US4031049A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyurethane cross-linking agents
Assignee: Furane Plastics Inc
•
Filing: 1974-04-22
•
Granted: 1977-06-21
•
Expires: 1994-04-22
Abstract
Abstract Polyurethane elastomers, low density high resiliency polyurethane foams and compositions and processes for preparing urethane foams and elastomers comprising reacting a mixture of a polyalkylene polyol having reactive hydrogen atoms as determined by the Zerewitinoff method exhibiting a molecular weight of at least 500, at least one organic polyisocyanate, and as a cross-linking agent at least one sulfur-containing polyamine compound exhibitng the formula: ##STR1## wherein R is a hydrocarbon, and R' is selected from the group consisting of hydrogen, halogens, and hydrocarbons.
Inventors
- 👤 Frank N. Hirosawa
- 👤 Ming H. Lee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:33
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/65; C08G18/66; C08G18/6666; C08G18/667; C08G18/6681; C08G18/6685; C08G18/08; C08G18/10; C08G18/16; C08G18/161; C08G18/163; C08G18/30; C08G18/38; C08G18/3855; C08G18/3863; C08G18/3865; C08G18/3868; Y; Y10; Y10S; Y10S528/00; Y10S528/906
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
99 words
The process of making a highly resilient cellular polyurethane which comprises reacting a polyalkylene polyol having reactive hydrogen atoms as determined by the Zerewitinoff method, an organic poly-functional isocyanate, water, and a gel catalyst, said reduction being carried out in the presence of a blowing catalyst and a cross-linking agent comprising at least one compound selected from those of the formula: ##STR10## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and R' is selected from the group consisting of hydrogen, a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 2
Dependent Claim
99 words
The process of making a highly resilient cellular polyurethane which comprises reacting a polyalkylene polyol having reactive hydrogen atoms as determined by the Zerewitinoff method, an organic poly-functional isocyanate, water, and a gel catalyst, said reduction being carried out in the presence of a blowing catalyst and a cross-linking agent comprising at least one compound selected from those of the formula: ##STR10## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and R' is selected from the group consisting of hydrogen, a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 3
Dependent Claim
17 words
The process of making a cellular polyurethane as claimed in claim 1 wherein said R' is hydrogen.
Claim 4
Dependent Claim
17 words
The process of making a cellular polyurethane as claimed in claim 2 wherein said R is alkyl.
Claim 5
Dependent Claim
20 words
The process of making a cellular polyurethane as claimed in claim 1 wherein at least one cross-linking agent is bis(o-aminophenylthio)methane.
Claim 6
Dependent Claim
20 words
The process of making a cellular polyurethane as claimed in claim 1 wherein at least one cross-linking agent is bis(o-aminophenylthio)ethane.
Claim 7
Dependent Claim
21 words
The process of making a cellular polyurethane as claimed in claim 1 wherein at least one cross-linking agent is bis(o-aminophenylthio)-1,2 propane.
Claim 8
Dependent Claim
24 words
The process of making a highly resilient cellular polyurethane as claimed in claim 1 wherein said blowing catalyst is at least one tertiary amine:
Claim 9
Dependent Claim
19 words
The process of making a cellular polyurethane as claimed in claim 7 wherein said tertiary amine is N-ethyl morpholine.
Claim 10
Dependent Claim
75 words
The process of making a highly resilient cellular polyurethane as claimed in claim 1 wherein the gel catalyst is a compound selected from the group consisting of Sn(OCOR).sub. 2 and R' a SnX b wherein R and R' are hydrocarbon radicals and X is selected from the group consisting of chloride and negative residual portions of organic carboxylic acids, mercaptides, alcohols, and esters of mercaptoacids, a and b being 1-3, a plus b being 4.
Claim 11
Dependent Claim
27 words
The process of claim 1 wherein said cross-linking agent is present in an amount of 0.0001-5 parts by weight per 100 parts by weight of the polyol.
Claim 12
Dependent Claim
131 words
The process of making a highly resilient cellular polyurethane which comprises reacting 100 parts by weight of a substance having active hydrogen atoms as determined by the Zerewitinoff method, 5-300 parts by weight of an organic poly-functional isocyanate, 0.5-10 parts by weight of water, 0.005-4.2 parts by weight of gel catalyst, as a blowing catalyst 0.005 to 4.95 parts by weight of at least one tertiary amine and as a cross-linking agent 0.005 to 10 parts by weight per 100 parts by weight of polyol of at least one compound exhibiting the formula: ##STR11## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and R' is selected from the group consisting of hydrogen, a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 13
Dependent Claim
131 words
The process of making a highly resilient cellular polyurethane which comprises reacting 100 parts by weight of a substance having active hydrogen atoms as determined by the Zerewitinoff method, 5-300 parts by weight of an organic poly-functional isocyanate, 0.5-10 parts by weight of water, 0.005-4.2 parts by weight of gel catalyst, as a blowing catalyst 0.005 to 4.95 parts by weight of at least one tertiary amine and as a cross-linking agent 0.005 to 10 parts by weight per 100 parts by weight of polyol of at least one compound exhibiting the formula: ##STR11## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and R' is selected from the group consisting of hydrogen, a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 14
Dependent Claim
87 words
The process of making a highly resilient cellular polyurethane which comprises reacting 100 parts by weight of a substance having active hydrogen atoms as determined by the Zerewitinoff method, 5-300 parts by weight of an organic poly-functional isocyanate, 0.5-10 parts by weight of water, 0.005-4.2 parts by weight of gel catalyst, 0.005 to 4.95 parts by weight of a blowing catalyst and as a cross-linking agent 0.005 to 10 parts by weight of a compound of the formula: ##STR12## wherein R is alkyl and R' is hydrogen.
