Patent US4816509A successfully refreshed from Google Patents.
US4816509A
Expired / Lapsed
US
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Water swellable sealant
Assignee: Adeka Corp
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Filing: 1985-06-25
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Granted: 1989-03-28
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Expires: 2005-06-25
Abstract
Abstract PCT No. PCT/JP85/00359 Sec. 371 Date Jan. 29, 1986 Sec. 102(e) Date Jan. 29, 1986 PCT Filed Jun. 25, 1985 PCT Pub. No. WO86/00328 PCT Pub. Date Jan. 16, 1986.Water-swellable moisture-curing one-package polyurethane sealant which includes (1) a water-swellable polyurethane prepolymer having 1.5-10% terminal NCO group content obtained by reacting polyisocyanate with polyoxyalkylenepolyol having 50-90% of oxyethylene units based on polyalkylene chain molecular weight (2) non water-swellable polyurethane prepolymer having terminal NCO groups obtained by reacting polyisocyanate with polyoxyalkylenepolyol having 3-4 carbon atom oxyalkylene units, and (3) a filler. The sealant exhibits has been improved storage stability.
Inventors
- 👤 Takuo Fukushima
- 👤 Yasumasa Hayashida
- 👤 Jinichi Omi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 01:20
CPC Classifications
C; C09; C09K; C09K3/00; C09K3/10; C09K3/1006; C09K3/1021; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/10; C08G18/28; C08G18/40; C08G18/48; C08G18/4833; C08G18/4837; C08G2190/00; C08G2210/00; C09K2003/1034; C09K2003/104; C09K2003/1043; C09K2003/1056; C09K2200/00; C09K2200/02; C09K2200/0239; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31605
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
219 words
A water-swellable moisture-curing one-package polyurethane sealant comprising: (1) 20 to 100 parts by weight of a water-swellable polyurethane prepolymer having 1.5-10% terminal NCO group content which is obtained by a polyisocyanate with one or more polyetherpolyols having the following general formula, R((OR.sub.1).sub.n OH).sub.p (I) wherein R is a polyhydric alcohol radical; (OR 1 ) n is a polyoxyalkylene chain comprising 50-90 weight % of oxyethylene units and 50-10 weight % of oxyalkylene units having 3-4 carbon atoms; n is a number which represents the polymerization degree of said polyoxyalkylene chain, such that n restricts the hydroxy group equivalent of said polyetherpolyol (I) to the range 500-4000; and p is a number selected from 2-8; (2) 100 parts by weight of a non water-swellable polyurethane prepolymer having terminal NCO groups obtained by reacting a polyisocyanate with one or more polyetherpolyols having the following general formula, R.sub.2 ((OR.sub.3).sub.m OH).sub.q (II) wherein R 2 is a polyhydric alcohol radical; (OR 3 ) m is a polyoxyalkylene chain comprising oxyethylene units having 3-4 carbon atoms; m is a number which represents the polymerization degree of said polyoxyalkylene chain, such that m restricts the hydroxy group equivalent of said polyetherpolyol (II) to the range 500-4000; and q is a number selected from 2-8; and (3) 2 to 100 parts by weight of a filler.
Claim 2
Dependent Claim
219 words
A water-swellable moisture-curing one-package polyurethane sealant comprising: (1) 20 to 100 parts by weight of a water-swellable polyurethane prepolymer having 1.5-10% terminal NCO group content which is obtained by a polyisocyanate with one or more polyetherpolyols having the following general formula, R((OR.sub.1).sub.n OH).sub.p (I) wherein R is a polyhydric alcohol radical; (OR 1 ) n is a polyoxyalkylene chain comprising 50-90 weight % of oxyethylene units and 50-10 weight % of oxyalkylene units having 3-4 carbon atoms; n is a number which represents the polymerization degree of said polyoxyalkylene chain, such that n restricts the hydroxy group equivalent of said polyetherpolyol (I) to the range 500-4000; and p is a number selected from 2-8; (2) 100 parts by weight of a non water-swellable polyurethane prepolymer having terminal NCO groups obtained by reacting a polyisocyanate with one or more polyetherpolyols having the following general formula, R.sub.2 ((OR.sub.3).sub.m OH).sub.q (II) wherein R 2 is a polyhydric alcohol radical; (OR 3 ) m is a polyoxyalkylene chain comprising oxyethylene units having 3-4 carbon atoms; m is a number which represents the polymerization degree of said polyoxyalkylene chain, such that m restricts the hydroxy group equivalent of said polyetherpolyol (II) to the range 500-4000; and q is a number selected from 2-8; and (3) 2 to 100 parts by weight of a filler.
