US4138545A
Expired / Lapsed
US
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Oxazolidine-terminated polyesters
Assignee: Rohm and Haas Co
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Filing: 1978-01-04
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Granted: 1979-02-06
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Expires: 1998-01-04
Abstract
Abstract Disclosed are polyfunctional oxazolidine-terminated polyesters of the general formula: ##STR1## WHEREIN Z" is the residue of a polyester having a plurality of terminal ##STR2## groups, the polyester being the condensation product of organic acids and alcohols of the formulae ##STR3## AND R 4 (OH) p , in which o is 2 or 3 and p is 2 to 4, each of o and p preferably being 2; R 1 and R 2 are hydrogen, C 1 -C 4 alkyl, phenyl, benzyl, or collectively C 5 -C 6 cycloalkylene, preferably hydrogen; R 3 is a covalent bond, a C 1 -C 10 residue of an aliphatic or aromatic polycarboxylic acid, preferably C 1 -C 10 alkylidene; R 4 is the residue of a polyol having 2-15 carbon atoms, preferably C 2 -C 10 alkylidene; X and Y are selected from the radicals (--CH 2 --) 2 and (--CH 2 --) 3 , preferably (--CH 2 --) 2 ; n is an integer having a value of at least 2, preferably no more than about 8; The acid moieties being present in an amount of from 2 to about 12 units and the alcohol moieties numbering from 1 to about 11, with the proviso that said polyesters terminated with a plurality of oxazolidine groups provide a useable viscosity for coatings in the formulations in which they are used, suitably produced by means of a transesterification reaction between a hydroxy oxazolidine, a polycarboxylic acid ester in which the carboxyl groups are esterified by a C 1 -C 4 alkanol such as methanol, and a polyol. The oxazolidine-terminated polyesters are useful in preparing or formulating moisture-curable mixtures with polyfunctional isocyanates, preferably having two --NCO groups, but compounds having three or more such groups being useful, for coatings, caulks, impregnants, adhesives for textiles, leather, plastics, wood, and metals, and binding agents for pigments, fibers and nonwoven fabrics. The approximate Mw is suitably between 600 and 5000 and the approximate Mn is suitably between 400 and 3000 as determined by gel permeation chromatography.
Inventors
- 👤 William D. Emmons
- 👤 Travis E. Stevens
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 12:28
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/68; C08G63/685; C08G63/6854; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/46; C08G18/4615; C08G18/4638; C08G18/4646; C09; C09D; C09D167/00; C09D167/02
Claims Analysis
Total Claims: 41
Claim 1
Independent Claim
19 words
A hydrocurable composition comprising (1) a polyester terminated with a plurality of oxazolidine groups and (2) a polyfunctional isocyanate.
Claim 2
Dependent Claim
19 words
A hydrocurable composition comprising (1) a polyester terminated with a plurality of oxazolidine groups and (2) a polyfunctional isocyanate.
Claim 3
Dependent Claim
191 words
The composition of claim 1 in which the polyester has the general formula: ##STR28## wherein Z" is the residue of a polyester having a plurality of terminal ##STR29## groups, the polyester being the condensation product of organic acids and alcohols of the formulae ##STR30## and R 4 (OH) p , in which o is 2 or 3 and p is 2 to 4; R 1 and R 2 are hydrogen, C 1 -C 4 alkyl, phenyl, benzyl, or collectively, C 5 -C 6 cycloalkylene; R 3 is a covalent bond, a C 1 -C 10 residue of an aliphatic or aromatic polycarboxylic acid/ R 4 is the residue of a polyol having 2-15 carbon atoms; X and Y are selected from the radicals (--CH 2 --) 2 and --(--(CH 2 --) 3 ; and n is an integer having a value of at least 2; the acid moieties being present in an amount of from 2 to about 12 units and the alcohol moieties numbering from 1 to about 11, with the proviso that said oxazolidine-terminated polyesters provide a useable viscosity for coatings in the formulations in which they are used.
Claim 4
Dependent Claim
36 words
The composition of claim 2 in which the polyester is of a diol and a dicarboxylic acid, between 2 moles and 6 moles of acid moieties being present, and n is no more than about 8.
