US4101529A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hard, optically clear polyurethane articles
Assignee: PPG Industries Inc
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Filing: 1976-02-04
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Granted: 1978-07-18
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Expires: 1996-02-04
Abstract
Abstract Polyurethane compositions characterized by being heat curable to yield hard, impact-resistant articles having a high heat distortion temperature are disclosed. The cured polyurethane articles are transparent and also hydrolytic and UV light stable as well as being abrasion resistant. The polyurethane is prepared from a cycloaliphatic polyisocyanate, low molecular weight active hydrogen-containing material and optionally a polycarbonate diol. The weight percentage of the urethane moieties and the crosslinked density are carefully controlled so as to provide the proper balance of physical properties, particularly between hardness, flexibility and heat distortion temperature. The polyurethane articles are particularly useful in glazing applications such as aircraft glazing.
Inventors
- 👤 Vernon G. Ammons
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 10:36
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/32; C08G18/3203; C08G18/3206; C08G18/40; C08G18/42; C08G18/44; C08G18/65; C08G18/66; C08G18/6633; C08G18/6637; C08G18/664; C08G18/6644; C08G18/70; C08G18/72; C08G18/74; C08G18/75; C08G18/758
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
169 words
A polyurethane composition substantially free of ether linkages characterized by being heat curable to yield hard, impact-resistant articles having a Shore D hardness at room temperature of at least 75, said articles having a heat distortion temperature as determined according to ASTM D-648 of at least 190° F. (88° C.) and showing no visual change when exposed to ultraviolet light in accordance with ASTM G-25-70, Method A, comprising the reaction product of: (A) a cycloaliphatic polyisocyanate, (B) a low molecular weight active hydrogen-containing material containing only two active hydrogens per molecule, (C) a low molecular weight active hydrogen-containing material having at least three active hydrogens per molecule, and optionally, (D) a polymeric polycarbonate diol; the equivalent ratio of (B)/(C) being within the range of 0.5 to 10/1, said reaction product having a calculated weight percentage of urethane linkages of at least 20 percent, a calculated molecular weight between branch points of 600-4,000 and the percentage by weight of cycloaliphatic structural units being within the range of 45 to 50.
Claim 2
Dependent Claim
169 words
A polyurethane composition substantially free of ether linkages characterized by being heat curable to yield hard, impact-resistant articles having a Shore D hardness at room temperature of at least 75, said articles having a heat distortion temperature as determined according to ASTM D-648 of at least 190° F. (88° C.) and showing no visual change when exposed to ultraviolet light in accordance with ASTM G-25-70, Method A, comprising the reaction product of: (A) a cycloaliphatic polyisocyanate, (B) a low molecular weight active hydrogen-containing material containing only two active hydrogens per molecule, (C) a low molecular weight active hydrogen-containing material having at least three active hydrogens per molecule, and optionally, (D) a polymeric polycarbonate diol; the equivalent ratio of (B)/(C) being within the range of 0.5 to 10/1, said reaction product having a calculated weight percentage of urethane linkages of at least 20 percent, a calculated molecular weight between branch points of 600-4,000 and the percentage by weight of cycloaliphatic structural units being within the range of 45 to 50.
Claim 3
Dependent Claim
34 words
The composition of claim 1 which when cured has a Shore D hardness at room temperature of at least 75; a Gardner impact for a 1/8 inch thick specimen of at least 40 inch/pounds.
Claim 4
Dependent Claim
26 words
The composition of claim 1 which when cured has a tensile strength as determined according to ASTM D-638 of at least 12,000 pounds per square inch.
Claim 5
Dependent Claim
29 words
The composition of claim 3 which when cured retains at least 70 percent of its tensile strength after a 1000 hour exposure to a Weather-O-Meter according to ASTM D-1499-64.
Claim 6
Dependent Claim
36 words
The composition of claim 1 which when cured has less than an 18 percent increase in haze when subjected to 100 cycles on a Taber abrader using a CS-10F abrasion wheel at 500 grams of weight.
Claim 7
Dependent Claim
24 words
The composition of claim 1 in which the equivalent ratio of (B) plus (D) to (C) is within the range of 0.8 to 4.0/1.
Claim 8
Dependent Claim
16 words
The composition of claim 1 in which the cycloaliphatic polyisocyanate is a diisocyanate containing cyclohexyl moiety.