Claim 3
Independent Claim
237 words
A method of preparing a water-swellable moisture-curing one-package polyurethane sealant comprising: (a) mixing 2 to 100 parts by weight of a filler and 100 parts by weight of a non water-swellable polyurethane prepolymer having terminal NCO groups obtained by reacting polyisocyanate with one or more polyetherpolyols having the following general formula, R.sub.2 ((OR.sub.3).sub.m OH).sub.8 (II) wherein R 2 is a polyhydric alcohol radical; (OR 3 ) m is a polyoxyalkylene chain comprising oxyethylene units having 3-4 carbon atoms; m is a number which represents the polymerization degree of said polyoxyalkylene chain, such that m restricts the hydroxy group equivalent of said polyetherpolyol (II) to the range 500-4000; and q is a number selected from 2-8, to form a non water-swellable polyurethane composition, (b) adding to said non water-swellable polyurethane composition 20 to 100 parts by weight of a water swellable polyurethane prepolymer having 1.5-10% terminal NCO group content which is obtained by reacting polyisocyanate with one or more polyetherpolyols having the following general formula, R((OR.sub.1).sub.n OH).sub.p (I) wherein R is a polyhydric alcohol radical; (OR 1 ) n is a polyoxyalkylene chain comprising 50-90 weight % of oxyethylene units and 50-10 weight % of oxyalkylene units having 3-4 carbon atoms; n is a number which represents the polymerization degree of said polyoxyalkylene chain, such that n restricts the hydroxy group equivalent of said polyetherpolyol (I) to the range 500-4000; and p is a number selected from 2-8.
Claim 4
Independent Claim
237 words
A method of preparing a water-swellable moisture-curing one-package polyurethane sealant comprising: (a) mixing 2 to 100 parts by weight of a filler and 100 parts by weight of a non water-swellable polyurethane prepolymer having terminal NCO groups obtained by reacting polyisocyanate with one or more polyetherpolyols having the following general formula, R.sub.2 ((OR.sub.3).sub.m OH).sub.8 (II) wherein R 2 is a polyhydric alcohol radical; (OR 3 ) m is a polyoxyalkylene chain comprising oxyethylene units having 3-4 carbon atoms; m is a number which represents the polymerization degree of said polyoxyalkylene chain, such that m restricts the hydroxy group equivalent of said polyetherpolyol (II) to the range 500-4000; and q is a number selected from 2-8, to form a non water-swellable polyurethane composition, (b) adding to said non water-swellable polyurethane composition 20 to 100 parts by weight of a water swellable polyurethane prepolymer having 1.5-10% terminal NCO group content which is obtained by reacting polyisocyanate with one or more polyetherpolyols having the following general formula, R((OR.sub.1).sub.n OH).sub.p (I) wherein R is a polyhydric alcohol radical; (OR 1 ) n is a polyoxyalkylene chain comprising 50-90 weight % of oxyethylene units and 50-10 weight % of oxyalkylene units having 3-4 carbon atoms; n is a number which represents the polymerization degree of said polyoxyalkylene chain, such that n restricts the hydroxy group equivalent of said polyetherpolyol (I) to the range 500-4000; and p is a number selected from 2-8.
Claim 5
Dependent Claim
37 words
The polyurethane sealant according to claim 1, wherein said water-swellable polyurethane prepolymer (1) is an amount of 30 to 70 parts by weight, and said filler is in an amount of 10 to 70 parts by weight.
Claim 6
Dependent Claim
29 words
The polyurethane sealant according to claim 1, wherein R is an aliphatic alcohol selected from the group consisting of dihydric alcohols, trihydric alcohols, tetrahydric alcohols, propylene glycol, and glycerol.
Claim 7
Dependent Claim
17 words
The polyurethane sealant according to claim 1, wherein said oxyalkylene units in component (1) comprise propylene oxide.