Claim 5
Dependent Claim
52 words
The composition of claim 3 in which the acids and diols are aliphatic, and the isocyanate has two or three --NCO groups, wherein: o and p are each 2, R 1 and R 2 are hydrogen, X and Y are --(CH 2 --) 2 , and n is from 2 to 4.
Claim 6
Dependent Claim
56 words
The composition of claim 3 in which the acid is aromatic and the diol is aliphatic, and the isocyanate has two or three, --NCO groups. wherein o and p are each 2, R 1 and R 2 are hydrogen, X and Y are --(CH 2 --) 2 , and n is from 2 to about 8.
Claim 7
Dependent Claim
49 words
The composition of claim 3 in which n is from Z to about 4, the acid moiety is adipic, terephthalic, isophthalic, phthalic, or azelaic and the diol is 1,4-butanediol, dipropylene glycol, neopentyl glycol, ethylene glycol, diethylene glycol, 1,3; -butylene glycol, and 1,6-hexanediol. and the isocynate has two --NCO groups.
Claim 8
Dependent Claim
188 words
A polyfunctional oxazolidine-terminated polyester of the general formula: ##STR31## wherein Z" is the residue of a polyester having a plurality of terminal ##STR32## groups, the polyester being the condensation product of organic acids and alcohols of the formulae ##STR33## and R 4 (OH) p , in which o is 2 or 3 and p is 2 to 4; R 1 and R 2 are hydrogen, C 1 -C 4 alkyl, phenyl or benzyl; R 3 is a covalent bond, a C 1 -C 10 alkyl or cycloalkyl, or phenyl; R 4 is a C.sub. -C 10 alkyl or cycloalkyl, or the residue of a poly(C 2 -C 3 )glycol having 2-15 carbon atoms; X and Y are selected from the radicals (--CH 2 --) 2 and --(--CH 2 --) 3; and n is an integer having a value of at least 2; the acid moieties being present in an amount of from 2 to about 12 units and the alcohiol moieties numbering from 1 to about 11, with the proviso that said oxazolidine-terminated polyesters provide a useable viscosity for coatings in the formulations in which they are used.
Claim 9
Dependent Claim
188 words
A polyfunctional oxazolidine-terminated polyester of the general formula: ##STR31## wherein Z" is the residue of a polyester having a plurality of terminal ##STR32## groups, the polyester being the condensation product of organic acids and alcohols of the formulae ##STR33## and R 4 (OH) p , in which o is 2 or 3 and p is 2 to 4; R 1 and R 2 are hydrogen, C 1 -C 4 alkyl, phenyl or benzyl; R 3 is a covalent bond, a C 1 -C 10 alkyl or cycloalkyl, or phenyl; R 4 is a C.sub. -C 10 alkyl or cycloalkyl, or the residue of a poly(C 2 -C 3 )glycol having 2-15 carbon atoms; X and Y are selected from the radicals (--CH 2 --) 2 and --(--CH 2 --) 3; and n is an integer having a value of at least 2; the acid moieties being present in an amount of from 2 to about 12 units and the alcohiol moieties numbering from 1 to about 11, with the proviso that said oxazolidine-terminated polyesters provide a useable viscosity for coatings in the formulations in which they are used.
Claim 10
Dependent Claim
25 words
The compositions of claim 7 in which the polyester is of a diol and a dicarboxylic acid, and n is no more than about 8.
Claim 11
Dependent Claim
13 words
The composition of claim 9 in which the acid and diol are aliphatic.
Claim 12
Dependent Claim
16 words
The composition of claim 8 in which the acid is aromatic and the diol is aliphatic.
Claim 13
Dependent Claim
26 words
The composition of claim 8 in which the acid moiety is adipic, terephthalic, isophthalic, phthalic or azelic and the diol is 1,4-butanediol, dipropylene glycol, neopentyl glycol,
Claim 14
Dependent Claim
25 words
A process of coating or impregnating a substrate comprising the steps of applying the composition of claim 1 thereto, and exposing the composition to moisture.
Claim 15
Dependent Claim
25 words
A process of coating or impregnating a substrate comprising the steps of applying the composition of claim 2 thereto, and exposing the composition to moisture.
Claim 16
Dependent Claim
25 words
A process of coating or impregnating a substrate comprising the steps of applying the composition of claim 3 thereto, and exposing the composition to moisture.
