Ultraviolet screening agents and coating materials containing organosilane ester groups

• US 4,051,161 A
• Filed: 05/08/1975
• Issued: 09/27/1977
• Est. Priority Date: 09/15/1972
• Status: Expired due to Term

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Proskow, Stephen
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US05/575,795
• Time in Patent Office: 873 Days
• Field of Search: 260/448.2 B, 260/448.8 R
• US Class Current: 556/436
• CPC Class Codes: C07F 7/0834 Compounds having one or more O-Si linkage for compounds with C-O-Si linkages see C07F7/18
• CPC Class Codes: C08J 7/0427 with only one layer of a composition containing a polymer binder with more layers C08J7/042
• CPC Class Codes: C08J 7/043 Improving the adhesiveness of the coatings per se, e.g. forming primers adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50
• CPC Class Codes: C08J 7/046 Forming abrasion-resistant coatings; Forming surface-hardening coatings
• CPC Class Codes: C08K 5/541 containing oxygen
• CPC Class Codes: C09D 7/48 Stabilisers against degradation by oxygen, light or heat

Abstract

Monomers of the formulas R² (O-CH₂ CH(OH)(R)_a Si(OR¹)₃)_b and ##STR1## WHEREIN R and R¹ are generally lower hydrocarbyl groups, R² is an aromatic ultraviolet light-absorbing moiety bonded by aromatic carbon, a is 0 or 1 and b is 1 or 2 are useful in the formulation of light- and abrasion-resistant coatings for polymers.

Claims

1. A compound of one of the formulas ##STR9## wherein R is a divalent hydrocarbon or hydrocarbon ether radial of up to 10 carbons;

R¹ is an aliphatic hydrocarbon radical of less than 5 carbon atoms, an acyl radical of less than 5 carbon atoms, or a radical of the formula (CH₂ CH₂ O)_n Z in which n is an integer of 1 to 8 and Z is an aliphatic hydrocarbon radical of less than 5 carbon atoms;

R² is a stable, monovalent or divalent carbocyclic hydroxy-aromatic radical, containing up to 4 aromatic rings joined to oxygen through an aromatic carbon, of the type which absorbs light in the region of 2500-4000 A in an amount effective for stabilizing polymers against ultraviolet light;

a is 0 or 1; and

b is 1 or 2.

2. The compound of claim 1, the 1:

1 adduct of 2,4-dihydroxybenzophenone and α

-glycidoxypropyltrimethoxysilane.

3. The process of preparing a compound of claim 1 which comprises reacting at least one epoxysilane of the formulas ##STR10## wherein R is a divalent hydrocarbon or hydrocarbon ether radical of up to 10 carbons;

R¹ is an aliphatic hydrocarbon radical of less than 5 carbon atoms, an acyl radical of less than 5 carbon atoms or a radical of the formula (CH₂ CH₂ O)_n Z in which n is an integer of 1 to 8 and Z is an aliphatic hydrocarbon radical of less than 5 carbon atoms; and

a is 0 or 1,

with a compound of the formula

space="preserve" listing-type="equation">R.sup.2 (OH).sub.b

wherein

R² is a stable, carbocyclic hydroxy-aromatic radical, containing up to 4 aromatic ring joined to oxygen through an aromatic carbon, of the type which absorbs light in the region of 2500-4000 A in an amount effective for stabilizing polymers against ultraviolet light; and

b is 1 or 2,

under anhydrous liquid conditions in the presence of an alkyl quaternary ammonium salt.

4. The process of preparing a compound of claim 2 which comprises reacting 2,4-dihydroxybenzophenone and γ

-glycidoxypropyltrimethoxysilane under anhydrous liquid conditions in the presence of an alkyl quaternary ammonium salt.

7. A compound of claim 1 wherein R² is selected from the group consisting of ##STR13##

8. The compound of claim 1, the 1:

2 adduct of 2,2'"'"',4,4'"'"'-tetrahydroxybenzophenone and γ

-glycidoxypropyltrimethoxysilane.

9. The compound of claim 1, the 1;

2 adduct of 2,2'"'"',4,4'"'"'-tetrahydroxybenzophenone and β

-(3,4-epoxycyclohexyl)ethyltrimethyloxysilane.

10. The process of preparing the compound of claim 8 which comprises reacting 2,2'"'"',4,4'"'"'-tetrahydroxybenzophenone and γ

-glycidoxypropyltrimethoxysilane under anhydrous liquid conditions in the presence of an alkyl quaternary ammonium salt.

11. The process of preparing the compound of claim 9 which comprises reacting 2,2'"'"',4,4'"'"'-tetrahydroxybenzophenone and β

-(3,4-epoxycyclohexyl)ethyltrimethoxysilane under anhydrous liquid conditions in the presence of an alkyl quaternary ammonium salt.

5. A compound of the formula ##STR11## wherein R is a divalent hydrocarbon or hydrocarbon ether radical of up to 10 carbons;

R¹ is an aliphatic hydrocarbon radical of less than 5 carbon atoms, an acyl radical of less than 5 carbon atoms, or a radical of the formula (CH₂ CH₂ O)_n Z in which n is an integer of 1 to 8 and Z is an aliphatic hydrocarbon radical of less than 5 carbon atoms;

R² is a stable, monovalent, carbocylic hydroxyaromatic radical, containing up to 4 aromatic rings joined to oxygen through an aromatic carbon, of the type which absorbs light in the region of 2500-4000 A in an amount effective for stabilizing polymers against ultraviolet light; and

a is 0 or 1.

6. The process of preparing a compound of claim 5 which comprises reacting an epoxysilane of the formula ##STR12## wherein R is a divalent hydrocarbon or hydrocarbon ether radical of up to 10 carbons;

R¹ is an aliphatic hydrocarbon radical of less than 5 carbon atoms, an acyl radical of less than 5 carbon atoms or a radical of the formula (CH₂ CH₂ O)_n Z in which n is an integer of 1 to 8 and Z is an aliphatic hydrocarbon radical of less than 5 carbon atoms; and

a is 0 or 1,

with a compound of the formula

space="preserve" listing-type="equation">R.sup.2 OH

wherein

R² is a stable, monovalent, carbocyclic hydroxyaromatic radical, containing up to 4 aromatic rings joined to oxygen through an aromatic carbon, of the type which absorbs light in the region of 2500-4000 A in an amount effective for stabilizing polymers against ultraviolet light;

under anhydrous liquid conditions in the presence of an alkyl quaternary ammonium salt.