# US 4,391,957 A · Elasticized addition product based on polyalkylene ether-polyols and polyisocyanates, preparation and use thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,391,957 A - Document ID: US4391957A - Status: Granted - Kind: A - Application number: 06/399,791 - Filed: 1982-07-19 - Granted: 1983-07-05 - Earliest claimed: 1981-07-21 - Assignees: Hoechst Aktiengesellschaft - Inventors: Wilhelm Becker - Web page: https://patentgrep.com/patent/US4391957A ## CPC - C08G 59/50: Amines - C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract An elasticized addition product formed from (a) polyalkylene ether-polyols having a molecular weight of 500 to 10,000 and 2 to 6 C atoms in the alkylene radical and (b) polyisocyanates, the ratio of the NCO groups of the component (b) to the OH groups of the component (a) being 1.5:1 to 2.5:1, and the addition product of (a) with (b) is further reacted with hydroxyl compounds from the group comprising (c) imidazolidine of a particular formula and/or (d) hexahydropyrimidine derivatives of a particular formula in an approximately 1:1 ratio of NCO groups to the OH groups of the components (c) and/or (d), and is in the form of this reaction product and/or in the form of a hydrolysis product thereof. Mixtures based on (A) the said addition product as the curing agent and (B) epoxide compounds containing more than one epoxide group, if appropriate together with monoepoxide compounds, are used for the production of molded articles having controlled resilience properties, such as sheet-like structures, adhesive bonds and casting compositions. ## Claims ### Claim 1 An elasticized addition product comprising (a) a polyalkylene ether-polyol and (b) a polyisocyanate wherein (a) has a molecular weight of 500 to 10,000 and 2 to 6 C atoms in the alkylene radical and the ratio of the NCO groups in the component (b) to the OH groups in the component (a) is 1,5:1 to 2,5:1, the addition product thereof is reacted further with a hydroxyl compound selected from the group consisting of (c) an imidazolidine of the formula I ##STR2## wherein R is hydrogen or alkyl having 1 to 4 C atoms, R.sup.1 is (c1) hydrogen, (c2) hydroxyalkyl and alkyl having 1 to 12 C atoms in each case, (c3) --CH.sub.2 --R.sup.5, (c4) --CH.sub.2 --CH.sub.2 --COOR.sup.5, ##STR3## (c6) --CH.sub.2 --CH.sub.2 --CN wherein R.sup.5 represents in each hydroxyalkyl or alkyl having up to 8 C atoms, R.sup.2 denotes (c7) alkyl or alkylene having in each case 1 to 12 C atoms or denotes one of the radicals (c3) to (c6), R.sup.3 and R.sup.4 each denote hydrogen or alkyl having 1 to 5 C atoms or R.sup.3 and R.sup.4 together denote alkylene having 4 to 6 C atoms, and (d) a hexahydropyrimidine derivative of the general formula ##STR4## wherein R.sup.1 to R.sup.5 have the meaning as mentioned under (c), at least one of each of the substituents R.sup.1 to R.sup.5 in the formulae (I) and (II) carrying a hydroxyl group; the ratio of NCO groups to the OH groups of component (c) and (d) or a mixture thereof is approximately 1:1. ### Claim 2 (depends on 1) Addition product as claimed in claim 1 which is partly or completely hydrolyzed. ### Claim 3 A process for the preparation of an elasticized addition product comprising the steps: reacting (a) a polyalkylene ether-polyol having a molecular weight of 500 to 10,000 and 2 to 6 C atoms in the alkylene radical with (b) a polyisocyanate at a temperature of 50.degree. to 100.degree. C. in the presence of a catalyst, the ratio of the NCO groups in the component (b) to the OH groups in the component (a) being 1.5:1 to 2.5:1, followed by further reacting the product of (a) with (b) at ambient or at a temperature up to 150.degree. C. with a hydroxyl compound selected from the group consisting of: (c) an imidazoline of the formula I ##STR5## wherein R is hydrogen or alkyl having 1 to 4 C atoms, R.sup.1 is (c1) hydrogen, (c2) hydroxyalkyl and alkyl having 1 to 12 C atoms in each case, (c3) --CH.sub.2 --R.sup.5, (c4) --CH.sub.2 --CH.sub.2 --COOR.sup.5, ##STR6## (c6) --CH.sub.2 --CH.sub.2 --CN wherein R.sup.5 represents in each case hydroxyalkyl or alkyl having up to 8 C atoms, R.sup.2 denotes (c7) alkyl or alkylene having in each case 1 to 12 C atoms or denotes one of the radicals (c3) to (c6), R.sup.3 and R.sup.4 each denote hydrogen or alkyl having 1 to 5 C atoms or R.sup.3 and R.sup.4 together denote alkylene having 4 to 6 C atoms, and (d) a hexahydropyrimidine derivative of the general formula ##STR7## wherein R.sup.1 to R.sup.5 have the meaning as mentioned under (c), at least one of each of the substituents R.sup.1 to R.sup.5 in the formulae (I) and (II) carrying a hydroxyl group and the ratio of NCO groups to the OH groups of component (c) and (d) or a mixture thereof is approximately 1:1, and isolating the product so produced. ### Claim 4 (depends on 3) A process as claimed in claim 3 wherein the elasticized addition product is subsequently at least partially hydrolyzed. ### Claim 5 (depends on 1) A composition comprising a mixture of (A) at least one elasticized addition product as claimed in claim 1 as a curing agent and (B) an epoxide compound having more than one epoxide group per molecule or combinations thereof with monoepoxide compounds, alone or together with (C) further customary additives. ### Claim 6 (depends on 5) Composition as claimed in claim 5 wherein component (C) is at least in part, a customary amine curing agent, a diluent or a mixture thereof. ### Claim 7 (depends on 5) Composition as claimed in claim 5, wherein the epoxide compound (B) has an epoxide equivalent of 150 to 1,000 and a molecular weight between 300 and 2,000. ### Claim 8 (depends on 5) Composition as claimed in claim 5 for the preparation of molded articles or sheet-like structures by curing. ### Claim 9 (depends on 8) Composition as claimed in claim 8, wherein the curing is effected in the presence of water.