Blocked polyisocyanate and uses thereof

• US 6,111,048 A
• Filed: 05/27/1998
• Issued: 08/29/2000
• Est. Priority Date: 02/28/1996
• Status: Expired due to Term

• Current Assignee: Asahi Kasei Kogyo Kabushiki Kaisha (Asahi Kasei Corporation)
• Original Assignee: Asahi Kasei Kogyo Kabushiki Kaisha (Asahi Kasei Corporation)
• Inventors: Usui, Taketoshi, Asahina, Yoshiyuki
• Primary Examiner(s): COONEY, JOHN M
• Application Number:
  US09/077,700
• Time in Patent Office: 825 Days
• Field of Search: 528/45, 528/76, 528/85, 524/270, 524/284, 524/414, 524/589, 524/590, 524/710, 524/773, 524/775, 560/25, 560/26, 560/158, 252/182.22
• US Class Current: 528/45
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/42 Polycondensates having carboxylic or carbonic ester groups in the main chain
• CPC Class Codes: C08G 18/58 Epoxy resins C08G18/42, C08G18/48 take precedence; reaction products of epoxy resins with at least equivalent amounts of compounds containing active hydrogen C08G18/6407, with at least equivalent amounts of amines C08G18/6415; polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen C08G18/003
• CPC Class Codes: C08G 18/62 Polymers of compounds having carbon-to-carbon double bonds
• CPC Class Codes: C08G 18/8025 Masked aliphatic or cycloaliphatic polyisocyanates
• CPC Class Codes: C08G 18/8077 Oximes
• CPC Class Codes: C08L 27/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
• CPC Class Codes: C09J 175/04 Polyurethanes

Abstract

Disclosed is a novel blocked polyisocyanate obtained by blocking the terminal isocyanate groups of a non-blocked polyisocyanate with a thermally dissociative blocking agent, wherein the non-blocked polyisocyanate is obtained by reacting at least one diisocyanate selected from the group consisting of an aliphatic diisocyanate and an alicyclic diisocyanate with a polyhydroxy compound having an average number of hydroxyl groups as many as 4.5 to 10, and removing substantially all unreacted diisocyanate monomers. A coating composition comprising the blocked polyisocyanate of the present invention as a curing agent and a polyol as a main agent not only has excellent curability even under low temperature conditions, but is also capable of forming a coating which has excellent impact resistance. The blocked polyisocyanate of the present invention has excellent miscibility with a plasticizer for the blocked polyisocyanate, so that, an adhesive property-imparting composition comprising the blocked polyisocyanate and a plasticizer and/or a solvent can be combined with a plastisol to prepare a plastisol composition having excellent adhesive properties even under low temperature conditions.

Claims

1. A blocked polyisocyanate, which is substantially the same product as obtained by blocking 50 to 100% by mole of the terminal isocyanate groups of a non-blocked polyisocyanate with a thermally dissociative blocking agent, said non-blocked polyisocyanate being obtained by reacting at least one diisocyanate selected from the group consisting of an aliphatic diisocyanate and an alicyclic diisocyanate with a polyhydroxy compound having an average number of hydroxyl groups of from 4.5 to 10, and removing substantially all unreacted diisocyanate monomers,

said non-blocked polyisocyanate having the following characteristics (a) to (d):

(a) a cyclic isocyanate trimer content of 10% or less, in terms of a ratio of the area of a peak ascribed to a cyclic isocyanate trimer, relative to the total area of all peaks ascribed to said non-blocked polyisocyanate in a gel permeation chromatogram thereof;

(b) an average number of terminal isocyanate groups of from 5 to 20;

(c) a number average molecular weight of from 1,200 to 10,000 as measured by gel permeation chromatography (GPC); and

(d) a terminal isocyanate group content of from 5 to 20% by weight,

said blocked polyisocyanate having the following characteristics (e) to (g);

(e) an average number of blocked terminal isocyanate groups of from 5 to 20;

(f) a blocked terminal isocyanate group content of from 2 to 20% by weight; and

(g) a number average molecular weight of from 1,500 to 15,000 as measured by GPC.

2. The blocked polyisocyanate according to claim 1, wherein said polyhydroxy compound is selected from the group consisting of a polyether polyol, a polyester polyol and a mixture thereof.

3. The blocked polyisocyanate according to claim 2, wherein said polyhydroxy compound is a polyether polyol to which at least one organic oxide selected from the group consisting of alkylene oxides and phenylalkylene oxides is addition-bonded.

4. The blocked polyisocyanate according to claim 3, wherein said alkylene oxide is selected from ethylene oxide, propylene oxide, butylene oxide and cyclohexene oxide, and said phenylalkylene oxide is selected from styrene oxide and phenylpropylene oxide.

5. The blocked polyisocyanate according to claim 4, wherein said polyhydroxy compound is a polyether polyol to which propylene oxide is addition-bonded.

6. The blocked polyisocyanate according to claim 1, which has an allophanate bond in a molecule thereof.

7. The blocked polyisocyanate according to claim 1, wherein said thermally dissociative blocking agent is selected from the group consisting of an alkylphenol compound, an oxime compound, an acid amide compound, an active methylene compound and a mixture thereof.

8. A coating composition comprising:

(A) a polyol having a hydroxyl value of from 10 to 500 mg KOH/g, an acid value of from 0 to 200 mg KOH/g, and a number average molecular weight of from 300 to 60,000; and

(B) a blocked polyisocyanate of any one of claims 1 to 7.

9. The coating composition according to claim 8, wherein said polyol is selected from the group consisting of an aliphatic hydrocarbon polyol, a polyether polyol, a polyester polyol, an epoxy polyol, a fluoropolyol, an acrylic polyol and a mixture thereof.

10. An adhesive property-imparting composition comprising a blocked polyisocyanate of any one of claims 1 to 7 and at least one member selected from the group consisting of a plasticizer for said blocked polyisocyanate and a solvent for said blocked polyisocyanate.

11. A plastisol composition comprising a plastisol and an adhesive property-imparting composition of claim 10.