Claim 17
Dependent Claim
25 words
A process of coating or impregnating a substrate comprising the steps of applying the composition of claim 4 thereto, and exposing the composition to moisture.
Claim 18
Dependent Claim
25 words
A process of coating or impregnating a substrate comprising the steps of applying the composition of claim 5 thereto, and exposing the composition to moisture.
Claim 19
Dependent Claim
25 words
A proces of coating or impregnating a substrate comprising the steps of applying the composition of claim 6 thereto, and exposing the composition to moisture.
Claim 20
Dependent Claim
9 words
An article made by the process of claim 12.
Claim 21
Dependent Claim
9 words
An article made by the process of claim 13.
Claim 22
Dependent Claim
8 words
A compound of the statistical average formula: ##STR34##
Claim 23
Dependent Claim
8 words
A compound of the statistical average formula: ##STR34##
Claim 24
Dependent Claim
8 words
A compound of the statistical average formula: ##STR35##
Claim 25
Dependent Claim
8 words
A compound of the statistical average formula: ##STR35##
Claim 26
Dependent Claim
8 words
A compound of the statistical average formula: ##STR36##
Claim 27
Dependent Claim
8 words
A compound of the statistical average formula: ##STR36##
Claim 28
Dependent Claim
8 words
A compound of the statistical average formula: ##STR37##
Claim 29
Dependent Claim
8 words
A compound of the statistical average formula: ##STR37##
Claim 30
Dependent Claim
14 words
A compound of the statistical average formula: ##STR38## wherein m is 1 to 4.
Claim 31
Dependent Claim
14 words
A compound of the statistical average formula: ##STR38## wherein m is 1 to 4.
Claim 32
Dependent Claim
8 words
A compound of the statistical average formula: ##STR39##
Claim 33
Dependent Claim
8 words
A compound of the statistical average formula: ##STR39##
Claim 34
Dependent Claim
8 words
A compound of the statistical average formula: ##STR40##
Claim 35
Dependent Claim
8 words
A compound of the statistical average formula: ##STR40##
Claim 36
Dependent Claim
8 words
A compound of the statistical average formula: ##STR41##
Claim 37
Dependent Claim
8 words
A compound of the statistical average formula: ##STR41##
Claim 38
Dependent Claim
81 words
Compounds having the formulae: ##STR42## in which R 3 is a covalent bond, a C 1 -C 10 alkyl or cycloalkyl, or phenyl; and R 4 is a C 1 -C 10 alkyl or cycloalkyl, or the residue of a poly(C 2 -C 3 )glycol having 2-15 carbon atoms; and the statistical average value of m is from 1 to 4, said compounds having an approximate Mw of from 600 to 5000 and an approximate Mn of from 400 to 3000.
Claim 39
Dependent Claim
81 words
Compounds having the formulae: ##STR42## in which R 3 is a covalent bond, a C 1 -C 10 alkyl or cycloalkyl, or phenyl; and R 4 is a C 1 -C 10 alkyl or cycloalkyl, or the residue of a poly(C 2 -C 3 )glycol having 2-15 carbon atoms; and the statistical average value of m is from 1 to 4, said compounds having an approximate Mw of from 600 to 5000 and an approximate Mn of from 400 to 3000.
Claim 40
Independent Claim
72 words
A method of preparing a polyester terminated with a plurality of oxazolidine groups comprising the steps of dissolving a polyol, a polycarboxylic acid ester in which the carboxyl groups are esterified by a C 1 -C 4 alkanol, and a hydroxy oxazolidine in an organic solvent, along with a transesterification catalyst, and heating the mixture to a temperature at which the materials react, and removing the resulting C 1 -C 4 alkanol.
Claim 41
Independent Claim
72 words
A method of preparing a polyester terminated with a plurality of oxazolidine groups comprising the steps of dissolving a polyol, a polycarboxylic acid ester in which the carboxyl groups are esterified by a C 1 -C 4 alkanol, and a hydroxy oxazolidine in an organic solvent, along with a transesterification catalyst, and heating the mixture to a temperature at which the materials react, and removing the resulting C 1 -C 4 alkanol.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-02-05 | 1982-08-07 | 1983-02-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-05 | 1986-08-07 | 1987-02-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-05 | 1990-08-07 | 1991-02-06 | $7700.00 | Window Closed / Lapsed |