate) ester having the formula ##STR53## wherein G represents a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 400 to about 6,000.
Claim 50
Dependent Claim
39 words
The process of claim 47 wherein each said G is a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 650 to about 2,000.
Claim 51
Dependent Claim
25 words
The process of claim 47 wherein each said G is a divalent radical obtained by the removal of two hydroxyl groups from a polyoxyalkyleneether glycol.
Claim 52
Dependent Claim
118 words
The process of claim 30 which comprises reacting said polyisocyanate with substantially an equivalent amount of a mixture of oligomeric aminobenzoic acid esters, said mixture comprising a di-(4-aminobenzoate) ester having the formula ##STR54## wherein G represents a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 400 to about 6,000; and from about 1% to about 15% by weight of said di-(4-aminobenzoate) ester, of a di-(3,5-diaminobenzoate) ester having the formula ##STR55## wherein G represents a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 400 to about 6,000.
Claim 53
Dependent Claim
39 words
The process of claim 50 wherein each said G is a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 650 to about 2,000.
Claim 54
Dependent Claim
25 words
The process of claim 50 wherein each said G is a divalent radical obtained by the removal of two hydroxyl groups from a polyalkyleneether glycol.
Claim 55
Dependent Claim
106 words
The process of claim 30 wherein said oligomeric aminobenzoic acid ester comprises a mixture of a di-(p-aminobenzoate) ester having the formula ##STR56## wherein G represents a divalent radical obtained by the removal of two hydroxyl groups from an oligomeric polyol having a molecular weight in the range of about 400 to about 6,000; and from about 1% to about 20% by weight of said di-(aminobenzoate) ester, of a tri-(aminobenzoate) ester having the formula ##STR57## wherein G represents a trivalent radical obtained by the removal of three hydroxyl groups from an oligomeric polyol having a molecular weight in the range of from about 400 to about 6,000.
Claim 56
Dependent Claim
90 words
A synthetic polymer which consists essentially of the reaction product of a polyisocyanate and substantially an equivalent amount of an oligomeric aminobenzoic acid ester or amide having the formula ##STR58## wherein n is an integer from 2 to 4; each x is one or two; each benzoyl nucleus is para-, meta- or di-meta- amino-substituted; each Z is ##STR59## and G is an n-valent radical obtained by removal of hydroxy groups or amino groups from an n-valent polyol or polyamine having a molecular weight of from about 400 to about 6,000.
Claim 57
Dependent Claim
90 words
A synthetic polymer which consists essentially of the reaction product of a polyisocyanate and substantially an equivalent amount of an oligomeric aminobenzoic acid ester or amide having the formula ##STR58## wherein n is an integer from 2 to 4; each x is one or two; each benzoyl nucleus is para-, meta- or di-meta- amino-substituted; each Z is ##STR59## and G is an n-valent radical obtained by removal of hydroxy groups or amino groups from an n-valent polyol or polyamine having a molecular weight of from about 400 to about 6,000.
Claim 58
Dependent Claim
27 words
The synthetic polymer of claim 1 wherein said polyisocyanate comprises from about 0.9 to about 1.2 equivalents per equivalent of said oligomeric aminobenzoic acid ester or amide.
Claim 59
Dependent Claim
27 words
The synthetic polymer of claim 54 wherein said polyisocyanate comprises from about 1.0 to about 1.15 equivalents per equivalent of said oligomeric aminobenzoic acid ester or amide.
Claim 60
Dependent Claim
53 words
The synthetic polymer of claim 54 wherein said oligomeric aminobenzoic acid ester or amide has the formula ##STR60## wherein G represents a divalent radical obtained by the removal of two hydroxyl or amino groups from an oligomeric polyol or polyamine having a molecular weight in the range of about 400 to about 6,000.
Claim 61
Dependent Claim
21 words
The synthetic polymer of claim 57 wherein said molecular weight is in the range of from about 650 to about 2,000.
Claim 62
Dependent Claim
40 words
The synthetic polymer of claim 57 wherein each said Z is --O-- and said divalent radical G is obtained by removal of two hydroxyl groups from a polyalkyleneether glycol wherein the alkylene moiety thereof has up to ten carbon atoms.
Claim 63
Dependent Claim
21 words
The synthetic polymer of claim 59 wherein said alkylene moiety of said polyalkyleneether glycol has from two to four carbon atoms.
Claim 64
Dependent Claim
22 words
The synthetic polymer of claim 60 wherein said alkylene moiety is from polytetramethylene ether glycol having a molecular weight of about 1000.
Claim 65
Dependent Claim
13 words
The synthetic polymer of claim 54 in the form of a cast elastomer.
Claim 66
Dependent Claim
13 words
The synthetic polymer of claim 54 in the form of a cellular foam.
Claim 67
Dependent Claim
94 words
A process for preparing a synthetic polymer which comprises reacting a mixture which consists essentially of a polyisocyanate and substantially an equivalent amount of an oligomeric aminobenzoic acid or amide having the formula ##STR61## wherein n is an integer from 2 to 4; each x is one or two; each benzoyl nucleus is para-, meta- or di-meta- amino-substituted; each Z is ##STR62## and G is an n-valent radical obtained by removal of hydroxy groups or amino groups from an n-valent polyol or polyamine having a molecular weight of from about 400 to about 6,000.
Claim 68
Dependent Claim
94 words
A process for preparing a synthetic polymer which comprises reacting a mixture which consists essentially of a polyisocyanate and substantially an equivalent amount of an oligomeric aminobenzoic acid or amide having the formula ##STR61## wherein n is an integer from 2 to 4; each x is one or two; each benzoyl nucleus is para-, meta- or di-meta- amino-substituted; each Z is ##STR62## and G is an n-valent radical obtained by removal of hydroxy groups or amino groups from an n-valent polyol or polyamine having a molecular weight of from about 400 to about 6,000.
Claim 69
Dependent Claim
26 words
The process of claim 64 wherein said polyisocyanate comprises from about 0.9 to about 1.2 equivalents per equivalent of said oligomeric aminobenzoic acid ester or amide.
Claim 70
Dependent Claim
26 words
The process of claim 65 wherein said polyisocyanate comprises from about 1.0 to about 1.15 equivalents per equivalent of said oligomeric aminobenzoic acid ester or amide.
Claim 71
Dependent Claim
52 words
The process of claim 65 wherein said oligomeric aminobenzoic acid ester or amide has the formula ##STR63## wherein G represents a divalent radical obtained by the removal of two hydroxyl or amino groups from an oligomeric polyol or polyamine having a molecular weight in the range of about 400 to about 6,000.
Claim 72
Dependent Claim
20 words
The process of claim 64 wherein said molecular weight is in the range of from about 650 to about 2,000.
Claim 73
Dependent Claim
39 words
The process of claim 64 wherein each said Z is --O-- and said divalent radical G is obtained by removal of two hydroxyl groups from a polyalkyleneether glycol wherein the alkylene moiety thereof has up to ten carbon atoms.
Claim 74
Dependent Claim
20 words
The process of claim 69 wherein said alkylene moiety of said polyalkyleneether glycol has from two to four carbon atoms.
Claim 75
Dependent Claim
21 words
The process of claim 70 wherein said alkylene moiety is from polytetramethylene ether glycol having a molecular weight of about 1,000.
Claim 76
Dependent Claim
13 words
The process of claim 64 wherein said reaction mixture includes a blowing agent.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-05-03 | 1985-11-02 | 1986-05-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-05-03 | 1989-11-02 | 1990-05-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-05-03 | 1993-11-02 | 1994-05-04 | $7700.00 | Window Closed / Lapsed |