Claim 9
Dependent Claim
12 words
The composition of claim 7 in which the diisocyanate is 4,4'-methylene-bis-(cyclohexyl isocyanate).
Claim 10
Dependent Claim
23 words
The composition of claim 8 in which the 4,4'-methylene-bis-(cyclohexyl isocyanate) is in a stereo:isomer ratio of 55 percent trans and 45 percent cis.
Claim 11
Dependent Claim
20 words
The composition of claim 1 in which (B) is a hydroxyterminated alkylene diol containing from 2 to 10 carbon atoms.
Claim 12
Dependent Claim
22 words
The composition of claim 10 in which the alkylene diol is selected from the class consisting of ethylene glycol, 1,4-butanediol and 1,6-hexanediol.
Claim 13
Dependent Claim
12 words
The composition of claim 1 in which (C) is an aliphatic triol.
Claim 14
Dependent Claim
20 words
The composition of claim 12 in which the aliphatic triol is selected from the class consisting of trimethylolpropane and trimethylolethane.
Claim 15
Dependent Claim
16 words
The composition of claim 1 in which the polycarbonate diol has a molecular weight of 700-2000.
Claim 16
Dependent Claim
26 words
The composition of claim 14 in which the polycarbonate diol is a poly(alkylenecarbonate) diol in which the alkylene groups contain from 5 to 10 carbon atoms.
Claim 17
Dependent Claim
18 words
The composition of claim 15 in which the alkylene moiety of the poly(alkylenecarbonate) diol is a cycloalkylene moiety.
Claim 18
Dependent Claim
12 words
The composition of claim 16 in which the cycloalkylene moiety is cyclohexyl.
Claim 19
Dependent Claim
25 words
The composition of claim 15 in which the alkylene moiety of the poly(alkylenecarbonate) diol is a mixed moiety selected from linear alkylene and cycloalkylene moieties.
Claim 20
Dependent Claim
14 words
The composition of claim 18 in which the cycloalkylene moiety is cyclohexyl dimethyl moiety.
Claim 21
Dependent Claim
17 words
The composition of claim 18 in which the mixed alkylene moieties are hexyl and cyclohexyl dimethyl moieties.
Claim 22
Dependent Claim
167 words
A polyurethane composition substantially free of ether linkages characterized by being heat curable to yield hard, impact-resistant articles having a Shore D hardness at room temperature of at least 75, said articles having a heat distortion temperature according to ASTM D-648 of at least 190° F. (88° C.) and showing no visual change when exposed to ultraviolet light in accordance with ASTM G-25-70, comprising the reaction product of: (A) 4,4'-methylene-bis(cyclohexyl isocyanate), (B) a low molecular weight active hydrogen-containing material selected from the class consisting of ethylene glycol, 1,4-butanediol and 1,6-hexanediol and mixtures thereof, (C) trimethylolpropane; the equivalent ratio of (A) to (B) and (C) being about 1 to 1, the equivalent ratio of (B) to (C) being within the range of 0.5 to 10/1; said reaction product having a calculated weight percentage of urethane linkages of at least 20 percent, a calculated molecular weight between branch points of 600-4000 and the percentage by weight of the cycloaliphatic structural units being within the range of 45 to 50.
Claim 23
Dependent Claim
167 words
A polyurethane composition substantially free of ether linkages characterized by being heat curable to yield hard, impact-resistant articles having a Shore D hardness at room temperature of at least 75, said articles having a heat distortion temperature according to ASTM D-648 of at least 190° F. (88° C.) and showing no visual change when exposed to ultraviolet light in accordance with ASTM G-25-70, comprising the reaction product of: (A) 4,4'-methylene-bis(cyclohexyl isocyanate), (B) a low molecular weight active hydrogen-containing material selected from the class consisting of ethylene glycol, 1,4-butanediol and 1,6-hexanediol and mixtures thereof, (C) trimethylolpropane; the equivalent ratio of (A) to (B) and (C) being about 1 to 1, the equivalent ratio of (B) to (C) being within the range of 0.5 to 10/1; said reaction product having a calculated weight percentage of urethane linkages of at least 20 percent, a calculated molecular weight between branch points of 600-4000 and the percentage by weight of the cycloaliphatic structural units being within the range of 45 to 50.
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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) | 1981-07-17 | 1982-01-16 | 1982-07-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-17 | 1986-01-16 | 1986-07-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-17 | 1990-01-16 | 1990-07-18 | $7700.00 | Window Closed / Lapsed |