US4160853A
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US
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Catalyst for making polycarbonate diols for use in polycarbonate urethanes
Assignee: PPG Industries Inc
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Filing: 1977-11-29
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Granted: 1979-07-10
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Expires: 1997-11-29
Abstract
Abstract Energy-absorbing laminates for use in automobile windshields or other safety glass applications comprising a polycarbonate urethane and a sheet of glass are disclosed. The polyurethane is formed from a cycloaliphatic diisocyanate, a compound containing at least two active hydrogens per molecule and having a molecular weight below 250, and a polycarbonate diol prepared by the reaction of an aliphatic diol and a dialkyl carbonate using a titanium catalyst. CROSS-REFERENCE TO RELATED APPLICATIONS This application is a continuation-in-part of application Ser. No. 681,012 entitled "Catalyst for Making Polycarbonate Diols for Use in Polycarbonate Urethanes" filed Apr. 28, 1976, now abandoned which in turn is a continuation-in-part of application Ser. No. 385,019 entitled "Transparent, Impact-Resistant Poly(alkylenecarbonate Urethane) Laminates" filed Aug. 2, 1973, now abandoned.
Inventors
- 👤 Vernon G. Ammons
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 22:42
CPC Classifications
B; B32; B32B; B32B17/00; B32B17/06; B32B17/10; B32B17/10005; B32B17/1055; B32B17/1077; B32B17/10009; B32B17/10018; B32B17/10807; B32B17/10816; B32B17/10825; B32B17/10834; B32B27/00; B32B27/40; C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/42; C08G18/44; C08G18/65; C08G18/66; C08G18/6633; C08G18/6637; C08G18/70; C08G18/72; C08G18/74; C08G18/75; C09; C09J; C09J175/00; C09J175/04; C09J175/06; B32B2307/00; B32B2307/40; B32B2307/412; B32B2307/70; B32B2307/712; B32B2309/00; B32B2309/08; B32B2309/10; B32B2309/105; B32B2605/00; B32B2605/003; Y; Y10; Y10T; Y10T428/00; Y10T428/24; Y10T428/24942; Y10T428/2495; Y10T428/24967; Y10T428/31504; Y10T428/31507; Y10T428/31551; Y10T428/31598; Y10T428/31601; Y10T428/31616
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
58 words
A polyurethane which is the reaction product of: a. a polycarbonate diol having a molecular weight between 500 and 5000 prepared by the reaction of a hydroxy-terminated aliphatic diol with a dialkyl carbonate in the presence of a titanium catalyst, said catalyst being a titanium compound which is substantially free from alkali metal; and b. an organic diisocyanate.
Claim 2
Dependent Claim
58 words
A polyurethane which is the reaction product of: a. a polycarbonate diol having a molecular weight between 500 and 5000 prepared by the reaction of a hydroxy-terminated aliphatic diol with a dialkyl carbonate in the presence of a titanium catalyst, said catalyst being a titanium compound which is substantially free from alkali metal; and b. an organic diisocyanate.
Claim 3
Dependent Claim
28 words
The polyurethane as described in claim 1, wherein the molecular weight of the polycarbonate diol is below 700 and a and b are present in substantially equimolar ratio.
Claim 4
Dependent Claim
114 words
The polyurethane as described in claim 1, wherein the titanium catalyst is a titanium compound selected from the group consisting of: TiX 4 , wherein X is a halogen; ether complexes of TiX 4 ; (RR' 3 N) 2 [Ti(OR) 6 ], and (RR' 3 N)H[Ti(OR) 6 ], wherein R is an alkyl group having from one to six carbon atoms and R' is R or an aryl group having from six to nine carbon atoms; Ti(OR) 4 , wherein R is an alkyl group having from one to six carbon atoms; and titanium alkyl esters having from one to three ester groups wherein the alkyl group contains from one to six carbon atoms.
Claim 5
Dependent Claim
14 words
The polyurethane as described in claim 3 wherein the titanium catalyst is tetrabutyl titanate.
Claim 6
Dependent Claim
14 words
The polyurethane as described in claim 3 wherein the diisocyanate is a cycloaliphatic diisocyanate.
