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US4044171A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for polyaddition products which contain uretdione groups and use in coatings

Assignee: Bayer AG
•
Filing: 1975-04-17
•
Granted: 1977-08-23
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Expires: 1995-04-17
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Abstract

Abstract The present invention teaches a novel polyisocyanate lacquer binder and a method preparing it. The binder is prepared by reacing uretidione containing polyisocyanates optionally mixed with uretdione free diisocyanates with water or with low molecular weight compounds which have two alcoholic hyroxyl groups per molecule. Optionally these compounds may be mixed with up to 60 wt.% based on the total weight of hydroxyl bearing compounds, of low molecular weight compounds with one active alcoholic hydroxyl group per molecule. The proportion of reactants is so selected that the binder produces has from 5 to 20 wt.% of latent isocyanate groups in the form of unopened uretdione rings. The binder can then be mixed with polyhydroxyl compounds having molecular weights of 400 to 10,000 and conventional lacquer pigments and fillers. This mixture can then be coated on a substrate and the coating heated to above 110° C to effect hardening.

Inventors

  • 👤 Hanns Peter Muller
  • 👤 Kuno Wagner
  • 👤 Richard Muller

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 11:54
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/2805; C08G18/70; C08G18/72; C08G18/77; C08G18/78; C08G18/79; C08G18/798; C08G2150/00; C08G2150/20; C08G2250/00

