Polyurethane urea-containing compositions and optical articles and methods for preparing them

• US 9,568,643 B2
• Filed: 12/10/2013
• Issued: 02/14/2017
• Est. Priority Date: 12/13/2012
• Status: Active Grant

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Bojkova, Nina Vassileva, Graham, Marvin Jerome, Kryger, Matthew John, Menta, Federico
• Primary Examiner(s): SERGENT, RABON A
• Application Number:
  US14/101,903
• Publication Number:
  US 20140171612A1
• Time in Patent Office: 1,162 Days
• US Class Current: 1/1
• CPC Class Codes: B29C 45/0001 characterised by the choice of material
• CPC Class Codes: B29C 45/72 Heating or cooling
• CPC Class Codes: B29D 11/00009 Production of simple or compound lenses
• CPC Class Codes: B29K 2995/0026 Transparent
• CPC Class Codes: B29K 2995/0031 Refractive
• 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 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/3203 Polyhydroxy compounds
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/3212 containing cycloaliphatic groups
• CPC Class Codes: C08G 18/3215 containing aromatic groups or benzoquinone groups
• CPC Class Codes: C08G 18/3271 Hydroxyamines
• CPC Class Codes: C08G 18/3275 containing two hydroxy groups
• CPC Class Codes: C08G 18/34 Carboxylic acids; Esters thereof with monohydroxyl compounds
• CPC Class Codes: C08G 18/3876 containing mercapto groups
• CPC Class Codes: C08G 18/4825 Polyethers containing two hydroxy groups C08G18/4833 - C08G18/5096 take precedence
• CPC Class Codes: C08G 18/6685 with compounds of group C08G18/3225 or polyamines of C08G18/38
• CPC Class Codes: C08G 18/6688 with compounds of group C08G18/3271
• CPC Class Codes: C08G 18/721 Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
• CPC Class Codes: C08G 18/722 Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
• CPC Class Codes: C08G 18/724 : Combination of aromatic polyisocyanates with (cyclo)aliphatic polyisocyanates
• CPC Class Codes: C08G 18/73 : acyclic
• CPC Class Codes: C08G 18/755 : and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/758 : containing two or more cycloaliphatic rings
• CPC Class Codes: C08G 2120/00 : Compositions for reaction injection moulding processes
• CPC Class Codes: C08L 75/02 : Polyureas
• CPC Class Codes: C08L 75/04 : Polyurethanes
• CPC Class Codes: C08L 81/00 : Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
• CPC Class Codes: G02B 1/04 : made of organic materials, e.g. plastics G02B1/08 takes precedence
• CPC Class Codes: G02B 1/041 : Lenses
• CPC Class Codes: G02B 1/08 : made of polarising materials
• CPC Class Codes: G02B 1/14 : Protective coatings, e.g. hard coatings

Abstract

A composition for the preparation of a transparent, non-elastomeric optical article is provided, the composition including:

• • (1) a polyisocyanate component containing one or more different polyisocyanates; and
  • (2) a component that is reactive with isocyanates, including:
  • (a) optionally at least one polyol having a number average molecular weight greater than 500;
  • (b) (i) at least one polyol and/or polythiol and (ii) at least one compound containing both amine and hydroxyl functional groups, wherein the compound (ii) has a number average molecular weight less than 500; and optionally
  • (3) a urethanation catalyst.

Multi-step and one-pot methods of preparing a cured, non-elastomeric polyurethane-containing optical article are also provided.

Claims

1. A method of preparing a transparent, non-elastomeric optical article comprising:

(1) combining to form a reaction mixture;

(a) a polyisocyanate component comprising one or more different polyisocyanates; and

(b) an active hydrogen component comprising;

(b1) a first component that is free of amino groups comprising at least one first polyol; and

(b2) a second component comprising,

at least one second polyol and/or at least one polythiol, and

at least one compound containing both amine and hydroxyl functional groups and has the structure H₂N-L-OH, wherein L is a linear or branched alkyl, aryl, aralkyl, or alkaryl chain optionally containing hetero atoms,

wherein the at least one second polyol has a number average molecular weight of 60 to 450;

(2) introducing the reaction mixture to a mold at a temperature and for a time sufficient to form a thermoset polymerizate; and

(3) releasing the polymerizate from the mold to yield a transparent optical article.

2. The method of claim 1, wherein less than 40 percent by weight of the first polyols, based on total weight of first polyols in the first component (b1), have a number average molecular weight greater than 450.

3. The method of claim 2, wherein less than 35 percent by weight of the first polyols, based on total weight of first polyols in the first component (b1), have a number average molecular weight greater than 450.

4. The method of claim 3, wherein less than 30 percent by weight of the first polyols, based on total weight of first polyols in the first component (b1), have a number average molecular weight greater than 450.

5. The method of claim 1 wherein the polyisocyanate component comprises isophorone diisocyanate, dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, diphenylmethane-4,4′

-diisocyanate, meta-tetramethylxylene diisocyanate (1,3-bis(1-isocyanato-1-methylethyl)-benzene), and/or meta-xylylene diisocyanate.

6. The method of claim 1 wherein the compound containing both amine and hydroxyl functional groups has a number average molecular weight of 60 to 450.

7. The method of claim 1 wherein the compound containing both amine and hydroxyl functional groups has the structure:

8. The method of claim 1 wherein the compound containing both amine and hydroxyl functional groups comprises ethanolamine, amino-2-propanol, 2-amino-1-methyl-1-propanol, 2-amino-1-butanol and/or diethylene glycolamine.

9. The method of claim 1 wherein the reaction mixture is free of polyamines.

10. The method of claim 1 wherein the reaction mixture is free of compounds containing both amino and aromatic functional groups.

11. The method of claim 1 wherein the reaction mixture is free of polyols containing aromatic groups.

12. The method of claim 1 wherein (b2), of the active hydrogen component (b), comprises at least one polythiol.

13. The method of claim 1 wherein the transparent optical article demonstrates a refractive index of at least 1.52.

14. A method of preparing a transparent, non-elastomeric optical article comprising:

(1) combining to form a reaction mixture;

(a) a polyisocyanate component comprising one or more different polyisocyanates; and

(b) at least one first polyol, wherein the polyisocyanate component is present in stoichiometric excess relative to hydroxyl functional groups;

(2) allowing the components to react at a temperature and for a time sufficient to consume all of the hydroxyl functional groups and form an intermediate product comprising a polyurethane prepolymer having isocyanate functional groups in admixture with excess polyisocyanate;

(3) mixing the intermediate product formed in step (2) with

at least one compound containing both amine and hydroxyl functional groups, wherein the compound containing both amine and hydroxyl functional groups has the structure H₂N-L-OH, wherein L is a linear or branched alkyl, aryl, aralkyl, or alkaryl chain optionally containing hetero atoms, and

optionally an active hydrogen component comprising at least one second polyol and/or at least one polythiol,

to form a second reaction mixture;

(4) introducing the second reaction mixture formed in step (3) via injection to a mold at a temperature and for a time sufficient to form a thermoset polymerizate; and

(5) releasing the polymerizate from the mold to yield a transparent optical article.