Claim 7
Dependent Claim
75 words
A polyurethane which is the reaction product of: a. a polycarbonate diol having a molecular weight between 500 and 5000 prepared by the reaction of a hydroxy-terminated aliphatic diol with a dialkyl carbonate in the presence of a titanium catalyst, said catalyst being a titanium compound which is substantially free from alkali metal; b. an organic diisocyanate; and c. an organic compound containing at least two isocyanate-reactive hydrogens and having a molecular weight below 250.
Claim 8
Dependent Claim
75 words
A polyurethane which is the reaction product of: a. a polycarbonate diol having a molecular weight between 500 and 5000 prepared by the reaction of a hydroxy-terminated aliphatic diol with a dialkyl carbonate in the presence of a titanium catalyst, said catalyst being a titanium compound which is substantially free from alkali metal; b. an organic diisocyanate; and c. an organic compound containing at least two isocyanate-reactive hydrogens and having a molecular weight below 250.
Claim 9
Dependent Claim
23 words
The polyurethane as described in claim 6, wherein the organic compound containing at least two isocyanate-reactive hydrogens is a monomeric hydroxy-terminated aliphatic diol.
Claim 10
Dependent Claim
36 words
The polyurethane as described in claim 6, wherein the molecular weight of the polycarbonate diol is greater than about 700 but less than about 5000 and the molar ratio of c:a is about 1.25 to 5.70:1.00.
Claim 11
Dependent Claim
114 words
The polyurethane as described in claim 6, wherein the titanium catalyst is a titanium compound selected from the group consisting of: TiX 4 , wherein X is a halogen; ether complexes of TiX 4 ; (RR' 3 N) 2 [Ti(OR) 6 ], and (RR' 3 N)H[Ti(OR) 6 ], wherein R is an alkyl group having from one to six carbon atoms and R' is R or an aryl group having from six to nine carbon atoms; Ti(OR) 4 , wherein R is an alkyl group having from one to six carbon atoms; and titanium alkyl esters having from one to three ester groups wherein the alkyl group contains from one to six carbon atoms.
Claim 12
Dependent Claim
14 words
The polyurethane as described in claim 9, wherein the titanium catalyst is tetrabutyl titanate.
Claim 13
Dependent Claim
15 words
The polyurethane as described in claim 6, wherein the organic diisocyanate is a cycloaliphatic diisocyanate.
Claim 14
Dependent Claim
15 words
The polyurethane as described in claim 11, wherein the cycloaliphatic diisocyanate is 4,4'-methylene-bis (cyclohexyl isocyanate).
Claim 15
Dependent Claim
35 words
The polyurethane as described in claim 6, wherein the molecular weight of the polycarbonate diol is between about 1000 and about 3000 and the molar ratio of a:b:c is about 1.00:2.40 to 4:60:1.40 to 3.60.
Claim 16
Dependent Claim
32 words
The polyurethane as described in claim 13, wherein the polycarbonate diol is prepared by the reaction of diethyl carbonate and a hydroxy-terminated alkylene diol containing from 4 to about 10 carbon atoms.
Claim 17
Dependent Claim
81 words
A safety glass laminate comprising: a. a ply of glass; and b. laminated to said ply of glass a ply of transparent, energy-absorbing polycarbonate urethane which is the reaction product of (1) a polycarbonate diol having a molecular weight between 500 and 5000 prepared by the reaction of a hydroxy-terminated aliphatic diol and a dialkyl carbonate in the presence of a titanium catalyst said catalyst being a titanium compound which is substantially free from alkali metal; and (2) an organic diisocyanate.
Claim 18
Dependent Claim
81 words
A safety glass laminate comprising: a. a ply of glass; and b. laminated to said ply of glass a ply of transparent, energy-absorbing polycarbonate urethane which is the reaction product of (1) a polycarbonate diol having a molecular weight between 500 and 5000 prepared by the reaction of a hydroxy-terminated aliphatic diol and a dialkyl carbonate in the presence of a titanium catalyst said catalyst being a titanium compound which is substantially free from alkali metal; and (2) an organic diisocyanate.