Claim 8
Dependent Claim
25 words
The polyurethane sealant according to claim 1, wherein said one or more polyetherpolyols in component (1) have a molecular weight of from 1000 to 10,000.
Claim 9
Dependent Claim
87 words
The polyurethane sealant according to claim 1, wherein said one or more polyetherpolyols in component (1) are difunctional polyetherpolyols represented by the following general formula, R'(COR'.sub.1).sub.n OH).sub.2 (I- 1) wherein R' is a dihydric alcohol radical; (OR' 1 ) n is a polyoxyalkylene chain comprising 50-90 weight % of oxyethylene units and 50-10 weight % of oxpropylene units; and n is a number which represents the polymerization degree of said polyoxyalkylene chain, such that n restricts the hydroxy group equivalent of the polyetherpolyol to the range 500-4000.
Claim 10
Dependent Claim
12 words
The polyurethane sealant according to claim 7, wherein R' is propylene glycol.
Claim 11
Dependent Claim
86 words
The polyurethane sealant according to claim 1, wherein said one or more polyetherpolyols in component (1) are trifunctional polyetherpolyols represented by the following general formula, R"(COR'.sub.1).sub.n OH).sub.3 (I- 2) wherein R" is a trihydric alcohol radical; (OR' 1 ) n is a polyoxyalkylene chain comprising 50-90 weight % of oxyethylene units and 50-10 weight % of oxypropylene units; and n is a number which represents the polymerization degree of said polyoxyalkylene chain, such that n restricts the hydroxy group equivlent of thepolyetherpolyol to the range 500-4000.
Claim 12
Dependent Claim
12 words
The polyurethane sealant according to claim 9, wherein R" is polypropylene glycol.
Claim 13
Dependent Claim
167 words
The polyurethane sealant according to claim 1, wherein said one or more polyetherpolyols comprise a mixture of difunctional polyetherpolyols represented by the following general formula, R'((COR'.sub.1).sub.n OH).sub.2 (I- 1) wherein R' is a dihydric alcohol radical; (OR' 1 ) n is a polyoxyalkylene chain comprising 50-90 weight % of oxyethylene units and 50-10 weight % of oxypropyelene units; and n is a number which represents the polymerization degree of said polyoxyalkylene chain, such that n restricts the hydroxy group equivalent of the polyetherpolyol to the range 500-4000, and trifunctional polyetherpolyols represented by the following general formula, R"(COR'.sub.1).sub.n OH).sub.3 (I- 2) wherein R" is a trihydric alcohol radical; (OR' 1 ) n is a polyoxyalkylene chain comprising 50-90 weight % of oxyethylene units and 50-10 weight % of oxypropylene units; and n is a number which represents the polymerization degree of said polyoxyalkylene chain, such that n restricts the hydroxy group equivalent of the polyetherpolyol to the range 500-4000, in a weight ratio of from 9:1 to 7:3.
Claim 14
Dependent Claim
232 words
The polyurethane sealant according to claim 1, wherein said polyisocyanate is selected from the group consisting of: isocyanates represented by the general formula, ##STR6## wherein B is a benzene or naphthalene ring, --NCO is a ring substituted isocyanate group, Z is a ring substituted halogen atom or alkyl or alkyoxy group having 3 or less carbon atoms, and n is the number 0, 1, or 2; isocyanates represented by the general formula, ##STR7## wherein B is a benzene or naphthalene ring, --(CH 2 ) m NCO is a ring substituted alkyleneisocyanate group, Z is a ring substituted halogen atom or alkyl or alkoxy group having 3 or less carbon atoms, and n is the number 0, 1, or 2; isocyanates represented by the general formula, ##STR8## wherein A is --CH 2 -- or an alkylene group having 3 or more carbon atoms, B is a benzene or a naphthalene ring, --(CH 2 ) n NCO is a ring substituted alkyleneisocyanate group, Z is a ring substituted halogen atom or alkyl or alkoxy group having 3 or less carbon atoms, and n is the number 0, 1, or 2; isocyanates represented by the general formula, ##STR9## wherein Z is a ring substituted halogen atom or alkyl or alkoxy group having 3 or less carbon atoms and m is the number 0, 1, or 2; diphenylsulfone-4,4'-diisocyanate; propane-1,2-diisocyanate; 2,3-dimethylbutane-2,3-diisocyanate; 2-methylpentane-2,4-diisocyanate; octane-3,6-diisocyanate; 3,3-dinitropentane-1,5-diisocyanate; octane-1,6-diisocyanate; and hexamethylenediisocyanate.