Claim 15
Dependent Claim
87 words
The process of making a highly resilient cellular polyurethane which comprises reacting 100 parts by weight of a substance having active hydrogen atoms as determined by the Zerewitinoff method, 5-300 parts by weight of an organic poly-functional isocyanate, 0.5-10 parts by weight of water, 0.005-4.2 parts by weight of gel catalyst, 0.005 to 4.95 parts by weight of a blowing catalyst and as a cross-linking agent 0.005 to 10 parts by weight of a compound of the formula: ##STR12## wherein R is alkyl and R' is hydrogen.
Claim 16
Dependent Claim
114 words
A novel composition suitable for use as a cross-linking agent in the production of highly resilient cold cure polyurethane foams formed by the reaction of an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method, water, and an organic polyisocyanate comprising at least one compound of the formula: ##STR13## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and R' is selected from the group consisting of hydrogen, a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and as a blowing catalyst at least one tertiary amine selected from the group consisting of N-alkyl morpholines and cyclic triethylene diamines and mixtures thereof.
Claim 17
Dependent Claim
114 words
A novel composition suitable for use as a cross-linking agent in the production of highly resilient cold cure polyurethane foams formed by the reaction of an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method, water, and an organic polyisocyanate comprising at least one compound of the formula: ##STR13## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and R' is selected from the group consisting of hydrogen, a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and as a blowing catalyst at least one tertiary amine selected from the group consisting of N-alkyl morpholines and cyclic triethylene diamines and mixtures thereof.
Claim 18
Dependent Claim
14 words
The composition of claim 13 wherein at least one tertiary amine is N-ethyl morpholine.
Claim 19
Dependent Claim
15 words
The composition of claim 13 wherein at least one tertiary amine is cyclic triethylene diamine.
Claim 20
Dependent Claim
9 words
The composition of claim 13 wherein R' is hydrogen.
Claim 21
Dependent Claim
9 words
The composition of claim 16 wherein R is alkyl.
Claim 22
Dependent Claim
115 words
A novel composition for use as a catalyst in the production of cellular polyurethane which comprises 0.005 to 10 parts of at least one compound of the formula: ##STR14## wherein R and R' are hydrocarbons selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, alkaryl, and aralkyl hydrocarbon and as an auxiliary catalyst 0.005 to 10 parts of a compound selected from the group consisting of Sn(OCOR) 2 and R' a SnX b wherein R and R' are hydrocarbon radicals and X is selected from the group consisting of chloride and negative residual portions of organic carboxylic acids, mercaptides, alcohols, and esters of mercaptoacids, a and b being 1-3, a plus b being 4.
Claim 23
Dependent Claim
115 words
A novel composition for use as a catalyst in the production of cellular polyurethane which comprises 0.005 to 10 parts of at least one compound of the formula: ##STR14## wherein R and R' are hydrocarbons selected from the group consisting of alkyl, alkenyl, cycloalkyl, aryl, alkaryl, and aralkyl hydrocarbon and as an auxiliary catalyst 0.005 to 10 parts of a compound selected from the group consisting of Sn(OCOR) 2 and R' a SnX b wherein R and R' are hydrocarbon radicals and X is selected from the group consisting of chloride and negative residual portions of organic carboxylic acids, mercaptides, alcohols, and esters of mercaptoacids, a and b being 1-3, a plus b being 4.
Claim 24
Dependent Claim
42 words
A novel catalyst composition suitable for use in the production of polyurethane foams as claimed in claim 18 wherein the catalyst and auxiliary catalyst are present in the ratio of 0.01 to 5 parts of the former per part of the latter.
Claim 25
Dependent Claim
87 words
A novel cellular polyurethane composition which comprises a cellular polyurethane containing as a blowing catalyst and curing agent a mixture of at least one tertiary amine selected from the group consisting of N-alkyl morpholines and cyclic triethylene diamines and mixtures thereof and a nitrogen-containing organic compound of the formula: ##STR15## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and R' is selected from the group consisting of hydrogen, a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 26
Dependent Claim
87 words
A novel cellular polyurethane composition which comprises a cellular polyurethane containing as a blowing catalyst and curing agent a mixture of at least one tertiary amine selected from the group consisting of N-alkyl morpholines and cyclic triethylene diamines and mixtures thereof and a nitrogen-containing organic compound of the formula: ##STR15## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and R' is selected from the group consisting of hydrogen, a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 27
Dependent Claim
17 words
A novel cellular polyurethane composition as claimed in claim 20 wherein the nitrogen-containing organic compound is bis(o-aminophenylthio)methane.