Claim 19
Dependent Claim
142 words
The laminate as described in claim 15, wherein said polyurethane is the reaction product of a. a polycarbonate diol of molecular weight less than about 700 prepared in the presence of a titanium catalyst selected from the group consisting of: TiX 4 , wherein X is a halogen; ether complexes of TiX 4 ; (RR' 3 N) 2 [Ti(OR) 6 ] and (RR' 3 N)H[Ti(OR) 6 ], wherein R is an alkyl group having from one to six carbon atoms and R' is R or an aryl group having from six to nine carbon atoms; Ti(OR) 4 , wherein R is an alkyl group having from one to six carbon atoms; and titanium alkyl esters having from one to three ester groups wherein the alkyl group contains from one to six carbon atoms; and b. a cycloaliphatic diisocyanate in substantially equimolar ratio.
Claim 20
Dependent Claim
14 words
The laminate as described in claim 16, wherein the titanium catalyst is tetrabutyl titanate.
Claim 21
Dependent Claim
101 words
A safety glass laminate comprising: a. a ply of glass; and b. laminated to said ply of glass, a ply of transparent, energy-absorbing polycarbonate urethane which is the reaction product of: (1) a polycarbonate diol having a molecular weight between 500 and 5000 prepared by the reaction of a hydroxy-terminated aliphatic diol and a dialkyl carbonate in the presence of a titanium catalyst, said catalyst being a titanium compound which is substantially free from alkali metal; (2) an organic diisocyanate; and (3) an organic compound which contains at least two isocyanate-reactive hydrogens and has a molecular weight less than about 250.
Claim 22
Dependent Claim
101 words
A safety glass laminate comprising: a. a ply of glass; and b. laminated to said ply of glass, a ply of transparent, energy-absorbing polycarbonate urethane which is the reaction product of: (1) a polycarbonate diol having a molecular weight between 500 and 5000 prepared by the reaction of a hydroxy-terminated aliphatic diol and a dialkyl carbonate in the presence of a titanium catalyst, said catalyst being a titanium compound which is substantially free from alkali metal; (2) an organic diisocyanate; and (3) an organic compound which contains at least two isocyanate-reactive hydrogens and has a molecular weight less than about 250.
Claim 23
Dependent Claim
178 words
The laminate as described in claim 18, wherein said polyurethane is the reaction product of: a. a polycarbonate diol having a molecular weight between about 1000 and about 3000 prepared by the reaction of diethyl carbonate and a hydroxy-terminated alkylene diol containing from 4 to about 10 carbon atoms in the presence of a titanium catalyst selected from the group consisting of: TiX 4 , wherein X is a halogen; ether complexes of TiX 4 ; (RR' 3 N) 2 [Ti(OR) 6 ], and (RR' 3 N)H[Ti(OR) 6 ], wherein R is an alkyl group having from one to six carbon atoms and R' is R or an aryl group having from six to nine carbon atoms; Ti(OR) 4 , wherein R is an alkyl group having from one to six carbon atoms; and titanium alkyl esters having from one to three ester groups wherein the alkyl group contains from one to six carbon atoms; b. a cycloaliphatic diisocyanate; and c. a monomeric hydroxy-terminated aliphatic diol; the molar ratio of a:b:c being about 1.00:2.40 to 4.60:1.40 to 3.60.
Claim 24
Dependent Claim
39 words
The laminate as described in claim 19, wherein the thickness of said ply of glass is from about 0.065 inch to about 0.250 inch and the thickness of said polyurethane is from abut 0.005 inch to about 0.120 inch.
Claim 25
Dependent Claim
37 words
The laminate as described in claim 20, which comprises a ply of polycarbonate urethane and only one ply of glass, wherein the thickness of said ply of glass is from about 0.125 inch to about 0.235 inch.
Claim 26
Dependent Claim
22 words
The laminate as described in claim 21, wherein the thickness of said polyurethane is from about 0.015 inch to about 0.045 inch.
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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) | 1982-07-09 | 1983-01-08 | 1983-07-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-07-09 | 1987-01-08 | 1987-07-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-07-09 | 1991-01-08 | 1991-07-10 | $7700.00 | Window Closed / Lapsed |