Claim 15
Dependent Claim
233 words
The polyurethane sealant according to claim 1, wherein said polyisocyanate is selected from the group consisting of: isocyanates represented by the general formula, ##STR10## wherein B is a benzene or naphthalene ring, --NCO is a ring substituted isocyanate group, Z is a ring substituted halogen atom or alkyl or alkyoxy group having 3 or less carbon atoms, and n is the number 0, 1, or 2; isocyanates represented by the general formula, ##STR11## wherein B is a benzene or naphthalene ring, --(CH 2 ) m NCO is a ring substituted alkyleneisocyanate group, Z is a ring substituted halogen atom or alkyl or alkoxy group having 3 or less carbon atoms, and n is the number 0, 1, or 2; isocyanates represented by the general formula, ##STR12## wherein A is a --CH 2 -- or an alkylene group having 3 or more carbon atoms, B is a benzene or a naphthalene ring, --(CH 2 ) n NCO is a ring substituted alkyleneisocyanate group, Z is a ring substituted halogen atom or alkyl or alkoxy group having 3 or less carbon atoms, and n is the number 0, 1, or 2; isocyanates represented by the general formula, ##STR13## wherein Z is a ring substituted halogen atom or alkyl or alkoxy group having 3 or less carbon atoms and m is the number 0, 1, or 2; diphenylsulfone-4,4'-diisocyanate; propane-1,2-diisocyanate; 2,3-dimethylbutane-2,3-diisocyanate; 2-methylpentane-2,4-diisocyanate; octane-3,6-diisocyanate; 3,3-dinitropentane-1,5-diisocyanate; octane-1,6-diisocyanate; and hexamethylenediisocyanate.
Claim 16
Dependent Claim
30 words
The polyurethane sealant according to claim 1, wherein R 2 is a aliphatic alcohol selected from the group consisting of dihydric alcohols, trihydric alcohols, tetrahydric alcohols, propylene glycol, and glycerol.
Claim 17
Dependent Claim
17 words
The polyurethane sealant according to claim 1, wherein said oxyalkylene units in component (2) comprise polypropylene oxide.
Claim 18
Dependent Claim
24 words
The polyurethane sealant according to claim 1, wherein said one or more polyetherpolyols in componeent (2) have a molecular weight of 1000 to 9000.
Claim 19
Dependent Claim
45 words
The polyurethane sealant according to claim 1, wherein said one or more polyetherpolyols in component (2) comprise a mixture of di- and tri-functional polyetherpolyols obtained from propylene glycol and glycerol, the di- and tri-functional polyetherpolyols being in a weight ratio of from 9:1 to 1:9.
Claim 20
Dependent Claim
16 words
The polyurethane sealant according to claim 17, wherein said polyisocyanate in component (2) is 4,4'-diphenylmethane diisocyanate.
Claim 21
Dependent Claim
35 words
The polyurethane sealant according to claim 1, wherein said filler is a material selected from the group consisting of calcium carbonate, pearlite, silicon oxide, talc, vermiculite, wollastonite, glass, carbon black, titanium oxide, and mixtures thereof.
Claim 22
Dependent Claim
19 words
The polyurethane sealant according to claim 19, wherein said filler comprises a mixture of calcium carbonate and titanium oxide.
Claim 23
Dependent Claim
22 words
The polyurethane sealant according to claim 1, further comprising a material selected from the group consisting of placticizers, thixotropic agents, and asphalt.
Claim 24
Dependent Claim
24 words
The polyurethane sealant according to claim 13, wherein said terminal NCO group content of said water-swellable polyurethane prepolymer is in an amount of 1.5-5%.
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) | 1992-03-27 | 1992-09-26 | 1993-03-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-03-27 | 1996-09-26 | 1997-03-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-03-27 | 2000-09-26 | 2001-03-28 | $7700.00 | Window Closed / Lapsed |