# US 4,397,966 A · Alkylene oxide adducts of vicinal toluenediamine > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,397,966 A - Document ID: US4397966A - Status: Granted - Kind: A - Application number: 06/326,299 - Filed: 1981-12-01 - Granted: 1983-08-09 - Earliest claimed: 1981-12-01 - Assignees: BASF Wyandotte Corporation - Inventors: Theodore O. Stolz; Richard A. Moore; James P. Lutz - Web page: https://patentgrep.com/patent/US4397966A ## CPC - C08G 18/5033: {containing carbocyclic groups (C08G18/5024 takes precedence)} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract The subject invention relates to polyol compositions which are alkylene oxide adducts of a mixture of initiators comprising vicinal toluenediamine and an initiator selected from the group consisting of ammonia, an aliphatic amine having a molecular weight of from 20 to 120, an alkanolamine having a molecular weight of from 50 to 120, and mixtures thereof. Low molecular weight diols may also be used as a co-initiator in combination with ammonia, an aliphatic amine, an alkanolamine, or mixtures thereof. The subject polyol compositions are particularly useful in the preparation of rigid polyurethane foams. ## Claims ### Claim 1 A polyol composition comprising the reaction product of an alkylene oxide and a mixture of initiators comprising vicinal toluenediamine and an initiator selected from the group consisting of ammonia, an aliphatic amine having a molecular weight of from 20 to 120, an alkanolamine having a molecular weight of from 50 to 120, and mixtures thereof. ### Claim 2 (depends on 1) The polyol composition of claim 1 wherein sufficient alkylene oxide is used to produce a polyol having a hydroxyl number of 300 to 600. ### Claim 3 (depends on 2) The polyol composition of claim 2 wherein the vicinal toluenediamine is a mixture consisting essentially of 90 percent by weight of an approximately 1:1 weight ratio of 2,3-toluenediamine and 3,4-toluenediamine and 10 percent by weight of a mixture of 2,4-toluenediamine and 2,6-toluenediamine. ### Claim 4 (depends on 3) The polyol composition of claim 3 wherein the alkylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, and mixtures thereof. ### Claim 5 (depends on 4) The polyol composition of claim 4 wherein the aliphatic amine is ethylenediamine. ### Claim 6 (depends on 4) The polyol composition of claim 4 wherein the alkanolamine is selected from the group consisting of monoethanolamine, diethanolamine, and triethanolamine. ### Claim 7 (depends on 5) The polyol composition of claim 5 wherein the weight ratio of vicinal toluenediamine to ethylenediamine is from 5:1 to 50:1. ### Claim 8 (depends on 7) The polyol composition of claim 7 wherein the alkylene oxide is added in two steps such that from 1-5 moles of ethylene oxide are added in the first step per mole of initiator and from 1-5 moles of propylene oxide are added in the second step, with the proviso that the total amount of alkylene oxide added is such that the polyol composition will have a hydroxyl number of 400 to 550. ### Claim 9 (depends on 7) The polyol composition of claim 7 wherein a diol is used as an initiator in addition to vicinal toluenediamine and aliphatic amine. ### Claim 10 (depends on 9) The polyol composition of claim 9 wherein the diol is propylene glycol. ### Claim 11 (depends on 10) The polyol composition of claim 10 wherein the weight ratio of propylene glycol to ethylenediamine is from 3:1 to 1:3. ### Claim 12 (depends on 11) The polyol composition of claim 11 wherein the alkylene oxide is a mixture of ethylene oxide and propylene oxide with the proviso that sufficient alkylene oxide is used to produce a polyol having a hydroxyl number of 350-450. ### Claim 13 (depends on 12) The polyol composition of claim 12 wherein the weight ratio of ethylene oxide to propylene oxide is from 3:1 to 1:3. ### Claim 14 A process for preparing a polyol composition comprising reacting an alkylene oxide and a mixture of initiators comprising vicinal toluenediamine and an initiator selected from the group consisting of ammonia, an aliphatic amine having a molecular weight of from 20 to 120, an alkanolamine having a molecular weight of from 50 to 120, and mixtures thereof. ### Claim 15 (depends on 14) The process of claim 14 wherein sufficient alkylene oxide is used to produce a polyol having a hydroxyl number of 300 to 600. ### Claim 16 (depends on 15) The process of claim 15 wherein the vicinal toluenediamine is a mixture consisting essentially of 90 percent by weight of an approximately 1:1 weight ratio of 2,3-toluenediamine and 3,4-toluenediamine and 10 percent by weight of a mixture of 2,4-toluenediamine and 2,6-toluenediamine. ### Claim 17 (depends on 16) The process of claim 16 wherein the alkylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, and mixtures thereof. ### Claim 18 (depends on 17) The process of claim 17 wherein the aliphatic amine is ethylenediamine. ### Claim 19 (depends on 17) The process of claim 17 wherein the alkanolamine is selected from the group consisting of monoethanolamine, diethanolamine, and triethanolamine. ### Claim 20 (depends on 18) The process of claim 18 wherein the weight ratio of vicinal toluenediamine to ethylenediamine is from 5:1 to 50:1. ### Claim 21 (depends on 20) The process of claim 20 wherein the alkylene oxide is added in two steps such that from 1 to 5 moles of ethylene oxide are added in the first step per mole of initiator and from 1 to 5 moles of propylene oxide are added in the second step, with the proviso that the total amount of alkylene oxide added is such that the polyol composition will have a hydroxyl number of 450 to 550. ### Claim 22 (depends on 20) The polyol composition of claim 20 wherein a diol is used as an initiator in addition to vicinal toluenediamine and aliphatic amine. ### Claim 23 (depends on 22) The polyol composition of claim 22 wherein the diol is propylene glycol. ### Claim 24 (depends on 23) The process of claim 23 wherein the weight ratio of propylene glycol to ethylenediamine is from 3:1 to 1:3. ### Claim 25 (depends on 24) The process of claim 24 wherein the alkylene oxide is a mixture of ethylene oxide and propylene oxide with the proviso that sufficient alkylene oxide is used to produce a polyol having a hydroxyl number of 350 to 450. ### Claim 26 (depends on 25) The process of claim 25 wherein the weight ratio of ethylene oxide is from 3:1 to 1:3. ### Claim 27 (depends on 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12) A polyurethane foam comprising the reaction product of an organic polyisocyanate, the polyol composition of claims 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13, and a blowing agent wherein the ratio of isocyanate groups of the organic polyisocyanate to active hydrogen atoms of the polyol composition is from 1:0.9 to 1:1.15.