Claim 28
Dependent Claim
17 words
A novel cellular polyurethane composition as claimed in claim 20 wherein the nitrogen-containing organic compound is bis(o-aminophenylthio)ethane.
Claim 29
Dependent Claim
18 words
A novel cellular polyurethane composition as claimed in claim 20 wherein the nitrogen-containing organic compound is bis(o-aminophenylthio)-1,2 propane.
Claim 30
Dependent Claim
81 words
A process of making an elastomeric polyurethane plastic which comprises mixing an organic polyisocyanate with a mixture of an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method having a molecular weight of at least about 500, and 0.005 to 10 parts by weight per 100 parts by weight of polyol of at least one compound of the formula: ##STR16## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 31
Dependent Claim
81 words
A process of making an elastomeric polyurethane plastic which comprises mixing an organic polyisocyanate with a mixture of an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method having a molecular weight of at least about 500, and 0.005 to 10 parts by weight per 100 parts by weight of polyol of at least one compound of the formula: ##STR16## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 32
Dependent Claim
88 words
The process of making an elastomeric polyurethane plastic which comprises mixing an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method having a molecular weight of at least about 500, an organic polyisocyanate thereby forming a prepolymer, and curing said prepolymer by mixing therein 0.005 to 10 parts by weight per 100 parts by weight of polyol of at least one curing agent of the formula: ##STR17## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 33
Dependent Claim
88 words
The process of making an elastomeric polyurethane plastic which comprises mixing an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method having a molecular weight of at least about 500, an organic polyisocyanate thereby forming a prepolymer, and curing said prepolymer by mixing therein 0.005 to 10 parts by weight per 100 parts by weight of polyol of at least one curing agent of the formula: ##STR17## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 34
Dependent Claim
83 words
In the preparation of an elastomeric polyurethane plastic by a process which comprises reacting an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method and an organic polyisocyanate, the improvement which comprises reacting as a curing agent 0.005 to 10 parts by weight per 100 parts by weight of polyol of at least one compound selected from those of the formula: ##STR18## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 35
Dependent Claim
83 words
In the preparation of an elastomeric polyurethane plastic by a process which comprises reacting an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method and an organic polyisocyanate, the improvement which comprises reacting as a curing agent 0.005 to 10 parts by weight per 100 parts by weight of polyol of at least one compound selected from those of the formula: ##STR18## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 36
Dependent Claim
88 words
A novel composition suitable for use as a curing and cross-linking agent in the production of polyurethane foams by the reaction of an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method, water and a poly-functional isocyanate comprising a compound of the formula: ##STR19## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and R' is selected from the group consisting of hydrogen, a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and stannous 2-ethyl hexanoate.
Claim 37
Dependent Claim
88 words
A novel composition suitable for use as a curing and cross-linking agent in the production of polyurethane foams by the reaction of an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method, water and a poly-functional isocyanate comprising a compound of the formula: ##STR19## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and R' is selected from the group consisting of hydrogen, a hydrocarbon and a hydrocarbon bearing a non-reactive substituent, and stannous 2-ethyl hexanoate.
Claim 38
Dependent Claim
75 words
The process of making an elastomeric polyurethane plastic which comprises reacting an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method with an organic polyisocyanate in the presence of 0.005 to 10 parts by weight per 100 parts by weight of polyol of at least one compound selected from those of the formula: ##STR20## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
Claim 39
Dependent Claim
75 words
The process of making an elastomeric polyurethane plastic which comprises reacting an organic compound having reactive hydrogen atoms as determined by the Zerewitinoff method with an organic polyisocyanate in the presence of 0.005 to 10 parts by weight per 100 parts by weight of polyol of at least one compound selected from those of the formula: ##STR20## wherein R is selected from the group consisting of a hydrocarbon and a hydrocarbon bearing a non-reactive substituent.
References Cited (Backward Citations)
US2765341A
Cited
US3188302A
Cited
US3036996A
Cited
US3425999A
Cited
US3736295A
Cited
US3729370A
Cited
US3586649A
Cited
US3691265A
Cited
US3583926A
Cited
US3752790A
Cited
US3670010A
Cited
US3766148A
Cited
US3718619A
Cited
US3718624A
Cited
US3714127A
Cited
US3740377A
Cited
US3775350A
Cited
US3816360A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-06-20 | 1980-12-20 | 1981-06-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-20 | 1984-12-20 | 1985-06-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-20 | 1988-12-20 | 1989-06-21 | $7700.00 | Window Closed / Lapsed |