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US4031049A Expired / Lapsed US ⏱️ 0.0 years remaining

Polyurethane cross-linking agents

Assignee: Furane Plastics Inc
•
Filing: 1974-04-22
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Granted: 1977-06-21
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Expires: 1994-04-22
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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.

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

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