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 198 words
Process for the preparation of pulverulent polyaddition products which contain uretdione groups and which are suitable for use as cross-linkage agents for powder lacquer binders or powder lacquer binder components which contain active hydrogen atoms, by reacting polyisocyanates which contain a uretdione group or mixtures of such polyisocyanates and diisocyanates which are free from uretdione groups with water or with compounds which contain alcoholic hydroxyl groups capable of reacting with isocyanate groups, characterized in that: a. the reactants are reacted together at an NCO/OH ratio of between 1:1 and 1:1.6; b. the compounds containing hydrogen atoms which are reactive with isocyanate groups are water or aliphatic, cycloaliphatic or araliphatic compounds with molecular weights of from 62 to 300 which contain a total of two hydroxyl groups, mixed with from 0 to 60% by weight, based on the total quantity of compounds with active hydrogen atoms, of aliphatic, cycloaliphatic or araliphatic compounds with molecular weight of from 32 to 300 which contain one hydroxyl group; and c. the reactants are used in such proportions that the products of the process contain from 5 to 20% by weight of latent NCO groups and from 0 to 2 hydroxyl end groups.
Claim 2
Dependent Claim 198 words
Process for the preparation of pulverulent polyaddition products which contain uretdione groups and which are suitable for use as cross-linkage agents for powder lacquer binders or powder lacquer binder components which contain active hydrogen atoms, by reacting polyisocyanates which contain a uretdione group or mixtures of such polyisocyanates and diisocyanates which are free from uretdione groups with water or with compounds which contain alcoholic hydroxyl groups capable of reacting with isocyanate groups, characterized in that: a. the reactants are reacted together at an NCO/OH ratio of between 1:1 and 1:1.6; b. the compounds containing hydrogen atoms which are reactive with isocyanate groups are water or aliphatic, cycloaliphatic or araliphatic compounds with molecular weights of from 62 to 300 which contain a total of two hydroxyl groups, mixed with from 0 to 60% by weight, based on the total quantity of compounds with active hydrogen atoms, of aliphatic, cycloaliphatic or araliphatic compounds with molecular weight of from 32 to 300 which contain one hydroxyl group; and c. the reactants are used in such proportions that the products of the process contain from 5 to 20% by weight of latent NCO groups and from 0 to 2 hydroxyl end groups.
Claim 3
Dependent Claim 98 words
Process according to claim 1, characterized in that the compounds with active hydrogen atoms used correspond to the formula: R(OH).sub.n wherein n = 1 or 2 and if n = 1, R denotes an aliphatic hydrocarbon group with from 1 to 18 carbon atoms optionally interrupted by ether oxygen atoms or a cycloaliphatic hydrocarbon group with from 5 to 7 carbon atoms and, if n = 2, R denotes an aliphatic hydrocarbon group with from 2 to 18 carbon atoms optionally interrupted by ether oxygen atoms or a cycloaliphatic hydrocarbon group with from 5 to 15 carbon atoms.
Claim 4
Dependent Claim 10 words
Polyaddition products with uretdione groups obtainable according to claim 1.
Claim 5
Dependent Claim 33 words
The process of claim 1 wherein 0 to 10 wt.% of the monofunctional active hydrogen compounds are used and the reaction is carried out at a temperature of about 0° to 150° C.
Claim 6
Dependent Claim 20 words
The process of claim 4 wherein the reaction is carried out at a temperature of about 80° to 120° C.
Claim 7
Dependent Claim 30 words
The product obtainable by the process of claim 1 having a melting point in the range of about 30° to 240° C and a molecular weight of 800 to 5000.
Claim 8
Dependent Claim 25 words
The product of claim 6 having a melting point in the range of 70° to 180° C and a molecular weight of 900 to 4000.
Claim 9
Dependent Claim 74 words
A process for the coating of substrates which comprises: a. mixing the cross-linking agent of claim 1 with from 5 to 85% by weight based on the total quantity of binder, of polyhydroxyl compounds free from uretdione groups having molecular weights of from 400 to 10,000 and conventional lacquer pigments and fillers, b. coating the mixture on a substrate, and c. heating the coating at temperatures in excess of 110° C until it hardens.
Claim 10
Dependent Claim 19 words
The process of claim 8 wherein the polyhydroxyl compound has a softening point of between 60° and 120° C.
Claim 11
Dependent Claim 19 words
The process of claim 9 wherein the polyhydroxyl compound has a softening point of between 80° and 100° C.
Claim 12
Dependent Claim 37 words
The process of claim 8 wherein the mixture has a softening point of between 50° and 150° C and wherein the mixture begins to crosslink at temperatures at least 10° C in excess of the softening point.
Claim 13
Dependent Claim 132 words
A process for the preparation of pulverizable latent cross-linking agents which comprises 1. dimerizing diisocyanates in the presence of a dimerization catalyst, 2. then inactivating the dimerization catalyst, and 3. reacting said dimerized reaction mixture containing said inactivated catalyst with 4. compounds containing hydrogen atoms reactive with isocyanate groups selected from the groups consisting of water and aliphatic, cycloaliphatic or araliphatic compounds with molecular weights of 62 to 300 which contain one or two hydroxyl groups wherein said compounds are comprised of no more than 60 wt.% of monohydroxy compounds, 5. wherein the reactants are used in such proportions that the NCO/OH ratio is between 1:1 and 1:1.6 and the products of the process contain from 5 to 20 wt.% of latent NCO groups and from 0 to 2 hydroxyl end groups.
Claim 14
Dependent Claim 132 words
A process for the preparation of pulverizable latent cross-linking agents which comprises 1. dimerizing diisocyanates in the presence of a dimerization catalyst, 2. then inactivating the dimerization catalyst, and 3. reacting said dimerized reaction mixture containing said inactivated catalyst with 4. compounds containing hydrogen atoms reactive with isocyanate groups selected from the groups consisting of water and aliphatic, cycloaliphatic or araliphatic compounds with molecular weights of 62 to 300 which contain one or two hydroxyl groups wherein said compounds are comprised of no more than 60 wt.% of monohydroxy compounds, 5. wherein the reactants are used in such proportions that the NCO/OH ratio is between 1:1 and 1:1.6 and the products of the process contain from 5 to 20 wt.% of latent NCO groups and from 0 to 2 hydroxyl end groups.
Claim 15
Dependent Claim 15 words
The process of claim 12 wherein the entire process is conducted in a single vessel.
Claim 16
Dependent Claim 27 words
The process of claim 12 wherein the dimerization catalyst is selected from the group consisting of tertiary phosphines which carry at least one aliphatic substituent and pyridine.
Claim 17
Dependent Claim 16 words
The process of claim 12 wherein the dimerization catalyst is inactivated by the addition of sulphur.
Claim 18
Dependent Claim 37 words
The process of claim 12 wherein the dimerization catalyst is selected from the group consisting of triethylphosphine, tributyl phosphine, phenyldimethylphosphine and pyridine and 0.1 to 5 wt.% of catalyst based on the weight of diisocyanate is used.
Claim 19
Dependent Claim 77 words
A process for the coating of substrates which comprises: a. mixing a cross-linking agent prepared according to claim 12 with from 5 to 85 wt.%, based on the total quantity of a lacquer binder, of polyhydroxyl compounds free from uretdione groups having molecular weights of from 400 to 10,000 and conventional lacquer pigments and fillers, b. coating said mixture on a substrate, and c. heating the coating at temperatures in excess of 110° C until it hardens.
Claim 20
Dependent Claim 35 words
The product obtainable by the process of claim 12 containing inactivated dimerization catalyst and having a melting point in the range of about 30° to 240° C and a molecular weight of 800 to 5000.

References Cited (Backward Citations)

US2978449A Cited
US2993870A Cited
US3793238A Cited
US3893978A Cited
US3926875A Cited
US3853822A Cited
US3923743A Cited
US3947426A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-08-22 1981-02-21 1981-08-23 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-08-22 1985-02-21 1985-08-23 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-08-22 1989-02-21 1989-08-23 $7700.00 Window Closed / Lapsed

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